[00:00:00] Nathan: Growing from $500,000 per year to $5 million a year takes five specific things, and I broke it down today up on the board using Matt Trinetti’s membership as an example.

[00:00:10] Matt: You’ve built a really impressive business.

[00:00:12] Nathan: Matt is the co-founder of London Writers Salon, where 1,000 writers gather every weekday to write together.

[00:00:18] Matt: When I look at your business, there’s a ton of potential.

[00:00:21] Nathan: The first thing you need is a clear mission and vision.

[00:00:24] Matt: They skip past what matters most- Yeah … which is mission. This is

[00:00:26] Nathan: really important. Second is knowing your funnel and your conversion rate at every step.

[00:00:30] Matt: We have to care about the funnel. You start to notice these trends, you’re like, “Oh, wait, all traffic is not created equal.”

[00:00:35] Nathan: Third is retention. Because if members keep leaving, no amount of marketing is going to fix that.

[00:00:40] Matt: What is your monthly churn rate on your membership? It’s roughly 3 to 5%. 3 to 5% monthly churn is really quite good.

[00:00:45] Nathan: I even pull up some of Kit’s own numbers. ‘

[00:00:47] Matt: Cause that churn rate for us is 18%. Wow.

[00:00:50] Nathan: And some of these fixes are surprisingly simple.

[00:00:51] Matt: I worry about the ones that don’t fill out the survey. The silent reason people are canceling. Two things that I would recommend. One, I would like to pause for 90 days. That’s smart. Second thing everyone can implement on retention is pricing. That’s smart. Um, my wheels are turning.

[00:01:06] Nathan: Fourth is your products.

[00:01:07] Matt: Silver and gold don’t tell me anything. I know. Who should choose the gold plan? This is, uh, a bugaboo for me. How can we get more clear value and more commitment? And what I would be doing is I would say, “Hey-” That’s really good.

[00:01:17] Nathan: Then there’s the fifth thing.

[00:01:19] Matt: The final part is- Yeah, I’m kind of, like, excited to figure this out, though.

[00:01:22] The crazy thing is- I love that …

[00:01:24] Nathan: stick around for that one before you spend another dollar on getting new members.

[00:01:27] Matt: Oh, wow. That was impressive. That was great. This is, really is a masterclass.

[00:01:37] Nathan: All right, so Matt, I wanna dive in with the numbers. How many members do you have in your community right now?

[00:01:41] Matt: We currently have 2,000 paying members, and that’s across three different tiers.

[00:01:45] Nathan: 2,000 members. How much revenue, uh, did you do last year?

[00:01:48] Matt: So we were just over 500,000 last year, and this year we’re on pace for about 750,000.

[00:01:54] Nathan: What’s the team look like?

[00:01:55] Matt: We’re about three to five full-time to part-time, and then we have another 20, 30 contractors, coaches, supporters across different areas of the business.

[00:02:05] Nathan: Okay.

[00:02:06] Matt: Yeah. That

[00:02:06] Nathan: sounds good. Give me a sense of the, the product breakdown and, and prices. I, I understand you’ve got three main tiers?

[00:02:12] Matt: Yeah. So we, our core revenue, our core product is a membership. Yeah. And we have three tiers within that membership. And some of this is a hangover of our Patreon days. That’s where we started the membership. Okay. But the first tier, it’s called the Writers Hour Member Tier, and that is the focused writing sessions we do.

[00:02:28] Mm-hmm. There’s 20 plus silent writing sessions every day, so you get access to that.

[00:02:31] Nathan: Okay.

[00:02:32] Matt: So Writers Hour Tier, that’s about $16 a month. The next tier, uh, which we call Silver Membership, again, this is a hangover from our Patreon days, uh, that’s about $49 a month. That includes everything, all the writing sessions, plus we do weekly workshops, interviews.

[00:02:46] Okay. We have a recording library, all sorts of great stuff, great community. The third tier is Gold, and this includes all of that, plus weekly group coaching.

[00:02:54] Nathan: Okay, and what does this cost?

[00:02:55] Matt: That’s 149 a month.

[00:02:58] Nathan: Is that the full product offering, or you have something else in there?

[00:03:00] Matt: So this is the core product offering, and then we also, just that last year, we introduced a, a new product called the Manuscript Accelerator- Okay

[00:03:09] or The Residency. Um, and so that’s a cohort-based product. Members get discounts to it. Uh, but that’s for anyone who’s in the middle of a manuscript, a book, and they want to get to the end. Okay. And it’s a 10-week program. Uh, it’s about, uh, just over $3,000, uh, for those 10, 10 weeks. It’s weekly coaching, small cohort of people, all meant to make progress toward their, their book goal.

[00:03:30] Nathan: All of this revenue is recurring, and The Residency would be-

[00:03:34] Matt: That’s

[00:03:34] Nathan: right … one time.

[00:03:35] Matt: Yeah.

[00:03:35] Nathan: And then if we look at the, uh, revenue numbers from last year-

[00:03:38] Matt: Mm-hmm …

[00:03:38] Nathan: what would the breakdown be between… Like, what percentage came from the membership versus from The Residency?

[00:03:44] Matt: Yeah. So this was brand new last year.

[00:03:46] Okay. We did our first intake in October, so that- Mm-hmm … that was totally brand new. So this- Membership is, let’s say, roughly 80%.

[00:03:54] Nathan: Okay.

[00:03:55] Matt: And then this is slowly creeping into close to 15%- Yeah … will be of, well, the math won’t add up, but we have a, a few other streams. And then

[00:04:03] Nathan: you have miscellaneous-

[00:04:04] Matt: Yeah

[00:04:04] Nathan: things that add up to- Yeah … others. And then do you think residency is growing as a percentage of revenue?

[00:04:09] Matt: It is. We did the first intake last year, we just had one intake- Uh-huh … and now we’re planning to do three i- intakes over the year. Okay. Um, so there probably is a little bit of a ceiling to that.

[00:04:18] Mm-hmm. But I think we can include more cohorts, more coaches if we need to. Yep.

[00:04:23] Nathan: I like it.

[00:04:24] Matt: Yeah. No. Okay. It’s, it’s been transformative actually-

[00:04:26] Nathan: That’s a good

[00:04:27] Matt: business … the business. Yeah.

[00:04:28] Nathan: So where do you wanna take it? Obviously you’ve mentioned that you wanna take it to the- Yeah … five, five million in revenue, but let’s kind of map out the goal over here.

[00:04:35] Matt: Yeah. So the goal is, you know, roughly over 500,000 last year, growing to five million. Yep. So that’s a, a 10X increase. There’s two, that’s the monetary goal. Uh-huh. And really, I mean, the thing about money, I’m sure this is a conversation you guys have all the time about money, but it’s a, it’s a proxy for the value we’re providing- Yes

[00:04:53] for people. So this alone isn’t… It’s exciting. It’s not that motivating without- The other part which is serving more writers. Yeah. And so if we … The other, the flip side of this is we currently have 2,000 members. We’d love to- for that to be closer to 20,000-

[00:05:09] Nathan: Okay. I

[00:05:10] like

[00:05:10] Matt: it … that are, yeah, part of our community of practice, writing together, committing to a writing practice.

[00:05:15] So these two goals in tandem, I think. Yeah. And we talked about this a little bit earlier, like this, this without this is shallow, and this without this, it’s kind of not correct. It’s unsustainable.

[00:05:26] Nathan: Yeah. Yeah. I love that. A lot of people get caught up in, you know, like, “Oh, I should only focus on, you know, the success of the customer.”

[00:05:33] Matt: Mm-hmm.

[00:05:34] Nathan: Or, or they go the other way. Actually, honestly, more people get caught up the other way- Yeah … where they’re only caring about their own success. But exactly as you said, they go hand-in-hand.

[00:05:41] Matt: Right.

[00:05:42] Nathan: So,

[00:05:42] Matt: yeah. And if I’m honest, sometimes because we are so mission-driven- Uh-huh … we’re, we’re more focused on serving more writers.

[00:05:49] Yeah. So if I’m a little honest, I’m putting … I’m … It’s a little uncomfortable for me to- To say, right? … set a goal like that. Yeah. For many reasons, just because I don’t want this to be the primary focus, but also that’s not really the motivator. It’s serving more people. Yeah. But this is just a proxy, a metric- The

[00:06:06] Nathan: revenue goal

[00:06:07] Matt: is-

[00:06:07] for that we’re doing.

[00:06:07] Nathan: Yeah. So. That makes sense.

[00:06:09] Matt: Which I don’t know if that resonates with other, you know, creator businesses that-

[00:06:13] Nathan: I, I think it absolutely does- Yeah … because people are, uh, caught in this tension. Yeah. And, and especially because it feels like today saying you’re focused on revenue or profit is

[00:06:22] You know, it’s like, “Oh, that’s bad.” Mm-hmm. You know, people say like, “Oh, this, this, uh, company is trying to maximize profits, and they’re evil,” or, or whatever else.

[00:06:30] Matt: Right.

[00:06:30] Nathan: There’s a quote that I love that I thought of Seth Godin. I can’t attribute it to Seth Godin, so now I said it. And that’s just that profit is permission to do it again tomorrow.

[00:06:40] Matt: Mm-hmm.

[00:06:40] Nathan: And if you wanna run a sustainable business, you have to be profitable, right? Uh, I think there’s a lot of writing communities that don’t exist anymore because they weren’t able to run. That’s true. Maybe they were a nonprofit, or maybe they didn’t get the business aspect styled in, and, you know, they, they weren’t able to sustain themselves.

[00:06:57] Matt: 100%.

[00:06:58] Nathan: And so if you’re able to say like, “Hey, we can build a thriving business that has a huge impact on members,” then, like, guess what? You’ll be doing this in 10 years. Yeah. And you’ll go from impacting 2,000 to 20,000 people.

[00:07:08] Matt: Yeah. And that’s why … And I, I see that. I’ve, we’ve watched these organizations crumble.

[00:07:13] Mm-hmm. And writing’s too important, and the writing practice is, is too important to, to not exist, so.

[00:07:18] Nathan: I love that.

[00:07:19] Matt: Yeah.

[00:07:19] Nathan: So as we talk about going from 500K to 5 million- Mm-hmm … we’re just trying to add a zero. No big deal. Yeah. Let’s go up by an order of magnitude. Uh, I’ve got five steps that I wanna take you through.

[00:07:29] Matt: Yeah.

[00:07:30] Nathan: And you actually touched on the first one that I think is most important. And so many people skip past it. They wanna get into funnel. They wanna get into all these other things. Mm-hmm. They skip past what matters most, which you touched on-

[00:07:39] Matt: Yeah …

[00:07:39] Nathan: which is mission.

[00:07:40] Matt: This is really important.

[00:07:41] Nathan: And we- And we’ll put vision on here, too, as well.

[00:07:43] Yeah. You need to put numbers to it to be able to rally everyone together. What is the mission for your organization?

[00:07:48] Matt: It’s kind of lofty.

[00:07:49] Nathan: Yeah?

[00:07:50] Matt: But we want to help every individual develop and sustain a writing practice.

[00:07:55] Nathan: Mm-hmm.

[00:07:56] Matt: And why a writing practice is that writing is one of the most easily accessible tools into things like reflection through journaling, contemplation, self-awareness, communication- Right

[00:08:08] imagination, influence. And it’s, again, one of the most accessible tools, and we’re at this really interesting nexus point with humanity, I feel, that it might be the last thing we haven’t yet offloaded to technology. Right. In the same way we’ve offloaded our navigational abilities to Google Maps- We don’t

[00:08:25] and our mobile abilities to cars and other things.

[00:08:28] Nathan: We don’t, we don’t, uh, memorize phone numbers anymore. Yeah. That’s not a thing. Yeah.

[00:08:32] Matt: And it’s a practice for deep thinking. And you know as a writer, like what that can do both personally, but also for a business, but it’s not just about that. So yeah, we’re j- we’re at this interesting nexus point of humanity, and we want…

[00:08:43] We’ve been fortunate to create a space of belonging and creating the conditions to make building a writing practice really easy and fun. Mm-hmm. Because we give writers, who are essentially, it’s kind of a lonely pursuit, whether you’re just journaling or trying to write a book, we give them colleagues in a way- Mm-hmm

[00:08:59] and a space within community to stay committed to the practice. So anyway, that’s… I can get on that hi- high horse all day, but I think we’re at this really interesting point. And maybe I can say one more thing- Yeah … is that I think the hypothesis is that- Creative health, I think will start to become a category in the same way physical health has.

[00:09:17] Mm-hmm. So this shift that physical health went in the ’70s, where workouts and exercises wasn’t just for athletes anymore, there were people running, gyms popping up. Today, we look, every corner has yoga studios, CrossFits. I think a similar renaissance will happen with creative acts. Mm-hmm. And time spent in creative acts, not because necessarily you’re trying to grow an audience, that might be part of it, but really for a sense of connection to yourself, a sense of connecting to your brain and your- your deep thinking muscle.

[00:09:47] So anyway, we wanna be part of that conversation. So back to the mission and vision. Yeah. We think writing is a really great accessible tool to stay connected to that, and we wanna help more people achieve that.

[00:09:57] Nathan: Yeah, I love that, especially because now I’m seeing so many people who used AI to accelerate their output or that sort of thing- Yeah

[00:10:04] which is great. I’m- I’m thrilled that they did that and are accomplishing so much more. It’s when it feels like, oh, you used AI, you outsourced your thinking. Right. And you get these documents or these things, and you’re like, I don’t, I don’t think you not only believe every single word in here, I don’t think you understand every single word- Right

[00:10:19] in this. And so, yeah, like any muscle, if you don’t exercise it- Yes … you will lose it.

[00:10:25] Matt: Yes. Yeah, and I feel it, and- and I don’t know if you feel it too. Like, as someone who writes, I’m feeling that muscle atrophy a little bit- Mm … when I shift more into, okay, I’m just gonna stick it in here first to see what it, what comes out.

[00:10:36] Right. But I’m not doing that deep thinking, which I still do in my notebook-

[00:10:40] Nathan: Yes …

[00:10:40] Matt: to start, you know? So- Yeah … anyway, that’s the … Did I explain that well? Yeah, no, that- that’s perfect. Yeah.

[00:10:45] Nathan: So then the, where the vision comes out is the, you know, the question of, like, how would you know if you achieved your mission?

[00:10:51] Matt: It’s a good question. I mean, numbers help.

[00:10:54] Nathan: Mm-hmm.

[00:10:54] Matt: So to know, we do these writers’ hours, they’re live over Zoom. We have up to 1,000 writers every day writing in these four sessions across the day. If that number was growing- Yeah … so we can visibly, visually see people, um, writing, that- Mm … that will be one indicator that- that the message, me- message and- and mission is growing.

[00:11:14] Yeah, I think just, like, bodies,

[00:11:16] Nathan: like, to see. So we might articulate part of the vision, you know, of 20,000-

[00:11:20] Matt: Mm …

[00:11:20] Nathan: um, active members. Is that how?

[00:11:23] Matt: Yeah, I mean, that would feel really exciting. Yeah.

[00:11:26] Nathan: Okay. Let me give you an example from Kit. Mm. So first, I love starting with the mission and- and full credit, uh, I was listening to Travis Kalanick on David Senna’s podcast.

[00:11:36] Mm. And David asked him this question, and- and Travis goes, “Hold on a second.” You know, about, like, what Adam’s, Travis’ new company- Mm … so this is the founder of Uber, what his new company is doing, and he says, “Well, hold on a second. Let’s start with the mission. It’s easier that way.”

[00:11:49] Matt: Mm-hmm.

[00:11:50] Nathan: And I feel like in so many conversations- If we, you know, we’re in the weeds.

[00:11:55] La- later we’ll get into funnels. Yeah. We’ll get into all of these other metrics and things that matter there. But if we keep zooming out and say, “Hey, let’s start with the mission.”

[00:12:02] Matt: Mm.

[00:12:02] Nathan: It’ll make everything else easier.

[00:12:03] Matt: Mm.

[00:12:04] Nathan: I think that’s so important. So using Kit as an example.

[00:12:06] Matt: Yeah.

[00:12:07] Nathan: Our mission for years has been we exist to help creators earn a living.

[00:12:11] Matt: Mm.

[00:12:12] Nathan: We’ve since evolved that to say, “Hey, now we’re … You know, our mission is to help creators build valuable businesses.” So not just valuable for themselves and their families, but, like, creating value through all of the community members and readers and viewers- Mm-hmm … that they impact. But that’s, like, high, lofty.

[00:12:28] How do you know if you achieved that? There’s no way to know.

[00:12:30] Matt: Yeah.

[00:12:31] Nathan: And so the vision part of it is where you actually articulate, okay, let’s put some numbers to this.

[00:12:37] Matt: Mm.

[00:12:37] Nathan: And so there’s three main numbers that articulate our vision. The first is $1 billion-

[00:12:44] Matt: Mm …

[00:12:44] Nathan: paid by Kit to creators.

[00:12:46] Matt: Mm.

[00:12:47] Nathan: And so we track that, because, like, okay, well, we can directly see how much money- Mm

[00:12:51] we’ve paid out through product sales, sponsorships, paid recommendations, all of those features. And so we can keep the team aligned, like, how are we doing against this goal? The second one is, uh, an amount of revenue for us, right? And so we have 100 million in annual recurring revenue as the goal.

[00:13:08] Matt: Mm.

[00:13:09] Nathan: And today, we sit right at about 55 million.

[00:13:11] The reason that that’s so important to articulate is we have to bring the team along. They have to understand where we’re going, what they’re a part of. And as a founder, a lot of your job is to articulate a mission and vision that’s so big-

[00:13:26] Matt: Yeah …

[00:13:26] Nathan: that your team can see their own mission and vision for their life-

[00:13:30] Matt: Mm

[00:13:30] Nathan: fitting inside of that.

[00:13:31] Matt: Mm.

[00:13:32] Nathan: So if you say, “Hey.” I want to grow from 500,000 to a million in revenue, and we want to double our membership. There might be people that you want to recruit to their team, and they’re like, “I would love to that, but that means I’ll never earn more than-

[00:13:47] Matt: Mm …

[00:13:47] Nathan: X amount.” Like, your mission is not big enough to fit my-

[00:13:50] Matt: Hm

[00:13:50] Nathan: mission inside of it.

[00:13:51] Matt: Yeah.

[00:13:52] Nathan: And so that’s why it’s so important, one of the reasons why it’s so important to articulate something really, really big.

[00:13:57] Matt: Mm. I’ll tell you just real quick, this increasingly has become a motivator for me. The team, actually. Mm. The team. Yeah. I don’t know if you’ve felt this, but seeing that we can help provide a place for people to kind of look after their lives and their families, it…

[00:14:11] That, for me personally, as a founder, um, s- that’s starting to, uh, emerge as a motivator. Yeah. So that, that resonates a lot.

[00:14:18] Nathan: Mm-hmm.

[00:14:18] Matt: And actually in many ways, hearing you talk about that, I’m like, “Man, this actually feels pretty small.” You know?

[00:14:23] Nathan: The great thing is you can- Yeah … always change these.

[00:14:25] Matt: Yeah.

[00:14:25] Nathan: Right?

[00:14:25] And, and so you might want to make it even bigger. You might say 100,000. You might, you know, whatever it is. Right. ‘Cause it can be lofty. And, like, we’ve shifted ours over time.

[00:14:34] Matt: Mm.

[00:14:35] Nathan: So originally, our goal was a billion dollars, uh, earned by creators on the Kit platform.

[00:14:40] Matt: Mm.

[00:14:41] Nathan: And we actually hit that maybe four years ago.

[00:14:43] Matt: Wow.

[00:14:44] Nathan: Because we could track all the revenue that you were earning through, you know, everything that you were doing. Yeah. And, and email was powering that. And so once we hit it, we said, “Okay.” You know, we- we had a discussion, like should we raise that to 10 billion? And then we said, “No, no, no. Actually, we want it a billion dollars paid by Kit directly.”

[00:15:00] Matt: Mm.

[00:15:01] Nathan: You know, like it has come from our bank account to yours. Wow. Mm. And that’s a way harder goal, you know. Currently, we’re on track to do that in, like, 17 years. Right? And so now we’re like, okay, how do we accelerate that to- Mm … uh, get to the point that we’re paying out, you know, not 50 million or 80 million total, but $50 to $80 million a year, and then faster and faster from there.

[00:15:21] Matt: Right.

[00:15:21] Nathan: And ultimately, we want to get to the point where we’re paying out, you know, a billion dollars a year to creators.

[00:15:26] Matt: Mm.

[00:15:26] Nathan: And that’s how the goal will shift.

[00:15:27] Matt: Yeah. It’s interesting, ’cause now I’m thinking, okay, what is that for us? Mm. Because this still is a… For you, this might be the number of people using Kit.

[00:15:35] Yeah. But actually, how are these people’s lives different and better-

[00:15:40] Nathan: Mm-hmm …

[00:15:40] Matt: because they’ve joined us? Mm. And I don’t know if that’s time spent in Creative Act, time spent writing. I’m not sure what that is, but it’s giving… I’m- I’m w- wondering if actually what’s that… Because we’re not, like you- Like Kit, we’re not helping people earn a living necessarily.

[00:15:58] That might be one of their paths, but that’s not our direct goal. Mm-hmm. So it’s more so kind of the intrinsic, am I sitting down to do the work?

[00:16:06] Nathan: Yeah.

[00:16:06] Matt: So, or just to sit and journal.

[00:16:08] Nathan: One thing that it made me think of, you know, I wrote down impact, and the, a thing that I always align the team around, and even our community, is thinking about not just, like, okay, great, as a, as a creator on the platform, here’s the impact that Kit has had on you.

[00:16:23] Mm-hmm. Helped you hit a revenue goal, hit a subscriber goal. But also, like, writing, content creation, all of these things have an impact on people.

[00:16:33] Matt: Mm-hmm.

[00:16:33] Nathan: Right? And so for us, we talk about the, I think it’s like 700 million active subscribers- Mm-hmm … that are on the Kit platform. You know, if you think about your favorite writers and podcasters who are sending out their newsletter that’s, like, impacting people’s lives and- Yeah

[00:16:45] the content and all that. And so we keep recentering on that. And so I have these graphics I’ll draw of, like, you know, we’re a team of 115, and we impact, you know, it’s, it’s, I think we’re at 108,000 active users on Kit- Mm-hmm … ev- who, who are active every month. And then those 108,000 impact- Mm-hmm … 750 million people-

[00:17:05] Matt: Mm-hmm

[00:17:06] Nathan: that they reach.

[00:17:07] Matt: Interesting.

[00:17:07] Nathan: And that’s the kind of thing that’s really important.

[00:17:09] Matt: Yeah.

[00:17:09] Nathan: The other thing is, we don’t need to spend too much more time on this. Mm-hmm. But, um, I also really like counterbalancing goals. So I mentioned two of Kit’s goals, which are the one billion paid to creators, the 100 million in annual recurring revenue for, um, for our company.

[00:17:23] And the third one that’s really important is 250,000 active creators on Kit.

[00:17:29] Matt: Mm.

[00:17:30] Nathan: And the reason that we have that is any software company that you’re trying to grow, the, the best way to grow revenue is to move upmarket, start offering enterprise plans, and do all these things, and really to leave behind the beginner.

[00:17:44] Because they’re not that profitable, they churn, all this stuff, and we didn’t wanna do that. Like, that starts to go at odds with our mission.

[00:17:50] Matt: Yes.

[00:17:51] Nathan: And so we added that, that, okay, 250,000 active creators on the platform c- as part of our vision, because you can only achieve that if you continue to serve the beginner- Mm

[00:18:03] the long tail, the entry-level person.

[00:18:04] Matt: Mm. Hey, just a quick note before we keep going. If you usually just catch episodes whenever they pop up in your feed, take a second, hit subscribe or follow. We’ve got some great conversations coming up, and that’s the easiest way to make sure you don’t miss them.

[00:18:18] Thanks so much for your support.

[00:18:19] Nathan: And I think you have a similar aspect. Something that I loved- Yeah … like digging into your site, in this $16 a month- Mm … program, I mean, it’s a low price point, and then I noticed that you also have a, like a scholarship version of it.

[00:18:32] Matt: Yeah.

[00:18:32] Nathan: Where you’re, like letting people in, just say, hey, if…

[00:18:35] W- how do you structure that?

[00:18:36] Matt: Yeah. And this… And maybe I rewind a little bit because- Yeah … the way… I think the origin story’s kind of interesting, is that we started this, Writer’s Hour- Mm-hmm … in the pandemic. Mm. Like many people, they were doing things online. We were one of them, and we thought, let’s invite…

[00:18:51] We’re gonna do two weeks, 8:00 AM, Monday to Friday, join us and write together in silence. And we called it Writer’s Hour, and we… It was free. There was no monetary. The first day, someone said, “I got more value, more writing done in 50 minutes than I have in the last five months. Do you have a Patreon or something?”

[00:19:07] Nathan: Yeah.

[00:19:08] Matt: And so that was the first time anyone had been offering to give us money, give me money- Yeah … for anything. I’ve done a lot of entrepreneurial things. So the next day, we did have a Patreon. And so I’ll, I’ll get to why this matters. At ab- about a year and a half, we shifted from a- It’s free. If you get value out of it, here’s how you can donate.

[00:19:26] Nathan: Mm-hmm.

[00:19:27] Matt: To, here’s the price, but if you can’t afford it, here’s a no questions asked, we’ll give it to you for free. Mm. And what that did is that a lot of people actually wanted to pay, because it was a proxy for their own commitment to their- Yeah … writing practice. And we were actually leaving a lot of money on the table for the business, but also a lot of intrinsic value for them- Mm

[00:19:46] by giving them the opportunity to say, “This matters to me, and I’m going to pay for it for my own self.” So all that to say, that’s why we kept that very generous policy in place, because we never want community and writing to be something that people can’t access because they can’t afford it. We have so many people who are either in rural locations- Mm

[00:20:07] disabled, elderly, in a tough financial spot, that they get to connect with a wider community of people that they, even in the best of times, wouldn’t have been able to. So anyway, that’s –

[00:20:18] Nathan: Yeah …

[00:20:19] Matt: why that’s important. But we do have a price. And

[00:20:20] Nathan: now, if anyone questions it, you can, you point to the, the mission-

[00:20:23] Matt: Yes.

[00:20:23] Nathan: Yeah … right, of what you’re trying to accomplish, and you articulated that really well. All right. So as we think about scaling a membership from 500,000 to five million-

[00:20:30] Matt: Mm-hmm …

[00:20:31] Nathan: there’s a lot of things that people skip past, and mission is the thing that I think everyone skips past. And so I love that we spent as much time on that as we did.

[00:20:39] Now, uh, give me the… I realize I didn’t write it down. Give me the, the short version that we keep referring back to- Yeah … of the mission.

[00:20:45] Matt: So it’s to help every individual develop and sustain a writing practice.

[00:20:51] Nathan: And I think this is just important to have- um, up here so we can keep referring back to it.

[00:20:57] Matt: Yeah.

[00:20:57] Mm-hmm. ‘

[00:20:58] Nathan: Cause it really, if you were writing it out, you would, you know, start with the mission and then articulate the vision- Yeah … usually with a few metrics beneath it. So you know, this goes right up there. About a year ago, I had Julia Taylor, the founder of GeekPack, on the podcast. Mm-hmm. And she said that one of her KPIs that she tracks as a founder is how many times a week does she articulate publicly-

[00:21:19] Matt: Mm

[00:21:20] Nathan: their mission.

[00:21:20] Matt: Mm.

[00:21:21] Nathan: On podcasts, in front of the team, in front of customers, all of that, to just keep recentering everyone. Because if you’re trying to say, “Okay, I’m try- I’m building a, a membership or a community that’s way bigger than me.”

[00:21:32] Matt: Mm-hmm.

[00:21:33] Nathan: Just always keep coming back to the mission.

[00:21:34] Matt: Mm-hmm.

[00:21:35] Nathan: Okay.

[00:21:35] Matt: I love that.

[00:21:36] Yeah.

[00:21:36] Nathan: Hard pivot here. Yeah. ‘Cause now we’re going into numbers.

[00:21:39] Matt: Yeah.

[00:21:40] Nathan: The thing that matters after that, that we need to obsess over, is the funnel. And you might be like, “Well, hold on. No, no, no, we’re just mission-driven.” Mm. “We’re, you know, we just care about the touchy-feely side of it.” It’s like, okay, cool. Do you wanna be in business next week or next year?

[00:21:51] Matt: Yeah.

[00:21:52] Nathan: Like, we have to care about the funnel. The other thing that I feel like all membership operators get wrong is they usually make the jump from selling info products, digital products in some way, into membership.

[00:22:05] Matt: Mm-hmm.

[00:22:06] Nathan: And the- and they treat it the same way. But the thing is, you’ve switched. You’re running a SaaS company.

[00:22:11] Matt: Mm.

[00:22:11] Nathan: Right? You’re at 500,000 revenue. I mean, you’re on track for 750,000 in revenue. Mm-hmm. Like, there’s a lot of metrics that matter in here that you need to start caring about.

[00:22:19] Matt: Mm. Yes.

[00:22:20] Nathan: Um, the good news is there are thousands of SaaS companies out there, and there are tens of thousands of articles written on how to handle all the metrics- Mm

[00:22:28] what you should care about and all that. So we’ll do a little crash course on it right now. Um, but you have a lot of studying that you can do because you have to start thinking about this business so much differently than most people think about membership.

[00:22:41] Matt: Yeah. It’s … I, I’m, I’m feeling like we have to mature in this way.

[00:22:44] Mm-hmm. That feels uncomfortable. I’m sure every founder kind of goes through these levels of maturity of, like-

[00:22:48] Nathan: Yep …

[00:22:49] Matt: how you need to operate. And yeah, I agree, this is probably where we’re the weakest right now. We pretty much go on good vibes, word-of-mouth. We do have, like, podcasts, social media, but- Yep

[00:23:00] free events, but we don’t really have an engine. Mm-hmm. And we’re not cl- certainly not monitoring it about this right here.

[00:23:07] Nathan: All right. So on the funnel, if we’re just to map it out- Yeah, yeah … in the simplest terms. Right? So we’re gonna have, uh, visitors to your pr- you know, to your site, and you would wanna map out where are those coming from, what’s word of mouth, what’s referrals, uh, what’s paid ads, all of that.

[00:23:25] So you’d have, you know, a few different sources coming in. You have a, a trial right now that you offer, right?

[00:23:29] Matt: Yeah. This tier has a trial. There’s a free seven-day trial. Okay. Yeah.

[00:23:33] Nathan: And so then we’re going visitors into trials, and then you have some number of those that convert- Mm-hmm … into members. Mm-hmm.

[00:23:41] And so that’s … It’s a very simple funnel. Mm-hmm. But what you need to do is you need to put, uh, numbers to all of this.

[00:23:48] Matt: Mm-hmm.

[00:23:49] Nathan: And on each one, you’re going to track, uh, two things. We wanna track the total count, uh, on a weekly or monthly basis. If it’s a metric that you- care about deeply and you’re trying to move, track it on a, on a weekly basis.

[00:24:02] Matt: Mm.

[00:24:02] Nathan: If it’s a metric that you’re like, “Oh, I’m just kind of aware of that,” then monthly is fine. But this is very important, and so I would track it-

[00:24:08] Matt: Mm …

[00:24:08] Nathan: on a monthly basis. So the two things that we’re gonna track is the, uh, the stats for each one, so the total numbers, like total number of visitors, uh-

[00:24:16] Matt: And

[00:24:16] Nathan: that’s across

[00:24:17] Matt: each-

[00:24:18] Nathan: Yep

[00:24:18] Matt: category.

[00:24:18] Nathan: Uh, and all of that. And then you’re gonna track the conversion rates at any individual point. And a lot of people do these as a point in time, but you don’t actually want that. You wanna track it how the trend changes over time. Mm. So this is a really impor- These metrics are all really important to your business, and so we’re gonna track them on a weekly basis.

[00:24:38] Matt: Mm.

[00:24:38] Nathan: If it’s not that important and you’re monitoring it- Mm … you can do that monthly. But, like, these matter, so track them weekly.

[00:24:43] Matt: Weekly.

[00:24:44] Nathan: And so then what we’re gonna see in our table is, you know, for the week of August whatever, uh, we had this many visitors. Mm. Uh, we had this many trials and this many members, and the conversion rate between them- Mm

[00:24:57] at each stage was this.

[00:24:59] Matt: Mm.

[00:24:59] Nathan: And then you’re gonna graph those over time. So we’re graphing both the total numbers over time and then the, the trend in- Mm … conversion rate over time. And you’ll start to notice trends now. Mm. But what you’ll find is that you can then optimize, like pick a single metric and say, “You know what?

[00:25:14] For the next two weeks, I’m gonna really focus on improving this.”

[00:25:18] Matt: Mm.

[00:25:18] Nathan: So do you happen to know your visitor to trial?

[00:25:21] Matt: So, yeah.

[00:25:22] Nathan: Or trial to, uh, paid conversion rates?

[00:25:25] Matt: Embarrassingly, no, to visitors. Okay. Um, we do roughly know this. It’s roughly 27%.

[00:25:32] Nathan: Okay.

[00:25:32] Matt: Now, the caveat to that is that this is the only tier that has a, a trial.

[00:25:37] Nathan: Uh-huh.

[00:25:37] Matt: And also… And maybe we’ll get into the complexity of membership versus product later, but-

[00:25:42] Nathan: Yeah …

[00:25:43] Matt: sometimes I worry the value proposition of each of these are different. Right. So-

[00:25:47] Nathan: As people move between plans and

[00:25:48] Matt: yeah. Yeah. So some people jump right in here. We don’t really have a trial for that.

[00:25:51] Nathan: Mm.

[00:25:52] Matt: Sometimes we do occasional free events that gives them a taste of the community. We don’t really have a trial for this one either.

[00:25:57] Nathan: For the gold tier.

[00:25:58] Matt: Yeah. So it’s kind of we’re forcing everyone to funnel through this first tier, which broadly is the thing that people tend to come to us the most for.

[00:26:08] Nathan: Mm-hmm.

[00:26:08] Matt: And then we position these as escalating need states and value. If you’re looking for more craft support, if you’re looking for more community- Right … if you’re looking for more accountability and coaching, then people are in the ecosystem here, and then they will self-select-

[00:26:22] Nathan: Yep …

[00:26:22] Matt: to join those. But like I said, it’s- These have no trials other than listen to a podcast, attend an event.

[00:26:30] Yeah,

[00:26:30] Nathan: and generally if you focus on, uh, problems higher up the funnel first-

[00:26:35] Matt: Mm …

[00:26:35] Nathan: then, uh, you can solve the downstream ones later. Mm. So I wrote down upsells. So after someone be- you know, converts from a, a trial to a paying member, then later on you, you’ll upsell them to other plans.

[00:26:48] Matt: Mm-hmm.

[00:26:49] Nathan: And we can deal with that later.

[00:26:50] Matt: Yeah.

[00:26:51] Nathan: But just instrumenting this funnel, graphing it over time- Mm-hmm … you’ll start to notice a lot of things that happen. Mm-hmm. You’ll start to see, okay, are, are visitors spiking all over the place, or is our trial-

[00:27:00] Matt: Mm …

[00:27:01] Nathan: are our trial conversions going up and down a bunch?

[00:27:04] Matt: Mm. ‘

[00:27:05] Nathan: Cause a lot of people assume that conversion rates are a function of the funnel itself- Mm

[00:27:10] and, like, what’s on screen and all that, and that matters, but the intent of the traffic matters at least as much.

[00:27:16] Matt: Mm. Yeah, I’ve seen that.

[00:27:18] Nathan: And, and so you might, even before you do cohort analysis and all this fancy stuff, you might see, wow, we had way more visitors That’s amazing. Oh, wait, but our trial conversion went down like crazy.

[00:27:31] Matt: Right.

[00:27:32] Nathan: Oh, like, thing that we deal- we deal with bot traffic a lot. Mm. You know? Or it might be like, uh, we had that article that went viral. Oh, and that conver- the people who signed up for trials converted to members at 6% instead of 27%.

[00:27:43] Matt: Got it.

[00:27:44] Nathan: You start to notice these trends, and you’re like, “Oh, wait, all traffic is not created equal.”

[00:27:47] Matt: Mm.

[00:27:47] Nathan: Which we intuitively know.

[00:27:49] Matt: Right.

[00:27:49] Nathan: But it’s once we represent it in numbers.

[00:27:52] Matt: Yeah. And we- I’ve seen that before. We do this 24-hour writing sprint event- Uh-huh … every year. It’s the 24 hours of silent writing when we’ll have 3, 4, 5,000 people signed up to that. Mm-hmm. But it’s interesting that actually the

[00:28:04] I thought that would be our audience, but very few people actually convert into-

[00:28:08] Nathan: Yeah …

[00:28:09] Matt: a membership. So I, I see that in practice. But that

[00:28:11] Nathan: might be great for awareness.

[00:28:13] Matt: Yeah.

[00:28:13] Nathan: And then later on you’re retargeting those people or- Right … you could be doing other things.

[00:28:17] Matt: Yeah. True.

[00:28:18] Nathan: So in this, really the, the action item here on the funnel- Yeah

[00:28:21] is just instrument and monitor every step of the funnel.

[00:28:25] Matt: Yeah.

[00:28:26] Nathan: And then, you know, I’m gonna put a question mark down here as well. Basically, you’re g- you’re gonna have a stat for every one of these per week, and then a, a- Mm-hmm … a percentage for the, the number that move between that.

[00:28:37] Matt: Yeah.

[00:28:37] Nathan: And then you can ask questions of, like

[00:28:39] Okay, we’ll give you another example. Mm. So at Kit, we get 15 people a day who move from the 1,000-subscriber plan, which is our base plan, and graduate to the 3,000-subscriber plan.

[00:28:51] Matt: Mm.

[00:28:51] Nathan: And so on one hand, that’s a drop in the bucket compared to the huge amount of revenue. But if you look at the total, you know, the new revenue coming in- Mm

[00:28:58] it could be pretty meaningful. And so we have a team that sat down and said, “Okay, what would have to be true-

[00:29:04] Matt: Mm …

[00:29:04] Nathan: for instead of 15 people a day graduating, it to be 18?” It’s only three more people a day, but over 30 days in a month and 365 days in a year. Right. And the, the more they graduate, the more likely they are to retain.

[00:29:16] And so we have a team that’s just like, “All right. We’re gonna get three more people a day.”

[00:29:19] Matt: Mm.

[00:29:20] Nathan: And now they’re looking through everything. They’re digging into the details, and they have this very tangible metric to move.

[00:29:25] Matt: Mm.

[00:29:26] Nathan: And so you might be saying, “Okay, like, 27% trial conversion is pretty good.” But you’re like, “Okay, what would have to be true for this to be at 30%?”

[00:29:31] Matt: Mm-hmm.

[00:29:32] Nathan: And you go through the flow yourself. Yeah. You really dive in, and I bet you would find the improvements-

[00:29:36] Matt: Yeah … um,

[00:29:36] Nathan: to get

[00:29:36] Matt: to that. I already have some ideas here. I think- Mm … we kind of throw people into Writers Hour, which is, uh, those daily sessions, but we don’t really have a great, like, onboarding- Yeah

[00:29:45] or a great here’s how to set up your writing practice. We don’t really do that. We kind of just throw them in. So I imagine something there to make that- stickier for them- Yeah … when they do join. So I, uh, there’s already ideas to improve that.

[00:29:57] Nathan: I like that.

[00:29:58] Matt: Mm.

[00:29:58] Nathan: Um, there’s lots more on funnel that we could get into.

[00:30:00] Yeah. But I think this is enough for now. Once you go through all that, you’ll find there’ll be more to get into. The, the one flag that I will save for later- Mm … this would be the, like, uh, you finish all of this, like, the thing to work on later would be cohort analysis.

[00:30:14] Matt: Mm. I’m just gonna say cohorts.

[00:30:16] Nathan: Because basically what you’ll see is not all traffic is created equal, and it behaves very differently down the funnel. Yeah. Um, you don’t need to worry about that yet, but it will become very important.

[00:30:27] Matt: Yeah. Can I ask one question- Yeah … about this part in particular? The

[00:30:30] Nathan: upsells?

[00:30:31] Matt: I think we’re very good at…

[00:30:32] Our, our positioning is invitation versus upsell. Obviously, we never, like, use that word with our- Yeah … community. It’s very, “If this is what you’re looking for, we have this over here.” Some of our feedback has been feeling like, “Oh, am I constantly being upsold?”

[00:30:49] Nathan: Mm.

[00:30:49] Matt: Mm-hmm. And I’m just curious how you guys have done this, how other creators have done this to really…

[00:30:54] Again, this is just, it’s, it’s, we don’t want that to be the vibe. Yeah. That you’re constantly, “You’re here, but we always want you to be up there.” I’m curious if you- How

[00:31:02] Nathan: do you handle

[00:31:02] Matt: that? Yeah, if you have thoughts on- So the- That

[00:31:05] Nathan: question … the thing is, I’m realizing in our business, I would describe this as expansion.

[00:31:09] Matt: Yeah. Okay.

[00:31:09] Nathan: Maybe I just didn’t wanna write a word as long as expansion on the board.

[00:31:13] Matt: Yeah. No, I, I, I like that though, ’cause that, it, it’s, it’s a framing.

[00:31:16] Nathan: Yeah. And so, you know, they’re expanding their relationship with you, their ex- Yeah … their business ex- is expanding, um, all of that. At Kit, we have two forms of expansion.

[00:31:27] One is when your list size grows, you automatically move up, right? Mm-hmm. So someone paying us 10,000, uh, or who has 10,000 subscribers pays us more than someone who has 8,000. So we call that organic expansion.

[00:31:39] Matt: Hmm.

[00:31:39] Nathan: Um, and that just happens very naturally. And so we’re, we’re coming alongside you, and we’re like, “Hey, how can we help you grow your list faster, reach more people?”

[00:31:47] All of that. Hmm. And our incentives are very aligned. And then we have the upsell expansion, which is getting you to move from our creator plan, which is our standard paid plan, to our pro plan that has more features and, and all of that. So I’m not sure. A lot of memberships-

[00:32:03] Matt: Mm …

[00:32:03] Nathan: typically only have one kind of expansion.

[00:32:05] Matt: Mm.

[00:32:06] Nathan: Um, but it’s always worth thinking about is, are there two levers here, or is there a type of expansion that naturally aligns with the success of the customer?

[00:32:13] Matt: Mm-hmm. Yeah.

[00:32:14] Nathan: Does anything come to mind here?

[00:32:16] Matt: Yeah, I think we are often … So we do have emails and announcements every day, and often we’re pointing to all these other things that are happening.

[00:32:25] Mm. So it’s very much like, here’s what’s happening over here versus … It’s like an, it’s like a soft upsell where we’re not- Yeah … like … We do have some, and we’ll talk about this residency maybe in a bit, where that’s more of like a campaign, but it’s really just like signposting. These things exist. Yep. If that resonates, you’ll click through, and you’ll realize, oh, I need to be-

[00:32:45] Nathan: That’s the right fit for me.

[00:32:45] Matt: Yeah. Yeah. So I think just more of that. That feels like it aligns. Yeah, and I think,

[00:32:49] Nathan: um, in your, your wording, it’s an invitation- Yeah … it’s not a sale. Yeah. Maybe just say, say that. That can be really good.

[00:32:55] Matt: Yeah. I think that’s it.

[00:32:56] Nathan: Okay, so let’s keep moving.

[00:32:57] Matt: Yeah.

[00:32:58] Nathan: So as we go past funnel, right? This is everyone coming in.

[00:33:01] Mm-hmm. The next thing that really matters is retention. And so this is looking at, you know, what is your monthly churn rate-

[00:33:08] Matt: Hmm …

[00:33:08] Nathan: uh, on your membership? Do you happen to know the,

[00:33:11] Matt: the numbers? Yeah. I j- I, I didn’t, but I do. It’s roughly 3 to 5%.

[00:33:15] Nathan: 3 to 5%?

[00:33:16] Matt: Yeah. Kind

[00:33:16] Nathan: of like- Monthly churn.

[00:33:17] Matt: Yeah. Yep. Monthly churn.

[00:33:18] Nathan: As a membership- Uh, 3 to 5% monthly churn is really quite good.

[00:33:22] Matt: Oh, is it? Okay.

[00:33:23] Nathan: To give you an idea, Kit’s monthly churn, we differentiate between user churn and revenue churn.

[00:33:28] Matt: Mm.

[00:33:29] Nathan: Um, and what that does, typically people who pay you more are gonna stick around longer. You know, if I can afford paying $149 a month, I probably, uh, am fairly stable in what I’m doing. I probably have a higher income.

[00:33:44] Um, I’m probably r- am really committed to my writing practice rather than just like, ”

[00:33:47] Matt: Eh.” Mm-hmm. Yeah. Like, it’s probably important to me. And people here ge- generally, they’re either on deadline for a book. Mm-hmm. They need more support, so there’s their goal. It’s aligned with their- It’s important to them.

[00:33:56] It’s not- … their goal and ambition. Yeah.

[00:33:58] Nathan: It’s not a hobby. I always separate those out. So Kit- Mm … for example, has about a 3.5% monthly user churn.

[00:34:05] Matt: Mm.

[00:34:05] Nathan: And like a 3.1% monthly revenue churn.

[00:34:07] Matt: Separate.

[00:34:08] Nathan: So there, there’s two different things, right? User churn and revenue churn, and then you can assign these to each individual tier.

[00:34:15] Matt: Mm.

[00:34:15] Nathan: Because what you’re gonna see is like, oh, interesting, the silver and the gold tier both have additional services offered. Mm. You know, and these additional benefits. But for some reason, one is churning-

[00:34:25] Matt: Mm …

[00:34:26] Nathan: way higher than the other.

[00:34:27] Matt: Mm.

[00:34:27] Nathan: You might expect that the gold tier is churning, um, at a lower rate.

[00:34:31] Matt: Yeah.

[00:34:31] Nathan: Because they’re more invested. Mm-hmm. Well, you might find it’s churning at a higher rate because it’s more expensive.

[00:34:36] Matt: Mm-hmm.

[00:34:37] Nathan: Oh, it’s three times the price.

[00:34:38] Matt: Mm.

[00:34:38] Nathan: And so seeing the difference between month, um, between user and revenue churn, uh, or member and revenue churn-

[00:34:44] Matt: Mm …

[00:34:45] Nathan: is really, really important.

[00:34:46] Mm. And then you track it over time. And then what you wanna do is, this is where cohorts really matter. Let’s take two different types of visitors. So one of them might come in from your … a big challenge or the writers hour. Mm-hmm. You know. Yeah. They’re one of the, the 4,000 that all came in at once who

[00:35:03] They converted at a low rate, but they did make it all the way through to a member.

[00:35:06] Matt: Mm.

[00:35:06] Nathan: And you’re like, “Oh, that’s interesting. Okay.” Uh, and then the other was referred by a friend.

[00:35:10] Matt: Mm-hmm. Mm.

[00:35:11] Nathan: What I would most like, what I would expect to see- Mm … is the person referred by a friend-

[00:35:16] Matt: Mm …

[00:35:17] Nathan: has a way lower churn rate than the person who came in through a challenge or a paid ad.

[00:35:24] Matt: Yeah.

[00:35:24] Nathan: And all of that.

[00:35:25] Matt: I like that. So it’s not only channel. I know you can’t read that, but-

[00:35:28] Nathan: Yep …

[00:35:29] Matt: separating by tier, but also by way in.

[00:35:31] Nathan: Yeah.

[00:35:31] Matt: Yeah. That’s interesting.

[00:35:32] Nathan: And I want you to know that this is hard to do.

[00:35:34] Matt: Mm-hmm.

[00:35:35] Nathan: Like, these initial metrics are pretty easy.

[00:35:36] Matt: Yeah. ‘

[00:35:36] Nathan: Cause you’re tracking total stats and all of that.

[00:35:38] Then i- as you get into cohorts and attribution, it gets hard.

[00:35:42] Matt: Mm.

[00:35:43] Nathan: So like, you know, there’s a lot of software companies that it takes them a while to do this- Mm. Got it … or that sort of … or it requires some more sophisticated software. Mm. Um, but it’s totally worth it if you wanna scale. Mm. Do you wanna pause for a second- Yeah

[00:35:54] and check in? We’ve covered like three of the five main points. Yeah. All of that. How are you feeling? What questions do you have?

[00:36:01] Matt: I feel good. I feel … This is important. I, I’m realizing as we go down, it’s like my … I have less answers to.

[00:36:10] Nathan: Mm-hmm.

[00:36:10] Matt: And no, I think, I think it’s re- I think you’re right where it’s at.

[00:36:14] And I think- I imagine this is the nexus point for organizations like this-

[00:36:18] Nathan: Mm-hmm …

[00:36:19] Matt: where if they, they don’t decide to go into this level of granularity are, are the ones that kind of plateau. So it … Yeah, it feels both exciting, a little daunting, um, but I think, I think this all feels, feels right.

[00:36:33] Nathan: The other thing that I was noticing, you know, is 3, 3 to 5%- Yeah

[00:36:38] monthly revenue churn, or sorry, mon- monthly, uh, member churn, is those are really good numbers. Mm. Like I mentioned, I’ve seen a lot of memberships sit at 15%.

[00:36:47] Matt: Mm.

[00:36:48] Nathan: But there’s a lot that you can do here. And if you think about the points of leverage in a business, retention is one of the absolute biggest-

[00:36:59] Matt: Mm

[00:36:59] Nathan: in a monthly recurring revenue

[00:37:01] Matt: business. Yeah.

[00:37:02] Nathan: Because if you just imagine, you’re like, “Okay, we’re gonna get so good at attracting more and more people at the top of the funnel. We’re gonna dump … Invest all this in paid ads.” But if you have a leaky bucket and they’re just dumping out-

[00:37:14] Matt: Totally agree …

[00:37:15] Nathan: it, it’s just

[00:37:16] It’s a two steps forward, one step back- Yeah … continually.

[00:37:19] Matt: Mm.

[00:37:20] Nathan: And so I would track the retention numbers for a period of time. Mm. You can probably go back and calculate them. And some of these might be … You know, if you’re using Stripe for payments or things like that- Mm-hmm. Yeah … it might calculate it automatically.

[00:37:30] Yeah. But go back and track that. And then I would just set a goal.

[00:37:33] Matt: Mm.

[00:37:33] Nathan: Let’s say that it were … If we … Let’s say it’s hovering right around 4%.

[00:37:37] Matt: Mm.

[00:37:38] Nathan: I would say, “Okay, our goal on this is to get it to 3.5.” Right? Or 3.7. You know, and you’re just saying, “Okay, what can we do?” Mm. And then brainstorm four to five ideas.

[00:37:48] Matt: Mm.

[00:37:49] Nathan: Put them in sequence. You can’t do them all at once. You know, just like, look, uh, every week or every month we’re gonna implement these little things.

[00:37:57] Matt: Mm. Mm.

[00:37:58] Nathan: Um, and one of them might be a survey when someone, when someone cancels.

[00:38:03] Matt: Yeah.

[00:38:04] Nathan: Which we

[00:38:04] Matt: have. Which we have. We do have that now. Okay. Yeah, yeah.

[00:38:06] Nathan: Do you act on information from that?

[00:38:09] Matt: We reply to everyone. We ask them to reply as well. Uh-huh. And we reply to everyone, um, back. Yeah, it’s… I mean, honestly, a lot of it is financial and lifestyle changes. Mm-hmm. Which is nice, and actually a lot of people saying, “I’m canceling because I’m going on holiday for three months, but I- Yeah … I’ll be back.”

[00:38:25] That’s the ones we hear. I worry about the ones that don’t fill out the survey and that don’t answer. Mm-hmm. That’s the, the secret, the silent reason people are- Yes … canceling. So that’s the one I worry about.

[00:38:37] Nathan: Two things that I would recommend. Um, one, uh, you just described not a cancellation, but a pause.

[00:38:43] Matt: Yeah.

[00:38:44] Nathan: But in your flow, it has to be a cancellation.

[00:38:46] Matt: Yes.

[00:38:47] Nathan: So if you can change your flow where it says, “I would like to pause for 90 days.”

[00:38:52] Matt: Mm.

[00:38:52] Nathan: Or, “I wanna pause my subscription.” It’s like, “Great, how long? 30 days, 60, 90?”

[00:38:56] Matt: Mm.

[00:38:57] Nathan: And then let them do that, and then it automatically comes back- Mm … when they said they were done with their- Mm

[00:39:01] summer holiday-

[00:39:02] Matt: Yeah …

[00:39:03] Nathan: whatever else. I bet you would save a decent number.

[00:39:05] Matt: Mm.

[00:39:06] Nathan: Versus the person who’s like, “Oh, I’m canceling,” which to me is just a pause, and I’m totally gonna remember to renew. Mm-hmm. And it’s like, “No, no you’re not.” Mm. Yeah. You know? Like, we don’t, we don’t remember to do that. And on one hand, someone might argue like, “Oh, that’s a sneaky cancellation flaw,” or they said they wanted to cancel, and it’s like, no, no, they said they wanna be a writer.

[00:39:24] Matt: Yeah.

[00:39:24] Nathan: They said they wanna have a daily writing practice.

[00:39:26] Matt: Yeah.

[00:39:27] Nathan: And that accountability and the email saying, “Hey, the pause in your membership is coming to an end. Like, we’re so excited for you to restart-

[00:39:33] Matt: Mm-hmm …

[00:39:34] Nathan: the daily writing. Here’s our video. Here’s our tip on how to restart-

[00:39:39] Matt: Yeah …

[00:39:39] Nathan: your writing habit as you’re invited back to the community.”

[00:39:41] Matt: Yeah. I love that. Yeah, and actually people do request pause. Mm-hmm. Unfortunately, the platform we use, we’re on Circle. Uh-huh. Are you familiar with Circle? Yeah. We have limitation by the platform because we’re not custom-built. Okay. But we have a lot of people saying, “Hey, do you have a pause option?” Yeah.

[00:39:55] And we’re like, “Sadly, no. Just email us again.” So I totally understand that’s not-

[00:39:59] Nathan: But, uh- … the thing is … there might be… It’d be worth reaching out to the Circle team. Yeah, yeah. There might be something with Zapier or-

[00:40:05] Matt: Yes …

[00:40:05] Nathan: inside of Stripe or whatever-

[00:40:06] Matt: That’s, that’s smart …

[00:40:07] Nathan: where y- they trigger the pause option, and-

[00:40:10] Matt: Mm

[00:40:10] Nathan: it goes from there.

[00:40:11] Matt: Yeah. No, I think this is such a… This is actually, this is key.

[00:40:15] Nathan: We’re gonna add a pause.

[00:40:18] Matt: Yeah. I love the, the video idea too of like, I think we just need to do more of that kind of stuff. We’re fortunate we do a lot live, so we’re able to- Yeah … be that friendly face live in the room, but actually a video.

[00:40:30] Mm-hmm. I, I love this, these kind of ideas.

[00:40:32] Nathan: And then going back to, uh, Julia from GeekPack.

[00:40:35] Matt: Yeah.

[00:40:36] Nathan: That is an opportunity to reiterate your mission.

[00:40:38] Matt: Right.

[00:40:38] Nathan: You can say like, “Hey, you’re-” Yes … you know, “Your pause is coming to an end. We’re so excited to have you back. As you probably know, our mission-

[00:40:46] Matt: Mm …

[00:40:47] Nathan: is, you know- Yeah

[00:40:48] to help everyone develop a daily writing practice.”

[00:40:51] Matt: Yeah.

[00:40:52] Nathan: You know, and you choose what you enter, you know, but then they’re like, “Oh, man, I’m excited to come back,” instead of like, “Oh, shoot, I actually didn’t mean to cancel that.”

[00:40:58] Matt: Mm.

[00:40:58] Nathan: You know. Mm. ‘Cause they’re coming to you and saying, “Hey, I want this thing,” and you’re like, “Great.

[00:41:02] I’m here- Yes … to help you achieve

[00:41:03] Matt: that.” Yes. Mm.

[00:41:04] Nathan: Okay. The second thing that I think everyone can implement on retention is calls. Mm. And I would say I would pick some number of your users who cancel- Mm … uh, to get on calls with every week. Mm-hmm. It could be three, it could be five.

[00:41:17] Matt: Mm.

[00:41:17] Nathan: And just get on a call, do an interview, learn more, record it.

[00:41:20] Matt: Mm-hmm.

[00:41:21] Nathan: Save the transcript. AI is really good at going back through the calls and saying, “Hey, here’s the trends that are happening.” Mm. And so if you do those interviews and calls, then, um, you’ll learn so much more. Mm. And often just that quick little email like, “Hey, I just noticed you canceled. Um, if you’re up for it, I’d love to get on a 15-minute call and learn more.”

[00:41:41] Matt: Mm.

[00:41:41] Nathan: You know? Nice. “Here’s a- Love it … here’s a link to book,” you know? Mm. And a bunch of people will.

[00:41:45] Matt: Mm. I love

[00:41:46] Nathan: it. So Alyssa, who’s our director of customer experience at Kit, she gets on, like, 10 of these calls every week, just, like- Mm … always trying to learn ’cause she’s looking for all the friction points that make people cancel their membership.

[00:41:57] Mm.

[00:41:57] Matt: That’s smart. Um, my wheels are turning, so that’s really good.

[00:42:01] Nathan: Okay. Yeah. Uh, the next one that I wanna dive into-

[00:42:03] Matt: Yeah …

[00:42:04] Nathan: is products. So this is another big-

[00:42:06] Matt: Yeah …

[00:42:06] Nathan: leverage point. So you have, uh, a good mix of products here.

[00:42:10] Matt: Yeah.

[00:42:11] Nathan: Right? So we have the membership with three different tiers. Yep. And then we’ve got the residency.

[00:42:16] Matt: Yep.

[00:42:17] Nathan: Do you feel like there’s anything missing in your product stack, or is there anything that you wanna change?

[00:42:22] Matt: There’s two thoughts here. One is the residency came. So again, this is our highest ticket thing we’ve ever done. It’s white glove service. How do we help people get to the end of a manuscript?

[00:42:32] This came from knowing that Gold was great, but it actually wasn’t serving people- Mm … truly in the way that we could. And we felt it was easier, instead of trying to reimagine this tier of membership, creating a whole new product with a whole new value proposition- Mm … given all the insights we’ve learned about this tier.

[00:42:51] So we made the choice to have a separate product. Now, there’s other things that have come in our surveys that people are looking for something that is the community and experience of silver, but more what I’m calling craft tracks. So a more intimate group that maybe isn’t residency- Mm-hmm … but is aligned with someone who’s writing fiction, actually bringing those people together-

[00:43:15] Nathan: Mm-hmm

[00:43:15] Matt: with weekly or maybe monthly office hours around that particular cohort. So I’m kind of going a roundabout way to say I’m faced with this, this question, and this is a bigger question of, do I introduce new tiers of membership-

[00:43:30] Nathan: Yeah …

[00:43:30] Matt: revise current tiers, or continue to launch new products? And that’s kind of what I’m sitting with.

[00:43:37] And right now I’m thinking this craft track is almost like something between silver- Between yes, yeah … and gold, or maybe it’s beyond gold. I’m not sure. And maybe another tangent, I’m even wondering if, like, Writer’s Hour becomes its own product with its own tiers-

[00:43:51] Nathan: Mm …

[00:43:51] Matt: for people just looking for focused writing.

[00:43:53] And then membership, silver and gold almost become membership, and then there’s tiers within membership. So I don’t know if I’ve explained kind of my thought, but I’m-

[00:44:04] Nathan: Yeah …

[00:44:04] Matt: at once, there’s the question of new ideas, do I launch new products? And actually, our current membership, do I separate that into two products?

[00:44:11] Nathan: Yeah. ‘

[00:44:12] Matt: Cause I worry that the complexity and the unclear value proposition of each of these and the bigger membership might be a hindrance to our ability to, to scale and grow.

[00:44:22] Nathan: Yeah. So- These are all really good questions.

[00:44:24] Matt: Yeah.

[00:44:25] Nathan: And part of the reason why we saved products for number four, and we tackled funnels- Yeah

[00:44:29] as number two, ’cause o- once you instrument your funnel- Then you can start to see how changing and packaging and positioning and price-

[00:44:38] Matt: Mm …

[00:44:38] Nathan: affects conversion rates and the amount of money being brought in. There’s another element to the funnel that you can add in where you can talk about revenue at each stage of this.

[00:44:45] Matt: Mm.

[00:44:46] Nathan: Right? Because if we, you know, we’re tracking the total number of people and the conversion rate between each step, but that gives a … I- if you add in price and plan, that gives us the math to say, “Okay, this funnel was driving $2,000 in new MRR every week, and now it’s driving $4,000 in new MRR every week.”

[00:45:08] That could be because people are choosing a higher plan, because they’re- Mm … uh, converting at each of these thresholds at a higher rate, or because more people are coming through. So I say all of that because I believe that all of your product decisions should go through the lens of the funnel- Mm … and conversion rates.

[00:45:26] Because my gut instinct is that the more complexity you add, the … You’re gonna see your conversion rates decrease.

[00:45:33] Matt: Mm.

[00:45:34] Nathan: And you’re gonna see- Yes … referring a friend decrease, and you’re gonna see some of these other things as people are just like, “I don’t know what’s right for me.”

[00:45:42] Matt: Yes.

[00:45:42] Nathan: There’s a, an author named, uh, by the name of Dan Ariely-

[00:45:46] Matt: Mm

[00:45:46] Nathan: who has written a ton on pricing and psychology- Yes … and all of that.

[00:45:49] Matt: Yeah.

[00:45:50] Nathan: His stuff is fantastic. I would r- I would read that. But my gut instinct is I would not add- Okay … any more tiers or membership. Okay. I would think about how can I simplify?

[00:45:59] Matt: Yes.

[00:45:59] Nathan: And how can I make this decision as easy as possible?

[00:46:03] Yeah. One of my favorite pricing examples that I’ve ever seen was, uh, there was a software platform that had, I believe, three tiers, and it was like, uh, $15 a month, you know, 50, and then I think the most, the highest one was like 250 or something like that. Mm. And everyone was getting what they needed from the cheapest plan.

[00:46:23] And so that’s where- We’re feeling- … everybody went …

[00:46:25] Matt: we’re feeling some of that too, yeah.

[00:46:26] Nathan: Now, they’re targeting businesses.

[00:46:28] Matt: Mm.

[00:46:28] Nathan: So the only change they made, so they were getting like, say, 80% going to the $15 a month plan. They changed the name of that plan from, uh, starter or whatever it was- Mm … something positive, to hobbyist.

[00:46:39] Matt: Mm.

[00:46:40] Nathan: And a bunch of people went, “I’m not a hobbyist. I, I I work on a 12-person marketing team at a legitimate, you know, at a full business.” And so they just bought the business plan instead.

[00:46:48] Matt: Interesting, huh.

[00:46:49] Nathan: And so there’s a lot of things that you can play with- Yes … in that, where … And there might be packaging things, uh, wording, all of that- Yeah

[00:46:57] that says, “If you are this type of person-

[00:47:00] Matt: Yeah …

[00:47:01] Nathan: go here.” ‘Cause silver and gold don’t tell me anything.

[00:47:03] Matt: I know. It’s really … This is a, I’ve been … A bugaboo for me is, are these two titles.

[00:47:08] Nathan: So who-

[00:47:09] Matt: Yeah …

[00:47:10] Nathan: who should choose the gold plan?

[00:47:12] Matt: So kind of the way we describe it and think about it, Writer’s Hour, this is for focus.

[00:47:17] Mm-hmm. If you’re just looking for focused writing, that’s where you would go. That’s the Writer’s Hour held in community. Plus, we do monthly challenges. Yeah. So if it’s around focus, join that. If you’re looking for more craft support and community- Mm-hmm … you join Silver, ’cause that includes weekly interviews, a bunch of meetups happening at the mem- member-led meetups.

[00:47:35] This is for if you’re looking for coaching and accountability.

[00:47:38] Nathan: Mm-hmm.

[00:47:38] Matt: That’s the goal. So generally, it’s that escalating need state of seriousness- Mm-hmm … with a particular project or what you’re looking for. So- And

[00:47:45] Nathan: so there’s some aspect of that, of the, like, hobbyist to-

[00:47:50] Matt: Yeah …

[00:47:51] Nathan: like, sincere,

[00:47:52] Matt: right?

[00:47:53] Nathan: Yeah. And so you could even name them things like Focus-

[00:47:56] Matt: Yeah

[00:47:56] Nathan: Community, Coaching.

[00:47:58] Matt: Yeah.

[00:47:59] Nathan: Right? Or-

[00:48:00] Matt: Commitment or con- con- something. Mm. I’m not trying to do, like, a bunch of Cs, but that could be- Yeah … interesting, too. But yeah, Focus, Community. And actually, this other one I’m potentially wanting to introduce is something around craft. But then, uh,

[00:48:14] Nathan: coaching. And I’d be careful with the word craft- Yeah

[00:48:16] because it doesn’t actually mean anything. And I say that w- as per- someone who runs a conference- Yeah … called Craft and Commerce. So I, I love the word. I use it-

[00:48:22] Matt: Right …

[00:48:23] Nathan: and all of that. But it doesn’t help me decide, am I the right person-

[00:48:26] Matt: Right …

[00:48:27] Nathan: uh, to jump into one of these others. Mm-hmm. I bring all this up just because, uh, the products and the product mix is really, really important.

[00:48:35] Matt: Mm.

[00:48:35] Nathan: It’s a big leverage point, um, that you’re gonna wanna play with and you’re gonna wa- wanna look at. And then you’re gonna wanna look at how every change in that changed your funnel metrics.

[00:48:46] Matt: Mm-hmm.

[00:48:47] Nathan: And ultimately changed the retention.

[00:48:48] Matt: Right.

[00:48:49] Nathan: Right? Because does someone identify with, “I’m on the right plan for me”?

[00:48:53] Uh, Seth Godin has this line where he says, like, “People like us do things like this.”

[00:48:57] Matt: Yes,

[00:48:58] Nathan: yes. Right? It’s an identity thing.

[00:48:59] Matt: Mm.

[00:48:59] Nathan: And so I show up and it’s like, “Hey, um, where do people like me go?”

[00:49:03] Matt: Yes. They’re

[00:49:03] Nathan: like, “Oh. Well, tell me about yourself,” and like, “Here’s a few things.” “People like you go to the gold plan.”

[00:49:08] Yes. And you’re like, “Great. Thank you. Thanks for letting me know.” You know, ’cause you know that I’m new here feeling where you’re like, “Shoot, where do I need to go?”

[00:49:15] Matt: Yeah. Like,

[00:49:16] Nathan: just, just tell me.

[00:49:17] Matt: That’s it. Yeah.

[00:49:18] Nathan: Uh, and, and it might be the stage that they’re at, how serious they are.

[00:49:22] Matt: Mm.

[00:49:22] Nathan: Any of those things.

[00:49:23] Matt: Mm-hmm.

[00:49:24] Nathan: Yeah. Or, like, I, I like accountability as a word. Right. ‘Cause you might even, as you describe the details within this- Mm-hmm … right, accountability might be- Yes … the word. That really is,

[00:49:33] Matt: yeah.

[00:49:34] Nathan: If, if you are on deadline-

[00:49:35] Matt: Mm-hmm …

[00:49:36] Nathan: you have to be in the residency. If you’re serious you know. I guess you’d go through all the traits-

[00:49:42] Matt: Yeah

[00:49:42] Nathan: of the writer.

[00:49:43] Matt: Yeah.

[00:49:43] Nathan: What stages could you be at, all of that.

[00:49:45] Matt: Yeah.

[00:49:46] Nathan: And then, then you identify and, like, map those to each plan.

[00:49:49] Matt: Right.

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[00:50:15] Matt: I’m also curious your perspective, because this, so this was an additional product.

[00:50:19] Mm-hmm. So we kinda kept this product what it was- Yeah … and then we added this additional product.

[00:50:24] Nathan: With the residency.

[00:50:25] Matt: Yeah. And I guess I’m curious your decision point of when does something become a separate product.

[00:50:33] Nathan: Yeah. ‘

[00:50:34] Matt: Cause this, we always want members to feel, uh, that they’re valued, so everyone gets a discount on this.

[00:50:40] So it’s almost like this is the ticket to the, the venue. Mm-hmm. And then we have this thing. So I am questioning, there are some other products I can imagine us launching that once they’re in here, it’s… Okay. Yeah. What, what’s your real need state?

[00:50:54] Nathan: I think

[00:50:55] Matt: the- And I’m curious how you approach that … the

[00:50:56] Nathan: way to think about it is, first, is there a core job to be done that’s not, like, that’s really, really important, a lot of people share, and is not being served- Yeah

[00:51:05] in our current stack. And I think that’s what the residency does.

[00:51:07] Matt: Yes.

[00:51:08] Nathan: And it makes sense as a separate product because it’s time-bound. Mm-hmm. It’s a high price, all of that. The other question that I ask is- How close to the ceiling are we on these products?

[00:51:20] Matt: Mm-hmm.

[00:51:21] Nathan: Right? W- you might say, like, “Look, you know, we’ve saturated our market, and so we’re really only gonna be able to bring in another few hundred members.

[00:51:30] Like, that’s never gonna gr- grow. We’ve optimized every other part of the business. It’s time to add additional services, and that’s why we’re starting a publishing company. That’s why we’re doing,” you know, whatever other things you might do. When I look at your business, I see it as there’s a ton of potential to optimize all of these different levers.

[00:51:48] And so I believe it would be a distraction to add more products-

[00:51:51] Matt: Mm-hmm …

[00:51:51] Nathan: at, at this point in time. Yeah. Because you’re probably at, like, 25% optimization in, like, 10 different places.

[00:51:59] Matt: Mm.

[00:52:00] Nathan: And you would just add a whole new surface area that now you have to optimize, which w- which would just slow you down.

[00:52:05] Matt: Right. Mm. Mm.

[00:52:07] Nathan: I would say 9 times out of 10, when you’re looking to improve something in a business, you’re better off improving what you have rather than starting something new.

[00:52:15] Matt: Mm.

[00:52:16] Nathan: Uh-

[00:52:17] Matt: Got it. Which is- Can I ask one more question about that? Do it. So this concept of, I know we don’t like the word craft- Yeah

[00:52:24] but bringing a group of people together around, like, fiction writing or indie publishing or something- We could, the easy option is just to add that here. So we’re basically ballooning out what’s in there.

[00:52:37] Nathan: Yep.

[00:52:37] Matt: But I do think it’s, we’ll be leaving value on the table by just including that, which I think will be a higher glove service, not quite like this, but around making the community feel a little more intimate.

[00:52:51] Nathan: Mm-hmm.

[00:52:52] Matt: But also giving them the support they need.

[00:52:55] Nathan: Mm.

[00:52:55] Matt: So kind of holding that as well, ’cause I don’t wanna undervalue this by throwing a bunch more stuff in. Actually- For, for sure … it feels more confusing.

[00:53:04] Nathan: Yeah, and we’ve found that we’ve added stuff to it- Yeah … and people were happy paying for, like, a premium plan.

[00:53:08] Yeah. And we added even more value to it at the same price, and they’re like, “Well, I don’t need those things.” Yes. “So can I just pay a la carte for the things that I needed?” And you’re like, “No.”

[00:53:17] Matt: Yeah, yeah.

[00:53:17] Nathan: You know? But the additional value is, can sometimes, uh, decrease the perceived value.

[00:53:22] Matt: Right.

[00:53:23] Nathan: So what I would do there- We

[00:53:23] Matt: see that a lot, actually.

[00:53:24] Yeah.

[00:53:25] Nathan: Yeah, and so often it’s stripping things away and, or even just ’cause something’s offered doesn’t mean you have to talk about it on the sales page.

[00:53:31] Matt: Mm,

[00:53:31] Nathan: right. Right? And so you can AB test, you can do these things- Mm … like, ooh, if I don’t talk about this, does it perform better?

[00:53:36] Matt: Right. ‘

[00:53:36] Nathan: Cause maybe-

[00:53:37] Matt: Mm

[00:53:37] Nathan: partway down the funnel, maybe someone signs up for Silver, and it always included this additional thing. Mm. But you didn’t talk about it, and then maybe in the trial y- you have an email like, “Hey, if you- Mm … convert this trial- Right … we’ll add in this other thing for free.” Right. Right. And they’re like, “Oh, that’s amazing.

[00:53:52] I would love that.”

[00:53:52] Matt: Right.

[00:53:53] Nathan: Even though before- Interesting … you were just giving it away.

[00:53:55] Matt: Yeah.

[00:53:55] Nathan: But I would say a traditional membership is probably gonna sit at about 10% monthly churn.

[00:54:00] Matt: Mm.

[00:54:01] Nathan: And it’s insanely hard to scale that, right? That is, like, I don’t know, swimming with ankle weights or something. Mm-hmm.

[00:54:06] So if you had said that your, uh, churn was that high, then the first thing that I would be going to is like, okay, how can we get more clear value and more commitment from each member? And what I would be doing is I would say, “Hey, we’re gonna alter it, ha- have a different version of the Silver package.”

[00:54:22] Matt: Mm.

[00:54:22] Nathan: “And instead of $49 a month, it’s $499 for the year.” And what it does is we’re going to put you into this accelerator.

[00:54:31] Matt: Mm.

[00:54:31] Nathan: And we’re going to put you into cohorts based on, you know, fiction- Mm … or indie publishing. And with that-

[00:54:38] Matt: Got

[00:54:38] Nathan: it.

[00:54:39] Matt: Mm. Uh,

[00:54:40] Nathan: and, and the crazy thing is, not only are we doing all this for you, but it includes a full year of our silver membership.

[00:54:45] Matt: Mm.

[00:54:46] Nathan: And all you did is you created this one-time event-

[00:54:49] Matt: Yes …

[00:54:50] Nathan: that they get a lot of value. And I say one time, it could be quarterly, it could be monthly. Mm. Right? But it, it gives you an open and close launch. It moves them from like, “Oh, I’ll try it out at $49 a month, then I’ll probably cancel after three months-

[00:55:02] Matt: Mm

[00:55:02] Nathan: uh, and I’ll move on,” into this like, “Oh, I’m committed.”

[00:55:06] Matt: Yes.

[00:55:06] Nathan: So we’ve done this with Kit, where, you know, instead of selling a-

[00:55:09] Matt: Mm …

[00:55:10] Nathan: $30 or $50 a month, um, subscription, we’ve done an accelerator, and it’s like all this, and it includes.

[00:55:16] Matt: Mm.

[00:55:17] Nathan: This thing. But really all we did was really focus on making you successful in this first period of time, and then we f- at, we threw in a year free of the software, but it was all the same price.

[00:55:27] Matt: Got it. That’s really smart, ’cause you were able to then position to the value state and the value proposition that I’m talking about here.

[00:55:35] Nathan: Yep.

[00:55:35] Matt: But in this, it’d be just framed in a one-time annual- You didn’t, you didn’t go

[00:55:39] Nathan: make a new product …

[00:55:40] Matt: point of… Yeah, that’s really-

[00:55:41] Nathan: And so you didn’t clutter.

[00:55:42] Matt: Yeah, ’cause we are thinking of launching this in 2027.

[00:55:45] Mm-hmm. So actually starting the year, there’s an extra level of commitment there. We have this… Yeah, I really like this.

[00:55:51] Nathan: One other thing that you’re gonna need to look at on retention is this number, the 3 to 5%, is for the entire, for all 2,000 members.

[00:56:01] Matt: Mm.

[00:56:01] Nathan: So it is averaging the person who signed up last week and is like, “I don’t know that you guys are any good”-

[00:56:08] Matt: Yeah

[00:56:08] Nathan: with the person who said, “Man, I have been a member for three years. This is the best thing that’s ever happened.”

[00:56:13] Matt: Mm.

[00:56:14] Nathan: So from a cohort perspective, you need to split it out, not just based on where they came from-

[00:56:18] Matt: Mm …

[00:56:19] Nathan: but based on time.

[00:56:20] Matt: Mm.

[00:56:20] Nathan: And so I would measure a 30-day churn.

[00:56:22] Matt: Mm.

[00:56:23] Nathan: And so we do this at Kit. We are obsessed over if you pay us, you know, you become a member, um, how likely are you to still be a member- Yeah

[00:56:34] 30 days later? ‘Cause that churn rate for us is 18%.

[00:56:37] Matt: Mm.

[00:56:38] Nathan: Right? So that’s really, really high. It, whereas the average is 3 1/2%. So once you’re diluted into the big pool, it’s only 3 1/2%. Right. But if you said, “Oh, if I get this new customer in, they’re going to retain for this long period of time,” it’s like, no, they’re not.

[00:56:52] Matt: Yeah.

[00:56:52] Nathan: You’re using the numbers from the long-tenured people- To convince yourself that this person’s gonna stay at that retention level

[00:56:58] Matt: And we’ve, we’ve seen that. We say if someone crosses, and I think for us it’s something between 30 and 90 days. Mm-hmm. Once they cross that threshold, they’re, they’re with us for years.

[00:57:06] Nathan: Yeah.

[00:57:07] Matt: So, yeah.

[00:57:08] Nathan: And then you can say like, okay, you know, in our case, right? Yeah. We have a team. They’re like, “All right, how do we get this 18% number down to 15%?”

[00:57:16] Matt: Yeah.

[00:57:16] Nathan: They’re thinking of every touch point. Okay, what actions do you take? Okay, if you send a broadcast, if you import these subscribers- Mm … you know, how can we obsess over that?

[00:57:24] Matt: Mm.

[00:57:24] Nathan: You know, just because someone paid doesn’t mean they’re hooked. Right. And so how do we make that, that transition?

[00:57:29] Matt: That, that resonates.

[00:57:31] Nathan: Okay. The reason that we’re going in this, you know, we wrote it top to bottom.

[00:57:36] Matt: Yeah.

[00:57:36] Nathan: You could also write these the opposite way. You could think of it as, like, the foundation for a building.

[00:57:41] Matt: Mm.

[00:57:42] Nathan: The most important thing is our mission and vision.

[00:57:44] Matt: Mm-hmm.

[00:57:44] Nathan: Why are we doing what we’re doing? Second, if we don’t have a funnel, we don’t have customers coming in, we don’t have awareness, we don’t have a business. And so, you know, that’s our next level.

[00:57:53] Matt: Mm.

[00:57:54] Nathan: If we’re not keeping our customers, we don’t have retention, then something’s wrong with our product, uh, you know, and every bit of effort that we put in is going to be, uh, diluted, you know, and going out to leak- leaky bucket.

[00:58:07] Then the next part is the products. You know, what are we actually selling? How do we maximize the revenue per customer? And then the final part is, is this ready to scale?

[00:58:17] Matt: Mm.

[00:58:17] Nathan: And so I wanna talk through a few metrics that are really, really important to scale- Any recurring revenue business, whether it’s a membership or a SAS company.

[00:58:28] So there is a metric, uh, that is LTV to CAC.

[00:58:34] Matt: Mm.

[00:58:34] Nathan: And so I’ll just write that out, uh, and then we’ll describe what it is. All right, so LTV is lifetime value, and CAC is customer acquisition cost. So if we’re to … Let’s just focus on lifetime value for a moment. You can convert any percentage churn into a, a number of months or years that someone stays.

[00:58:55] So what you would do is you would, uh, say one divided by 3.5% will get you, I don’t know the math, it’s, like, 22 months or 24 months, something like that. Mm-hmm. And so on average, someone is going to stay at 3.5% for, you know, say right around two years. And then if you multiply that by your average revenue per customer, you could determine a lifetime value for each one of these plans.

[00:59:19] Matt: Mm.

[00:59:20] Nathan: Now, you have to keep in mind, it’s gonna be skewed because your longtime customers that are never gonna churn ’cause they love you are gonna be driving up that number, and the immediate customers who are skeptical-

[00:59:31] Matt: Mm …

[00:59:31] Nathan: and aren’t hooked yet, they’re gonna be driving it down.

[00:59:33] Matt: Mm. Right.

[00:59:34] Nathan: So you gotta kinda balance that.

[00:59:36] But that gets you to a number of what’s a customer worth to me? Okay, so with some quick math with the, the help of our producers, uh, a 3.5% monthly revenue churn means someone’s gonna stay on average for 28 months, and then at $16, we are at $457 in- Mm … average in, in LTV. Mm. Right?

[00:59:56] Matt: Mm.

[00:59:56] Nathan: And you can do that math for each one of your plans- Mm

[00:59:58] right? ‘Cause they’re each gonna have a different churn rate. Right. And they have a different price point.

[01:00:02] Matt: Right.

[01:00:02] Nathan: And then you can get to a blended lifetime value. So now we get into customer acquisition cost. How much money can you spend to acquire a customer?

[01:00:12] Matt: Mm.

[01:00:13] Nathan: Um, if we think about ratios between this, uh, I would say four to one is kind of the, the minimum ratio.

[01:00:23] So let’s say, so in this- Mm … in this scenario, I would be happy to spend $100 to acquire a customer to the Writer’s Hour.

[01:00:31] Matt: Mm. Mm.

[01:00:32] Nathan: Now, if you’ve spent tons of money all upfront, and you don’t make it back for, oh, you know, you make it back over the course of 28 months- Right … you could go broke-

[01:00:42] Matt: Right …

[01:00:42] Nathan: if you did this.

[01:00:43] Right. Like, right, you have to manage cashflow

[01:00:44] Matt: and-

[01:00:45] Nathan: Mm. Hmm … um, e-commerce brands really struggle with this- Mm … because they have, like, supply chain and, you know, the- Yeah … and all of this. But-

[01:00:53] Matt: Huh …

[01:00:54] Nathan: that CAC-to-LTV ratio, um, is really important. If you can stay above four, like at Kit, we try to target 4.5.

[01:01:03] Matt: Mm.

[01:01:03] Nathan: Um, which is actually what this is exactly.

[01:01:06] Anything under 3.5, we start to get really nervous.

[01:01:09] Matt: Mm. ‘

[01:01:10] Nathan: Cause we’re a bootstrap company, we wanna grow profit- Yeah … profitably. Anything before, we’re like, “Okay, cool.” Above 4.5, we’re like, “Okay, we should be spending more aggressively to grow.” So this is like the final number that matters in any recurring business, because every other number plays into this.

[01:01:27] Matt: Mm.

[01:01:28] Nathan: So if you think about, okay, if I can increase my conversion rate … Sorry, if I can increase my retention from, um, 3.5 to 3, as I increase, uh, decrease my churn, right?

[01:01:41] Matt: Mm.

[01:01:42] Nathan: Then that is gonna take me from the 28 months to whatever it is, 30-something months of retention, which means a customer is worth way more to me.

[01:01:50] Matt: Mm.

[01:01:50] Nathan: If I can dive into my product stack and I can say, “Ooh, what would have to be true for 5 or 10% more people to be on this plan, on the silver plan versus the writer’s hour plan?” Well, now my average revenue per user is way higher, which drives my LTV way higher. Mm. Right? And then if you’re like, okay, on the customer acquisition, acquisition cost- If I can get my Facebook ads dialed in a little better, or I can have a mechanism where every member refers another member, that drives down my CAC.

[01:02:23] Matt: Mm.

[01:02:23] Nathan: Which means I can probably … I can scale more and all of that. So there’s like, there’s so much that goes into this. Mm. But I wanna show how, like, we have to get all of the fundamentals first- Yeah … before we can obsess over- Mm … this final equation.

[01:02:38] Matt: Yeah. There’s a whole world here.

[01:02:39] Nathan: Yes.

[01:02:40] Matt: Yeah. No, it’s- I’m very

[01:02:42] Nathan: curious for your thoughts and reactions.

[01:02:44] Matt: Yeah. I think, um, so I’ll just say the kind of the in- an uninformed perspective of this is I’m just gonna throw some ads out and- Yeah … like see what happens, you know? It’s like, “Oh, cool. We had 100 people sign up.” But without this metric, without actually- Mm … looking at what that means, it’s just sunk money at, at-

[01:03:03] Nathan: Yeah

[01:03:04] Matt: at worst. Um, or at best, really. Um, yeah. So I’m, I’m … This is, this framing is really helpful that we’ve started here. Uh, yeah, I’m kind of, like, excited to figure this out though, you know? That’s … Simultaneously.

[01:03:18] Nathan: Yeah. And so you’ll, you’ll look at it for every plan, and you’ll be like, “Okay.” Yeah. “If someone is on this plan, then they’re worth, you know, this huge amount of money.”

[01:03:27] Right. And so maybe it’s … You know, we’ve done it … We’re realizing like, oh, we could justify sending this, uh, Swagger merch- Yeah … to every person on this plan.

[01:03:36] Matt: Right.

[01:03:37] Nathan: You know? Uh, ’cause that might help increase their retention. It might make them feel more of a community. Yes. You know, all of those things. And, and you’re like, “Ooh.

[01:03:44] Well, I only made $50 off this user, and so if I spend $50 to send them stuff,” like, that’s a problem. You’re like, “Oh, wait, but if they stay for 28 or 36 months-” Right “… then, you know, like on the silver plan.” And we calculated it for the Writer Hour plan. Right. But it, it would be, you know, could- Mm … potentially be way higher.

[01:04:01] Matt: Hm. Lots to think about. Yeah. I’ll, I’ll, uh, I’ll feel like I need to come back in a year and, like- Yeah … all right, let’s, like, dive into that more specifically. So how, how would I calculate customer acquisition cost? What, what is that and-

[01:04:13] Nathan: Yeah … where do I start? So there’s a lo- like, there’s a lot of nuance to it, but to dive in, quite simply, it’s, uh, everything you spend on marketing.

[01:04:20] So that’s gonna be your ads, uh, your team. Mm. And you might … Someone’s time might be split 50/50 between marketing and community support or something else. Right. But it’s what you c- spend to bring in a customer divided by how many new customers you had come in. So in this case, it’s really important to know, like, the, the metrics in your funnel, ’cause it’s, it’s how many new members came in each month.

[01:04:43] And then you’re going to be like, “Okay. So on average, uh, you know, I spent $10,000 on marketing. I got, um, 1,000 customers. And so then- Hm … my CAC was 100 bucks.”

[01:04:54] Matt: Hm. It’s really helpful because it makes things like social media- Mm-hmm … and podcast instead of, okay, we pay an editor for this, we pay someone to do this.

[01:05:04] It’s actually, it’s in the context of that’s all awareness, that’s all marketing.

[01:05:09] Nathan: Yes.

[01:05:09] Matt: So anyway, it’s, it’s… We’ve ne- I’ve never had a good reason to say this is worth spending or not worth spending before, but having a number here related to this then-

[01:05:18] Nathan: And that’s where

[01:05:19] Matt: when you- … gives a lot more context

[01:05:19] when

[01:05:19] Nathan: you have, there’s more that you have to factor into it-

[01:05:22] Matt: Yeah …

[01:05:22] Nathan: of like what’s your gross margin? What do you actually have to spend to service each customer? Mm-hmm. And there’s a lot more details, and you can get into all kinds of debate of what gets included in CAC and what doesn’t. Right. But at the high level, if you pick a way to measure it, and you start measuring it, and then you say, “Hey, what’s my target?”

[01:05:38] You know, my target is above four. And you’re like, “Cool. At that number, I feel good ramping it up.”

[01:05:43] Matt: Mm.

[01:05:43] Nathan: When it starts to dip below that, then I start digging and say, “Okay, how could I, how could I decrease this?”

[01:05:48] Matt: Mm.

[01:05:49] Nathan: The other thing is- Uh, things like team members tend to scale across a lot of customers. You’re paying the same person to run Facebook ads if they’re bringing in 500 customers a month versus 5,000 customers a month.

[01:06:04] Mm. And so their salary at the 500 is a very big part of your CAC, where it’s a relatively small part of your CAC at the-

[01:06:11] Matt: Mm …

[01:06:11] Nathan: at scale.

[01:06:12] Matt: Mm-hmm.

[01:06:12] Nathan: All right. So Matt, we’ve covered a lot in the last hour. You’ve been drinking from the fire hose- … of all of the metrics and everything else.

[01:06:18] Matt: Yeah.

[01:06:18] Nathan: I wanna, like, just take a step back and say, like, what questions you have, any reactions or takeaways?

[01:06:24] Matt: So there’s three core actions that are sitting at the top of my mind. Number one is, I love what you said about the KPI around mission and vision- Mm … and constantly repeating that in every event, every interaction I have, keeping that top of mind. So that, that’s the first one that I think will… That, that foundation for everything.

[01:06:44] The next is the conversation. There’s a lot to think about around our three tiers of membership, the naming of it, this potential annual kind of, uh, invitation offer that we talked about, that I really want to get clear about that. I think that’s an important step. And then finally, all of these things like funnel and retention, it, it makes me realize how important the granular, granular numbers are.

[01:07:09] Mm-hmm. So I need to get clear on what those numbers are, start to track them, identify them. Um, yeah. So those are kind of like the three big points for me, and I think everything else, I’m gonna have to marinate on a lot of this and talk to the team. But- Yeah … yeah, those are the kind of the three.

[01:07:24] Nathan: I love it.

[01:07:25] But I’m go- The good, the good news is this is recorded.

[01:07:27] Matt: Yeah.

[01:07:27] Nathan: Thank God. So you can

[01:07:28] Matt: watch,

[01:07:28] Nathan: watch it back at any time. Uh, I mean, you’ve built a really impressive business. Like to get to this- Thanks, man … size and scale is really hard. To get to this level of retention shows that you’re having a huge impact- Mm

[01:07:39] on the writers that you serve. And I’m just excited for you … to see you take this to so many more writers because I know the long-term impact that you’ll have on the writers and the writers will have on their readers.

[01:07:51] Matt: Mm-hmm.

[01:07:51] Nathan: And I would just keep recentering everyone on that because you’re doing really important work.

[01:07:56] Matt: Yeah. I, I appreciate it. I mean, really, this has been amazing. Just, like, spending time together talking about this, geeking out on this has been incredible. I really appreciate it. And yeah, just, just so much gratitude-

[01:08:07] Nathan: Oh, for sure …

[01:08:07] Matt: for, for you. Yeah.

[01:08:08] Nathan: I’m happy to. All right. So I’m a writer. You’re a writer. Yeah.

[01:08:12] We both deeply believe in the importance of building a daily writing practice- Mm … and not outsourcing our thinking, uh, to AI, but actually, like, implementing it ourselves and keeping that muscle sharp. If someone wants to… They’re hearing this, and they’re like, “I love scaling memberships, but-” I want to do this.

[01:08:28] Hmm. I wanna have a daily writing practice. Yeah. Where should they go to join your comput- community and, you know, be one of these 20,000 members?

[01:08:34] Matt: Yeah, so they can go to londonwriterssalon.com and find out all of the details around the membership. Um, and really encourage everyone to join us for Writers Hour.

[01:08:43] We get up to 1,000 writers every day writing together in silence, whether they’re journaling or writing poems or writing novels or nonfiction books. Um, it’s a really great community, and it’s just … You get to be, have colleagues that you- Yeah … wish you had in the writing practice. So we’d love … The more the merrier.

[01:08:59] Come, come write with us.

[01:09:00] Nathan: I love it.

[01:09:01] Matt: Yeah. Thanks so

[01:09:01] Nathan: much for coming on.

[01:09:02] Matt: Yeah. Appreciate it, Nathan. Thank you.

[01:09:03] Nathan: If you wanna break through the million dollar ceiling, check out episode 85 with Tim Grall. Tim broke out of a three-year plateau and scaled his education company from 700,000 to over $2 million a year by rebuilding his business model and team.

[01:09:17] I think you’re gonna get a lot out of that one. Like the video if you enjoyed it. Hit subscribe on YouTube or wherever you’re listening, and I’ll see you next week

[00:00:00] Chenell: I sent that first edition out to three people. Within 10 months, I had 21,000 subscribers.

[00:00:04] Nathan: Chenell Basilio reverse engineers how the biggest newsletters grow.

[00:00:08] Chenell: That’s out of thousands of subscribers to our email list. And that’s

[00:00:11] Nathan: so easy to do.

[00:00:12] Chenell: So you’re not creating anything net new.

[00:00:14] Nathan: Her work has been featured by The Hustle, Buffer, Creator Science, and more.

[00:00:18] Chenell: With newsletter growth, people only focus on one thing- Okay … which is growth tactics, but they miss the other four.

[00:00:23] Nathan: So what are those five things? Can we dive in with number one?

[00:00:26] Chenell: Insanely valuable content. This is the most important thing. All of these other things don’t matter as much if you don’t get this first one right.

[00:00:32] Number two is positioning.

[00:00:34] Nathan: Okay.

[00:00:34] Chenell: Number three is building momentum or distribution.

[00:00:37] Nathan: What is number four?

[00:00:38] Chenell: Conversion.

[00:00:39] Nathan: We made it all the way through the list. What is the fifth lever?

[00:00:41] Chenell: This is the one that I see no one doing.

[00:00:44] Nathan: Okay.

[00:00:45] Chenell: It’s .

[00:00:46] Nathan: Okay.

[00:00:47] Chenell: Examples of this.

[00:00:48] Nathan: If you say my newsletter, I’m gonna cry. I’m just kidding.

[00:00:50] We’ll get into that later. As the founder of an email marketing platform, you’d think if anyone would have their newsletter dialed in, it’d be me. But Chanel breaks down a bunch of things that even I could be doing better.

[00:01:00] Chenell: I have the actual- Do it … what it says on your-

[00:01:03] Nathan: Oh, boy …

[00:01:03] Chenell: website right now.

[00:01:04] Nathan: I’m nervous.

[00:01:06] Kara’s nervous. I’m nervous. Calum’s nervous.

[00:01:08] Chenell: Current headline on your site says, “Hello, I’m Nathan Barry.” That’s- Pretty bad. Like- That should be what you lead with.

[00:01:17] Nathan: Oh, wow. It’s a total newsletter growth masterclass. Okay, you wanna go to subscriber experience?

[00:01:22] Chenell: Do you?

[00:01:25] Nathan: Oh, here we go.

[00:01:30] Janelle, thanks so much for coming on.

[00:01:32] Chenell: Thanks for having me.

[00:01:33] Nathan: We’ve got Newsletter Growth Masterclass written up here. Yes. What are we gonna learn over the next 60 minutes or so?

[00:01:37] Chenell: Yeah, so with newsletter growth, I feel like people only focus on one thing, which

[00:01:41] Nathan: is- Okay …

[00:01:41] Chenell: growth tactics. Mm-hmm. Social media, tools, tactics, strategies, all those things, but they miss the other four.

[00:01:48] Nathan: Okay. So we’ve got five written out here. Yeah. So we’re gonna cover all of them.

[00:01:51] Chenell: Yes.

[00:01:51] Nathan: Do you think afterwards we can apply some of this to my newsletter?

[00:01:54] Chenell: Absolutely.

[00:01:55] Nathan: Okay. I think that’ll be good. And then if we have some time, we’ll dive in on monetization and some of these other categories as well.

[00:02:02] Chenell: Totally.

[00:02:02] Sounds good.

[00:02:03] Nathan: All right, so before we dive in, I feel like you came onto the scene in the newsletter space very, very quickly, doing these deep dives and breaking down, through Growth in Reverse- Mm-hmm … like, exactly how newsletters grow. And so you and I have kind of a similar seat in the greater economy of, like, s- looking and studying behind the scenes what works across, you know, hundreds of newsletters.

[00:02:23] Chenell: Yeah.

[00:02:23] Nathan: What’s been your experience of growing your own newsletter and, like, diving into this whole world?

[00:02:28] Chenell: I went way too deep into it at first. So, um, I was previously running Facebook and Google ads for clients-

[00:02:34] Nathan: Mm-hmm …

[00:02:34] Chenell: and burned myself out pretty hard and decided, like, I needed something different. And I was on Twitter one day, and I found this guy named Mario Gavelli.

[00:02:42] Nathan: Mm.

[00:02:42] Chenell: And you had previously interviewed him.

[00:02:44] Nathan: Yeah.

[00:02:45] Chenell: Uh, Mario- The

[00:02:46] Nathan: Generalist …

[00:02:46] Chenell: The Generalist. His newsletter. Yes. He built his newsletter up. Was making 300 grand in his first year as a solo creator just writing this newsletter, and I was like, “How did you do that?” So I spent probably 60 hours researching his story, going through all the past episodes of podcasts he was on, going back through his Twitter archive and everything, and I put together this, like, 3 to 4,000 word article with screenshots and tweets of all the things he did and just showcased, like, here were the four growth levers that got him to 50,000 subscribers or more.

[00:03:16] And I wrote this deep dive, and I was like, “Maybe I should make this a newsletter.” So I sent that first edition out to three people.

[00:03:23] Nathan: Okay.

[00:03:24] Chenell: And then within 10 months, I had 21,000 subscribers just from- Wow … continuing to write these deep dives every week.

[00:03:29] Nathan: I think something that stands out is going a level above and beyond what everyone else is willing to do.

[00:03:34] Chenell: Yeah.

[00:03:34] Nathan: I actually went back to some o- of my early content ’cause people would say, like, “Oh, Nathan, when you started writing content, um, you know, you were writing much longer content than other people were, and you included a bunch of real numbers.” Mm-hmm. “And that made it stand out.” I went back and looked at it, and I was like, long back then was like 1,000 words.

[00:03:50] You know, I was like, “These aren’t nearly as long as I remember them to- being.” But putting in real numbers made a huge difference.

[00:03:55] Chenell: Yeah.

[00:03:56] Nathan: And so I feel like, in your case, taking this, like, research, analytical mind where you’re like, “I wanted to know this anyway-

[00:04:01] Chenell: Yeah …

[00:04:02] Nathan: so why don’t I distill it for everyone else?”

[00:04:04] And being willing to go deep- stands out in a huge way. And so it’s the same idea of, like, what David Sendrow does with founders or, uh, the Acquired Podcast was another thing of, like, no, we’re … This is not dumbed down. This is, this is for the person who wants to completely nerd out.

[00:04:18] Chenell: Yeah.

[00:04:19] Nathan: And the level of quality is far beyond what anyone else does.

[00:04:21] Chenell: Totally. Everyone thought I was insane because I would spend 40 to 50 hours a week just researching and writing these deep dives.

[00:04:27] Nathan: Yeah.

[00:04:28] Chenell: But it stood out, and that’s what made it grow so fast.

[00:04:30] Nathan: And so as a result, you’ve learned what works. Mm-hmm. What the, the five key levers are- Yeah … in the process. So should we dive in with number one?

[00:04:39] Chenell: Sure.

[00:04:39] Nathan: Yeah.

[00:04:40] Chenell: Okay. Kind of a great segue because it’s about content.

[00:04:43] Nathan: Okay.

[00:04:43] Chenell: And more specifically, insanely valuable content.

[00:04:45] Nathan: Insanely valuable content. All right.

[00:04:47] Chenell: Insanely valuable content is the stuff where people are just like, they can’t help but share it with friends, other people in their, in their space.

[00:04:54] Instead of just like, “Hey, I’m gonna put out this piece of content that’s, like, mediocre.” Mm-hmm. Like, no, no. Let me go super deep or give you the most value that I can.

[00:05:01] Nathan: I think the phrase that I hear people say around this is something like, you know, if you put it in quotes, “I can’t believe it’s free.”

[00:05:10] Chenell: Yes.

[00:05:11] Nathan: And you know, we’ve heard other content creators talk about this of, like, “I want my free content to be better than everyone else’s paid content.”

[00:05:17] Chenell: Yeah.

[00:05:18] Nathan: And if you do that, then you’re going to get a level of things spreading and sharing and sort of- that sort of thing. I remember when you dropped a, a Growth in Reverse issue about Sahil Bloom.

[00:05:30] Chenell: Mm.

[00:05:31] Nathan: Right? It was interesting because he was probably being talked about all the time- Yeah … ’cause he was such a prolific creator growing so fast. And so it was a timely piece, but also it was so detailed that people were like, “Oh, this is the kind of thing that I would pay for. I can’t believe it’s free.”

[00:05:44] Chenell: Right.

[00:05:45] Nathan: And so it ended up getting shared a ton and getting you a whole bunch of growth.

[00:05:49] Chenell: Yeah. It’s in. Um, it’s really cool when you, when the creators that I am studying, I don’t tell them that I’ve- Mm-hmm … created these things. They just, like, randomly find them, or a friend will share it with them.

[00:05:58] Nathan: Okay.

[00:05:58] Chenell: And so that’s always fun to have them come back and be like, “This is actually the most detailed thing about my growth.

[00:06:02] Like, thanks. I didn’t even know that I did this thing.” So those are fun.

[00:06:07] Nathan: I love that. I think when, um, Cannon Myers did a breakdown for James Clear, one of the things that he said is he was like, “Oh, that is smart. We just kinda started doing it ’cause it sounded like a good idea.”

[00:06:17] Chenell: It’s like this wasn’t strategic.

[00:06:19] Yeah. It just happened.

[00:06:20] Nathan: Yep, that makes sense. So what goes into insanely valuable content?

[00:06:24] Chenell: Yeah. So there are six ways that- Okay … I’ve seen people make something insanely valuable.

[00:06:28] Nathan: Mm-hmm.

[00:06:28] Chenell: Um, the first one- I’m gonna jump over

[00:06:30] Nathan: here

[00:06:30] Chenell: and- Yeah, yeah. Go

[00:06:30] Nathan: for it … and we’ll, we’ll do a, uh, tactic and then go detailed- Sure

[00:06:34] right here.

[00:06:35] Chenell: So the first one is help someone make money. I feel like a lot of people are trying to do that these days, but it doesn’t have to be bro-y. Make money, save money is another one. Okay. And then save time. So you’re doing the research to save them 40 hours of studying this newsletter for them.

[00:06:51] Nathan: Yep.

[00:06:51] Chenell: Um, make money, save money, save time. Teach them something, giving them a framework or that kind of thing. Uh, entertain them. Make them laugh, smile.

[00:07:00] Nathan: Yeah.

[00:07:00] Chenell: Which is really important, and I think a lot of people try and skip that one. But, um, and then the last one is speed to market or- Mm … timely content. And so the key with insanely valuable content is you don’t need to try and have all of these in there, but if you can combine two or more, that is where it ends up.

[00:07:15] That’s the sweet spot for this stuff. Mm. And so for an example, um, I write deep dives. It doesn’t have to be a deep dive. And I think when I say insanely valuable, people are like, “Oh, it’s gotta be this super intense thing.” Justin Moore- Yeah … Creator Wizard, uh, he puts out a newsletter. He’s helping people get sponsorships, like creators get brand deals and sponsorships.

[00:07:34] Okay, so we’re

[00:07:34] Nathan: making money-

[00:07:35] Chenell: Right … with

[00:07:35] Nathan: Justin.

[00:07:36] Chenell: Correct. So every week in his newsletter, he’s giving you opportunities to reach out to these brands that are looking- Mm … to partner with creators. So he’s helping you make money. He’s saving you time by you don’t have to go search for these things, and he’s time- it’s timely because these are happening right now.

[00:07:51] Nathan: Oh,

[00:07:51] Chenell: okay. Like, these are open opportunities.

[00:07:54] Nathan: So that’s the… Yeah, I was just trying to find two, but you’re- Yeah … you’re saying two or more. Yeah. So make money, save time, and it’s very timely. And so I was like, “Okay, great.”

[00:08:03] Chenell: Yeah.

[00:08:03] Nathan: He also does entertain me in the process.

[00:08:04] Chenell: Totally.

[00:08:05] Nathan: But, but he’s not, like, going all

[00:08:07] Like, being funny isn’t his, his key thing. Right. Right? Whereas there might be other creators who are saying like, “Okay, I’m going to help you save money, and I’m gonna entertain you in the process.”

[00:08:18] Chenell: Right.

[00:08:18] Nathan: And you’re like, great. Let’s … You know, whether I learn something or not, I’m gonna laugh or I’m gonna feel good at the end of-

[00:08:24] Chenell: Correct

[00:08:24] Nathan: what you’ve put together.

[00:08:25] Chenell: Yeah. So that’s a good example of a not deep dive version.

[00:08:29] Nathan: Okay.

[00:08:30] Chenell: Yeah.

[00:08:30] Nathan: Who else has, like, a, a unique combination of these?

[00:08:34] Chenell: Yeah, so if we go back to Mario Gavrili. Mm-hmm. I love this example. Um- He writes for VCs and that kind of thing. And what, before a company goes public, they have to write an S1 report.

[00:08:44] Mm. And so those things are, like, 300 pages long. Oh,

[00:08:46] Nathan: yeah. And even if, like, I read them, I think of myself as, like, generally a smart person, and I understand, like, a quarter of what’s said in that.

[00:08:54] Chenell: Right.

[00:08:54] Nathan: And so someone who reads a lot of S1 reports can say, “Hey, here are the 10 things that are actually interesting or insightful.”

[00:09:00] Chenell: Right.

[00:09:01] Nathan: And so I can, I can teach you about what actually matters and save you a bunch of time in the process. And

[00:09:06] Chenell: potentially make you money or save you money- Right … from investing in something you don’t- Yeah … need to be investing in. So he would put out these, like, 27-page reports that would- Mm … distill those things, work with friends who are in the space, and actually have different insights into that specific S1.

[00:09:19] So…

[00:09:20] Nathan: As we think about maybe people in your community or others that you’ve helped along the way, any examples, anonymized or not, of someone where they, like, didn’t quite nail this, they didn’t have insanely valuable content, and you were like, “Okay, let’s make these tweaks, and we’re gonna dial up one of these six components to make it more valuable”?

[00:09:37] Chenell: Well, somebody in the community, uh, his name is Tom Orbach. He writes a newsletter called Marketing Ideas. And his, um, framework is actually just, like, here’s a quick thing. Here’s exactly how it worked. Here’s how you can do it. And then sometimes he’ll showcase other examples of it out in the pu- uh, out in public and that kind of thing.

[00:09:53] So immediately, like, he’s helping you potentially… He’s definitely teaching you something. Um, he’s saving you time, and he’s probably making you money or saving you money. Mm-hmm. Uh, you can go to your boss and be like, “Hey, we should try this, this new AB test. Like- Right … that would actually be really interesting.”

[00:10:06] And you already know it works, but your boss is like, “Oh, that’s actually a good idea.”

[00:10:11] Nathan: Yeah, that is an interesting thing of, like, often, you know, you and I run in circles of we’re, we’re making content for other creators or entrepreneurs or founders. But, like, making it so that someone who does that job inside of a company is the smartest person in the room- Mm

[00:10:27] always has fresh ideas to bring to the table. You know, you’re the little shoulder angel for them who’s like, “Hey, suggest this this week.” And it’s like, you’re gonna get a lot of subscribers who are gonna be like, “Great, thank you for making me feel smart and make valuable contributions.” Yeah. You know, ’cause ultimately, like, thank you for helping me get that promotion.

[00:10:43] Chenell: Yeah.

[00:10:44] Nathan: The other thing that I love about that angle is you’re gonna end up targeting such a narrow group of people, where if you were like, “Look, my newsletter is for media buyers at e-commerce brands spending at least a million dollars a month on, uh, meta ads.”

[00:10:59] Chenell: Mm-hmm.

[00:10:59] Nathan: Right? Like, you could probably Through direct outreach, reach every single one of those people.

[00:11:05] Chenell: Totally.

[00:11:05] Nathan: Right? And you have such a, a narrow market, and then they’re g- they all know each other. And so if you get really clear on the promise, you know, and who exactly it’s for, it’ll ultimately help in growth, too.

[00:11:15] Chenell: Yeah. There’s a guy named Akash Gupta who writes a product newsletter. Yeah. And his whole thing is optimizing for the internal share.

[00:11:21] Mm-hmm. Which is like, I want this product manager to share this in their Slack with their entire team.

[00:11:26] Nathan: Right.

[00:11:27] Chenell: And then if they all sign up to his paid newsletter, then he gets all those customers.

[00:11:30] Nathan: Yeah. I, the, I love optimizing for the internal share.

[00:11:33] Chenell: Yeah.

[00:11:33] Nathan: That’s great.

[00:11:34] Chenell: Yeah.

[00:11:34] Nathan: And you think about some of these newsletters, you know, like Lenny Rachitsky.

[00:11:37] Chenell: Mm-hmm.

[00:11:38] Nathan: His n- no one would have thought that you could You know, if you said, like, “Okay, if we’re trying to build a million-subscriber newsletter,” they would’ve said, “You would be great at product management.” Right. That’s the one. You would have assumed that then you needed to be in food or finance or some of these, like, very massive TAM-

[00:11:54] Chenell: Yeah

[00:11:55] Nathan: uh, topics. You know, but he’s like, “No, actually, there’s, turns out there’s a lot of people who have this job,” and then you can go one, you know, the, the founders care, the marketers care. You know, like adjacent people, it’s not just PMs. Uh, and then if you optimize for the internal share, like, it’s gonna get spread.

[00:12:09] Chenell: Yeah. I know this seems formulaic, but this is the most important thing. Mm-hmm. Like, every, all of these other things don’t matter as much if you don’t get this first one right.

[00:12:17] Nathan: Yeah. So within this, obviously, we want to choose two of those, but what else goes into leveling up content? ‘Cause I think we, we all come across these newsletters and is like, “Cool.

[00:12:26] Yeah, no, you’re, uh, you’re consistent with your newsletter” Right? Yeah. And it’s like, but is it great? Yeah. Are you super proud of this? Uh, how do you coach people through or, you know, tell them, like, “Okay, you know, if we want any of this to work, we have to level up the content”?

[00:12:40] Chenell: Yeah. I would say if you already have an email list, go get on calls with- Mm-hmm

[00:12:44] 20 or 30 of your readers.

[00:12:46] Nathan: Okay.

[00:12:47] Chenell: Um, I’ve heard over and over again, like Sam Vander Wielen does- Mm-hmm … she did 1,200 free calls with her customers. Recently, there’s a, been an example, uh, these guys who run a newsletter called ADHD Weasel, they got on calls with 300 of their customers, and they’ve just completely nailed the content thing at this point because of that.

[00:13:03] Like, if you’re struggling with this, get on calls with people. That is the fastest way to get the answer. ‘Cause then you’ll know what they need help with, what- Mm-hmm … you’re not providing at this point, and how you can change your content to do that.

[00:13:13] Nathan: I like that. Hey, just a quick note before we keep going.

[00:13:16] If you usually just catch episodes whenever they pop up in your feed, take a second to hit subscribe or follow. We’ve got some great conversations coming up, and that’s the easiest way to make sure you don’t miss them. Thanks so much for your support.

[00:13:28] Chenell: Number two is positioning.

[00:13:30] Nathan: Okay.

[00:13:31] Chenell: So this is essentially, once you have this nailed down, positioning is figuring out how to convey what’s inside of your newsletter.

[00:13:37] So like, your content might be great, but the way you’re talking about it is not helping you. Like, you might just say, like, “Join my free newsletter.”

[00:13:44] Nathan: Right. ”

[00:13:45] Chenell: Subscribe to get the weekly Tuesday edition.” And it’s like, we need a little bit more here.

[00:13:49] Nathan: Okay. Yeah. What are some examples of positioning going, you know, from, from mediocre to great?

[00:13:55] Chenell: From mediocre to great. Well, I was kinda just talking about, uh, the guys with ADHD Weasel. Mm-hmm. They, they actually didn’t start as a newsletter. They started as a, an app. Um, so they were creating an app to reduce food waste. So you could scan a receipt of h- what you bought at the grocery store, and you would know what was in your fridge and when it was gonna expire.

[00:14:12] Mm-hmm. So you do that. They figured out that that app only really catered to people with ADHD.

[00:14:18] Nathan: Yeah.

[00:14:18] Chenell: And they didn’t know that going into it.

[00:14:19] Nathan: Okay.

[00:14:19] Chenell: But by talking to all of their readers, they figured that out. Mm-hmm. And so they started changing the app, and they made it into, like, a meal planning app that was helpful.

[00:14:27] And on the side to grow this app, they were putting out content about ADHD and that kind of thing. And their readers are like, “The app’s cool, but we kind of just want the content.” And so they started the newsletter- Right … ADHD Reads Full, and now it has, like, 36,000 subscribers from 30-

[00:14:43] Nathan: How do they… Do they monetize beyond the app?

[00:14:46] Chenell: Uh, yeah, they closed the app down at this point. Okay,

[00:14:47] Nathan: so yeah, the app is no

[00:14:48] Chenell: more. Just the newsletter.

[00:14:49] Nathan: Okay.

[00:14:50] Chenell: So they have a paid newsletter.

[00:14:51] Nathan: Mm-hmm.

[00:14:52] Chenell: Uh, which I know is not your favorite, but it’s work.

[00:14:55] Nathan: We, we, we’ll see if we get any newsletter hot takes. Okay. I just think, uh, there are better ways to monetize- Yes

[00:15:01] in some cases. Obviously, there’s lots of people, you know, who make a lot of money off of paid newsletters.

[00:15:05] Chenell: Yes.

[00:15:06] Nathan: You just need to be a prolific writer- Yeah … already. Like, I think someone who’s like, “Oh, I, I can put out three or four pieces of content a week, that’s no problem,” all of that, like, great, do a paid newsletter.

[00:15:15] Chenell: Yeah.

[00:15:16] Nathan: But the person who’s like, “I can… I just really struggle to hit the bar for insanely valuable content once a week”- That person should not run a paid newsletter because it, it hits your, your growth of the free content- Mm-hmm … against your monetization. Like, they’re directly at odds because you’re thinking what should be paid, what should, uh, be free.

[00:15:34] Chenell: Yeah. Totally.

[00:15:36] Nathan: That’s undecided.

[00:15:36] Chenell: It’s working.

[00:15:37] Nathan: We… I, I’ve dread that it’s working, but-

[00:15:40] Chenell: Uh, so that’s a good example of just- Mm-hmm … like figuring out how to talk about your newsletter. Tactically, that just looks like maybe a headline on a landing page- Mm-hmm … or what your LinkedIn bio says. Um- Yeah … a lot… I think a lot of people, they just don’t like talking about themselves, so they kind of just like hide it inside of that.

[00:15:55] So with positioning, if you can… If your landing page isn’t converting as well, where people aren’t, uh, as excited about your newsletter as you- Right … hoped they would be, this might be something to play around with.

[00:16:05] Nathan: Okay. So one thing that I’ve been thinking about is even how you iterate on positioning over time.

[00:16:10] Chenell: Yeah.

[00:16:11] Nathan: Like, we’ve been doing this show for 150 or so episodes and still struggle to talk about it, like, exactly the right way. And now with the book, Letters of Wealth, coming out, I’m like, “Okay, how do we incorporate more wealth, money ideas into it?” And so, like, a positioning thing that we’re trying on is saying, like, The Nathan Barry Show is where professional creators go to learn to build wealth or go to learn to build wealth or ha- Like, still playing with how to phrase it exactly.

[00:16:37] Chenell: Yeah.

[00:16:37] Nathan: But even trying to distill it down to something of like, okay, this is who it’s for, and this is what you would hope to get out of it.

[00:16:43] Chenell: Totally.

[00:16:44] Nathan: Now, my worry in that is we might be too in the weeds. You know, we’re talking like growth tactics or that sort of thing, which obviously, you know, we’re growing an audience in a newsletter so that we can make money, so that we can invest that money, so that we can build them off.

[00:16:58] Chenell: Right.

[00:16:58] Nathan: Um, so we gotta figure out the altitude. But it’s something where even doing a show for three years or more, you’re still like, “Okay, is this the right positioning? Are there any tweaks that I should make to it?”

[00:17:07] Chenell: Totally. And that’s another thing with these five is you have to come back to them over time- Mm-hmm

[00:17:11] because they don’t just stay the same over time. Yeah. So your content might change, your positioning will probably change, and that’s okay. It’s like this is why it’s beautiful- Mm … to have, like, an online business, is you can go tweak your headline tomorrow, and it’s not a big deal. Right.

[00:17:25] Nathan: Oh, there’s so many times where I’m Like, as hard as business is, and as hard as online business is ’cause we’re competing all, you know, globally and all of this, I’m like, “So glad I’m not in retail,” or what- whatever else.

[00:17:37] Yeah. You know? Like, “Oh, you wanna change your positioning? Great. You know, two minutes later- … it’s done.” Instead of, like, “Well, let’s see. If we contact our design agency, then they’ll get it to the factory in China, and then…” Yeah. You know? And in nine months, we can have new product on the shelves with new positioning.

[00:17:53] Chenell: Correct.

[00:17:54] Nathan: And even then, you won’t know how someone interacts with it, right?

[00:17:57] Chenell: Yeah.

[00:17:57] Nathan: Like, we actually get to AB test. We get to do everything.

[00:17:59] Chenell: Exactly.

[00:18:00] Nathan: I think about, there’s the line of the man who doesn’t read has no advantage over the man who can’t read. And I think of this in terms of positioning as well.

[00:18:10] Of like, we have the… In online business, we have this insane advantage of being able to get on calls with our customers, split test, you know, all of these things, look at analytics and all of that. And I would say 90% of creators and entrepreneurs don’t Take advantage of that Correct And it’s basically like being the person who, like, doesn’t read.

[00:18:32] Chenell: Yeah.

[00:18:33] Nathan: And it’s like you, you have all of this at your fingertips, and you’re insane if you don’t use it.

[00:18:38] Chenell: Yeah. And I think as newsletters grow, like once you hit 50,000, you’re like, “I got this nailed.”

[00:18:43] Nathan: Right.

[00:18:43] Chenell: Like, forget it. I don’t need to do this anymore. But it’s actually more important at that point because I think you’re getting more of a vast variety of people in your audience.

[00:18:52] And so it might change a little bit. Yeah. And that’s okay.

[00:18:54] Nathan: How would you… So b- in both of these-

[00:18:57] Chenell: Mm-hmm …

[00:18:57] Nathan: um, getting on calls with readers really matters.

[00:19:00] Chenell: Yeah.

[00:19:00] Nathan: What would you use as a carrot? How would you solicit for those calls? And are you trying to look for a particular type of reader, or is it just whoever fills out the Calendly?

[00:19:09] Chenell: Yeah.

[00:19:10] Nathan: Yeah. What do you use?

[00:19:10] Chenell: Yeah. I used to… I try and look for people who are most engaged. Okay. So if they’re opening your emails, clicking, replying- Mm-hmm … is probably the best metric.

[00:19:17] Nathan: Yeah.

[00:19:17] Chenell: Open rates aren’t super, like, like, valuable at this point. But if they’re replying to your content, that’s helpful. Um, if they’ve been on your list for a long time, you can ask them, um-

[00:19:28] Nathan: So you might filter down and say like, “Okay, I have 50,000 people on my list.

[00:19:32] Let me tag everyone who’s been engaged, who, who is, who is engaged now and has been on the list for at least three years.”

[00:19:39] Chenell: Yeah.

[00:19:39] Nathan: And then you might add a PS message to a newsletter or something like that, and say, “Hey, I’d love to meet more of my readers and learn from what’s valuable. Like, hit reply-

[00:19:47] Chenell: Yeah

[00:19:47] Nathan: if you’d be up for getting on a call.”

[00:19:49] Chenell: I actually did this last week. Um, I just sent a straight email to that segment. Uh-huh. I think it was, like, 1,300 people, and I opened up 30 slots, and within, like, seven minutes they were all gone. So I was like, “Oh, I think I picked the right- Okay. … slice of my audience.”

[00:20:00] It was great.

[00:20:01] Nathan: Turns out people wanna talk. Have you had any of those calls yet?

[00:20:03] Chenell: No, they’re next week.

[00:20:04] Nathan: They’re-

[00:20:05] Chenell: Yeah.

[00:20:05] Nathan: They’re all coming up. Yeah. Actually,

[00:20:06] Chenell: it’s Monday. Yeah. So, no, I’m excited about that. But I’ve done it before. Hm. And it’s just always so helpful to see who these people are, what actually is their pain point.

[00:20:14] Like, email’s fun, but that’s not everyone’s life. Yeah. Like, what is actually happening in their life? What’s the actual transition point they’re in right now, and how can I help get them to the next

[00:20:23] Nathan: one? Are there any shifts that either you’ve made or you’ve seen students of yours make after doing these calls?

[00:20:28] Chenell: Yeah. Um, well, uh, we were talking about Sam Vander Wielen. Yeah. Uh, she was selling these templates one-off, and she started actually bundling them together ’cause people were like, “Well, I need, like, multiples of these.” Mm-hmm. And she said that she could have actually written a full course on how to do this stuff, and she’s like, “Maybe I should just do that and make that my product.”

[00:20:46] Nathan: Mm-hmm.

[00:20:47] Chenell: And so over the time with talking to people, she actually did that, and now she’s made, like, $10 million or something crazy with that one product.

[00:20:53] Nathan: Yeah, it’s insane. The ultimate bundle continues- Oh my gosh … to sell really well. She did an episode, uh, I don’t know, it’s like 10 episodes ago on this show breaking down her launch where she did over half a million dollars in the launch.

[00:21:03] At a time when everyone’s like, “Oh, courses are dead”- Correct … she’s like, “If you say so.”

[00:21:07] Chenell: Yeah, webinars are dead, courses are dead, and she’s like, “Not really, but all right.”

[00:21:11] Nathan: Yeah. Anything else on positioning?

[00:21:13] Chenell: No, I don’t think so. I think it just ties into number three really well.

[00:21:16] Nathan: Okay.

[00:21:16] Chenell: So.

[00:21:17] Nathan: What a good segue.

[00:21:17] What’s number three?

[00:21:19] Chenell: Number three is building momentum or distribution.

[00:21:22] Nathan: Okay.

[00:21:22] Chenell: But essentially, this is where people focus. This is the one that everyone pays attention to, and when their newsletter’s not growing or it’s stalled or plateaued, they’re like- Mm … “I just need to go back to

[00:21:31] Nathan: the-” What’s the growth hack-

[00:21:32] Chenell: Correct

[00:21:33] Nathan: that’s gonna get me to the next stage?

[00:21:33] Chenell: What’s the new ManyChat strategy? Mm-hmm. What’s the new social platform I should be on? Should I start yapping?

[00:21:38] Nathan: Okay.

[00:21:38] Chenell: Yeah. Um, so everybody goes to this one. And it’s important. Like, you need that distribution, but, um, I think people spend way too much time here and not focusing enough on the other four.

[00:21:49] Nathan: Okay, so l- but let’s say we have insanely valuable content-

[00:21:52] Chenell: Yes …

[00:21:52] Nathan: and it’s really well-positioned. Yes. Like, what actually makes a big difference in building momentum?

[00:21:56] Chenell: Focus. So pick one thing. Yeah. Try it out for six months. If it’s not working, move on. Mm-hmm. But I think most people try and do two platforms, three platforms, and they never get good at any of them, and then that’s where you kinda struggle.

[00:22:10] Nathan: What are the things for distribution that are working really well right now that you’re seeing across the board?

[00:22:15] Chenell: There’s a couple things. My favorite is probably quizzes.

[00:22:18] Nathan: Okay.

[00:22:19] Chenell: Uh, quizzes are working super well.

[00:22:21] Nathan: Mm-hmm.

[00:22:21] Chenell: I can give you an example from, uh, my friend Charlie Dice. So Charlie had been writing a newsletter for two years about farming and, like, growing your own food and why that matters and all that stuff.

[00:22:31] And we jumped on a call in August of last year, and I was like, “You have these cute little pigs running around. You’re doing awesome stuff on the farm. You should really be on Instagram.” She was like, “I hate social media, I’m never doing video,” and I said, “Okay.” Uh, fast-forward to November, uh, mid-November, it was November 18th.

[00:22:49] We jumped on another call, and she was like, “Well, I work for the government, and October of this year- Mm-hmm … the government shut down, so I had nothing to do ’cause I was furloughed.” I said, “Okay,” and she’s like, “I started a TikTok account,” and I was like, “All right, keep going.” And, um, she actually started with a completely different topic about how she hit a million dollars in net worth by the time she was 35.

[00:23:13] Mm-hmm. And she was wr- like, creating these three-minute long TikToks, which I didn’t even know worked-

[00:23:17] Nathan: Yeah …

[00:23:17] Chenell: on that platform, and was like, “So I hit 58,000 followers in 30 days,” and I was like, “What?” And then I was like, “Hold on, you have to get subscribers from this. Like, let’s not just grow a following.”

[00:23:29] Nathan: Right.

[00:23:29] Chenell: And she was like, “Great.” And it, so I told her about Tori Dunlap- Mm-hmm … and Millie Tamati, who’s another great example of this, who are using quizzes partner or paired with TikTok and Instagram to be able to grow their subscriber list really fast. I think Tori’s quiz has now been taken, like, over a million times, which is just-

[00:23:45] Nathan: That’s wild

[00:23:45] Chenell: insane.

[00:23:46] Nathan: What is Tori’s quiz? Like, dive into-

[00:23:48] Chenell: Yeah. So her quiz, I’m not gonna remember the exact thing, but it’s about, like, how to be a better… like, how to build wealth essentially for women.

[00:23:55] Nathan: Yeah. Mm-hmm.

[00:23:55] Chenell: Um, and so she gives you, like, four different archetypes that you end up being, and beyond that, each of those has its own different- Mm-hmm

[00:24:02] like, plan, if you will. Like, your better, best next step. And so I told her, I was like, “Do you know about Tori Dunlap?” And she was like, “I don’t.” And I said, “Great. Go read this deep dive.” Uh- Right. This girl Millie came into our, uh, community, and she was also doing a quiz on TikTok. Mm-hmm. Charli’s like, “Okay, cool.”

[00:24:19] And so she did that. She ended up with 1,500 subscribers in nine months, so she doubled what she had gotten from her first newsletter after- Okay … she was writing that one for two years. This was 90 days. Uh, now she’s at s- uh, 15,000 email subscribers in, what is that? A few months? Yeah. Like, not even 12 months, 10 months.

[00:24:38] So, uh, it’s working really well, and she’s monetizing it as well.

[00:24:42] Nathan: So, uh, what’s her quiz?

[00:24:44] Chenell: Her quiz is, um, her newsletter is called Building Quiet Wealth, so it’s just how to, like, what are the best next steps for you to build towards that $1 million net worth? Mm-hmm. And so there are four different options that you can end up in.

[00:24:57] Okay. Um, and each has a name and a different email sequence on the back end.

[00:25:00] Nathan: And then what’s the mechanism to go from short form video into the quiz? Is it just the link, or are we doing comment to DM?

[00:25:06] Chenell: Yeah. So the best part with the quiz is if you buy the URL. So it’s like Building Quiet Wealth Quiz or whatever it is.

[00:25:13] Yeah. You can show that on the screen in your video and say, like- Mm-hmm … “I put together this quiz. It’s helped 3,500 people. This person’s done a certain thing,” and you just have the URL in the back- Mm-hmm … on screen. So you can do it that way so that you’re not putting a link in the comments- Right … or in the caption.

[00:25:28] So that’s another way to do it.

[00:25:30] Nathan: Do you find that links, depending on the platform, are- Changing how the video performs in the algorithm?

[00:25:36] Chenell: Yes.

[00:25:36] Nathan: Okay.

[00:25:37] Chenell: I know some people are like, “No, no, it doesn’t matter.” I’m like, “Okay.” But I’ve talked to enough people who say- Maybe they say that … yes, it does matter.

[00:25:43] Nathan: Yeah.

[00:25:43] Chenell: But depends on the platform, but yeah, for

[00:25:45] Nathan: the- But you could also do that.

[00:25:46] You could say, you know, comment quiet wealth and- Totally … on Instagram. Does comment automation work on TikTok or

[00:25:52] Chenell: no? I think so. I don’t know if it’s- Okay … as robust as what you can do- Yeah … on Instagram, but you can do a little bit.

[00:25:57] Nathan: Okay. Yeah. So the quizzes have worked really well. And we- we’ve seen this, like, um, Gretchen Rubin with her, uh, Four Tendencies.

[00:26:04] You know, she has a book related to it and all this. I think she’s picked up, like, 500,000 or more subscribers off of a quiz.

[00:26:11] Chenell: Yeah.

[00:26:11] Nathan: Uh- It’s wild … someone really good to follow through all the stuff quiz related is Daniel Priestley.

[00:26:16] Chenell: Mm.

[00:26:16] Nathan: Right? He’s got a company around it. Yes. And, uh, yeah, there’s a ton of great deta- detail there.

[00:26:21] Chenell: Yeah. And it’s still working. Like, I talked about this at a conference in February-

[00:26:25] Nathan: Mm-hmm …

[00:26:25] Chenell: in Austin, and these two guys were in the audience. And I didn’t know who they were, but about a month after the conference I got this email, and they’re like, “Hey, we took your advice.” I’m like, “What?” Which never happens.

[00:26:37] Yeah. Like, I love this. So I open it up. It’s, like, this five-page PDF of, like, “Here’s what we did. Here’s exactly how, uh, we’re growing now.” And the ADHD Weasel guys, they took this, and they turned it into, um, a Weasel quiz. Yep. And essentially, like, what type of ADHD are you, how to do all this. And, um, they went from adding 15 new subscribers to 127 a day.

[00:27:00] Nathan: Oh, wow.

[00:27:01] Chenell: Yeah.

[00:27:02] Nathan: No big deal. Just 9X growth. Yeah. 9X your daily growth rate.

[00:27:05] Chenell: Exactly. Um, and so they are now using that for- Mm … paid ads and everything too, so they’re just, like, growing super fast. And so this is still working. Like, that, that was in April.

[00:27:15] Nathan: So- That’s awesome.

[00:27:15] Chenell: Yeah.

[00:27:16] Nathan: Okay, you said something that makes me wanna have a, you know, a direct-to-camera segue for a second.

[00:27:20] Okay, what Chanelle said is- People took her advice, which they almost never do. This is the case for so many creators, where you put out all this amazing content, you go into detail. Most people say, “Oh, that’s interesting.” You know, and they dive into little bits of it, but they don’t actually do it. If you want to get to know creators personally, dive into their content, take their advice, implement it, and then reach out and say, “You told me to do X.

[00:27:43] I did it, and here are the results.” And you immediately jump from one of 50,000 to, like, one of five people who do it. Yeah. So if you wanna meet, meet more creators, do that.

[00:27:52] Chenell: Yeah. I had him on our podcast and everybody was telling-

[00:27:58] Nathan: And it’s like, huh, the worst-case scenario is you might try something and it didn’t work, and you’re like, “Okay, that’s fine.”

[00:28:03] Chenell: Exactly.

[00:28:03] Nathan: But, like, everybody consumes all this content.

[00:28:06] Chenell: Oh, my gosh.

[00:28:06] Nathan: No one actually puts it to work.

[00:28:07] Chenell: Yep.

[00:28:08] Nathan: And so you immediately- You really stand out … jump to the top. You stand out if you do it.

[00:28:11] Chenell: You definitely stand out. Yeah. And even if it does work and you don’t- you don’t tell them, it’s like, what was… Like, come on.

[00:28:17] Just do that one last-

[00:28:18] Nathan: Right …

[00:28:18] Chenell: send the email.

[00:28:19] Nathan: And it will turn it, like, uh, worst-case scenario in that is you… I guess worst case is you don’t get a reply.

[00:28:25] Chenell: Right.

[00:28:25] Nathan: But, uh, you know, most likely you’ll get a reply back like, “Oh, that’s so awesome. I’d love to hear it.” But it’s pretty likely that someone will say, like, “That’s amazing.

[00:28:32] Can I get on a call with you to learn more about what worked? C- will you come on my podcast? Will you-

[00:28:37] Chenell: Correct …

[00:28:38] Nathan: you know, do all of these things?” Because it’s so much validation.

[00:28:40] Chenell: Yeah, ’cause nobody does it. ‘

[00:28:42] Nathan: Cause nobody does it.

[00:28:43] Chenell: Please. Please.

[00:28:46] Nathan: All right, so quizzes are really valuable. Um, while I’m thinking about it, if you were putting together a quiz, let’s say hypothetically, you had a book called The Ladders of Wealth coming out March 2nd, um, how would you structure or suggest doing a quiz around that?

[00:28:59] Chenell: Yeah. Uh, that’s a good question. I think you need to back into, like, the f- four to six people that- Mm-hmm … this would serve best, and then from there, you can figure out what questions can I ask to, like, filter those people into the buckets.

[00:29:11] Nathan: Yeah.

[00:29:12] Chenell: Um, so-

[00:29:12] Nathan: So in this case, in mine, I have the four ladders.

[00:29:16] Chenell: Right.

[00:29:16] Nathan: And so we can do a quiz to identify which ladder you’re on and, like, what skill you should move ne- uh, learn next to move to the next ladder.

[00:29:23] Chenell: Right. Okay. And so you could ask people, like, “Do you have a day job?”

[00:29:26] Nathan: Mm-hmm. ”

[00:29:27] Chenell: Are you working for yourself?” Like- Yeah … “Do you have employees?” That kind of thing, and then help them get into that-

[00:29:32] Nathan: Yeah

[00:29:32] that plan. And then they’re, like, deeply into my methodology and-

[00:29:35] Chenell: Correct …

[00:29:35] Nathan: all that.

[00:29:36] Chenell: And then they’ll probably buy the book.

[00:29:37] Nathan: Yeah, there you go. That’s

[00:29:39] Chenell: the goal. They’ll at least be on your email list.

[00:29:40] Nathan: Right. Then I have the opportunity to sell them the book.

[00:29:42] Chenell: Yeah.

[00:29:43] Nathan: Okay. So when we’re talking about building momentum, uh, quizzes work well.

[00:29:46] What else?

[00:29:47] Chenell: Lead magnets are awesome. Okay. I’ve been in the online space since 2013, and I’ve seen lead magnets for years, but that they’re making a resurgence, and they’re just- Yeah … changing a little bit. So in the past it used to be, like, a PDF or a checklist or something.

[00:30:00] Nathan: Mm-hmm.

[00:30:01] Chenell: Now you can do… I mean, a quiz is essentially a lead magnet.

[00:30:03] Nathan: Yep.

[00:30:04] Chenell: But you can also do… Not to bring her up again, but Sam, Sam Vander Wielen does lead magnets where it’s just, like, buckets of episodes.

[00:30:10] Nathan: Hmm.

[00:30:10] Chenell: And so- Okay … she’ll have specific episodes around, like, money, right?

[00:30:15] Nathan: Yep.

[00:30:16] Chenell: This is my horrible handwriting.

[00:30:17] Nathan: Oh,

[00:30:17] Chenell: yeah. So she’ll have specific episodes around this, and she’ll post a video and say, like, “Comment the word money-

[00:30:23] Nathan: Mm-hmm

[00:30:24] Chenell: and I’ll send you this

[00:30:26] Nathan: playlist.”

[00:30:26] Chenell: The, the

[00:30:26] Nathan: three episodes that I did on this, or the six episodes. Correct. Yep.

[00:30:29] Chenell: Yeah. And so she said that’s added thousands of subscribers to her email list.

[00:30:33] Nathan: And that’s so easy to do.

[00:30:34] Chenell: So you’re not- … creating anything net new. You’re taking what you already have built and just packaging it differently.

[00:30:39] Nathan: Right. Okay. Well, we’re suggesting lead magnets. Another one that I’ve seen work well is AI skills, right? And you bundle up some AI skills. People want that. Yeah. And you’re just like, “Hey, what, what have you already trained your agents on, or what do you use on a day-to-day basis?”

[00:30:53] Chenell: Right.

[00:30:53] Nathan: Um, and say, “Here you go.”

[00:30:55] Chenell: Yeah. And- And if you can do these well, that’s, that really helps. Mm-hmm. We’re running a challenge right now, and I built one to make… like, for insanely valuable positioning-

[00:31:03] Nathan: Mm-hmm …

[00:31:03] Chenell: um, to figure out, like, okay, you have this content. How do you position it? And people are loving it. So, like, it’s, it’s more work-

[00:31:10] Nathan: Yeah

[00:31:11] Chenell: but you stand out, and you’re helping people cus- Mm-hmm … like, in a custom way without doing one-on-one coaching.

[00:31:16] Nathan: Yep, I like that.

[00:31:17] Chenell: Yeah.

[00:31:18] Nathan: Yeah, ’cause oftentimes people are like, “Okay, I’ll prompt the client to do this thing for me.” Right. And it’s like, ah, but you’re gonna get the worst result back.

[00:31:23] Chenell: Yeah.

[00:31:23] Nathan: But if you just implement this, you know it’ll be way better.

[00:31:26] The other thing that I love about it is you can… We always want to do the, like, cross the, the gap from, “Let me tell you what to do,” to, “Let me do it with you”- Yeah … to, like, done for you. And in that… And lead magnets always live in this- Uh, let me tell you what to do category.

[00:31:41] Chenell: Yes.

[00:31:42] Nathan: And so, you know, in this case, we’re able to jump ahead and be like, “Okay, let me actually do it with you at scale by giving you a, an AI skill for

[00:31:50] Chenell: it.”

[00:31:50] And you can almost combine these and say like, “All right. Let me put the transcripts from these episodes into a skill- Oh, that’s

[00:31:54] Nathan: interesting …

[00:31:55] Chenell: and just have it prompt you however many questions.”

[00:31:57] Nathan: I like that. Okay, what else on building momentum or, or, um, distribution?

[00:32:01] Chenell: People aren’t gonna wanna hear this, but I would say more volume on social.

[00:32:05] Nathan: Okay.

[00:32:06] Chenell: I think a lot of us are playing safe.

[00:32:08] Nathan: Mm.

[00:32:08] Chenell: Just to continue with this story, uh, the ADHD guys, they’re putting out 120 posts on threads every week.

[00:32:17] Nathan: Oh, wow.

[00:32:17] Chenell: Yeah. As two guy- Like, it’s just two guys doing this. This isn’t like Dan Martell situation- Yeah … or Cody Sanchez or anyone. Like, just he … Every Monday, he sits down and he writes out that week’s post, and he schedules them out.

[00:32:28] And throughout the week, he’ll just look for good formats that he’s enjoying, and that kind of thing, that he thinks are gonna work. And so I feel like sometimes we play it too safe with-

[00:32:37] Nathan: So we’re like, “Hey, I did well. I put out, um, I, I posted every day on the three platforms that I care about. Like, good job me.”

[00:32:45] And it’s like, okay. To give you an idea, um, I was texting with Simon Squibb’s team the other day, and they said they’re now up to 18,000 pieces of organic content posted every month. And you’re like, “What in the world is happening?” Um.

[00:33:00] Chenell: Wow. Yeah.

[00:33:00] Nathan: And, you know, they’re cutting things up a whole bunch of different ways.

[00:33:03] They’re repurposing. They’re, they’re doing all of the stuff. But another crazy thing that’s happening on social media right now is there’s not the same benefit to, like, growing a single account as there used to be.

[00:33:12] Chenell: Yeah.

[00:33:13] Nathan: And so a lot of these creators are clipping their… And not just, you know, do I have a couple great clips from an episode, but they’re growing tons and tons of accounts.

[00:33:22] Because- You know, a piece of content is almost as likely to go viral or spread, you know, from a, a brand new, like, 100 follower or 1,000 follower account as from a 10 or 20,000 follower account. And so you’ll see people grow a huge number of accounts as well, which is kinda wild.

[00:33:40] Chenell: Wow. Okay, so they have, like, multiple Instagram accounts or multiple-

[00:33:43] Nathan: Yeah

[00:33:44] YouTube- And they might have done… So if you were to look at a popular show, like let’s take the Kelsey Brothers-

[00:33:48] Chenell: Okay …

[00:33:48] Nathan: right, with their, uh, their podcast. You- if you were to deep dive, there are a ton of Instagram and TikTok accounts posting clips from their show. Many are owned by them. Um, many more are just fan accounts and that sort of thing.

[00:34:03] But, like, it’s the same idea of h- it’s just how do you get your content out there to as many, um, views as possible? Okay. And people care less about owning the relationship with the follower. It’s a wild world. Yeah. But your point is even as a solo creator who’s just like, “Look, I wanna j- um, grow my own accounts,” you can crank up the volume.

[00:34:23] Chenell: Yeah, totally.

[00:34:24] Nathan: There’s a version of this that’s just AI slop, right?

[00:34:26] Chenell: Right.

[00:34:27] Nathan: Where it’s just like give me a whole bunch of hooks. You know, cut this 10 different ways. Uh, how do you do this and maintain the bar for insanely valuable content?

[00:34:34] Chenell: So I think it happens over time, too. Mm-hmm. And, like, as you’re posting more, you’re getting more wins, so to speak.

[00:34:40] And so you have this library of content that works. Mm-hmm. And so you can repurpose that in three months or whatnot. And then over time you just, you’re not creating as much net new content and you’re just… But in the early days, yeah, you have to build out, um, frameworks to figure out like, okay, there’s this format that’s working.

[00:34:54] Right. How do I pull this into my topic, my content? And yeah, it’s just work.

[00:35:01] Nathan: Yeah. And you know, the more you put out, then the more you’re gonna find out what works.

[00:35:05] Chenell: Right.

[00:35:05] Nathan: Laura Roeder would talk about this years ago, um, where she would say, “You should repurpose your content.” And then I feel like Nick Huber is someone who got really good at that, um, more recently, like 2021 onwards.

[00:35:19] But it totally works- Yeah … to have a spreadsheet of your top content. You don’t know what your top content is. The easiest thing is, yeah, like, if you go on X and you just search from colon Nathan Barry.

[00:35:28] Chenell: Yep.

[00:35:28] Nathan: You know, min_faves:500. And it’s like, okay, now it’s only showing my posts that have at least 500 favorites.

[00:35:35] You can scroll through and you’re like, “Oh, okay. Huh, I last posted this a long time ago.” And the other thing is if you’re like, “Okay, I grew well on X. Now I want to grow on Instagram.”

[00:35:45] Chenell: Right.

[00:35:46] Nathan: Well, there’s a… That search is gonna tell you which topics, uh, performed really well.

[00:35:52] Chenell: Totally.

[00:35:53] Nathan: So, like, when I was… I, I was writing a slightly different book before.

[00:35:57] And I sat down with James Clear to talk about, like, the positioning of it, ’cause we have to get this right. And he came back, and he was like, “The previous topic was more about audience growth and creator business and all of that.” And he’s like, “People like to hear about you for, uh, about money.” Um, ’cause he went through and he was like, “Look,” uh, it was like something like 18 of my 20 most popular X posts were about money and wealth.

[00:36:21] And so he, you know- Like- Being able to use that filter of like what does the audience care to hear about you from works really well, and then you can apply that in a bunch of other formats. So I, I still need to do this, of go back through my X posts and make Instagram videos of each one- Yeah … of one of those.

[00:36:39] Chenell: Another thing that people miss is like you comment on other people’s posts. Mm-hmm. And sometimes those comments get really good engagement, so it’s like can I take that piece of content and turn it into my own? Right. And so I think that’s where you get… you miss a lot of opportunity, too. Mm-hmm. And you kind of forget that comments count as content.

[00:36:53] And so you can take that and add that into your volume play.

[00:36:56] Nathan: Yep.

[00:36:56] Chenell: Yeah.

[00:36:57] Nathan: That makes sense. What are you doing around volume, and how do you think about that?

[00:37:02] Chenell: Great question. Yeah. This is one of those like cobbler’s kids have no shoes- Yeah … kind of thing. Uh, I’m going to start doing this more because after hearing how they were putting out- Mm-hmm

[00:37:10] 120, I was like, “This is silly.” Like, I need to be doing more. I have so many growth levers and people that I’ve researched. And even just like- Mm-hmm … saw dust from this stuff, right? Right. Of like, oh, I found this really interesting quote that they posted, or like the Jack Butcher like this is pointless meme.

[00:37:25] Uh-huh. Like all of that stuff, like I can just repurpose that and talk through those things. So, I’m gonna start building this out with Claude and be able to like pull out those levers and just build- Yeah … a spreadsheet and go

[00:37:34] Nathan: to town. Well, and it’s kind of like if you… say you do these deep dives, right?

[00:37:38] Yeah. And you have deep dives of, of, you know, thousands of words and hours of research on every creator all the way across. Well, if you do what Sam did with the money idea- Yeah … and you say like let me draw a line around, you know, like what do these five creators have in common?

[00:37:51] Chenell: Yeah.

[00:37:51] Nathan: You know, they all use this tactic or technique.

[00:37:54] And it’s not brand-new content you have to make.

[00:37:57] Chenell: Right.

[00:37:57] Nathan: You can mine it. And that’s the other thing that AI is really good for.

[00:38:00] Chenell: It

[00:38:00] Nathan: is. Is saying, “Okay, here’s the type of thing that I wanna put out. You know, help me-” Repackage still an original work

[00:38:08] Chenell: Yeah. Or even just, like, listening back to my own podcast episodes.

[00:38:11] I’m like- Mm … oh, yeah, I totally forgot they said that.

[00:38:13] Nathan: Like Yep. Something that Kara on my team has been working on a lot is a library in Notion of everything that I’ve ever put out on the internet, and then all of my flagship ideas. And we’re, we’re pulling all that together. Which ones have illustrations?

[00:38:26] Which ones should have illustrations? And then mining every time I, I go as a guest on another podcast. What are the best ideas and stories? Have we told those stories before?

[00:38:34] Chenell: Mm-hmm.

[00:38:34] Nathan: And, uh, it’s very, very powerful. ‘Cause another thing that I realized, I was always trying to come up with original content-

[00:38:42] Chenell: Mm-hmm

[00:38:42] Nathan: over and over again. What is something that I could say that I have not said before? And that’s entirely the wrong lens.

[00:38:47] Chenell: Yes.

[00:38:48] Nathan: Y- like, I remember listening to Jason Fried from Basecamp, you know, someone that I’ve really, really admired and learned a ton from. And if you listen to him on 10 podcasts, you’re probably gonna hear 80% the same content.

[00:39:02] Chenell: Yeah.

[00:39:02] Nathan: Right? Or Will Guidara from Unreasonable Hospitality, right? He’s gonna tell his greatest hits, his stories, and those are gonna keep coming up. And it’s like, yeah, that’s what… People wanna hear him share the hotdog story, you know? And- Right.

[00:39:13] Chenell: And you forget about them, and so the next time you hear that thing, you’re like, “Oh, yeah.”

[00:39:16] Nathan: Oh, that was such a good one. Yeah. You know?

[00:39:18] Chenell: Yeah.

[00:39:19] Nathan: Uh, and so it’s okay to tell those same stories over and over again in slightly different ways.

[00:39:23] Chenell: Yeah. I’m getting better at this. When I go to speak, I always create a new presentation, which is, like, the worst thing you can possibly do.

[00:39:29] Nathan: That’s playing into our mugs.

[00:39:30] But, you know.

[00:39:31] Chenell: But it’s helped me come up with so much more content now- Right … because I have these different frameworks and these different examples to share. Mm-hmm. So it’s helpful, but I need to stop doing that.

[00:39:41] Nathan: That’s right. Um, what is number four?

[00:39:43] Chenell: Number four ties directly to this one, but it’s conversion.

[00:39:46] Okay. So how do we take this momentum that we’re building and turn it into subscribers? Because we’ve all seen the people who have hundreds of thousands of followers, and they’re like, “Yeah, I have 5,000 email subscribers.” And I’m like…

[00:39:58] Nathan: Kills me.

[00:40:01] Chenell: Or I don’t have an email list, which is even worse.

[00:40:03] Nathan: Okay, that one actually kills me.

[00:40:04] Chenell: Yeah. Same. Um, so this is essentially, it’s a little bit more tactical, but it’s, you know, landing page conversion rate. Mm-hmm. How many people are seeing your LinkedIn profile and subscribing to your email list? Mm-hmm. How many people are… Like, so looking at the numbers and being able to tie back like, okay, is the momentum stuff work- working?

[00:40:23] And if not, maybe it’s positioning. Right. Do we need to do more volume with the momentum?

[00:40:26] Nathan: So- So then, you know, if you’re going, I don’t know, impressions to, uh, I guess-

[00:40:32] Chenell: Yeah, like landing

[00:40:33] Nathan: page … clicks onto a landing page, and then subscribers.

[00:40:37] Chenell: Yep.

[00:40:37] Nathan: I guess engagement is probably next, and then ultimately sales.

[00:40:40] But yeah, each one of these is a leverage point. People don’t focus on that nearly enough.

[00:40:44] Chenell: No. And so I’ll have people come to me and be like, “All right, I wanna hit 50,000 subscribers in the next two years.” Mm-hmm. “How do I do that?” And I’m like, “All right. Is this really important?” And they’re like, “Yeah, it’s the most important thing.”

[00:40:54] And then I go to their website, and the signup form is all the way in the footer. And it’s like, “Join the weekly newsletter.” Mm-hmm. And I’m like, “Is this really that important? ‘Cause if it is, it needs to go in the header, and it needs to be first.”

[00:41:05] Nathan: Right.

[00:41:05] Chenell: It absolutely needs to be the first thing.

[00:41:08] Nathan: So when I…

[00:41:08] Whenever I’m working on a talk, which similar to you, I write lots and lots of new talks, and I should not do that. But the question that like Mike Pacchione or Barrett Brooks or other people that I go to for advice on this, they always ask is, ’cause I’m like, “Okay, I’m trying to cover all of this. It’s gonna be great.”

[00:41:22] And they’re like, “What is the one thing you want people to take away from this talk?” I’m like Oh, it’s this. And they’re like, “Cool. So maybe let’s re-anchor the talk around that one thing.” And you’re building up to it and reinforcing it and all that. And I think conversions are the same thing- Yeah … where someone comes to the page and z- you’re like, “Yeah, it does all these things.”

[00:41:39] Like, and you’re like, “What is the one thing you want people to do?” “Well, subscribe obviously.” And you’re like, “Okay. So now, now that we’re clear on what the goal is, uh, look through that landing page and tell me is it clear to the reader- Right … what the one thing is?” And nine times out of 10 they’re like, “Oh.”

[00:41:54] Chenell: Right.

[00:41:55] Nathan: Right.

[00:41:55] Chenell: Exactly. Uh, so this is another thing. Like, my spicy take is, like, I hate Linktree. Sorry to the company. Yeah. But, like, those types of, of platforms, they really muddy the waters. Mm. And so if you have a Linktree account in your, in your-

[00:42:09] Nathan: Link in bio.

[00:42:09] Chenell: Yeah. Yeah In your link in bio, it’s like, “Go sign up for this product.

[00:42:13] Here’s my affiliate code for this.” Mm-hmm. And then at the bottom it’s like, “Join the email list.” And I’m like, “All right. But maybe that should be first,” and then you can sell them all that stuff from the emails.

[00:42:21] Nathan: Right.

[00:42:22] Chenell: And so I think we need to change our focus here.

[00:42:25] Nathan: Okay. So if we think about a good link in bio.

[00:42:27] Chenell: Mm-hmm.

[00:42:27] Nathan: Right? ‘Cause that’s a lot of people are going to see, oh, this is an interesting account.

[00:42:31] Chenell: Yeah.

[00:42:31] Nathan: I wanna learn more. I click in. I always click in ’cause I’m like, do they have a newsletter? Yeah. Do they have a newsletter on Kit? Should I DM them and see and get them there? Uh, the things that I want in the link in bio, I wanna know a little bit more detail about who they are.

[00:42:45] Chenell: Mm-hmm.

[00:42:46] Nathan: And then I really wanna know what do they have to offer generally for free and, like, that, you know, that email sign-up. And that’s kinda it.

[00:42:53] Chenell: Yep.

[00:42:54] Nathan: What, what would you say? Like, what’s most important?

[00:42:56] Chenell: Same thing.

[00:42:57] Nathan: Okay.

[00:42:57] Chenell: It goes right to either the newsletter landing page or your homepage- Mm-hmm … which is mostly about your newsletter.

[00:43:02] Nathan: Right.

[00:43:03] Chenell: Yeah. ‘Cause I, I know a lot of people, they might be copywriters, and they serve clients, and so they’re like- Mm … “But I want them to book a call.” And I’m like, “What do you think the chances are of them clicking the link in your bio and booking a call from there? Probably pretty low, but if you can get them on your email list and talk to them and build trust- And then you

[00:43:18] Nathan: have the whole email sequence- Correct

[00:43:19] that’ll get them to book a call.

[00:43:20] Chenell: Right. And so it might be okay to have that- Mm … as one of your call to actions, but if growing your email list is important, then- Yeah … showcase that.

[00:43:28] Nathan: What are some examples of people really taking one of these conversion levers in here and, uh, increasing them quite a bit?

[00:43:35] Chenell: Yeah. So one of my favorites is Drew Riley from Trends.vc. Yeah. Um, so he had a newsletter, and he was trying to figure out how to grow it. And I was … I wrote a deep dive on him. This is how I found it. And he had been posting the product, um … Was it Product Hunt? I don’t know. Indie Hackers.

[00:43:51] Nathan: Indie Hackers, yes.

[00:43:51] Chenell: Indie Hackers. And he saw this other guy named Dan, who actually runs TLDR- a huge newsletter. And Dan was like, “Hey, my sign-up page converts at 40%.” And Dan, or Drew was like, “How did you do that?” Like, and you could see him just being, like, really excited about this. And then he spent the next year figuring this out, and I found 17 iterations of his landing page.

[00:44:14] Mm. And so it went from, like, really confusing headline. Yep. He changed the headline. He dropped one of the form fields ’cause he was asking, like, name and email, so he dropped the name. He added, like, social proof on it. Mm-hmm. And there were just different iterations, and now h- it’s converting at over 40%.

[00:44:28] Nathan: That’s awesome.

[00:44:29] Chenell: Yeah. And so just the consistency and, like, actually focusing on this thing- Mm-hmm … actually helped that, so.

[00:44:34] Nathan: You know, if we think about the conversion points that matter most, like the on page conversion is one of those. Yeah Like, of visitors coming through the page to subscribers. That matters really a lot.

[00:44:48] One of my pet peeves though is when people say, like, “Oh, your landing page converts at 40%, so let me copy paste that- Yeah … and tweak a few details, and that design will convert at the same rate for me.” ‘Cause they totally miss the fact that the, like, the impressions and the intent coming through the funnel matters.

[00:45:04] That’s at least half of the-

[00:45:05] Chenell: Yeah …

[00:45:06] Nathan: of the conversion. And so the two points that I would focus on- Is like the quality of the impressions that you’re getting-

[00:45:11] Chenell: Mm-hmm …

[00:45:11] Nathan: and then how you’re converting them to subscribers.

[00:45:13] Chenell: Yeah.

[00:45:14] Nathan: I think that matters most.

[00:45:15] Chenell: Well, funny enough, I stole Drew Riley’s landing page.

[00:45:18] Uh-huh. And it did convert at 40%.

[00:45:19] Nathan: Did it really?

[00:45:20] Chenell: But it did change up like the headline- Yeah … and everything. But yeah, it was the same layout. Like, it looked pretty close. There was no extra links on it. Yeah. You couldn’t do anything but sign up. And so I think people just muddy the waters, and they wanna add- Mm-hmm

[00:45:30] recent posts and all this other stuff to that page, and it’s like, “Get the email. Thank you.”

[00:45:35] Nathan: Yeah. You can do all, everything else later- Yeah … once you have the email address.

[00:45:38] Chenell: Exactly.

[00:45:39] Nathan: Yep. I like it. Um, what else on conversion?

[00:45:41] Chenell: I mean, if we’re talking about conversion, we wanna talk about free to paid newsletters or- Yeah

[00:45:45] selling products and that kind of thing. Yep,

[00:45:47] Nathan: the money side of it- Yeah. … ’cause you’re right. We’re underlining things.

[00:45:51] Chenell: Go back to this money thing over here.

[00:45:52] Nathan: Profit lets you do it again tomorrow, so.

[00:45:55] Chenell: Again, you actually talked about this, and I was gonna bring it up, but the quality of the impressions is so- Mm-hmm

[00:45:59] key with this. You can build so much momentum, but if you’re bringing the wrong person, and you’re just- Mm … trying to get views for the sake of having views- Right … it’s not really gonna be helpful. And so you can do all these new formats and, like, get not great people to- Mm-hmm … watch your stuff, and then you get to this point, and you’re like, “Why is nobody signing up?”

[00:46:16] Mm. And it’s like, so you really wanna be intentional about who you’re creating content for and not just trying to go super, super wide. It works- Yeah … to an extent, but yeah.

[00:46:25] Nathan: Okay. So something interesting on this. There’s a lot of formats. Let’s see if you did like five AI tools for this or, like, this, the versus that or, um, these are the things that feel kind of gimmicky.

[00:46:35] And I’m always, like, on the line of this because sometimes you wanna try new things, and I think you should, right? Like, it’s, uh, it’s such a low-risk thing to do. Uh, Taki Moore is someone who I think puts out the most interesting content, and I, I love his approach to all this stuff. And he hates it when Dan Martell, who’s one of his close friends, does, like, any formulaic whatever.

[00:46:55] And so Taki will make fun of Dan all the time for this. Now, Dan also has, like, millions of followers, and it’s working and-

[00:47:01] Chenell: Yeah …

[00:47:01] Nathan: whatever.

[00:47:01] Chenell: Definitely working.

[00:47:02] Nathan: But, and so I was talking with Taki, and he was like, “Yeah, this, these formats suck,” all of that stuff. And I was like, “I’ve done some of those.” And in the next conversation, ’cause we’re at an event together, next conversation is the president of one of the largest sporting goods companies, uh, in America, who was like, “Hey, I love that, like, this versus that AI one that you did.

[00:47:22] It was so good. I loved hearing your take on AI.” And it was like- I don’t know what to think. And I was like, you wa- you watch that. Um, one thing that it made me think of though is, like, don’t get … don’t let a, a particular format get in the way of just putting out volume. Mm. Like, ’cause people want to hear your take on it.

[00:47:41] Chenell: Yeah.

[00:47:41] Nathan: It’s an interesting balance of, like, you do want to teach the right things. The whole, like, audience versus crowd. I, I don’t know.

[00:47:48] Chenell: Yeah, no, totally. And, like, the, the format to volume thing, totally. Mm-hmm. Like, if I was trying to put out three deep dives a week, I would not be able to do that. Mm. Right.

[00:47:56] Like, that would be very stressful. But, um, one a week is good, and then you can break that into smaller segments for- Yeah … social.

[00:48:02] Nathan: Yeah, that makes sense. Okay. So diving in. Conversion for money. Mm-hmm. Uh, the audience matters a lot.

[00:48:07] Chenell: Yes.

[00:48:07] Nathan: Um, au- audience or intent.

[00:48:09] Chenell: So this all also tie … These, these kind of tie together because the positioning of how you talk about your paid product is going to- Mm

[00:48:16] really impact this as well. And so this is why I love getting these right first- Yeah … and trying to figure this out.

[00:48:22] Nathan: Does anyone come to mind of, of … or an example of someone really nailing the positioning of their paid product?

[00:48:27] Chenell: I feel like Pat Walls did this really well with Starter Story. Okay. Um-

[00:48:31] Nathan: I don’t even know.

[00:48:31] What is his paid product?

[00:48:32] Chenell: So he had … It, it’s changed,

[00:48:34] Nathan: but- Yeah. Well, I mean, and then he sold the whole business to HubSpot. True. Did quite well, so.

[00:48:38] Chenell: Clearly it worked. It was, like, an annual membership. Mm. And you just … You could read three different, uh, stories, like starter stories.

[00:48:46] Nathan: Yep.

[00:48:46] Chenell: Uh, he would put out, I think, like, 15 a month.

[00:48:48] And you could read- That’s a good amount of volume … three for free a month. And then if you wanted to keep reading more-

[00:48:52] Nathan: Mm-hmm …

[00:48:53] Chenell: you had to pay. And so it was, like, gated content almost. It was kind of like a paid newsletter, but not.

[00:48:58] Nathan: Oh, but what’s interesting is he was able to have … He didn’t have to decide this one is free or paid.

[00:49:04] Right. It was each person gets three.

[00:49:06] Chenell: It was like a metered situation. Yeah. Yeah. And so over time, he started adding in more, um- Mm … things to this paid side of things. So he would add a full database that you could filter based on the different types of businesses- Right … you wanted to study. Um, or he would almost make it like a paid newsletter at the bottom.

[00:49:21] Certain things would be gated. Mm-hmm. And so I think he did this really well because all of his content was just about how do you get started.

[00:49:27] Nathan: Right.

[00:49:27] Chenell: These are ideas for businesses. This is what’s working. Here’s how they grew. And the paid product was just like, “Here’s more of those.” Right. And you can get

[00:49:35] You can go way deeper.

[00:49:37] Nathan: Something that I do like in a paid newsletter or any of this gated content is when the bulk of it is free.

[00:49:44] Chenell: Mm-hmm.

[00:49:45] Nathan: And then the expert, the person who wants the deep dive, wants to go to the paid.

[00:49:49] Chenell: Yeah.

[00:49:49] Nathan: So a great example of this is Sacra. Okay. Which they do these business deep dives.

[00:49:54] And so now they rank for a bunch of things. So, like, um, a friend is interviewing for a job at Attentive, the, like, social media … or the text messaging platform. So I was like, “What is their revenue?” And it’s like Google it. And the Sacra post that comes up, like their deep dive- And they have a lot of information there for free.

[00:50:11] But if you want the graphs and the specifics-

[00:50:13] Chenell: Mm-hmm …

[00:50:13] Nathan: there’s just another, like, 20% –

[00:50:15] Chenell: Yeah …

[00:50:16] Nathan: that requires being, uh, I believe, a paying member. And maybe they give you a few for free if you put in your email address or some- something like that. But it was like they got all the top-of-funnel traffic because it is the best for free, right?

[00:50:28] I can’t believe it’s free.

[00:50:29] Chenell: Yep.

[00:50:30] Nathan: But, like- If you’re an industry professional- Yeah … you’re paying for this because you need to know the specifics and the details.

[00:50:37] Chenell: Exactly. Yeah. Uh, so the ADHD guys, they have a paid newsletter, and most of it’s free. Mm-hmm. And at the bottom there’s, like, worksheets and ways to go deeper and actually im- implement this stuff.

[00:50:46] Right. And that’s what their readers wanted. And so they did that, but they gave it to only the paid users.

[00:50:51] Nathan: Yeah, that’s awesome. And there’s still a ton of value for the free users.

[00:50:53] Chenell: Totally. Yeah.

[00:50:54] Nathan: Okay. Okay, so number five. We made it all the way through the list. What is the fifth lever?

[00:50:59] Chenell: This is the one that I see no one doing.

[00:51:01] Nathan: Okay.

[00:51:03] Chenell: Uh, it’s subscriber experience.

[00:51:05] Nathan: Okay.

[00:51:06] Chenell: You’ve done all this work, you’ve created the content, you’ve positioned it well, you’re driving traffic to it, people are converting. But then they subscribe to your newsletter and it’s almost like crickets, or the experience isn’t great. So examples of this, um-

[00:51:20] Nathan: If you say my newsletter I’m gonna cry.

[00:51:22] I’m just kidding. We’ll get into that later.

[00:51:24] Chenell: Uh, so someone subscribes. The form just says success, and then it’s like- Yeah …

[00:51:31] Nathan: cool. Okay.

[00:51:32] Chenell: These people are the most excited about your content that they will ever be.

[00:51:35] Nathan: Yeah.

[00:51:36] Chenell: And you’re showing them this little green box that says success.

[00:51:39] Nathan: Mm-hmm.

[00:51:39] Chenell: Um, I highly recommend people redirect that to what I call an almost there page.

[00:51:45] Okay. So it’s like- Yeah … you’re almost there.

[00:51:47] Nathan: Mm-hmm.

[00:51:47] Chenell: But actually go check your email, go reply, go do this extra action, whatever that ends up being. And that is just such a better experience for people than success. And it’s like, okay. Right. Now then they just… They might get your welcome email, but maybe they didn’t go to their inbox to check it because you didn’t tell them to.

[00:52:06] Mm-hmm. So I really enjoy this kind of thing. Mine is really corny, and it’s just like me pointing at like, “Hey, you’re almost there, but go click this thing.” Um, so that helps a lot. It also helps with deliverability- Mm-hmm … because they’re replying, they’re taking action. The other thing you can do on the almost there page, um, sometimes welcome emails take two to three minutes to actually go through.

[00:52:24] Nathan: Right.

[00:52:25] Chenell: And so what I have been doing is using Brendan Dunn’s Right Message! and asking questions on that page. Mm-hmm. And so like, do you have a newsletter? How many subscribers do you have? And so getting that first party data to be able to then help them further down the line. Yeah. And like 80% of people finish those questions, and then I’m like- How do

[00:52:46] Nathan: you end up using that data later on?

[00:52:48] Chenell: So that’s how I can get on calls with people, ’cause I’m like- Oh … all right, you have a newsletter. I wanna talk to people who have a newsletter generally. Um, how many subscribers do you have? How long have you been doing this? And so I can use that to get on calls. I can also use that to segment people and sell them products later.

[00:53:03] Right. Or say, “Hey, I have coaching open. You should- Mm-hmm … book a spot.” And so that’s really helpful. And you’re giving them something to do right away, and you’re not just like- Dropping them out into the ether.

[00:53:15] Nathan: Yep. Yeah. I like that. What else matters in subscriber experience?

[00:53:19] Chenell: So once they get to your inbox, you wanna ask them to reply, obviously.

[00:53:24] Okay. Get deliverability signals going. Um, the welcome email is super important, and I think people just kinda phone it in and write it once, and then don’t think about it again for three years.

[00:53:34] Nathan: But- What makes a great welcome email?

[00:53:37] Chenell: Uh, it depends on what your goal is and what you’re trying to do. But generally, like, “Hey, thanks for subscribing.

[00:53:42] Here’s some great content.” Or simple, I like to do a two-step welcome email. So it’s like, “Hit reply and let me know how you found the newsletter.” So then I’m getting them to reply. Mm-hmm. It’s an easy question for someone to answer. And then an hour later or two hours later, I’ll send like, “Hey, here’s how to get started,” or- Right

[00:53:59] “Here’s this thing.” If I’m sending a lead magnet, I can say, “Did you get it? Did you open it? Did you engage with it?” That kinda thing. Um, and just kinda getting people into…

[00:54:08] Nathan: Something that we’re playing with, because, uh, reply automations work so well on Instagram-

[00:54:14] Chenell: Mm-hmm …

[00:54:15] Nathan: we’re playing with doing that in email as well.

[00:54:18] And so actually automating, you know, “Hey, I wrote this…” You know, say in a broadcast, y- I might say, “Hey, I wrote this guide on career growth,” or something.

[00:54:26] Chenell: Yeah. ”

[00:54:27] Nathan: Just reply ‘guide’ and I’ll send it to you.” And obviously you could just have them click a link.

[00:54:32] Chenell: Mm-hmm.

[00:54:32] Nathan: But, like, it’s a different level of engagement of like, oh, I’m actually interacting.

[00:54:36] And then you could send the automated email. Uh, and then you can tag people as having replied.

[00:54:42] Chenell: Yeah.

[00:54:42] Nathan: Um, it obviously helps your deliverability. Yes. Our, our deliverability team was already doing this. When someone brings over a list that in Google Postmaster Tools is, like, mid health, you know, or something like that like, okay, well, we’re gonna have a strategy to generate replies.

[00:54:57] Chenell: Right.

[00:54:57] Nathan: Um, another thing, one of the lead magnets for, uh, the Letters of Wealth book- is an email course on how to build your audience. ‘Cause, you know, chapter 19 in the book is all about how an audience helps you build wealth. And so it’s like, okay, well, let’s break that down. And so it’s a seven-day email course, but if at the end of any email cour- a- any email, if you don’t wanna wait till the next day, you can reply, and it will then send you the next one right away.

[00:55:23] And so like, ooh, am I just generating, able to generate like seven replies, seven votes in, you know, in Google and all of that to be like- Yeah … no, this is a good newsletter. It should then, it should be in the primary tab. It should be-

[00:55:34] Chenell: Totally …

[00:55:34] Nathan: you know, not marked as spam.

[00:55:36] Chenell: That’s awesome. ‘Cause I’ve just been doing this with Zapier.

[00:55:38] Uh-huh. So if someone replies, it tags them as replied. So then I can, like, in Kit say, “Oh, yeah, this person’s more engaged or whatnot.” So- Yeah …

[00:55:46] Nathan: it’s exciting. Yeah, there is, there is an app in the Kit app store coming out that will do exactly this.

[00:55:49] Chenell: Awesome.

[00:55:50] Nathan: Anything else in subscriber experience?

[00:55:52] Chenell: Um, yeah, I mean, there’s a million things here.

[00:55:54] Mm-hmm. So as nerdy as it sounds, I think the internet needs to be a more fun place. And so- … let’s, like, just scrap everything that everyone does right now as like- Yeah … oh, let’s just do the norm. So, uh, there’s a million things you can do. Uh, Caitlin Burgoyne does a good thing where it’s like a reverse lead magnet, so she’s, like, surprising you with something free after you sign up.

[00:56:14] Mm-hmm. Um, I like, there’s a newsletter called 1440.

[00:56:17] Nathan: Yeah.

[00:56:18] Chenell: And, um, after 30 days they’ll send you… Is it 30? No, it’s 14 days ’cause they’re a daily newsletter.

[00:56:23] Nathan: Okay.

[00:56:23] Chenell: They send you an email, and they’re like, “Hey, we’re the founders. We just wanna make sure you’re having a ex- good experience. Like, here’s this extra content or whatnot.”

[00:56:30] And so it’s just, like, coming into the space with surprising people instead of just- Yeah … phoning it in and being like, “Here’s my newsletter.” And so when you can just, like, surprise people, I think that really helps.

[00:56:40] Nathan: One of my favorite books is by Derek Sivers, and it’s Anything You Want.

[00:56:43] Chenell: Okay.

[00:56:44] Nathan: And so he was the founder of CD Baby, which was the first way that musicians could sell music online, basically.

[00:56:50] And they had this incredible, like, post-purchase email, and it w- it just, and if, if anyone Googles it, they can find it, but it’s all about how, you know, they lovingly took your CD off of the shelf. And, like- … people had a moment of silence as it was packed in, and they had a parade through the streets of Portland as they brought it, you know, like, as they brought it to, uh, the post office and all this.

[00:57:12] It’s just, like, this moment of delight.

[00:57:14] Chenell: Right.

[00:57:15] Nathan: And so if you’re like, “Okay, could I add these things all the way through?” And some is gonna be through being unique. Some is gonna be through humor.

[00:57:22] Chenell: Mm-hmm.

[00:57:22] Nathan: You know? Or all of the… Like, a, a humanness would be another element of- Yep. Um, my friend Jason Gaylord does a really good job of, in a lot of his outreach other things, he just sends videos when other people would send emails.

[00:57:34] Chenell: Mm-hmm.

[00:57:35] Nathan: And it’s just like- You, you connect with him. Yeah. And so even, you know, on the thank you page or the almost there page, if there’s a video of you saying like, “Hey, I’m really excited that you joined. When, when I started writing content about growth deep dives years ago, I didn’t think anyone was as nerdy about this as I am, but now there’s 50,000 people reading it.

[00:57:52] I’m love that, you know, you’ve decided to join this community. And so go to your inbox, click the link.”

[00:57:58] Chenell: Yeah.

[00:57:59] Nathan: You know, “I’m so excited you’re here.” Like, like just that humanness goes a long ways.

[00:58:02] Chenell: Totally. Especially in a world of AI, like this is where it’s really gonna stand out, and I think if we can do more of this.

[00:58:07] Yeah. Like just sit down and map out like what would I want my s- my subscriber to go through? Mm-hmm. And it sounds like a lot of work, but once you realize that you can pretty much set it up once- Mm-hmm … and like it runs for every person, it’s not like you have to do it every single time, that’s kind of important.

[00:58:21] Um, another thing with this, James Clear.

[00:58:23] Nathan: Yeah.

[00:58:23] Chenell: His first thousand, I think he said, uh, subscribers, he would actually reply personally to each one. And so you would never expect that- Right … from an author or a writer. And so how can you build in those moments of delight?

[00:58:35] Nathan: Yeah.

[00:58:36] Chenell: Yeah.

[00:58:36] Nathan: Yeah, and I think James learned that from Chris Guillebeau-

[00:58:38] Chenell: Okay

[00:58:38] Nathan: who did that all the way along. And it’s also thinking about like what’s an advantage that you have? ‘Cause obviously you think like, “Okay, James, James Clear today has so many advantages that I don’t have.” Yeah. And it’s like, okay, but what advantages do you have that he doesn’t? It’s like, okay, well, he gets 3,000 new subscribers a day, and I get three.

[00:58:57] Chenell: Yeah.

[00:58:58] Nathan: So I could send personalized videos to every single person.

[00:59:02] Chenell: Mm-hmm.

[00:59:02] Nathan: Right? Or I mean, Chris Guillebeau sent individual emails welcoming, uh- Wow … all of his subscribers up to 10,000.

[00:59:08] Chenell: Okay.

[00:59:08] Nathan: Uh, and so he did it for quite a while. But also if you’re like, okay, you get three a day, eight a day. Yeah. It’s like, um, Justin Walsh was teaching a LinkedIn class at, uh, Mashup-

[00:59:19] Chenell: Okay

[00:59:20] Nathan: um, a couple years ago. And you know, he was talking about how every single day he spends 30 minutes in the comments replying to things. And people were like, “Even on Sundays?” And he was like, “Yeah, man, like- I’ve stumbled in this weird world where I can teach business and marketing and all of that to all of these people and make millions of dollars a year.

[00:59:41] And yeah, no, if the trade-off that I have to make is seven days a week I talk to my community for 30 minutes, even on Sundays, like, yeah.

[00:59:49] Chenell: Yeah. Goes back to, like, volume kind of. It’s like- Yeah. … just do the work. Like, it’s, it feels like a lot, but it’s really not when you sit down and think about it.

[00:59:56] Nathan: Yep.

[00:59:57] Chenell: Uh, something I did recently was go back to, uh, some of the first subscribers that I have and actually sent loom videos to say like, “Hey, thanks for still being here.”

[01:00:04] Nathan: Yeah.

[01:00:04] Chenell: And so, I mean, that just kind of builds that loyalty, too.

[01:00:07] Nathan: There was this moment at Craft and Commerce, uh, I guess a year ago, where I heard a conversation going around of everyone was talking about what their Kit account ID was. Oh. Because the few people, I think John Meese probably started this, who have three-digit account IDs, you know, they’re the, the in the first 999 people to create an account were kind of flexing that on everybody else.

[01:00:28] And so our team was like, “Why…” You know, at the, like, genius bar setup, “Why is everyone, like, asking us to, like, look up what their account ID is?” Someone would be like, “Oh, I’m number 812.” Take that. To think about what’s the time that you’ve done to re- reward your most special customers? Like Justin Jackson, the founder of Transistor, is the longest continuously paying Kit customer of all time.

[01:00:50] He’s at, like, 13 years all the way through. Wow. There’s other people who might have joined before him but stopped paying or keep come back. But, like, he’s the diehard fan. I, I, probably like four years ago, I told him that and like, you know, said thank you in a big way. But, like, what else have you done? You know, of the first thousand customers, I should look this up.

[01:01:08] Of the first thousand-

[01:01:09] Chenell: Yeah …

[01:01:09] Nathan: who signed up, how many are paying today? And like, we should reach out to all of them. And you can do that with your newsletter subscribers and everyone else.

[01:01:17] Chenell: Totally. And again, like, this stuff goes back to figuring out what they need and- Mm-hmm … building content. And so it all just like, it’s not a flywheel- Yeah

[01:01:24] but it all pulls back together, uh, in that way. So yeah, just like- Right … trying to figure out, like, reverse engineer that, like, ideal experience. People think about, like, product onboarding and all that stuff, but rarely do I see people thinking about this with their newsletter.

[01:01:37] Nathan: Another one that I think is gonna happen a lot more is now that Kit has subscriber signals, right?

[01:01:42] You’re getting so much more information-

[01:01:44] Chenell: Yeah …

[01:01:44] Nathan: where you can actually personalize it based on if someone has 10,000 followers or more. You could change the emails that you’re sending. Or you could say, oh, actually, say I’m getting 20 new subscribers a day.

[01:01:56] Chenell: Mm-hmm.

[01:01:57] Nathan: Well, I’m going… Everyone’s gonna go through a flow that I’ve curated and made really good, and then, you know, but the three people or the two people who have o- over a certain follower count, like, I’m going to send them a personalized video.

[01:02:09] Chenell: Yeah.

[01:02:09] Nathan: And you’ll probably make a lot of friends.

[01:02:11] Chenell: Probably.

[01:02:12] Nathan: I think another thing you can do on subscriber experience that’s really, really simple, if you’re just looking for a simple action item, is go subscribe to your own newsletter.

[01:02:20] Chenell: Yes.

[01:02:20] Nathan: And see what the experience is. So I had an experience recently where my son comes and goes, “Dad, you don’t really play soccer.”

[01:02:29] And I was like Yeah, I mean, I used to, but I, I don’t. I haven’t in a long time. I’m a little more into volleyball now than soccer. And he’s like, “Huh, okay.” I was like What, what made you buy that? He’s like, “Oh, I just, I signed up to your newsletter and it says you play soccer.” And he… I went back. Like, in my welcome email, it had, like, things I’m into and all of that, and I said in that, like, I’m really into soccer and all this.

[01:02:52] And then, um, a little while later he goes, um, “I don’t hear you trying to learn to play the piano.” It’s like, “What?” And he’s like, “Yeah, and I- you sent me an email talking about how you were learning to play the piano.” And I was like, “What? Oh, during COVID I, you know, I was stuck at home.” And I was like, “Oh, let me learn.”

[01:03:09] You know, I spent like three months learning to play the piano, and that dropped off and whatever else. But he was referencing the welcome emails that I had written four or five years earlier, and they were still there, and they were unchanged, and they were totally out of date.

[01:03:20] Chenell: Yeah.

[01:03:21] Nathan: And so you’ll catch all of those things, and you can catch them be- you know, yourself-

[01:03:24] Chenell: Mm-hmm

[01:03:24] Nathan: before your 14-year-old son catches them and uses it to make fun of you.

[01:03:28] Chenell: It’s nice to know that the founder of an email marketing company- … has this issue, too. Yeah,

[01:03:32] Nathan: exactly.

[01:03:33] Chenell: But yeah, I think the reply piece of this is so key because at a certain point years in, people are like, “I’m not getting replies anymore,” and like, “My newsletter- Mm

[01:03:41] feels like it’s dying.” And I’m like, “Have you… Did you ask for these from the beginning?” Right. Because I think if you can set that precedence early on, then people will be more likely to reply. They’ll know that- Mm … you’re, you’re there reading it on the other end. And so it’s just, like, really important to do this in the early days.

[01:03:55] Nathan: This was brilliant. I am so excited. But what if we make it a little more tangible? And do you have any notes on how we’d apply this to my newsletter?

[01:04:04] Chenell: Oh, do I?

[01:04:05] Nathan: Oh, fuck, okay. Maybe I wrote a little word that I have. Hey, if you wanna master the skill of making money, make sure to pre-order my book, The Ladders of Wealth.

[01:04:12] It’s gonna help you learn exactly what skill you need next to go from earning a living to building wealth. The book comes out March 2nd, but if you go to ladders of wealth.com right now and pre-order the hardcover, I will send you the full e-book and the audiobook for free, and I’ll get them to you early.

[01:04:28] So go to ladders of wealth.com to learn more. I’d love to get you early access. All right, my newsletter.

[01:04:34] Chenell: You have really good content already. Okay. I don’t… I’m not- You

[01:04:37] Nathan: don’t have to lie to me about

[01:04:38] Chenell: it. No, I think you do. Um, the one thing that I would say is that in your newsletter sometimes you’ll wr- you’ll share a podcast episode- Mm-hmm

[01:04:46] and you give, like, two paragraphs on, like, what’s in the episode.

[01:04:49] Nathan: Mm-hmm.

[01:04:49] Chenell: The thing is that podcast people and newsletter people are not- Are not the same … the same person. Yeah. And so if you can actually give the newsletter reader-

[01:04:57] Nathan: Mm-hmm …

[01:04:58] Chenell: almost as much value as the podcast listener.

[01:05:01] Nathan: Ooh, okay.

[01:05:02] Chenell: So what I’ve seen work really well, uh, for me and some of the people I work with is taking your podcast episode and almost turning it into a blog post or something super valuable that people can get all of the notes and everything from right there without- Yeah

[01:05:16] having to watch the episode. I know YouTube growth is important to you. However, not everybody wants to watch YouTube videos. Right. Um, or listen to a podcast for that. So I think you can really do better with this version. Almost could be taking something out of the episode, writing a full post about that.

[01:05:32] You don’t have to, like, break down every single thing in the podcast- Mm-hmm, yep … but maybe the most important one.

[01:05:36] Nathan: Yeah, ’cause I’m summarizing the whole thing and just saying, “Go watch this.”

[01:05:38] Chenell: Correct.

[01:05:39] Nathan: And Do you feel like that, that detracts from the quality of the newsletter as a whole?

[01:05:45] Chenell: Well, if you put it in there as, like, the main piece of content, I don’t think so at all.

[01:05:49] Nathan: Right. Okay, what do you think about in these issues? So if I flush out the podcast section-

[01:05:55] Chenell: Yeah …

[01:05:56] Nathan: what I could end up with is different topics, right? Yeah. Where I’m saying, “Here’s the, what the main newsletter’s about, and then here’s the second topic.” Yeah. “And then here’s a couple qu- a couple quick links.”

[01:06:06] Does that become too much at that point?

[01:06:09] Chenell: It could be. Yeah. It depends on how it’s done. But I think you send twice a week anyway, right? So maybe once-

[01:06:14] Nathan: Uh, I send once a week that is… So every Tuesday I send a live broadcast.

[01:06:19] Chenell: Yeah.

[01:06:19] Nathan: And then all my automated, like, greatest hits emails go out on Thursday. Got it.

[01:06:23] So eventually you’ll run out of the Thursday emails.

[01:06:25] Chenell: Okay.

[01:06:26] Nathan: Um, but that’s kind of the format to get to twice a week.

[01:06:28] Chenell: Yeah. So I almost wonder if one of them is just the podcast. Mm-hmm. And then the other one is your hot takes or whatever, um, as you’re growing this large company and, like, meeting all these creators and seeing- Right

[01:06:38] behind the scenes.

[01:06:38] Nathan: Something that I think about is… I thought you were gonna go harder on the valuable content, which if you have more takes, I wanna hear them. Scoring my content based on how excited I would be to read it- Mm-hmm … as if it was from someone else. ‘Cause there’s often times where I’m, like, trying to hit Tuesday at 10:00 AM.

[01:06:52] And so I’m like, “It’s good.”

[01:06:54] Chenell: Yeah.

[01:06:55] Nathan: You know, or like, uh, uh, sometimes I’m like, “That’ll be valuable to a beginner,” you know, and hit send. You’re like, “No, but is this something… How often do I hit the I can’t believe it’s free or I would be excited to, to hear this?” Like an episode that we did with, uh, Ben Greenfield.

[01:07:10] Mm. You know, in that episode he breaks down, like, his $5 or $6 million a year business in detail, every revenue stream. How he’s like, “Oh, that’s the small business. Let me tell you about the big business that I’m actually building. Oh, and let me tell you about the business that’s an order of magnitude bigger than that.”

[01:07:26] And, like, that’s the kind of thing where I’m like, “I can’t believe this is on the internet.” And I’m like, I don’t know how often I hit that with the newsletter.

[01:07:32] Chenell: Yeah.

[01:07:33] Nathan: And so trying to recenter on what’s the content that you could only get here that other people aren’t putting out there? ‘Cause I, I think that’s something that works really well for you of, like, growth deep dives on that level just don’t exist out there.

[01:07:44] Chenell: Yeah. And so I almost wonder if, like, the podcast is something you can have live on your website too. Mm-hmm. Like, that full blog post. And you don’t have to put the whole thing in the newsletter. Right. And you can just say, like, “Go read the whole edition.” ‘Cause I actually love doing that. A lot of people don’t give links for people to share with friends.

[01:07:59] Like, I am not- No … someone who would forward an email.

[01:08:02] Nathan: Yeah.

[01:08:02] Chenell: But if you have it living on your website somewhere, I’ll take that link- Mm-hmm … and share it with friends.

[01:08:06] Nathan: Yeah.

[01:08:06] Chenell: And so that could be an option. You, you

[01:08:07] Nathan: would drop it into the group chat or- Yeah … whatever else. Or

[01:08:09] Chenell: link to it from my newsletter in, like, the bottom section- Right

[01:08:12] with like, “Hey, cool” I

[01:08:13] Nathan: hadn’t thought about that of like, “Hey, you’re actually making this harder-”

[01:08:15] Chenell: Correct …

[01:08:15] Nathan: for me to promote your content.”

[01:08:17] Chenell: Yeah. ‘Cause I don’t ever wanna drop somebody into a YouTube video. Mm-hmm. Um, and I’ve, I’ve gotten a lot of replies of people saying like, “Thank you for actually putting this into a blog post format, ’cause I was never going to listen to the podcast episode.”

[01:08:29] Nathan: Mm.

[01:08:29] Chenell: I’m like, “Okay. Thank you.”

[01:08:30] Nathan: But then I, I got hooked, and I got into it, and I might have either gotten the most value or- You know, I was like, “Oh, I’ll click the link to the section-

[01:08:38] Chenell: Yeah …

[01:08:39] Nathan: where they talk about that live.” So we, you were very much in my target demographic. Okay. For, uh, the podcast and, uh, the newsletter.

[01:08:47] Chenell: Yeah.

[01:08:47] Nathan: What else would you like me to cover?

[01:08:50] Chenell: I think if you surfaced some of the learnings of like- Mm-hmm … you were in the room with whoever.

[01:08:56] Nathan: Right.

[01:08:57] Chenell: Here’s, here’s what you’ve learned. And you talk about these- Yeah … on other epi- like, podcast episodes or just, like, randomly in Nathan Barry Show episodes. But if you can actually pull those out into standalone pieces, I think that would be killer.

[01:09:09] ‘Cause I always find out about them, like, happenstance. I’m like, “Oh, I heard, you know, Nathan said this thing.”

[01:09:14] Nathan: Right.

[01:09:14] Chenell: But you’re always in these cool rooms and doing interesting things, and I think if you can showcase that more, that would be really insightful.

[01:09:20] Nathan: Okay, so one thing that we could do with the podcast is we could split it out to a totally separate email.

[01:09:26] Yeah. And send that on Thursdays as well. Like, how would you think about doing that?

[01:09:30] Chenell: I-

[01:09:31] Nathan: Or would you do that? And then if so, how would you implement it?

[01:09:33] Chenell: Yeah, I, I would definitely do that. I think the podcast has so many insights in it- Mm … that are only valuable to the person who’s listening right now.

[01:09:41] Nathan: Yeah,

[01:09:41] Chenell: it’s lost.

[01:09:41] And so if you can break them down into a written piece, like, people who read newsletters generally prefer written word. Mm-hmm. Not always. There are some crossover and outliers, but I think a lot of people who read a newsletter want the written piece. And so if you can share that in a full edition of the email, you could break it out, put it on your e- your website, and then link to it from there.

[01:10:03] Um, yeah, I would definitely do that as a standalone piece. And then you can add, like, interesting links at the bottom- Yeah … or whatever you wanna do, but …

[01:10:10] Nathan: Or graphics, tie it in.

[01:10:11] Chenell: Yeah.

[01:10:12] Nathan: Uh, and all that in more areas. Okay, so that could end up being a, a, an additional email. And you do that as another email, not, like, a separate newsletter.

[01:10:21] Chenell: I would do it as, yeah, an additional email. And then you could split it out, let people unsubscribe from one if they want.

[01:10:26] Nathan: Yeah, that’s a good one of, like, using link triggers or the email preferences to say, “Hey, I wanna get both the highlight or, like, the, the regular Tuesday email and the podcast deep dive,” or opt out of one but not the other.

[01:10:37] Chenell: Yeah. And as a consumer, like, I’ve read podcast breakdowns, and then I go listen to the episode anyway. So it’s not just detracting necessarily from views- Right … or anything. I think if anything, it’s just getting me more excited to go listen.

[01:10:48] Nathan: Okay, so then going back to the The core newsletter.

[01:10:52] Chenell: Yeah.

[01:10:52] Nathan: You wanted to, you know, add more insider lessons.

[01:10:56] Chenell: Yeah.

[01:10:56] Nathan: Um, what do you think of the, like, the longer email that hits on a few different things versus just saying, like, “Here’s what I wanna teach you today,” and that’s it?

[01:11:04] Chenell: I like ha- adding more things- Yeah … because not everyone’s gonna be interested in that main piece. Mm-hmm. And so if you can give people different options in a newsletter, then you get higher click rate and all that stuff- Yeah

[01:11:15] and people are engaged and they’re gonna stick around. So I would, I’d give people more options. But if you do, like, for someone that’s been doing a longer edition and that’s working, like, keep going. Right. Like, stick with the format that is working, but I do like giving people choices.

[01:11:29] Nathan: Yeah. Yeah. That makes sense.

[01:11:31] Okay, what else would you add to make the content of the newsletter more valuable, or what would you change?

[01:11:36] Chenell: Well, I think this is gonna go into- Okay … subscriber experience, but, um, you have a book coming out.

[01:11:41] Nathan: Yes.

[01:11:42] Chenell: And I feel like Right now when someone subscribes for the book newsletter, they just get dumped into your main list.

[01:11:50] Nathan: Mm.

[01:11:50] Chenell: And there’s no extra anything.

[01:11:53] Nathan: Yep.

[01:11:53] Chenell: Um, so this is actually gonna conflict with having two emails. Got it. But it… Maybe you add snippets for people who have joined the wait list-

[01:12:01] Nathan: Right …

[01:12:01] Chenell: that say, “Hey, this week I had a call with James Clear.” Mm-hmm. “We talked about promoting the book this way.” Like, I think you undersell how interesting your life is sometimes.

[01:12:10] Yeah. I mean, you’re doing all this travel. You might as well- Right … take advantage of it. Um, so you can have snippets for people who join the wait list, and actually showcase behind the scenes or give them a story from the book, and just kind of keep that through line so that-

[01:12:24] Nathan: Mm-hmm …

[01:12:24] Chenell: over the next 24-ish weeks until the book launches, there’s…

[01:12:29] it’s staying top of mind for those people.

[01:12:30] Nathan: I guess I could also… It, it doesn’t even have to just be for people who signed up for the book. I can do it for everybody.

[01:12:36] Chenell: You can do it for

[01:12:36] Nathan: everybody. ‘Cause it is the… You know?

[01:12:38] Chenell: Yeah.

[01:12:38] Nathan: So yeah, even what’s happening with the book this week.

[01:12:40] Chenell: Right.

[01:12:41] Nathan: Um, ’cause yeah, I’m, I’m proofing, uh, illustrations, and we’re talking launch strategy, and we’re doing all this.

[01:12:47] We’re planning the largest newsletter tour to promote a book that has ever happened in the history of the internet. So, like, maybe we should talk about that.

[01:12:54] Chenell: Yeah. And, like, you are doing this, and you have all these behind the scenes things. Like, showcase that. Right. You’re trying to get- Mm-hmm … more authors to j- sign up for Kit- Yeah

[01:13:02] I think I’ve heard you guys say. Oh,

[01:13:03] Nathan: yeah.

[01:13:04] Chenell: So start talking about the stuff the authors would be interested, interested in. Right. Which is like, “Hey, we were… We spent six hours picking the paper for the book yesterday.” Or

[01:13:12] Nathan: like- My publisher hates me. ‘Cause that is in fact true.

[01:13:14] Chenell: Yeah. That’d be a great subject line.

[01:13:16] Nathan: Is, my publisher hates me. Yes.

[01:13:18] Chenell: So I think that would be so interesting. Like, I’m not writing a book currently, but I would

[01:13:22] Nathan: read that subject line. In their Asana project, which I’m not in, but Chelsea, who runs everything for me, is, uh, they had a task that said, “Deal with Nathan slash paper.” In case anyone’s wondering like, “Must be great to work with Nathan.”

[01:13:37] It’s not.

[01:13:39] Chenell: Top vote.

[01:13:41] Nathan: Okay.

[01:13:41] Chenell: Oh my gosh.

[01:13:42] Nathan: I like that. All right, where do you wanna go next?

[01:13:44] Chenell: Uh, positioning. I guess we’ll move on from content. Hold on. I have the actual- Let’s do it … what it says on your-

[01:13:51] Nathan: Oh, boy …

[01:13:51] Chenell: website right now. Okay. So-

[01:13:54] Nathan: I’m nervous. Cara’s nervous. I’m nervous. Calum’s nervous.

[01:13:58] Chenell: Current, uh, form and, like, headline on your site says, “Hello, I’m Nathan Barry.

[01:14:03] I’m a creator, author, speaker, designer, and the founder of Kit. Subscribe to get my weekly newsletter and latest articles.”

[01:14:09] Nathan: Mm. Yeah, I would tell people that’s terrible.

[01:14:10] Chenell: That’s pretty bad. Like- You have all of this happening.

[01:14:16] Nathan: Yep.

[01:14:16] Chenell: And you’re leading with, like, the least interesting pieces of it, or at least making it sound the least interesting.

[01:14:24] Um- ‘

[01:14:24] Nathan: Cause you’re right. I’m, I- Lead kind of a crazy life.

[01:14:28] Chenell: Yeah.

[01:14:28] Nathan: And I talk to, on a regular basis, the biggest creators on the internet. Yeah. And there’s some that you’re like, “You know, what can I talk about?” Or that sort of thing. But I do have things where I’m like, “Ooh, Stephen Bartley called me last night, and he…”

[01:14:40] You know, and you’re like, “Okay.” “Well, maybe we could talk about that.”

[01:14:44] Chenell: Yeah, exactly. Um, so I think that is a big piece of it. I often find with positioning, creators bury the most interesting piece- Yeah … like, halfway down the page. And so yours is the same way. Right. It’s actually in your welcome email. It says, like, “I’m building this $60,000,000 company.

[01:14:59] Like, here are the insider insights,” or whatever it says. Yeah. That should be what you lead with.

[01:15:03] Nathan: Right. Like- Yeah.

[01:15:07] Chenell: So I think if we can just make it more compelling, you’re gonna- Mm-hmm … impact the conversion a lot more. Right. Because someone’s not gonna wanna subscribe for, like, “Get the Tuesday newsletter,” or whatever it is.

[01:15:15] Nathan: Nobody cares. And I would tell every creator-

[01:15:17] Chenell: Yes. … that.

[01:15:20] Nathan: Now, my team, it would be, like, quick to jump in and say, “Yes, we’re redesigning the whole site.” You know, we just signed the contract for a new design so that the timing is perfect to fix all of this.

[01:15:29] Chenell: Okay, great.

[01:15:31] Nathan: What other, so positioning things. Yeah. You know my content quite well.

[01:15:35] Chenell: Mm-hmm.

[01:15:35] Nathan: Um, how would you position it? And, like, you know my content well, and you’re in, like, the target market that I’m trying to reach of professional creators and, and all of that. What would you say is the, like, positioning or h- or how would you describe, you know, my content to someone else- Um … if they’re trying to get signed up?

[01:15:53] Chenell: Yeah. I think it would be something like insider lessons from- Mm-hmm … the CEO building a $60,000,000 email marketing company or-

[01:16:00] Nathan: Mm-hmm …

[01:16:00] Chenell: something along those lines. And you can A/B test these and figure out which one’s actually working better.

[01:16:04] Nathan: Right.

[01:16:05] Chenell: Because some are gonna resonate- Yeah … and some won’t. Um, so I think A/B testing is a really powerful thing when we’re thinking of positioning.

[01:16:12] But, yeah, just lead with the most exciting pieces of it. Yeah.

[01:16:16] Nathan: What’s your reaction to the where professional creators go to learn to build wealth? Does that resonate with you or not really?

[01:16:22] Chenell: I don’t… Not really. It doesn’t.

[01:16:23] Nathan: I think it’s one of those things where it’s either, it’s either a yes, like, or, like, a hell yes or-

[01:16:27] anything less than that is like, “No, I don’t think so.”

[01:16:29] Chenell: Yeah. I think the concept behind it is good, but the actual phrasing is not. The

[01:16:34] Nathan: phrasing, yeah.

[01:16:34] Chenell: Yeah.

[01:16:35] Nathan: Okay. We’ll work on it then.

[01:16:36] Chenell: Okay.

[01:16:36] Nathan: I like it. I think another thing that to tie in, this is hard for a lot of creators who don’t want to brag or they’re not, you know…

[01:16:45] There’s, like, the category of the, like, the Lamborghini in the library garage, you know. What’s that? Tai Lopez. Tai Lopez. Oh. There we go. Right. You know, people don’t want to… They’re not trying to create that.

[01:16:56] Chenell: Yes.

[01:16:57] Nathan: And, and so then they end up saying like, “Oh, I don’t want to have the photo reel of me with famous creators or the, um, you know, flaunting wealth or success in some way.”

[01:17:07] And so then they end up downplaying it so much.

[01:17:09] Chenell: Right.

[01:17:10] Nathan: But, yeah, that’s the thing that I’m trying to figure out of the balance of, like- Have done a lot and have a lot of success. Also, I’m just a guy from Idaho who has a farm and- Right … you know, likes to build random projects with his three boys, you know?

[01:17:24] Chenell: Yeah.

[01:17:24] Nathan: And so walking that line I think is difficult.

[01:17:27] Chenell: I could see that. I think if you can just position it in a way of like, “Hey, I’m also human, but-”

[01:17:31] Nathan: Right … ”

[01:17:31] Chenell: yesterday I was on the farm and today I’m in, you know, New York-” Yeah … “at Kids Studios with X person.”

[01:17:37] Nathan: Right.

[01:17:37] Chenell: I think that’s kind of interesting, and it, like, humanizes you in a way.

[01:17:40] Yeah. I

[01:17:40] Nathan: like that.

[01:17:41] Chenell: But it is true, like positioning can go wrong. Mm-hmm. Like, you can make it sound so good, and then on the back end you don’t actually deliver on that promise, and that is a recipe for disaster. So yes, I’m glad you brought that up.

[01:17:53] Nathan: That’s good. I was talking to my son yesterday, and, uh, we were just talking about expectations.

[01:17:57] You know, like it’s a… I don’t know if it’s a great quote or whatever, but the, uh, the secret to happiness is, um, low expectations. Which is not actually, ’cause if you have low expectations you probably have low ambition, and that’s not a good recipe. But that promise and expectations versus what’s delivered is such an interesting thing of like you want to make big promises that you can very clearly exceed and over deliver.

[01:18:21] And that’s what you’re saying of like in the subscriber experience, the reverse lead magnet or the extra thing of going above and beyond.

[01:18:27] Chenell: Yeah.

[01:18:28] Nathan: It’s an interesting balance where you have to say like, “No, you really wanna subscribe ’cause I’m gonna give you this,” and then you have to make sure that you can exceed that bar by a lot.

[01:18:36] Chenell: Totally. Yeah. So under promising and over delivering is- Mm-hmm … is a great way to be. Yeah. All right. So momentum. I think-

[01:18:42] Nathan: Yeah …

[01:18:42] Chenell: my biggest note is right now at the end of every podcast you’re like, “Hey, if you love this episode, go to YouTube and subscribe- Yeah … and comment.” I have personally heard that so many times, like I don’t even realize it’s- Right.

[01:18:54] ‘Cause

[01:18:54] Nathan: it’s, it’s almost exactly the same every time.

[01:18:56] Chenell: Yeah. It’s just bla- I don’t even hear it anymore-

[01:18:59] Nathan: Yep … ‘

[01:18:59] Chenell: cause I’ve heard it so many times. I think if you really want to build out your email list- Mm-hmm … like you should probably be link- linking people to the email list. Um- Yeah … something that’s working super well, when I was doing podcast episodes on YouTube, we would create a custom lead magnet.

[01:19:14] Now, you don’t have to do this for every episode, but we were creating a custom lead magnet. And six minutes in I would jump in and be like, “Hey, did you just hear them say that thing? Go subscribe and I’m gonna give you the full breakdown of how they did it.” Um- Yep … and those are-

[01:19:27] Nathan: Right. I don’t run ads in my newsletter.

[01:19:29] Or, sorry, in my… Well, newsletter. I don’t run ads in my podcast. Right. And so I can run ads for my own newsletter. Correct. Yeah.

[01:19:37] Chenell: And so those are converting, like, it was 3.5% of views would become subscribers. And so, I mean, your channel at this point has, like 1.2 million views on YouTube. Mm-hmm. If you converted some of those, that’d be like 30 something thousand subscribers easy.

[01:19:53] And you already have-

[01:19:53] Nathan: I could use another 30,000

[01:19:55] Chenell: subscribers. That’d be good. I… Yeah. I think we all could.

[01:19:58] Nathan: Yeah, so the in-episode promo. The other thing that you could do is obviously a new lead magnet every week would be insane.

[01:20:04] Chenell: Mm-hmm.

[01:20:04] Nathan: But we c- you could work towards Or lead magnets, probably with content that I already have- Yeah

[01:20:10] because I’ve been doing this for a minute.

[01:20:12] Chenell: Yeah.

[01:20:13] Nathan: Um, and then, then within categories, right? So there’s one about growth, there’s one about wealth, there’s, you know, w- like you get to four of them.

[01:20:21] Chenell: Yep.

[01:20:22] Nathan: And then just decide which one you wanna promote. And then the other key thing I would, I think would be recording different intros talking about them.

[01:20:31] So maybe I have the one about wealth. Maybe I record five different-

[01:20:36] Chenell: Yeah …

[01:20:37] Nathan: times of me talking about it. ‘Cause you can totally… The moment the g- the, or the host launches into the exact same words about the exact same thing, you’re like, “Plus 30 seconds.”

[01:20:43] Chenell: Yeah. ‘

[01:20:44] Nathan: Cause I’ve heard this before.

[01:20:45] Chenell: Yep. Yeah, exactly.

[01:20:47] Nathan: Versus the, oh, you’re talking about the thing I’ve heard about, but in a new way. I’m listening. Maybe I do actually want that this time.

[01:20:53] Chenell: Yes, exactly. And so you could also, not to make more work, but you could do different ones for people listening on Spotify and Apple versus YouTube. Mm. And so if they’re on YouTube, you could say, like, “Go comment.”

[01:21:04] But if they’re on podcast, you can say- Right … “Actually, you should go-”

[01:21:07] Nathan: I mean, it’s like 10 more seconds of work for me to read off a teleprompter and talk about it. It’s way more work for the editors, but, you know. That’s what we pay them for.

[01:21:16] Chenell: But yeah, I think this is your biggest piece of leverage. Okay.

[01:21:19] And then Instagram.

[01:21:21] Nathan: Yeah.

[01:21:21] Chenell: Yeah. I’m just gonna reiterate what Gannon said about like- … hey, we should have, um, many chat automations happening. You’re already on Instagram. You have almost 20,000 followers there.

[01:21:32] Nathan: Mm-hmm.

[01:21:33] Chenell: Probably should be driving people to the email list or a specific podcast episode, whatever it is.

[01:21:38] But-

[01:21:38] Nathan: Right …

[01:21:38] Chenell: yeah, I think.

[01:21:39] Nathan: Yeah, I mean, that… I could do a reel about, like, taking a page out of Sam’s, uh, playbook.

[01:21:44] Chenell: Yep.

[01:21:45] Nathan: Do a reel about, you know, a particular topic and just say like, “Oh, here’s the, the biggest money lessons that I’ve learned. Comment ‘money’ and I’ll send you the playlist-

[01:21:55] Chenell: Exactly …

[01:21:55] Nathan: of those episodes.”

[01:21:56] Chenell: Yeah. You could go a step deeper and actually turn it into, like, a post and just link out to the episodes from specific- Oh, that’s true … sections.

[01:22:03] Nathan: Yeah.

[01:22:03] Chenell: A little more work, but I think it’d be more valuable. But then

[01:22:05] Nathan: that makes it very shareable for someone else-

[01:22:07] Chenell: Yeah …

[01:22:07] Nathan: who would then say, “Oh, I dove into this.

[01:22:08] Let me put it in the group chat. Let me post it on X.”

[01:22:10] Chenell: Right.

[01:22:11] Nathan: Or that kind of thing.

[01:22:12] Chenell: The other thing, um, you have an interesting backstory, which I didn’t hear until, like, more recently when you were promoting the book and stuff, um, of, like, being homeschooled and graduating- Uh-huh … when you were 15 and, like, that should…

[01:22:22] You, you should have a start here post.

[01:22:24] Nathan: Okay.

[01:22:25] Chenell: That’s like, “Hey, I’m Nathan.”

[01:22:27] Nathan: Yeah. ”

[01:22:27] Chenell: Here’s where I started. I’m writing this book. Comment ‘wealth’ and I’ll send you the link to sign up for the waitlist,” or whatever.

[01:22:34] Nathan: Right.

[01:22:35] Chenell: Or go pre-order it.

[01:22:36] Nathan: Um, yeah, no, I, there’s a lot of things that I do that people are like, “I’m sorry, what?

[01:22:42] You you were 17 when you dropped out of college?” I’m like, “Yeah, but I got two, two full years in.” Yeah. You know? Like, this does not make sense.

[01:22:49] Chenell: But it’s like, I’ve known you for a little bit, and I had no clue of that. Mm-hmm. So I think that’d be interesting to do.

[01:22:53] Nathan: I love those. On to the momentum. I’m gonna go implement those.

[01:22:56] Let’s talk conversion. I feel like you might have some, some thoughts here.

[01:22:59] Chenell: So it just ties back to the positioning with, um, the headline. I have a feeling you could convert a lot more people-

[01:23:06] Nathan: Mm-hmm …

[01:23:06] Chenell: into subscribers from the homepage. Yeah. You don’t have a dedicated newsletter page that you can drive people to.

[01:23:12] Nathan: Yep.

[01:23:13] Chenell: And then inside the articles and stuff that you’re writing, there is an- another, like, join my newsletter type of form. I don’t even think it says the, “Hey, I’m Nathan.” It just says like, “Get the weekly newsletter.” Oh, you have a lead magnet. It’s like audience building episodes or something.

[01:23:31] Nathan: Yeah. That sounds right.

[01:23:32] Chenell: Yeah. But in the form it says, “We’re dropping a video that has all of these in there. Sign up to get it. It’s not gonna be on the feed, but sign up to get it,” like the private viewing of it- Yeah … or whatever. And I feel like that was a while ago.

[01:23:45] Nathan: A while ago maybe. I haven’t delivered on it. So- I think I was trying to do like a podcast to email-

[01:23:49] Chenell: Yeah

[01:23:50] Nathan: situation.

[01:23:50] Chenell: I imagine.

[01:23:51] Nathan: Yep. Okay. Yeah. So revisit the lead magnets. Yeah. ‘

[01:23:54] Chenell: Cause I was like, “Oh, they have a lead magnet. That’s awesome.” And then I was like, “Oh, okay, maybe not.”

[01:23:58] Nathan: Didn’t actually get it. Coming soon, for three years.

[01:24:01] Chenell: So that could be improved, but, um, if you have, like, conditional lead magnets on different posts- Mm-hmm

[01:24:07] like maybe you have three or four lead magnets like we were just talking about with the different email or the- Yeah … podcast episodes. Um, if you can create those as lead magnets, and then in a post that you’re talking about wealth, like either, “Hey, go sign up for the book,” or, “Get this, uh, lead magnet,” or a mix.

[01:24:24] Nathan: Yep.

[01:24:24] Chenell: Um, so I think if you can do that you’ll increase the conversion there too. Yeah.

[01:24:28] Nathan: Sounds good. Okay. You wanna go to subscriber experience?

[01:24:31] Chenell: Do you?

[01:24:34] Nathan: Oh, here we go.

[01:24:36] Chenell: So I know as the founder of Kit, um- … you wanna showcase all of the things that Kit can do.

[01:24:41] Nathan: Yeah, exactly.

[01:24:44] Chenell: Uh, you definitely are using, like, when somebody subscribes it’s just like,

[01:24:48] Nathan: success.

[01:24:49] Success. There we go. All right. The thing that we’re talking about, oh, we would never do that. Yeah, no. I’m doing it. Yeah. Okay. Look, I just really care about success.

[01:24:58] Chenell: Yes.

[01:25:00] Nathan: It’s a subtle hypnotism thing that I’m doing with the audience where they … I just want them to a- associate my content with success.

[01:25:07] Chenell: Is that right?

[01:25:07] Nathan: No. Okay.

[01:25:10] Chenell: Okay.

[01:25:10] Nathan: Yeah. So, uh, implement the almost there, uh, page.

[01:25:15] Chenell: Yeah. Which would be perfect for launching your book.

[01:25:20] Nathan: Right. ‘

[01:25:20] Chenell: Cause you can say-

[01:25:21] Nathan: We can do a survey. We could…

[01:25:22] Chenell: Oh. Who are you?

[01:25:23] Nathan: Yep.

[01:25:23] Chenell: Like, are you working full, are you a professional creator? Are you just getting started?

[01:25:28] Nathan: Mm-hmm.

[01:25:29] Chenell: That kind of thing.

[01:25:30] You’re gonna learn so much more about them. I know that Subscriber Signals is awesome, but it’s not gonna give you everything.

[01:25:34] Nathan: Yep. And so- And you can have both sources.

[01:25:36] Chenell: Yeah, totally. And so if you can figure out what their biggest pain point is right now- Mm-hmm … that’s gonna be huge, because then you can promote the book, or you can promote the podcast.

[01:25:44] Right. Or Kit or whatnot. So I think getting that information from them right then is gonna be really impactful. Right now after they see Success, then they see the- Important, confirm your subscription email

[01:25:57] Nathan: Oh, it’s the default one.

[01:25:58] Chenell: Yeah.

[01:25:59] Nathan: Oh, no.

[01:25:59] Chenell: Yeah.

[01:26:00] Nathan: Oh, no. That’s terrible. Okay. Um-

[01:26:05] Chenell: Custom welcome email, I would say.

[01:26:07] I mean, you have the welcome email after that point, but you’re also using double opt-in.

[01:26:11] Nathan: Right. So actually use it.

[01:26:13] Chenell: Right.

[01:26:14] Nathan: Yep.

[01:26:14] Chenell: So we had, uh, me and Dylan had Dave Kline and his wife Mara on the podcast, and they… I was talking to them about double opt-in, and they had 45,000 subscribers on their email list, and in their pending list it was 57,000 people.

[01:26:27] And so their pending subscribers- Yeah … ’cause they had double opt-in on, was almost double. And so it’s like, yeah.

[01:26:33] Nathan: And the way… And we have, um, automation templates inside of Kit for this.

[01:26:37] Chenell: Mm-hmm.

[01:26:37] Nathan: Just what you do is you just look for a certain success or engagement mea- metrics. Yep. And then if they don’t hit that within two weeks, you unsubscribe them.

[01:26:45] Chenell: Yep.

[01:26:45] Nathan: The only downside of that is you will end up sending emails to more, uh, typos, or you’re a little more open to list bombing. But Kit has two things built in. One, it will autocorrect your typos and suggest that to the subscriber of like, “I don’t think you meant gmail.con.”

[01:27:01] Chenell: Yeah. ”

[01:27:01] Nathan: I think you put an M in there instead.”

[01:27:03] And then the other thing is for list bombing. So as long as you’re using Kit forms, it will detect any bot behavior and try to prevent that as well.

[01:27:11] Chenell: Yeah. It’s- So I like to use a, a false double opt-in after. Mm-hmm. So it’s not a real double opt-in. It still looks like it. You’re still asking them to click- Mm-hmm

[01:27:17] or reply or get that engagement metric going. But if they don’t click that one email, you can still email them again. Yeah. Whereas with double opt-in, you’re kinda like dead in the water and you can’t really do anything. Right. So that’s big. I think that-

[01:27:29] Nathan: Yeah …

[01:27:30] Chenell: would impact some things. I’ll write that down.

[01:27:31] Nathan: Um, you do need to make sure in your subscriber, in, in your intent around it, that you’re, from a GDPR perspective or whatever, you’re getting your, your permission basically. Your consent. Right. There’s the word. Oh,

[01:27:42] Chenell: yes. There you go.

[01:27:42] Nathan: Uh, a lot of times people will use the double opt-in email to get that consent.

[01:27:47] Okay. And so you would need to make sure that you’re getting it somewhere else in the flow, either earlier on or all that. Or segmenting based on country. But it’s… You c- there’s a lot that you can do there.

[01:27:56] Chenell: Yeah. There’s a big piece of this, and having the welcome email come up and say like, “Hey, I’m Nathan.

[01:28:02] Here’s all…” You know. Yeah. Like a better welcome email. Uh, with the Letters of Wealth list, we have double opt-in on there too. And when you sign up, you’re supposed to get a free chapter of the book. When you click that link, you do get a free chapter, but then you never send it again. And so what I would recommend is probably sending it four hours later or the next day and say, “Hey, did you read the chapter?

[01:28:24] If not- Mm … you might have fallen off or closed the tab.” Yeah. “Here’s the link again. Hit reply and let me know what you’re thinking about it,” that kind of thing.

[01:28:32] Nathan: Yeah.

[01:28:32] Chenell: Yeah.

[01:28:33] Nathan: Okay. That’s good.

[01:28:35] Chenell: Yeah. And then like we talked about, just like getting snippets for book readers- Mm-hmm … or getting them that behind the scenes.

[01:28:41] Like, you do live an interesting life, and I think if you can convey the- Yeah … behind the scenes of trying to get the bestsellers li- list or whatever- Yeah … it’s gonna be big.

[01:28:49] Nathan: Right.

[01:28:49] Chenell: So like it all just like comes full circle back here.

[01:28:53] Nathan: Yep.

[01:28:53] Chenell: Yeah.

[01:28:54] Nathan: I like that. Well, I think it goes to show that, uh, no matter how much ti- how- however long you’ve been in the game, however much expertise you have, like you have to go, like, secret shop your own stuff.

[01:29:06] Chenell: Yeah.

[01:29:06] Nathan: Otherwise, you’re… There’s just so many opportunities.

[01:29:09] Chenell: Yeah.

[01:29:09] Nathan: And so that, I mean, that gives me a lot of confidence that every single person watching this episode could go through and be like, “Can I do it all? Oh, God.”

[01:29:17] Chenell: Yeah.

[01:29:17] Nathan: Okay. You know? And-

[01:29:19] Chenell: Yeah …

[01:29:19] Nathan: find a lot to fix.

[01:29:21] Chenell: And this is only if we’re pretending that we only have one form on our email.

[01:29:24] Sometimes you- Right. Yeah … duplicate a form, and you don’t end up putting all the automations linked back to that.

[01:29:30] Nathan: Yeah.

[01:29:30] Chenell: So you could be, you know, checking every single form, and it’s a lot of work. Right. But you might be missing some things.

[01:29:36] Nathan: It’s also a good time if you’ve been creating for a while. It’s a good time to go through and clean up a bunch of stuff, ’cause often an automation or a workflow that was really important five years ago just doesn’t matter to you now.

[01:29:46] Yeah. And you’re like, “Oh, they could actually just go right into the main sequence.” Yes. That’s fine.

[01:29:49] Chenell: Exactly.

[01:29:49] Nathan: Okay, so the last thing that I wanna hit is monetization. All right. What are some of your favorite ways that you’ve seen from studying all of these creators on how people monetize?

[01:29:57] Chenell: One of my favorite ones was the most innovative that I’ve seen which was how Sahil Bloom is- Mm-hmm

[01:30:03] turning all of his cost centers into profit centers.

[01:30:05] Nathan: Yes.

[01:30:06] Chenell: And so he was paying someone to help grow his newsletter. And now, you know, that business exists of like, let’s actually do this for other people. And now we don’t have to pay, and we’re making money from that. And so he has this huge audience of, some portion of which are gonna wanna grow an email list as well.

[01:30:22] And so he can now turn around and be like, “Hey, if you wanna grow your email list, we have, uh, Paperboy Studios-” Yep … which does paid ads and all that stuff for newsletters. I think that’s just like a huge piece of it.

[01:30:32] Nathan: The thing that I love about services, I’m just gonna put three dollar signs here. Because the average revenue per customer is really, really high.

[01:30:39] And so you don’t actually need that many customers.

[01:30:41] Chenell: Right.

[01:30:41] Nathan: Um, they need to be a high quality customer.

[01:30:43] Chenell: Yeah.

[01:30:43] Nathan: But um, you know, that can end up being really good. I’ll throw out one of mine that’s also a high dollar sign one, um, and that’s Deal Flow.

[01:30:52] Chenell: Okay.

[01:30:53] Nathan: Um, and so if you think of- Like some of these newsletters in the investing startups, um, space like, like that.

[01:31:01] To a venture capitalist, getting the right startup in that wants to take on funding is worth really a lot. And so if you think about a lot of these VCs like, um, uh, Tomas Tunguz or, um, Jason Lemkin or others, by putting out all this content they’re getting attention, and that gets them deal flow that no one else has.

[01:31:19] They’re able to invest in these startups and, you know, with their reputation and everything else. And so they’re, you know, they end up owning, you know, 10% of these massive companies or these things, and it came down to how they monetize their content. Uh, and so that also, you, you, you brought up, um, Mario with The Generalist, right?

[01:31:37] Yeah. As he’s investing, he has deal flow that others don’t. Uh, Packy McCormick is the same thing. Yep. Right? With Not Boring. Um, and so that’s also a very high, high dollar one.

[01:31:46] Chenell: Speaking of Packy McCormick, I actually love taking the content you’re already creating and- Mm-hmm … turning that into, like, a sponsored piece.

[01:31:51] Mm-hmm. So Packy does these sponsored deep dives, which he can charge 5 to 10X a regular sponsor spot, and he’s essentially creating the content he already enjoys creating, but now he’s getting paid five to 10 times more for that.

[01:32:05] Nathan: Yep.

[01:32:06] Chenell: Instead of it just being, like, a free piece of content. And he’s still keeping…

[01:32:09] Like, he has guardrails to say, like, “You don’t get say in what goes in here.” Right. “You’re just buying the piece, and I get to do the content.”

[01:32:16] Nathan: I’ve seen a lot of companies before they go out and raise funding go do Pa- have Packy go do a deep dive on their business.

[01:32:21] Chenell: So smart.

[01:32:21] Nathan: And I, I think the numbers on it, like, like, it’s way more.

[01:32:25] When I heard it, I… And I probably shouldn’t say publicly how much they cost, but it was, like, five times as much as I would’ve guessed.

[01:32:32] Chenell: Okay.

[01:32:33] Nathan: Like, like, whatever number you’re thinking, put a zero on the end.

[01:32:36] Chenell: Yeah.

[01:32:36] Nathan: And that’s, um,

[01:32:38] Chenell: yeah. But he’s built an audience of, like, 300- Oh, yeah … 500,000 plus people.

[01:32:41] Nathan: And it’s worth every penny.

[01:32:42] Absolutely. People talk about how it made their fundraising process or whatever all so easy. Uh, and they’ll link to it. Think about, um, like, a conversion point. If you’re doing outreach, let’s think about, like, building a company, the most important conversions would be getting customers, uh, recruiting a team, and probably getting investors.

[01:32:59] Chenell: Mm-hmm.

[01:33:00] Nathan: So particularly in recruiting a team and investors, it’s one-on-one of like, “Hey, we’d love to have you join the team. If you wanna learn a little bit more about the business…” Aki McCormick did a full deep dive on the company, and you can… Like, your conversion rate of closing that candidate, like, just probably went up 10, 20%- Yep

[01:33:15] off of that one thing, and so that’s, that’s worth a lot.

[01:33:18] Chenell: Totally.

[01:33:19] Nathan: Another one that I’m seeing really a lot, you know, we’re in the high dollar value one, um, is group coaching. ‘Cause that’s where, you know, you can get, whether you’re charging $1,000 for a 90-day, um, accelerator or, um, even way more than that.

[01:33:33] Like, a good example of this, um, would be Dustin, uh, who, uh, Seven Figure Leap.

[01:33:39] Chenell: Yes.

[01:33:40] Nathan: Right? And so he’s teaching people how to grow their brand and audience and all that through guest posting. I think he charges $10,000 for a 90-day-

[01:33:49] Chenell: Yep …

[01:33:49] Nathan: accelerator. Does that sound right?

[01:33:50] Chenell: That’s exactly right.

[01:33:51] Nathan: And we were joking about, at the last Craft and Commerce, about how…

[01:33:56] We, we had made a comment about, like, once people hit about 3,000 to 5,000 subscribers, that’s when they typically can build it into a business and all that. And he’s like, “You know, man, I, I hope to make it to that one day and prove that this is a business.” Everyone knows that Dustin’s making millions of dollars a year- Yeah

[01:34:11] off a 3,000 subscriber email list because of his, like, group coaching accelerator offer.

[01:34:17] Chenell: Yeah. And similarly, like, you, you just talked to Layla on the podcast. Mm-hmm. And so she’s kind of hybridizing. It’s like- Services and- … asynchronous services, but it’s also the same dollar price of, like- Right … “Hey, I’m gonna get on a call.

[01:34:28] I’m gonna show you exactly what to walk through in my content.” Yeah. Instead of giving them a course, she’s like, “No, no, go watch these lessons.” And so she’s just, like, tripling the revenue- Right … based on that.

[01:34:38] Nathan: Um, I’ve seen more and more people take that approach. It’s actually a joke. There was a creator years ago.

[01:34:43] He, he doesn’t put out as much content, um, anymore. It was Patrick McKenzie. And you… Uh, his handle online was patio11. And he ended up working for Stripe for a long time, and, um, really brilliant guy. But he put out a whole course on, like, pricing and packaging. And I don’t know, it was 500 bucks to buy. And if you ran a software company, like it was very, very worth your, your money.

[01:35:04] And people would bring him in and pay him like $30,000 to do a consultation on that. And he’s like, “It’s basically like a dramatic reading of the course, but like personalized,” you know? But they were thrilled to do it.

[01:35:15] Chenell: Yeah.

[01:35:16] Nathan: And so like that element is, is so important. And I’ve seen it over and over again where you become known as the person in the industry.

[01:35:23] And it’s like, “Oh, well we’re not getting random advice from a podcast on how to grow a newsletter. We brought in Chanelle and we paid her $25,000 to do a deep dive with us for a day-

[01:35:32] Chenell: Right …

[01:35:33] Nathan: you know, on how to do that.” And a lot of companies are happy to pay that.

[01:35:36] Chenell: Yeah. ‘Cause it’s custom- Mm-hmm … and you’re able to like pull off your experience of what you’ve seen.

[01:35:40] Like I’ve seen thousands of newsletters. Right. So off the top of my head, I can generally say like, “Actually, you should go do this thing instead of this other thing.”

[01:35:46] Nathan: Yeah. And we can also… We can say, “Okay, I wanna do this.” And you’re like, “Yeah, here’s why I wouldn’t.”

[01:35:49] Chenell: Right.

[01:35:50] Nathan: And dive in. All right. Um, what are some of your favorite monetization methods that are a lower ticket?

[01:35:56] You know, if we’re, if we’re talking, you know, in the 10 to $100 range or, or sub $500.

[01:36:00] Chenell: I was gonna go with like memberships and community- Mm-hmm … but they’re generally not that low.

[01:36:05] Nathan: Yeah. Well, well let’s… What’s wrong with that one? Um- Okay … how would you price it? Or what are you seeing?

[01:36:10] Chenell: Well, with memberships and community, I feel like if you can charge around 1,000 to $1,500- Mm-hmm

[01:36:16] I feel like that’s- Per

[01:36:16] Nathan: year?

[01:36:16] Chenell: Per year. Yeah. Okay. For-

[01:36:17] Nathan: Why that price point?

[01:36:19] Chenell: Because it’s high enough that you’re not gonna bring in the people that shouldn’t necessarily be in there. And again, this is contextual. Like maybe- Yeah … you need a lower ticket for the starters in your audience- Yeah … and that’s great.

[01:36:28] But-

[01:36:29] Nathan: Or if we’re teaching knitting, it might be a different price point than if we’re teaching like-

[01:36:31] Chenell: Correct …

[01:36:32] Nathan: Facebook ads for large e-com brands.

[01:36:34] Chenell: Right. Right. Right. But I feel like if you can get somewhere around here, it makes it as exciting for you as the creator to keep putting- Mm-hmm … money into it and investing your time.

[01:36:42] And for the person actually paying for it, they’re actually gonna put their time and energy into- Yeah … utilizing the space- Mm-hmm … and being a good member and those kinds of things. Uh, when they’re like $200 a year memberships, it’s like, well, it’s just kinda like one of those line items that you can write off and just-

[01:36:55] Nathan: Yeah

[01:36:56] Chenell: “Well, I’ll just… I’ll try again next year.” Right. But keep paying for it, so.

[01:37:00] Nathan: Yeah. And you’re not making enough money to really, as the creator or the c- you know, the person running the membership or community, to really dive in and invest in the success of each person.

[01:37:09] Chenell: Right.

[01:37:09] Nathan: Whereas here, you really could.

[01:37:11] And you could say like, “Oh, this-” This group of people are kind of falling off. Like, I can send personalized video messages to them.

[01:37:18] Chenell: Right.

[01:37:18] Nathan: Or I could suggest, “Hey, this piece of content that was posted in the community the other day, like, I think this is relevant for you.”

[01:37:24] Chenell: Totally.

[01:37:25] Nathan: Yep. What else?

[01:37:26] Chenell: Paid newsletters, should we talk about them?

[01:37:28] Yeah.

[01:37:28] Nathan: We can do-

[01:37:28] Chenell: do it. I, I feel like they are good for a s- the right kind of business. If you are heavily invested in the content that you’re creating and that is the thing, I think a paid newsletter can be a great way to monetize.

[01:37:40] Nathan: Yep.

[01:37:40] Chenell: The other piece of this is that most paid newsletters are, well, for creators, are on Substack.

[01:37:46] Mm-hmm. Tom Orbach, the guy we were talking about with marketing ideas, he has a paid newsletter. He started it when he was at 50 or 40,000 subscribers, and he said once he flipped on paid, his growth for the free side of things doubled. Oh, interesting. And so I think Substack is just, like, heavily investing in the people that are- Mm-hmm

[01:38:02] making them money. ‘

[01:38:02] Nathan: Cause yeah, it’s the only way they

[01:38:04] Chenell: make money. They take 10%, and so he is now showing up higher in- Mm-hmm … some of those recommended feeds and that kind of thing. So his newsletter has exploded. He went paid, um, in April of 2025, and now he- that was at 40,000, now he’s at 101.

[01:38:16] Nathan: Wow.

[01:38:17] Chenell: And so he’s just

[01:38:18] Yeah.

[01:38:18] Nathan: So yeah, I think that we touched on a few important elements of this, and I think that if you There’s one format that I hate and one format that I love. So if you are… I- if it’s, like, the free newsletter and the paid newsletter, and they’re two different options, and you’re always trying to decide, is, does this, this is my best piece I’ve written all month or all year, so it should be paid.

[01:38:42] Chenell: Right.

[01:38:43] Nathan: Like, well, that’s, that’s gonna hamper your growth.

[01:38:45] Chenell: Totally.

[01:38:46] Nathan: Or it’s like, this is so good, I want it to drive growth, and so it should be free, right?

[01:38:51] Chenell: Yep.

[01:38:52] Nathan: Uh, and so you’re like, you have this back and forth. And so I think if you can find a format, if either one or two things are, are true. You either are very prolific, and so you’re like, “Please, I’m gonna put out lots of great content, and this is not my one shot at growth.”

[01:39:07] Chenell: Yeah.

[01:39:07] Nathan: And I’ve got tons of great stuff that’s free, and stuff that’s r- that’s great that’s paid. I think that works really well. Or if you do kind of what we talked about, where there’s, like, lots of really good content, and then some additional thing is paid only.

[01:39:24] Chenell: Mm-hmm.

[01:39:25] Nathan: Right? And so it’s like, it’s 80% free.

[01:39:28] Oh, but you want the d- you want the template to do it? Yeah. Well, obviously, that’s for the paid newsletters.

[01:39:33] Chenell: Yes.

[01:39:33] Nathan: Or the paid subscribers. Yeah. Then I think that works really well. ‘Cause my, my whole issue is just when people put growth and monetization at odds with each other.

[01:39:42] Chenell: Mm-hmm.

[01:39:43] Nathan: Which most paid newsletters do, but you don’t have to.

[01:39:45] Chenell: Yeah.

[01:39:46] Nathan: I should do a whole thing on how you can do paid newsletters well, and how they’re actually great, because this is on the surface, they suck.

[01:39:52] Chenell: Yeah. The other thing I also… This is kind of aside, but when people have just, like, the main free newsletter- Mm-hmm … and the whole thing you can’t see unless you’re subscribed.

[01:40:02] Mm-hmm. I… That drives me insane.

[01:40:04] Nathan: Okay.

[01:40:05] Chenell: Like, when you go to a post and you try to scroll, and it’s like, “Log in or subscribe” or whatever.

[01:40:10] Nathan: Mm-hmm. And

[01:40:10] Chenell: it’s locked. I hate that. Yep. I immediately leave, and I’m like, “I’m not coming back.”

[01:40:14] Nathan: Just on principle.

[01:40:14] Chenell: Yeah. And so I think people cap their growth that way, too.

[01:40:18] Mm-hmm. And they think it’s driving more subscribers. It probably is to an extent, but I think you’re also missing out on a lot of traffic that you would’ve- Mm-hmm … otherwise converted.

[01:40:25] Nathan: And so it’s like deliver, you gotta deliver enough value. ‘Cause if you’re locking it after three sentences-

[01:40:31] Chenell: Right …

[01:40:31] Nathan: then, like, there’s n- I don’t know that it’s-

[01:40:34] Chenell: Right

[01:40:34] Nathan: valuable yet. Um, I have subscribed to newsletters ’cause I’m like, “I really w- want this thing,” and you know what? Sure, it’s an email address.

[01:40:42] Chenell: Yeah. Sometimes it can work- Yeah … but most of the time I’m like, “Oh, no.”

[01:40:44] Nathan: Yeah, playing a long-term game.

[01:40:45] Chenell: Yeah.

[01:40:46] Nathan: That’d be different.

[01:40:47] Chenell: Exactly.

[01:40:48] Nathan: Okay. Price point on paid newsletters.

[01:40:50] We probably see a whole range. I feel like that’s the other thing that I hate is when someone’s like, “Five bucks a month.”

[01:40:55] Chenell: Yeah.

[01:40:55] Nathan: And I’m like- Nope … either make something valuable- … or make it free.

[01:40:59] Chenell: Yep, exactly. Uh, it’s gonna depend, and sometimes I think paid newsletters, if you’re not, like, helping someone invest in the stock market, like- Right

[01:41:06] it’s pretty hard to charge a high premium. But if you can do, like, a $200 a year situation- Mm-hmm … and then get the volume-

[01:41:12] Nathan: Yeah … that’ll

[01:41:12] Chenell: work.

[01:41:13] Nathan: Then that’s good.

[01:41:13] Chenell: But there are finance newsletters charging $1,000 a year or more

[01:41:18] Nathan: for that. I think it’s super interesting to ask a question of, like, what would have to be true to charge $1,000 a year for this content?

[01:41:23] Chenell: Right.

[01:41:23] Nathan: And like, oh, well, it’d have to be great. It’d have to be something that’s so good they’re not getting other places. And you’re like, okay, that’s probably where the bar should be anyway. Right.

[01:41:30] Chenell: Exactly.

[01:41:31] Nathan: And then if you need that as a forcing function to say, like, “Oh, every newsletter that I send out, people should…

[01:41:37] My audience, not everyone, my audience receiving it should feel like this was worth $50.”

[01:41:44] Chenell: Yeah.

[01:41:44] Nathan: Just this one thing. And if you hit that bar, then you’re gonna go really, really far.

[01:41:49] Chenell: Yeah. The one thing I will say with paid newsletters is you wanna add other features to it so it’s not like I’m getting four emails, it’s $200 a month- Mm-hmm

[01:41:58] or $200 a year, so it’s X dollars per email. If you can add other things into it to make people not be able to back into the numbers as easily- Right … that’s gonna really help with retention and-

[01:42:07] Nathan: What are some other things that you would add?

[01:42:09] Chenell: Um, well, if we’re talking about Substack, you could do, like, a private chat- Yeah

[01:42:12] or AMAs or have… I think Justin Walsh was doing this for a while with, uh, his paid newsletter on Substack where he was having, you know, monthly calls where he would bring in outsiders to teach stuff. It almost became like a membership. Yeah, I

[01:42:24] Nathan: got one of those. Right. Mm-hmm.

[01:42:25] Chenell: Um, so I think you can add stuff like that into it.

[01:42:27] There could be templates. Um, Tom Orbach, who wrote the Marketing Ideas, he, he wrote a full book that was, like, his best marketing ideas in this- Mm. Yep … really well-designed PDF.

[01:42:36] Nathan: Yeah, I’ve also seen people take their past issues and bundle them up with good design and say, “Oh, you’re getting this.” And it, by switching formats, it feels like the value increases.

[01:42:48] Chenell: Yeah.

[01:42:48] Nathan: Um-

[01:42:48] Chenell: You could go the Lenny route and give away, like, software deals.

[01:42:51] Nathan: Yep.

[01:42:51] Chenell: That’s a crazy business right now.

[01:42:54] Nathan: That is. It’s just because there’s so much money flowing into AI right now. But yeah.

[01:42:58] Chenell: It’s working.

[01:42:58] Nathan: That’s wild. I think the last thing, um, that still works quite well, I feel like people don’t talk about it as much, is these, um, guides, checklists, like, any of these things at the 10, $20 price point.

[01:43:12] I see people like Maria Went doing really, really well selling inexpensive items, you know? And this is where you’re hanging out in the- Well, let’s call it 15 to $50 range. Yeah. Um, and the price point is low enough that you can often get a big audience. Uh, a lot of people can make their, their ads profitable on this.

[01:43:31] They can get, get a good payback.

[01:43:33] Chenell: Yeah.

[01:43:33] Nathan: Uh, they’re getting that. Especially if there’s a, if a $15 product with, like, a, an order bump upsell at the end. Like, it does well.

[01:43:40] Chenell: Totally.

[01:43:41] Nathan: And so even as everyone’s focused on this higher end and you hear, you know, stories about Dustin or whoever else, like, there’s still a lot in the inexpensive range.

[01:43:49] Chenell: Yeah. And I think just right now we’re seeing a, a move back towards services. But- Mm-hmm … the pendulum will swing back. Yeah. And so I think if you’re well-positioned in that space, it’ll work out.

[01:43:57] Nathan: Yeah. I love that. Chanelle- Yeah … this has been amazing. So we… And we’ve covered so much. I’m sure people have taken a lot of notes.

[01:44:04] I’m sure they, uh, enjoyed my public embarrassment, and then went like, “I won’t give him a hard time because, you know,” “I think mine is, you know, just as bad.” I, I think the, the tangible, like, diving in and saying like, “Oh, the exact mistakes that are made,” not theoretical, but, like, in an actual newsletter. This is the kind of thing you obsess over.

[01:44:23] Chenell: Yes.

[01:44:23] Nathan: You talk about this all the time.

[01:44:25] Chenell: Yes.

[01:44:25] Nathan: If people wanna come into your world and say like, “All right.” Yeah. “Like, I got a taste. Now I wanna go deep,” where should they go?

[01:44:31] Chenell: Yeah. So we did talk a lot about this, the five pieces of this. And it can be hard to figure out which one’s working and what- Mm-hmm … you should focus on first.

[01:44:38] So I actually created, um, an assessment that gives you a score- Oh, nice … at the end. And so it’ll tell you which one to focus on and kinda, like, the next step to take.

[01:44:46] Nathan: Mm-hmm.

[01:44:47] Chenell: And so you can go to growthinreverse.com/scorecard and grab that for free. Nice. Yeah.

[01:44:51] Nathan: Sounds good.

[01:44:52] Chenell: Great.

[01:44:53] Nathan: Well, thank you so much for coming on.

[01:44:54] Chenell: Thanks for having me.

[01:44:55] Nathan: Chenell just walked you through the five levers behind a growing newsletter. And if you wanna see them running at scale, check out episode 126 with Sean Devlin. Sean grew Nice News to 800,000 subscribers before Encyclopedia Britannica acquired it. And now he runs All Healthy at 1.3 million subscribers and a 52% open rate.

[01:45:15] There’s a lot of good stuff in the episode, and I think you’re gonna love it. So if you enjoyed this video, make sure to like it and hit subscribe on YouTube or wherever you’re listening. And thank you so much for tuning in.

[00:00:00] Dan: The spicy part of the take is, like, the newsletter is dead. It’s gonna be a rude awakening in two years when you’re like, “My open rate is zero,” or it’s 100%, but, like, no one is interacting with it.

[00:00:09] Nathan: Dan runs a company called Every that writes about AI, builds AI software, and gets access to the models even before they come out.

[00:00:17] He’s interviewed Sam Altman, and he’s just about as close to the cutting edge as anyone I know.

[00:00:21] Dan: It’s getting really crazy right now because two things have happened. One is computer use is incredibly good.

[00:00:27] Nathan: And they’re doing it in the editing tool.

[00:00:30] Dan: They’re using Premiere.

[00:00:31] Nathan: Yeah.

[00:00:31] Dan: And they’re fast. And the other crazy thing is-

[00:00:35] Nathan: The newsletter is dead.

[00:00:36] As much as I hate to admit it, I think Dan might be right.

[00:00:39] Dan: OpenAI or Claude is gonna, like, come out with an inbox. Right. But it’s gonna be different. It’s gonna not look like an email inbox in the same way. It’s gonna be- Oh, wow.

[00:00:50] Nathan: There’s one number Dan’s entire team is chasing right now.

[00:00:53] Dan: Our quarterly goal right now is how many emails we get.

[00:00:56] Nathan: And he told me why they might stop chasing it in the next few months.

[00:00:59] Dan: If you’re ranking really well for AEO right now, there’s a really good chance that that’s going to be a big signal that goes into whether the agent, like, lets you through. Oh, interesting.

[00:01:08] Nathan: If email is an important part of your business, you need to listen to this episode.

[00:01:12] Dan: There’s this crazy important technology change happening, and I’m just, like, sitting right in the middle of it

[00:01:22] Nathan: Dan, welcome to the show.

[00:01:23] Dan: Thanks for having me. Great to be here.

[00:01:24] Nathan: So I wanna dive in on Every as a product and a business and all of that, but before we do that, you’re on the cutting edge of what’s happening in AI. Like, whenever a model drops, you’re like, “Cool, yeah, we’ve been able to play with it for the last, like, three, four weeks, and here’s our take on it.”

[00:01:37] You know, and every time I ask you a question, I can see you processing of, like, what’s under NDA- … what’s not, like, what can I say? And then you’re like, “Oh, here we go,” you know? Um, where I wanna start is what’s a workflow that any professional creator should, like, go set up today?

[00:01:52] Dan: I think the w- the place that professional creative work is going is you’re gonna do most of your work inside of an agent harness- Yeah

[00:02:04] like ChatGPT for work or Claude, the Claude desktop app. And specifically you’re gonna have in, in one of those apps, you have your agent on, on one side, and then the, the main portion of the screen is taken up by in an in-app browser, and you’re on whatever site you would be in, whether it’s Google Docs or Notion or, like, Kit or any of the- Yeah

[00:02:25] any of those tools. Um, and you’re just kind of going back and forth where you and the agent are doing deep collaboration, and the agent is also, like, going off and doing a bunch of stuff in the background that you’re not looking at. So I think that workflow is incredibly important to get familiar with, and it’s also incredibly powerful.

[00:02:43] And once you start doing that, it opens up lots of stuff. So a thing that I do all the time is I just talk t- I talk while I write. Mm-hmm. And I’m, like, talking… I’m, like, writing stuff, and I’m talking to my agent and I’m like, “Can you go look this up?” Or like, “Can you, uh, change this paragraph, like, that’s further up in the piece?”

[00:02:59] And it’s like, “Cool, I’m gonna go do that,” and I’m, I’m gonna keep writing. I often, when I’m writing, I am not even, uh, like, looking at a screen. I just have my, my AirPods in and I’m like- Okay … I’m looking at a notebook on a couch, and I’m just, like, talking out a piece of- Mm-hmm … a paragraph and maybe I’m writing in the notebook and I’m like, “Okay, read it back to me.

[00:03:21] What, what, what’s there?” And then it reads it back, and then I write it down, and then I… We play with it together.

[00:03:26] Nathan: And so when you’re doing that, you have- You’re just in voice mode-

[00:03:31] Dan: Mm-hmm …

[00:03:31] Nathan: for the tool? Yeah. So you’re, you’re not even using monologue or something like that? I’m

[00:03:34] Dan: just in voice mode, like, in, uh, in ChatGPT, yeah.

[00:03:37] Nathan: Mm. Okay, and so then a prompt you would say, like, “Hey, a couple paragraphs earlier I said this.” Like, add something to it.

[00:03:44] Dan: Yeah.

[00:03:44] Nathan: And then it’s gonna work on that- Yeah … while you’re-

[00:03:46] Dan: Yes …

[00:03:46] Nathan: actually using the hands on the keyboard for the draft.

[00:03:48] Dan: Yes. Or, like, if, if I’m doing it sort of not looking at a screen, I’m like, “Cool, I wanna work on the ending paragraph th- of the intro.

[00:03:54] Can you read me the intro again, and then, uh, tell me what the end- ending paragraph is right now?” And then it’ll be like, “Here’s the ending paragraph.” And then I’ll be like, “Can you do another… Like, what, what would it be like if we tweaked this sentence of that paragraph, and can you just do a take on that so I can, like, get it in my ear?”

[00:04:08] And then it’ll do it, and then I’ll, I’ll, like, write it, I’ll write down… It, basically it tells me something that I think is not, not right- Mm-hmm … but, like, it’s close enough that it kinda, like, gets my brain going, and then I’ll write it down. I’ll be like, “Here’s what the paragraph is,” and then it’ll pu- push it in- Oh, interesting

[00:04:21] and then we go to the next one. It’s getting really crazy right now because two things have happened that I think are very important. One is computer use is incredibly good. Um, so the models right now, for example, are editing video And they’re very good at editing video

[00:04:39] Nathan: And they’re doing it in the editing tools.

[00:04:42] Yeah Like, it’s not like, oh- Yeah … Claude now has a function separate- No, no … for editing videos.

[00:04:46] Dan: It’s, they’re using Premiere.

[00:04:47] Nathan: Yeah.

[00:04:48] Dan: Uh, and they’re fast, and they’re pretty good. Um, so that’s one, like, crazy, crazy thing, and the other crazy thing is Gemini 4, which came out, I guess, this week. I don’t know. What is time?

[00:05:01] But like- Yeah … it ca- came out the week that we’re recording this, uh, is a very good writer, very much better than any other model weirdly.

[00:05:09] Nathan: Oh, interesting.

[00:05:10] Dan: And- Yeah, I would

[00:05:10] Nathan: not expect that based on-

[00:05:11] Dan: Yeah …

[00:05:12] Nathan: previous trends.

[00:05:12] Dan: It’s so good. And so, like, so I just today published this, uh, 8,000 word, like, long form feature story about Codex called How Codex Happened.

[00:05:23] Nathan: Mm-hmm.

[00:05:24] Dan: To me, I’m like, this is one of the best things I- I’ve ever written. And when you’re writing something that long, you’ve written books so you know this. Oh, yeah. When you’re writing something that long you’re often… You’re like, “Okay, there’s this section in the middle,” and now that I see the full structure, it’s, like, completely out of order, and I have to go, like, reorder all of it.

[00:05:42] Nathan: Mm-hmm.

[00:05:43] Dan: And it’s mostly written, but you have to, like, really think about, okay, h- what’s the most interesting thing? Uh, like, what should be at the top now, and, like, how do I do this? And, uh, you know, you almost wanna have, like, scissors and you’re, like, cutting things out and, like- Right … rearranging them. I’ve

[00:05:57] Nathan: always wanted it of, like, in a 3D space.

[00:05:59] Yeah. I wanna see… And I’ve done that with my, like, my actual book- Yeah … where I’ve said like, “Okay, how do these sections fit together?” And I’ve tried

[00:06:05] Dan: to rearrange them. Sometimes you need that. Sometimes you need that. Right. But for me, so, like, for this piece, there was a big section, like 1,000-word section in the middle of the piece, and it’s, like, two days before publication, and I’m like, I have another job too.

[00:06:18] Like, I’m not… This is not all I do.

[00:06:20] Nathan: Yeah.

[00:06:20] Dan: And I realize it’s completely out of order, so I had Gemini. I was like, “Look, this section, this section of the piece is, it’s out of order. Here’s what I think the order needs to be, but I want you to, like, read it and think about it.” Mm-hmm. And what I actually did is I had my dot, the always on persistent ChatGPT agent.

[00:06:36] Right. I was like, “Hey, this section that we’re working on, totally out of order. I want you to go to Gemini, give it the piece, give it my prompt about the out of order, and then I want you to ask Gemini to critique-

[00:06:50] Nathan: Mm-hmm …

[00:06:51] Dan: come up with a new order- And then go into the document and apply it as a track change.

[00:06:57] Nathan: Okay.

[00:06:58] Dan: And it just, like, went in and, like, para- like delete paragraph, move up, delete paragraph, move up. Like, and then I came back, like, an hour later, and it was reordered. Was not perfect, but it was, like, very close.

[00:07:09] Nathan: Right.

[00:07:09] Dan: And then I’m just like, “Accept or suggest it up.” And then I’m, like, kind of stitching it together.

[00:07:13] Nathan: Um- And so again, you’re, you’re having it do this in Google Docs?

[00:07:16] Dan: Yeah.

[00:07:16] Nathan: And so then you get the full track changes as if you had just given that prompt to a human editor.

[00:07:20] Dan: Exactly.

[00:07:21] Nathan: Okay.

[00:07:22] Dan: And I, by the way, have human editors. Right. I have two, um, who worked on this piece with me who are ex- extremely talented.

[00:07:27] Mm-hmm. But this is, this is at a stage before they would look at it.

[00:07:31] Nathan: Right. Yeah, and you talked about the process of inside the Everyagent of how you tried to, I guess, productize, agentize your editor-in-chief, right? And-

[00:07:42] Dan: Yes …

[00:07:42] Nathan: and, like, learn from the e- the edits that she makes, and then get, you know, ev- like elevate everyone’s writing before she even looks at it.

[00:07:49] Dan: Yes, we also do that. Um, so what we do, so we have the Everyagent. It’s a AI coworker that makes it super easy to AI pill your entire organization ’cause you, when you use it in your Slack, you, you, you prompt in public, and that, that- So everyone else sees- … just teaches people- Yeah … ’cause you’re showing them instead of telling them.

[00:08:06] Uh, instead of get- trying to explain it all the time, you’re just like, “@Every do this thing,” and it works the way that we work. So it just makes it easy to show everyone and get them to adopt it. And one of the workflows that has started to work really well is thinking about how do we compound the knowledge of our experts in the organization so, uh, and push that into the agent so that other people in the organization can use that knowledge and expertise without taking up more of that person’s time.

[00:08:34] Nathan: Right.

[00:08:35] Dan: So with, with Kate, who’s our editor-in-chief, she’s a fantastic copy editor- What I, what we did is we took, um, she’s been with us for, like, four years or something like that, so we have a lot of her edits, and we took, like, 30 or 40,000 of her copy edits and turned it into a skill that whenever, like, before she sees a piece, you just @ The Every Agent and you’re like, “Do a Kate pass on this.”

[00:08:58] And it does, like, a lot of the stuff that she would do so that when sh- by the time she sees it, it’s closer to her taste and she doesn’t have to spend as much time on each individual piece. Yeah. And it gets better over time, so it learns, uh, each time that it does stuff and she accepts or rejects things or adds things, sh- it learns, like, here’s, here’s the kind of stuff I miss, so that she’s doing less and less, but she has more and more impact around, around the org.

[00:09:22] And I think that’s, it’s just like a r- it’s a kind of peek into how you will work well as an expert in- Right … the future, is being the one who is in charge of making sure that system works, um, instead of just doing every single thing by hand. You’re

[00:09:36] Nathan: getting the compounding value.

[00:09:37] Dan: Yeah.

[00:09:38] Nathan: Okay. So talk about how you actually implement that, ’cause I think a lot of people say

[00:09:42] Well, actually, maybe let’s back up to the skill.

[00:09:43] Dan: Yeah.

[00:09:44] Nathan: So a lot of people would say, “Oh man, I have to write an entire skill that does this.” But no human wrote that skill, right?

[00:09:51] Dan: Yes. No human wrote that skill. This is where I would say for now-

[00:09:57] Nathan: Mm-hmm …

[00:09:57] Dan: it’s hard.

[00:09:58] Nathan: Okay.

[00:09:59] Dan: It’s easy to do a first pass. Yeah. It’s hard to actually make it good.

[00:10:03] It will not be hard in six months to a year. So I think, like, I would, I would look at this as a preview of a workflow that will be super, super common for everybody, um, in maybe a year. But for now, it’s something that if you’re, like, super AI-pilled or you’re technical, like, you should try this. Mm-hmm. Um, and the way to do it would be go grab a bunch of, um, if you have a bunch of data that of, like, of you doing a particular kind of task or making- Yeah

[00:10:29] a particular kind of decision, aggregate it, tell Claude or Codex or ChatGPT, like, “Make me a skill,” and then put it into your Codex or ChatGPT or if you have a Slack agent like the Everyagent- Mm … you put it in there. Try to use it and set up your system so that every time you use it, it scans to be like, “What did I miss?”

[00:10:47] And puts it- Mm … back into the skill.

[00:10:49] Nathan: Okay, what’s the… Like, I feel like that feedback loop, I’m obsessed with flywheels, right? Yeah. And so that feedback loop- Mm … is so important. How do you best set that up?

[00:10:56] Dan: All of the solutions right now are a little bit bespoke. Okay. So, so-

[00:11:00] Nathan: Depending on the skill, like, that you’re trying

[00:11:02] Dan: to set up.

[00:11:02] Uh, depending on the skill, but the, the core thing that you’re, the core thing that you’re doing is when you get all this data, uh, you create an eval. And an eval is just a test that’s like, um, it gives a model a bunch of questions or tasks that look like the kinds of stuff it’s gonna have to do in order to do work well in your particular way.

[00:11:21] It’s like the Nathan eval. What the eval allows you to do is it allows you to measure the model’s performance at doing your work. So every time you run the model, you can be like-

[00:11:31] Nathan: Mm-hmm …

[00:11:31] Dan: how, how good did it do at this test? And you can always be adding to the test or changing the test to make sure it, it better reflects, like, what your, what your work is like.

[00:11:39] But the core thing is make an eval. Once you have an eval, uh, have your model make a… have, have Claude make a skill for you that maximizes the score on the eval. So it’s like in 50, in 50% of the cases that, you know, Kate might make a copy edit, we can, we can tell that this model does 50, 50% of… gets 50% right.

[00:12:00] Nathan: Yeah.

[00:12:00] Dan: And then what you do is, uh, over time, as you get more and more data and it’s used in more and more places, uh, you start to… you try to modify the skill to incorporate more of that data or more of those learnings, and then you just measure it again on the eval, and you just try to maximize the score.

[00:12:17] Nathan: Okay.

[00:12:18] Dan: And that’s the, like, high level of how it works. Yep.

[00:12:20] Nathan: Hey, so you may know me as the host of this podcast, but I’m also the founder and CEO of Kit, an email marketing platform for creators. I built Kit because I needed a better way to grow my audience and sell books and courses through email. Kit helps you build an audience that you own and will create automations that keep working for you so that you can focus

[00:12:39] Dan: on creating.

[00:12:40] As a listener of this show, you can get an exclusive 10% off Kit Pro if you go to kit.com/nathan.

[00:12:45] Nathan: I think a lot of creators find themselves stuck jumping from platform to fl- platform- Mm … because they watch a YouTube video or hear a podcast and it’s like, “Muse is out now, it can do this,” and then they’re, like, halfway through the setup, and then it’s like, “Dots can do that.”

[00:13:00] Yeah. And you’re like, “Oh, I should jump, jump from that.” Well, a decision that I made recently was to just … I, I mean, I have subscriptions to everything, but to just pick one platform and dive all in. I chose GroqBot. It’s working really well for me. I don’t know that it’s better than anything else.

[00:13:16] Dan: Yeah.

[00:13:17] Nathan: You know, in two weeks or six months, the answer might be different.

[00:13:21] My take is that m- people would be better off to just pick one and go deep than, like, constantly be 5% deep in a whole bunch of them. Um, I’m curious for two things. One, what’s your take? Like, what would you recommend, uh, someone do? And then two, how would you recommend they think about which platform to choose?

[00:13:38] Dan: It’s gonna be very personal. Yeah. It’s gonna d- depend on who you are and what your thing is. Like, for me, like, my job is to test all this stuff. Right. Yeah, you

[00:13:45] Nathan: need to

[00:13:45] Dan: be in all of them. So I, I wanna be testing all the different, all the different things. And part of the reason it became my job is ’cause I just li- I just like doing that.

[00:13:52] Yeah. You know? Um, I would do it even if it wasn’t my job, which is, I think, part of why- Like, how it, it ended up being your job … I’m good at it, you know? Yeah. As well. Yeah. It is meaningful to me, for example, that I just know that Gemini is really good at this right now.

[00:14:05] Nathan: Mm-hmm.

[00:14:05] Dan: And I … It’s, like, so fun to just jump into Gemini for writing tasks- Mm

[00:14:11] even though I’m using Claude for, like, long w- w- like, this new machine l- m- machine interpretability, uh, paper came out today, and I’m … Like, right now it’s working on, like, building something based on that paper. Okay. And then my dot is, like, doing all my, my, like, nor- normal day-to-day work, and so I’ve got all these different things on different platforms.

[00:14:29] The company’s called Every. Every. Like, I like, I like doing lots of things, you know? Yep. And I … But I think some people are just like, “I want, I wanna focus. I wanna understand my environment and my tool.” Mm-hmm. “And I wanna, like, almost become one with the tool.”

[00:14:43] Nathan: Right. ”

[00:14:43] Dan: And if I’m a little bit behind the frontier, like, that’s fine,” because, you know, it’ll, it

[00:14:48] Like, all of these things will be at parity, like, the major platforms will be at parity. It might take six months, it might take a year. Right. But, like, it’s gonna more or less be fine. It’s worth thinking about why am I jumping? Am I jumping because I genuinely love this and I’m just like- Mm-hmm … this is the coolest thing, or am I just, have I- I’m having so much FOMO and I’m just spinning my wheels to not miss out?

[00:15:15] Nathan: Mm-hmm.

[00:15:16] Dan: Because trying not to miss out is, like, not the thing. Yeah. It’s like, what do you wanna do with this? Mm-hmm. Is this enjoyable for you? Is it helping you do the work you wanna do? Um, if s- if so, jump. If not, don’t.

[00:15:29] Nathan: What I found is, yeah, is going deep and then just setting up as many connectors as possible.

[00:15:33] And I can still share a workflow that, you know, has worked well for me. I meet a ton of people in person, and so now we’re in this, you know, you’re, you’re talking to someone at an event and it’s usually like, “Oh, let’s share contact info.” And so, you know, touch the phones together, they share, and it just goes off into this, um, you know, void, never to be found again.

[00:15:53] Yeah. Right? And so you have to, like, find them and send them a text right away so that they stay at the top somewhere. And you can implement this, I think, in most tools, I did it in Grokbot, where it monitors anyone added to my contact book-

[00:16:05] Dan: That’s cool …

[00:16:06] Nathan: logs who is, where I was. So it checks my calendar to be like, “Oh, you were at the Authors Equity Dinner-

[00:16:11] Dan: Ugh, I

[00:16:12] Nathan: need that

[00:16:13] when these were added.”

[00:16:13] Dan: That’s a great idea.

[00:16:14] Nathan: And then it l- adds them to a follow-up of who, and it’ll enrich the contacts a- as well.

[00:16:19] Dan: Yeah.

[00:16:19] Nathan: And so the, “Oh, we, we know who this is, we know where you met them.”

[00:16:22] Dan: I

[00:16:22] Nathan: mean- And then I just forget to, like, I don’t forget to follow up …

[00:16:24] Dan: the, like, this is the golden age for the personal CRM bros, you know?

[00:16:28] Yes. Like, this is what we’ve all been waiting for.

[00:16:33] Um, I love that. I, I really actually need to do that ’cause I have that exact thing where I’m like, “Oh, I meet all these people and they’re really cool,” and then I just never talk to them again.

[00:16:40] Nathan: Yeah, and so you could add workflows in that- Yeah … where you could say, “You know what? Everyone I meet in person- Yeah

[00:16:44] I wanna follow on X.”

[00:16:45] Dan: Yeah.

[00:16:46] Nathan: And it would just do that.

[00:16:47] Dan: Yeah.

[00:16:48] Nathan: And so, but now I feel so much more free at an event, ’cause I, all I need to do is touch phones together. Yeah, yeah,

[00:16:54] Dan: yeah, and it’s,

[00:16:54] Nathan: it’s handled. And then, then everything else- Yeah … is handled. I love that. And it’ll be like, “Hey, you met these five people.

[00:16:58] Did you wanna- Yeah … you’re on the flight home. Did you wanna send-”

[00:17:00] Dan: Grokbot’s one of those things, I, I’ve never used it.

[00:17:02] Nathan: Really?

[00:17:02] Dan: I, well, I used it, they sent it to us, so some people on my team use it. They sent it to us- Yeah … before it came out, and I, like, went into it for, like, two seconds and I was like, “This looks exactly like OpenClaw.”

[00:17:12] And- Yes, yes … then I just, like, didn’t use it. Mm-hmm. Um, and then Dots came out, and I’m already… I’m so in the ChatGPT ecosystem- Right … so I do have some of this, like, ecosystem stuff- Yeah … that I was like, “Okay, this is, this

[00:17:23] Nathan: one, this will probably work.” I think you could set up that same workflow with Dots as well.

[00:17:25] Dan: Yeah.

[00:17:25] Nathan: So long as… Can Dots read iMessage?

[00:17:27] Dan: Yeah.

[00:17:28] Nathan: Okay.

[00:17:29] Dan: Uh, if it’s on, if it’s on your

[00:17:31] Nathan: computer. If it, if your computer is open.

[00:17:32] Dan: Yeah, yeah, yeah,

[00:17:32] Nathan: yeah, yeah. It’s a whole thing. Yeah, yeah. I asked a question- Yeah … and it was like, “Uh, your, both your laptop and your iMac are off right now, and so I can’t read that.” And I was like, “Oh.”

[00:17:41] Dan: Sucks. Sucks when that happens.

[00:17:43] Nathan: Yeah, exactly, and I’m like, “Uh…”

[00:17:45] Dan: I get that with Dot, but it’s like my Mac Mini is never off. Right. Like, I’ve told it to never go off, so I’m like, “No, no, it’s, it’s on,” and it’s… and then it comes back and it’s like, “You’re right, it’s on.” And I’m like, “I know.”

[00:17:55] Nathan: I need to have my Mac Studio at home, not

[00:17:57] Dan: at work.

[00:17:57] But it’s so funny that that’s the thing that is, they’re being dumb about right now because, like, a year ago it was so different.

[00:18:05] Nathan: Mm-hmm.

[00:18:06] Dan: It was so different. A year ago, I couldn’t, you couldn’t tell the AI, “Hey, can you help me write this as a tweet?” Because if you asked it to write something, like help you write a tweet, it would put like 14 hashtags into every tweet.

[00:18:18] Nathan: Right.

[00:18:19] Dan: And now, like, obviously that doesn’t happen anymore, and it’s just so… It’s crazy how much it’s changed.

[00:18:24] Nathan: Well, so I want to talk about, like, the future of AI, ’cause I think so many people are absolutely freaked out.

[00:18:30] Dan: Yeah.

[00:18:30] Nathan: And you have a, a different take where you’re like, “The future is great.” Like, I, I talk to you and you are high on the future of where this is going.

[00:18:40] Like, what do you say to someone who is timid about it and is saying like, “I don’t, I don’t know if the future’s gonna be better than the past”? Um, I mean, first of all, I do think that there’s just a little bit of a personality thing-

[00:18:52] Dan: Yeah … about, like, new things and change and whatever, and d- different people have different feelings about, about that.

[00:18:57] And, um, I think, you know, if I was in, you know, around the, the Enlightenment, I would’ve been be like, “This printing press thing is so

[00:19:08] Nathan: sick,”

[00:19:08] Dan: you know? Yeah. And people have been like, “It’s ruining, like, uh, oral communication- Right … and social standards and, like, whatever, you know? Um, and, uh, b- I think you have to kind of have both in a society, so I, I kind of, I kind of value both.

[00:19:21] But my, um-

[00:19:22] Nathan: But you know which r- which role you play.

[00:19:23] Dan: I know which role I play, yeah. Um, which, which is to say I actually… I think that there are some people who love new things and hate old things. I actually love old things. Mm-hmm. Like, I love books. My house is full of books. Yeah. I only read paper books.

[00:19:34] Nathan: Mm.

[00:19:34] Dan: I tend to be the kind of person that’s like, “I’m gonna go swim in this new world and then tell you how and why it can be just as great,” and, and- Mm … and it can connect to the old world that you’re- Mm … thinking is totally gone, ’cause it’s, it’s g- there’s gonna be things that are different, but there’s gonna be a lot of things that are the same.

[00:19:50] And the, one of the core things that I think is the same or will, will end up being the same is when people encounter a new technology, they often have a little bit of a disgust reaction or like a, it feels shallow or flat or somehow inhuman or impersonal. And m- m- what I feel is when you look around, like we’re in this podcast studio, right?

[00:20:16] All of- We’re surrounded by technology. Right. That if, uh, that for us maybe, you know, podcasting in this way in person it feels very, it feels personal and it feels like a human thing, but if you went back 100 years it would be like, “What the fuck is going on here?” “This is crazy.” And so, uh, is to s- is to, one, recognize that that feeling of it- it’s- it’s- it has some soul, I have some connection to it, is something that you build up over time, um, by being in contact with the world, which includes all the technology in it.

[00:20:49] So just because you don’t have that with the machine right now doesn’t mean you won’t build it.

[00:20:54] Nathan: Right.

[00:20:55] Dan: And, and in fact, I think we will and do. And generally, I think there’s a w- w- I’ve observed a very predictable pattern of how people encounter and then adapt to new technology, which is first you encounter it and you’re like, especially with AI, you’re like, “Holy shit, this is going to like completely erase me.”

[00:21:17] It, it’s like, uh, I’ve been calling it an agency rupture. It just … It, it feels like this thing that I do well, it’s no longer valuable.

[00:21:24] Nathan: When, like iterations of that when you first see it write really well and, or like you send a prompt and it comes back or it completes a task. Another one is when you watch it use your computer better than you do.

[00:21:34] Dan: Yeah.

[00:21:35] Nathan: Like the video editing is one of those- Yeah … where you’re like, “I thought I was pretty good at keyboard shortcuts- Yeah. … for Premiere and you know keyframes- I am not good at that … and all that. Yeah. And you’re like, “Oh.” It’s, it’s one thing where you’re like, “Okay, it went off and it did magic and it came back.”

[00:21:46] Yeah. But when I can sit there and watch it and I’m like Huh,

[00:21:50] Dan: okay.

[00:21:50] Nathan: Yes. You know, it’s another one of those moments where you’re like, “Okay, my, my worldview, w- you know, what I- my view of what’s possible needs to change.”

[00:21:57] Dan: Exactly. It’s a, and s- and it’s an, it’s an agency rupture, and it feels like shit. I think if you’re someone who’s a tech person and like to write, you had this around GPT-3.

[00:22:08] You, you were s- you saw GPT-3 writing- Mm-hmm … and you’re like, “Fuck.” Yeah. And then it happened for coders over the last couple years.

[00:22:16] Nathan: Right.

[00:22:16] Dan: And then now it’s happening for mathematicians. Mm. And it’s just like a, it’s a very regular thing. Mm-hmm. But I, I think that that’s the first stage is encounter, first encounter and rupture.

[00:22:26] The second stage to me is, “Oh, yeah, it can do all that. It can use my computer better than me, but I have to do a lot of, um, babysitting of it and setting it up to, to, to do the task in the right way at the right time.”

[00:22:39] Nathan: Mm-hmm.

[00:22:40] Dan: But you’re like, “Ah, but that’s still, I’m just kind of babysitting a model, and the model’s doing the work.”

[00:22:45] And then the, the last phase is you’re like, “Actually, that itself is a full task full of like richness and complexity that I didn’t realize was there because I’d never had to do it before. But now that I’m really thinking about this, there’s so much that can be done to make, you know, maybe a model can go and edit a video in 20 minutes, but what kind of video?”

[00:23:07] Right. “And what are all the details of that? And, and, and, and not just any given video, but all of the videos that you produce.” And so you’re, you started to open up this whole new universe that you didn’t qu- quite realize was there. The way that people tend to think about new technology is sort of the way that people thought about what was beyond the horizon in the Middle Ages.

[00:23:27] It’s like, if you went beyond the horizon, it’s like it falls off. There’s dragons. Right, who

[00:23:31] Nathan: knows?

[00:23:31] Dan: Yeah. Yeah. But like you take a ship out there, and you’re like, actually there’s just more, more land and more stuff, you know? And it’s, there’s good stuff. There’s bad stuff. There’s … I- if you spend a lot of time out there, y- you, you make a, you make a home there.

[00:23:43] It feels, it can feel amazing. You might be homesick too, but, um, I think it’s, it’s much more like that than, oh, it’s, uh, we lose everything that we love and, uh, a- and we all die. Right. Like, it’s, it’s not usually like that.

[00:23:59] Nathan: How do you think about ambition in the age of AI, especially as it relates to creators?

[00:24:04] Dan: I’ve been talking to a, a couple of different- like sort of bigger name people about this recently because, and we see this too a little bit, but especially if you’re someone who, you know, you- you’re a big name and people come to you for answers to questions, for example, you’re probably seeing your search engine traffic drop off-

[00:24:21] Nathan: Oh, yeah

[00:24:21] Dan: you know? Um, or I know, like, I know Tim Ferriss was tweeting, you know, uh- Book sales went down … my book sales are down, like that kind of stuff.

[00:24:27] Nathan: I do know other authors who are having the opposite experience.

[00:24:32] Dan: Yeah. I, I, I, I think that, I don’t think it’s one or the other.

[00:24:37] Nathan: Yeah.

[00:24:37] Dan: And there’s a lot of reasons why Tim in particular, because The 4-Hour Work, Work Week is like, it’s so, it’s such a book that should be written now-

[00:24:46] Nathan: Right

[00:24:47] Dan: but rewritten, ’cause, like, all the stuff would be different, but he could d- he could do like- But

[00:24:50] Nathan: the, the premise-

[00:24:51] Dan: He could do The 4-Minute Work Week. Right. You know? The premise is so good.

[00:24:55] Nathan: Of extreme leverage.

[00:24:56] Dan: You could actually do it now. How do I use extreme leverage? Yeah. You know? Oh, yeah. You can actually do it, so I think, I think he has a huge opportunity if he wants it.

[00:25:02] Mm-hmm. But if you go read The 4-Hour Work Week right now, there’s so much translating that you have to do- Mm-hmm … from, you know, I read that when I was in middle school or high school. Yeah. There’s so much translating you have to do from that era to this that I can understand why it might not be as popular right now.

[00:25:17] Right. But I, there’s this other thing that’s happening, which is if people go to you for answers to questions, Google has changed things, so now there’s, like, the AI answers- Yeah … and they go to your site less, and there’s a whole thing around that. Things are always changing, especially in media, being a creator.

[00:25:30] Like, dis- some distribution channels are always working, some are dying.

[00:25:35] Nathan: Mm-hmm.

[00:25:35] Dan: Um, some m- monetization methods are always, are working, some are dying. You know, at every, we’ve always had, like, different legs of the stool on the business side, ’cause you just, like, lean to the one that’s, like, working, you know?

[00:25:46] Yeah. Uh, I, I think for us, the subscription has always been the core, and that’s the, that, that’s the thing you wanna compound. But sometimes, like, your courses or your ads or your consulting or, like, one of those things is ripping and it’s really nice, ’cause you’re like- Yeah … “Well, my subscription has been flat for the last couple months,” or whatever.

[00:26:01] So it’s n- it’s good to be, I think, diversified as a creator, and you’re always kind of looking for what’s the, what’s the pocket that I can grow into or move into? But I do think if you’re looking at that and you’re like, “My search, my search traffic is going down,” it can be demoralizing, and you can be like, “Holy shit, but I could do-” A hundred times more than I could previously Right Um, uh, just simple examples are you can, you can legitimately over a weekend, and this will be more and more true over the next, like, six months or so, over a weekend make an app for you and your community that’s very good by yourself.

[00:26:39] And,

[00:26:39] Nathan: and totally bespoke.

[00:26:40] Dan: Yes, by yourself.

[00:26:41] Nathan: Yep.

[00:26:41] Dan: Um, uh, do you know Johnny Miller?

[00:26:44] Nathan: No, I don’t.

[00:26:45] Dan: So Johnny’s a, a good friend of mine. Um, he d- he runs this course called, uh, Nervous System Mastery. Okay. Like very cool breathwork guy. Oh, I

[00:26:51] Nathan: have

[00:26:51] Dan: seen that. Nice. Yeah.

[00:26:52] Nathan: Yeah.

[00:26:52] Dan: And he, he made this app called State Shift that he was working with someone else who was technical for a while to, like, make it, but it, like, that, that didn’t quite work out, and then he just, like, rebuilt it over a weekend with Fable and it’s not technical at all.

[00:27:04] Nathan: Work- And it’s exactly what

[00:27:04] Dan: he

[00:27:04] Nathan: wanted … works beautifully.

[00:27:05] Dan: Yeah. Yeah. It works beautifully.

[00:27:06] Nathan: And the feedback loop is so much tighter. Yeah,

[00:27:08] Dan: yeah. So now you can make an app. I, you know, some of the things that we’re thinking about are, I think that feeds used to be something that you could only make if you were a social media company with, like, hundreds of millions of users and, you know, billions of dollars.

[00:27:23] Nathan: Uh-huh.

[00:27:24] Dan: Every creator or media company can, like, s- essentially have a feed that is full of stuff that every time someone in your audience checks it, it’s, like, something that is good, that is to your taste, that is, like, sen- probably something that you made.

[00:27:38] Nathan: So typically the problem with a feed is that you need, uh, volume, like typically from a marketplace- Yeah

[00:27:44] or social network for it to be interesting and off and- Yeah … off and off. You, you check the feed a couple times and there’s one new thing- Yeah … and then zero new things. Yeah. And then the habit dies.

[00:27:51] Dan: Yeah.

[00:27:52] Nathan: So what, what are you populating these feeds if you’re n- with, if you’re not-

[00:27:56] Dan: Well- …

[00:27:56] Nathan: relentlessly creating

[00:27:57] Dan: uh, this, we’re very early here.

[00:27:58] Nathan: Yeah.

[00:27:59] Dan: Very early, and it’s unclear to me who should own the feed. Mm-hmm. Um, is the feed something that I as a consumer put together for myself?

[00:28:08] Nathan: Mm-hmm. Oh, that’s interesting.

[00:28:09] Dan: That will probably happen. Um- The

[00:28:11] Nathan: answer d- is, like, should it be this or that, probably n- the

[00:28:13] Dan: answer- It’s probably both

[00:28:14] is probably yes. Yeah, it’s, it’s probably both. Um, eh, I think that there’s a big opportunity for the Clauts and ChatGPTs of the world to, uh, let anyone make, compose their own feeds that are, that are on in Claut or GrokBots or whatever-

[00:28:26] Nathan: Mm-hmm …

[00:28:27] Dan: but that you can talk to in English And just say, “I don’t want, like, X, Y, Z thing that you keep serving me.”

[00:28:33] Like, th- that’s the difference between AI, like this generation of AI and previous generations of AI is it’s not just, um, based on re- revealed preference, it’s also based on stated preference. Oh,

[00:28:42] Nathan: yeah. So

[00:28:43] Dan: I’m always gonna look at the car accident.

[00:28:45] Nathan: Yeah.

[00:28:45] Dan: But, uh-

[00:28:47] Nathan: You can say, “I don’t actually want to.”

[00:28:48] Dan: But I

[00:28:48] Yeah, but like, d- don’t send me this. Mm-hmm. And it, it won’t. And that’s one of the reasons why when you ask ChatGPT, like, what am I into, versus when you look at your Instagram For You page, like one is … My ChatGPT one is very wholesome and my Instagram one is not. Right. You know? And it’s like, yeah, you’re gonna look at the car accident.

[00:29:07] Nathan: Yeah.

[00:29:08] Dan: Um, so I th- I do think that there’s, uh, going to be a world where, uh, the, you know, your agent makes a feed for you or several feeds. Mm-hmm. And I do this all the time for myself, like I have a feed that I check regularly of, of the meetings that happened in the company, what are meetings that, um, there was an unclear priority or there was like a 50/50 decision that I should put my finger on?

[00:29:32] Nathan: Okay. And so you’re having it read Granola transcripts- Yeah … or whatever-

[00:29:36] Dan: Yeah …

[00:29:37] Nathan: and then score it based on something

[00:29:38] Dan: We record all team meetings in Notion.

[00:29:40] Nathan: Okay.

[00:29:41] Dan: And it’s publicly available to everybody, or, uh, it’s available with anyone in our Notion. With anybody. And then I have a feed and it just tells me, “Hey, like, m- uh, you know, there’s, there’s competing priorities here.

[00:29:49] You should, like, help.”

[00:29:51] Nathan: Yeah.

[00:29:51] Dan: And so, like, that’s a custom feed for me, or we have that for, like, sometimes for hiring for, like, certain job roles. Mm-hmm. I’m like, “I wanna see everyone who’s applying and try to pick out thing- people that seem like they’d be good.” I think that’ll happen on the, on the agent side or, like, in the, the big agent platform side, but I, I also do think, like, for us, for example, we’ve started to make feeds for…

[00:30:12] We have a frontier team and- Okay … the job of the frontier team is just play with models and-

[00:30:17] Nathan: Right …

[00:30:18] Dan: try stuff and whatever. And so we, we’ve started to create, like, a feed of here’s everything that we’re doing. Mm. It’s like it’s software experiments, it’s little, little bits and bytes of research, it’s, you know, it is, it’ll eventually, like, we’re now at, we’re at now at a point where you can really make very good videos that are essentially one-shot.

[00:30:40] It’s like you talking to a camera and then it turns it into, like, a really good, like, video for, like, two minutes. Especially if you’re a team of multiple people, it’s very easy, I think, actually, to make more content than any given person would even wanna consume in a day.

[00:30:53] Nathan: Right.

[00:30:54] Dan: Um-

[00:30:54] Nathan: Well, that’s interesting, you…

[00:30:55] It’s no longer the bottleneck.

[00:30:57] Dan: It’s not the bottleneck, yeah.

[00:30:58] Nathan: Yeah.

[00:30:58] Dan: Um-

[00:30:59] Nathan: And then especially if you’ve been at this game for a while.

[00:31:01] Dan: Yeah.

[00:31:02] Nathan: Right? You’ve written a book, you’ve done- Yeah … you know, you have- Yeah … 100 back catalogs.

[00:31:06] Dan: Think about, think about how Ryan Holiday works.

[00:31:08] Nathan: Mm-hmm.

[00:31:09] Dan: Everyone can do that basically.

[00:31:11] Um, but without the- You’re

[00:31:12] Nathan: talking about the, the note cards and the level of proliferation and all that or what do you mean? Yeah.

[00:31:16] Dan: I’m sort of talking about the, the… This is actually really interesting ’cause I actually wrote, this is going back to the first AI piece I ever wrote was in, I think, 2022.

[00:31:26] Nathan: Okay.

[00:31:26] Dan: And it was, um, AI in the age of the individual, and it was like the way that we will use these tools is essentially the way that Ryan Holiday works, which is he’s off doing his, like, you know, he’s reading, he’s reading Seneca or whatever, and turning that into, let’s say, a book. But he has a whole team of people who are then turning that into a, a, a blog post or a podcast script- Right

[00:31:49] or a video or, like, all the, all these different things. Everyone now has that at their disposal, but they don’t have to pay or be the level of writer that a Ryan Ho- Ryan Holiday is. The interesting thing right now is we’ve relaxed the bottleneck. This, this is happening for us right now. So we’ve relaxed the bottleneck on- creation.

[00:32:08] There’s so much in my Slack where every time I look at it I’m like, “Holy shit, this is fucking awesome. It’s so cool.” And we do not have, uh, good enough capabilities on the editing and curation side.

[00:32:24] Nathan: Okay.

[00:32:25] Dan: Every time you add AI to one side of a process, you need to add it to the other side. We’ve added it to the creation side.

[00:32:30] We’ve not- Yep … it’s not caught up on the editing curation, like discernment side.

[00:32:36] Nathan: Mm-hmm. This

[00:32:36] Dan: is actually the same problem as the agent swarms. It’s like we can set these things off. We c- just can’t tell when they’re going off the rails.

[00:32:43] Nathan: Right.

[00:32:45] Dan: It’s just a, it’s just a cap- a capabilities mismatch. But I do think over the next year or so what I expect us to do…

[00:32:51] So for example, the way that we work right now is when a model drops, we send it, an email out to everybody. Um, but also we’ve started to send, uh, what we call frontier alerts, where we have our, our Everyagent in Slack and, um, if you’re using the Everyagent, it knows a little bit about you and- Mm-hmm … the workflows that you have and what you care about.

[00:33:13] And when a new model drops, if you should pay attention to it, we say, “Hey, this new model dropped. It’s good for the kind of thing that you care about, X, Y, Z.” Right. “You should try it.” If not, we just don’t say anything ’cause, like, we, we basically want you to be able to, like, ig- ignore it and just- You

[00:33:28] Nathan: want a very high signal.

[00:33:29] Dan: Exactly.

[00:33:30] Nathan: Mm-hmm.

[00:33:31] Dan: Um, so but that’s a really interesting system to build because- We’re not writing a vibe check. We’re, we are writing a vibe check that’s a story, but there’s also, it’s gonna go out to people in this, like, custom way. It’s bespoke. So we’re building a system that has to know how to write for each person.

[00:33:49] Nathan: Mm.

[00:33:50] Dan: And s- and so we’re sort of moving up a level and then you, then your, your editors are, like, looking at, uh, okay, this message went out to this person. They had this reaction. Um, what should that teach us about how we should change the system or how do we, how do we make it better at writing in the future?

[00:34:06] So, so everyone’s moving up a level- Right … and the, what’s the output is you’re not necessarily looking at every single output- Mm … but you’re making sure that each output, like, carries your taste, and that’s the whole game. And it’s, um, you know, there’s a lot of analogs with having a team, um, and hiring people and making sure that they output stuff.

[00:34:25] Like, if you have a ghostwriter, for example.

[00:34:29] Nathan: How do you think about hiring right now? You know, you, in your interview with Sam Altman, you were talking about the sheer number of developers. Y- like, AI development is better than it’s ever been. Mm. It’s getting better every single week.

[00:34:41] Dan: Mm-hmm.

[00:34:42] Nathan: And so we’re hiring more developers than ever- Yeah

[00:34:45] which is the opposite of what the layman would expect.

[00:34:48] Dan: Yeah.

[00:34:48] Nathan: Uh, and so I’m curious for your take on that, and then also how you think about hiring within Every, Every.

[00:34:53] Dan: You would imagine if you’d told me, like, uh, five years ago that we would have a model that was as good as Fable or Astra- Mm … that I probably wouldn’t need any engineers, and we have plenty of engineers, and we’re hiring more.

[00:35:04] Nathan: Right. Same.

[00:35:05] Dan: Yeah. Um, and I think there are- th- really interesting reasons why that is structurally true. It doesn’t mean that, um … I do think probably m- macro y- you will be able to have companies that scale to larger sizes with smaller teams, but doesn’t mean that you don’t need engi- any engineers. I would project the job of engineer to be a job that, like, hiring increases over- Yeah

[00:35:37] like, in, in total in the economy. And one reason for that is now we live in this world where, you know, everyone can YOLO a pull re- pull request to the website. Who’s gonna be the one to make sure that that all works together well? Yeah. Like, yeah, you can have your super intelligent model and it might say no, but, like, the minute you say, “But yes, you should do this,” it’ll just do it and then- Right

[00:36:00] suddenly you have a whole hairball, you know?

[00:36:02] Nathan: Yeah.

[00:36:02] Dan: So you actually, when everyone can make stuff, you actually increase the demand for engineers who can, like, build systems to make sure that everybody, all the stuff that people can make is used well. And then also on the other side, um, the, the ambition, the level of ambition that you can go for is so high.

[00:36:24] Mm-hmm. It’s so high. Like, there are people on my team who are just, like, one-shotting real production level, like, pro software and it’s like cr- it’s crazy, and that’s just for themselves.

[00:36:36] Nathan: Mm-hmm.

[00:36:37] Dan: And, uh, so that opens up all these different new things to do. But I think that’s why I’m not particularly worried about engineers.

[00:36:44] Nathan: Right.

[00:36:45] Dan: I think the job of engineer changes a lot- Mm … and the kinds of minds and thinking that are maybe re- rewarded might change to some degree- Mm … which is an interesting and important topic I think to, to dig into. But, um, there’s st- there’s lots and lots of demand for this.

[00:37:02] Nathan: If we’re diving in on things that change, uh, you have a take that is going, uh, trending on X at this very moment.

[00:37:09] And that is on the future of newsletters and the inbox, which is a topic that you and I both care about a lot- Yeah … because we’ve built our businesses- Yeah … around this very thing.

[00:37:18] Dan: Yeah.

[00:37:18] Nathan: So, uh, what’s the take, and we’ll dive in on

[00:37:21] Dan: it. It’s so funny, we were talking about this in the, in the pre-production and it’s like I fired off that take, I gave it no thought, and it’s like way more viral than, than this, like, 8- Than the piece you spent

[00:37:29] 8,000 word piece that I, like, slaved over for, like, three months or whatever. Um, so, but so it goes. Um- The spicy part of the take is, like, the newsletter is dead.

[00:37:39] Nathan: Mm-hmm.

[00:37:39] Dan: But what I

[00:37:39] Nathan: re- Says the person who has, what, over 100,000

[00:37:42] Dan: subscriptions. Yeah, 120, 130, yeah.

[00:37:43] Nathan: So why is that? Like, what are you seeing?

[00:37:45] Dan: The thing I mean by that is n- not

[00:37:50] And the way people took it, which to be honest, I was like, I knew what I was doing by, like, saying that. It’s

[00:37:55] Nathan: okay to be misunderstood- You know?

[00:37:56] Dan: Yeah … on the internet because it- It’s, like, good. Usually. You know? Like, I knew what I was doing. It leads

[00:38:01] Nathan: to more virality.

[00:38:01] Dan: Yeah, yeah. The thing I meant by that is for a long time- It has been the best advice and the conventional wisdom that You, all you have to do as a creator is get a person’s email

[00:38:19] Nathan: And then you, like, have that relationship.

[00:38:21] Dan: Yeah. You’re set. Like, you own the relationship.

[00:38:22] Nathan: Mm-hmm.

[00:38:23] Dan: And that has been sort of cracking and crumbling for a while. Uh, specifically the newsletters tab, the, and the promotions tab has been like- Yeah … a, a shot at that where, yeah, you’re really not actually guaranteed. And- Mm … and so now there’s all these workarounds where it’s like, you know, mark it as priority so it doesn’t end up in whatever.

[00:38:41] Nathan: Reply is

[00:38:41] Dan: m- making a big difference. Yeah, all that kind of stuff.

[00:38:43] Nathan: Yep.

[00:38:43] Dan: And I think we just saw … We’re, we’re seeing a new bump, a new, like, level in that. Uh, it’s, like, escalated a lot with, you know, dots or Grok bots or, you know, all these other tools where I, I really don’t look at my inbox that much.

[00:38:58] Nathan: Yeah.

[00:38:58] Dan: I really don’t.

[00:38:59] I look at Slack a lot, but, uh, mostly my, my dot handles everything and then I go into the, my inbox every once in a while for, like, I just need to do something really quick.

[00:39:09] Nathan: Mm-hmm.

[00:39:10] Dan: And so I just … I’m not even encountering my newsletters tab. And if I’m doing that now, it’s gonna take a while for everybody to do it.

[00:39:20] Nathan: Right. Yeah, someone in the comments was like, “Yes, but you’re at the .01%.” Yeah. And you’re like, “Okay, great.”

[00:39:26] Dan: Yes.

[00:39:26] Nathan: So what are we setting as the time horizon? Yes, exactly. It, it’s not like, oh, so it’s not gonna happen. Yeah. It’s like, so just when?

[00:39:32] Dan: Yes, exactly. That’s- I,

[00:39:33] Nathan: we’re not saying three to four weeks from now.

[00:39:34] Dan: Yeah.

[00:39:35] Nathan: You know?

[00:39:35] Dan: Over the next couple years.

[00:39:36] Nathan: Yeah.

[00:39:37] Dan: Um, and, and not only that, but the models will be so much better that, like, for sure, I think the medium of email-

[00:39:43] Nathan: Mm-hmm …

[00:39:43] Dan: will still be around. Like, you’ll still wanna use, like, SMTP or whatever to, like, send texts back and forth, but you will absolutely not be i- in general looking at a list of, uh, uh, last in, first out ranked list of- Right

[00:40:00] emails that you have to deal with.

[00:40:01] Nathan: Mm-hmm.

[00:40:01] Dan: Right? You’re gonna have your assistant be like, “Hey, like, three things came in. What do you want me to do?” And you go like, “This, this, and this,” and then- Yeah … done. The thing that that misses, obviously, is … I mean, my, my dot has never been like, “Hey, this newsletter came in that you should read that you would like.”

[00:40:16] Um, I, I now have it, I say every time every publish is, like, send me something.

[00:40:20] Nathan: Right.

[00:40:21] Dan: Um, ’cause I’m, like, experimenting with this ’cause I think there’s, that’s a new playing field that I think is gonna be really important. But I think very few people are thinking in that way. Mm-hmm. And it’s gonna be a rude awakening in two years when you’re like, “My open rate is zero,” or it’s 100%, but, like- Right

[00:40:40] no one is interacting with it or with my stuff.

[00:40:42] Nathan: It’s not, it’s not the humans behind it.

[00:40:43] Dan: Yeah. If you’re a writer on the internet, you are … You’re, you’re writing stuff you think is great, and you are also thinking about what subject line is gonna work and, like- Mm-hmm … all that kind of stuff, and the rules are gonna change a lot because the first thing that’s gonna see the email is it’s not Google’s promotions filter, it’s Grok bot.

[00:41:03] Nathan: Mm-hmm.

[00:41:04] Dan: That’s very different.

[00:41:05] Nathan: Yeah, and you could tell it, like, “Hey, when this …” So I had Seth Godin on the podcast, and, uh- He was like, “How do you, how do you become a creator who is so good that you’re missed when you don’t publish?”

[00:41:17] Dan: I agree. I think that that’s like, that’s the, the true size of your audience is, um, if, if you’re somehow you always get into the promotions tab, like, who goes and finds you again.

[00:41:29] Nathan: Yep.

[00:41:30] Dan: You know?

[00:41:30] Nathan: Like, yeah. Yeah. Those, those are the people. And so that’s the thing where someone i- they prompt and they’re like, “Why, why hasn’t Dan written anything recently? That’s so weird.” And it’s like, “Oh, because my Grok bot or my- Yeah … DOTs has been filtering all of that out,” and so then I’m prompting it saying, “Hey, I actually do wanna read that.”

[00:41:45] Dan: Yeah.

[00:41:46] Nathan: And so the bar, it’s kind of like a dragging from the promotions to the inbox, but it’s like, it’s on… It’s another level- Yeah … of it.

[00:41:56] Dan: And, and I think it’s so early that right now I’m like, cool. Every, I read every… Or, you know, my team writes it or-

[00:42:03] Nathan: Yep …

[00:42:04] Dan: whatever. Um, I want, I want that in my inbox. I haven’t done that with anybody else.

[00:42:10] Mm. I will probably over the next five months decide Nathan’s got a great newsletter. Mm. Like, also send me, but then okay, what, what’s gonna, what’s gonna happen? The o- the obvious thing is gonna happen, I’m gonna start getting a bunch of notifications from my bot that’s like, from stuff that I don’t really want.

[00:42:26] Nathan: Yeah.

[00:42:27] Dan: And then I’m gonna try to tune it, and then OpenAI or Claude is gonna, like, come out with an inbox. Right. But it’s gonna be different. Mm. It’s gonna not look like an email inbox in the same way. It’s gonna be, “Hey, we like…” I mean, we’ve been doing this for a long time. We have this, um, we have this email agent we, we built over the last two years, it’s called Quora- Mm

[00:42:47] that summarizes all your, all your emails. It, like, looks at all the stuff that you need to… Looks at all the stuff that comes in, it filters out, uh… It, it makes sure you see anything timely in your inbox, and then it just summarizes the rest, so you just, like, read one thing and you’re done. They will absolutely have that in ChatGPT and Claude.

[00:43:06] There will have to be… Well, A, the game for creators will be how do I make sure that I’m included in that- Right … and rank well on that so that people click on it and then read my stuff? Which means how do I write it so that Claude thinks it’s important?

[00:43:21] Nathan: Mm-hmm.

[00:43:21] Dan: Um, and then I think on the OpenAI and Anthropic and, you know, Google’s side, it’s gonna have to be- How do we, h- how do we create a new playing field or a new platform that works for people?

[00:43:37] Because people wanna read, they wanna read from the people they like.

[00:43:40] Nathan: Yep.

[00:43:40] Dan: Uh, but the physics are all different here, so they need to be figured out.

[00:43:43] Nathan: So I’m thinking about that in particular. If w- I, I obviously have my, the last 13 years of my career built around email and newsletter specifically. So I always think about, one is whatever’s coming next is going to kill email, right?

[00:44:00] Because it’s been, uh, forecasted many, many times. It

[00:44:03] Dan: won’t kill it.

[00:44:04] Nathan: It … Yeah, and so but then trying to break it apart and, like, what are the component parts of it? So the way that I’ve thought about it is, um, email right now is a unique identifier, you know, of like, okay, I can reach you at your email address and, and that sort of thing.

[00:44:19] And for whatever reason, that’s become the thing that we place in all these spots around to be like, “Hi, this is who I am.” Yeah. It’s a, as you mentioned, like, it’s a communication protocol of, like, SMTP, um, and it’s a few other things, but those in particular I’m like, okay, what actually gets replaced? People would say, like, oh, SMS, um, or I guess RCS, right, is gonna replace it or, you know, WhatsApp or Signal or these other things.

[00:44:44] My, my take and I- I’m curious for your thoughts on it is I, I watch, like, uh, Zuckerberg and Altman and whoever else, they like … Like, I can’t see OpenAI being like, “You know what? Let’s bet everything on WhatsApp as the communication protocol and let’s run all of our-

[00:45:01] Dan: No, no, no …

[00:45:02] Nathan: things through Zuckerberg.” Like-

[00:45:03] Dan: They

[00:45:03] Nathan: won’t do that

[00:45:03] it’s not gonna happen.

[00:45:04] Dan: They won’t do that. Um, your agents will connect to email. Mm-hmm. The … I think the, a better- It’s the

[00:45:09] Nathan: inbox place that’s gonna be-

[00:45:10] Dan: Yeah. I think a better analogy w- might be When you meet someone at a conference and you bump phones- Yep … you exchange your phone number.

[00:45:19] Nathan: Mm-hmm.

[00:45:20] Dan: But you’re not leaving them a voicemail.

[00:45:22] Nathan: Right.

[00:45:23] Dan: You

[00:45:24] Nathan: know? And actually, the phone number is not even relevant- Yeah … ’cause we’re gonna, we’re gonna text over

[00:45:26] Dan: iMessage. You’re gonna text and then you’re gonna FaceTime or whatever.

[00:45:29] Nathan: Yep.

[00:45:29] Dan: And so I think the, the n- the email, email as a network, as a communication substrate- Mm-hmm … is obviously very stable.

[00:45:37] It’s gonna stay- Yeah … stay that way. But, uh, who is sending and receiving those emails?

[00:45:44] Nathan: Mm-hmm.

[00:45:44] Dan: Who? Um, and then what is the, what is the f- like, product surface that the eventual email owner is looking at is gonna be very different.

[00:45:54] Nathan: Mm-hmm.

[00:45:55] Dan: And those will have very different mechanics to them that right now, if you’re a newsletter writer, you have not built your business for that world ’cause it hasn’t existed.

[00:46:05] Nathan: Right.

[00:46:06] Dan: But it will exist. So, uh, y- y- there will be some value, for example, to having a person’s email because their agent’s gonna read it-

[00:46:16] Nathan: Mm-hmm …

[00:46:17] Dan: for sure. But it’s not the same guarantee that the human is gonna read it that it used to be. Mm-hmm. You’re gonna have to do other things to make sure that that happens.

[00:46:26] Nathan: Yeah. What do you think, like, how are you positioning Every? Like, the, ’cause the newsletter’s always been at the core of what you’re doing. Yeah. And then now you have this, this insight, somewhere between hot take prediction and insight. You know? Of you’re like, okay, this is where it’s going, and as an entrepreneur, our job is to have those sorts of insights and then make decisions- Yeah

[00:46:46] that result in monetary value around that.

[00:46:48] Dan: Well, this is, uh, A, this is, like, pretty- Uh, new- Yeah … for me. Um, B- Hot,

[00:46:55] Nathan: hot off the press.

[00:46:56] Dan: Yeah. B, I do think we’re already doing a bunch of stuff that’s like, okay, we have frontier alerts.

[00:47:02] Nathan: Mm-hmm.

[00:47:02] Dan: You know, we’re- Right,

[00:47:03] Nathan: so you’re, you’re, you know, the same way that we, you know, we used to do, like, push notifications in iOS, you’re like, okay, why have push notifications into your Slack-

[00:47:11] Dan: Yeah, into your Slack

[00:47:11] if

[00:47:11] Nathan: you have the Slack

[00:47:12] Dan: integration. We’ve got frontier alerts. We’re gonna have, uh, we’ve got feed- we’ve got a feed on our site, so maybe you’re, you’re checking our site. I mean, I one-chatted an app last night that, like, maybe we should have an app. You know, like- Mm … we’re gonna start exploring in all these different places, and we have

[00:47:25] We build soft- we build, like, real software that, um, a lot of people use and a lot of companies use. So I’m not worried for us. I, but I am … Uh, the way that it, it changes my mind strategically is I’m like, okay, our quarterly goal right now is how many emails we get. I think that’s fine for this quarter, but if I’m thinking about next quarter, is that the number that I- Mm

[00:47:51] is that the number I want? Or, for example, should I focus more on our AEO SEO? Right. Because if you’re ranking really well for AEO right now, there’s a really good chance that that’s going to be a big signal that goes into whether the agent, like, lets you through-

[00:48:08] Nathan: Mm-hmm …

[00:48:09] Dan: eventually. I’m just … I’m making stuff up right now.

[00:48:11] Yeah. But, like, n- that’s the kind of stuff that I’m like, okay, I need to be experimenting with what is the, um, what are the new form factors that people are gonna wanna consume us in, in new channels that are being opened up, Slack, our own feeds, apps, you know? Uh, okay. A b- a b- a big one is everyone’s working in Claude and ChatGPT.

[00:48:35] Now we have an MCP server. Can I get them to install our- Yeah … MCP server and, like, tell them when a new article comes out? And these are all gonna be, like, very early and kind of rough and not gonna work, but in a year it’ll be very different. Yep. And I’ll, I’ll have kind of created … I’ll have done enough experiments to understand what the shape of the right solution is that we can double down on.

[00:48:53] Nathan: Yeah, that makes sense. Can you push content through an MCP?

[00:48:56] Dan: Yeah. Well, well, so MCP servers are, like, the, like, Claude or ChatGPT would pull, would pull the server. Okay. So, like, every day it’s, like, you know, seeing is there anything new? However, really exciting is OpenAI recently introduced this thing called MCP events.

[00:49:13] Nathan: Okay.

[00:49:13] Dan: Um, so you, you can actually push to a person’s ChatGPT. Mm. And I think that’s a huge deal.

[00:49:21] Nathan: Do you think that the other platforms will- Absolutely. Like, if, if it takes off, they’ll adopt it. They’ll

[00:49:24] Dan: do it. Yeah,

[00:49:24] Nathan: yeah. Yeah. That’s such an interesting thing of, like … I mean, it’s fascinating that OpenAI created the closest thing to- magic-

[00:49:33] Dan: Mm

[00:49:33] Nathan: that we have ever seen.

[00:49:34] Dan: Mm-hmm.

[00:49:35] Nathan: And it has almost no mode.

[00:49:36] Dan: Yeah.

[00:49:36] Nathan: Right? Because it’s like, “Oh, this model kind of annoyed me, so let me from a dropdown-” Yeah, yeah. “… select another thing.” You know, and you’re like, “This is the greatest invention that society’s ever had,” and it’s like, “I don’t know, man, I think I’ll just switch over to Gemini.”

[00:49:47] It is

[00:49:47] Dan: a very interesting race to be a part of and to s- and to watch unfold.

[00:49:52] Nathan: Yeah. It’s wild. Before we move on, so in the, thinking about the future of newsletters and all of that- Yeah … is there anything else that you think creators should be doing today to get ready for that?

[00:50:01] Dan: I mean, my, my general advice is Use the tools.

[00:50:06] Nathan: Mm-hmm.

[00:50:07] Dan: Probably don’t use them because you’re afraid. Like, find things- Yeah … to do with them that you’re genuinely like, this- think this is awesome.

[00:50:14] Nathan: Like, what have you always wanted to exist in the world? Yeah. And it’s like, okay, then try to make that happen.

[00:50:17] Dan: If you’re a creative person, now is so cool. And I know that it, you know, I, I love writing.

[00:50:26] Nathan: Mm-hmm.

[00:50:27] Dan: And I love just putting one word after another.

[00:50:31] Nathan: Mm-hmm.

[00:50:31] Dan: And I’m not saying you should just, like, one-shot all your writing and then whatever. It’s like, no. And when I’m five hours into a writing session and I’m like, “Fuck, I have to reorganize this section,” and I can just be like, “Go do it,” that’s really great.

[00:50:45] Nathan: Right.

[00:50:46] Dan: That’s really great, and it means I can do way more and way more interesting things. Like, the level of ambition of this piece is very high. Uh, this c- you know, how Codex happened piece. Right. It’s like, you know, it’s 8,000 words. We have, you know… It’s, there’s all these custom designed elements on the page.

[00:51:01] It’s full-

[00:51:01] Nathan: They animate as you scroll.

[00:51:03] Dan: Yeah. It’s fully agent native, so not only do you have the piece that I wrote, but you have access to all of the underlying interviews that I wrote and all of the like-

[00:51:10] Nathan: Oh, wow …

[00:51:11] Dan: uh, all of the, like, quotes are linked so you can click and see where the, uh, uh, w- you can see the point in the interview where the person said that.

[00:51:19] Um, and then you can have your agent read it and be like, “What did Dan leave out? What did he miss?” So, like, what are the context things that I’m missing? Mm-hmm. Like, all that kind of stuff. Or you can say, “Hey, like, uh, there’s this really good lesson in this piece. Like, can you help me understand it more or bring it back the next time I’m making this decision?”

[00:51:33] Right? So-

[00:51:34] Nathan: Right …

[00:51:35] Dan: there’s all these things now that, that I can do that, uh, A, help me be better at the thing that I love to do and, and are becoming their own craft, but also there’s new opportunities for formats and mediums because, yeah, there’s… Whoever thought of, like, an agent native article? Like, that’s- Yeah

[00:51:53] that has not, never been possible before. There’s all this opportunity to do video and games and it’s just, it’s really cool.

[00:51:59] Nathan: Yeah. Something else that I think creators should focus on is just the highest quality content.

[00:52:04] Dan: Mm.

[00:52:04] Nathan: Like, the kind of thing that will stop the scroll in the feed or, like, this is so good.

[00:52:08] Something that stands out to me about Every as a company is, yes, you have 120,000 people on your newsletter. Um, I bet there’s very few people, like very few creators that you would trade your newsletter list for.

[00:52:21] Dan: Mm.

[00:52:22] Nathan: Who, like, I can think of maybe a couple people that have the quality of a list-

[00:52:26] Dan: Mm …

[00:52:26] Nathan: uh, on par with what you have.

[00:52:29] Dan: Mm-hmm.

[00:52:29] Nathan: Um, we recently turned on subscriber signals for- Yeah … uh, for Every, and going through that with you, it’s just like, I w- I won’t name the specific names, but it’s, like, the CEOs of all of these companies, the top writers, all this. Like, you’ve built a, an insanely high quality audience. Thank

[00:52:45] Dan: you.

[00:52:45] Nathan: And it’s because you’re talking about a topic that everyone is ob- is obsessed with.

[00:52:51] And then you’re also doing it to a level of detail and quality. And so I bet even if the inbox changes or goes away in that way, people are still gonna be seeking out your work in whatever format. So that’s the first thing I would say is, like, focus on, okay, how can you… Like, quality matters more than ever.

[00:53:09] Dan: I totally agree. A- and, and most of what I’m talking about is about for g- for sure, if you are mostly relying on tactics to- Mm-hmm … like, get distribution, like, all the tactics are gonna change. Yeah. Right? But, like, if you’re a great writer, people are gonna find you. Mm-hmm. Um, and even if you’re a great writer, you’re still have to pay attention to some of these shifts- Mm-hmm

[00:53:31] because that’s how people see you, and that’s just sort of- Yeah … the way the game is played.

[00:53:34] Nathan: Hey, if you wanna master the skill of making money, make sure to pre-order my book, The Ladders of Wealth. It’s gonna help you learn exactly what skill you need next to go from earning a living to building wealth.

[00:53:44] The book comes out March 2nd, but if you go to ladders of wealth.com right now and pre-order the hardcover,

[00:53:50] Dan: I will send you the full e-book and the audiobook for free, and I’ll get them to you early. So go to laddersofwealth.com to learn more. I’d love to get you early access.

[00:54:00] Nathan: Are there any opportunities that have come up from having, like, building an audience?

[00:54:03] And I’m thinking about, of a bunch for you but are there any opportunities that have come up from building an audience to this quality that you’re just like, “I can’t believe this person is reading or this opportunity is…”

[00:54:13] Dan: I mean, the whole, my whole life is from this, basically. Right. It’s fucking, it’s cra- it’s really crazy.

[00:54:18] Um, and I get to meet people that are, you know, are heroes or that I’m- Mm-hmm … like, I can’t believe you wanna, you’re asking me for my input on this thing. Right. Like, I’m, I just write a little newsletter or whatever, you know? Um, I feel like there’s this crazy important technology change happening, and I’m just, like, sitting right in the middle of it.

[00:54:41] And not just sitting in the middle of it, I get to, uh, explain it to people who are a little bit further outside, and also interpret it for the people who are even deeper into it than I am, ’cause they need someone to do it. And, like, that’s, it’s an amazing role to play as a writer. That’s, like, what you wanna be doing is, um, as this new world is, is- Unfolding to help people understand how to see it and think about it.

[00:55:09] Nathan: Mm-hmm.

[00:55:09] Dan: And that’s partly a, a, an active observation of just, like, being like, “Here’s what’s here,” and partly a creative act of, like, what could it be or should it be, and how do I see it? And I, I, you know, I think it’s the best.

[00:55:21] Nathan: Well, I think one of the things that I am both wildly excited by and struggle with simultaneously is I feel like I’ve been given these tools that are so powerful that I’m, I’m not even thinking about them in the right way of what’s possible with it.

[00:55:35] Mm-hmm. And so I’m like, “Oh, it can do all of this.” Things that I used to have five engineers work on building or all of this, I’m like, “Oh, it just kind of works right out of the box.”

[00:55:43] Dan: Mm-hmm.

[00:55:43] Nathan: Like, an example is, uh, I always do… You know, I meet creators, I always wanna know what, what newsletter platform are they using?

[00:55:49] What, what’s their tech stack look like? And so, and that’s a hard problem to solve because every good newsletter platform works really hard to prevent bots from signing up for it- Mm … right? To prevent list bombing and all of this stuff, including Kit. But now like, without me even telling it, I didn’t, did not even create a skill for it to do this.

[00:56:08] Um, I mean it helps that, like, GroqBot has, uh, access to our CRMs to be able to see who’s a Kit customer. But it will go on its own, it will go check the sign up, the code on the website. It will check the DNS records to see if there’s an MX record tied to MailChimp or whoever- Mm … or Kit or whoever else.

[00:56:25] And so it just, it knows all of these things, and I feel like I’m constantly, like, asking it to do, like, 201 level tasks. Mm. And, you know, if I, if it was a person, it’d be sitting back and be like, “Bro, you have no idea what I can do.” Like, like, push me to some limits, like- Yeah,

[00:56:41] Dan: yeah …

[00:56:41] Nathan: you know, be way more ambitious and take on some way bigger things.

[00:56:44] Dan: Yeah. Well, I, I get that all the time. We have a, um, we have this, one of our most popular articles, um, it’s called The Eight Levels of AI. It’s by our head, our head of evals, Mike Taylor, and it’s just, it just lays out here’s- your baby prompter to your orchestrating like- Mm … a team of agents. And what people tend to do is just take that and put it in their Rock Bot or their Claude and be like, “What level am I at?”

[00:57:10] Nathan: Mm.

[00:57:11] Dan: And then every week I want you to tell me what are the things I might try to like get to the next level, and works really well.

[00:57:16] Nathan: That’s probably the most important shift, and I’m … if I’m honest, I’m only halfway through making it.

[00:57:20] Dan: Yeah.

[00:57:20] Nathan: The, the, the trap that I tend to fall into is thinking what should I be doing?

[00:57:25] Oh, let me try this.

[00:57:26] Dan: Mm.

[00:57:27] Nathan: And the simple reframe is just saying, “What should I be doing?” Mm. And just ask the AI- Yeah …

[00:57:32] Dan: what

[00:57:32] Nathan: to do. Just

[00:57:32] Dan: ask. Yeah. It’s, it’s like it’s so unsatisfying, because people are like, “How do I do that?” And I’m like, “Just ask.” You know? Yeah. That, that’s why we made this like prompt and this thing, ’cause it’s like- We

[00:57:41] Nathan: were texting about something.

[00:57:43] I can’t remember what it, what it was. And you said, “Did you try asking the godlike-” I’m sure … “super intelligence?” And I was like, “Oh,

[00:57:50] Dan: yeah.” Yeah. Yeah. It’s just like the main skill is just realizing I should just ask this thing.

[00:57:58] Nathan: Right. Which is so bizarre.

[00:58:01] Dan: Yeah.

[00:58:02] Nathan: Um, I wanna dive in a little bit on how Every works as a company.

[00:58:04] Sure. Um, so the business model, you make money in a few different ways. Yeah. As I understand it, you’ve got, uh, the subscription, that’s the main one. Yeah. People pay what, 20 bucks a month?

[00:58:14] Dan: 30.

[00:58:15] Nathan: 30 bucks a month and get everything. Everything. That’s in the name. Yeah. You do some brand sponsorships and- Mm-hmm

[00:58:22] work like that. Uh, you do some consulting.

[00:58:25] Dan: Yep.

[00:58:26] Nathan: What am I missing in there? Is that … Th- those are the main two buckets? We have

[00:58:28] Dan: courses.

[00:58:29] Nathan: Okay.

[00:58:29] Dan: Um, I think that’s most, I think that’s most of the business.

[00:58:33] Nathan: Okay. Yeah.

[00:58:34] Dan: Uh, like the, the core of the business is subscription.

[00:58:36] Nathan: Mm-hmm.

[00:58:37] Dan: And that’s the thing that we try to grow.

[00:58:39] Um, the other stuff matters and has been a really nice cash flow, ’cause we’re like- Mm … we have not raised a ton of money.

[00:58:47] Nathan: Yep.

[00:58:47] Dan: I look at it as it’s … it helps us fund the rest, the subscription flywheel. Yeah.

[00:58:53] Nathan: Something that I’ve been really curious about is like your product studio approach.

[00:58:57] Dan: Hmm.

[00:58:57] Nathan: And you talked about this, um, at Lenny’s conference, and this idea of pirates versus architects.

[00:59:04] Hmm. And I’m so curious how you approach this product development. Um-

[00:59:08] Dan: Yeah, so we, uh, we have a pr- a product team. Um, and they’re responsible for, for example, building the agent. Um, and that’s a product that has customers that like we’re trying to improve all the time, that is … needs to have a stable roadmap.

[00:59:22] Nathan: Mm-hmm.

[00:59:22] Dan: The frontier’s always moving, and our job is to be at the frontier. And for a while I was like, “It’s everyone’s job to be at the frontier,” so we all always have to be experimenting and, oh my God, this new thing came out, like let’s push it into the agent or like let’s push it into whatever, whatever other product we have.

[00:59:41] And that is very chaotic. There’s something, like, important about that, which is if we never incorporated the new stuff, we’ll wake up in six months and be like, “Uh-oh.”

[00:59:52] Nathan: We don’t have a business. ”

[00:59:53] Dan: That’s bad.” Yeah.

[00:59:54] Nathan: Yeah.

[00:59:54] Dan: Um, but it can’t be, like, everyone’s job to be constantly playing with new stuff ’cause n- nothing will get done.

[01:00:01] It’s, it’s chaotic, it’s confusing. Um, and some people love to play, play with new stuff, some people don’t. Both people are valuable So what we did is, uh, I established a frontier team. Frontier’s job, just play with new stuff all the time. Constantly be testing new models, building experiments. Um, and then we have a product team who’s like, “We’re gonna make the best possible fucking product.”

[01:00:27] And what we’re trying to do is move things from the frontier to the product team as they get more tested out and more, like, proven. And so the frontier team stuff, it always just starts as experiments that basically… Or they’re, they’re content, um, that tell us about, like, is this new little feature something that we might wanna do?

[01:00:48] So, like, a, a good example is, um, there’s this model that came out called JEV, which- Yeah … it just does really, really fast classific- classification. Um, and the, the frontier team immediately… Like, the day it came out, we had, like, this big vibe check and, like, a bunch of pe- a bunch of people on the frontier team made feeds and made all these, like, demos and whatever.

[01:01:06] And, um, then someone on the agent team was like, “We should use that to make frontier alerts.” So, like, you just sort of-

[01:01:14] Nathan: Oh, to decide if- You,

[01:01:15] Dan: you, like, push it … who it

[01:01:16] Nathan: should go to.

[01:01:16] Dan: Yeah. We, we just sort of… We say, “Here’s, here’s what’s possible now,” and then the product team can be like, “Ooh, that actually works really well for what we need.”

[01:01:23] The

[01:01:23] Nathan: product team, like, gets to select from the frontier team-

[01:01:25] Dan: Exactly …

[01:01:26] Nathan: of, oh, that rises- Yeah … to what

[01:01:27] Dan: should go to- Yeah. And, and, you know, there’s a thousand things that the frontier team has done that the product team has totally ignored. Which is fine. Yeah. That’s, like, part of it, you know? And I think that gives you a little bit of the best of both worlds of we’re exploring, but we’re also exploiting, and we’re not being distracted over here, but we are, like, creatively, like, on fire over here.

[01:01:46] So

[01:01:46] Nathan: before you were taking each person and saying, “I need you to carve out 25, 50% of your time- Yeah … I need you to live in both worlds.” Yeah. And you switched that and you split it up and said- Yeah … “You’re over here, you’re

[01:01:56] Dan: over there.” Yeah, exactly. And then within the frontier team, when you’re exploring something new, I think there are two main archetypes of people.

[01:02:03] There’s pirates and architects. Pirates are like, “I’m just gonna, like, go do a bunch of stuff. That’s me.” You know? Yeah. Um, and architects are like, “Okay, you have something that’s, like, kind of working, but it’s, like, extremely messy and un- unfocused. Like, I’m gonna try to, like, help you narrow it in into something that, like, works well.”

[01:02:19] So architects help you move it up the, up the frontier, up, up the idea pipeline stack from something that’s, like, totally messy, completely vibe coded, to something that, like, you could look at it and see, oh, maybe more of the team should be using this.

[01:02:35] Nathan: Right.

[01:02:35] Dan: Um, and then the product people can look at it and be like, “Oh, maybe we should release to customers.”

[01:02:40] Nathan: Mm-hmm.

[01:02:41] Dan: Yeah.

[01:02:41] Nathan: Yeah. I think that’s really interesting. Something that I wanna do more of i- at Kit is build some of these, like, one-off features, ideas. Part of the reason we built our, our app store is to make the product totally extensible.

[01:02:54] Dan: Mm.

[01:02:55] Nathan: And so now you can vibe code. You would not wanna vibe code the core app that sends 3 billion emails a month and has, uh, you know, hundreds of thousand plus active users.

[01:03:06] And we can’t let every random person into our code base. But with the App Store, you know, we have all of the, the templates and the tutorials and all that, so anyone can vibe code an app. And they’re like, “You know what? I want this functionality. It should exist.” And so I, I prompted it and it does exist now.

[01:03:19] Um, but that’s allowed us to test and iterate a lot more. But it’s very easy to do the the, like, pirate that work. And we’re quite good at the scalable work. Mm-hmm. But the in between is hard, and so that’s like, that architect role makes a lot of sense to me. But what I think about is the ongoing support- Mm

[01:03:42] of each one of these things. Yeah. And this is a problem that I haven’t solved, is like- Yeah … oh, I could easily… Like Kit does not have an iOS app.

[01:03:47] Dan: Yeah.

[01:03:48] Nathan: We should.

[01:03:49] Dan: Yeah.

[01:03:49] Nathan: But I’m like, “Oh, now I have this steady stream of- Yeah … tickets forever.”

[01:03:53] Dan: Yeah.

[01:03:53] Nathan: And I don’t know how to solve that.

[01:03:54] Dan: We have the same thing. Um, the, the way that we have solved it, and it’s not perfect, but the way we’ve solved it is anything we launch as an experiment, we don’t support.

[01:04:06] Nathan: Mm.

[01:04:06] Dan: Like, you should know.

[01:04:08] Nathan: Like it’s in the labs.

[01:04:09] Dan: Yeah. We’re launching this, we’re never gonna support it. Mm. Don’t submit a ticket. Um, ’cause we’re just gonna, like, we’re just trying stuff, and people know that. Yeah. And that’s the deal, and it’s, like, clearly marked. And then when something feels proven out enough that we’re gonna invest, that’s when we’re like, “Yes, we’re gonna support this.”

[01:04:23] Mm. It’s, like, an ongoing part of the business and all that kind of stuff- Mm … and we’re not gonna, like, uh, just let it, let it

[01:04:28] Nathan: ride. So the

[01:04:30] Dan: deliberate classification of- Deliberate classification …

[01:04:31] Nathan: this is an experiment or in the labs.

[01:04:32] Dan: I do also think that in the next six months for apps that you want to keep just, like, kind of working- Mm

[01:04:42] in maintenance mode, the cost is gonna be very low.

[01:04:44] Nathan: Yeah.

[01:04:45] Dan: Um, it, you know, it already is pretty low, but there’s a lot of, there’s a lot of work you probably need to do to, like, set that up. But six t- six months to a year, it’d be pretty low to just, like, go from email about a bug to an agent has triaged and fixed it, and then emailed- Yeah

[01:05:01] the customer, um, for, you know, simple apps. Uh, so-

[01:05:06] Nathan: You’re right. At that screen size it does have that issue.

[01:05:09] Dan: Yeah, exactly. Yeah.

[01:05:11] Nathan: That’s fixed now.

[01:05:11] Dan: So I, I, I don’t think the ongoing maintenance costs are gonna be that h- high, but the more of these things you have, the more messy it is. Like, things break- Right

[01:05:20] even, you know, so it’s, it still will be something that you’re thinking about, and the best way to deal with it is to be deliberate about… well, make a distinction between we’re releasing this and this is just an experiment, versus we’re actually gonna support this, and be deliberate about when you change something from an experiment to something you’re supporting.

[01:05:37] Nathan: Right. Yeah, that makes sense. I’m gonna play with that more because I mean, we’re already doing that inside of Kit where, you know, so many of these pull requests, it will… Like, when you, the engineer sits down to start on a task, especially if it’s a bug fix or something like that, there’s already a PR waiting for them.

[01:05:54] Yeah. And they just have to decide, is that how I wanna fix it- Yeah … or something else? And often they’re like, “Well, that’s 90% there. You know, here’s a little tweak. Go for it.”

[01:06:03] Dan: Yeah.

[01:06:04] Nathan: Okay. You said before we sat down that you have some hot takes. I, we, we got one of them- I

[01:06:09] Dan: spent my hot take . And the- Gemini’s a great model

[01:06:12] Gemini’s a great model. Gemini’s a great model for writing.

[01:06:14] Nathan: Okay.

[01:06:14] Dan: Yeah, great model for writing.

[01:06:15] Nathan: Yeah.

[01:06:16] Dan: People will find it to be silly that we were worried that AI would take all of our jobs and that- … humans would not be use- useful for anything anymore.

[01:06:26] Nathan: Mm.

[01:06:28] Dan: I think that would be very silly in hindsight. Not to say that it won’t change jobs or, you know- Right

[01:06:33] historically, lots of technology changes have, like, eliminated certain job roles. Uh, for example, if I was, uh, if I was an Uber driver, this is … We’ve been saying this for a long, long, long time. Right. So it’s gonna take a long time, but going in a Waymo in San Francisco, I’m like, “That thing’s pretty good.”

[01:06:49] Nathan: Yep.

[01:06:49] Dan: Um, and, uh, and I think that’s very important that it’s talked about and dealt, and dealt with, um, because it’s a big part of people’s live- livelihoods. And it feels obviously silly to me that we’re, we’re like, “Oh, yeah, only, like, three people will have jobs and everyone else will be the permanent underclass,” and like, whatever.

[01:07:10] Like, it’s just not… That’s just, uh, uh… W- We will look back at that and be like, “Oh, we were so naive. Like, those models weren’t even that good,” you know? Right. The models we have now, though, Those are so good.

[01:07:23] Nathan: Well, I think a, a fascinating thing is if you look at Andrew Carnegie’s story-

[01:07:28] Dan: Mm …

[01:07:29] Nathan: so his father was a professional weaver-

[01:07:32] Dan: Mm

[01:07:32] Nathan: in London. Mm. Or in, in England.

[01:07:34] Dan: Mm.

[01:07:35] Nathan: And, you know, like, a tradesman doing all this stuff, and then the loom gets invented and he’s out of work. And so they go from the middle class-

[01:07:43] Dan: Yep …

[01:07:43] Nathan: to, uh, quite poor. Yeah. And they end up immigrating to the United States.

[01:07:47] Dan: Mm.

[01:07:47] Nathan: And so you get someone who’s, like, at the, uh, like, gets the worst end of a technological innovation- Yeah

[01:07:53] and then says, “Cool, so I’m gonna take what I learned and I think I’ll just become, like, one of the richest men in America.” Does that work? You know? And you’re like… And so, like, often th- these disruptions and all of that- Yeah … result in some pretty crazy changes.

[01:08:06] Dan: Yeah.

[01:08:07] Nathan: All right. I love those hot takes. So final thing that I wanna ask is what are you reading?

[01:08:12] You’re someone who is on the cutting edge of everything. Mm-hmm. And then I also know that you, you’ve always loved philosophy. Mm. You’ve always loved writing and the craft of it.

[01:08:22] Dan: Yeah.

[01:08:22] Nathan: What’s, what’s the reading that’s fueling your future?

[01:08:26] Dan: I’m currently reading Wind, Sand and Stars by, um, Antoine de Saint Exupery.

[01:08:33] He’s …

[01:08:33] Nathan: Oh, yeah?

[01:08:34] Dan: Um, the Little Prince guy.

[01:08:36] Nathan: Yep.

[01:08:36] Dan: Very good. It’s his memoir.

[01:08:38] Nathan: Okay.

[01:08:39] Dan: And I think it’s, it’s about his experience being a pilot for the mail, like the- Mm … Aeropostale, like the French mail service in, in the Sahara in Africa. Um, and, um, I mean, there’s a lot, there’s a lot in it that is about-

[01:09:03] I have this, I’m in charge of delivering the mail and this new technology that people think is, uh, separating me from nature and the problems of man- Right … and actually it is plunging me into, like, nature and the problems of man. Yeah. And I think he has that, that sensibility, so I re- I really like that.

[01:09:19] Nathan: I’m gonna have to read that.

[01:09:20] Dan: It’s, it’s, it’s pretty good. It’s pretty good. Um, other than that, I’m in, like, a l- in a little bit of, like, I’m in between a couple things. I just finished Les Miserables.

[01:09:29] Nathan: Okay.

[01:09:30] Dan: Um, which I thought was actually … It was really good. I- Hugo is a little bit, um … He’s pretty over the top.

[01:09:37] Okay . And he spends, like, 40 pages, like, talking about French slang, French c- criminal slang, which to be honest, I could get on board with, and it’s a l- it’s a lot. Yeah . And I think also his, a lot of his, like, love scenes are a little … I think French, maybe just French love scenes are a- Yeah … are, are kind of a lot.

[01:09:58] But, um, but it’s, it’s, it’s quite, it’s quite a beautiful book also. Um- That’s awesome. So I try to, like, mix between philosophy, fiction, memoir, kind of-

[01:10:08] Nathan: Yep.

[01:10:09] Dan: Yeah.

[01:10:09] Nathan: All of that. Uh, I love y- your approach of being on the cutting edge of everything, and then saying, like, “Hey, let’s, let- let’s also stick to the classics.”

[01:10:16] Dan: Yeah, that’s what I’m- That’s sort of the kind of new and old thing that I was, I was trying to point to earlier, that- Yeah … they’re both very important to me.

[01:10:23] Nathan: I like that.

[01:10:24] Dan: Yeah.

[01:10:24] Nathan: Okay, if you were to recommend one article that you or the Every team have written, someone wants to dive in, if a creator listening wants to dive into-

[01:10:32] Dan: Hmm

[01:10:33] Nathan: your world, where would you start?

[01:10:34] Dan: I mean, you gotta do the Eight Levels of AI. Okay. Yeah. Um, so just search. We have a guide. Um, and you maybe put it in the, in the- Yeah, we’ll put it in the show notes … in the show, show notes. Um, and then I wrote this piece called After Automation, which is, like, why will there be really great human work to do after automation?

[01:10:51] Um, what is, what do we see for, for ourselves? And then why is that structurally true? That I think is, uh, a good thing for you if you’re, like, trying to get into the mind space of, oh, actually these tools can help me do my work better.

[01:11:05] Nathan: Yeah. I love that. Okay, so check out those two things. Go check out every.to.

[01:11:10] See everything that you’re doing. And then, uh, probably follow you on all the social channels.

[01:11:16] Dan: Definitely.

[01:11:17] Nathan: I think X is … Is that where you’re spending most of your time? That’s the

[01:11:19] Dan: big one. Yep.

[01:11:19] Nathan: Okay. Just Dan Shipper on X? @

[01:11:20] Dan: dan shipper.

[01:11:21] Nathan: Perfect.

[01:11:22] Dan: Thanks so much for coming on. Thank you.

[01:11:23] Nathan: In the episode, you heard Dan say that he writes by just talking to AI.

[01:11:28] If this is something you wanna learn more about and possibly do yourself, check out episode 101 with Jay Singh. Jay helped our team at Kit automate workflows with AI voice agents, and in that episode, he builds a working voice agent from scratch live on the show. Like the video if you enjoyed it, hit subscribe on YouTube or wherever you’re watching, and I will see you next week.

[00:00:00] Jayson: If you can’t get an invite into the room, maybe you can create the room.

[00:00:03] Nathan: Do you wanna know how to get into rooms with people who are several levels above you and have a lot more status and influence? Jason Gainer is the reason about 50 of my favorite entrepreneur friends are in my life.

[00:00:14] Jayson: An event like what we do, you can absorb an entire network within two days, really condensing a decade of networking into a couple days.

[00:00:21] Nathan: He wrote the book Community Made, which tells you exactly how by going into how to find your people.

[00:00:27] Jayson: Create a list of 10 people. The hardest one you think to convert, put them as, like, number 10 on the outreach list, and then you go after the first easiest person.

[00:00:35] Nathan: How to invest in people.

[00:00:36] Jayson: The deepest way to invest in a relationship or to start a relationship is to make people feel seen.

[00:00:40] Nathan: And then how to ask them for help.

[00:00:42] Jayson: I had nothing to offer him but support him to launch his book, and I promised him I’d do all the heavy lifting. That became a beautiful relationship. There’s a big difference between building a fan base

[00:00:51] Nathan: and building a community. And what you’ve done with MMT, you created the whole thing.

[00:00:55] You curated the group. But the magic continues even when you’re not in the room.

[00:00:59] Jayson: Doesn’t matter how many friends you can count, it matters how many friends you can count on. I’d much rather have 500 deep relationships, people who have my back, than 50,000 followers on Instagram. By the end, you’ll know how to make it into a room where you’re wondering, ”

[00:01:12] Nathan: How did I even get here?”

[00:01:13] Jayson: Or you can even buy access to find yourself in the right room, but is what keeps you in that room. Amazing.

[00:01:23] Nathan: So Jason, I’ve had the experience of hosting a lot of incredible people at my house, and I realized that most of them come back to relationships that, that I met through you. So I was watching the World Cup and with, uh, Philip McKernan and his son Charlie, and his whole family, and we were just having the best time, and I had this moment of, you know, they’re huge soccer fans, and I realized, like, oh, this is because of Jason, right?

[00:01:47] They’re coming to stay on my farm. Ben Greenfield came to stay on my f- like, all of this is because of the relationships that, that you’ve built. And so I wanna dive into how you do that, how you’ve created, you know, at this point, like, probably 50 of my entrepreneur friends are because of you. And there’s obviously a science to it, and we’ll, we’ll get to all of that.

[00:02:05] But before we do, like, I wanna talk about the, the early side of relationships for you. Like, were you always this business relationships super connector? I actually know that you weren’t. So

[00:02:15] Jayson: when you- Well, if you read the book, you’ll realize very much- … uh, I wasn’t. No, I, I, I wasn’t, uh, that relationally focused.

[00:02:22] And in fact, when building my first business, I did it at the expense of relationships, not burning those relationships per se, but I just didn’t invest any time. And for me, I ended up with a very successful business. Um, but when I got married, I had two people at my bachelor party. I had my brother and my brother-in-law.

[00:02:39] Oof. The entire wedding party could fit in this room right now. Um, so it was clear that I was playing the wrong game. And as I transitioned out of that business, which ultimately I discovered I built a business I hated to enable me to buy things I didn’t need to impress people I didn’t like, I just felt very much out of alignment and I had to find something else.

[00:02:57] And the first thing I was trying to cure was this sense of loneliness that I had. Um, and I was inspired by Seth Godin. I had an opportunity to go to a workshop that he was putting on. And I’ve always been a b- big fan of Seth’s work, but never had an opportunity to kinda see him live in person. And it turns out the theme of it was the connection economy and how there’s huge value connecting like-minded individuals.

[00:03:19] So for me, I saw that as a source of inspiration and I planned something I called Mastermind Dinner, which was, uh, an evening geared towards bringing eight entrepreneurs together for dinner. Um, and I had… Because I had no network, I went through a magazine list of like some of the top entrepreneurs locally and I said, “Hey, I’m doing a dinner for entrepreneurs of this magazine if you wanna join.”

[00:03:42] I probably had a 5% response rate at best, but eventually I had my eight guests. On the first dinner I did, I was incredibly nervous. Um, I didn’t think I could keep my food down. I didn’t know how I was gonna facilitate this. I didn’t know how conversation was going to, to keep throughout the dinner, but conversation didn’t skip a beat for four and a half hours and I just got clarity that being in proximity of people like that was something I wanted to do to some capacity for the rest of my life.

[00:04:06] And that was first dinners, then became MMT, uh, and then I became very, very relationally focused from that point forward. But no, it was not always like that.

[00:04:14] Nathan: Yeah, so you have this line in the book. I’m gonna find it. “Never beg for a seat when you can build your own table.”

[00:04:19] Jayson: Mm-hmm.

[00:04:20] Nathan: There’s an experience that I think a lot of us have had where you see an event happening, especially ’cause now it’s on everybody’s Instagram stories and there’s reels about it and whatever else, and you realize like, “Oh, all the people.

[00:04:31] Like that person’s there? Are that… Like I want to be there.” And you haven’t done anything yet, you know? Or, or you didn’t get an invite and so you feel some amount of like jealousy, loneliness, uh, you know, and, or you’re like, “Am I worthy?” What do you do with that feeling when you have it and you say, “Oh I didn’t get the invite, what can I do instead?

[00:04:52] Jayson: Yeah, I mean, I, I, the, the premise behind that quote was, I remember having a conversation with a friend of mine, um, and I don’t know who the original source of this was, but he was struggling to get picked to speak at events. And I said, “Instead of trying to be in a position where you’re picked by other people- Mm

[00:05:09] why don’t you build your own stage?” Um, and this is a similar kind of philosophy is if you can’t get an invite into the room, maybe you can create the room.

[00:05:17] Nathan: Right.

[00:05:18] Jayson: And it’s actually a lot easier than people realize because there is a desire and appetite for people to connect and to have a space. Mm. Um, however, it’s a lot of work, uh, to put it together.

[00:05:29] So if you’re willing to put in that effort and that energy, um, then you can ultimately be the catalyst that brings these people together, and there’s, there’s a lot of, of, of value in that, not only being a fly on the wall of these conversations and hosting people, but, uh, David Buss, who’s, um, evolutionary psychologist, talks about, uh, how from an evolution perspective, there’s a level of status bestowed upon whoever commands the most focal point throughout a gathering.

[00:05:57] So if you’re a speaker on a stage and it’s your event, you’re getting most of, of that focal point. And as a result, everybody in the room naturally puts you, um, on a- Higher status … a higher status. Yeah. So that, that’s something I wasn’t aware of when I was starting to do events and that kind of stuff, but that turned out to be a big kind of ancillary benefit.

[00:06:14] And there’s a lot of different e- examples of people who’ve done exactly that, who didn’t necessarily have a network, but had, uh, an interest in a certain- Uh, area or industry and just started bringing people together. Now, an event is the extreme. Right. There’s so many things you can do in advance of that, um, that are a lot lower lift.

[00:06:32] Whether it’s Nick Gray is world-class at his two-hour cocktail mixers. Yes. If you wanna go a step above that, it could be, uh, dinners like I was doing, which are, again, relatively low lift. Uh, and then eventually you can work into something like, uh, what we’ve done with, with MMT would be at the extreme.

[00:06:49] Even the… I don’t know if you’re familiar with the guys from Summit Series?

[00:06:51] Nathan: Yeah.

[00:06:52] Jayson: They have a beautiful, simple origin story. Summit Series is, like, enormous. They do Summit at Sea where they book out a cruise ship every year. It sells out every year. They bought a mountain in Utah, which is, like, one of the largest ski resorts in, in North America.

[00:07:06] Um, they, so when people see them from the outset, and, like, the type of people that go to their events, they’re like, “Wow.” Like, you know, they don’t understand the humble beginnings. Right. But how Summit Ser- Series started was it was just a bunch of young guys that, uh, again, wanted to be found in these circles, so they started with a ski trip.

[00:07:24] So they invited, like, 40 people in tech, and it was, like, Travis from Uber and s- uh, but this was pre-Uber. Early, yeah. Yeah, exactly. And, and which just leans into the philosophy of amazing people becoming increasingly amo- amazing over time. So if you can spot those diamonds in the rough, there’s huge value in that.

[00:07:40] And the one thing that the Summit Series guys did is they had got sponsors. They’re like, “Hey,” after they got the 40 people to opt in for this ski trip, um, then they went to Staples and a couple different sponsors and said, “Hey, would you like to sponsor this?” So they got the whole trip paid for, and they were the catalyst that brought it together.

[00:07:56] Fast forward 15 years, I mean, it’s amazing obviously what Summit Series has, has achieved. So, uh, it’s a playbook that a lot of people have used really effectively.

[00:08:04] Nathan: Yeah, I was thinking about, like, this idea of organizing the room.

[00:08:07] Jayson: Mm-hmm.

[00:08:08] Nathan: So to, to get into a room that you wouldn’t normally belong in. Yeah.

[00:08:12] And so that dinner, you know, in this case, you’re not in the magazine that you’re sourcing people from.

[00:08:17] Jayson: Yeah.

[00:08:18] Nathan: But it gets to a point, like, the first person might be like, “What is this event that I’m saying yes to?”

[00:08:22] Jayson: Yeah.

[00:08:22] Nathan: But once you have two or three, they’re like, “Oh, that person’s going? I’ve always wanted to meet them.”

[00:08:27] You know, we might live in the same town, but we’ve never connected- Yeah … and so you’re creating that. And even the experience that you describe in the book of, like, taking a step back at the dinner and realizing like, oh, it… Like, just curating the group- Mm-hmm … got us, what? 50% of the way there? Yeah. 80% of the way there.

[00:08:41] Yeah. You know? And then it didn’t even have to be are you famous, well-respected, or whatever else. It was like, are you willing to do the work to get the people in the room?

[00:08:49] Jayson: Yeah, and I, I think that’s, um, a challenge that most would encounter early on is, like, how do I get the first couple people?

[00:08:54] Nathan: Yeah.

[00:08:55] Jayson: Um, and I think there’s, there’s two different approaches you can take.

[00:08:57] The first is if you, let’s say you create a list of, of 10 people. The hardest one you think to convert or to, uh, to get to agree to your dinner, let’s say. Uh, you put them as, like, number 10 on- Right … the outreach list, and then you go after the first easiest person. And after you get them, you go after the second person, the third person.

[00:09:14] You build this momentum. By the time you get to the 10th person, you can be like, “Hey, I got these nine other people that are fascinating in their own right.” Uh, and it, it’s … They’re gonna be much more likely to, you know- Yeah … agree as a result.

[00:09:25] Nathan: Your conversion rate is li- likely to increase with

[00:09:28] Jayson: every

[00:09:28] Nathan: yes.

[00:09:28] Jayson: Yeah, exactly. The other philosophy, there’s a, a principle in real estate called, uh, an anchor tenant. So if you have a mall that is just, like, flailing and is not getting any traction, you know if you get a Neiman Marcus or an Apple- Mm … that can completely change, like, just the, the appeal of other tenants to, to wanna kinda, uh, sign leases as well.

[00:09:52] So that is kinda what I did, uh, with the kickoff of MMT. I didn’t have a network at all, but I did have a relationship with Tim Ferriss. Mm-hmm. And when I got Tim to commit, it made it much easier for me to reach out to other people-

[00:10:04] Nathan: Right …

[00:10:05] Jayson: who were either friends with Tim that never find themselves at the same, uh, at the same time, same place.

[00:10:10] So as a result, the event could be a catalyst to reconnect him with all his close friends, and I could also reach out to people who’d wanna be connected to Tim, uh, to speak for the event, and that kinda stuff. So, uh, that is the principle I used for, uh, to effectively kinda launch MMT, but both of those, um, kinda frameworks work for sure.

[00:10:27] Nathan: I’ve done that with some of these masterminds that we’ve hosted. Like, we have an author mastermind.

[00:10:32] Jayson: Yeah.

[00:10:32] Nathan: You know, and the relationship in that space that I have is with James Clear. Yeah. We’re, we’ve been good friends for, I don’t know, 14 years now, and he’s building a publishing company. I’m building an email company serving authors.

[00:10:43] And so we’re like, “Wait, we’re trying to reach the same group. Let’s just team up.” Yeah. Yeah. And our hit rate for people who say yes to that event is just insanely high because our anchor tenant is the guy who sold 30 million copies.

[00:10:56] Jayson: Dude, I will say, getting back to what you said at the beginning of this episode, when I saw photos of, like-

[00:11:01] your first mastermind and some of the people there, I was like, “Man, what can I do to get in that room?” Um- Well, you’re

[00:11:06] Nathan: coming to

[00:11:06] Jayson: that one in like four weeks … I, I feel so, I feel so grateful. So. I don’t wanna, like, yeah, I don’t wanna jinx it. But, um, 100%, that’s a- another strategy as well, um, that I forgot about, is the act of partnering with somebody.

[00:11:20] Mm-hmm. Again, putting on these experiences can be a lot of work, and years ago, two good friends of mine, Michael Fishman and a guy named Ramit Sethi, who’s actually the more popular of the two, especially now, um, they partnered on hosting a dinner in New York once a month for years. Mm-hmm. Uh, and they had six people.

[00:11:36] Michael would invite three people. Mm. Some, uh, Ramit would invite three people, and they would do the dinner. And at the end of the year, they would do a closing party for the year, invite all the dinner guests- Right. Oh … for the dinner. And, uh, I don’t know the dynamic.

[00:11:50] Nathan: Mm-hmm.

[00:11:51] Jayson: If the dinner were to happen now, again, Ramit is, like, more of the draw, uh, and Michael would be doing a lot more of the, like, the orchestration and the heavy lifting.

[00:11:58] Um, but the partnering is actually a, a brilliant philosophy, uh, as well. And there’s even people I know that, um, are big name individuals, lots r- lots of reach and great networks, and that kinda stuff, who wanna bring people together, um, but don’t have the bandwidth to do so. Right. So if you’re willing to be the person who’s willing to do that heavy lifting, uh, it can be a fantastic win-win.

[00:12:21] Nathan: Yeah, I love that. You know-

[00:12:23] Jayson: I gotta put that in the book. That was smart. Gosh, we should’ve done this interview six months ago.

[00:12:27] Nathan: Yeah, exactly. Well, I have an advance reader copy. You have the finished one, but you’re still marking up the finished one.

[00:12:32] Jayson: It will forever be, yeah. Yeah. It’s never gonna stop.

[00:12:34] Nathan: That’s how it goes.

[00:12:35] You know, along those lines of being the one to curate the group- A strategy that I do is I love playing, like, city league sports.

[00:12:42] Jayson: Mm.

[00:12:42] Nathan: So volleyball and soccer.

[00:12:43] Jayson: Yeah.

[00:12:44] Nathan: And I, I didn’t play sports growing up, and so I want to play at a level that’s far beyond what I would get invited to play at. But no one wants to run the teams, you know, and be sending out texts of like, “Hey, you know, there’s a 9:00 PM game on Wednesday.

[00:12:58] You gonna be there?” You know? Yeah. And so if you’re just the one to facilitate the group … Like, on my volleyball team, more than half of the team, like, played in college at a very high level. Like, one player is a NCAA Hall of Fame player. Like, all of this, right? And I love playing at that … ’cause they just make me so much better, but I, I have no business being on that team except for the fact that I organize it, and they’re all so grateful that I put together the team.

[00:13:21] And they’re like, “Thank you so much for inviting me to this.” And I was like, “You played on ESPN.” Like … And but it, it’s like putting the room together, and the same experience, right? So you introduced me to Will Guidara. He’s, uh, been on the podcast, and he came to our author mastermind. And I had two different experiences with him.

[00:13:39] One was we’re, we’re at this, like, really fancy hotel, like, farm resort outside of, uh, Nashville, and watching the hotel staff absolutely lose their minds that Will Guidara was at, staying at their hotel. They’re just like- … “You wrote the book,” you know, all that. So that was one experience. Yeah. And the other experience was Will being like, “Man, thank you so much for inviting me.

[00:14:02] This was amazing.” You know, and we’re like- Thank you so much for coming.

[00:14:05] Jayson: Yeah.

[00:14:06] Nathan: But, but he was so grateful to be in the room with people that he could learn from and, and, and all of that. And so being the person to put it, to put together the, the room is like a huge gift.

[00:14:15] Jayson: Yeah, and I mean, I, I experienced that with you at MMT- Yeah

[00:14:18] to some degree. I mean, it, it’s, it’s very much people come up to me afterwards with, like, appreciation. Mm-hmm. And I was like, “This would not work if you were not here.” You know what I mean? Like, you… The, the magic of this i- I mean, a room is simply four walls. Mm-hmm. Right? So the magic is the people in it.

[00:14:33] And yes, there’s an element of, like, curation and all the work that goes into it, but the magic is, is truly the people who, who, who show up. So, um, yeah, it becomes this just beautiful kinda reciprocal thing. But there’s, there’s the, the one way of building your own table, and then there’s the other way of potentially buying access.

[00:14:51] Yeah. Whether that’s finding yourself in the right rooms, going to, into the right events. And those experiences can really deliver on one of the most valuable assets for folks, which is speed. Mm-hmm. Uh, the speed of relationships specifically. Because if somebody comes to an event like what we do, anything that’s highly curated specifically, you can absorb an entire network within two days.

[00:15:12] Right. Really condensing a decade of networking into a couple days. So, um, there’s many ways to the mountaintop. Um, I started again doing the dinners and all that kinda stuff, which evolved into kinda MMT. And now thankfully, I’m, I’m starting to finally after all these years get in- invited into the right room, so.

[00:15:29] Nathan: Hey, just a quick note before we keep going. If you usually just catch episodes whenever they pop up in your feed, take a second to hit subscribe or follow. We’ve got some great conversations coming

[00:15:39] Jayson: up, and that’s the easiest way to make sure you don’t miss them. Thanks so much for your support.

[00:15:43] Nathan: Well, you have this section in the book here.

[00:15:45] I was… I love the il- the illustrations in here. But, um, you know, you’re talking about three ways of getting access.

[00:15:53] Jayson: Mm-hmm.

[00:15:54] Nathan: And that’s money, moxie, and service.

[00:15:56] Jayson: Mm-hmm.

[00:15:56] Nathan: So break those down.

[00:15:58] Jayson: The story I share in the book pertaining to money is a good friend of ours, uh, Andrew Wilkinson. And he’s famous for many reasons, uh, but he is the co-founder of Tiny, which is ultimately a, a holdco of wonderful internet companies.

[00:16:14] They own AeroPress and Letterbox and a slew of, uh, just again, great businesses. And it was probably about five years ago now, he- won a charity auction to have lunch with Bill Ackman. Mm. It was $57,000, which a lot of people thought was insane at the time. Um, and he had the, uh, the lunch with Bill and his partner Chris at a restaurant called Marea in New York, and they were just peppering Bill with so many questions about Starbucks stock or parenting, um, and they were just so insatiably curious, and fascinating in their own right, which was important.

[00:16:52] And I share that because Bill actually enjoyed the conversation so much, he’s like, “I would’ve done that for free,” and invited both Chris and Andrew to their offices after the fact to meet his team and all that kind of stuff. And fast-forward about a year later, Bill became the biggest investor in WeCommerce at the time.

[00:17:09] It was, I think it was a $40 million investment- Mm-hmm … and helped take the company public. Um, so the ROI from that one dinner, uh, of that $57,000, which again, a lot of people thought was- Right … was, was wild, um, was pretty significant. So that is one way, is you can buy access. I shared a story with you offline of one of the things that set me on a completely different tr- trajectory was attending an event that was $10,000 to go- Mm

[00:17:34] um, that Tim Ferriss put on. I had no, uh, no right to be in that room. But, uh, I courageously cut that check, and that, yeah, that event completely set me on a whole new trajectory. So, um, that is one way to kinda build a network, is being willing to invest capital, uh, and to get access to those rooms. The other one is moxie.

[00:17:58] Uh, the other story I share pertaining to Andrew ironically as well, is well before he was minted a billionaire He, and he still does this to this day, which I admire him so much for, he would send emails to people cold all the time. Um, so when he was starting Metalab, he would find companies on TechCrunch that had just raised money, and would send them real- like, a simple email saying, “Hey, I just saw you guys raised money.

[00:18:21] We should work together.” Like, that was the essence- Yeah … of the email. Um, and that led to, like, some really big clientele. So he’s just super-

[00:18:27] Nathan: Well, like Metalab designed the first version of Slack, as an example.

[00:18:31] Jayson: Y- yeah.

[00:18:31] Nathan: Like, right so if you, to give you an idea of the caliber of people that they

[00:18:34] Jayson: ended up working with.

[00:18:34] What it’s grown to over time- Yeah … for sure. Um, but, like, he was just religious with, like, cold outreach. And he stumbled across Dan Gilbert’s, uh, story, and ended up emailing him at, like, 2:00 AM one day just saying, like, “Hey, I think what you’re doing is fascinating, uh, in Detroit.” So Dan Gilbert is the, uh, founder of Quicken Loans.

[00:18:53] Nathan: Yep.

[00:18:54] Jayson: Um- Rocket

[00:18:54] Nathan: Mortgage,

[00:18:55] Jayson: all of that. Yeah. Yep. And it’s worth a couple billion dollars, and, like, invested I think, like, 5 billion or something like that into, like, Detroit.

[00:19:00] Nathan: Yeah, he’s trying, he’s trying to reinvigorate downtown Detroit-

[00:19:04] Jayson: Yeah … like,

[00:19:04] Nathan: single-handedly.

[00:19:05] Jayson: And that really inspired Andrew. On some small level, he’s trying to do that with Victoria, where he’s based out of, and he was just fascinated by that, so he sent him a cold email.

[00:19:14] And he said within, like, 15 minutes, this was, again, in the middle of the night, um, Dan replied, “Yeah, I’d love to meet up.” And so he invited him to Detroit, and it was, again, Andrew and his business partner, Chris. They spent the full day with him in Detroit. Again, he met his team and all that kind of stuff, and that was just from a, a simple email.

[00:19:30] So not everybody has $57,000- Right … to buy access, but everybody has access to email. And in conversation with Andrew last week, I mean, it… He he has so many wild stories. He emailed, cold emailed Mark Zuckerberg, like seven, eight years ago. Um, I don’t know if I should share this story- … but we’ll keep it in.

[00:19:47] Yeah. I’m sure he’ll be okay with it. He e- cold emailed him, ’cause he was going to Vancouver or something like that, and, uh, Victoria, where Andrew lives, is a th- 30-minute flight. And didn’t think anything of it. Never heard a response until the night before. And, uh, Mark’s like, “Yeah.” Well, he asked him to, if he want to do dinner.

[00:20:03] It was like a super quick cold email, asked Mark Zuckerberg, “Do you wanna do dinner?” And the night before, uh, Mark said, “Yeah, sure, let’s do it.” And then the funny thing is, uh, this is why Andrew’s legendary, he, um, he, he couldn’t get off the island to go to… He couldn’t catch a flight. There was no flights to catch.

[00:20:22] He couldn’t get a ferry. He was trying to see if he could rent some rich guy’s boat- Yeah … to, like, carry him over. So he actually, then he emailed Mark. He’s like, “I can’t actually do dinner.” Oh, sorry. So he’s, like, the only person who’s ever stood up Mark Zuckerberg. But the amount of doors that have opened- Right

[00:20:35] as a result of his cold outreach is wild, and it’s still something he practices to this day. So if you can’t cut a big check, then, then cold outreach is a, is a great option as well. And then the final one is-

[00:20:45] Nathan: Well, before we get into that, like the- Yeah … I mean, I love the idea of moxie, because it’s something that As a, like, really shy teenager- Yeah

[00:20:53] I would not talk to anybody. Yeah. And I remember actually the first, like, real conference I went to was an event, it was called An Event Apart, and, uh, it was a web design conference. Mm. So all of the, like, biggest founding names in the web standards movement and, like, web design, um, were all speaking there, and this was everyone that I had learned from.

[00:21:11] I’d read all their blogs and all of that. And I went to that conference. I’m like, “Oh, man, I’m gonna be in the room with all these people.” And I met two people the entire time, and they were both people that I sat next to at, like, a meal or something- Yeah … who introduced themselves to me, ’cause I was so shy.

[00:21:25] And I had this experience of walking from the, the venue back to the hotel on the Seattle waterfront and realizing that all the speakers were walking, like, 100 feet in front of me. I’m like, “Wait, th- these are the people who I’ve learned everything from.” And so I, like, sped up a little. Like, I walked a little faster so I’m, “I’m gonna join their conversation.

[00:21:43] Like, this is gonna be amazing.” And then I, like, got to maybe 15 feet away and totally chickened out- … and, like, slowed down again. And then I was like, “I can do this. Okay, let’s go.” And did it again. And then went, “Yeah, no.” And so it’s, like, this accordion, like… And that, they were probably like, “What’s this guy’s deal?”

[00:22:01] But then they turned, and I realized that they were staying at the same hotel I am.

[00:22:04] Jayson: Mm.

[00:22:05] Nathan: And I had dropped back a little because I was like, “I gotta get the scourge.” And they walked into, um, the hotel, and they turned to go to the lobby, and like the little restaurant and bar area there, and they all sit down.

[00:22:17] And I was like, “Okay, here’s another opportunity that I can join. It’s a more casual setting than acc- accosting them on the on the street.” And I just kept walking and went straight to my room and didn’t, because I couldn’t get up the moxie to- Yeah … uh, to say hi to them.

[00:22:30] Jayson: Well, I appreciate that transparency, ’cause I think people look at folks like you and I, that we can just walk into a room and like own the room.

[00:22:36] Nathan: Yeah.

[00:22:36] Jayson: To this day, I still have to like psych myself up. Uh, I have so many stories of like being in the hotel, my hotel, like, uh, room- Mm-hmm … in the washroom, looking in the mirror, trying to psych myself up to go downstairs for a cocktail mixer. Right. So it’s, uh, it’s important, but there is also… And at the…

[00:22:55] It is good to see other people who are bold. Mm-hmm. How those moments of boldness can compound into incredible- Right … things over time. But one of the things that has always helped me is this philosophy that like eight, eight seconds of courage can change your life. Right. And I learned this through skydiving.

[00:23:11] I’m terrified of heights. Uh, so I thought the best way to overcome being terrified of heights is to hop out of a plane at 10,000 feet. Yeah. Didn’t work. But regardless, were you… Have you gone skydiving before? I have. So you’re going up in like circles, and- And

[00:23:23] Nathan: it’s a little plane. It takes forever to get up there.

[00:23:25] Oh, it’s brutal.

[00:23:25] Jayson: Uh, so you’re there, and you’re like, “Oh, this is taking forever.” And, uh, then the door flings open, and then it feels like you’re getting sucked out of the plane, and it’s loud. And I remember I was just like frozen. I remember telling myself, “Eight seconds of courage will change your life. All I have to do is get out of this plane, and then, like, whatever happens, happens.

[00:23:40] If I die, I die.” “But like, I just need eight seconds of courage.” And that has served me well. If I need to step on stage and I don’t feel comfortable delivering a talk, uh, in social situations, again, like you’re just breaking into a conversation, and then once you’re there, you’ll, you’ll have to figure it out most likely.

[00:23:56] Um, so yeah, just appreciate that, that, that share and the eight- Yeah … seconds of courage framing has been helpful for me.

[00:24:02] Nathan: There’s another version of it that has been helpful for me. I, I try to contrast… Like if I’m i- uh, talking to someone, especially someone famous, I don’t wanna be the… Like I don’t wanna be a burden on them, I don’t wanna intrude and all this, but I really wanna meet them.

[00:24:14] And so the thing that I always think about is two types of energy to bring to a conversation. There’s lingering energy, and there’s leaving energy.

[00:24:21] Jayson: Mm-hmm.

[00:24:22] Nathan: And so I just always try to bring leaving energy. So if I come up, you’re talking to your friends, and I’m like, “Hey, I, sorry to interrupt,” you know, all this, and then I’m like, “It’s so great to meet you.

[00:24:30] I’m a big fan.” And I’m like They’re like, this is lingering energy and it’s awkward, and then they might be like, “Okay,” like they might wanna end the conversation. And that’s not the feeling I wanna leave anyone with, and that idea is going to put me in a place where I’m like, “Well, I don’t even wanna have the interaction to start with.”

[00:24:46] Jayson: Yeah.

[00:24:47] Nathan: So what I started doing is what I call leaving energy. So the first time that I did this was actually Chris Brogan had given a talk at Social Media Marketing World, and afterwards everybody lined up.

[00:24:59] Jayson: Yeah.

[00:25:00] Nathan: And we’d exchanged emails before. This is in like 2016 or something. Yeah. And so, like I had a, a bit of an online presence and all that, but I wasn’t a speaker, I wasn’t any of those, those things.

[00:25:10] And I w- walked pa- You know, there’s 20 people lined up to talk to him, and I walked past the entire line and said, “Hey, Chris, great talk. I’m Nathan Barry. We emailed earlier. Um, just, uh, wanna say that was fantastic. Would love to ca- catch up later at the closing party.”

[00:25:23] Jayson: Mm. ”

[00:25:24] Nathan: I’ll catch you later.” And then walked away with leaving energy.

[00:25:26] And so it was a 45-second interaction, and it … I don’t know, I don’t know if this is arrogant or what, but I gave him … I was like, “You know, you’ve got … You got your fans, all of that.” Yeah. “I’ll catch you when, you know-”

[00:25:37] Jayson: Yeah. “…

[00:25:37] Nathan: you’re not doing your thing.”

[00:25:38] Jayson: That feels like some Neil Strauss.

[00:25:41] Nathan: And so what happens is it takes all the pressure off.

[00:25:44] Jayson: Yeah.

[00:25:44] Nathan: Because if I am wasting someone’s time, okay, I wasted 45 seconds of their time. And then I actually did this at, um … I was at the Cannes Lions Festival earlier this year.

[00:25:54] Jayson: Mm-hmm.

[00:25:54] Nathan: And so it was like all the biggest marketers and creators and all of this. And Steven Bartlett is about to go on stage, and I’m there for his talk.

[00:26:02] Um, I know some people on his team, but I’ve never met him- Yeah … all that. And I realize that from where I’m sitting, it’s like this outdoor stage He’s sitting across the stage, like, kinda, kinda half backstage and all that, talking to someone. I don’t know if it’s someone that he’s never met before, I don’t know if it’s t- his team member or whatever.

[00:26:18] I’m like, “Oh, this is the perfect opportunity. He’s not going on for another six minutes. I should go say hi,” but there’s, like, tons of people in the way. And I realize I can actually, like, walk backstage easily and around the stage and get to him. And so I did that, and I got up, walked over, and I was like, “Hey, Steven, my name’s Nathan.

[00:26:32] I run a company called Kit. You guys have actually used us for some of your…” And he’s like, “Oh, I know Kit. Like, that’s great.” And we talked for, like, a minute, and then I was like, “All right, I’m gonna go.”

[00:26:40] Jayson: Mm-hmm.

[00:26:41] Nathan: And, you know, I knew he was both captive and he knew that I knew he had to g- you know, it was super quick.

[00:26:47] And then he ended up following me on X a week later. Oh, wow. And then, uh, after that… And I was like, “That’s random. Okay.”

[00:26:53] Jayson: Yeah.

[00:26:53] Nathan: And then we ended up having a, like, an hour-long call on WhatsApp at 11:00 PM. Oh, wow, dude. ‘Cause he was like, “I wanna dive into the email world and-

[00:26:59] Jayson: Yeah …

[00:26:59] Nathan: and all of this, this stuff.”

[00:27:00] And it’s just that idea of, okay, leaving energy, ei- eight seconds of courage, like, let’s just make this happen.

[00:27:06] Jayson: Yeah. No, it, it’s such a, a beautiful story that you share because it, it… That’s how relationships are formed. Mm-hmm. And the, one of the challenges a lot of folks have when meeting somebody is they put them on a pedestal.

[00:27:17] Nathan: Mm-hmm.

[00:27:17] Jayson: And when you put somebody on a pedestal, unconsciously you’re almost articulating that you’re not on the same level.

[00:27:23] Nathan: Yeah.

[00:27:23] Jayson: So when you do have that, like, cool approach with what, what you did with Chris Brogan of just, like, a quick hello and, like, “We’ll, we’ll cross paths,” even if you don’t- Mm … if you see Chris a year from now or two years from now, there’ll be many touch points you’ll have.

[00:27:36] Yeah. I have, I have had the same, a similar experience with a lot of other people. Um, and for me, it’s almost like I look at it through the lens of, like, I just wanna plant the seed of the relationship and look at it through a long-term lens that, like, most likely we’ll cross paths in two, three years. And they know I’ve never put them on a pedestal.

[00:27:50] Right. Uh, which is I think really, really important.

[00:27:53] Nathan: Well, I think it’s also an abundance mindset versus a scarcity mindset. Mm. The scarcity mindset is, “This is my one shot- Yeah … to convince Tim Ferriss, whoever el- ” Like, this is In two minutes, I’ve gotta pack everything in and all that, and you’re like, that brings off, like, not an energy that people wanna hang out.

[00:28:11] Jayson: Yeah.

[00:28:11] Nathan: But the abundance mindset is like, oh, we’re gonna be in rooms together. I don’t need to make a whole big campfire right now. Yeah. I just need to plant a seed, have a spark, any of those things. Because, like, look, you and I are the kind of people that are gonna cross paths in the future.

[00:28:26] Jayson: Mm-hmm.

[00:28:27] Nathan: But I just need y- I need to have that first interaction now.

[00:28:29] Jayson: 100%, yeah. And I mean, just go one step further. Just if you embrace a little empathy and put yourself in their shoes- Mm-hmm … you gotta think, 98% of the interactions they have, people want something from them.

[00:28:39] Nathan: Right.

[00:28:39] Jayson: Whether it’s a photo, investment, whatever the case may be, if you don’t bring that inter- that energy to the first interaction or first couple interactions, you know, they let their, their guard down.

[00:28:48] Um, and as a result, it gives you an opportunity to actually forge-

[00:28:51] Nathan: Mm-hmm …

[00:28:52] Jayson: a proper relationship as opposed to this, like, weird dynamic of like you’re a super fan or whatever- Yeah … the case may be, so.

[00:28:57] Nathan: And I would say almost every time I’ve done that at a conference, the opportunity to have a real conversation has come within the next 48 hours.

[00:29:05] Jayson: Yeah.

[00:29:05] Nathan: Because you will cross… You know, there’s only 200, 500 pe- people at the event, and, like, you will cross paths again. And you’ll, you’ll catch, you’ll see them at a time when they are leaving a conversation or walking to a room, and you’re like, “Do I know anyone?” And they’re like, “Oh, I know you.”

[00:29:18] Jayson: Yeah.

[00:29:18] Nathan: I know you from 30 seconds from yesterday, but-

[00:29:21] Jayson: Yeah.

[00:29:21] I me- I mean, for what it’s worth, I just attended at, an event recently, and one of the strategies I have, um, is like to plant as many seeds as I can. Mm-hmm. So I’ll introduce myself to somebody really quickly, and then, like, if maybe won’t have space for a deep conversation, but that serves as a great jump-off point- Mm

[00:29:37] for a follow-up after the event. Um, which can then, you know, lead to- Yeah … a f- you know, call or just again, a bigger planting of the seed. So you’re good at this stuff, I will say.

[00:29:47] Nathan: Learned from the best. So of those three, we, you know, uh, we covered money and moxie, and the last one we, we have talked about, which is service.

[00:29:54] Is there anything else on service that, um, we haven’t covered that, like, is a

[00:29:58] Jayson: good way to do service? Yeah, so service is actually the act of really supporting somebody, oftentimes through the lens of- Of donating your time, apprenticing, that kind of stuff. I think apprenticeship is a lost art. Um, and somebody who I think has done that exceptionally well and navigated that really well is Ryan Holiday.

[00:30:17] Um, he was effectively a college dropout, uh, and then started working with Tucker Max to support him with, uh, his book launch, and, uh, then was introduced to Robert Greene and became his research assistant, and did a lot of, like, tasks that Robert Greene didn’t wanna do. Um, and did it with a smile and did the best work he could, and that blossomed into a beautiful kind of relationship.

[00:30:41] But then when it was time for Ryan to do a book, then he had Robert Greene’s, you know, support. Um, and as Robert Greene’s, like, stock has kind of continued to climb in the world, as has Ryan, and even some would say, you know, Ryan has almost eclipsed him to, to some degree. But, uh, one of the beautiful things about Ryan is he always holds Robert in such h- high regard- Mm-hmm

[00:31:01] as, like, a mentor and always kind of looks at him through that, that lens. But I share that because it’s a great opportunity, um, to reach out to people. I mean, you, you, you probably get this all the time too, though, like, people who reach out to you and like, “Hey, I wanna volunteer or help,” or whatever the case may be, and they almost put the onus on you to come up with ways that they can be helpful.

[00:31:20] Right. Uh- Mm-hmm … and I remember there’s a story about Warren Buffett and Benjamin Graham. I think it’s part of the book. Yeah. It’s a brilliant story, uh, where Warren Buffett, uh, wanted to work with Benjamin Graham, who was, uh, his professor at the time and had, um, his own investment kind of arm. And he’s like, “I’ll volunteer for you.

[00:31:37] I’ll do whatever you want.” And Benjamin, um- ”

[00:31:39] Nathan: I’ll work for free.”

[00:31:40] Jayson: Yeah, he’s like, “I’ll work for free.” And he’s like, “It’s not free to me because, like, I have to take you on, I have to train you,” and all those kind of things. And Warren was persistent and eventually ended up kind of working with Benjamin. But I think that’s the, the thing that a lot of people forget, which is even, like, the notion of almost, uh, gospel around relationships that you should ask people, like, “How can I help you?”

[00:31:58] Nathan: Mm-hmm.

[00:31:58] Jayson: And to me, I think that’s incredibly pro- problematic, um, because you’re putting the onus on the other person to come up with, with ways that you can be helpful, and they don’t have full inventory of your experiences, your expertise, uh, all that kind of stuff. So coming from a place of service, if you are going to reach out to somebody, uh, again, it’s a fantastic way to forge relationships.

[00:32:18] Actually, that’s how I forged a relationship with a guy named Shep Gordon. Oh, yeah. I had nothing to offer him but support him to launch his book. Mm-hmm. Uh, and I promised him I’d do all the heavy lifting, and, uh, that became a beautiful kind of relationship. But I reached out to him cold and said, “Hey, I know you’re coming out with a book.

[00:32:33] I know what your goals are. Um, I know what it takes to, to hit New York Times if that’s your, your, you know, in focus for you. Uh, and I’m willing to do the work if it speaks to you, and I’ll fly to Maui and we’ll see if there’s synergy.” And yeah, the rest is kind of history. So, uh, so money, moxie, and service are three great ways to, uh, tap into a great network.

[00:32:52] Nathan: Well… Yeah, I wanna focus on this idea of- Well, the, the line specifically that, uh, Benjamin Graham said to Warren Buffett- Yeah. Warren’s like, “I’ll work for you for free,” and all that, and Benjamin Graham says, “You’re overpriced.”

[00:33:04] Jayson: That’s the line, yeah. Oh, you’re over. Good, good memory.

[00:33:07] Nathan: It’s in the book. Um, but and I just think that’s so important ’cause it was like how could free be overpriced?

[00:33:12] And so- Yeah … because you have to put in this work. And so pe- when someone says, like, “You know, Jason, I’ll help you with anything,” like, “What do you need?” And all that. The response that I wanna have is like, “First, I need you to use your eyes, and then I need you to use your brain.”

[00:33:22] Jayson: Mm-hmm.

[00:33:23] Nathan: Like, look around. So in this case, if I was like, “Okay, Jason, I really wanna connect with you, and I wanna do it through service.

[00:33:27] Of these options that I’ve chosen, you know, I’m not going… I could apply for MMT, but, like, maybe I don’t have the money, and I don’t have the reputation. Like, I’m not gonna get past the curation process yet,” uh, and all of that. So it’s like, “Okay, what do you need?” So, so somebody might say, “Oh, I’ll volunteer at MMT.”

[00:33:43] And it’s like, well, there’s actually a lot of volunteers already. Like, that’s pretty well set. But if you use your eyes and you really look around, it’s like, okay, what does Jason need right now? Well, he’s coming out with a book, and so he needs to sell copies. He needs to get in front of the right rooms.

[00:33:55] There’s even, like, he needs reviews , you know, on Goodreads and Amazon and all of that. And so you’re like, “Okay, can I lead your street team?” Like a very specific thing. “Can I lead your street team for the book where I, my whole job, my KPI- You’re getting

[00:34:09] Jayson: me excited. I’m like, “Of, of course you can, Nathan.” Yeah,

[00:34:11] Nathan: exactly.

[00:34:11] Jayson: Please, this is gonna be great. Fantastic.

[00:34:13] Nathan: But my whole KPI would be like, “Okay, over the next, uh, 30 days, I’m gonna get you 250 reviews for the book.” Uh, and it’s like, “Yeah, of course.” Yeah, yeah. You know, it’s like, “Hey, I’m gonna need you to share this thing or, like, give me a- access to the buyers so I can email them individually or help them pre-write re- reviews or any of those things.”

[00:34:29] But, like, it’s a very specific thing to help with, and so many people are like, “Yeah, I have no i- I would love to do that, but I have no idea what.” It’s like if you spend a couple minutes looking, you can figure out what is this person trying to accomplish- 100% … and just come up with something really specific.

[00:34:41] Jayson: Yeah, I mean, the, the deepest way to invest in a relationship or start a relationship is to make people feel seen.

[00:34:45] Nathan: Mm-hmm.

[00:34:46] Jayson: So if you’re able to, again, invest that time and be like, “What is most likely most important to this person right now?” Yeah. Uh, given that they’re busy and all that kind of stuff, reviews are a great example.

[00:34:57] Um, you know, if somebody came to me… Dude, I was- Yeah, you’re getting- I was, I was getting so excited as you were saying all that stuff. And I was like, “That’s so kind of you, Nathan.” Um-

[00:35:05] Nathan: I’ve, I’ve got the whole day cleared. We’re gonna, we’re gonna get some reviews.

[00:35:08] Jayson: Fantastic. But no, it’s, I think it’s, uh, if you’re young and don’t have access to capital and that kind of stuff, and there’s also an element, I, I don’t say I get challenged on this, but, like, I look back on my journey and I’ve had a lot of lucky breaks.

[00:35:21] Mm-hmm. The right relationships at the right time and that kind of stuff, and I feel almost a responsibility that, like, w- if somebody has, is young and, like, has energy and grit and is honest and, like- Wanna, wants to help from a genuine place, I will do everything I can to, like, make that happen, uh, and make it a win-win.

[00:35:43] Um, because I, I’ve had, I’ve been afforded those, those chances as well, which has brought me to where I am today. So I think service is overlooked- Yeah … ’cause it obviously requires effort and energy. Uh, but it’s still a fantastic way- Yeah … um, to just plug into incredible networks or build incredible relationships.

[00:36:00] Nathan: Okay, so we’ve talked a lot about relationships as a whole, how we’ve acquired them and all that.

[00:36:04] Jayson: Yeah.

[00:36:04] Nathan: But I wanna go to this, um, this illustration that you have in the book.

[00:36:07] Jayson: Mm-hmm.

[00:36:08] Nathan: Um, tell me about this one, ’cause it’s much more about where the relationships… Like, what purpose do they serve? And ’cause it- it’s like I have lots of relationships, but, like, why does that matter?

[00:36:18] Jayson: Yeah, so the, the opening of the book, um, I talk about, we forge our first set of relationships based on proximity. Mm. The schools we go to, the companies we work for, the communities we belong to, the volleyball teams, and all that kind of stuff, and those are great. Um, but if you’re an ambitious individual, as you start to have these ambitions and goals, um, sometimes you’ll realize they’re not in alignment with the existing peer group you have.

[00:36:46] Um, that doesn’t necessarily mean you need to cut these relationships or any of that kind of stuff, but some of these relationships may carry as weight. I don’t know what your experience was leaning into entrepreneurship, but sometimes family members and that kind of stuff, there can be a lot of friction.

[00:37:00] Uh, and again, you don’t cut them off completely, but when you bring awareness to them, uh, you realize just how much they’re weighing you down.

[00:37:05] Nathan: Right.

[00:37:05] Jayson: Um, so the act of getting clear where you wanna go, and really what are you optimizing for, um, serves just as a really good, uh, a really good thing to kinda keep top of mind and- When th- looking at that through that lens, Jim Collins has a brilliant philosophy in his book Good to Great, that you want the right people on the bus, the wrong people off the bus, and the right people in the right seats.

[00:37:25] And I take the same lens when it comes to relationships. If my intention is to go here, who are the people I need on the bus? Who are the people I need off the bus? And who is gonna go in, in what seat effectively? Um, so, so yeah, that’s what this one is.

[00:37:38] Nathan: Do I think people always think about, okay, net new relationships-

[00:37:41] Jayson: Yeah

[00:37:41] Nathan: right? But this, this illustration is really like, oh, these other relationships that you’re bringing along might be not preventing you from getting there, but sure making it a lot harder.

[00:37:51] Jayson: Yeah. And, and, and listen, at the end of the day, you have finite energy and time- Mm-hmm … and bandwidth. And as a result, every relationship you say yes to here is keeping you from a relationship that can help you- Right

[00:38:04] to get to there. So I think there’s an opportunity cost that a lot of people are not aware of. Uh, and at least if you bring awareness to this, um, it just makes those… You can start making micro decisions, one could say. And it, again, it’s not, I think the mistake a lot of people make is like, oh, I have to have a hard conversation with this person or that person.

[00:38:23] As we talked about, a lot of relationship building is just how much energy you’re willing to invest into it. So if you’re going to be the person to bring people together for an event or a dinner or whatever the case may be, that’s quite a bit of energy that not a lot of people are willing to do. But if you are willing to invest that energy, amazing things can happen.

[00:38:39] When you bring awareness to s- like, some of those people that may be holding you back a little bit, you realize, like, oftentimes you’re carrying a lot of, you’re breathing a lot of energy into those relationships. And if you slowly start scaling back, those relationships will naturally go dormant effectively.

[00:38:55] Nathan: Well, I think the truth about relationships is that they all go dormant naturally.

[00:39:00] Jayson: Yes.

[00:39:00] Nathan: And that’s a double-edged sword, right? So if there’s a relationship that you don’t want to continue, you don’t have to sit down and be like, “Jason, we can’t be friends anymore.” Yeah. It’s like- Yeah,

[00:39:08] Jayson: yeah.

[00:39:09] Nathan: It’s just like, oh, if we just gradually, like more time between touchpoints and all that, like- Yeah

[00:39:13] it will naturally-

[00:39:14] Jayson: Correct …

[00:39:14] Nathan: drop off. But then the, the downside of that is that the, if there’s a relationship you really want, you have to- 100% … really put in the effort to maintain it. Yeah.

[00:39:23] Jayson: Dude, that’s brilliant as well. I should’ve included that in the book.

[00:39:26] Nathan: There’s plenty more podcasts for me to hear.

[00:39:28] Okay. This one I love because I have spent so much time in- Rooms and conversations, whether it’s a, early in my career at a, um, chamber of commerce business event- Mm-hmm … or that sort of thing where I’m like, “I don’t know, man. Someone told me I should network.” Yeah, yeah. This is the worst thing ever. Yeah.

[00:39:43] Tell me about this one illustration from the book.

[00:39:45] Jayson: Yeah, so the idea is, this is through the lens of entrepreneurs, um, but creators specifically, same thing. It is a isolating career path.

[00:39:54] Nathan: Right.

[00:39:54] Jayson: I think one of the things that makes it isolating, at least for entrepreneurs, is the scoreboard is very clear.

[00:39:58] It’s like capital raise, revenue, locations, head count- Yeah … all these things that we like to throw out there. So there’s always this, like, comparison. Mm. Uh, and the same thing with being a creator. Like, it’s like how many likes and views and comments do you get on, on threads and that kind of stuff. So as a result, this sense of isolation is, is very, very strong with those two career paths specifically.

[00:40:17] Um, and for me, uh, again, the premise of, like, you are rare unless you find yourself in the right room. So if you’re an entrepreneur on your second mountain, there are groups and organizations like MMT that would make you feel like you’re amongst companions on the path. They’re heavily kind of curated rooms.

[00:40:35] Um, if you’re a creator and you’re not going to Craft and Commerce, like, I don’t know if there’s any… Is there any other alternatives? There’s, I, there’s the event in Dubai, which I know you-

[00:40:45] Nathan: That’s a totally, we, we could get into… That’s a whole conversation about- But

[00:40:48] Jayson: the average- … completely agree, yeah … like, creator, there’s nothing else out there.

[00:40:50] Nathan: No, and it, yeah, that, like, not, like, that you can just- Yeah … buy a ticket to.

[00:40:54] Jayson: Yeah.

[00:40:55] Nathan: But is carefully, uh, selected for the right kind of people. Yeah. There, there’s not a lot, um, ’cause it, there’s a lot as, we’ll get into this in some other illustrations, like as you get into masterminds and- Yeah, yeah … that sort of thing.

[00:41:06] There, there are other events, but it’s-

[00:41:08] Jayson: So this is if you- … important

[00:41:09] Nathan: to

[00:41:09] Jayson: get- … you’re a creator alone. This is if you go to Craft and Commerce.

[00:41:12] Nathan: Exactly.

[00:41:12] Jayson: Great. Next

[00:41:13] Nathan: slide. Done. Sales pitch right there.

[00:41:17] Jayson: But it’s true, though. I mean, I’ve talked to people like Jay Clouse and, like, a slew of others that Craft and Commerce is this, like, almost annual pilgrimage- Mm-hmm

[00:41:26] of other creators where you are amongst, again, best practices will get shared naturally- Right … and all that kind of stuff, and you’ll leave with a great ROI. But just being amongst companions on the path is such a normalizing experience, and to me, a great- Indicator of like a worthwhile event or conference is if you leave, like, feeling energized.

[00:41:49] Mm-hmm. And, like, that would be the case. You know, I see people talk about Craft and Commerce. Yeah. And this is not to promote Craft and Commerce, uh, per se. I’m just like, if you’re a creator, you should go. Like, that’s the- Yeah … only place I know that you can buy access to like-minded peers. Mm-hmm. So yeah.

[00:42:05] Nathan: Yeah, and that was, you know, the reaction afterwards, that was something that was really special this year. And when we talk about events later, we’ll talk about the w- the momentum it takes to get there. But-

[00:42:13] Jayson: Yeah …

[00:42:15] Nathan: seeing… I actually went on LinkedIn and did a search for all the mentions of Craft and Commerce.

[00:42:19] Mm-hmm. Uh, I did it yesterday ’cause I was working for a presentation I’m giving on Monday, and it took a minute and a half of just straight scrolling to get through all of the recap posts that people had put just on LinkedIn. Mm. And you’re like… I mean, it, it was, it was insane, but it’s because exactly what you’re saying, people are leaving energized.

[00:42:35] Mm-hmm. So then as we talk about- Different types of communities. Mm-hmm. There’s a lot of different ones, from very broad to very narrow. I love that this illustration that you had here on the quality of relationships over time.

[00:42:47] Jayson: Yeah. So, um, not all environments are the same. Mm. Um, from a… Especially to drive, again, the quality of, of relationships.

[00:42:57] So I put in a bit of a hierarchy. And as we were kinda talking about offline, I’ve never heard anybody really define what is a conference- Mm … versus define what is a mastermind. Sometimes people label something a mastermind ’cause they can command a higher price point, but it’s really just a conference.

[00:43:11] Um- If I get

[00:43:12] Nathan: charged more than five grand, it’s a mastermind.

[00:43:13] Jayson: Exactly. 100%. Uh, and like communities, you know, are, hinge very much on curation. Mm-hmm. And community gets thrown around a lot. Yeah. There’s a lot that don’t necessarily just live within, uh, the one kind of category. Something that’s a conference may have some similarities to a mastermind, like MMT has, is, it’s community, but has like some mastermind-type components to it.

[00:43:34] Um, but ultimately, you know, a conference is where anybody can kinda sign up. It’s usually around an interest or what have you. So it’s a great place to meet some people with a similar interest, but there’s usually a couple hundred people there, couple thousand. Um, it’s, it’s a great way to get a lot of people in your aw- awareness, but there’s usually also not a lot of space to deepen relationships.

[00:43:55] It’s like usually session after session after session, so they’re not optimized for relationships. Workshops generally are much more intimate environment, and there’s this like feeling that you’re both, uh, or everybody’s committed to the same pa- kind of path or journey, which can be very kinda connective.

[00:44:10] Um, professional organizations would be something like an EO or a YPO for entrepreneurs. They’re great, uh, and they’re generally criteria-based. So for the entrepreneurs organization, your business has to do seven figures. For YPO, your business has to do eight figures. And again, you know, I think statistically 3% of general population are entrepreneurs, and th- uh, .4% of that 3% have businesses of seven figures.

[00:44:35] So to find yourself in an organization where it’s criteria-based, where the people you’re around- Right … are similar-sized businesses, uh, is a really unique opportunity. Um, and then above that you have masterminds. And again, this name, the, the label gets thrown around a lot. Uh, but at the end of the day- If it doesn’t tap into the collective wisdom of the group, then it’s not a mastermind.

[00:44:56] If it’s a guru at the front of the room-

[00:44:58] Nathan: Right …

[00:44:58] Jayson: it’s not a mastermind. Uh, and then communities are based on really shared values. Um, so for us at MMT, we have kinda core values at the forefront of our curation process. We have a pretty extensive curation process. Um, but that makes a really unique experience where, again, you f- truly feel like you’re amongst companions on the path at a f- probably similar stage of, of life and business, um, who again value the, the kinda same things.

[00:45:22] And in the book I talk about this funnel of, of relationships and how to kind of forge relationships quickly. And, uh, ultimately when somebody’s been vetted and you find yourself in a space like this, it’s a high trust space as well. Right. So you, these, in conversations here, conversations here tend to be like very surface level.

[00:45:40] Um, and then you’re trying to like weigh people out and all that kinda stuff. Uh, conversations here tend to go pretty vulnerable pretty quick. And relationships move at the speed of trust and vulnerability. So l- in an environment like a community, that is curated and it’s held with care. Person leading it ensuring that there’s no liabilities in the room and that kinda stuff, you can really condense decades of networking into a few short days.

[00:46:00] Nathan: Well, an example of that is, you know, I think about a, a, an early conference for me was one called New Media Expo. Mm-hmm. Uh, which was in Las Vegas. It w- um, I don’t know, 2013, 2014 or something like that. And I met a lot of people that I’ve been friends with for a long time later. But it’s these little sparks.

[00:46:15] Jayson: Yes.

[00:46:16] Nathan: And you’re exactly right. You’re not going deep, um, or any of that. Extreme contrast to that would be at, uh, Mastermind Talks this y- this last year, where there were two instances where I went from meeting someone, or I was talking, like talking to one friend there, and talking through like a struggle I had or whatever else, and they’re like, “Oh, you have to meet this other person.”

[00:46:38] And then like 10 minutes later we’re having like the deepest conversations about like marriage and relationships- Mm … and, you know, these things that really truly matter. And the shared values drive that. You know, there’s an immediate amount of trust ’cause it’s like, oh, okay, well if Jason has allowed them to come multiple years in a row or whatever, they must be incredible.

[00:46:57] Um, the level of expertise. And then just this idea of like, oh, we’re, we’re in similar places. It’s not- You know, if you’re like, “Okay, everyone here has built a really meaningful business. Everyone is doing work from a place of values.” And so the level… I, I mean, I guess in a, in a short way, I had conversations at MMT that in normal relationship would take years to get to the point where the, that level of authenticity and vulnerability could happen, and that to me is a community.

[00:47:26] Jayson: Yeah. Thank you for that. But whenever you put anything together like an event or- Yeah … you know, a community or what have you, it’s, it’s, it’s rare. Uh, it comes up, it bubbles to the surface every once in a while, but oftentimes you don’t get to hear some of those meaningful interactions. I always say, like, music is the space in between the notes, so sessions are great.

[00:47:45] Maybe you’ll get a great, you know, light bulb moment from hearing a speaker. Um, but usually the value can be found in like, you know, in the lobby or over dinner or those kind of things, and sometimes it’s, it’s hard to keep your finger on, like, those magical moments, so I appreciate you sharing that.

[00:47:59] Nathan: Yeah, for sure.

[00:48:00] So we’ve spent a lot of time talking about how to be intentional and curating relationships and getting in the right room and all of that, but something that you and I have both experienced is at a certain point in your career, a lot of these opportunities just come to you.

[00:48:11] Jayson: Mm-hmm.

[00:48:12] Nathan: And I think people feel jealous of that or like, “Oh, I’m not at that point.”

[00:48:16] But this next illustration that you have is really about great work attracting those people. And so what kind of way… And it’s easy to say like, “Oh, great work will attract opportunities,” but how do you actually bring that to life?

[00:48:29] Jayson: This was based on a, a quote by Naval Ravikant where he says like, “Forget networking.

[00:48:34] Do great work and your network will kinda find you.” Mm. And I think it’s a good frame to just offset what we’ve been talking about, which is a lot of like actively trying to find relationships, bring people into your world. There is an element of like you should pursue a craft and be world-class, um, and really commit to that.

[00:48:54] Because there… No matter how you slice it, there’s something called the social exchange theory where, uh, we naturally, consciously or unconsciously, wanna surround ourselves with people who are assets, uh, who can advance us, whether it’s, you know, our businesses, our careers, um, even just like advance us, uh, relationally and, and those kinda things.

[00:49:14] So, uh, as a result, it also makes my life a lot easier when I have a peer group of people that are world-class in different domains ’cause I can easily connect them to each other and that kinda stuff. So I think there is this element of, um, yes, you can be the person, if you go wave a magic wand, that brings all these great people together, or you can even buy access to find yourself in the right room.

[00:49:33] Uh, but the quality of your work and what you’re known for is what keeps you in that room. Um, so I do, uh, I, I mean, for, for me, in theory, the last 14 years, I’ve pretty much committed my life to building community. And like that is very much like my space, and when friends reach out to me, it’s usually on that topic.

[00:49:52] Um, so yeah, that’s what this was designed to illustrate.

[00:49:55] Nathan: Yeah, and I think it’s, you know, this idea of swimming upstream, like every… I think a lot in terms of conversion rates.

[00:50:01] Jayson: Mm-hmm.

[00:50:02] Nathan: You know, it’s like, okay, how do we get attention with an idea? And the better the idea is, the more attention it’ll get. And then how do we go from that attention to, um, you know, whether it’s watching a video, and then from watching the video to an email list, and then maybe ultimately buying a product or, or whatever else.

[00:50:16] And I think about what are these leverage points that gra- that will increase your conversion rate all the way along. And so if you think about, um, like Andrew Wilkinson’s example- Mm … of Moxie and like he’ll reach out to anyone and all of that.

[00:50:29] Jayson: Yeah.

[00:50:30] Nathan: And if he has a one in a thousand hit rate of that working, you’re like, “Ooh, that’s a pretty rough thing.”

[00:50:36] It’s like, okay, but what would have to be true for Andrew to get to a one in 100 hit rate? Because that now all of a sudden, it’s hard, but it’s worth it. And then what would get us to a one in 10 hit rate? ‘Cause then it’s like, well, I should be spending every morning sending out 10 emails or that sort of thing.

[00:50:53] Like that, that’s worth it. And doing great work is that thing that elevates everything else that you do

[00:51:00] Jayson: Dude, I should’ve wrote this in the book. That’s a great fr- it’s a brilliant frame because, again, Andrew still does these cold outreaches- Right … to this day, but his hit rate- … given who he is now, it’s like every outreach gets a response, right?

[00:51:12] Right. Which is…

[00:51:13] Nathan: And if- the response might be, I mean, it, it… Like, if I were to host this Author Mastermind 10 years ago- Mm … and I were to do it by myself, right? I might be at a 1 in 10 response rate.

[00:51:23] Jayson: Mm.

[00:51:24] Nathan: Let alone who actually shows up. I

[00:51:25] Jayson: would still go, Nathan.

[00:51:27] Nathan: I appreciate that. Right? But now with where I’m at, the relationships- Yeah

[00:51:31] the room we can curate and all of that, we have 100% response rate, and if people say they can’t come, 9 times out of 10 it’s because I have a keynote speech that I’m being paid $50,000 to give- Yeah … on that same day. Otherwise, I would be there.

[00:51:45] Jayson: Yeah.

[00:51:45] Nathan: And so I just don’t think that people obsess over doing great work enough- Yeah

[00:51:49] because it’s the The conversion rate increases your cost of everything that you do.

[00:51:54] Jayson: Yeah, and I, I, I share a couple stories in the book, um, of people doing great work and then found the spotlight and then blew up. Mm-hmm. ‘Cause nothing’s worse than… I have so m- so many friends that are working on their personal brands.

[00:52:07] Mm. And they’re like, “Oh, if I only just got on Diary of the CEO.” And I’m like, “You don’t wanna go on Diary of the CEO. You are not ready.” Yep. Have you seen James Clear interview on the Diary of CEO? It is so tight. Yeah. I watched that interview and just in m- marvel of, like, how clear of a communicator he is, or Vanessa Van Edwards, another mutual friend.

[00:52:25] Like-

[00:52:25] Nathan: Va- Vanessa told me that she did 70 hours of prep for her Diary of a CEO episode.

[00:52:29] Jayson: And she’s already world-class. Like, you know what I mean? Like, I w- I’d call on that st- thank you for allowing me to be on your show. Uh, but, like, I’m not ready for that. Like, I know that. Like, I’m probably five years away of, like, h- a lot of this hard work, um, before I’m ready for, you know, the larger stage.

[00:52:46] Um, and I just, I think people want it too quickly. Mm. Um, and again, through the lens of relationships. The whole Andrew Wilkinson story is again a great example. The reason why Bill Ackman took interest in Andrew is ’cause he found him fascinating. The reason Andrew was able to build a relationship with Charlie Munger, who is Warren Buffett’s right hand, and Charlie was actually asking Andrew questions about, like, online businesses, it because he is, like, world-class at, like, online businesses.

[00:53:12] So I do think that there is this element of, like, you need to be known for something. Mm. Uh, there was that saying in, in business, you’re known for something or you’re known for, or remembered for nothing or what have you. Mm. Um, so I think, um, yeah, it’s just really, really important and I th- I never thought about it from a hit rate perspective, but you’re, you’re so, so right.

[00:53:29] Nathan: Well, and I think it’s, like, really putting in the work and the reps and doing it in a practiced way.

[00:53:35] Jayson: Mm-hmm.

[00:53:36] Nathan: So two people that have really stood out to me that kinda started their online businesses at the same time, um, are Cody Sanchez and Nick Huber.

[00:53:44] Jayson: Mm.

[00:53:45] Nathan: And so really around this 2019, 2020, 2021 is when they started to take content really seriously.

[00:53:53] And, um, I actually met Nick at, um, Cody’s conference that we were both speaking at. And spending more time with him I realized, like, oh, they, they are so polished on camera. And I made a comment to Nick about it and he was like, “You just have to put in the reps.” And we were at a, uh, like kind of a little mastermind event in, in Cabo driving a golf cart and he’s like, uh, and he’s just talking about you gotta put in the reps, you gotta do this.

[00:54:15] And I was like, “Okay, but how do you do that?” And he pulls the golf cart over, grabs his phone, and goes, “Okay, I’m here with Nathan Barry. Nathan, what is your number one piece of advice on hiring? Go.” Mm-hmm. And I was like, “Uh, uh, uh,” and he just goes, “Yeah, do more of that and you’ll be good.”

[00:54:28] Jayson: Yeah.

[00:54:28] Nathan: And then I had a conversation with Ramit Sethi a couple weeks ago ’cause I’m working on a book launch as well, and he’s like, “Yeah, if you wanna talk book launch advice and, and everything.”

[00:54:37] And you know, I’m, I’m happy to chat. And so talking to him and he said, you know… I was asking him about, like, how do I craft the right pitch to go on a podcast ’cause I have all these relationships but I don’t wanna ask for something, you know, and all this stuff. And he’s like- That’s not the thing to focus on.

[00:54:51] Mm-hmm. He’s like, “You’re not good on camera yet.” What you need to do is you need to focus on media training, and you need to put in all those reps ’cause you’re gonna put in… Most people are gonna put in 90% of the effort to be like, “Okay, how do I get on Ritual or Diary of a CEO or some of these other things?”

[00:55:05] And then 10% on actual delivery, and he’s like, that, like invert that completely.

[00:55:10] Jayson: That’s a good friend.

[00:55:10] Nathan: Yeah. Yeah. He’s a very good friend. Who else knows you directly?

[00:55:12] Jayson: Yeah.

[00:55:13] Nathan: And so that’s the thing that I’ve been thinking about of like, okay, how do I keep doing great work? ‘Cause then people will see. They’ll be like, “Oh, when Nathan goes on these shows, it’s one of the highest view counts that we had,” or, “The retention is really good”- 100%

[00:55:26] or, “I love the interview,” or something like that. And you’re like, okay, I’m focused way too much on the outcome and the things that are not within my control, and not nearly enough on the great work, which is entirely within my control.

[00:55:40] Jayson: And the beautiful thing is, um, I mean, you only have one chance at bat, like, on those larger platforms.

[00:55:45] Um, and if you’re good, and you hit it out of the park like Vanessa did, like, you’re- Right … they want you back. Like, she- Right. She’s been three

[00:55:51] Nathan: times …

[00:55:51] Jayson: I think she has… Yeah, and she has, like, one of the top 10 fastest growing, like, episodes or- Yeah … top five fastest- Oh, yeah … growing episodes on Diary of a CEO ’cause, like, it’s so well done.

[00:56:00] Such a huge fan of hers. Um, yeah, no, I mean, I, I think I, I, again, people try to, to, to jump ahead too quickly, and, uh, I think it is, it is very much a mistake.

[00:56:09] Nathan: Hey, so you may know me as the host of this podcast, but I’m also the founder and CEO of Kit, an email marketing platform for creators. I built Kit because I needed a better way to grow my audience and sell books and courses through email.

[00:56:22] Kit helps you build an audience that you own and will create automations that keep working for you so that you can focus on creating. As a listener of this show, you can get an exclusive 10% off Kit Pro if you go to kit.com/nathan. Okay, but then this last idea that I wanna talk through is the idea of how doing great work isn’t enough.

[00:56:39] Jayson: Yeah, so there’s a fantastic principle, uh, called increasing your surface area of luck. It was initially coined by, uh, Jason Roberts, who’s a, I believe a developer. This is probably 15 years ago, and there’s been a couple people, Sahil Bloom, one of them, that has really popularized it as of late. And the idea is if you wanna increase your surface area of luck, you wanna do great work, and you wanna tell people about it.

[00:57:04] There’s a lot of people that do great work and don’t tell people about it. I’m guilty of that. Uh, there’s people that don’t do great work and talk a lot. We all know those kind of people. And the sweet spot is, again, doing great work and talking about it. The one thing I think that principle misses is the importance of deep relationships- Mm

[00:57:24] ’cause you… It does… I always say it doesn’t matter how many friends you can count, it matters how many friends you can count on, and I much rather have 500 deep relationships, people who have my back, than, you know, 50,000 followers on Instagram or what have you. Um, so that is why I redesigned the surface area of luck to have basically do great work, let others know, uh, and in- invest in deep relationships, and then as a result- Mm-hmm

[00:57:48] your lu- luck multiplies.

[00:57:49] Nathan: Well, I think it’s such an important idea because it’s not just about- “Oh, he got lucky.” Well, of course, Jason happened to be at this event, you know, and then that was where he met this person and it went on from there, right? Um, it’s all of these things that increase your service area for luck.

[00:58:07] Mm-hmm. And then it’s like, yeah, I actually get lucky quite often because there’s so many opportunities for that to happen.

[00:58:13] Jayson: Yeah.

[00:58:13] Nathan: But the depth is so interesting because I feel like that’s what most communities are missing, is they’re like, “Okay, we got really high, uh, high profile, very successful people and, you know, we put them in the room together and we curated the room.

[00:58:28] But then they don’t go and actually create the environment where you can share. And so it’s like the questions that you, you might ask in one of those rooms is like, “Hey, what’s, what’s worked best for growth for you in the last year?” You know? And then you’re like, “Business growth?” “Yeah, yeah. Business growth.”

[00:58:43] And they’re like, “Oh, well, this one thing that we did in- increased our revenue growth by 10%,” or something like that. And when you really go to the depth, then, you know, you’re like, hey, you wouldn’t lead with this question, but like, you know, what are you struggling with as an entrepreneur?

[00:58:57] Jayson: Yeah.

[00:58:58] Nathan: You know? And, and building these relationships.

[00:59:01] And so I think about MMT and the depth that comes from it. You can just dive deep into these conversations. Like, um, when Ben Greenfield came over to my house, you know, we’re talking about parenting and rituals within our families and how we wanna show up and what we struggle with and all of these things, and it’s because the container that we met in and the types of people that we like, it- that just became entirely natural.

[00:59:27] Jayson: Mm-hmm.

[00:59:27] Nathan: And so I love the, the approach just on, not just on depth in relationships, but also in the style of how you go about it.

[00:59:33] Jayson: Mm-hmm.

[00:59:34] Nathan: One thing that I’m so curious about is how do you systematically create that depth?

[00:59:38] Jayson: I guess what plays on this is something I stumbled across, I think it was actually initially from Jay Papasan, who I know- Yeah

[00:59:46] has been a guest on your- Yeah … your podcast. And this was probably back in 2017 or so. He was sending out these, this email newsletter to friends. Mm-hmm. Um, it was just, like, a little insight as far as what was going on in his world, like personally and professionally, stuff that he wouldn’t put on social media.

[01:00:05] And I had done a similar type email for the last couple years, and, uh, a couple things really reaffirmed the value of this exercise. First, well, maybe five years ago, five, six years ago, I started investing in companies. I used to put that on my LinkedIn. That was a mistake. Then I just started getting a bunch of pitches.

[01:00:25] Yeah. And also, investing is romantic until you realize, like, oh, I’m now, like, on your, unofficially, like, not on your payroll, but working for you- Right. Yeah, exactly … to, like, make more introductions. You

[01:00:34] Nathan: paid me and you now work for me.

[01:00:35] Jayson: Exactly. Make more introductions and all that kind of… So I don’t invest anymore.

[01:00:38] Yeah. But one of the things I, I enjoyed about the investing process was, like, the monthly or quarterly emails I’d get from founders as far as, like, updates as far as what was going on in their business. Because on some level I could feel like I had, um, insight as far as what was going on and maybe ways I could potentially support them.

[01:00:54] I was just emotionally invested- Yeah … in these updates. And- I thought about it that I have so many people who have invested in me, not necessarily financially, but have their fingerprints on my journey, and I’m not providing them any kind of updates. So as a result, I started getting much more religious with these, like, these, uh, what I call friends-only updates.

[01:01:14] And there’s a handful of friends of ours that have something similar. Nick Gray, we were talking about. Um, he has a brilliant one. It’s just so, so creative and so engaging. Uh, Andrew Wilkinson, who we’ve mentioned a few times, has one as well that’s kind of public. Uh, you have one in your own form, which is an annual update-

[01:01:29] Nathan: Yeah

[01:01:30] Jayson: which I’ve read every year except for this year because-

[01:01:33] Nathan: Oh, I didn’t write one this

[01:01:34] Jayson: year. Shame on you. I don’t know what’s going on in your world, and I can’t, as a result, make introductions and increase- Right … your luck. ‘

[01:01:41] Nathan: Cause you don’t, for, for the first time-

[01:01:43] Jayson: Yeah …

[01:01:43] Nathan: uh, in a decade, you don’t have a list from me of what my goals are for the year.

[01:01:48] Jayson: I don’t know what your goals are. I don’t know- … well, yeah, what your focus is. I don’t know what some of your- Yeah … your challenges are. And so I’ve, I’ve religiously, that’s a lie. Because they can be a lot of work, uh, I don’t get them out as, as often as I want to. Mm-hmm. But when I do, the value is incredible.

[01:02:06] Example, in 2020, our business went down to zero. Yeah. Um, we’re in the events business. W- all of our product SKU is one thing. It’s a live experience. Terrible industry to be in in 2020. We were about to lose our house. Mm-hmm. And I sent out an email to these people on my friends-only list saying, “Hey, I’m looking for…”

[01:02:27] So I, it’s always an update, and then because I have a hard time asking, the forcing function is, like, I have to include one clear ask in every email. And the ask in this email was, um, “I’m looking for creative financing solutions for our home ’cause we have a farm, it’s hard to get mortgages for. My business is zero, I’m broke now.”

[01:02:46] Yeah. Um, “We’re about to lose our, our house.” And I had a handful of m- people reach out, say, “Look, I’ll lend you the money,” all that kind of stuff, and then somebody reached out and said, “Hey, have you ever thought of selling lifetime memberships for MMT?” And I was like, “No, I’m not gonna sell… That’s nuts.

[01:02:59] Nobody’s gonna buy a lifetime membership for MMT.” But then it gave me the idea of like, well, maybe I can sell one, three, and five-year credits for MMT. And as a result, I sent out an email to our membership. We brought in, like, half a million dollars within a day, uh, with- or within two days, and ultimately, that saved the business.

[01:03:17] Mm-hmm. Uh, and has led to, like, seven figures, ’cause we’ve used that same model every year. There’s some people, uh, like Noom in the community, has nine years of MMT. Nine years. Every time he has an office, he’s buying, buying more credits. I’m like, I, I, yeah, I hope I’m still alive in nine years to deliver on these.

[01:03:31] Um, so but that one email led to so much stuff like that, so every time I send out these emails, it increases that surface area of luck. Mm-hmm. People know what’s in focus for me, know what’s a priority, can open doors that I never kinda could’ve predicted. So that’s the actual tangible way that I increase, uh, that surface area.

[01:03:50] Nathan: Quick random question.

[01:03:51] Jayson: Yeah.

[01:03:51] Nathan: First, I’ve seen so many people do that.

[01:03:53] Jayson: And I use Kit to se- I do.

[01:03:55] Nathan: Yeah?

[01:03:55] Jayson: I do. It’s ama- I mean, look at, you should look at my open rates. I actually refrain from sending, uh, trying to send any other emails b- ’cause my open rates for those friends-only emails is, like, 85%. Insane,

[01:04:05] Nathan: yeah.

[01:04:06] Jayson: Uh, yeah, so.

[01:04:07] Nathan: I think it’s such a great, great tactic because it’s the, I just wanna hear from my friends when their guard is down and there’s no polish.

[01:04:14] Jayson: Mm-hmm.

[01:04:14] Nathan: If we were sitting down and having coffee-

[01:04:16] Jayson: Yeah …

[01:04:16] Nathan: and I was like, “Hey, man, how’s life?” That answer, that’s what you put in the friends only update. And because it’s not going out to tens of thousands of people and whatever, like you can do that.

[01:04:25] Jayson: And one of the things I’ll just share that shows this tangible value from a relationship that’s at scale perspective is every one I do, I record a video to accompany it. If anybody wants to like hear my voice instead of read the email. Yeah. And I’m shocked how many people watch a video. Sometimes it’s an hour long.

[01:04:40] They watch it from beginning to end. And there was, uh, one I sent out recently where the video, and this is a small group of people I send it to, had 200 hours of watch time. And I was like, that has saved me 200 hours of updating people- Yeah … what’s going on in my world. So although it’s a lot of work to craft this email, it’s, it’s hugely valuable from a leverage perspective.

[01:04:59] And the one thing I’ll just throw in there really quickly, ’cause a lot of people are like, “Well, who do I put on the email?” Um, I, as a rule, I only email people, um, that I feel like if they were to receive my email, they’d be excited-

[01:05:11] Nathan: Mm-hmm …

[01:05:11] Jayson: when it lands in their inbox. I still give them the option to unsubscribe, and I encourage them.

[01:05:15] I’m like, “If you feel like this is noise, like there’s a lot going on in your inbox anyways, I will not take offense.” Yeah. The amount of people who’ve unsubscribed in the last like six years, I can count on one hand. So that is the layer or the filter of like who gets included in the email. Uh, and then on the backside, it’s, it’s, it’s a two-parter.

[01:05:32] If they were to reply to the email, I don’t feel dread that I have to like- Right … oh gosh, now I have to answer to this. Because we have those- Yeah … sometimes too, right? So that is, as long as they pass both of those filters, then they’re included in the email.

[01:05:43] Nathan: I love that you have all these filters on curation.

[01:05:46] It’s so important. And they’re always simple.

[01:05:47] Jayson: Yeah. Super simple, yeah.

[01:05:49] Nathan: But, but they’re really meaningful.

[01:05:50] Jayson: Yeah.

[01:05:50] Nathan: Very tactical question. Hmm. If you were in this position of being slightly more than halfway through a year and you feel, feel guilt about like not writing the update, ’cause I actually, I have written that update every year in a row for 13 years- Yeah

[01:06:02] except for-

[01:06:02] Jayson: 13 years?

[01:06:03] Nathan: Yeah.

[01:06:04] Jayson: Dude, wow.

[01:06:04] Nathan: And maybe more. No, it’s probably, 2011, so for 15 years. Yeah. Except for 2025.

[01:06:10] Jayson: So you’re the originator of this.

[01:06:11] Nathan: I, I… Well, I got it from Chris Guillebeau.

[01:06:13] Jayson: Oh, really? Wow.

[01:06:15] Nathan: Um, I learned, I’ve learned so much from that man. And I always say that I write it for myself. And so I actually have one that’s halfway written.

[01:06:20] Mm-hmm. I’ve just, at this point, like I, I ran out of time around the holidays and all that, so I didn’t actually-

[01:06:24] Jayson: Yeah …

[01:06:25] Nathan: finish it and publish it. ‘Cause it is a lot of time, and I like put in all the photos and all the stuff.

[01:06:29] Jayson: Yeah, yeah.

[01:06:29] Nathan: Um, but now I just feel like, oh, it’d be super weird to put out a 2025 annual review on August ’26.

[01:06:37] Jayson: 20- Yeah, exactly. 2025.5. Uh- Yeah, I don’t know. There’s also the element that you don’t wanna break the chain. Doing this for 15 years-

[01:06:45] Nathan: Right …

[01:06:45] Jayson: is, uh-

[01:06:46] Nathan: So yeah, which is worse- You don’t wanna gap … the awkwardness? And, and yeah, the, the gap would be way worse than the awkwardness. So I gotta, I gotta buckle down.

[01:06:52] Jayson: Dude, I’d be so ha- If you just sent, like, a quick email of like, “Hey, I messed up. Jason called me out on my podcast.” “Here’s the half-written version,” I’d be, I’d be the first one to reply and be like, “Good on you, Nathan. It’s great to, to see what was, you know- Oh, I get it … year 2025.”

[01:07:05] Nathan: Yep. I will, I will

[01:07:06] Jayson: do that.

[01:07:07] That’s powerful. That’s really power- W- w- the w- No matter the way you do it- Mm-hmm … whether it’s annual updates, if you don’t have, uh, something like a trigger-

[01:07:13] Nathan: Mm-hmm …

[01:07:13] Jayson: uh, like, oh, it’s a turn of a new year, it can sometimes easy, be easy to, like, push it back and push it back and push it back. So the idea of doing it annually at a minimum I think is fantastic.

[01:07:22] Nathan: I also know someone, speaking of triggers, who does it quarterly.

[01:07:26] Jayson: Hmm.

[01:07:26] Nathan: And he just has, like, he just has a 90-minute block once a quarter, and whatever he writes out, he just hits send at the end of 90 minutes.

[01:07:36] Jayson: Hmm.

[01:07:37] Nathan: And because it can grow, you know, I might spend- Oh,

[01:07:39] Jayson: 100% …

[01:07:39] Nathan: 10 hours writing an annual review post- Yeah

[01:07:42] then formatting it in WordPress. Yeah. You know, which photos do I wanna include, what … You know, and all of that. And so it can just grow and grow. And so he was like, “No, it’s… If I’m having coffee and catching up with a friend, it’s probably for 90 minutes. And so I’m doing that at scale. And, like, did I tell the update of what’s going on with my kids to Jason the most perfect way?

[01:08:01] No, I told him the version that fit within the time that we had.”

[01:08:03] Jayson: Yeah. Done is definitely better than perfect. And I’m sharing this vulnerably that, like, I struggle with perfection as well, and I don’t do it at the level of, of cadence I should. Um, but potentially embracing that 90-minute frame, I actually really like that.

[01:08:17] Nathan: Yeah. So the last thing that I wanna go to that might be the most important for, for our audience is this idea of the difference between, like, a fan base and a community.

[01:08:26] Jayson: Mm-hmm.

[01:08:27] Nathan: Because I think so many people listening will have tens of thousands of followers, and they’re like, “Oh, I have this great community,” or if I were to host an event or whatever else, like, lots of people would, would come.

[01:08:38] We’ve sold things out. And everyone is there because of that one person.

[01:08:43] Jayson: Mm-hmm.

[01:08:44] Nathan: And what you’ve done with MMT is you’ve made something that, like, you created the whole thing. You curated the group and all of that, but- The magic continues even when you’re not in the room. Mm-hmm. It’s not like, oh, we’re all huge fans of Tim Ferriss, and so if he doesn’t show up, we’re devastated.

[01:09:02] We’d be devastated if you didn’t show up to MMT, just to be clear. But, like, it’s so much more about the community. And so I’m curious, what advice would you give to someone who’s like, “I don’t just want fans of me, I want all the… I wanna bring people together to really connect”?

[01:09:17] Jayson: And this would be through the lens of in person?

[01:09:19] Nathan: In person or online, and maybe it’s different answers.

[01:09:23] Jayson: Yeah. I mean, for me, and I obviously would appreciate you chiming in here ’cause this is, you have experience and expertise in this arena as well, um, I do think there’s nothing that compares to in person. Um, I mean, that’s just a matter of fact. Uh, to have people in a room is just such a, a gift, especially if they’re disconnected and are on their phones and that kind of stuff.

[01:09:42] It’s such a rarity where they’re not, like, getting hit with different responsibilities and, and emails and all that kind of stuff. And then, you know, the, the whole shift of Not being focused on the individual and more about the community. I mean, there’s a couple things that, that I try to consciously do.

[01:09:59] Like, I see myself almost, like, as the bouncer in front of the club. Yeah. Ensuring I have the right people in the room. So for us at MMT, there’s three levels to our curation process. There’s demographics, value graphics, which are our core values, uh, and then synergy. And one of the most important things that I realized many years ago is how you run a community of 150 people is exactly how you run a company of the same size.

[01:10:20] Uh, so the importance of keeping, like, core values at the forefront of your curation process, and then people who are in the community, coach them up or coach them out based on those core values. It’s a distinction I often share, and people are like, “Oh, yeah, that sounds…” No, like, it’s, it’s so valuable. Like, just do that and you’ll have an amazing community.

[01:10:36] Right. I draw so much inspira- The most inspiration I draw as far as how to make a better community environment is all through hiring best practices and culture. You gave me an idea years ago which eventually, eventually became our MM3s. Mm. Which are one of the most highest rated things, uh, our community does in between our live events, which is a, a thing that you, uh, instituted at, at Kit.

[01:10:57] Can you tell?

[01:10:57] Nathan: Yeah. The idea of… We call them subs.

[01:10:59] Jayson: Yeah.

[01:11:00] Nathan: And it was just a conversation. This is a Slack bot that we have.

[01:11:04] Jayson: Yeah.

[01:11:04] Nathan: That every week it goes and grabs three people at random and says, uh, “You should all have a 30-minute call this week.” Yeah. And, uh, it picks one of you to be in charge to pick the time and to make sure that conversation actually happens.

[01:11:18] And it will… We go back and forth, but it’ll often give a, uh, conversation starter as well.

[01:11:24] Jayson: Yeah.

[01:11:24] Nathan: And basically, the idea is that the two of us together are going to have one type of conversation. We might pick up one from, uh, six months ago, or, you know, it might be about the work overlap that we have or whatever.

[01:11:36] But if you add in a third person, it’s a totally different dynamic.

[01:11:38] Jayson: Mm-hmm.

[01:11:39] Nathan: And you can basically have unlimited combinations of three people, and that has built such deep community and relationships within our company that when, when people show up for, um, our Team Retreats, which I’m here in Toronto right now for, for our Team Retreat that’s kicking off tomorrow.

[01:11:55] There’s, like, real depth and meaning, and they’re not like, “Hi,” you know, “My name’s John, I work in engineering. Who are you?” You know, they’ve, they’ve had all this community and interaction, and it matters so much.

[01:12:05] Jayson: Yeah.

[01:12:06] Nathan: So you did that with MM3s.

[01:12:08] Jayson: Yeah, so we integrated that in MMT, and then, and people love it.

[01:12:10] We just pair three members together virtually. Uh, we get them to fill out an intake form in advance so we understand what their focus is- Yeah … so maybe we can make pairings. ‘Cause what people love most about our MMT live experiences oftentimes is the assigned seating. Mm-hmm. And the curiosity that they have- Yeah

[01:12:23] of like, “Oh, why am I seated next to this person?” So we just took that idea and brought it kinda digitally. I share this because- Again, there’s so much inspiration you can draw from like culture best practices in business that you can bring into the community space, because there’s not a lot of good resources- Right

[01:12:40] on how to build community, how to get the right people in the door, how to kick people out. It’s, it- but again, it’s very much just culture principles. And then for me, like, I see my role, again, as that curator, uh, and the protector of the community. So if we have to kick people out, which happens, um, you know, I, I, I’m the bad guy in that, in that case.

[01:12:58] And then when it comes to our live experiences and that kind of stuff, I think one of the most important roles I have is to set the container on the morning of day one. Mm. Um, so like, why are we all here? What are the, the rules of engagement? All that kind of stuff, and do it in a much better, like, storytelling type way.

[01:13:16] You don’t want it to be kinda dry. Um, but getting people to fly in formation early- Mm … is great, and then I can kinda get out of the way. And then we design our live experience so that there is a lot of space for people to kinda connect outside sessions and, and those kind of things. But, um, yeah, I mean, my area of experience or expertise is very much community-building, kinda like in person.

[01:13:36] Uh, I always am in awe and marvel those who build communities like online and have active, uh, you know, communities on Circle and that kind of stuff. Um, so yeah. Is there anything you could chime in there? Especially I guess on the, maybe the digital side.

[01:13:51] Nathan: Well, I’m thinking about, since you brought up the idea of, um, you know, these, these triads of, like, bringing three people together.

[01:13:59] Jayson: Yeah.

[01:14:00] Nathan: It’s something that I don’t think enough online communities do.

[01:14:03] Jayson: Mm.

[01:14:03] Nathan: Because really, any… It, it scales. It doesn’t require you as the host. Uh, ’cause you could, you could fully automate it. Yeah. You could, you, or you could go fully curate. Like, you could decide any of those things. There’s a, there’s a, a fun in the, like, I don’t know, this is the random group- Yeah

[01:14:20] you know, in the company. It’s like, all right, we’ve got our accountant, we’ve got our, you know, uh, COO, or you know, like, and, and then we’ve got our head of brand, and they all… All right. What, what do they end up talking about? Um, or there’s also the magic of like, no, I, I think that you three would have a great conversation.

[01:14:37] Yeah. But I don’t think communities do that enough. Like, I think about- You know, the, these online communities like, um, Jay Clouse’s The Lab, you know, that would be such a good fit, and maybe they’ve done something similar. Yeah. Right? To continue that. ‘Cause all of these online communities, the thing they struggle with is, how do I get continued engagement that’s not just about the training or about the host?

[01:15:00] Jayson: Yeah. And he’s a great example of somebody who is trying to bridge that gap, and now investing quite heavily, uh, on, like, in-person experiences. And there’s a learning curve to that, but he’s doing, you know, obviously a, a great job. But there’s that saying that people come for content, but they stay for community.

[01:15:15] And, like, that is oftentimes, like, the deciding factor, um, when it comes up for, like, renewal and that kind of stuff. And if you could do a good job of making those connections, whether it’s activities like that. At MMT, we have a session every other month where we bring our members together and I facilitate two breakouts- Mm

[01:15:31] which is an opportunity for them to deepen ex- existing relationships and connect with new members. Um, I also try to do a good job spotlighting the genius in the community. Yeah. Uh, because there is so much, you know, genius effectively. Um, so things like that are, go a really long way.

[01:15:47] Nathan: On the idea of, like, maintaining this engagement and, and not just being about the content, um, I think, like, the ask, give, praise model- Yeah

[01:15:54] of MMT is really powerful.

[01:15:56] Jayson: Yeah.

[01:15:56] Nathan: Can you talk about how that works?

[01:15:58] Jayson: Yeah. So I, um, I stole some of this, uh, from an event I went to in 2011- Oh … um, that Tim Ferriss put on, and theirs was ask and give. And, uh, Tim came up with this Frame because he saw a lot of… This, our community for that group lived on Facebook.

[01:16:18] And, um, they can be filled with… People don’t know what to post, so th- or there’s no rules, no clear rules. So people will be like, “Oh, I just did a new blog post.” And, like, well, then if you did a blog post, well, I’ll talk about my- Yeah, me too. Yeah … Here’s a tweet I did or whatever the case may be. Yeah. And then it just becomes- Here’s my

[01:16:33] Nathan: Amazon affiliate link.

[01:16:33] Jayson: Exactly. It’s like- And there’s just a lot of, lot of noise and very little signal. And what Tim framed for that group was everything has to fall under an ask or a give. Mm-hmm. Uh, so you’re either asking for something or you’re giving something, nothing else. And I think-

[01:16:46] Nathan: That is really clear ’cause then it’s not like, “Oh, I’m telling you about this great resource, and if you really like that, you should buy this product- Yeah

[01:16:54] from my company.”

[01:16:55] Jayson: And be like- Well, sometimes people get a little creative and they’re like, “Well, I would love to give my blog post to everybody.” So sometimes n- moderation is required. But ask and give, uh, I think, which, it, it’s a very relatively clear set of guardrails. Mm-hmm. Without, like, micromanaging every single post and creating almost like this…

[01:17:11] Sometimes you almost create this uncertainty. ‘Cause we do have members reach out sometimes. They’re like, “Hey, does this fall under an ask or a give?” Um, but to me, what I’ve seen the last 15 years, it, it serves really well. Yep. And the one thing we added on top of that is praise. Mm-hmm. And that really im- reinforces the value of the community.

[01:17:28] Um, so that’s when a, a member has an interaction with a fellow member that they wanna spotlight. And so oftentimes we’ll see somebody make an ask of like, hey, you know, we got one this morning of like, “I need a litigation lawyer for a- Right … bad business partnership.” Within three, four minutes there was like four or five suggestions.

[01:17:45] I guarantee there’s like, that’s probably dealt with now. Um, as far as that person being on their path, I would not be surprised in two weeks time they’ll close the loop and say- With praise … “Yeah, I thank you for the connection. I got it all solved,” or whatever the case may be. So the praises are just a great way.

[01:18:00] Also from a community building perspective, the storytelling is so rich. Like, I, we have hundreds and hundreds and hundreds of praises over the years that we can point to of like how the community has paid off significantly for people. Right. So everything falls within ask, give, praise, and we also integrate that as best we can at our live experiences.

[01:18:19] Uh, so we use praise cards, which is a really cool activity that we do. Um, and, uh, and that kind of stuff. So that’s been our model.

[01:18:26] Nathan: There’s a couple things I love about that model, but particularly the praise portion of it.

[01:18:31] Jayson: Yeah.

[01:18:31] Nathan: Um, one is at the live events, it gives you this moment of reflection a few times throughout the event.

[01:18:38] Jayson: Mm-hmm.

[01:18:39] Nathan: And it, if you think about- You know, like value is a nebulous thing. Was it valuable for me to come to this conference or whatever? Yeah, and then by flipping through my notebook later, like what were my takeaways? Was it worth the ticket price or the… Or more, more so the ticket price, the, was it worth- Time

[01:18:54] three days- Yeah … or, you know, four days to- Big investment … be here. But you’re basically solidifying these, the, like the value that I got over time. And like writing it, we’re writing it on a card. Mm-hmm. But we’re also writing it on our subconscious simultaneously. And then the second thing that I think it does is it reinforces the idea of the value of the network.

[01:19:15] Jayson: Mm-hmm.

[01:19:15] Nathan: Again, if you, if you think about the model of, I don’t know, if, if there’s an event, let’s say like an Alex Hormozi, someone like that, right? Where if you go to a workshop that he’s putting on, you’re here to learn from him. Did he answer your question? Yes. I’m sure that if it’s an expensive event, there’s probably other interesting people there who can afford the ticket.

[01:19:32] But like it’s very much-

[01:19:33] Jayson: Yeah …

[01:19:34] Nathan: back to him. But the praise is just this mechanism that constantly reinforces like what interactions did you have with these other people? And then the virtual, um, praise You know, when people are doing it in the Facebook group or the WhatsApp app group, it sends this constant signal to everyone else of like, “Oh, we’re the type of community that invests in each other, that, um, like, shows up in meaningful ways, and then meets in person.”

[01:20:01] Like, lots of the praises are for, “Thank you to this person for hosting a great dinner- Hmm … in Washington, D.C. the other night,” or, “Thank you for this person for taking me to this, you know, ball game,” or, like, whatever else that it is. And, and so it’s this subtle thing. Like, as you’re just watching it, you’re like, “Oh,” you know.

[01:20:19] Like, “Oh, MMTers meet up in person.”

[01:20:22] Jayson: Yeah.

[01:20:22] Nathan: Right? Ben Greenfield wrote a praise for, like, “Thanks, Nathan, for having me on this, your podcast,” and like, “dinner on the farm” and all that. And it’s like, right, MMTers show up in person.

[01:20:31] Jayson: Yeah.

[01:20:31] Nathan: And, and so it’s just this constant, um, reminder that doesn’t have to… It, it, it’s entirely…

[01:20:37] You could say, “You know what’d be great this year that I’d love to encourage at MMT, is more people to meet up in person outside of the event.”

[01:20:43] Jayson: Mm-hmm.

[01:20:44] Nathan: And people would be like, “Oh yeah, that’s a good idea.”

[01:20:46] Jayson: Mm-hmm.

[01:20:46] Nathan: But it’s so different if the community is constantly like, “I met up with this person. It was amazing.”

[01:20:50] Yeah. And then, you know, you kind of flip back through your Rolodex of the event and go, “Oh, who do I wanna meet up with?” Or, “Who are the MMTers that I know in this city?” And it’s this flywheel that just keeps reinforcing.

[01:20:59] Jayson: The- you and your flywheels. I love them.

[01:21:01] Nathan: They’re always there.

[01:21:02] Jayson: Uh, if you don’t mind, I’d love to touch on two quick things- Yeah

[01:21:04] pertaining to the praise activity, which I think is really powerful. I think every event- Mm-hmm … in-person experience should have a praise activity like this. Um, and basically to what you said, uh, we use it as a reflection tool every day. Uh, it’s one of the first things we start with in the morning, saying, like, some variation of, like, reflecting on the last day.

[01:21:24] Share a… Think of a, a conversation you had. Maybe it was, you know, in the hallway, maybe it was at dinner, what have you. Um, but reflect on that, that interaction and write that person, like, a, a praise post. And it could be about the event. It could be like, “Hey, six months ago, this person showed up for me in a big way.”

[01:21:41] Mm-hmm. Uh, but we get everybody to process it by putting it on paper first. Uh, we have these cards. We usually get them to do two or three. Then we’ll get a couple people to share out loud, which is a, a important factor. Uh, and then we collect all these cards at the end of the event, and we’ll have well over 1,000 of these cards, which Candace then organizes them all and then mails them all out.

[01:21:59] Nathan: Yeah.

[01:21:59] Jayson: But she mails them 90 days later. Mm-hmm. And what happens is usually you’re on this high of an event, and then afterwards, uh, it’s, you’re back to normal w- Yeah … in your day-to-day life. To get this, like, surprise package 90 day l- uh, 90 days la- la- uh, later with, like, all these praises just brings you back.

[01:22:17] Um, and, like, the amount of times people end up doing another praise post in the community- … because they got the cards and they’re like, “I was going through a really rough day today, and, like, these… or really rough week, and these, like, really, like, you know, lift me up,” and that kind of stuff. And then from a community builder’s perspective, one of the cool things for me is getting to see who gets the most praise cards.

[01:22:37] Mm-hmm. ‘Cause it’s not always the most ex- extroverted people and that kind of stuff. Yeah. But those are ultimately, like, your culture carriers, and those are the people who drive the community. So as a result, you can be very top of mind that, like, m- I would say put golden handcuffs on them, but to, to some degree they really drive, you know, the value of the membership.

[01:22:54] Um, so that’s a, you know, a little behind-the-scenes insight which is really

[01:22:58] Nathan: valuable. When you, you get this data, ’cause there might be someone that you brought into the community and you’re like, “I think they’re gonna be a really good fit, but are they going to- Yeah … gel with everyone and all of that.

[01:23:05] Yeah. And then you look back and they get a whole bunch of praise cards, and you’re like-

[01:23:07] Jayson: Yeah …

[01:23:07] Nathan: like, it might be just be this open loop in the back of your mind- Yeah, yeah … as a community organizer, like, “I took a bit of a chance. Did it pay off?” And you’re like, “Oh, yeah, it paid off in a big way.” Amazing.

[01:23:16] Jayson: Well, I mean, and, and naturally you automatically often think that, like, again, the extroverted people.

[01:23:21] Mm-hmm. Uh, you, like, you feel drawn to them, and you’re like, “The, the community, they are the community,” when you realize that sometimes it’s oftentimes the more quiet people that, like, will have deeper conversations and meaningful conversations with people that really drive the experience. So- Mm-hmm … as somebody who’s constantly curating the community, that intel is just invaluable.

[01:23:39] Nathan: Yeah. I mean, that, that feedback loop is so powerful. But then I’m also thinking about from a marketing and business perspective, ’cause often these flywheels that you create are so simple, but then they have these byproducts, and one of the byproducts is if you ever want to do a talk or whatever else and ta- and say like, “Okay, what is the value of being in MMT?”

[01:23:57] Then you’re like, “Hmm, over the last decade, which of these thousand stories would I like to pull from?”

[01:24:02] Jayson: Yeah.

[01:24:02] Nathan: Because you made a system that tells not only you but everyone else- Yeah … about all the ones that people wanna volunteer.

[01:24:08] Jayson: Yeah. Never thought of that. That’s good.

[01:24:11] Nathan: And now you can combine

[01:24:12] Jayson: them all onto- That’s wh- this is act-

[01:24:13] secretly into one … this is actually, ladies and gentlemen, secretly a coaching session. Uh- Yeah,

[01:24:16] Nathan: exactly.

[01:24:17] Jayson: I appreciate that. That’s awesome.

[01:24:18] Nathan: Well, we’re gonna do a whole other episode on the book launch- Mm-hmm … and everything else, but one thing that we haven’t talked about yet and that we’ll just wrap up on is the title of the book, right?

[01:24:26] Everyone talks about entrepreneurs being self-made. Why did you, why did you call the book what you did?

[01:24:31] Jayson: Well, God knows I got flack for it. Uh, anytime you ask anybody for feedback on book titles, you’ll get feedback. Um, and it just muddies the water more than anything. But, um- You know, the, the, the stance of the book is challenging this notion of being self-made.

[01:24:48] Mm-hmm. It’s, it’s one of those things every time I hear the term, uh, I have, like, a reaction to it, and I just wanna, like, plant my flag in the sand that, like, that is the wrong approach. Because no matter what you strive to achieve in life, the fingerprints of others will always be on your journey. Um, and that doesn’t…

[01:25:07] Like, that could be if you have a company, it’s, like, your team. It’s, like, the people who mentors and people who’ve kinda facilitated connections and that kinda stuff. So the actual s- quick story, if you don’t mind- Yeah … of, like, how the term community made came about was in 2017, we hosted a gathering, and normally I open the gatherings by setting the container, like we talked about.

[01:25:29] So I usually do a talk and that kind of stuff. That year, we decided to do something different. We brought somebody on stage. They were sharing their story. Um, so this individual was doing fitness videos on YouTube and was a comedian and, uh, packaged everything in a book, and everybody was just hanging on every word.

[01:25:47] And at the end of this talk, uh, he said, “Unlike most of you, I can’t navigate the world without help. Um, and as a result, I’m not self-made, I’m community-made.” And that individual, his name is Zach Anner. Mm-hmm. And he has cerebral palsy, so he was on the s- the stage in a wheelchair. Um, and the reason I got him to open the event is so many entrepreneurs There’s a lot of entrepreneurs that don’t, or individuals that don’t focus on building relationships.

[01:26:17] Then there’s a small segment that understand relationships are important, so they build, uh, and invest heavily in relationships. Uh, but that’s only half the battle. You need to be willing to ask for help. And, um, having Zach as an example, to me, was going to really kinda set the tone. But when he said, “I’m not self-made, I’m community-made,” I was like, “I’m gonna go take that domain right now- Yep

[01:26:38] and give him credit wherever I can.” Yeah. Because it, uh, has done just such a beautiful job to, like, solidify, um, just the different position to, like, those who take the self-made stance. So, um, so the fact that he crystallized that into the term community-made, that naturally felt like the title, uh, for the book.

[01:26:58] And even through all the pushback I got at different stages, uh, I stuck with it. And now I feel, um, it’s the perfect title.

[01:27:05] Nathan: Oh, yeah. It’s so good.

[01:27:06] Jayson: Yeah.

[01:27:06] Nathan: Well, the book is Community Made: The Truth About Success and the Relationships That Create It. Jason, thank you so much for coming on.

[01:27:13] Jayson: Appreciate you, my man.

[01:27:15] Nathan: If Jason got you thinking about what makes people want to keep coming back to a community again and again, then I think you’re really gonna like episode 127 with Will Guidara and Brian Canlis. In fact, Jason’s the person who introduced me to Will. Will wrote the book Unreasonable Hospitality, which has sold millions of copies.

[01:27:33] And in the episode, we get into so much more than just hospitality in the episode. Like the video if you enjoyed it, hit Subscribe on YouTube or wherever you’re listening, and I’ll see you next week.

[00:00:00] (588) AI Can’t Copy This: Why Every Creator Needs an Origin Story in 2026 – YouTube
https://www.youtube.com/watch?v=lALLm8YRP3Y

Transcript:
(00:00) Sharing your story is not a burden. We use that as an excuse so we don’t have to share our story. [music] >> My guest today is Philip Mccernin, author of One Last Talk. He’s helped Olympians, World Cup athletes, and even consulted with the US Army [music] and the Pentagon. Philip explains that your origin story is your most compelling asset.
(00:18) The most compelling way to connect authentically with people and help them feel something in themselves is to share a part of our origin story. And a lot of us leave those origin stories behind, and I think that’s a mistake. Philip walks us through the soul set process which breaks down the overlap of story, gift, and impact. >> My experiences with creatives is that they don’t put a value in what they do naturally.
(00:38) They’re too busy trying to put a value in what they think the world wants from them. >> I have to share this with other people. I felt like I had discovered something incredible. Like, do you know this? You’ll see him do this exercise with me live, including a moment where he has me draw a picture of my ideal avatar. [music] >> Can we get a blank page? >> Yeah.
(00:53) I was having this hang-up where I needed to ask people for help with promoting my new book and I was feeling anxious because I do not want to be a burden on them. >> How selfish of you not to ask people for help because you are abandoning this poor man. How selfish of you. >> This is actually episode [music] 150 on the show and I couldn’t think of a better episode to celebrate this milestone with.
(01:12) >> There’s a saying that I say your greatest gift lies right next to your deepest wound. >> If you want to learn what it is you’re put on this earth to do, this is the best episode on the show to watch. Philip, welcome to the show. Thank you for having me. It’s basically impossible to describe what you do, but we’ve known each other for about eight years, and I think of you as someone that people come to when they need clarity.
(01:34) >> And we’re going to talk today about storytelling and how that matters so much as an entrepreneur. But let’s dive in right there. Why does knowing your story and and sharing your origin story matters so much as an entrepreneur? >> I think it matters on so many levels when it comes to parenting, comes to leadership, it comes to business.
(01:51) Um, if I may kick off with a story, I think that illustrates it best, is I was invited to be part of this Shark Tank Dragon’s Den uh, competition where entrepreneurs would come along, they’d pitch their business to three entrepreneurs at a table, and we would help critique their business, you know, pitch.
(02:09) And then the whole goal would be to get to the final. And if they got to the final, they get on the main stage, deliver their pitch one last time, and then they either win or they don’t. And if they were if they were picked and they’d win, they would get like, you know, injection of capital, they got marketing support, mentorship, etc. Anyway, this poor >> there’s a lot at stake.
(02:26) >> There’s a lot of stake and and this beautifully young man came up and he was petrified. He did this, he was shaking and it was his first time pitching and myself and two entrepreneurs to my right and he pitched his business and the first entrepreneur said, “Listen, I loved your pitch.
(02:40) I just loved to have seen a few more numbers to really get a sense of the business and the projections.” And he goes, “Oh, great.” And he’s making a note and she was very gracious. The next one said, “Love, love the pitch. Well done. And I just love to have seen more information on marketing and how you’re going to, you know, you know, put this out to the world and draw clients in.
(02:59) ” And then it came to me and I just looked at him and I said, “I don’t get it.” >> And this poor young man looked at me and said, “Uh, what part?” And I said, “The whole thing.” And he goes, “But but what what do you mean?” And I said, “Really? You want to build a gym and multiple gyms? Does the world really need another gym? And meanwhile, the two entrepreneurs were looking at me going, “Who is this ass?” Right? [laughter] >> But I could feel something.
(03:24) My my intuition was telling me there was a reason that he wanted to build a gym and create a franchise and bring this out to the world. And he looked at me and I said, “But why you?” And he goes, “Well, my personal story, you know, doesn’t matter.” And I said, “Well, it matters to me.” Mhm. >> And he paused for a moment and then he looked at me with this combination of sadness, anger and and possibility.
(03:50) And then finally he said, “My parents left when I was a baby. When I was a young boy and I grew up with my grandmother and she meant the world to me and when she passed away from a disease related to obesity, my life fell apart >> so badly that I went to prison.” And he with tears rolling down his face, Nathan, he goes, “And no one should lose somebody prematurely to something that can be prevented.
(04:21) ” >> I look over to my right and the first entrepreneur is just >> Yeah. >> just rolling. >> The next entrepreneur is crying. I didn’t start crying because I’d already been crying. And the guy himself was crying. And then he goes, “But you’re you’re you’re not you’re not suggesting that I bring that into my pitch.
(04:40) ” I went, “Oh, no. Don’t do that.” Like, why would you do that? It’s the only most compelling reason that you were on this mission. Why on earth would you bring that into your pitch? And I won’t tell you exactly the language I used. I said, “You’ll be an effing idiot.” He brought it into his pitch. He got to the final.
(04:58) And when he pitched his business next to the two entrepreneurs that were in the final alongside him, he was picked by every single judge. Some of the best >> best entrepreneurs that have ever come out of America were sitting there judging this man. And when they were asked, why did you all pick him? They all said in one form or another, he had the most compelling reason to start this business.
(05:20) >> And he won the competition outright. So that’s a practical example of why your origin story matters. And you may not think you have an origin story that is quite as dramatic like that, but we all have origin stories and a lot of us leave those origin stories behind. And I think that’s a mistake. >> I mean, it’s so clear to me how much that matters, especially because, you know, I do cry easily, but it’s one of the things, you know, I am like so emotionally invested in your retelling of his story, >> right? But especially for content
(05:48) creators, right? We are storytellers. we get up and we talk and and everyone listening has businesses where they tell stories and and often they’ll say, “Oh, no. I I tell the stories of the transformations I create in my clients or I do these other things.” It’s like, “Okay, but but why do you do it?” >> Yeah.
(06:03) >> And so to dig into that is so important. >> It is critical and there’s there’s always a reason and there’s always an opportunity to reorientate your business to connect it to the reason that you’re doing it. You didn’t just wake up and decide to be a creator one day. You were born a creator and you’ve become a creator and you’re creating something and there’s probably a meaning behind it that you have and you hold it secretly to yourself or you have an opportunity to share with the world and people there’s a saying and forgive me I can’t
(06:28) remember who came up with this beautiful saying and you may remember but people will forget what you do they’ll even forget what you say but they will never forget how you make them feel and I think the most compelling way to connect authentically with people and help them feel something in themselves is to share a part of our origin story >> to allow other people to see your humanity but also experience and feel theirs.
(06:50) >> Something that stands out to me that you said is why you, right? You’re saying this to that entrepreneur? >> And in every business there’s a dozen people that we could hire, a dozen different businesses, you know, brands we could buy from and all of that. And I think everyone is asking like, okay, but why you over everyone else? >> Maybe the first question is like why you, right? you know, and putting it back on you of uh what’s what’s your origin story that brings you to wanting to do this work? >> Yeah. I mean, I’ll I’ll give you the
(07:21) short version of it. And I think that the shortest version I can give you is is you there’s kind of there’s so many different nuances, but I remember sitting in classroom one day feeling incredibly isolated and lonely and a teacher looked at me and she said she she asked me to read and I’m dyslexic, so reading was a challenge.
(07:37) And and I said, “Miss, I I would rather not read.” And I was actually I remember being quite polite. I was actually quite a nice kid despite the rumors. And um she said, “Oh, another excuse.” And she looked at me and she said, “You know what? I don’t even know why you come in here.” And she pointed straight at my face.
(07:53) I don’t know why you bother coming to school. And then she went over to the window and she says, “You don’t do anything in here and you’re going to mean nothing out there.” Wow. And even like even as I say that, I can still feel the emotion because I absolutely believed every word that came out of her mouth.
(08:11) And I believed it for a very very very long time. And what I decided to do was I put on the burners, the jet burners, and I was going to make sure no matter what, I was going to prove her wrong. And the idea was I thought about meeting her on the street one day. And when I wasn’t successful, I didn’t want to bump into her.
(08:31) But when I started to have some success, I then I wanted to bump into her. And I wanted to take her that finger that she was pointing at me and I honestly wanted to flip the finger and you know what I wanted to do and and point it back at her and say f you look what I’ve done with my life until one day I remember waking up going it was one of the most beautiful moments and it was you know we say these things I woke up one day and and it’s never really one day but on this occasion it literally was one day and I woke up and I just
(08:58) asked myself a different question. what was going on in her life >> that she had to take me out or knock me to the ground or grind me into dust because that’s what it felt like at the time. So my origin story was a lot of isolation, a lot of loneliness and my mission if you like hidden is I want to eradicate loneliness for as many people as I can as I can before I die.
(09:20) And I do that through helping them connect to meaningful work that brings them alive, connecting to themselves, through their origin story so they understand who they are and why they’re on this planet and connecting to the people around them because I don’t think it’s about deepening relationships in the traditional sense.
(09:35) I think a lot of us struggle with relationships because we don’t allow people in. It’s not about going out and finding someone to love. It’s about allowing somebody to see you, all of you, and allowing them in. And to me, that is if I can do that and help people do that. Loneliness doesn’t have the oxygen and the place to actually survive.
(09:51) And to me, that’s why I’m on this earth and that’s my mission. >> Did it take you a long time to come to that realization like or was that early in your your journey as an entrepreneur? >> Nathan, I am incredibly slow. Incredibly slow. So, in a way, it took it feels like it took me a lifetime >> and I could have gotten there sooner, but in another way, as cliche as it might sound, I honestly think that it wouldn’t mean as much to me if I got there too soon.
(10:17) So I think I had to get there over a longer period of time. Um but no, I think I think it was a pretty slow process for me. >> Okay. So I want to fill in a few of these circles up on the board. >> Yeah. >> So Philip, the Dragon Sense story clearly shows like why sharing your story matters, but I feel like there’s so much more to it than just oh this is my origin story.
(10:35) Like what is this framework and and how do you dive into working through it? >> Yeah. So at the top it’s it’s your story which we we’ve touched on. Maybe what I’ll do is I’ll walk you through a real life example. You know, we’re in the middle of the World Cup right now. It’s coming to the end. It’s in the United States and and obviously in Mexico and Canada.
(10:54) And I’ll give you a a story from an athlete that I’ve I’ve worked with and gotten to know very very well. And it’s it’s a beautiful story because it just shows what’s possible for us. And I work with entrepreneurs and I work with with athletes as well. And the crossovers and really they’re the same the same thing. But a young man walked into a room not dissimilar to this.
(11:11) And uh I was work I’m working with a club in Colorado, professional uh MLS club. He sits down in front of me and he said um so yeah, nice to meet you. And I said, “Great. Why are you here?” And he said to my surprise, he said, “I want to know about entrepreneurship.” Now, this guy’s not at the end of his career like Messi.
(11:27) This guy is just starting out. He’s in his early 20s. And I’m thinking, you want to talk about entrepreneurship? And my intuition again was telling me, I got to call BS on this. And I said, “You want to talk about entrepreneurship because you’re interested in entrepreneurship, or you’re afraid that you can’t and will not quite make it as a soccer player.
(11:45) ” >> To which he kind of sat back and went, “Oh, that’s the way it works in this room. You’re actually going to challenge me, >> right?” >> And he said, “Well, look at my life right now. It’s not exactly going very well. I’ve just been bought, you know, from a different club where I was ostracized and sitting in the in the stands.
(12:02) I wasn’t even allowed to train with the team. I was bought brought to this club with promises of playing and I haven’t even got a minute and I’m not even on the bench and I’m not being picked. So, I’m keeping my options open. And I said, why don’t we forget about entrepreneurship and we just talk about football as we call it in Europe.
(12:16) And we did and we continue to talk about it. But I remember the the first thing he said to me is when I when I finally got him to let go of this entrepreneurship thing, he said, “Okay, great. Let’s let’s let’s do it your way. Where do we start?” and he thought I was going to talk about psychology or performance or watch some of his videos of him playing and I just said tell me your story and he goes yeah he says I started playing soccer when I was like eight and I well I went to this college and I said I’m not asking about what you’ve done I want
(12:46) to know who you are and he said to me you like you want me to start like when I was a kid I said yeah and he said well it was tough I grew up in a really poor neighborhood in in Philadelphia. I had, you know, you know, we were poor and and I racism to deal with and I had loneliness and I had all this different stuff.
(13:07) And we started to build this this this story and I started to get to know this young beautiful human being. And I eventually said to him, “What’s the dream?” And he said, “Well, now that I’m connecting with it, suppose the dream would be to in some way, shape or form in the future come back and help kids like myself in Philadelphia.” And I said,”Great.
(13:24) ” I said, “Why wait?” He goes, “What do you mean?” I said, “Why wait? they’re watching you now. >> So, he started to play football and the way I would interpret that is he started to play football with with a a reason to play >> more than just himself. >> He was thinking about once I achieve either my football career and aspirations or if that doesn’t work out, which is looking like it’s not going to work out, >> then I’m going to become an entrepreneur somehow I’m going to make money. Yeah.
(13:50) And then once I make money, I can go back and I can help >> eight-year-old me. Yeah. back in my hometown. >> And I honestly believe because the difference at that level between an athlete, one athlete and another, it’s it’s it’s minuscule. I mean, tactically and technically and and physically >> is an intuition and a freedom.
(14:09) And I think when when I work with entrepreneurs or athletes, it’s about helping them play with freedom is is the big one. >> But ultimately, his his short-term goal was to get to Europe, which he finally achieved. And he got to Europe. And that was like the pinnacle. That was the biggest.
(14:23) But I kept harping on about what’s the next one? What’s the next one? What’s the next one? And the next one was to play for his national team, the United States. But meanwhile, keep reminding him all of the time that people are watching. People are watching. People are watching. Not >> you’re having your impact right now. >> You’re having the impact.
(14:38) >> And um you know, that is the the power of of connecting with your story. Even the parts of your story which we’ll talk about later on that you don’t want to talk about, that you’re you’re ashamed of or you’re embarrassed by or they they’re painful. That’s fuel that can drive you in a really positive way.
(14:56) And he has gone on to do extraordinary things. The dream became playing for the national team. And I remember the day that he was picked to play for his the national team for the United States. And then it was announced that the World Cup was coming to America as one of the host nations.
(15:12) And the dream became, would that be a possibility? Like what if I what if I went to the World Cup in my own home country, >> right? >> And he was picked for the team. and they’re like, “What if I play and then what if I score?” >> Okay. >> And it was about 10 days ago, he scored his first international goal for the United States.
(15:30) When he scored, it was such a stunning goal by anybody’s standards, but he’s a defender, so he’s not like a a goal scorer. >> Yeah. That’s not the the group of people on the team that scored goals. when he scored, apart from going absolutely ballistic, myself jumping up and down and screaming, it just didn’t surprise me because this young man, he’s got his own spiritual beliefs and things like that, which I won’t get into right now, but he just he’s playing for it.
(15:53) He’s just playing for something that sits just beyond who he is. >> And therefore, I think he possesses something that a lot of other people just don’t. And I think that’s available to all of us. What what’s the contrast from when you saw him play when he was sitting across the table from you in a room to who you saw score a goal in the World Cup? Playing with purpose.
(16:15) >> He’s playing he’s on a he’s on a he’s on a mission but but not frenetic. He’s not he’s not burning bridges and burning burning his life to get to something. It’s not like this insatiable drive. It’s a calmness with a it’s actually a knowing. >> Okay. It’s a sense of knowing I’m good enough. I can do this. I will do this.
(16:37) >> And I think that comes from just a deep sense of trust, which a lot of in my experience, a lot of creatives and a lot of entrepreneurs that I meet, they don’t really back themselves. They’ll back themselves intellectually, but emotionally they just don’t trust who they are. But his story has created the fuel >> for so much of his surface success, but it’s it’s much more than that.
(16:58) >> Okay. So to complete this this framework here, what else do I write in here? >> Yeah, so we’ve got story up here which is kind of the the top which is the key and then we have gift in here. >> Okay, what do you mean by gift? >> Well, I mean a lot of people would write down talent and I think for many people I I believe the the example I use is my wife because technically she’s not here so I can kind of use her story.
(17:20) Uh but my wife was an accountant and she is the worst accountant in the world simply because not because she doesn’t understand spreadsheets and not because she doesn’t understand numbers but because she was never put on this planet to be an accountant. Like trust me that was just not her thing. If you understand her origin story you realize that she grew up in a pretty poor you know background.
(17:40) She wanted to escape where she was living. And I don’t [clears throat] mean that in a negative way towards her family but she wanted to get out of this rural environment. >> You know her sister was an accountant and she was pretty decent with numbers. So you know she added it together and you know accountants get paid well. So your origin story can drive you in a really positive way or it can drive you to achieve things that ultimately won’t work and they won’t matter in the future.
(18:01) So the gift the difference between a talent and a gift is talent is something that can be learned like the soccer player like the young man we’re speaking about. But the gift you know there’s a saying that I say your greatest gift lies right next to your deepest wound. And his wound was and my wound was loneliness.
(18:17) his wound was, you know, poverty, judgment, or whatever. But through the lens of shining a light on his story, the gift that emerged for him is his ability to affect change in people similar to him in environments that he was stuck in. So they can believe if he can get out, I can get >> if he can do something with his life, perhaps I can too.
(18:37) So I think a lot of us spend our lives executing our talents and never honoring our gifts. >> And to me, I think that’s a tragedy. So he started to get in touch with this gift through the lens of some awkward conversations. And that’s where purpose starts to come in. That’s where aligning who you are and what you do every day towards something.
(18:55) And then realizing that we’re all stewards of something. >> We’re stewards of something. Like we bought a medieval castle on the west coast of Ireland, random thing as as it is. And people go, “What’s it like to own a castle?” And I don’t feel like we own a castle. I feel that we are stewards of a place for a very short space of time.
(19:14) And that energy, it feels so beautiful. It feels so abundant. So he feels that he’s a steward of the talent that he has and he’s created with the giftedness that he also has inside of him and to use that for good. You brought up a quote which is in your book uh one last talk and it’s the quote that you have on the inside cover which is your greatest gift lies next to your deepest wound and this is a quote that I have thought about really a lot in my life and it it took me through a lot of times of trying to find purpose.
(19:41) Why do I do what I do? And coming back to my story, I realized, you know, a lot of entrepreneurs have this of like growing up in an environment where >> money is very scarce. And and my biggest thing is I always felt like it was a burden on other people. >> And so when I learned that making money is a skill or a collection of skills that can be learned, it was like this incredible unlock. And I was like, “Oh, wow.
(20:02) I can, >> you know, I have to share this with other people.” I felt like I had discovered something incredible. I was like, “Do you know this?” And then you know when you learn about how an audience can give you this incredible leverage that like I just became so so excited. >> But in order to find it I like it was that quote of you know what your greatest gift lies next to your deepest wound.
(20:23) And it was all of the the pain from childhood of just feeling like oh man if I wasn’t here then my family could afford these things. They could have these different experiences that sort of like I am just a burden. And I think old me would have run away from that and hidden and not even ever uncovered that. >> Yeah. >> Um but really in digging it out then as you know you said like the purpose and alignment.
(20:42) >> Um and even the stewardship right something where I feel like so many of the ideas in my life and work it’s like they’re not even mine. I’m just a I’m just a steward of you know and that’s how I feel about you know people would say oh when are you going to sell the company? I’m like I don’t there’s an element of me that I don’t even feel like it’s mine to sell.
(21:02) I’m just like a steward of the impact that we have with it for this period of time. >> Well, it’s clear to me that you’ve clearly done work. How you’ve done the work, where you’ve done the work, whether it’s self-directed or otherwise is it’s not relevant for today, but but I could have sent you because there’s a there’s an energy that you talk about your background that it’s integrated and I often find that >> people are either in reaction to their past or in relationship to it.
(21:25) And I work with a lot of entrepreneurs who just are d they’ve come from poverty. I’ve worked with athletes who come from poverty. >> Y >> and there is no greater drive than the fear of going back. >> Right. >> But what I would say there’s a caveat to a point. So running from what you don’t want is great.
(21:44) But here’s the absolute reality of it is that that energy runs out. >> That energy takes too much from you. That energy is exhausting. and that there is a point in life where you can just pause and say, “Okay, I’ve outrun the monster, the fear of going back to poverty, whatever it is. How do I reorientate towards something that I want to build?” And that is one of the most courageous moments in an entrepreneur’s or creative journey is to stop out running what you don’t want and moving towards what you do want.
(22:14) And the way I would contextualize that is you’re running on diesel fuels >> or diesel fuel. And you the idea is to run to move to hybrid and then to move on to electric, a cleaner fuel. And that the the the reason that most people don’t make that transition when I get close to their origin story and we start working on this is they go don’t take my story away.
(22:35) You’re not don’t get near my story. This story has driven me. Look at all the data. Look what I’ve created in my life. >> It served me very very well. It served me beautifully. If you take this away, you’re taking away my drive. And in my experience, it is the opposite. >> When you start to orientate towards something that’s cleaner, pure, you play with freedom as a soccer player, you play with freedom as an entrepreneur, you play with freedom as a parent, and you start making decisions that feel truly and deeply aligned to who you are.
(23:08) And you become unapologetic as a leader. and you become deeply deeply focused and invariably in my experience is impact starts to creep in in a different way. >> So it’s the opposite of what mo most people think >> and that’s that the last circle there is impact >> is impact. [clears throat] >> There’s something I’ll write this and then talk about it.
(23:31) Uh there’s a freedom with it that I think sometimes scares me and uh scares people on my team if I’m being honest. So, we’re in a a period of massive change, right, with AI and every every business and industry is being shaken up in a big way. People have said it’s like the industrial revolution times the invention of the internet like happening right now.
(23:52) And so, we’re watching new businesses spring up and and just as many die off and cease to exist. >> And so, there’s an incredible amount of fear around it. And I had conversations with a few people on my team and they’re like, you’re not you don’t seem afraid at all. And what I and so we’ve had a lot of conversations about it and part of it is I feel like we have a really clear plan >> for we’re very clear on what the impact we’re going to have in the world and how our adoption of AI is going to further that.
(24:19) >> But I had this realization through these conversations that it could all disappear and I would be just fine. Like I actually don’t fear going back >> because I know that even if you know a company doing tens of millions of dollars a year in revenue like disappeared overnight, I don’t think I’d have any regrets over not selling it or not taking money out or that sort of thing.
(24:44) Like I I know at a basic level >> I know that my family is taken care of, but I know that building the company is not my work. My work is helping creators earn a living and no longer be a burden and showing them that there’s these skills and tools out there. And I know that if my current vessel for that disappears, >> yeah, >> there will be another one.
(25:01) >> So that’s the key. There will be another vessel. There’ll be another way to do the same thing where I think a lot of people and that’s why I said why not? Why are you not afraid? >> Why are you not afraid? And a lot of people watching this listening to this in the future might make make an assumption.
(25:17) and we go, “Oh, well, it’s easy for you to say you’ve got millions in the bank. You’ve this, this, and this.” I don’t. People have said to me, “Oh, it’s easy for you to do what you do.” I started doing this work when I had $200 in the bank account. We were completely and utterly wiped out and we were underwater to hundreds of thousands of euros.
(25:32) And I decided to start a business in a foreign country in Canada. And we bought a medieval castle when the middle of COVID when our business just slightly affected. It was only down 95%. >> Only only that >> only 95%. And we have a very modest boutique coaching business. And but what you’re sharing there is so so beautiful and so fascinating that even if this is taken away your identity is not locked and attached to it which most of us get suck sucked into that piece.
(25:59) Could you just elaborate a little bit more if you don’t mind because what you’re sharing you’re sharing it so simply but I think it’s so profound. It’s more profound than anything I’ll share here today genuinely. How do you how have you gotten to a point where there’s you care but you’re detached to some extent that if this goes away which it most likely won’t because you have a plan and you know the impact you’re going to make but there’s going to be another vessel like how do you get to that place? What have you what process what how how do you think like that?
(26:23) Well, I think if you go back to more things as a kid, uh, a like recurring nightmare that I had as a kid was always seeing myself in third person, like from an altitude in some way and then bad things happening in some way. You know, it could be like chased by a wild animal or whatever, but that was always the format of the nightmares that I had.
(26:44) >> And to the point where I would, you know, if I sense like starting to view things from a a third party lens, that was scary. I had to be in it otherwise it was a scary thing. Now I feel like I can like that is a tool that I can use and I can >> step outside of whatever is happening and observe it from the third party and go oh however that plays out like >> I I don’t know exactly how to describe it but it it um detached is the wrong word >> but it’s very much it’s like a different altitude and so the thing that I feel is
(27:18) like being able to play with this relaxed feeling and uh I heard Jason Freed talk about this of like when he was learning to play the drums, he’s gripping the drumsticks and his instructor’s like, “You’re never going to be good until you learn to hold them loosely.” Now, I struggle with this all the time >> where I end up in this other world where it’s easy to fall into the oh, if we do this and a competitor does it better and what if we don’t win this customer and you know, you’re in a competitive landscape and all of that and I have to
(27:49) keep reminding myself like that’s okay. Actually, I think the clearest example of this is is actually Elon Musk >> where he which as far as clean fuel, dirty fuel, like you get into a whole thing of how he fuels himself as an entrepreneur and I I don’t think a lot of it is healthy, but something that he says he’s like, “Look, our mission is around clean energy, around electric cars, around all this.
(28:14) ” People like, “What if Toyota or Mercedes comes in and does this?” And he’s like, “Okay, they’re just furthering our mission.” you know, he’s like, “We don’t have patents for anything, you know, like it’s all open source.” >> And so, I try to stay in this place, and I’m not always there >> of when uh a content creator that we serve is on our platform versus someone else’s to be able to say whatever makes them most successful.
(28:38) >> And so long as they’re if they’re really really successful on a competitor, that’s great. Like, that competitor is helping us achieve our mission. And that’s what I I want to come back to in a minute. Before I do, >> what you’re describing to me as I as I stand here listening to you. >> Um, and it’s not, you’re right, it’s not detached because detach makes it feel and sound like you just don’t care where it’s actually the opposite.
(29:02) You care deeply and you care enough, but it’s almost like you hold it. So there’s this there’s this there was I think it was a therapist showed me this the first time. I can’t remember, but this is as AI comes into the world, this what it feels like. It’s like, hold on tight. Grip as tight as you can.
(29:18) No matter what, we’re going to burst through this and we’re going to just as as AI comes into the world, we’re going to double down and we’re going to And as I hold that, imagine that’s a seed or whatever. Yeah, you might get some moisture in there, but there’s no light. And what most people think is when they when we ask them to to to let go is they think like this.
(29:34) Well, I need to I need to let it go. And what I’m thinking is no, it’s like this. >> You hold what you do in your hand. You hold the possibility, but you let go of the grip and the tightness attached to it, which is back to the drumsticks as you talked about. Yeah. And I think about I don’t know if it’s a timeline or how you would express it, but you know, if you think about I don’t know there’s there’s uh this line here and it’s like we have a customer and they’re right here and our product is going to get them to here, right? And we’re trying to achieve this goal and it
(30:05) really matters that we win the sale and this happens. But we can forget about the fact that the goal is to make it like somewhere along here is the goal of not helping this customer but helping creators earn a living and helping anybody that we could serve, right? And then if you go even further, the goal is making sure that you know the the equivalent of the the kid back in Philadelphia, right? Or in my case the you know the 10-year-old up at living up in the mountains watching his parents fight about money again. like that he
(30:37) [snorts] feels like he’s not a burden. And so then you start to think, you know what, if like I’m very attached to I’m gonna help this person in this way and all of that. Yeah. And if someone else is like, “No, we’re actually helping this person over here.” And then it ultimately gets it’s like I don’t have to be the one to achieve that for people.
(30:56) uh if I get to that’s a huge privilege but it’s it’s zooming out at a different altitude and seeing it for the big picture instead of the very specific outcome of like did we win this deal or >> um build this feature or something. >> What would a 10-year-old back then think about who you are today? Oh, he’d be he’d be blown away.
(31:16) Like he would not I mean there are so many days you we we can get into this later but right the happiest days are all the number of times now that I go I cannot believe my life >> is just wild. >> Yeah. Before we get on to and we’re going to be moving on to this but I think a lot of us struggle with that. Um and and I’m I’m guilty with this.
(31:34) I’m not great at stopping and appreciating but so the last couple of days you know we’re we’re in Boise, Idaho. >> Um I’m staying with you. I was in the gym with you this morning and your son. >> Uh last week I was um Mike Reed and Daniel Priestley invited me into their organization to work uh with a with a big cohort of people on their origin story.
(31:57) And then in between I’m driving through the mountains of Montana in Yellow Knife and then I’m here and you know I just I I found myself on occasion just driving through the mountains just smiling going is this the life that I get to live and have created and everything else. And I look back and I think about my 10-year-old often. Um, I used to because I would have thought it was just fluff and but I think about my 10-year-old often and the particularly the young boy that was pointed out in the classroom and the teacher that, you know, made me feel
(32:22) like I was a piece of and I was worth nothing and would amount to nothing. I’m thinking, you know what, I’ve done okay. I’ve done okay. >> Yeah. >> How important is it for you to be clear with all the changes that are happening? Because you said earlier on, we’re really clear on the impact we want to make.
(32:39) I don’t need to necessarily hear what the details are, unless you want to share parts of it, but how important is that to have that as a north star to orientate towards that amongst all of the changes that’s going on? >> I think it’s incredibly important. And every time I lose sight of this and I start to to think about a short-term timeline, >> yeah, >> then I get stressed, I get anxious, I start to grip the drumsticks and I’m like, “Okay, what if this happens? What if someone invents a better way of achieving this goal than we do?” And, you know, and all of that. And uh it’s
(33:08) not that I want my business business to disappear in any way, you know, but that gets me, you know, okay, talking about kids, uh my oldest is 14 and a half. And in Idaho, you get to get your driver’s permit at 14 and a half, which is wild. >> That’s scary. [laughter] >> Okay, so he has his permit.
(33:28) He’s driving now. He’s actually like really a good driver. I’m quite impressed. But one of the things that you have to work with all new drivers on is they want to stay in the lanes, right? And so they look right here in front of the car. >> Yeah. >> Right. They’re looking at the next deal they’re trying to close or whatever else.
(33:44) And what happens when you do that is you’re like doing this and it’s terrifying as a passenger because you’re like, >> “Okay, I need you to look way down the road. I need you to look as far as you can see down the road practically, you know? I need you to look through the curves. Don’t look at the curve.” Like you’re going to drive right into a barrier if you do that.
(34:00) like I need you to look through the curves. And so I think that being really clear on these things, your story, your gift, and then ultimately your impact, why you’re doing it, is what allows you to look far down the road, see through the curves, and as things come up, you’re like, >> you can start to you have a different perspective.
(34:18) You can start to see, >> oh, that is something that I I need to address in the process of where we’re going, or like that’s not even going to matter. Like, >> we’re driving 50 miles an hour. That’s I’m not even going to think about that again in about three seconds. Yeah. Um, it’s going to pass right back. >> What’s coming up for me is is about about seven years ago, we came across this medieval castle in Ireland in an area I’ve been running retreats in for forever.
(34:41) And this little castle buried in the mountain which has the most extraordinary origin story, which it maybe is not for today. Um, became came up for sale and it was the middle of co our business was down 95% and I looked at it online and I shut down the computer and said that’s ridiculous. And then I looked at it again. I said that’s ridiculous.
(34:56) And then about a month later, I opened it up and I called my wife and she walked into the room and I said, “Can you imagine?” And I turned my laptop towards her and instantaneous she said, “Yeah.” [laughter] And long story short, we flew back to Ireland. We had our masks on. We walked into the castle. There was rats and bats and mold and and everything.
(35:14) It was just horrendous. The grounds were in bits. And uh we just I made an offer. I just it was instantaneous. I had to make an offer. And I didn’t know how I was going to figure it out and now I was going to pay for it and I knew it was going to take a ton of time and a ton of energy and if you want to lean over and touch my soft hands these hands had never seen a hard day’s labor in their life.
(35:32) So I have no idea what to do but I became obsessed with creating a safe place for people to come from all over the world to heal to grow and to go back out into the world and make the biggest impact they can make in the world. And I remember one of the greatest moments of doubt and there were there were many but there was a moment of doubt and I have a a kind of slogan if you want to call it be brave you matter.
(35:54) And I think cou courageousness, I think being courageous is one of the most beautiful things that we can give our children or inspire our children to believe. I think courage is the gateway to clarity. It’s not clarity and then courage. It’s courage always first. And I remember looking at my now 14, 15year-old, which I can’t imagine her driving by the way, not no disrespect to her [laughter] if she listens to this or watches.
(36:14) Um, but I remember her looking and she said, “Daddy, you okay?” And I said, “Maggie, I’m really I just don’t know if I can complete this project. I just I’m so out of my depth.” and she would have been probably 11. And she said, “Dad, is this place going to be important to people?” >> And I said, “Yeah.
(36:30) ” And then she looked me in the eyes. She said, “Dad, be brave. This matters.” [laughter] And I just started crying. And I stood up and I said, I said, “It does, and it will, and we’re going to finish this off.” And it took us six years to restore this place. But because it was for other people, that’s what that’s what drove me every day.
(36:55) And when I tried to impart my vision of what this place needed to be onto it too deep, like too aggressively, >> the castle and the grounds would push back and say, “No, thank you very much.” But when we would stand back and go, “What do you need to create this as the most beautiful place in the world for people to come and grow and for leaders to come and grow?” And then we would just get ideas and people say to me, “God, you’re so amazing.
(37:16) Look what you’ve done.” I go, “I’d love to take credit, but honestly, I think this place was guiding us.” >> Yeah. And that’s an example of like in the timeline, >> right? If you’re thinking about, okay, how are we going to get this done? What decision do I make right here? But then if you’re just thinking about, okay, how is this these grounds, this castle, the thing that we’re creating going to serve people? And then like >> let it come from there.
(37:37) >> Yeah, totally. >> Now, you have these other you have overlaps in the circles. Yeah, >> let’s talk about that. Really the the the this is really about self. This is about you as an individual. Um and this is about you know the work that we do in the world >> and this is about others. This is about relationships essentially.
(38:00) This is about the relationship to yourself. And I think a lot of us forget that. I believe leaving you know spirituality aside even though I think you know relationships are very spiritual by nature. I think the relationship with ourselves. A lot of entrepreneurs don’t really like who they are.
(38:15) Um they’re very harsh on themselves. They punish themselves. They berate themselves. And again, they have this narrative that that pushes them to get them so far. And I would argue that it’ll get you so far. But I think to build a healthy relationship where you’re comfortable in your own skin, that you can sit in the car without the radio on, that you can be on your own and eat in a restaurant without feeling awkward, I think, is a representation of a journey to build a relationship with yourself. That’s important.
(38:37) And then the invitation is to bring your gift into the into the essentially into the work you do and create an impact. And I think that’s the holy grail for a lot of people is that how do you do work in the world that makes an impact and rather than waiting like this adult or sorry excuse me this this athlete did how do you bring this in sooner to bring impact into your work every single day.
(38:56) And I think when when you have a bad day in my experience when you have a bad day a bad week or a bad month or even a bad year you’ve got to be able to access a deeper well. You’ve got to be able to access something that that is deeper and beyond you. And I think for me is that when you the work you do in the world has impact buried into it, you’re actually doing it for somebody else.
(39:15) >> I’m not very good at asking for help, but when we built, you know, an orphanage in Peru many years ago, I was the best asker on the on the planet for about six months until we raised the money we needed and then we built it. So you you want if I if I was to ask for somebody else, no problem.
(39:32) as long as I believe in the mission. But to ask for me, it’s really really difficult. The same principle applies is that building impact in really gives us an opportunity to dig into something else and to and to to drive and to move through difficult situations um and access some sort of, you know, momentum. >> I’m glad that you brought that up because something that I’m working on right now is I have my first book that I’ve written in more than a decade coming out in six months.
(39:55) And so I’m at this place where as an author, you need to ask for help, >> right? And I have lots of friends, you know, who would love to help. And I feel really, really awkward about asking. It feels like I’m asking for a favor and all this. Like, will you help promote your book, my book? Can I come on your podcast? You know, any of those things.
(40:12) And I’m just like, >> each time I think about it, I cringe. I’m like, what if they think of me as needy? What if they think about me as taking? What if they think about me >> as a burden? >> Yeah. >> And I’m like, oh, >> which which comes back to comes back to the story, you know, you’re just like, >> oo, nope. Can’t do that. Can’t do that.
(40:29) And I had a friend who I was talking through this with and he said okay well why’d you write the book? Did you write it for you? And I was like no I know these things you know and I I wrote it because I deeply believe in the impact that this book will have and how you know the book is the ladders of wealth how to master the skill of making money and that because money is the goal.
(40:49) It’s because this freedom is the goal and and this feeling of like oh I can actually achieve what I want to achieve and I’m trying to give people that roadmap. M >> and he was like, “So, are you asking for you or are you asking for someone else?” >> Like, “Oh, okay. I’m asking for their help in order to help, like in order to have this impact on the world.
(41:08) ” And it completely reframed everything. I went from a spreadsheet of people I knew, I had relationships with that gave me anxiety. I would look at that and be like, “Okay, I hope this doesn’t feel like calling in a favor or asking or they don’t think of me as a burden to, oh man, what a privilege.” >> Yeah.
(41:25) that I get to bring my friends along in this thing that I think is wildly important. >> There was a beautiful [clears throat] clip of Gene Hackman, the actor. >> Yeah. >> And someone asked him a question about his father leaving and his father left in this really unusual way where his father got in the car, drove down the road, waved to him or gave him a nod and then just drove and he was gone.
(41:47) >> He never saw him again. And Gina Hackman was asked this question. It’s his most beautiful he was an incredible actor in my opinion but just beautiful moment tender tender moment and he just connected with this the interviewer asked him about this moment that his dad waved or acknowledged him and then disappeared and Jean just starts breaking down and then he just lifts himself up and he says it’s only been 65 years you know and everyone laughed or whatever but I I bring that up because again the sense of being a burden keeps
(42:14) reemerging it doesn’t go away >> and that’s the problem people say oh no I’ve done I’ve dealt with my story I did six therapy sessions I wrote a letter to forgive somebody and I’m done. And it doesn’t. It never goes away. It’s how do you learn to integrate something and journey with the pain, not to try to run from the pain.
(42:33) >> I’d love to do something with you. Okay. >> Can we get a blank page? >> Yeah. >> So, with the anxiousness of asking, let’s just say that the anxiousness and the sense of being a burden was a 10 and then your friend help you reframe it. >> How far down on a scale of 1 to 10 has the has the scale dropped? Uh, 5.5.
(42:51) >> 5.5. So, we’re at four and a half. [laughter] Okay. >> No, I was thinking we’re at 5.5, right? >> Oh, yeah. 5 5.5. Okay. So, let’s let’s imagine that we could drop that even further. >> Okay. >> How many more interviews? How many more email lists? How many more people could help you? And I’ve got an exercise with you that I would love people to to play with.
(43:09) >> So, again, this is not rehearsed. We hadn’t planned this. I definitely hadn’t planned this, but we’re going to have a go. I want you to imagine somebody who is struggling in life. Okay, but it’s a it’s a fictional character. It’s not a real person. It’s not your like your family member.
(43:27) It’s not a friend, a buddy. I want you just to kind of think like just connect with the world and just think about and connect as best you can. We’re doing this in real time, so it’s not going to be perfect, but I want and I want you when you’re ready, I want you to begin to draw that person. I don’t want you to get write any words or numbers. I just want you to draw.
(43:44) And this is going to be a stick figure. It’s not about apologizing about your art. I just want you to draw this person. This is a human being that is somewhere in the world. You have not met them yet, but they’re struggling in one form or another. >> Can you just start just start drawing? This is either going to work really well or it’s going to go south. I don’t know.
(44:11) >> So, this is your person here? >> Yeah. >> Give them give them hair. Give them. Are they a man or a woman? Uh, >> they’re a man. Guess they’re >> They have kids. >> Uh, no. No, they’re not very happy. >> Give them a Give them a name. >> Uh, the name is Andy. >> Okay. How old is Andy? >> 20. >> And what is Andy struggling with right now? >> He’s on the outside.
(44:40) >> Outside of whom? >> Community. Uh I mean it drew other people. >> Yeah. >> Cuz he suffer from that. He’s sitting and he’s watching from a distance. >> Okay. >> And >> so what does he feel? What is he feeling? >> He feels uh alone and lost. >> Alone and lost. >> Mhm. >> Okay. Anything else? >> I think hopeful. >> So there is some hope.
(45:08) >> There’s something there. >> Yeah. >> Yeah. There’s a little bit of um hope and like determined. >> Yeah. >> What’s inside as in what what gift if we go back to the the analogy of here? We don’t want to get into a story necessarily, but what gift might he have that he’s unaware of? He maybe has a sense of it, but he’s not entirely sure what it is.
(45:32) >> Yeah. Like a an capability or a purpose or being meant for more. Okay. >> Capable of more. >> So, a sense of being destined for more, capable of more, um, but just not knowing maybe how to get there. >> Yeah. >> Okay. Does this relate to you at all? I >> think so. Yeah. >> Okay.
(45:52) So, so I would invite people to do if if you’re watching this, it’s pretty self-explanatory what’s emerging. If you’re not watching this, Nathan has drawn a a person sitting on a chair um, and has written down the words and so on and so forth. And this person is is on the outside of of the community, so to speak, etc. And I’m just curious your book.
(46:11) >> How could your book help Andy? >> Yeah. I mean, I think about a lot of the people that I’m trying to reach would be someone who I’m not trying to convince anyone to build wealth or um >> but let’s just stick to Andy. Forget about people just for a moment. Just stick how can you how can your book and your message in the book maybe not every every chapter, every every word, but how could your book specifically help and >> just give them the path and the road map? >> Oh, just the path. Oh, sorry.
(46:37) Just the path and the road map. Oh, that was gonna be something more profound to be honest with you. Can you write road map and and and and the path and the road map? And can you write the word just because that’s really relevant here? [laughter] >> Can I now? >> H. No, no, no. You’re not you’re not ready to do that yet.
(46:55) You haven’t done the word. [laughter] So, here’s here’s a really interesting thing, and this is where either one, the podcast is never produced, [laughter] I never edited, and it never sees the light of day, and even if it does, I’m never coming back. I can guarantee you that. And my family have to move out of the house tonight because we’re >> Is how selfish of you not to ask people for help.
(47:16) >> Because you are abandoning this poor man. >> Yeah. >> How selfish of you. [laughter] You are abandoning this man. And what’s also fascinating, if I may be a real >> is when when it comes to the things that we are about to gift the world of or give to the world, we use increasingly diminishing language.
(47:37) And yes, it’s just a word, but it’s not just a word. It’s the word just. >> I’m just a mom. Good God. >> Yeah. >> I I brought a human into this world. I carried them for for for nine months and I and I brought them into this world and I’m just a mother. We use diminishing increasingly diminishing language to describe the things that we do so naturally.
(48:04) And one of the challenges I my experience is with creatives which I know you serve a lot of is that they don’t put a value in what they do naturally. They’re too busy trying to put a value in what they think the world wants from them. what the world wants from them is the thing that they do most naturally, but we don’t put a value on that.
(48:21) When I was my mother met a group of my clients once. I said, ‘What do you think of what your son does? And she goes, I have no idea. He’s a coach. She goes, what’s that? He’s a speaker. She says, “What do you mean he speaks? What does he speak about?” She goes, she said, “But what do you mean?” And and one of them just said, “He sits down with people and he asks them really simple, challenging questions.
(48:38) He listens deeply. He doesn’t even listen. He hears them and he sees what’s possible for them.” Ah, he’s been doing that his whole life. [laughter] When I was 12, I was doing this work. >> People would come to me with all their challenges. Do you think I honor that? You think I honored the 12-year-old? No. I spent the next 30 years running around the world trying to make money because my story was when I make enough money, then I’ll give myself the freedom to go what I want and and do what I want to do. So, here’s my challenge to you and
(49:07) anyone else who’s watching this is do this. Create this little avatar. I think an avatar is even too cold a word to use to describe Andy because it’s so much more depth to it. And then ask yourself when you were afraid to produce that podcast, when you were afraid to deliver that talk, when you were afraid to take up that little camera and record a video and share a message, here’s the question you ask yourself.
(49:30) Am I turning my back on Andy? >> Am I turning Am I abandoning Andy or am I serving him? And that detachment, sorry, it’s not detachment, but that separation, there’s that moment of separation allows you to make a decision so you can be brave because what you’re going to say matters. And it may not matter to you, but it matters to him.
(49:50) And there are millions of Andes all over the world that you don’t you haven’t even met yet. So my my my invitation is stop being selfish because it’s not about you and make it print this off and put this on your desk. Look at this image >> and then make the call. Look at this image and send the email.
(50:07) Look at this image and put it in. Put your book out into the world because your book now he can draw a line through adjust. Your book will show Andy the path and the road map. The thing that stands out to me so much is you asked about the our scale, right? The uh you know the anxiety of you know we’re at a 10 versus a one of making that ask >> and you know thinking about the impact and all of that.
(50:34) You know, I said you got me under like a 5.5, something in that. That’s where we’re hanging out on the scale because I’m thinking about this reframe of what is selfish, right? Because if there was a a selfishness scale or maybe it’s a teeter totter or a seaside, I don’t know what the the analogy is, but I think where I got to was back to neutral >> where like, oh, because the the self-promotion of promoting my book and my ideas and all of that because it’s about impact, it’s not a bad thing and maybe even it’s a good thing, but in
(51:12) what you’re saying, what I hear is it tips the other way. Yes. >> Where it’s like it would be selfish not to. >> Absolutely. 100%. >> And that’s such a huge difference, right? >> Yeah. >> And so, yeah, I’m going to write that down. [laughter] >> It would be selfish not to ask. >> 100%. >> Okay.
(51:31) If we go back to the entrepreneur on Dragonstone, >> right? He wants to build his gym. He has his goals. He has his short-term financial goals he’s trying to achieve. He has these other things. He’s like, “Should I go? Should I pitch? If I were to pitch, I’m taking up space. I’m doing this thing. Maybe I’m taking a spot that another entrepreneur could have.
(51:50) Is my ideas is it worthy of the time or all of that? And those are all like I think very valid questions when you’re focused around the short-term outcomes. >> Yes. >> But then when you go all the way to like, okay, what is your story? What is your gift? And how do you bring that impact through to the world? Then >> you know some he’s like ah should I go on dragons then or not? Like it would be selfish not to.
(52:12) >> Absolutely. The the way I often think about evolution for people and and definitely my own evolution and is the idea of mountains. I’m a big mountain analogy guy. I love mountains. I love hiking and I’ve been using it forever. And mountain one is is really about was all about me. It was all about Philip Mccernin.
(52:31) And then mountain two was about us. It was about, you know, creating a family and and and and and building something with a team. And a lot of entrepreneurs get get stuck on that second mountain. they just they they overstay their welcome often. And then mountain three is about them is about how do I impact the world? It’s almost suspending a little bit of my self-interest or redirecting my self-interest and saying how do I make the rest of my life about other people about the impact that I want to make.
(52:54) How do I help the Andes of the world? And while I like you talked about earlier on that you oscillate in and out sometimes of these of this you know connected sense and senses trust when I’m in that them sense it’s almost like and it sounds so arrogant. It’s almost like everything I put my hand to seems to kind of work.
(53:14) There’s an effortless or it just feels effortless and then it feels simple. And then when I get scarce and I come back into the kind of the me and us energy, things become arduous again. And as soon as I put myself back into the them energy, it is it is unbelievable the shift that happens and the sense of courage that emerges in my body because it’s not about me anymore.
(53:34) I’m thinking about um sports again and thinking about the the player that you were coaching and working with and you know we just watched a uh a World Cup game and we’re talking about you know the flopping that happens or you know it’s always entertaining to see something happen and not get called and then like seven players come over to the ref and and it’s amazing that they’re allowed to >> yell at the ref as much as they do and you know sometimes there’s a card for it or whatever but there’s like you see teams
(54:04) play to win. You see teams play to not lose and you can see like those dynamics change so much. And I’m imagining if you were playing just to play and so you’re in the game and the flow of the moment and what you’re imagining is you think about, okay, how do I want to show up for the kid in Philadelphia who’s watching? Am I going to be go yell at the ref the fact that my ankle got clipped and he didn’t get a No, I’m not going to do that.
(54:30) That’s not who I’m going to model. If I if I get fouled and I’m on to the next thing, I’m not thinking about how unfair that is. I’m thinking about how I want to press forward and play, I can let go of all of those things. >> Yeah. >> Because I’m thinking about something entirely different. >> I worked with a gentleman from uh who played in the UK, played in England, and I remember having a deep rich conversation with him.
(54:51) And something else that will relate to a lot of your listeners and and people who watch is the idea of becoming visible. And visibility I think for a lot of people I think we want to be visible but it scares the out of us. And visibility for me is like having a foot on your accelerator and there’s one just resting on the brake.
(55:06) And I think visibility we’ll all kind of bravado and we’ll say oh yeah I want to be more visible but actually deep down we’re really scared or we want to be visible in a very controlled way. I want you to see me in a way that I portray rather than all of me. And I I’ll never forget talking to this amazing young man and we talked about hiding and where do you hide in life? And he said, “I I used to hide in the pitch.
(55:27) ” >> And I went and and I I like I’ve heard a lot of things like I’ve volunteered in maximum security prisons. I’ve consulted and and had conversations in the Pentagon. I’ve worked with some of the most successful entrepreneurs. I’ve worked with amazing athletes. And I said, “Excuse me? What do you mean you’re hiding a pitch?” >> He said, “I would thousands of people I would put my hand up to receive the ball and I would stand a yard to the left or a yard to the right.
(55:49) So make sure that I was in a position where I couldn’t receive the ball. I wanted to be seen to wanting the ball, but I didn’t want to receive it because I was afraid that I would make a mistake in front of 60,000 people in the stadium and maybe whatever x amount of millions people watching, hundreds of thousands, etc.
(56:06) that you can hide in the most public place. >> And I thought that was absolutely and utterly extraordinary that he was so scared of making a mistake that he would hide in such a profound way. Okay. So, if I were listening to this, there’s there might be someone listening and maybe this is just a story that I’m telling myself is like, how do I make sure this is the most value for the listener or whatever else of like two things come to mind.
(56:33) One would be okay, but how does this directly help me? You know, I’m a content creator. How does this directly achieve my goals? >> And then the second one would be like, if someone’s on board with us, I’m like, okay, but how do I actually do it? like how do I uncover the story and dig deeper, right? If they’re not at at a place where they’re like, “Oh, I clearly know my story gift and impact.
(56:53) ” >> Yeah. Well, I think I think there’s a very simple exercise that I do which, you know, I would encourage everybody to sit down and and write out their story. Um, with the view that it’s never going to be read by anybody else and it’s never going to be published, but just write your story.
(57:07) And your story is not, as I said, the soccer player, the highlight reel of his of his of his of his career. It is your story is about I was I was six or I was eight and I remember growing up in whatever city it was and I had two brothers and two sisters and I remember feeling like this and giving yourself permission to write your story and remember your story through the lens of your story.
(57:26) But there’s another exercise which we’ll get on to right now and this is a kind of a maybe a fasttrack way of looking at your story and one is to write down the three happiest days of your life. So the three a happiest days is an exercise I’ve done. You can expand it to about five, but the whole idea is just to kind of get it to look back over your life.
(57:50) Now this this is this this instruction is really really critical. >> Okay, >> this is not about finding days that are euphorically happy from 9:00 in the morning till 9:00 at night because you 9:00 at night because you probably won’t find those anyway. >> Number one. Number two is it’s not about feeling the societal pressure to write down the days that society tells you should have been the happiest.
(58:08) So for example, the wedding day, the birth of your child. It could be, right? >> But it shouldn’t doesn’t have to be. And in fact, I would almost encourage you not to. And write down these days. And it could have been a fleeting moment. It could have been an hour. It could have been an afternoon.
(58:22) It could have been something. And to write down three of the happiest days. >> Should I write down like not a full day? >> Yeah. Or or we could do it differently. You could you could write down your three happiest days. >> Okay. Um >> which might be a bit more fun. >> Let’s do Let me do Let’s do both. Um so let’s go. I’ll go here.
(58:39) This is like the our rules. Not a full day or it doesn’t have to be a full day. >> Yeah. It could have been a moment in that day. It could have been an hour. It doesn’t have to be a full day. >> And then you said skip the cliches. That’s how I would phrase it. >> 100%. They’re not as relevant as you might think they are in the context of understanding because what we’re looking for is life leaves clues.
(58:58) We’re looking for the clues. >> So if you’re okay with it, just what are a couple of days when you reflect over your life? Um, oh, I’d have to think about this more. Um, okay. So, I first I appreciate the Well, the first thing I would say is like if you’re writing it out when you say write your story, like it doesn’t have to be in public and all of that.
(59:18) >> And that gives a lot of freedom and then also the skip the cliches. Yeah. You know, so in this case, since we’re doing it in public, we’re very clearly skipping the cliches that we’ve already named. >> So, I don’t know if this gets at what you’re trying to get to. So, we’ll do it and then then we’ll see.
(59:34) Um, last week, uh, I was flying at sunset over the Sachi Mountains, which you got a chance to see Red Fish Lake and and all of that. >> Uh, and I just had this like, how is this my life moment where, you know, I’m flying a plane I I own with skills that I learned myself, you know, and and all of this.
(59:55) And it’s like just kind of a casual afterwork thing. Like I planned that I was going to do that like three hours earlier, you know. >> Yeah. Um, I think another one, uh, we’ve talked about this one because I made I made an Instagram reel about it, >> but I just a few months ago or a month ago delivered my keynote at Craft and Commerce and it was a culmination of things I worked on, you know, for to be able to talk about for a full year and all this and I was so proud of how it went and we the team nailed every part of it and I was proud of my delivery and
(1:00:31) and everything house and I didn’t see this in real time because of the stage lights on me and all of that but afterwards two friends Barrett and Cara texted me photos one from AC like the front of front of house shot and it was me on stage and then Oliver my 14-year-old off to the side because he was volunteering at the conference just watching me and like he’s he’s fully involved the weird like he’s not sitting in the audience he’s like standing off to the side kind of leaning against the railing And then the other photo was the same
(1:01:04) shot but from behind looking over his shoulder to me on stage. Uh and that was something where I was like, “Oh, wow.” >> It was so incredible to have him be a part of my world to not just think, “Oh, dad spends all this time sitting on a computer.” Like to see for him to be able to see what we’re building, the hundreds of people impacted by it, maybe get some ideas for what he’s doing himself.
(1:01:27) And like it was such like those are two photos that I will cherish forever. >> Beautiful. If you if I may, maybe one from >> further back. >> Further back. >> Yeah, because these are all very recent. >> How far back are we going here? >> Far back as you can. >> Um, I have a bunch of different examples of this, but um, we had a shop growing up.
(1:01:52) My dad built the house that we grew up in. I have a lot of very fond memories of building projects that are doing things with my dad and >> uh yeah so that go back to when I was >> and what were you what were you building give us an exact can you give me an example >> think about like building a deck >> and actually another example was I’ve always loved landscaping >> and so there’s an area by the house like in the corner of the house growing up of like landscaping like putting rocks and boulders in there and
(1:02:21) >> with your dad >> with my dad. Yeah. >> Yeah. And did you help out? >> Oh yeah. >> Were you in the way? >> No. It was quite useful. >> Yeah. [laughter] So she so you weren’t you weren’t necessarily a burden. >> Yeah. Exactly. >> So it’s what’s interesting is to remind ourselves that while we have evidence to prove in our in ourselves in a story to say we were a burden, we also when we look at our five happiest days or three happiest days or 10 happiest days that we also find begin to find evidence that we weren’t necessarily a burden. The
(1:02:46) idea behind the the happiest days is to remind us of the things and the next part of this is we talked about they don’t have to be full days. We talked about that we don’t they don’t have to be cliches and the next part of it is that we pick one. You know we can identify one. We don’t have to do it right now but pick one and and then pick another but do the same thing is why was it the most important day or why was it one of the happiest days like what was it? Because when you look at it say flying I was in an airplane whatever but
(1:03:10) what was it? >> Like what was it? What was the deeper emotional reason or rationale behind it that made it a day that you would write it up there? What did it represent to you? >> I mean, if running with that as an example, um, uh, it’s the culmination of so many things and coming back to my roots. So I think as an adult you don’t learn a lot of new skills very deliberately and you know like out of college you don’t take tests you don’t do these things and like getting your pilot’s license and an instrument rating and everything on from
(1:03:42) there like >> you it’s it’s a lot and it’s like concerted effort and so this idea that I can always learn new skills everything that I want is you know I can learn a skill to achieve it has been a great example of that um >> everything I want I can learn a skill to achieve it you say these sentences you just skip over them as if what ice cream did you order? Oh, well it was vanilla.
(1:04:03) Maybe it was chocolate. And you just land these truth bombs and yet they’re so extraordinary. Like that’s not everyday thinking, right? So, so the whole idea is to identify the days, pick the day, and then ask yourself why was it, what did it represent? And then the final phase is how do I create more of those days? >> Yeah.
(1:04:22) So, actually there’s two other parts of this. So, one is the skill and being really proud of that and the world that I unlocked. The second is the honestly the money of being able to afford that and getting to a point where like I can just do that and it’s a plane that I own and all of that. But the third thing is when I landed at this little grass runway uh up in the Saut Mountains, there’s someone who works there from the Idaho Transportation Department who maintains this runway.
(1:04:48) That’s his job. And they have cars that has a pilot you can just check out and take. They’re saying we’re going to Red Fish Lake. And he’s like, “Oh, have you been there before?” And I said, ‘Yeah, I think I’ve been there. And I’m like running through it in my head. I think I’ve been there 32 of the last 36 years, even in all of this like crazy world and doing all these things.
(1:05:06) It was still grounded in like my childhood, like who I am, the Idaho mountains, you know, I’ve backpacked all over those mountains. I’ve been, you know, all of those things. And and so like the culmination of all of those together is what made it really, really special. >> What a lot of people do is they get stuck in the money piece in the middle.
(1:05:24) And it’s great to be abundant. It’s great to to be a capitalist. It’s great to bring money into your life and be abundant with it and help other people and help yourself, etc. But the piece I loved is when you linked it back to childhood is that people get obsessed with making enough money so I can buy a plane.
(1:05:39) What I hear from you is, yeah, I’ve I’ve earned this. I’ve used this to to to buy a piece of equipment. I’ve learned the skill. It gives me the freedom to go to a place that means something to me. And I’m imagining when you landed there and you spent the day, the afternoon, the morning, you got back in the plane as a better human being. you got back in that plane having kind of just recommitted or reconnected with a part of yourself and I think that’s the point.
(1:06:03) So the the the exercise in itself is about reminding you of what is important, >> why was it important, and then the simple flip is how do you create more of those days? And for me, when I did this exercise years ago with my wife, >> her first one was her wedding day. >> Mh. And my first one was my stag party or my bucks party, which might sound kind of unusual, >> where I brought 25 guys to the west coast of Ireland um to where we now are stewards of this castle and we did a workshop and we did a hike and I remember looking back over the landscape on this 5,000-y old green
(1:06:40) road and I got a friend of mine come in and do like a personal growth workshop and some of these guys were walking this green road, this ancient road like 5 and a half thousand years ago. people would walk this road or or or maybe be on horses and uh they were having conversations about, you know, leaving relationships that were dysfunctional.
(1:06:58) One guy stopped smoking and one guy left his job that he hated and I remember thinking just for a fleeting moment. Wow. I helped create this container. >> Yeah. And then the next happiest day was a day I spent in the in the orphanage. And when myself and my wife came together and and and and shared our lists, hers was the second happiest day for her was the day in the orphanage.
(1:07:21) It’s like I didn’t know that that meant so much to her. She had no idea that meant so much to me. We talked about it and we set out and we created a mission that we were going to build an orphanage in a place that we love, which is the sacred valley in Peru. >> And we did. and with the help of other people and your your friend Dan Martell and myself he was down on the trip with us in that >> and this is such a simple exercise it’s all it’s so simple there will be people listening and watching this going come
(1:07:47) on guys surely can give me something more sophisticated this is a reminder like you going back to the lake of what is important to you and why it’s important to you but it also can inform who you want to be and the things you want to do in the world and for me the first time I created a body of work in Ireland was inspired by my happiest day which was my books party the 25 guys walking across this road.
(1:08:08) It brought them to the exact same road. I told them the story and I said, “You decide what your green road for your life is going to be.” So, it always leaves clues. We don’t need to get into the darkest days, but essent essentially the flip is the same thing. The way I describe this is that when I walk into my my my wife’s family home and I walk into the living room and there’s there’s photographs and there’s maybe a couple of certificates of, you know, maybe becoming an accountant.
(1:08:36) Um, and there’s photographs of all the girls that went to college on their graduation day. And that’s a big thing in their home, and it’s a big thing in many people’s homes. But how many of us have a photograph or an image of a catastrophe, of a failure, of something that went south, a broken heart, a shitty business, this business that fell apart.
(1:08:56) I’m not ask to literally go and create photographs and images for them. Well, I think we learn more as much if not more from some of the tougher times than we do from some of the happiest days. And the same principle is identify the darkest days, the most unhappiest days, whatever it is. Why were they unhappy? And how do we not create more of those days, but how do we eliminate those days for more people in the world? >> Oh, that’s quite the reframe.
(1:09:21) >> Yes. How do we >> how do we send the elevator down and help someone move through the same darkness that we had >> and or avoid it alto together >> because I was thinking about I didn’t know where you’re going with this cuz you’re like okay yeah how do we have fewer dark days and then that’s like that feels like something that you’re holding tight to and you’re like how do we make less bad thing fewer bad things happen to us >> and you’re like you can’t control that.
(1:09:50) >> Yeah. But this how do we eliminate these days for more people in the world? >> So something I don’t share very like you know lightly and I I’ve I’ve shared it rarely is I want to build a safe place for teenagers to come and to know who they are and to understand their story and to understand their gifts and to contemplate impact in the future at a stage when that’s the conversation I needed.
(1:10:13) I don’t know what school you went to, but when I walked down the school, the corridors in my school, there wasn’t a single door that had a little sign on saying, “Come in and get to know who you are.” >> There wasn’t a single door that said, “Understand the difference between your talents and your gifts.” There wasn’t a single door that said, “Come in here and just imagine what’s possible for you and for the world that you’re going to enter into.
(1:10:34) ” And I want to create a safe space that young men and women can understand who they are at an earlier stage so that I’m essentially creating the opposite of the lady pointing the finger at me going, I don’t know why you come here and you’re going to amount to nothing out there. So I would not have known that unless I got to this this this body of work here and these these questions like what are some of the most painful days that I have had in my life because they can inform who I want to become in the future.
(1:11:00) If you were to list out three or five darkest days, >> there’s some that you can really control and then others that you can’t at all. Is it Are you looking for things where you’re like, “Oh, this one I could actually control is the wrong word. You could help eliminate for other people.” >> And some you’re just like, “Oh, I I can’t like I guess I’ll show you a couple of mine because actually my friend Lars asked me a similar question as like just a couple weeks ago when we were together and I was like, so I had to think about it a bunch. But I I think
(1:11:25) about a time that I got very sick and like lost the ability to work and I so much of my sense of purpose or my essential sense of selfworth came from what I accomplish, >> right? And so that results in a whole bunch of depression. Um, another one is sometimes people joke or all of that about like the age gap between our kids.
(1:11:45) You know, we have a 14-year-old, a 12-year-old, and a six-year-old. And they’re like, “Oh, you know, a surprise baby or something like that.” And most times they’ll just laugh it off. Sometimes if you really irritate me with that then I will make you feel horrible about [laughter] like losing a child you know >> and I feel like if you know you give enough rope and I’m like oh I will >> you know so you think about like the child that we lost and then another one would be there’s some moments in the company right of people leaving and
(1:12:11) feeling like oh this is all falling apart but like losing a child >> whether through a miscarriage or later on like that’s something you can’t eliminate for other people whereas because the >> the being a 10-year-old listening to my parents fight about money and feeling like I’m entirely helpless in that is much more similar to your example.
(1:12:31) >> Yeah. >> And so, how do you filter between those? >> Yeah, it’s a brilliant question, and I’m not even sure I can answer it, but I’m going to do my best. >> For me, my deeper purpose in the world, my deeper why is to eradicate loneliness for as many people as I can before I die.
(1:12:47) And you’ll probably figure out based on this conversation so far that, you know, I’m a pretty deep thinker, a deeper human being in that in that sense that there’s a correlation between why that’s important to me and my own experience in life. Because really, if I had to sum it up, I think loneliness was the the thing that permeated most of my early early life.
(1:13:03) And I think loneliness is one of those really, really unnecessary feelings in life. And it’s also incredibly isolating. And I noticed Andy was was over here and the community was here. So isolation and isolation is not eradicated through Facebook followers or Twitter followers or even an office that’s full of people or even sleeping next to somebody at night.
(1:13:24) It is about is about something that’s much richer and much deeper. But when I think about eradicating loneliness for people, um it maybe eradicating is not even the right word. It doesn’t mean I create a dating app. So it’s not we’re not correlating like for like. It’s about creating environments where people can connect to themselves or something deeper.
(1:13:42) So it mightn’t be about the loss of a child, but it’s about the sense of of loss, the sense of of mourning, the sense of whatever. So imagining just hypothetically, you’re at your next company retreat and you decide for the first time, maybe maybe it’s the second, maybe it’s the fifth, maybe you’ve never shared this.
(1:14:00) You decide, I’m going to integrate this into my talk. I’m going to open up and I’m going to share this story at some point in the conference. >> And people say, well, what’s the purpose of that? That’s just a moment of selfishness. No, it’s not. Because where I go with that is how many people might be at a at a conference that you speak at? >> Uh, a few hundred or a thousand or something like that.
(1:14:19) >> There might be one person >> right >> in the back corner who lost a child >> and has never talked about it, has never opened up about it, is ashamed about it, is embarrassed by what, whatever the story is, I don’t know. And then the next minute they hear you share the story and they go, “Oh my god, I’m not alone.
(1:14:40) ” And then maybe as tears flow down their face, they turn to somebody in accounting next to them and they go, “What’s wrong with you?” And they she goes, “I lost a baby.” And that’s the first time they shared it because you’re not meant to share this stuff in a in a corporate setting or in a business setting or in a company setting. And that person then sees them and they see seen.
(1:14:58) They feel seen and heard and complete. When I wrote the one last talk, it wasn’t for speakers. It was for people who don’t believe they have a story. And my Andy is Peggy from Yellow Knife. I’ve never met met Peggy and I’ve never been to Yellow Knife. And don’t ask me where she came from and why Yellow Knife.
(1:15:17) The reason that that was so important to me was that I wanted Peggy to be able to watch a YouTube video or read a book and to hear a story and go, “Oh my god, that story matters. If that story matters, is there a possibility that maybe my story matters? And if my story matters, then I matter. And then I want to create an environment for Peggy to be able to share that with one other person in her life to be brave because she matters.
(1:15:45) >> That’s how you give the gift through the pain that you went through to alleviate somebody else so they can feel seen and feel heard and they can allow that to move through them to some extent. And I’m realizing that the the idea of your greatest gift lying next to your deepest wound, you can’t even explore if that’s true for you if you don’t like the the first step in exploring if it’s true for you is to dive into what >> what are these darkest days.
(1:16:13) It’s a very I mean it’s a a gentle a gentler way of asking like what are your deepest moments? >> I mean in a in a corporate setting we’ve literally brought into a company setting. I mean Robert Glazier who you and I both know brought me into his company. I basically facilitated the process, coached everybody, and we have heard situations, let’s just use use Peggy and Andy, let’s they say they work together, but they don’t like each other.
(1:16:35) Peggy’s in sales and Andy’s in accounting, and they just bounce off each other. They hear each other hear each other’s stories and Peggy goes up to Andy and go, “Andy, honestly, I’ve literally heard this, Andy, I got to be honest with you. I’ve actually always thought you were an but is there any chance you and I could go for a cup of coffee next week because I’d love to get to know you a little bit more?” And that’s the power of sharing your story.
(1:16:56) Sharing your story is not a burden. We use that as an excuse so we don’t have to share our story. The reason that we do that is because we don’t want to be seen. And yet we deep down desperately need and want to be seen and to be heard truly at a very deep level. And when you do that, people see the humanity in you. And as I said earlier on, they see their humanity in themselves.
(1:17:14) And that’s what creates connection. And I think even taking it further and and going to the the world that we’re in of, you know, working with content creators and knowing so many of them and all of that is you have the the gift of being able to do this at scale. >> Yeah. >> Where it’s not just the hundred people in the room.
(1:17:34) Like if you were to tell these stories, then maybe it gets watched by 100 people and one of them is touched by it. Or maybe it’s 10,000. Maybe it’s so many more who say, >> “Oh, I’m not alone. I act in this way.” >> And then the crazy thing is these stories spread and >> of course >> and everyone can see through the AI written content of the four ways to do X or that sort of thing.
(1:17:58) >> Someone told me once that if you want someone to really believe a lesson that you’re sharing, start with the painful time that you learned that lesson. >> Yeah. >> You know, and it makes it so much more applicable. And so, not only is it a way to have an impact in the world, but it’s a it’s a way to stand out and it’s a way to actually spread the message.
(1:18:17) So, this is amazing, Bill. [laughter] I’m so thrilled that we threw up some random pieces of paper and said, “Let’s let’s draw this out.” >> Well, thank you for for having me, but also thank you for sharing your wisdom and and allowing us to get a sense into your life. And to me, that’s that’s the most important thing here today.
(1:18:34) So, thank you for that. people want to follow any more of your stuff, what do you what do you have out there? Yeah, >> they go. >> Yeah, we do we do uh immersive retreats. We don’t do a lot of them. Um, as I said, we’re a small boutique company, but if people want to understand who they are in the world and what they’ve been put on this planet to do beyond what they can imagine for themselves, they can come to a retreat in a castle in Ireland as an example or come and adventure somewhere in the world.
(1:18:58) Um, and follow along philip mccernin.com. >> Sounds good. Amazing. Thank you so much, Philip. >> Thank you. Appreciate it. That was good. I got to give you a hug. >> If you enjoyed this episode, check out episode 115 with Justin Sua. He’s another incredible guest who’s worked with proathletes in the military, and it’s a great practical episode on what separates people who operate at the highest level.
(1:19:21) Like the video if you enjoyed it. Hit subscribe on YouTube or wherever you’re listening, [music] and I will see you next week.

[00:00:00] Doma: Thought leadership is the result, not the goal.

[00:00:01] Nathan: Over the years, DOMA has worked with the biggest thought leaders out there. This episode is a rare look into the behind the scenes of how they actually run their businesses.

[00:00:08] Doma: The number one source of growth in the creator economy and for thought leaders today is-

[00:00:15] Nathan: I love that.

[00:00:15] Nathan: He said that the connections that helped him land big clients came more as a result of personal, specific outreach.

[00:00:21] Doma: I had another successful outreach to my favorite club, Manchester United. Okay, yeah. Just emailed their sporting director, put together a document like, “This is how to transform the club,” and, like, went into all the tactics and what kind of players to buy and everything.

[00:00:35] Doma: He responded in, like, five days and said, “Yeah, let’s talk.” This

[00:00:38] Nathan: is how he landed clients like Arthur Brooks, Matthew McConaughey, Bob Waldinger, Bill Burnett, and Dave Evans.

[00:00:42] Doma: Connecting with that person and understanding their voice and understanding who they are and, and, and showing real interest in their work, that’s as important in my process of convincing them to be my clients.

[00:00:52] Nathan: I love having you on where you can talk about, like, “Here’s what actually works. Here’s the behind the scenes on all these big launches [00:01:00] and everything else.” Gomo, welcome to the show.

[00:01:03] Doma: Thank you, Nathan. Great to be here.

[00:01:05] Nathan: We actually met through working on Matthew McConaughey. So you have, uh, done a bunch of newsletters for a bunch of exciting people.

[00:01:13] Nathan: We’ve actually grabbed– We’ve got a few books here, uh, I should pull up. Just a few of your clients, uh, Matthew McConaughey, you know, no big deal. Uh, you came out to Boise when you were recording with Bill and Dave for, uh, How to Live a Meaningful Life. And then, uh, you’ve also got Arthur Brooks in the, uh, client roster.

[00:01:33] Nathan: So we’re gonna dive into behind the scenes in some of these book launches, some of these massive newsletter launches, and all of that. Um, but first, how does a random guy from Hungary end up being like Matthew McConaughey’s main guy for running a newsletter, uh, and then, you know, obviously doing it for so many other people?

[00:01:52] Doma: Yeah. Well, I, I still don’t understand quite myself, but, uh- But, um, yeah, I came to the US five years ago to do my [00:02:00] MBA at Harvard. Mm-hmm. Um, and I, I read Green Lights, uh, actually, like, just before that. I listened to it, I read it. I think I read it, like, four times by the time. Yeah. And so I was at Harvard and, um, I was, like, trying to figure out my life, which by the way I, I was using a lot of Dave and Bill’s-

[00:02:18] Doma: Designing Your Life book, um, trying to, like, do different prototypes as they call it. Um, and one of which was actually, like, making movies, which is still, like, one of my long-term goals. Um, and so I’m talking to a couple people, producers, directors, all that, and one of them was a producer distributor guy who ended up somehow knowing Matthew.

[00:02:38] Doma: And then basically I got connected and, uh, I, I did an internship for him, and then we started doing more and more w-work together. But it really came out of nothing. I mean, it definitely helped that I had a, a background in, like, kind of the service industry. I was at McKinsey before- Mm-hmm … which is, like, kind of the opposite in terms of, like, the creative work, uh, side of things.

[00:02:57] Doma: But, like, how do you work with someone so high profile? Mm-hmm. [00:03:00] Um, having worked with a lot of CEOs and all that, that helped.

[00:03:03] Nathan: Something else that you do that I think every creator, every entrepreneur can l-learn from is the level of direct outreach that you do. Like, a bunch of your clients, it’s just like, “Oh, I took a class from them, and then I stayed in touch, and then I pitched this,” or, “I just liked their book and so I reached out.”

[00:03:22] Nathan: Like, what are a few of those examples of you not being like, “Oh, I wish maybe someday I could work with these people on this level”?

[00:03:28] Doma: Yeah.

[00:03:29] Nathan: But instead saying like, “Oh, I want it to happen and so I’m going to engineer it.” Yeah.

[00:03:33] Doma: It’s funny actually, when I started my company Flowin, which is this creative agency for thought leaders I almost didn’t start because I had another successful outreach, which was to my favorite club, Manchester United.

[00:03:47] Nathan: Okay. Yeah.

[00:03:48] Doma: And I basically just emailed, uh, their sporting director telling them, because they were, like, basically buying the club, new owners were coming in, and, and I put together a document like, “This is how to [00:04:00] transform the club,” and, like, went into all the tactics and what kind of players to buy and everything, uh, without having any experience in- Right

[00:04:06] Doma: in that industry, um, other than 20 years of watching them. And so I, I put together this document and, and he responded in, like, five days and said, like, “Yeah, let’s talk,” and then, like, basically wanted to bring me on as, like, the chief whatever transformation officer.

[00:04:20] Nathan: Right.

[00:04:20] Doma: Uh, and then they g- they got a new CEO and somehow it didn’t work out, so, um, didn’t end up going that route, and I started a company instead, which is great, but, um, that was a, that was a funny story, um, about outreach.

[00:04:34] Nathan: So something that you do, and ’cause I, I’ve seen this a bunch of times, you have, bring a lot of clients to Kit. Uh, there was a few that we were talking about. It was like, “Oh, he, was he on Kit before?” And you’re like, “No, no, I brought him

[00:04:43] Doma: on.” And I’m, and I’m not being paid by Kit. Yeah,

[00:04:46] Nathan: exactly. Uh, but then the other side is we will, we’ll bring people to you as well, where here’s someone who maybe has a newsletter, um, or maybe has a big YouTube channel or, you know, a big [00:05:00] following in some way and wants to have a newsletter, but they need someone to, like, do the strategy and, and all this side of it.

[00:05:05] Nathan: But what I always see you do is put together these very thorough decks where it’s like, “Hey, here’s…” Not the perfect solution, ’cause you always say, like, “I don’t know. You know, you know your world better. Like, I’m coming in as an outsider, but here’s, with everything I know, here’s what I would do.” And you put it together into, you know, 10 to 15 slides and walk through it, and it seems super professional.

[00:05:24] Nathan: It’s like the McKinsey consultant- Yeah. … comes out. I think you said that once. You showed me your old deck and it was like, “Look, I, I’m, I’m a management consultant. I speak in slide decks.”

[00:05:33] Doma: Yeah. You can’t take the McKinsey out of the person.

[00:05:35] Nathan: Yeah. But what it does, whereas a lot of people would, would send off a casual email and be like, “Hey, man, I got some ideas about how you could run, you know, Manchester United better.

[00:05:46] Nathan: Uh, ping me if you wanna chat.” And everyone’s like, “No.” Like, delete, you know? But when you put in, when you take the ideas and flesh them out and then package them well, it gets this level of attention where someone’s like, [00:06:00] it’s like I don’t know how good these ideas are or whatever else, but someone clearly put a lot of thought and attention into it.

[00:06:06] Nathan: And if it’s good enough to get a, you know, whatever, multi-billion dollar um, football club to pay attention, it’ll probably get, you know, a Harvard professor or, you know, someone else to pay attention as well.

[00:06:19] Doma: Yeah, yeah. And I think with the, uh, this actually just came to my mind as, as you said it, but I, I think in this specific industry, the reason why it’s important is because what you’re basically doing is showing your own thought leadership-

[00:06:34] Nathan: Mm-hmm

[00:06:34] Doma: and also stories- storytelling skills. Like, that’s what it is, right? Right. Like, uh, a deck is a storytelling tool. Um, and that’s exactly what I’ll then need to do for them.

[00:06:45] Nathan: So

[00:06:46] Doma: you- By turning their thought leadership into a story- Yeah … um, towards the audience.

[00:06:49] Nathan: So while we’re talking about pitches and how to get in front of the right people, one, one thing that I’m curious about is how you use these credibility indicators or little signs that you have in order to get in the [00:07:00] room, right?

[00:07:00] Nathan: If you say McKinsey, Harvard, and then now you have names, uh, that you can share as well- Right … but you didn’t have that a few years ago. How do you use that in order to craft your pitch so that someone at least opens the deck or responds to the email- Right … and you can get past that initial filter?

[00:07:16] Doma: I mean, I think there’s, there’s definitely when, like, it’s a cold email, then, like, even, like, the subject line matters similar to, like, any, you know, kid customer’s newsletter.

[00:07:26] Doma: Right. Um, so for example, in the Manchester United story, I did have Harvard in the subject line- Right … and I think, uh, even some of my other, uh, experiences. But I also think that, um- Other than the kind of labels and the titles, um, it’s much more broader than that. Uh, it’s much more about who, who you are as a person.

[00:07:48] Doma: And that includes like, yeah, I can do the hard work, that’s why I got into Harvard and McKinsey and whatnot.

[00:07:53] Nathan: Right.

[00:07:54] Doma: Um, but connecting with that person and understanding their voice and understanding who they are and, and, and [00:08:00] showing real interest in their work, I feel like that’s as important in my process of convincing them to be my clients.

[00:08:06] Doma: And a lot of times it’s not even like, you know, thought through in advance. So like with, with Dave, for example, I went to one of his talks, Dave Evans, the, the author of De- Designing Your Life. I went to one of his talks at Harvard while I was still a student, and then he has this thing like office hours for life.

[00:08:24] Nathan: Right.

[00:08:24] Doma: And put his email on, and then I emailed him, and then we had office hours like three times the next three years. And as I was figuring out what to do and starting this agency, then I’m like, “Well, actually…” So he was telling me like, “Oh, we’re launching a new book,” and I’m like, “Hey, you know, that’s what I’m doing now.”

[00:08:41] Nathan: Like actually showing up and having those conversations.

[00:08:43] Doma: Exactly. And so he knew that I’m interested in the content because I was at the talk and I was talking to him for years. Same with Arthur. I mean, Arthur was my, uh, leadership and happiness professor at Harvard. At Harvard. Uh, and I was the one who was always there after for the 20-minute break asking follow-up questions about-

[00:08:59] Nathan: Great

[00:08:59] Nathan: the talk. ‘Cause they say [00:09:00] like, you know, every professor has office hours.

[00:09:03] Doma: Yeah.

[00:09:03] Nathan: Right? You know, Bill and Dave are like over the top with it, where they’re like, “If you have e-…” What do they say? “If you’ve ever attended one of our lectures anywhere”- Yes …

[00:09:11] Doma: like you’re eligible for the office hours. Exactly.

[00:09:13] Nathan: A lot of these people have ways that you can get access to them, and just taking advantage of that, especially when you’re talking about thought leaders more than like influencers.

[00:09:23] Nathan: Yeah. Right? ‘Cause they’re here to educate and teach. But even doing something like going to a talk that someone does, and then waiting in line or like talking to them afterwards, and even if it’s for two minutes, and I always try to be the one to end the conversation so that I’m not the like… I, I, I call it, um, leaving energy- Right.

[00:09:43] Nathan: versus lingering energy, right? And so you don’t wanna be the one hanging on, taking too much of their time. But then you just follow up afterwards, and you send that email and you say, “Hey, loved your event last night,” or, “Loved the, the class you taught,” whatever it is. “I learned so much from it. I was the one who [00:10:00] asked you the question about this.”

[00:10:01] Nathan: And you can continue the relationship. Anything else that you would add for like turning these Big important, uh, relationships, like tiny interactions into, you know, an opportunity to work together or a friendship.

[00:10:13] Doma: I mean, I would say like general curiosity is, is really important. Yeah. Like, oh, the reason why I wanted to work with these people, even just get close to them, I ne- sometimes I didn’t even have the idea that I’m gonna work with them-

[00:10:24] Nathan: Mm-hmm

[00:10:25] Doma: was curiosity in their work. Um, you know, Bob Waldinger is another example. He was the last director of the Harvard Study of Adult Development, and he’s a Zen priest and a therapist, and we got connected ’cause I was considering doing a PhD in mindfulness- Right … um, and, and happiness and, and he was advising me on that.

[00:10:44] Doma: And then we were talking about life for, for an hour and how to, you know, introduce Zen into your life. So had no idea that he’s gonna need the help. And then he told me once that, “You know, I have these questions about launching this online course. Like, can you help?” And, and we [00:11:00] started talking and- And you’re

[00:11:00] Nathan: like, “I actually know a lot about that

[00:11:02] Doma: world.”

[00:11:02] Doma: Exactly. So it’s kind of like, um, you know, there are things in life where, like, if you want them and you wanna figure them out too much, like you’re not actually getting them, and then, like, when you don’t want them, you’re getting them. Mm-hmm. And I think that’s where, like, curiosity is. It’s kind of like a- Right

[00:11:15] Doma: bottom-up approach, not a top-down.

[00:11:17] Nathan: The example of that would be if you had made a spreadsheet of saying, “These are the top 50 thought leaders that I would love to work with in my life.” Yeah. And

[00:11:24] Doma: I have that spreadsheet. Spreadsheets. But

[00:11:26] Nathan: if, if you started from only that place, then it would be formulaic and all that.

[00:11:34] Nathan: But instead, you’re saying, “These are the people who I love their work. I’ve read and listened to Greenlights many times. You know, I’m immersed in this world. I’m trying to learn from Bob. I’m trying to,” you know.

[00:11:45] Doma: Yeah.

[00:11:45] Nathan: Um, all of that, and then- There’s much more natural opportunities- Yeah … of like, you’re like, you know, “Hey, if you ever need help with these things, I can always do that.”

[00:11:53] Nathan: And they’re like, “Actually, in fact, I do need help with that because I’m a Stanford professor, not a professional marketer.”

[00:11:59] Doma: [00:12:00] Exactly. And then, and then the other thing, and this of course becomes more relevant, um, to the topic at hand, which is the creator economy, is that- Mm-hmm … as you also know, like it’s so connected and everybody’s- Right

[00:12:11] Doma: you know, working with everybody that like once you’re in it, then it’s much easier to get to, um, people. And like, I don’t know, when we’re on a book tour and taking people, um, to different podcasts- Mm-hmm … then of course I meet those podcasters, and if there’s one that I particularly like, I’m gonna talk to them and maybe there’s something coming out of that as well, so.

[00:12:28] Nathan: Yeah, I think I’ve, I’ve seen a photo of you and Mel Robbins together as you’ve been taking a client on, on, uh, one of those podcasts. Yeah. Well, she,

[00:12:36] Doma: she has a team of like 50 doing everything with like so much science and everything. I don’t know if I can help there, but, um, maybe, um, maybe someone else, so.

[00:12:44] Nathan: Yeah, exactly. But, but just like that’s an example of how the network, like your network spreads as you’re helping one thought leader, then you’re going to end up- Exactly …

[00:12:53] Doma: helping others. It’s like classic network effects.

[00:12:54] Nathan: Right. Okay, so you have this idea that you really take clients through and you really think about of, [00:13:00] is it seven levels of or seven key elements of thought leadership?

[00:13:03] Doma: Exactly, yeah. So it’s like basically the, the seven strategic steps to succeed- Mm-hmm … as a thought leader, and we can go through each if that’s

[00:13:11] Nathan: helpful. Yeah, let’s, let’s dive in. So the first ones start, they’re more on the art side of things, then they get more into the science side as you go along. Is that right?

[00:13:18] Doma: Exactly. Exactly. Well, I think the… So the first one, which is the most important I think, is, um- To develop exceptional knowledge or wisdom or life experience first, and going back to this thought leadership is the result, not the goal idea. Um, so you know, a lot of these thought leaders, they have like 30 years of experience as academics or writers or actors, and then they become thought leaders.

[00:13:43] Doma: Because fundamentally, what a thought leader is again, is a teacher, and like in order to teach something you have to know that thing. Right. Um, and, and, and that, that, that doesn’t mean that someone cannot be a thought leader when they’re young, because a lot of young people had amazing successes or life stories, [00:14:00] experiences, but it’s really important that you start your thought leadership in that specific field.

[00:14:05] Doma: Um, and not just like, “Okay, I’m gonna be a thought leader in-” Right … you know, football strategy. Like, like I tried to be. Um- It almost worked.

[00:14:14] Nathan: It almost worked, yeah, yeah. Then they figured it out.

[00:14:17] Doma: Then kind of the second one is getting a bit more specific, um, about the why. Like why do you even do this? What’s your mission?

[00:14:25] Doma: Like for example, Arthur Brooks’ mission is to build a happier world, and not just, um, the why, but also the how of that. So kind of like developing the theory of change, uh, the mission and the theory of change, um, which is in his case, like he wants to create a happiness movement, so he wants others to teach his material, which is like a very different approach to then like I’m just doing it alone, right?

[00:14:50] Doma: Like in terms of the, the strategic choices that you later make of bringing in other people into all this work, and teaching at Harvard, for example, and [00:15:00] hoping, uh, and actively shaping people like me, for example, who are really interested in happiness. And now I’m gonna talk about his stuff to everybody that I meet.

[00:15:08] Doma: Mm. Right? And, and that’s what I actually did, and I, you know, I, I, I was looking at his, uh, you know, Instagram the other day. I have like more than 100 friends following him. So- Oh,

[00:15:17] Nathan: wow. Yeah …

[00:15:18] Doma: so like that’s for example, an example of like having another, building a happiness teacher. Um, and he could take another, another way.

[00:15:26] Doma: Like he could just do research, right? And then maybe write one book and, and that’s it. So that’s why it’s important, like what’s the, what’s the why and the how.

[00:15:35] Nathan: Yeah. Diving into that, it’s interesting how much, like having that, that deeper why you’re doing something matters, but then also choosing how you’re going to do it, right?

[00:15:45] Nathan: And so in Arthur’s case, he’s really going to rely on other people You know, he’s saying like, “I need– This is not just me in the exclusive keynote that’s at the highest price possible, so I can only teach as few of them a year.” He’s like, “No, I have to clone these [00:16:00] ideas into other people’s and have them spread and share it.”

[00:16:03] Nathan: So, you know, as you move through, you know, each of these steps, like they’re very much in sequence because the, the downstream strategy is gonna change dramatically.

[00:16:12] Doma: Exactly. Depending- I mean, that’s what really strategy is, right? Yeah. Like you, you kind of start top down and then everything’s gonna be influenced by those-

[00:16:19] Nathan: Mm-hmm

[00:16:19] Doma: first strategy choices. And, and the third one is, um, you know, the first that’s maybe, um, a little bit more concrete, which is developing an ecosystem strategy- Mm-hmm … in this thought leadership space. There’s a transtheoretical model of behavior change that I like to use, which it sounds complicated, but it really is just like the six steps of behavior change.

[00:16:41] Doma: Okay. My friend James Clear surely talks about this a lot, um, which basically starts with the, the contemplation to change, and then it ends in like the, the transformation and the maintenance of change when you are already a changed person. And so that’s, that, those are six steps that every human goes through to [00:17:00] change.

[00:17:00] Doma: And what I’ve done is I was think– I, I started thinking about this, okay, what does this mean for a thought leader? Like, you can basically impact a human change through all those six steps, and you’re gonna do differently in each step. So if you just wanna inspire someone to start changing, then like going on a TV show and talking about something cool for twenty minutes, that’s great.

[00:17:22] Doma: But if you actually want them to, for example, start creating a habit out of it, which is a later step, then like starting a newsletter on Kit- Right … is, is a great idea ’cause it’s a weekly newsletter, right? So you can weekly, um, influence the habits of people, um, as opposed to just inspiring them once. And then if you’re like, “I just wanna like really work on transformation,” then for example, like coaching someone one-on-one is, is better.

[00:17:48] Doma: And I think there’s different people with different skill sets as thought leaders who can influence those steps differently. And for example, Artur is a good example of, uh, someone who’s, like, such a great [00:18:00] speaker that’s going on, like, doing keynotes and going to TV and all that. Like, he’s very strong in, like, the inspiration- Right

[00:18:07] Doma: side of things. But then, like, for example, Bob, who’s also a good speaker, but he actually, like, holds, like, Dharma talks and is a therapist, so he’s gonna do a lot of one-on-one work- Mm-hmm … um, which may not be as big in scale, but is probably deeper in impact.

[00:18:21] Nathan: When you think about that ecosystem, are, are there other decisions that you’ve seen people make that push them one way or another?

[00:18:28] Nathan: Or, or like, a how you match the ecosystem to the type of thought leader?

[00:18:33] Doma: Yeah. So there’s, um, there’s like a set of questions that we go through always, and, and what I talked about first was basically just about impact. Mm-hmm. But, uh, there’s of course a clear question around monetization, ’cause each of those different channels and products across these six steps have different economics.

[00:18:51] Doma: Um, so of course, like, if someone is a speaker like Artur, like, clearly, like, his speaking fee is, is very high. So like, you know- [00:19:00] speeches for him make sense. Um, whereas like someone who, you know, may, may not be as good of a speaker but has a really good network of people in like the coach community, like a coaching certification is great.

[00:19:14] Doma: And, and like Bill and Dave, I mean, they’re great speakers too, but their, their Designing Your Life book was so popular among coaches that it started a movement in itself. Like they didn’t even wanna start it. They were like- Correct … coaches coming to them like, “Hey, let’s create a coaching certification out of this.”

[00:19:29] Doma: And they’re like, “You don’t need it. Just read the book.”

[00:19:31] Nathan: Yeah.

[00:19:31] Doma: But they’re like, “No, we need it.” So like they have like a Facebook Live.

[00:19:34] Nathan: Right.

[00:19:35] Doma: And there were like hundreds of people joining in and, and now they have like these set of certifications. Um, and then, you know, a third point in that is like alignment to content, so how good of a fit your thought leadership is to the different channels, to the different products.

[00:19:51] Doma: And, and that’s actually my fourth point in, in the list, which is turning your thought leadership into specific content forms, which you can then use across [00:20:00] all these different channels across the, the six steps. But there’s, um… Because for, like you take like Bob Waldinger for example, like, I mean, because he’s a Zen priest, like w- the newsletter we launched for him on Kit, it has, um, a meditation included.

[00:20:16] Nathan: Mm.

[00:20:16] Doma: Um, so every newsletter has a m- a, a recorded video meditation, which is like really important that we actually record it on video as well ’cause he has a calming voice and presence and all this. So like having that presence is, is very important. So for him, that works really well. I have, uh, another client, Reza Sachu, who’s a m- five-time founder, billionaire entrepreneur, and like his, he’s so intense, he’s so, um…

[00:20:41] Doma: He’s creating this tension even in, in the classroom that, uh, for him, for example, like really high intensity reels really work well. So we started developing those on, on Instagram. So there, there are these different like content choices- Yeah … that you can make. Um, and especially like with writers, thought leaders, like, um, [00:21:00] written content is really important.

[00:21:01] Doma: So like that’s why starting a newsletter, for example, uh, is a clear… You can think of all, all sorts of different ways to turn the thought leadership into some content that then reaches an audience and Has an impact on them.

[00:21:12] Nathan: Yeah, that makes sense. And finding that right fit for each person makes

[00:21:17] Doma: a big difference.

[00:21:18] Nathan: Is there anything that was pitched or you’re a-about to pitch something and you’re like, “Oh, I think this w- actually no, that would not be the right, you know, content,” uh, thought leader matchup either for their, their type of, uh … like, for their topic or, you know, their style and energy as a individual?

[00:21:34] Doma: Yeah, yeah.

[00:21:35] Doma: I mean, uh, what basically happens always is that, like, you know, once someone becomes a s-successful thought leader, then all of a sudden, like, everybody’s starting to, like, approach them and like, “Let’s do this online course,” and, um, whatever, “Let’s, let’s do all these speeches.” And so there’s a lot of inbound and even, you know, it’s interesting, like, with my work and, and our work with, with Flowin, like, I’m of course in some way, like, [00:22:00] incentivized to do more and more ’cause like- Right

[00:22:02] Doma: it’s just a business model. But I need to kind of catch myself like, “Okay, let’s protect the thought leader and, and only give media projects to the client or only start media projects with the client that actually makes sense for them,” because they may not want to run around. Like Dave and Bill, for example, they’re

[00:22:22] Doma: They enjoy their life now. Like, they don’t wanna, like, run around the country giving speeches all the time and, like, of course they have a speaking a-agent, but, like, it’s not something that’s a good fit. So yeah, there’s, there’s always … Like, almost everybody gets requests all the time for different projects that just, like, doesn’t make sense for them.

[00:22:38] Nathan: Okay, what’s the next pillar?

[00:22:39] Doma: The next one is, is building the right team and that’s, um, of course a, a tricky one ’cause, like, when you-when someone’s a thought leader I mean, they might come again, like they might be a professor, and so, like even like thinking of like, “Oh, I need to hire a team now to do something, um, completely different than- Right

[00:22:59] Doma: what I’ve [00:23:00] done,” is like a big leap of faith. And I’ve seen teams ranging from like there’s just like one assistant, and then that’s it, to like a team of like 15. Like Arthur, for example, has a huge team.

[00:23:12] Nathan: Yeah, so I see this as well, where if you thought about like, uh, size of influence and team, they’re often not that correlated.

[00:23:21] Doma: Yeah.

[00:23:22] Nathan: So James Clear and Tim Ferriss both have one-ish person teams. I think Tim has, so Christa, who runs everything behind the scenes. Um, and then Tim also has an assistant, whereas James just has his assistant. You know, and so you get these like multi-million subscriber email lists, like influence and reach far beyond like the biggest magazines that have editorial, you know, like all of this stuff, and they’re like, you know, where you could reasonably have 25 to 40 people probably, and they’re like, “Nope, just, just the one or two.”

[00:23:57] Nathan: Yeah. And then, you know, on the other side, [00:24:00] like let’s, let’s break down Arthur’s team a little bit because I think that’s really interesting of the scale of, of team that he has. But I think it makes sense when you get into all the opportunities that he’s working through.

[00:24:09] Doma: Yeah, because and, you know, like audience size or influence, however you define it, I mean, Arthur’s now is like huge, um, he has like a million Instagram followers and, um, a growing newsletter and all that, but definitely James Clear’s newsletter is much bigger.

[00:24:26] Doma: So you could say like why does Arthur need 15 people and James has one? And I think that has to do with kind of going back to that number three ecosystem strategy. Like how many things are you tapping into from different- Right … channels and, and products available in the creator economy, and James is primarily focused on his newsletter, right?

[00:24:43] Nathan: It’s just

[00:24:44] Doma: the book- That’s still what- Like the book and the newsletter … and then the book, of course. Yeah. Like that’s

[00:24:46] Nathan: pretty much all. And-

[00:24:47] Doma: And he– And it’s a simple newsletter, like he can easily write it every week himself. Mm-hmm. Um, and then when he writes a book, I guess he spends a lot of time on that.

[00:24:55] Nathan: The way that he described it on actually an episode that w- we just released [00:25:00] is most people ask the question, what is the single most effective w- like tactic, strategy that I could maximize towards this goal? And so they end up doing, you know, something over here on Instagram and then over here, like they’re just spread all over the place.

[00:25:15] Nathan: And what he does instead is he desi– he draws a box around his ideal day and his ideal life, and then he says, “For a goal that I want to achieve, what is the single most effective strategy that I could do that fits within this predefined box?”

[00:25:29] Doma: Mm-hmm.

[00:25:29] Nathan: And so that’s why you don’t see him You know, doing face-to-camera reels on Instagram or growing a YouTube channel- Yeah

[00:25:37] Nathan: or, um, starting these other companies or doing all these things, ’cause he’s like, “Look, I have a very tightly drawn box and that’s, like, that’s what I’m gonna do.” Yeah. And so within that-

[00:25:49] Doma: That’s life design

[00:25:49] Nathan: in action. That’s life design, yeah, exactly. So within that, he’s like, “Okay, what can I do to maximize reach and impact and revenue?”

[00:25:56] Nathan: But he has the, you know, the order flipped. Whereas, like, quite [00:26:00] candidly, I’m in the other place where I… You know, it’s interesting hanging out with James because we’re so different. Like, I’m trying to maximize all these things. I’m in New York for the third time in six weeks. Right. I

[00:26:11] Doma: don’t

[00:26:11] Nathan: live in the city you know, despite, like you and I

[00:26:16] Doma: have hung out quite- I’ve seen you more here than in Singapore

[00:26:18] Nathan: too.

[00:26:18] Nathan: Yeah, exactly. But it’s because, like, this is what I’m optimizing for is the- Right … the joy of creation and doing it at scale and all of this. Like, I have drawn a very different box than- Right … than James has. Yeah. Yeah. And so seeing what the different thought leaders have done is interesting.

[00:26:32] Doma: Exactly, yeah.

[00:26:33] Doma: And so with a bit Archer, like you, you see him, of course, giving a lot of speeches. So like, you know, having someone who manage that is important. Mm-hmm. He goes to all sorts of universities. I mean, he’s teaching himself. He writes a lot. So like someone who’s managing university partnerships or is helping with research is, is important- Mm-hmm

[00:26:51] Doma: uh, as well. Um, so yeah, it’s just like a strategic choice and, and of course the economics have to reflect that. So like you [00:27:00] need to figure out a way to like, okay, how do we pay for this- So then you gotta, you

[00:27:02] Nathan: gotta pay those salaries …

[00:27:03] Doma: machine. Yeah. Exactly. And, um, without going into numbers with a- with any of them, like specific ones, that’s where, like, it’s so important to define what your goal is.

[00:27:13] Doma: Because again, with him, it is really to have the most amount of impact and get these ideas to– out to as many people as possible. So, you know, he’s not gonna, like… Of course, like, he could turn all of his IP now into, like, probably tens of millions of dollars, like, easily with different projects if he- if that was his number one goal.

[00:27:34] Doma: And, but his number one goal is to get the ideas out. So then, okay, I need a team to get the ideas out- Mm-hmm … and I need to choose projects that are getting the ideas out. So those are the most important things. Like giving a lot of speeches, very important, because all the people in the audience are gonna then talk about it to someone else.

[00:27:51] Doma: And like, okay, my social media team is really important because that’s-

[00:27:55] Nathan: Mm-hmm …

[00:27:55] Doma: clearly like the biggest audience. But then, you know, newsletter is, uh, important [00:28:00] because I can create word of mouth through that.

[00:28:02] Nathan: Mm-hmm.

[00:28:02] Doma: Um, so that’s why it’s, it’s like, it’s just interesting that, um, in America which is like the center of capitalism, you have an industry now where- I kind of like this.

[00:28:13] Doma: Like, it’s not all about scale and growth and like- Right … maximizing revenue, but having some sort of social impact that of course we wanna make profitable and all that. Mm-hmm. But it’s not the, the only goal.

[00:28:26] Nathan: Is there anyone that you have started to work with and then you’ve been really surprised about either the size of their team, like it being much bigger or smaller than you expected, or like a particular role where you’re like, “Ooh, that, that was super clever for you to hire that or to have someone in charge of creating that outcome”?

[00:28:42] Doma: Yeah. Um, well, I think with, uh, Artur, for example, um, he has someone who has man- just manages inbound requests for speeches.

[00:28:51] Nathan: Mm.

[00:28:52] Doma: Which just shows, like, how popular of a speaker he is. That he he doesn’t even need, like, speaking agents or bureaus or all [00:29:00] that. Like, it’s just literally someone picking up the phone.

[00:29:02] Doma: No outbound. Mm. And he does like three speeches a week or something, so. Wow. So that’s, that’s an interesting role that I, I’ve never seen, um, anywhere else. Mm. And then, you know, I’ve, I’ve seen, uh, people with, like, millions of followers have, like, no team at all. Mm. And that’s also surprising. Like, how do you even do all this?

[00:29:24] Nathan: Jefferson Fisher is someone who It surprised me how long he ran and grew his social account with no team to help him on social.

[00:29:33] Doma: Right.

[00:29:33] Nathan: Now he’s very much, like, as you think– like, as he’s redrawn the box for his life, he very specifically has- Your

[00:29:41] Doma: coaching him on the podcast.

[00:29:43] Nathan: Yeah. He’s, he’s got someone helping him on social where he can create a little bit of distance, not from, like, the connection to the audience, but for his own time.

[00:29:54] Nathan: Yeah. Where he, he is split– Like, he has someone else posting those reels for him [00:30:00] so that he’s not sucked into- Yeah, yeah … the Instagram comments and everything else, right? He’s like, “Okay, I made content, and now I can spend time with my family,” or, you know, whatever else, instead of like, “Oh, I have millions of followers, so I have to be on my phone all the time.”

[00:30:13] Nathan: Yeah,

[00:30:13] Doma: yeah. And, and I think that’s also an interesting question here, especially, like, as a service provider in the field where, like, for someone like James, for example, and I had similar examples when someone came to me and asked for help, um, and I was like, “You don’t need help.” Like, like, “I, I, I would love to make money off of this, but-” Yeah

[00:30:32] Doma: I don’t think you need the help.” And, you know, like, we– James could hire five people to- Mm-hmm … run socials and all that, but, like, if what he’s doing is working perfectly already, um, why do all the trouble? And, like, of course, people would be incentivized to, to work with him and make money off of him, but it’s not what he needs, so.

[00:30:53] Nathan: Right. Yeah. That’s, that’s interesting of, like, I guess all of these people have to get [00:31:00] really good at saying no. Is there anything that you’ve learned from these thought leaders in how they say no and the filters that they use to evaluate opportunities?

[00:31:08] Doma: I feel like maybe it’s just because I’m like, I’m like that.

[00:31:11] Doma: I mean, I, it, it’s really hard for me to- Mm-hmm … to say no, uh, in general. And, uh and, and it’s- I think the mindset is always like there’s, there’s an opportunity that can come by saying yes, even if it’s not the yes- Right … I’m saying now, but like what it can lead to. And that is, I think, true partly, uh, because that’s how, like, a lot of these things that I’m doing right now came to life.

[00:31:36] Doma: So like I don’t think you need to like turn it down fully, but what I learned from these people is just maybe it’s authenticity, maybe it’s honesty. It’s some sort of like internal like strength to say no. Like it’s, it’s just the, the skill, and I think you like really need to be like sure of yourself and like have- Mm-hmm

[00:31:52] Doma: the, the kind of self-worth that these guys have to say no, and know what is in your lane right now. Like who are you [00:32:00] really? Uh, and then it gets pretty deep quickly, but um, I mean that’s, that’s why they’re thought leaders.

[00:32:06] Nathan: Right. Yeah, that makes sense. Um, anything else on team that you’ve seen people do particularly well or that like that other creators- Hire

[00:32:14] Doma: us.

[00:32:14] Nathan: Hire, yep,

[00:32:15] Doma: exactly.

[00:32:15] Nathan: Hire the experts who

[00:32:16] Doma: have done it

[00:32:16] Nathan: before.

[00:32:17] Doma: Exactly. Um, I think for a thought leader, this is even more important than for a general creator because again, they have something that they really enjoy doing, like Arthur loves to write about happiness, uh, Matthew loves to act, uh, uh, Bill and Dave, um, loves to have office hours.

[00:32:36] Doma: Mm. So you have all these people enjoying something that- Is their number one expertise and where their wisdom and knowledge is coming from. All of a sudden, like, you wanna make them into creators and like, you know, create social media content and write newsletter and manage the newsletter. So there’s

[00:32:53] Doma: Those are things that they will not enjoy doing. So knowing what you enjoy doing as a thought leader [00:33:00] and then outsourcing everything else, I actually think that’s a very smart strategy. And like, in terms of what we are trying to do is really to make their life the easiest this way. Like take on everything that they-

[00:33:10] Nathan: Right

[00:33:10] Doma: don’t wanna do and let them focus on their craft.

[00:33:13] Nathan: Yeah, that makes sense. Yeah, I mean g- hiring the right team has made all the difference for me, so it’s … Highly recommend

[00:33:19] Doma: it. Well, you have a great team.

[00:33:20] Nathan: Um, all right, what’s the next one?

[00:33:22] Doma: Next one is, uh, building creator partnerships or thought leadership partnerships, um, but I think it’s broader than that.

[00:33:29] Nathan: Yeah.

[00:33:29] Doma: Um, what I’ve seen, and, and I measure this, um, the number one source of growth in the creator economy and for thought leaders today is creator partnerships.

[00:33:41] Nathan: Mm.

[00:33:42] Doma: Um, so people talk about like, you know, audience swapping and all these like- Yeah … complicated terms, but like it’s really just bringing my audience to your audience the o- and the other way around.

[00:33:52] Doma: Um, you have James has 3 million newsletter subscribers and, um, more and more coming in, and then Kit has [00:34:00] this great function called the Creator Network, where if I sign up to James’ newsletter, I get five other recommendations.

[00:34:07] Nathan: Mm-hmm.

[00:34:08] Doma: Um, and just because of the, the growth of, of his newsletter, uh, it’s really easy to tap into that.

[00:34:14] Doma: And then of course you, you guys have a lot of your authors in the Creator Network. So that’s just one example. And then like other examples are going on podcasts and tapping into the existing podcast audience, doing collaboration posts on Instagram. So there’s, there’s a bunch of ways to do this, and I think what is important for a thought leader specifically is to be strategic and think ahead about this, uh, in advance.

[00:34:38] Doma: ‘Cause like even if you take these, your top authors like Tim Ferriss, James Clear, like everybody wants to partner with them. Right. Right? And so now like their list is full, so unless you’re friends you’re not gonna get in there. So how do you become friends? Like you, you actually need to collaborate somehow- Mm

[00:34:54] Doma: in advance of the marketing technique of doing this audience swapping. And [00:35:00] there’s different ways to do that. Um, but just like being active in the creator economy is as important go to like craft and commerce or –

[00:35:08] Nathan: Yeah. Yeah. I mean that makes a huge difference to go to these events, uh, you know, and everything from there.

[00:35:14] Nathan: I guess talking specifically about Creator Network, right? ‘Cause so many people who are listening are going to be Have newsletters and all that. You and I spend a lot of time behind the scenes helping these creators form partnerships and, and, uh, match it up in Creator Network. ‘Cause really once you make a Creator Network connection, it’s in place for a long time, so it’s really worth it- Yeah

[00:35:36] Nathan: to get the right people. It’s not like, okay, we do a list swap thing that happens once. Like, no, no, no. If you and I recommend each other’s newsletters, like-

[00:35:42] Doma: In fact, it works much better than list swaps.

[00:35:45] Nathan: Yeah. Talk, talk about that. Why, why is that?

[00:35:47] Doma: Well, be- because I mean, just the, the, the timing of it. Like, you start today and then, like, the, unless you really mess up something, like people will keep recommending you, so you can do this- Right

[00:35:59] Doma: for like [00:36:00] five years. Um, whereas like a list swap is like a once-

[00:36:03] Nathan: Mm-hmm …

[00:36:04] Doma: thing and then, like, you, you may or may not get good conversion through whatever you’re doing as a, as a list swap. So yeah, I’ve, I’ve seen it work well. I… And I think a precondition of that is to have the relationships. So like, and, and, and there’s a lot of people in Kit, so like, it’s not like there’s five people you can be friends with and then all that.

[00:36:23] Doma: Right. But like finding the right people, um, is important, and like this is important for you guys, of course, and I, I guess the, one of the m- main business reasons why, why you’re doing it is like the more creators come into Kit, the more valuable it becomes, right? Because you can choose from all your friends.

[00:36:40] Doma: And so now when I have a new client, uh, for example, Rupi Kaur is a, is a new client that we brought through Kit as well. Mm-hmm. And, um, now, like she went on a couple podcasts before, like, I don’t know, Lewis Howes and Ryan Holiday and all that. Like, so she has those relationships, um, and so now she can, you know, ask like, [00:37:00] “Hey, can we partner in the Creator Network?”

[00:37:01] Doma: Right. So now you have Rupi, so now like, I don’t know if, uh, Rick Rubin came to Kit hopefully. Right. We gotta get Rick. We can bring him- We’ll work

[00:37:09] Nathan: on

[00:37:09] Doma: that one. Yeah. As, bring client, uh, on my list for sure. They’re connected with Rupi and-

[00:37:14] Nathan: Mm-hmm …

[00:37:15] Doma: a lot of the other Kit authors, so he would be able to get these recommendations.

[00:37:19] Nathan: There’s two sides to that. One is obviously most people listening aren’t going to have the level of network that the people that we’re talking about have. But it works at the same scale. It might not get you thousands of subscri- subscribers, it might get you hundreds, but your list might be a couple thousand, not hundreds of thousands.

[00:37:38] Nathan: And so putting in that work to partner with individuals, showing up to events, deliberately seeking out and meeting people who are in your industry but not competitive, who you could partnership, partner with and cross-recommend. Like it makes- Yeah … a huge, huge difference.

[00:37:54] Doma: Exactly. And sometimes it’s just like a simple message like I don’t have a lot of, like, my [00:38:00] own channels.

[00:38:00] Doma: Mm-hmm. Uh, it’s not my focus right now. Um, but I write on LinkedIn, for example. So, um, like last year, I saw a post of someone that talked about thought leadership and branding and the creator economy that was like, wow, this is a cool thought. So I messaged her. I’m like, “This, this is a great carousel,” like, “Congrats.”

[00:38:22] Doma: And she was like, “Thank you. Um, I, you know, didn’t even expect this to be such a hit,” because it went viral. Um, and then we had a couple of conversations because we both believe in the same things. And then all of a sudden like, “Okay, well, let’s create some mutual content around this.” And then we had like a series of posts going out, which was, you know, of course, smaller than these big guys’ scale.

[00:38:45] Doma: But it, it was just one message again that I sent and, and led to a lot of mutual opportunities, which is leading to mutual growth at our own scale.

[00:38:55] Nathan: Right. Yeah, and, and again, you know, you put it in place and it works for you forever. [00:39:00] What’s been so interesting as like a little, I guess, inside baseball thing for in Kit is just how much growth this is driving for everyone.

[00:39:09] Nathan: Mm-hmm. For most people who are active in Creator Network and like, and actually like put in the work. They didn’t just turn on the feature and say like- Yeah … “Oh, we’ll see what happens.” They like formed partnerships and, and pursued it. Yeah. It’s their single biggest growth channel, which like I know some creators who are getting more subscribers from Creator Network than all their other channels combined.

[00:39:29] Doma: Yeah.

[00:39:29] Nathan: But most of them, like Ryan Holiday, we did a case study on him, 40% of all of his growth is through Creator Network.

[00:39:35] Doma: Yeah.

[00:39:36] Nathan: And so you’re talking like they’ve added three to four hundred thousand subscribers to Daily Stoic just through Creator Network.

[00:39:43] Doma: Yeah.

[00:39:43] Nathan: And so the numbers are-

[00:39:44] Doma: And I’ve, I’ve seen that with my clients as well.

[00:39:47] Doma: Um, some even 50%, so.

[00:39:50] Nathan: You know what’s interesting is for, for both for Kit as a platform and for you as an advisor in the creator economy, like you can add, it’s [00:40:00] like a compounding amount of value because, you know, someone says, “Okay, I’d love to launch my newsletter. Who can I partner with?” You know, for us we’re like, “Well, here’s who’s already on the platform.”

[00:40:09] Nathan: For you, you’re like, “I can partner, I can try to form partnerships with anyone on Kit.” Yeah. Gotta work with the Kit team and their, you know, that creator’s team and all that to make it happen. But also like these six people are already my clients, and you’re all in- Yeah.

[00:40:22] Doma: That’s exactly what I’ve done in the last couple months.

[00:40:23] Nathan: You all want the same thing.

[00:40:25] Doma: Just connected- … the different clients.

[00:40:27] Nathan: And it’s such an interesting thing where I think people say Hey, if I’m pitching you on a partnership of some kind, you know, it’s like I’m, I’m calling in a favor, I’m asking, I feel bad about it. It’s like, well, hold on. I have a newsletter that I wanna grow.

[00:40:43] Nathan: You have a newsletter. Wait a second. We both have the thing that the other person wants. Yeah. Like, this is- No-brainer.

[00:40:49] Doma: This

[00:40:49] Nathan: is a win-win,

[00:40:50] Doma: you know? Yeah. And that’s actually, I think, one of the most beautiful things about the creator economy- Mm-hmm … is that the incentives are aligned.

[00:40:56] Nathan: Yeah.

[00:40:56] Doma: There’s basically no competition.

[00:40:58] Nathan: Right. Oh,

[00:40:59] Doma: no, I- Everybody’s incentivized [00:41:00] to support each other.

[00:41:00] Nathan: Yeah. I write a newsletter about happiness and living a more meaningful life. And so I can’t possibly refer anyone to your newsletter about happiness and living a more meaningful life because we’re very competitive. Like, that’s just

[00:41:10] Doma: ridiculous.

[00:41:11] Doma: Exactly. Exactly. Um, and you see that. Like, that’s why everybody’s, like, so- Right … supportive of each other and inviting them to their podcast and the other way, so I think that’s, that’s an amazing thing.

[00:41:22] Nathan: Another thing that I want creators to do more of, so I’m putting this out there in the universe now, is I want them to form their creator network partnerships before they air their episodes guesting on each other’s podcasts.

[00:41:36] Nathan: Because if you think about it, if someone were, were to systematize this, uh, and we’re working with, like, some podcast networks like Dear Media on things like this- Mm-hmm … ’cause they, I don’t know, they have like 80 shows. Right. And I think we’ve launched newsletters on Kit for 40 of them because they can cross-promote their podcasts, and then they all promote their newsletters, and their newsletters all cross-promote.

[00:41:54] Nathan: Right. And it’s like, um, you know, this wonderful world. But there’s a huge opportunity. You know, [00:42:00] someone will often say at the end of a podcast, like, “Hey, are there any resources that you wanna share, or where should people go?” And you say like, “Oh, well, I actually put together this whole thing on, you know, the seven ta- tactics to grow your newsletter,” or, “Here’s a, a s- series of talks that I did on living a meaningful life that you could download,” or…

[00:42:16] Nathan: And that’s all gonna have an email address behind it. But that form on the email address could then recommend, like, me as the– You know, it’s your resource, it could recommend me as the host. And so I’m more incentivized to drive traffic to, to your thing because- Right … some of it comes back.

[00:42:32] Doma: Mm, that’s

[00:42:32] Nathan: interesting.

[00:42:32] Nathan: So, like, if you were to take, um, like Andrew Huberman has so many great, you know, fitness and health influencers on his show, and he’s actually brought a lot of them over to Kit, uh, which is great. But, like, every time he has, um, uh, like Gabrielle Leon on, or, um, Dr. Andy, uh, Andy Galpin, like they’re all on Kit.

[00:42:59] Nathan: They should [00:43:00] be recommending each other so that-

[00:43:02] Doma: Right …

[00:43:03] Nathan: y- you know, so that, so it compounds in that way. And a lot of people will set this up downstream, but they really should do it before their episode drops- Mm … ’cause it just means more newsletter growth for everyone. Right.

[00:43:11] Doma: Right, right. Yeah. And you can push the podcast even to two audiences that way.

[00:43:16] Nathan: Yeah, exactly. And so it’s- That’s- … a flywheel. Anything else in the, uh, you know, the, the partnerships side of things that you’ve seen work really well?

[00:43:24] Doma: That’s more of the, the art there. It’s just like sometimes you just put people together and it’s like magic. Like- Yeah … I had like Bob and Bill and Dave, and we did like a mini podcast with them, and they just, like, enjoyed each other so much- Right

[00:43:37] Doma: that they just had a fun time. So I think that’s the other thing with these partnerships is like, yes, there’s like a business goal, a strategic goal, but sometimes it’s just like- Something that you can’t really predict in advance, but it’s just a great experience for them, so-

[00:43:50] Nathan: Well, I mean, I

[00:43:50] Doma: think- … it’s the fun part

[00:43:51] Nathan: your clients are so amazing. Like, you brought Bill and Dave out to Boise to come on my show. We had a wonderful dinner beforehand. Yeah. Uh, [00:44:00] you know, I’m a technology nerd.

[00:44:02] Doma: Yeah.

[00:44:02] Nathan: They have like- They

[00:44:03] Doma: loved you. They were like- Yeah … “This Nathan guy is something else.” They’re like, “Is he 34 already?” Yeah. And has three kids and a ghost town.

[00:44:12] Doma: Yeah. 15 in the-

[00:44:14] Nathan: But I’m like, I’m obsessed about design and user experience and Apple and, you know, and they’re like, “Oh, yeah, no, we co-founded Electronic Arts and-” “… worked on the Lisa” and when, you know, they both worked at Apple and all this stuff, and I’m like, “I’m obsessed with everything you do.”

[00:44:26] Doma: Yeah.

[00:44:27] Nathan: And so again, people think about these partnerships as, like, transactional in some way, and it’s like-

[00:44:32] Doma: Yeah

[00:44:32] Nathan: no, it’s like

[00:44:33] Doma: filled with joy. And, and it’s… Exactly. And, and that again kinda comes back to this nature of uncompetitiveness in this industry- Right … ’cause, like, if you think about it, almost in every industry, like, if it’s corporate, I mean, sorry, Mackenzie, but it’s just like- … who cares about going into these, like, industry meetings?

[00:44:49] Doma: Like- Right … it’s so boring in the, the suits and all that, and, like, even in, like, entertainment, like, a lot of people, like, they don’t really help each other, to be honest. Right. I mean, some might, and of course there’s, like, smaller groups [00:45:00] of creatives supporting each other, but, like, it’s not exactly the most friendly industry.

[00:45:04] Doma: And then, like, even science, like, it’s crazy how cutthroat that can be. Um- Yeah, you

[00:45:08] Nathan: wouldn’t expect that at all. Like, we’re all trying to just further humanity through science- Exactly … and, and no, it, like, it’s a big deal of who gets credit for what.

[00:45:16] Doma: And, and, and the difference is the incentives, right? Mm.

[00:45:18] Doma: ‘Cause the incentives are not aligned there, um, because it’s, it’s, it’s a pie with, like- Right …

[00:45:23] Nathan: expertise … there’s only so much grant money or whatever

[00:45:26] Doma: else. Exactly. And so if you get that,

[00:45:27] Nathan: it means

[00:45:27] Doma: I don’t get that. Um, like doctors too, like my dad is a doctor, and, like, the amount of attack he got throughout his career progressing as a neurosurgeon in Hungary is, like- I didn’t understand.

[00:45:38] Doma: I never understood it ’cause I never was in, in that kind of world. And here, because the incentives are aligned, everybody’s friendly and supporting each other, so that’s amazing. And I think it’s an underrated thing, ’cause like it literally like come back to wellbeing. Like it- … lowers your stress levels while you’re working.

[00:45:53] Nathan: Right.

[00:45:53] Doma: And you can also just, like, have fun.

[00:45:56] Nathan: Yeah, I mean, part of my job is to sit in a room [00:46:00] and talk to people that I really like and enjoy, you know, and you’re like-

[00:46:03] Doma: Exactly …

[00:46:03] Nathan: you know, talk about- That’s, that’s fun … how to live a meaningful life. And it’s like, well- Yeah … design it that

[00:46:08] Doma: way. That’s, that is exactly.

[00:46:10] Doma: I mean, to me and, like, personally, um, that of course is the biggest value- Mm-hmm … of all of this, to, like, learn from these people. Sometimes it gets even, like, a little bit too tricky, ’cause I’m like, “Ah, I should be following all this advice,” right? Like I should be perfectly happy and, like, have all these habits and all that, and, and I, I don’t always do it.

[00:46:29] Doma: Right. So it can get into a bit of a self-critical thing as well.

[00:46:32] Nathan: I mean, that’s just human nature. Now, as you’ve spent time around all of these people and, and all of that, is there anything that you, that you have learned or changed about, you know, like… Yeah, how, how you’ve changed as a person or something that you’ve implemented based on one of them?

[00:46:47] Doma: Yeah, I mean, I, I would hope so. Um- Almost every one of them. And you know what’s interesting is that, uh, there’s this interesting thing that happens that almost [00:47:00] every times I think I am becoming a certain person in my life or I need to make certain changes-

[00:47:06] Nathan: Okay …

[00:47:06] Doma: that’s when the, the right client comes in.

[00:47:09] Doma: So I think Matthew made me much more authentic. I mean, he’s just- Mm … the most aut- authentic- Oh my gosh, yes … person I know. Bill and Dave, I mean, first they just helped me redesign my career. Uh, but with this new book, How to Live a Meaningful Life, it’s much more focused on designing meaning moments and kind of like a mindful approach and, like, just appreciating beauty and presence in the moment.

[00:47:30] Doma: And, and that’s what I needed to, um, introduce. Um, you know, of course, with Arthur, like, uh, I was working on my happiness at the time. So, like, it’s interesting that, um, yeah, every time the new client kind of brings in exactly what I need. And I’m not saying I always perfectly- Right … implement them, but there’s always, like, some support that I think helps me become better.

[00:47:52] Nathan: Yeah. I love that. All right, what’s the next one in your list?

[00:47:57] Doma: The, the last one, which of course is, [00:48:00] you know, it’s something that then you can talk about for, for hours and you can do for years is, is, is actually to build your, um, organic channels. Mm. Um, and by organic I mostly mean like social media, newsletter.

[00:48:13] Doma: It can also be a podcast or online courses and all that. Um, and, and perfect those, not just build, but perfect those. And specifically, and this is where maybe it makes sense to talk about newsletters, um, the newsletter is the only channel that you fully own. Right. You have the email addresses as opposed to social media, which you’re kind of up to the algorithm.

[00:48:34] Doma: Um, and having those email addresses and knowing As a thought leader, I mean, one of the great things I think with these thought leader, um, newsletters, uh, which it would be actually interesting to, like, compare, like, thought leader newsletters to, like, other creator newsletters and then other random newsletters, like the open rates and the click rates.

[00:48:55] Doma: But what I’ve seen, and maybe it’s just, like, my amazing work, is that, like, we [00:49:00] cons-constantly, like, ba-basically with every client get, like, say, like, average fifty percent open rate, sometimes even much more. And what that means is that, like, basically every second audience member of yours will read whatever you have to send out that week on a weekly basis, um, right?

[00:49:19] Doma: So that is, in this fragmented attention economy, that’s, that’s very powerful. Um, ’cause, like, with, with social media, even if it gets, like, huge reach a lot of times, like the depth of that is not as much as, like, a newsletter- Right …which is kind of like a written thing. Like, you go a little bit deeper.

[00:49:35] Doma: Hopefully, people take time to, to actually read it. Um, so yeah, building those, I would say is, is number seven. And then, of course, then it gets really nuanced and like, okay, uh, what is the newsletter we’re building? What’s the purpose of it? How it’s gonna look? What’s the value, the frequency, and all those, you know, questions that we need to figure out there, and same with the other channels.

[00:49:56] Nathan: Is there a thought leader who you think does a really good job of [00:50:00] translating, like, their ideas and who they are authentically into a newsletter? ‘Cause a lot of people can do it in a pretty generic way, and then there’s a few people I think who just absolutely nail it, where you’re like, “Okay, I’m reading their voice,” or, “I feel like this is unique to them.”

[00:50:13] Doma: Yeah. From my clients, um, who I would highlight is Bob Waldinger. Mm-hmm. Uh, again, the, the last director of the Harvard Study of Adult Development. Uh, what we did with him is we basically created this concept where it’s called Hidden in Plain Sight, um, which is kinda like a zen phrase.

[00:50:30] Nathan: Yeah.

[00:50:31] Doma: And, um, we have a meditation, like a very simple meditation, nothing complex.

[00:50:37] Doma: So for even people who don’t usually meditate, it’s, it’s not even always a meditation, sometimes just like a small exercise. We record him, um, on video, um, and of course audio, and people can watch. Like, that’s the first thing they get, a, a, a video on YouTube that they can watch as part of every newsletter.

[00:50:55] Doma: It goes out Monday, 7:00 AM. It’s something you can use basically every day of the [00:51:00] week. Mm-hmm. And because he’s a Zen priest, I mean, of course it’s very natural that he would walk you through, um, a meditation. And, and of course we add like some, some stories, some Zen coins, and then bring in his, um, research as well, either from the Harvard study or other research.

[00:51:17] Doma: So it’s, it’s really combining all of his different angles of his life. So I think it’s, it’s very unique and authentic, and the feedback we’ve received so far is amazing. Uh, and, and we were just talking with some of his premium subscribers, and they were like, they, they love it. Like, it’s actually like now, like ’cause he used to have like a normal kind of just like wrote about something and then there was a premium subscription, um, which people got like some audio and Dharma talks and all that.

[00:51:45] Doma: Now we just switched to like one, and it’s like not premium. It’s all free, and they’re like, “Oh my God, this is much better than the premium was.” Mm. Um, so, so I feel like that’s, uh, that’s pretty strong, and it just has to do with like, again, what we always have to do is [00:52:00] understand the voice, understand who they are, and, and we had to create this in a way.

[00:52:04] Doma: If it was just newsletter that everybody… Like most newsletters, people just run through, uh, and it’s completely fine. I mean, it’s a, it’s a fast-paced world. But when you get a meditation to slow down- Mm … like you really need to slow down. And, and that’s the whole idea. Like, yes, we, we are creating in the online world, but with Bob, we want people to slow down, um, and take a step back.

[00:52:28] Nathan: Yeah. I like that. I think it, it being uniquely them and, uh, you know, and having it where it’s not just like, “Oh, I’m explaining a bunch of stuff,” but there’s actually a Cohen in there, and yeah, having that thought. Okay, so you’ve had a behind-the-scenes look into a bunch of these massive book launches, and you get to see, like, what works today in marketing.

[00:52:47] Nathan: Let’s say you had a friend, like just hypothetically we’ll call him Nathan. And he had a book coming out in the next six months or so. What are some of the things that you’ve seen that you’d recommend either he do or [00:53:00] anyone else launching a book where you’re like, “Hey, this is what actually works, uh, and that I would try on additional launches”?

[00:53:05] Doma: I love to think of the kind of phases of book launch in, like, three phases. So there’s the awareness phase, like you want people to know about the book. Um, there’s the sales phase, where you actually sell them the book. And then there’s the word-of-mouth phase, which is really the most important, when they start talking about the book to others as well.

[00:53:23] Nathan: Mm-hmm.

[00:53:23] Doma: Um, and I learned a lot of this, like, through the first book launch I’ve done. I… Well, there was, you know, no previous experiences with anything you do the first time. So I actually learned a lot from your podcast even. Yeah. Uh, like you had, uh, Tim Ferriss on, um- He’s a legend. He’s so good … super, super helpful, and I talked to him, uh, ’cause you connected us.

[00:53:43] Doma: And then, um, of course, you know, Tim Ferriss and James Clear and all those guys, like, they’ve done some incredible launches that I kind of then codified and, like, now I have this, like, basically big book launch Bible, uh, document and auto deck. [00:54:00] And so I think the, the awareness phase, which is interesting in the context of what we’ve been talking about with the, the organic, um, content and that you create, warming up the audience to your book launch, uh, is a really important thing that I think works well.

[00:54:15] Doma: Newsletter is especially helpful in that. And, and there’s a couple people like Ryan Holiday who do, who do this really well, where, like, they release certain excerpts- Mm … from the book, um, as part of their newsletter, and then it’s like, “Hey, do you want more? Pre-order the book.” Right? Right. Uh, so it’s a smart strategy to create some anticipation.

[00:54:34] Doma: Now, the key there, of course, is, like, not to give away too much ’cause, like, you can also give away too much, and then, like, it doesn’t… It’s not no longer as interesting. Uh, but Tim Ferriss actually said an interesting thing there was, like, you actually want people to read your book, not to buy your book.

[00:54:49] Nathan: Yeah. ‘

[00:54:50] Doma: Cause one happy reader will tell five others who will buy it. So in that sense, giving away too much may not actually be that much of a problem to your newsletter list- Right … ’cause if [00:55:00] they love these concepts and they say like, “Hey, Nathan has this amazing book coming out, buy it,” then not, maybe not an issue if they don’t buy it, right?

[00:55:08] Doma: So I would say that’s, that’s number one, kinda teasing the content. And part of that is also testing the content, right? Like what, um, you can go into like details even with like chapter titles. Like you can A/B test chapter titles in your newsletter. Um- Oh, yeah … right? Um, and, and that, that has a, a huge impact.

[00:55:26] Doma: And then the other thing with like, you know, what James Clear did, like the free chapter lead magnet. Um, so there’s, there’s a bunch of those kind of pre-warming things you can do. I also think that kind of going back to creator partnerships Setting those up in time are really important- Mm-hmm … uh, especially now, like, podcasts are booked out so far in advance that it’s really important to, like- Is that, like-

[00:55:49] Doma: nail them …

[00:55:49] Nathan: two to three months or, like, six to eight months in advance?

[00:55:52] Doma: I mean, I, I… We, we did have, for example, with Bob, we’re, like, booking Matt Robinson, like, the first date is, like, [00:56:00] October now.

[00:56:01] Nathan: Right. That

[00:56:01] Doma: they

[00:56:01] Nathan: have available. We’re recording this in mid-June.

[00:56:03] Doma: Yeah, exactly. So you’re talking four

[00:56:04] Nathan: months or more-

[00:56:05] Doma: Yeah, um-

[00:56:06] Nathan: even for the first option to be on the show.

[00:56:08] Doma: And then, you know, what James Clear talks about always is the, this concentrated strike approach where, like, you need to drop all the podcasts in a two-week window of your publication. So, like, you really need to be strategic and think ahead of, like, “Okay, how am I gonna convince every podcaster to actually drop in that window?”

[00:56:26] Doma: Like, it’s better to probably record in advance and maybe agree on a date-

[00:56:30] Nathan: Right …

[00:56:31] Doma: together. So I think that’s, uh, that’s an important one.

[00:56:34] Nathan: Is there anything for… Like, you’ve seen a bunch of these pitches that then get on the biggest shows. Yeah. If you were to take, like, a Mel Robbins or, or a, um, you know, other shows at that scale, what are the things that make the biggest difference to get on, on the show?

[00:56:50] Nathan: Is it the topic? Is it the, like, the influence and credibility of, you know, or the reach? Like, what are the things that, that matter the most in that pitch?

[00:56:58] Doma: So I think, [00:57:00] um, every podcast has their own criteria, which, um, I mean, at the end of the day, they’re very similar. I mean, like, the, the host’s interest in your content- Mm-hmm

[00:57:10] Doma: of course, very important because they wanna be excited about stuff. Relationship to you, the growth potential, like, looking at your own audience and, like, their audience, like how much they love that content. Is it a fit? Mm-hmm. Um, so there’s a few of those factors, but I would say, like, some of those are not even in your control.

[00:57:27] Doma: Right. Um, and I think the most, number one most important thing that I’ve seen, and actually the reason why sometimes I feel like me pitching is maybe m- even more effective than if the publicist doing it, is the personality in those emails, in those pitches, right? Like, and, and- It’s not a, not a generic PR copy-paste.

[00:57:46] Doma: Exactly. Like- Because, like, you can sense when, when it’s a PR… And n- n-

[00:57:46] Nathan: nothing wrong with that,

[00:57:51] Doma: and you need that for volume. But when you have, like, you, you have one podcaster, like, y- you really wanna get on, and, and, and would [00:58:00] be super hard, clearly, ’cause they’re booked out, and they have all the big names. Like, write a super personal email.

[00:58:06] Nathan: Mm-hmm.

[00:58:06] Doma: And I’ve s- I’ve seen that, like, I’ve got this feedback on my emails that, like, “This actually convinced me,” ’cause it was personal, and you connected the dots and all of that.

[00:58:15] Doma: So I would say, yeah, focus on that.

[00:58:17] Nathan: You’re putting that McKinsey level of effort into- Yeah. … into the podcast.

[00:58:20] Doma: Yeah, McKinsey, but also just, like, kind of going back to, like, the bottom-up, like curiosity- Yeah … about, like, there’s something, like, real there. There’s a, there’s a connection between the two people, and so how do you find that?

[00:58:32] Doma: And I think they do resonate to that, ’cause they’re also… I mean, I think Tim Ferriss and, and, and Rich Roll, they also talked about this, um, a couple times. Like, a lot of people are, like, tired of, like, just being the book promoters- Yeah … as podcasters. So how do you make it more personal, more engaging?

[00:58:48] Nathan: Is there a podcast that you’ve had one of your clients go on or that you’ve seen the, like, some of the behind-the-scenes numbers that had, like, a, a bigger spike in book sales or whatever [00:59:00] outcome you’re trying to create than expected?

[00:59:01] Doma: Yeah, I mean, Matt Robbins is insane. But

[00:59:03] Nathan: w- but we kind of expected that. Yeah. I mean, so it makes… It’s good to know that, like, her show delivers in, in sales.

[00:59:10] Doma: Yeah. Uh, well, another one is Hidden Brain we’ve seen-

[00:59:13] Nathan: Oh, yeah … work really well. That one, yeah.

[00:59:15] Doma: Um, yeah, I would say those, those two were, like, the, the outstanding- Yeah

[00:59:19] Doma: highlight ones. But sometimes you even, like… You, you can also think of this as, okay, there’s the concentrated strike. You wanna get the biggest names there.

[00:59:28] Nathan: Mm-hmm.

[00:59:28] Doma: But maybe is there a way that we can get noticed in advance and maybe just go on a podcast that, like, you don’t even talk about the book? But, like, they’ll see Nathan, uh, this guy who talks about some super cool topics, has an interesting life, and then their, the, the, the podcasts you wanna get on, like, their bookers will see you-

[00:59:47] Nathan: Oh,

[00:59:47] Doma: okay

[00:59:47] Doma: and invite you because you were out there talking.

[00:59:50] Nathan: Do you feel like you’re starting to get a sense in the industry of, like, okay, what, who is influenced by whom? Or, like, you’re starting to see some network effects- Yeah,

[00:59:58] Doma: exactly.

[00:59:58] Nathan: Like, for instance- … if we get on this show, [01:00:00] it may be small, but that host is really well respected, or they share a booker with this much bigger show.

[01:00:06] Doma: Exactly.

[01:00:07] Nathan: Yeah. That’s interesting. I was leaving an event in LA, I don’t know, like, three weeks ago, and we’re waiting for our Uber, and Chelsea on my team just starts talking to the person next to us who’s also waiting for an Uber. Mm-hmm. And so we meet and say hi, and it’s like, “Oh, what do you do? Everyone Kit,” and he’s like, “Oh, I, uh, run podcast booking for, like, most of the biggest shows.”

[01:00:25] Nathan: You know, and you’re like, “Okay. Well, we’re gonna get in our Ubers,” you know? Wow. And I texted him and was like, “Hey, tell me a little more about what you’re doing.” And he called me and was like, “Hey, you know, on the off chance that you’re free right now, ’cause I know you’re sitting in an Uber,” like, “I, I watched you get in an Uber.

[01:00:38] Nathan: I got in mine.” And so for the next, like, 15 minutes, we just chatted. But it made me realize how much- Like this is an actual agency that handles bookings for Emma Gried and like a bunch of big, big shows. And, you know, you start to realize like, oh, it’s not just the host that’s doing all this. Yeah. Like they have a whole system, and they say, “Hey, here’s the [01:01:00] topics and the types of things we’re interested in, and who, here’s who’s not a good fit.”

[01:01:03] Nathan: And so there is like this right-hand person behind the scenes who’s like, who’s that filter gatekeeper, and you can actually get to know who that person is.

[01:01:12] Doma: Yeah, exactly. I mean, it’s the same with like, I guess the creative economy was the same with like actors and like a lot of like, you know, sports players and, and all that.

[01:01:20] Doma: Like when you’re a kid, you think all these people are just individuals who do their job, and it turns out they have like a staff of 15 doing- Yeah … everything for them. So it’s an interesting, you know, business kind of consideration, like how do you run a thought leader, a creator, a sports player?

[01:01:36] Nathan: Yeah. Was there anything else, uh, from the book launches that stood out that you were like, “Oh, I would make sure to do this on, on a launch”?

[01:01:43] Doma: I think bonuses Um, and lead magnets, um, are important. And then one thing that, uh, we’ve seen work well, uh, with Arthur, for example, we had his, um, book launch recently, his live event-

[01:01:56] Nathan: Yeah …

[01:01:57] Doma: um, where he just brought in a lot of his [01:02:00] friends and, uh, other big creators and thought leaders. Um, and it was, it was around meaning.

[01:02:08] Doma: Um, and then of course, there was a pitch to, you know, buy the book- Mm-hmm … uh, as part of that event. So

[01:02:14] Nathan: this is like a big virtual summit or live event.

[01:02:17] Doma: Yeah.

[01:02:17] Nathan: I believe that one was at Sage Studios in South Carolina. I go to that studio every year for a mastermind, and so it’s one of those things where- Nice

[01:02:25] Doma: I

[01:02:25] Nathan: think I was talking to Arthur’s team about it and, and, uh, I was like, “Oh, I know Barry and Blu who run run that studio,” and-

[01:02:32] Doma: Exactly. Yeah. So I mean, and, and that basically like is another example of like a funnel strategy in this business, right? Like, you create something that is for a bigger audience, um, top of the funnel, and then you turn, you give them value, and then you turn some of them into, in this case, book buyers.

[01:02:50] Doma: Right. But the same can be done with just social media, same can be done with like long form YouTube content, and then like the activation is buying the book or just a [01:03:00] lead magnet for your newsletter. Um, so it seems like this funnel thing is very popular- Yeah … uh, in the creator economy.

[01:03:08] Nathan: Yeah. That makes sense.

[01:03:09] Nathan: Well, putting together a, a big live event is something that I’ve been thinking about doing for the Ladders of Wealth, and, uh, I’ve got some documents drawn up and all that, you know, and some plans there. Mainly because not only can you get a lot of friends to help promote it, right, in the partnership sense, but also it’s really good for driving paid ads too.

[01:03:27] Nathan: You know? Right. It can be this event that you can build up to, and there’s a reason to show up, and you know, it’s, it’s easier than just driving ads to a book.

[01:03:36] Doma: Yeah. That’s smart.

[01:03:37] Nathan: Okay. So we’ve talked about this a lot behind the scenes, but what are you doing with like Flowin as a business? Like how, how are you operating?

[01:03:44] Nathan: Where, where do you plan to take it?

[01:03:45] Doma: Good question. So yeah, it’s Fl- Flowin is my business, which is, um, basically a creative agency for thought leaders. Um, and what we do is, is basically content development and audience growth for [01:04:00] thought leaders. Mm-hmm. And, um, what that specifically means is we typically start with developing the strategy through these seven steps.

[01:04:08] Doma: Um, the brand is really important for thought leaders to keep the, keep that sacred, um, visually, um, and otherwise. And then we go into, okay, now we’re launching a book. So it’s a book launch or launching a newsletter maybe in support of a book launch. Um- Building a new social media presence, launching a podcast, launching an online course.

[01:04:28] Doma: So using all those channels that we, we talked about as part of the ecosystem strategy. And so we, we manage these, we create a content for the thought leader and, um, try to make sure that they really can, as I said, focus on their craft and we handle everything else. Um, so it’s kind of a one size fits all situation.

[01:04:46] Doma: Yeah. In terms of Um, you know how we, how I run it, um, I started alone and then, like, I hired my own brother and, and another guy. So, um, basically it’s the three of us, uh, full time right now. Nice. But I’ve, [01:05:00] like, twelve to fifteen contractors who help out with the different pieces of expertise. Um, I’m thinking, you know, what is the right model?

[01:05:08] Doma: Is this contractor model is, uh, the best, or do I maybe have, you know, five people full time and that’s how I run it? And in terms of scaling, I mean, that’s another, um, maybe countercultural thing that I have in my mind. I don’t wanna scale it too much- Yeah … ’cause the most beautiful thing that people probably recognize just through this conversation is that I can work with these, uh, amazing thought leaders, um, one-on-one.

[01:05:32] Doma: And if I, if I had twenty clients as opposed to five that I have right now, um, all of a sudden that becomes much more transactional. Right. Uh, and so these one-on-one interactions and even like, you know, my own creativity, like how do I come up with ideas? Like, I couldn’t do that for twenty people, right? But maybe there’s a little bit more, more scale in it, um, for sure.

[01:05:54] Doma: So I’m, I’m thinking about that. But fundamentally, like, the reason why I do it is because, one, I wanna have [01:06:00] an impact o-on people and their well-being, um, through these, uh, amazing thought leaders, and I, I wanna have fun. Yeah. It’s fun, uh, working on this content. Um, you know, as, as I said, like, I love movies. I– maybe we can create thought leader movies in the future.

[01:06:16] Doma: Um, maybe we can write our own books. Um, so I’m just… I just, I just wanna enjoy the ride. And, and of course, there’s an element of like flexibility too, which is pretty cool that, you know, I’m, I’m here recording with you in New York, uh, but next week I’m going to Hungary, do a little sailing and surfing in my home.

[01:06:33] Doma: Yeah. And like there’s– I’m not tied into one place. Um, so I would love to keep that flexibility for the future.

[01:06:40] Nathan: Yeah. I love it. Well, I feel like we often hear from the big forward-facing name, and you ask them questions about, like, what’s actually happening behind the scenes, and they’re like, “Yeah,” and they give some high-level answer ’cause they don’t actually know.

[01:06:52] Nathan: Right. And so I love having you on where we can talk about, like, here’s what actually works, here’s the behind the scenes on all these big launches and everything else. [01:07:00] So if people want to either follow your content as you’re writing on LinkedIn, um, and, and all of that, or potentially work with you, what would be the best way to reach out?

[01:07:09] Doma: Yeah. So, um, our website is flowin.consulting, um, and my, you know, people can reach out on my email as well, doma, D-O-M-A, @flowin.consulting, um, directly. And in my LinkedIn, I’m under Domonkos Eros, E-R-O-S-S. Uh, it’s a, it’s a complicated name, but- Yeah … I guess they can find it in the show notes. That’s my, that’s my LinkedIn.

[01:07:33] Doma: So yeah, just reach out there.

[01:07:35] Nathan: Sounds good. Well, it’s been a ton of fun working with you on a, a bunch of amazing newsletters over the last couple years, and, uh, thanks for coming on the show.

[01:07:42] Doma: Yeah, likewise. Thank you, Nathan.

[01:07:43] Nathan: If you enjoyed this episode, go to YouTube and search The Nathan Barry Show, then hit subscribe and make sure to like the video and drop a comment.

[01:07:52] Nathan: I’d love to hear what some of your favorite parts of the video were, and also just who else you think we should have on the show. Thank you so much for listening.

[00:00:00] Chris: Personal brand is about who you are, understanding your voice in this world, your values, and being able to communicate that. It’s devoid of you trying to make money.

[00:00:08] Nathan: Chris Do is an expert when it comes to personal brand. He’s an Emmy award-winning designer and founder of The Futur, which has grown to 2.8 million subscribers on YouTube.

[00:00:16] Chris: If you wanna develop your personal brand, you need to know what your keyword is, what you want to be associated with. So when people think of this word, they think of me. The vast majority of people who speak about personal brand, the 99.9% of them, I’d argue they’re not working on their personal brand at all.

[00:00:31] Nathan: What are they working on?

[00:00:32] Chris: They’re working on their marketing funnel, calling it a personal brand.

[00:00:35] Nathan: It actually all starts with figuring out who you are outside of what you’ve built. Do

[00:00:39] Chris: you feel like you know who you are, your identity? Um, I- Can we get real vulnerable?

[00:00:44] Nathan: Yeah,

[00:00:44] Chris: we can do that.

[00:00:45] Nathan: Partway through this episode, he actually turns the interview around and he starts coaching me.

[00:00:49] Chris: I’m asking the questions now. Yeah, you’re in charge. I want to write in your notebook. I wanna map some of this. Okay. In case something comes out.

[00:00:55] Nathan: This was one of the most special episodes I’ve ever recorded on this show, and it’s because of how Chris shows up and the things that he teaches for you to change how you show up as a creator.

[00:01:05] Chris: Have you shared this before?

[00:01:06] Nathan: Uh…

[00:01:07] Chris: Oh, my gosh. This is gonna be a juicy episode. You said we were, we’re not gonna go that deep, but we’re gonna go deep, okay?

[00:01:14] Nathan: No, actually,

[00:01:15] Chris: I see it the complete opposite. Thanks for sharing that story and for being real with me.

[00:01:18] Nathan: Thanks for drawing it out.

[00:01:19] Chris: Oh, we’re not done with the drawing yet.

[00:01:25] Nathan: Chris, welcome to the show.

[00:01:26] Chris: Thanks, Nathan.

[00:01:26] Nathan: Something that you talk a lot about is personal brand.

[00:01:28] Chris: Mm-hmm.

[00:01:29] Nathan: And I know a lot of people, and we probably both do, who put tons of effort into their personal brand and don’t feel like they’re getting attention and eyeballs on it, like, and it, and that it’s actually resonating.

[00:01:39] Chris: Mm-hmm.

[00:01:39] Nathan: You have this phrase that I’ve heard you say of un-bland yourself.

[00:01:42] Chris: Yes.

[00:01:43] Nathan: What does that mean?

[00:01:43] Chris: Okay. Well, I, I will tell you the origin of where that idea or word comes from. A, a friend of mine, he’s a luminary in the design space. His name is Brian Collins. He has an agency, agency of the year kind of stuff, and he, he has a playful way of talking about things.

[00:01:59] He’s like, “You know, it’s not called blanding, it’s branding,” and he makes fun of all these other big multi-million dollar agencies who are doing very high-end brand work, and he goes, “It’s so boring, blah, blah, blah. It’s all the same.” Right. And he wants to inject personality, humor, fun, a point of view, and so I keep thinking about that, and then hard stop, I, I look at people and how they show up online, and we’re all kind of insecure about who we are- Mm-hmm

[00:02:25] in real life, even more so online. So what we do is we follow certain templates or mandates, so, so to speak, from people who tell us this is how we’re supposed to be.

[00:02:35] Nathan: Mm-hmm.

[00:02:35] Chris: There’s a, an averageness, a sameness that we aspire towards, which is really strange to me. And so everyone is just blending in. So we need to stand out, and to, to summarize what, what branding is, it’s differentiation.

[00:02:48] How are you different than your competitors? Mm. ‘Cause that’s the only thing people remember. An undifferentiated product in the market space is called a commodity.

[00:02:56] Nathan: Right.

[00:02:57] Chris: If I can’t tell the difference between one phone to the next, I just buy purely on specs and price at that point, and you’ve lost the battle.

[00:03:04] The, the ongoing debate, not debate, but the observation is Apple has a brand. Dell doesn’t. Because, uh, for Dell, all we do is we look at the price point and the features Right There’s no feeling. We have no loyalty to them. Mm-hmm. We don’t go and extol their vir- virtues to everybody else. We don’t wear Dell T-shirts.

[00:03:22] We don’t put their stickers on our other products. We don’t brag to our friends. We don’t shun our friends who don’t use Dell products. Dell sells a machine. Right A very good machine at a great price point, and I’m appreciative of that, but they don’t really have a brand. So people who are out there trying to create content, I think they fall into Dell camp.

[00:03:39] Mm-hmm. Serviceable, highly forgettable. So what we have to do is we have to lean into what makes us different. We have to un-bland ourselves.

[00:03:47] Nathan: I saw someone … I, I saw this play out on X the other day, where someone was like, “Look, I need a new monitor. I can buy the Apple monitor for, whatever, $2,500-” Right … or something, or I can buy the Dell monitor that’s the same size, same specs,” you know, the

[00:04:02] There’s probably some differences, but to them, you know, they’re comparing specs, “Or I can buy this for, like, $700.” Yeah. “Like, which one should I buy?”

[00:04:07] Chris: Right.

[00:04:08] Nathan: And you, if you looked in the comments, probably a third of it was about specs, and a third o- like, a third or more was about, like, identity, brand, who you are.

[00:04:18] Mm-hmm. Mm-hmm Like, you know, that sort of thing. Where it was like, you know, or pe- people would say things like, “Well, you make lots of money in your business, so, like, just buy the Apple,” you know? Yeah. Like, and all of that, and you realize, like- You

[00:04:27] Chris: can afford it …

[00:04:27] Nathan: all, all Dell has going for it is specs and price.

[00:04:30] Chris: Right.

[00:04:30] Nathan: And that was the only thing.

[00:04:31] Chris: Yeah. Are you familiar with Maslow’s hierarchy of needs?

[00:04:34] Nathan: Yeah.

[00:04:35] Chris: Okay, we talk about that, and, and I think it’s withstood the test of time, that we can kind of almost say that there’s some truth to this, right? Mm-hmm. At the bottom is survival. What’s at the top of Maslow’s hierarchy of needs?

[00:04:45] Nathan: Self-actualization.

[00:04:46] Chris: Mm-hmm. What does that even mean?

[00:04:48] Nathan: I, I don’t know

[00:04:49] Chris: Right. It’s kind of a little bit strange, right? It’s vague. Yeah. And I think it’s to achieve your human potential or something like that. Mm-hmm. And it’s a very difficult concept to understand, but if I were to describe it to you differently, maybe it’ll be more memorable and we can see some truth in that.

[00:05:04] Hermosa talks about the three things that you need to sell to people; health, wealth, and relationships.

[00:05:08] Nathan: Mm-hmm.

[00:05:09] Chris: Make me stronger, faster, better, let me live longer, make my skin perfect, that would be under the health category.

[00:05:15] Nathan: Yeah.

[00:05:15] Chris: Above that is wealth. Uh, wealth is, like, generate more money, give me more freedom.

[00:05:21] And then above that is relationships, and help me to improve my relationships with my partner, with my, uh, with my spirituality or something like that. There’s something there, my community. And then he stops there. Like, no, there’s more to that. There really is, and I think he talks about it, but he didn’t build into it.

[00:05:39] So at the bottom is health, above that is wealth, above that is relationships, and then I think he’s just missing two categories. Status.

[00:05:46] Nathan: Mm-hmm.

[00:05:47] Chris: Which is I’m signaling to people all the time about who I am.

[00:05:51] Nathan: Right.

[00:05:52] Chris: And, and above that is identity. Who am I? So it maps perfectly to Maslow’s hierarchy of needs- Mm-hmm

[00:05:59] ’cause at the bottom, survival, health, and at the top, self-actualization or identity. Who am I? So I think that’s the big question of our lifetime is who am I in this lifetime? Did what I do, did it make a difference in this world? Do I matter? I think when we fast-forward to 100 years from now when you’re almost ready to die, you will ask yourself- Did I matter?

[00:06:20] Mm-hmm. And if the answer’s no, it’s kind of a sad existence. And so the thing about status and identity ties into branding. So when I buy an Apple monitor, it’s not like I need specs or I need- Right … to have a screen, it’s because, well, who am I? Am I a person of taste? Mm-hmm. Am I successful enough to afford a luxury like a monitor that’s cost three to four times as much as the other comparable monitor?

[00:06:46] I am. And I’m an aesthetic person, so I care about what things look like, not just how they function. Mm-hmm. And there’s a joy in the moments in which you unpack, open, and look at this thing every single day, that you remind yourself, “I did it.”

[00:06:59] Nathan: Right. ”

[00:06:59] Chris: And I proved the naysayers wrong, and I can have these things.”

[00:07:02] And you can take this across the spectrum from water to pizza to cars. Everything you do or buy says something about you, and this is how we’re signaling to other people our status and our identity. It’s a really important thing for us to start to understand because we’ve moved into a time in which there’s abundance, and we live longer, we have more things, and there’s less to kill us.

[00:07:23] And so we start to move towards the higher, uh, the, the top of the tier of Maslow’s hierarchy of needs.

[00:07:29] Nathan: Is there a brand that you can think of, uh, either as an individual or, you know, like a, a corporation that has made that shift from, you know, the Dell to the Apple?

[00:07:38] Chris: Target.

[00:07:38] Nathan: Okay.

[00:07:39] Chris: Target’s a great case study.

[00:07:40] Nathan: Tar-jay.

[00:07:41] Chris: Yeah, Tar-jay. Um, I remember growing up not having a lot of money.

[00:07:45] Nathan: Yep.

[00:07:46] Chris: So there are discount dis- big box stores that if you were seen in, it would signal to other people that your parents aren’t doing well. Right. Like for us it was Kmart.

[00:07:54] Nathan: Yeah.

[00:07:54] Chris: And my parents and, um, you know, I’m an immigrant. Being immigrants, we, we wanna bargain.

[00:07:59] We don’t wanna pay for a brand. It doesn’t make any sense. And it was always a running joke in junior high or elementary like, “Oh, you guys shop at Kmart.” I’m like, “God dang it, we do.” Yeah, you’re right. It’s so shameful. Yeah. The blue light special, like how do we get around this? Yeah. And you know, my mom’s sage advice was, “Why are you so afraid of being seen at Kmart?”

[00:08:16] Nathan: Mm-hmm. ”

[00:08:17] Chris: Because if they see you, you have equal ammunition.” And I’m like, “Mom, that’s just not how it works.” Oh, because- I know that’s a logical- … because her point

[00:08:22] Nathan: is

[00:08:22] Chris: like- Yeah, it’s like- … yeah,

[00:08:23] Nathan: we’re both at

[00:08:23] Chris: Kmart. We’re both at Kmart. You sign here. Right? It’s like how can you tell people, “‘Cause how did you see me?”

[00:08:27] Right. Right? But in my emotional, undeveloped brain, I’m like, “It don’t matter.” Right. “Now people are gonna know.” And Target is Kmart. With brand.

[00:08:37] Nathan: Hmm.

[00:08:38] Chris: Okay? If you look at Kmart, Kmart pushes discount, best price. The same thing with, um, what is that, uh, Walmart.

[00:08:44] Nathan: Yep.

[00:08:44] Chris: It’s always the best prices. Right. Like, the blue light special or whatever they’re promoting, the smiley face guy.

[00:08:50] Nathan: Yep.

[00:08:50] Chris: Target went a different direction. They’re saying, like, like, affordable quality or affordable luxuries. That’s what they wanna be able- Yeah … to create. So instead of just pumping out cheap OEM white label things, they partner with legitimate designers, architects- Mm-hmm … industrial designers, and people with a brand name, and then they’re able to use their distribution, their manufacturing power, their buying power to get you, it’s something that is a higher quality for a decent price.

[00:09:17] Nathan: Right.

[00:09:17] Chris: So they shift the emphasis away from it being cheap to it being good and affordable, which changes the narrative.

[00:09:23] Nathan: If you walk through… You know, I’m thinking about seeing something from, like- Mm-hmm … Chip and Joanna Gaines in the home goods section- Mm-hmm … at Target, right? And it’s well-branded, it’s well-positioned.

[00:09:31] It’s not very expensive.

[00:09:33] Chris: No.

[00:09:33] Nathan: You know? It’s probably more than the equivalent whatever item would be at Walmart or that sort of thing, but it, it has design and taste and, and all of that too, and it’s partnered with someone who has brand.

[00:09:43] Chris: And they’ve done this for decades.

[00:09:44] Nathan: Mm-hmm.

[00:09:44] Chris: We’re aware of it now, but when I was in school, go to Target, they had ar- famous architect Michael Graves design a set of home goods.

[00:09:52] Nathan: Mm-hmm.

[00:09:53] Chris: So Michael Graves doesn’t do this, I mean, he’s an architect, but they got his perspective. And I think they’ve been doing this for a really long time, and you can see this. And then they did the thing with, I think, Martha Stewart or-

[00:10:04] Nathan: Right …

[00:10:04] Chris: you know, they, they bring in big name brand people who have a sense for design.

[00:10:08] Hopefully it’s not just them signing off on things they have no involvement in, we hope.

[00:10:13] Nathan: Right.

[00:10:14] Chris: But in theory, you buy a higher quality product at, at a good price. So they, they s- there’s an expression that good design doesn’t cost more.

[00:10:23] Nathan: Mm-hmm.

[00:10:23] Chris: It’s the, uh, it’s bad design that costs more, ’cause it doesn’t work.

[00:10:26] And so what you’re paying for is the idea, but the manufacturing- The amount of plastic or wood that goes into a product’s literally the same, so you don’t have to reinvent all that stuff.

[00:10:35] Nathan: Right. Yeah, it’s interesting, as it goes back to identity, as you’re talking about, like, what kind of person shops in each place or, or all of that.

[00:10:42] Thinking about Kit as a brand, something that we’ve tried to do a lot of is … Some of the other players in the space are very much about, like, make money online. Like, it’s starting to get into some get rich quick vibes.

[00:10:54] Chris: Mm-hmm.

[00:10:55] Nathan: Right? And we’ve alway- obviously, email and a newsletter is a fantastic way to make money, but you’ll never hear us say, “Make money,” you’ll always hear us say, “Earn a living.”

[00:11:04] Right? Or you’ll … We’ll always talk about the value provided, right? As a c- as a creator on Kit, all of our messaging is about you serve your audience, and then you’re taken care of as part of that, rather than, like, your audience is a, an ATM, where it’s when you just need some money, you launch something and, and go from there.

[00:11:23] Yeah. ‘Cause I always think about Seth Godin’s line of, like, “People like us do things like this.” And so really trying to differentiate a Kit creator from any other platform.

[00:11:33] Chris: Yeah. It, it’s hard. When you start to sell into, excuse me, wealth-

[00:11:37] Nathan: Mm-hmm …

[00:11:38] Chris: then you’re on the second tier. You should strive to move towards status and identity.

[00:11:43] Nathan: Mm-hmm.

[00:11:44] Chris: And so there’s the five whys. Why do you do something? And if you keep asking that question, you’ll find a commonality between the people who are your customers and the people who are not. And so people sell features usually, then they move to benefits, which may be what you’re talking about, which is earn a living.

[00:12:00] Right. But then we would need to tor- move towards meaning. So it’s like why is it important for you to earn a living?

[00:12:06] Nathan: Because you need to take care of your family.

[00:12:08] Chris: That would be one. What else?

[00:12:09] Nathan: Yeah. Uh, anything you wanna buy. Uh-

[00:12:12] Chris: Okay …

[00:12:12] Nathan: home, so yeah.

[00:12:13] Chris: Yeah.

[00:12:14] Nathan: All those things.

[00:12:14] Chris: Yeah. What else? Anything else?

[00:12:17] Nathan: Uh-

[00:12:17] Chris: Why do we need to earn a living?

[00:12:19] Nathan: Uh, I-

[00:12:19] Chris: And sometimes there are not always good reasons, by the way. Sometimes- Yeah … they’re bad reasons, and it’s, it’s a good reason that is bad, but …

[00:12:25] Nathan: A good reason that is bad.

[00:12:26] Chris: Yeah.

[00:12:27] Nathan: Our whole society runs around money, and so needing The, I mean, that is, that is the currency that everyone- Yeah … operates in.

[00:12:34] Chris: Yeah. So we could say something like, mm, make your ex regret

[00:12:39] Nathan: leaving you. Right.

[00:12:41] Chris: That could be a reason. Show up- That’s a bad reason. That’s a good reason.

[00:12:44] Nathan: Yeah. Right? Show up to your 10-year, 20-year high school reunion driving some fancy car, and everyone’s like, y- you know.

[00:12:50] Chris: Yeah. Right.

[00:12:51] Nathan: You know, trying to prove someone wrong or whatever it is,

[00:12:54] Chris: right?

[00:12:54] That’s

[00:12:54] Nathan: right.

[00:12:55] Chris: So we have to look at people’s motivations, like, uh, prove your brother-in-law wrong.

[00:12:59] Nathan: Mm-hmm.

[00:13:00] Chris: Or maybe, um, go on that dream vacation-

[00:13:04] Nathan: Right …

[00:13:04] Chris: that you’ve always wanted, and stop- And, yeah … stop cutting coupons.

[00:13:07] Nathan: Right.

[00:13:08] Chris: I mean, there’s a lot of different human motivations, so we can say we’re gonna earn a living, and in specific campaigns- Mm-hmm

[00:13:14] you can talk a little bit more about this deeper idea, right? ‘

[00:13:18] Nathan: Cause there’s a huge status element-

[00:13:19] Chris: Yes …

[00:13:20] Nathan: to what, what you spend, right? Especially now with social media, where the… It’s the vacation for a lot of people is not actually about am I enjoying the time and the moment where I am. It’s about do I have the right photo to post to signal- Mm-hmm

[00:13:36] that I’m the kind of person who can spend a month in Bali doing, you know, doing whatever, to then get me the brand deals so that I can, you know, whatever else.

[00:13:45] Chris: Yeah. I, I think that is a different kind of status- Okay … that is pretty hollow.

[00:13:51] Nathan: Yeah. Okay.

[00:13:51] Chris: And, and we know that, so it’s like, uh, the joke is like, um, did you work out today if you didn’t post on social?

[00:13:58] Of course you did, but, you know, we gotta make sure everybody knows that we’re at, um, the box gym or whatever- Right … and we, we’re doing what we need to do. So can I get back to one of the questions- Oh, yeah … you were asking about- Do it … like a lot of people working on their personal brand and it’s not going anywhere?

[00:14:10] Nathan: Yep.

[00:14:11] Chris: I’d argue they’re not working on their personal brand at all.

[00:14:13] Nathan: What are they working on?

[00:14:14] Chris: They’re working on their marketing funnel, calling it a personal brand, ’cause everything put out is a disguised, not well disguised ad for a product or service they sell. And this is what they do, because they follow and emulate what everyone else is doing.

[00:14:28] Nathan: Mm-hmm.

[00:14:28] Chris: E- every piece of content is a pitch to, like, “And if you want my downloadable, if you want this, you want that.” It’s always that. In order for me… Okay, let me step back.

[00:14:38] Nathan: Yeah.

[00:14:38] Chris: Um, personal brand and the word brand has become quite popular. I think marketing’s great. I think sales is great. I think funnel design’s great, but it don’t sound that sexy right now.

[00:14:48] And so those same people have decided to call it this n- new buzzword, which is personal branding. Yep. They’re, they’re really te- just teaching you conversion design, learning how to do the customer journey, about how to run marketing campaigns. It’s really not about personal brand. But I find that the vast majority of people who speak about personal brand, the 99.9% of them are in this space where they’re really just using the words advertising, marketing, funnel design, conversions, and they’re using the wrong label.

[00:15:18] Nathan: Okay. ‘

[00:15:18] Chris: Cause maybe they’re ashamed of what they do- Right … or they’re just chasing the next buzzword. So in that church of personal branding, I am an outlier. I’m a blasphemer. I’m the Antichrist. Yeah. Okay? This is who I am because I’m thinking personal brand is about who you are, understanding your voice in this world, your values, and being able to communicate that.

[00:15:37] It’s devoid of you trying to make money And so I think they’re going on one pursuit without understanding what that pursuit is. Yep. They’re executing the wrong plan, following the wrong leaders, and, and that’s really the problem. People come to me in my workshops, it’s personal branding. They’re like, “Chris, how do we sell more?”

[00:15:54] Yeah. Like, man, I’m sorry, friend, there’s no refunds, but that’s not what we’re gonna do here. We’re gonna get into your shadow work, we’re gonna understand your voice phrase, understand who you are in this lifetime, lean into your vulnerabilities, and to be able to be able to surface them and share them with the world because right now you’re just masking.

[00:16:11] Nathan: Well, so that’s something I wanted to ask about- Yeah … is that a lot of people think that personal brand is about what they post, right? And I’ve heard you say that, like, all the real work in personal brand is internal.

[00:16:22] Chris: It is.

[00:16:22] Nathan: Like, w- and you, you mentioned shadow work, you mentioned- Yes … like, what do you…

[00:16:25] Let’s dive into that. What do you mean?

[00:16:26] Chris: Well, all right. Oh my gosh. This is gonna be a juicy episode. You said we we’re not gonna go that deep, but we’re gonna go real deep, okay? I think there’s this period in your lifetime, I would guess between three years old and nine, that you are who you really are- Okay

[00:16:39] in this lifetime. And through a lot of socializing and conditioning, that person is washed away and you become very homogenized with society. I’ll give you example. Let’s say you like to pick your nose. I know I’m saying that’s who you are, that’s not your identity, but that’s what you do. And somebody say, “Eh, that’s gross.

[00:16:56] Don’t do that.” And then you talk really loud. Let’s use our inside voice. So the entire process of growing up into adulthood is someone shaving off all the edges and- Yep … sanding you down until you’re this, like, shiny river stone. Cool. Or river rock. And then you get out into the world, and then you enter a next phase, which is, “I’ve finished college, I’m going to work.”

[00:17:16] Guess what? We wear the corporate uniform. It’s jacket and tie. It’s only casual Fridays. “This is what you need to do. This is how you say things. This is how you move up in the world.” So we’re very much trained by society to fit into a very specific box. And we’ve learned very early on if we’re different, we’re weird, and we’re doing things, they label you weird, different, a freak.

[00:17:35] Yeah. “Get away from me, freak.” Right? Yeah. Like, if you’re into chess and everyone’s into football, they’re like, “You’re a nerd loser,” and they’ll say much, m-

[00:17:43] Nathan: Much

[00:17:43] Chris: nicer things than that … less nice, yeah, much worse things. Yeah. Oh, yeah, they’re gonna be horrible. And all you’re searching for is belongingness.

[00:17:48] Mm-hmm. The relationships, third tier, and you’re like, “This is terrible. I don’t wanna do this. This is too painful for me,” because you don’t have identity yet. And so you keep pretending to be someone long enough, and you forget who the real you is. So m- my task, I think my purpose in this life, is to be able to help individuals like yourself remember who you were.

[00:18:11] Mm. ‘Cause this is the pursuit of your lifetime. And to be able to lean into all that stuff that you thought was so weird that you’ve put it away into a little box, and you hid it into the attic of your mind, and you never look at it again. So much so that it scares you to see it. It really does. We’re so trained to make other people happy, to fit in, that we don’t know what it means to be ourselves anymore.

[00:18:33] Nathan: So y- yeah, you talked about how, um, how everyone’s born weird, right? There’s all those-

[00:18:38] Chris: We’re born us. We’re labeled weird. Y-

[00:18:39] Nathan: yeah, exactly.

[00:18:40] Chris: Yes.

[00:18:41] Nathan: So what, what does it look like first to do the work to bring that back out- Yeah … and to be like, “Oh, I actually don’t need to, uh, dress the same, act the same”- Yeah

[00:18:50] like grab for belonging wherever, you know, someone might offer a single shred of it. And then, like first to do that work, and then second to actually show that outwardly when it comes out in something like brand or the things you’re standing for.

[00:19:04] Chris: Here’s the, here’s the interesting thing. How, how… Do you mind me asking how old you are?

[00:19:07] Nathan: I’m 35.

[00:19:08] Chris: Very young man, 35 years old. About to turn

[00:19:10] Nathan: 36.

[00:19:11] Chris: Damn. 35. I’m 54, so we invert the ages a little bit. You’re just still a year younger than me, which is not cool. I’m just gonna say that. Okay. Do you feel like you know who you are, your identity?

[00:19:23] Nathan: Um.

[00:19:25] Chris: Can we get r- vulnerable?

[00:19:26] Nathan: Yeah, we can do that. Let’s go.

[00:19:28] Chris: Chelsea’s looking at me like, “Oh, God, go here.”

[00:19:30] Nathan: Chelsea, I like

[00:19:31] Chris: it. The fourth one, but ask him this. Yeah,

[00:19:32] Nathan: exactly. Yeah. So let’s do it.

[00:19:35] Chris: I’m asking the questions now.

[00:19:37] Nathan: Yeah, you’re in charge.

[00:19:38] Chris: Yeah.

[00:19:38] Nathan: Do I feel like I know who I am?

[00:19:40] Chris: Yeah.

[00:19:41] Nathan: Um, I- it’s a constant thing that I’m working on.

[00:19:44] Chris: Okay.

[00:19:44] Nathan: Um, but I know a lot of things that matter to me.

[00:19:49] Chris: Okay. That’s an interesting way of you answering that question. What percentage of knowing this do you think you’re at? ‘Cause you’re like, “I’m trying to figure things out.” Oh. I know it’s impossible to say- Yeah … but what percentage do you think? I mean,

[00:19:58] Nathan: I feel like, so it’s one of those things where, uh, so I’ve- my, my oldest is a teenager now, and so it’s always thinking about, you know, like, no one knows as much as a teenager, right?

[00:20:09] Yeah. You know? And so we’re in that phase of watching it. And so I feel like the more I know, or the more I understand, the less I know. Yeah. And so, I don’t know, we’ll say 20, 25%.

[00:20:17] Chris: Okay. Yeah. That, that’s a fair number.

[00:20:19] Nathan: Yeah.

[00:20:19] Chris: Okay. And so as you’re searching for this, and I’m curious if there was a life event that happened- Mm-hmm

[00:20:24] where you started to feel more yourself.

[00:20:27] Nathan: Yeah. I, I got shingles. Got super- Oh … um, at, how old was I? 24. And,

[00:20:34] Chris: uh- That was like last year. Keep going.

[00:20:37] Nathan: And, uh, yeah. And then I ended up, I had all of my identity tied up in what I had accomplished.

[00:20:44] Chris: Okay.

[00:20:45] Nathan: And I was very good at what I did, right? Mm-hmm. And so, you know, I was 24 making a quarter million dollars a year.

[00:20:52] I had an audience, I had all these things, productive, all of that. And after getting shingles, uh, and being on painkillers from that, I lost my ability to work. Oh. And I would sit down at my computer and my brain would just not function. And I talk a lot about, like, flywheels and virtuous cycles. Mm-hmm. Uh, everyone forgets those spin the other way, too, right?

[00:21:14] Yeah. There’s, there is a vicious cycle there.

[00:21:16] Chris: Mm-hmm.

[00:21:17] Nathan: And I had so much of my, of my identity tied up in- what I could accomplish.

[00:21:21] Chris: Mm.

[00:21:22] Nathan: That when I would sit down and couldn’t get a task done in front of me, then it just spiraled from there. And, and so the worse I felt about myself, obviously, the the, the wor- worse I performed and all that.

[00:21:36] Mm-hmm. So I ended up spending at least six months, like, deeply depressed, and then, and it probably took me two years to come out of it.

[00:21:45] Chris: Okay.

[00:21:45] Nathan: Yeah.

[00:21:46] Chris: That’s real interesting.

[00:21:47] Nathan: That was a, that was a transformative moment.

[00:21:49] Chris: Not the answer I expected, but a good one. Yeah.

[00:21:51] Nathan: Okay.

[00:21:51] Chris: A really good one because a lot of people, and I, I would say, like, oftentimes men more-

[00:21:57] Nathan: Mm-hmm

[00:21:57] Chris: um, we form our identities around the things we do, our utility into the world. Yeah. And the, and society- So I’m a bad guy … tells us this, right? Yeah. It’s like you are more attractive as a potential mate in- because you’re more useful. You, you have more utility.

[00:22:11] Nathan: Yep.

[00:22:11] Chris: And so you don’t have to be the smartest or the best looking.

[00:22:13] You,

[00:22:14] Nathan: you can make money. You

[00:22:15] Chris: can- But if you can do things …

[00:22:15] Nathan: remodel the house.

[00:22:16] Chris: Yes. You can do whatever else. You can fix the toilet. Yeah, exactly. It’s basic things. And unclog the drain.

[00:22:20] Nathan: Right.

[00:22:20] Chris: You’re useful, and that’s what we identify as. And so when you strip that away, your job, your title, well, who am I? And that becomes a real dilemma.

[00:22:30] I’ve noticed that people, as they get older, and men, again, when they retire and they don’t do anything anymore, their life value, their life force starts to diminish really fast.

[00:22:40] Nathan: Oh, yeah.

[00:22:40] Chris: They have no more purpose, and they haven’t developed, like, real hobbies or real relationships. A lot of entrepreneurs when they

[00:22:45] Nathan: sell their companies end up-

[00:22:46] Chris: They’re lost

[00:22:47] in this

[00:22:47] Nathan: place, yeah.

[00:22:47] Chris: Right. And, and they will start to deteriorate their health. I, I’m seeing it in my own father, kind of watching it in somewhat real time, is that once he retired, his body’s starting to fall apart. I’m like, “Dang, what happened?” Yeah. ‘Cause he was this vital person who would like, “I, I’ll fix this, I’ll carry this,” and now he’s a lot weaker.

[00:23:03] I know that’s just part of aging, but I think he’s lost a little bit of his purpose and his identity. And this is why I think it’s so important to figure out who you are, okay? And so a lot of times people will say, “I wanna work on my personal brand.” I’m like, “Well, who are you?” “Well, I’m the plumber,” “I’m the electrician,” “I’m the computer science guy.”

[00:23:19] I’m like, “No, no, no, not what you do. Who are you?” Mm. It’s a question that we’re afraid to answer because we don’t know. It’s like staring into the void, and that unknowingness creates great anxiety within us. But I think that’s a pretty good sign to go and shine the light on the darkness to see what’s there.

[00:23:36] So outside of you running your company, winning your awards, the accomplishments and the, the zeros you’ve added to your account, who are you? Who are you in this lifetime? Uh, I always screw this part up because I mix the two. And usually when I’m doing a presentation, it’s this Picasso quote. Of course, one of my favorite artists of all time, like, a, a, like a real maverick person in being able to do what he does, said something like this: “Purpose of life is to discover your gift, and the meaning is to give it away.”

[00:24:04] The meaning of life.

[00:24:05] Nathan: Hmm.

[00:24:06] Chris: So we have to figure out what our gift is. And we think it’s something we have to invent or to find, but I’ll add to that quote saying, “You are the gift.” I believe each and every single one of us is born by design or by divine being to have a unique combination of things that make you really powerful.

[00:24:25] But what we do is we forget those unique, interesting things, and then we conform to what everybody else is doing. So we’re purposely handicapping ourselves. I’ll give you an example. My nephew, he’s autistic, and when he, when we’re… We didn’t know at the beginning ’cause he was like, hmm, he’s not looking at me.

[00:24:41] There’s some interesting behavior going on. Or he’ll come up, he gives you a weird sideways hug. He doesn’t really touch you. Hmm. So there’s some kind of physical challenges there. Or he’ll punch you. I’m like, “Bro, what are you doing?” Uh, you know. But once- Yeah … we knew he was, he was autistic, we’re like, okay, we can talk to him very differently.

[00:24:58] And it turns out, like recently, he and his friends won a math champion- or they, they came in second place in the, like, district championship at math. I’m like, damn. So if we measure him against what society considers normal and good and virtuous- Right … he’s doing terrible. Yeah. But if we just look at he’s really into science, he knows all the planets and geography, and he’s really freaking great with numbers, I’m like, yeah, that’s his gift.

[00:25:21] And so the, the job, the duty of all parents is to forget about what you want and what you didn’t accomplish in your life. Stop trying to live vicariously through your children. Stop fixing your mistakes through them, but to honor them for who they are and to say like, “I need to support whatever this is,” and not to have any preconceived ideas.

[00:25:39] And I think that’s the beautiful part, and that’s the challenge of parents to say, “I had ideas of success for my children.” Mm-hmm. “I gotta let that go because they get to live their life. I had my shot, and I need to break the cycle.”

[00:25:51] Nathan: Right. How do you answer that question for yourself, of who are you?

[00:25:55] Chris: Don’t turn to…

[00:25:56] I’m asking the questions Yeah. What are you doing? Um- Well, we’ll take a turn right about- Who am I? Uh, I see my identity as a person who’s, who is, who observes things-

[00:26:06] Nathan: Okay …

[00:26:06] Chris: and, and thinks about ’em. Maybe not as profound as S- Seth or Seth Godin or someone else. Right. But I think about things, and I, I, I, I want to be able to express these ideas in as many forms as I want.

[00:26:18] Mm. Sometimes it helps people, sometimes it does nothing for them. But I’m on this pursuit of being the artist, and it’s an identity I’ve denied myself for a really long time because I’m a designer, and there’s a big difference between design and art. Mm. But now, as I’m creating content, I do it for myself.

[00:26:36] Really

[00:26:36] Nathan: interesting. And what, what’s the difference between design and art?

[00:26:38] Chris: An, an artist, and I, I love this, art is a invitation to look at the world from a different perspective. Mm. And ar- artists have emotions and feelings about things. They create it, whether it be music or sculpture or painting, and if you experience a similar emotion, it’s good art.

[00:26:53] Nathan: Okay.

[00:26:54] Chris: So if we look at it like that. Design is, is a process of achieving an outcome for a specific goal. So it’s not about what I want to say about the world. It’s like, you have a problem, I need to solve that problem. You’re trying to get this kind of customer, or you’re trying to create this kind of feeling in your brand.

[00:27:09] This is what I try to design for you. The mistake that designers make is they think they’re artists. It’s about my vision, my perspective, and that’s very egocentric. I’m trying to help you solve a problem. And so as a guide to a, an ultimate outcome, I have my opinions, but- Mm … it doesn’t really matter. It matters what you feel and think and need.

[00:27:29] Because at the end of the day, I move on, and you have to live with the things I create. So if I create a really bad interface, I use colors that are not legible, your sales tank, and I walk away thinking, “That was my perspective in the world.” Right? Yeah. There’s a price to pay for being an artist. There’s financial uncertainty.

[00:27:47] There’s no guaranteed outcomes, and you often will suffer for your art. In the world, there are many artists. There are very few successful artists.

[00:27:54] Nathan: Mm.

[00:27:55] Chris: And there’s a big difference there.

[00:27:57] Nathan: And, and so you’re seeing art as that. You said the- Seeing a certain perspective- Yeah … and then basically an invitation to, to show other people that same perspective on the world they may not have seen otherwise.

[00:28:09] Chris: Yeah. It, it’s an invitation for you to look at the world from a different perspective. From a different perspective. Yeah. So when we, when we move f- uh, away from the realistic, uh, like, paintings from Caravaggio- Mm-hmm … and we move into the world of Van Gogh, it is a totally different way of looking at the world, right?

[00:28:25] And if we take a Van Gogh painting and we turn it into a three-dimensional experience that you walk through, and you can literally walk into a painting, that is asking you to look at the world from a different point of view. When we listen to music or we watch a film that transports us another place in time and person, they’re bringing us to look at the world from a different point of view.

[00:28:45] So my, my goal, and I, I think about this, and I’m still trying to figure out how to say this part, but I think you have two priorities in life. Your first priority is, uh, to be true to yourself. Mm-hmm. And your second priority is to refer to priority number one. And so my whole thing is if helping you, making you happier requires me to not be my truest self, then I’m not interested in that at all And this is a hard thing for, for people to hear because we’ve been trained to believe the opposite, is like we, we have to look out for people.

[00:29:17] You, you’re lacking empathy or sympathy. And I think I serve more people, especially myself, when I am myself.

[00:29:23] Nathan: Mm-hmm.

[00:29:23] Chris: And I have many examples. If any of it becomes interesting to you, we can talk about that and pick that apart. But I’m trying my best to just be my truest self.

[00:29:32] Nathan: Mm-hmm.

[00:29:32] Chris: And so whatever that comes across, some people listen to this and say, “This guy’s full of himself.

[00:29:36] He doesn’t know what he’s talking about. He’s too aggressive, he’s too direct.” Some people say he’s really charming, interesting, a breath of fresh air. I don’t really care either way. I just need to be me.

[00:29:45] Nathan: Right. I think that, I don’t know if this is to the level of, like, identity or something like that, but what I, when I think about the gift that I wanna bring to the world, I, I think similar to you, I grew up in an environment where money was very scarce.

[00:30:01] And the amount of pain and anxiety and everything else that comes from that is, um, you know, people say money doesn’t buy happiness, and I’m like, “I don’t know.” Like, lack of money definitely, uh, causes-

[00:30:15] Chris: Right …

[00:30:15] Nathan: uh, some negative side effects. So somewhere in the spectrum, like- Yeah … money can be a positive thing.

[00:30:20] And I, maybe from a observing the world perspective, like, I look at things from almost like a physics perspective of like, why, why did this business work? Why does this job get paid more money? Why, like, why do all of these things play out in a certain way? Why do recurring revenue businesses sell to private equity for more than, you know, one time for, like any of those things.

[00:30:41] Yeah. Right. And what I’ve realized is anyone else who’s built up a company has as well, is that there’s observable concrete things and concrete steps that you can do. And I feel like my mission in this life is to map that out for people so that they don’t have to go through the same level, level of pain and suffering.

[00:30:59] You look at, like, one of the single biggest reasons that, like, relationships fail, it’s like conflict over money and all that. And you’re like, what if that just didn’t have to be a thing? And so when I think about the impact that I wanna have on people and, and, and all of that, is I want to make as many of these things known.

[00:31:16] Like, I, I want to explain the laws of physics- Mm … so that you go, “Oh-”

[00:31:20] Chris: Yep … ”

[00:31:20] Nathan: I just needed to do that, and now, you know, money doesn’t have to be a point of stress for me,” you know, and, and all that. And so that’s the thing that, um, I try to do as much as possible when, like, my identity or my brand or, or all of that is…

[00:31:39] Or my, my gift to the world would be how do I make that as clear and as understandable as possible?

[00:31:45] Chris: Mm-hmm.

[00:31:45] Nathan: Um, and like that’s my way of being of service to others.

[00:31:48] Chris: Mm-hmm. I like that. Well, I, I think you provide, um, uh, tools that have served you, but it happens to serve a lot of other people.

[00:32:01] Nathan: Right.

[00:32:01] Chris: You could have chosen a lot of different things to make in this world, and this is what…

[00:32:05] I mean, sometimes I think about this. Did you choose your job or did the job choose you? Never sure. And it, it, and I think- Yeah … a lot of times you thought you made that decision because free will’s an exciting idea, but maybe that was your calling. Who knows? But you’re still very young. You could kind of restart two more times and still- Right

[00:32:24] be like, “Oh, this is what I was meant to do.” Yeah. I’ll give you the example. So from my 20s onto my 40s, I thought my purpose was to make commercials and music videos and improve the world by making aesthetic things, especially in the motion space, right? And then I found that towards the end of that arc, I didn’t get any more joy from doing this.

[00:32:46] The, the challenges got bigger, the budgets got bigger, and, uh, the consequences of making bad decisions got bigger, but it’s like I don’t enjoy this really. And then I realized the whole point was to make money. I just did it to make money. It just… I found- Okay … a gift that I did, I was able to do this i- with less effort than most people, so I got to reap the rewards of that gift.

[00:33:10] But now I’m faced with this idea, like, I don’t need to make more money. What do I need to do? And that sent me into kind of an inner journey-

[00:33:19] Nathan: Yeah …

[00:33:20] Chris: about what it is that I want to do with my life. And it was by accident I found content creation as a, as a form. So some, some people’s art is expressing through music, through physical things.

[00:33:31] My art is, like, words and ideas. Mm. And I just want to keep working on that.

[00:33:36] Nathan: Yeah. That makes sense. We’ve talked a lot about what you stand for, right? And, and both in brands or who you are as a person. Something I’ve heard you talk about in your content is, like, what you stand against-

[00:33:48] Chris: Yes …

[00:33:48] Nathan: and how people are often very afraid.

[00:33:50] Like, it’s safe to say, “I stand for this,” you know? Yes, it

[00:33:53] Chris: is.

[00:33:53] Nathan: Like, all the things that we’ve talked about, no- no one’s gonna listen to that and be like, “Oh, those, those assholes,” you know? Right, right. That sort of thing. But standing against something, that, like, actually, one, it differentiates the brand, but two, like, it’s, it’s risky.

[00:34:07] Like, how do you think about that, and how do you encourage brands to think about it? Yeah.

[00:34:10] Chris: Or, or

[00:34:11] Nathan: individuals more so than brands.

[00:34:12] Chris: It’s less risky than we think.

[00:34:14] Nathan: Okay.

[00:34:15] Chris: It’s something like, uh, and I, I, I’m, I’m not gonna tell you who the original person said this or the exact quote. I’ll just share an idea that’s not mine, which is nothing unites people more than a common cause.

[00:34:26] Nathan: Mm-hmm.

[00:34:27] Chris: So if we can hate the same things, it’s pretty cool, and we can see this play out in real time in politics right now, that it seems less about what we stand for but, but what we stand against.

[00:34:38] Nathan: Right.

[00:34:38] Chris: And there’s something very unifying about this. Both there are good parts and bad parts to this. Most companies or individuals will say, “I stand for freedom.

[00:34:46] I stand for equality.” I’m like- Right … “Yeah, cool, cool. Bro, so does everyone else.” Or it’s like Enron

[00:34:50] Nathan: having the values of integrity, honesty, or whatever-

[00:34:52] Chris: Yes …

[00:34:53] Nathan: and you’re

[00:34:53] Chris: like… Like Enron? Okay. Yeah. So it winds up being these empty platitudes.

[00:34:58] Nathan: Yeah.

[00:34:58] Chris: So if you stand for something that no one can disagree with, then do you stand for anything?

[00:35:03] Mm. Probably not. So then we say, like, what’s the opposite of that? So if you’re trying to make sure people have safe drinking water, cool. We believe in that.

[00:35:12] Nathan: Yep.

[00:35:12] Chris: What’s the opposite of that? Well, disease, safety, um, and all kinds of things. Like when we don’t have proper hydration or nutrients in our body, then we’re dealing with the first tier, which is health.

[00:35:25] Nathan: Mm-hmm.

[00:35:26] Chris: And we wanna move people along because I believe if my neighbors, in the broadest sense of that definition, are doing better, the world’s a better place. It’s safer. It’s like when they don’t have more want, then my family and the people I care about don’t have to worry about people taking things away.

[00:35:43] Nathan: Right.

[00:35:44] Chris: And it’s better this way, yeah? Uh, so I, I, I tell people, “If you wanna develop your personal brand, A, you need to know something, uh, your, what your keyword is. Like, the, what you want to be associated with. So when people think of this word, they think of me.” Okay. This is really important, okay? Yeah. So they think of this, and they think of me.

[00:36:04] And then, then on the opposite side of that is: Who is your nemesis? What are you trying to rid the world of? It’s like when you go to sleep at night, what is the thing that bothers you about the way things work? And it doesn’t have to be a person. It probably shouldn’t be a person. An idea, a process, a system- Mm

[00:36:22] something like that. And you need to be able to articulate that, and they have to work against what you wanna be known for. These are really important components. And somebody had recently debated with me, “Well, I don’t like this idea. It seems so American or antagonistic, or it seems so aggressive to have an enemy.

[00:36:40] I wanna do this without it.” You can This is not what I teach- Right … and this is not what I’ve been able to observe. Probably

[00:36:45] Nathan: won’t resonate to the same extent.

[00:36:47] Chris: I think so, and I think of the strongest brands in the world, they have a pretty clearly defined mission that they’re on. They’re trying to achieve this result while getting, or getting rid of something else.

[00:36:57] So if there’s a program to feed children, what are they trying to end? Probably poverty.

[00:37:02] Nathan: Yep.

[00:37:03] Chris: Right? That, that seems to make a lot of sense. And as a comic book nerd myself, I’ve observed this, and you might have a different perspective on this, is who are the most enduring popular superheroes? You can probably name a few.

[00:37:15] Yeah. Who are they? Batman, Spider-Man. Batman, Spider-Man. There’s a lot of man in here- Yeah … but yes.

[00:37:19] Nathan: Exactly.

[00:37:19] Chris: Yeah. And, and, and maybe even Superman. Yep. Okay? So from the DC Universe, this is kinda wild, they have some of the most iconic characters. They’re just designed really well, and it seems like more of the world knows about the DC characters-ish.

[00:37:33] Mm-hmm. And then Marvel is, like, more successful, doesn’t have the same- Right … iconic characters. It’s really weird. Okay, here’s my observation. The reason why heroes are the heroes that break through the, the threshold or, or into, like, our consciousness is they have great enemies.

[00:37:54] Nathan: Hmm.

[00:37:55] Chris: So who’s, who’s Batman’s enemy?

[00:37:57] Nathan: The Joker.

[00:37:58] Chris: The Joker.

[00:37:59] Nathan: Yeah.

[00:37:59] Chris: Uh, the, probably his primary- He’s the go-to. He is a lot. The Joker. He has a rogues’ gallery. And, and in fact, when you think about it, when the creators of these characters d- build their world, the better the enemies, the better the hero. ‘Cause the hero needs to fight for something.

[00:38:13] Nathan: And it’s even bigger than the individual enemy. It’s the, it’s the, you know, what Gotham has become. Like, the, the crime, the-

[00:38:19] Chris: Yeah …

[00:38:20] Nathan: like-

[00:38:20] Chris: The city is a character in- Is a, yeah … in this whole thing, and that is also part of the personal brand. So when we look at Batman, and we look at the design of the Joker, there’s something interesting about this.

[00:38:31] Batman’s a billionaire.

[00:38:32] Nathan: Mm-hmm.

[00:38:32] Chris: Uh, he had a tragic beginning. Uh, he’s a, a kind of a physical specimen. He’s, uh, the world’s greatest detective, so he’s not only smart, he’s strong and rich.

[00:38:43] Nathan: Mm-hmm.

[00:38:43] Chris: Uh, you know, like the joke in the movie was like, yeah, billionaire th- philanthropist, what’s your problem?

[00:38:48] Billionaire playboy philanthropist, what’s your problem, right? Who’s the Joker? The Joker w- is, is a mysterious origin. He’s a criminal. He’s chaotic. And he’s intellectually superior to Batman, but physically inferior. Mm-hmm. So these heroes and these villains tend to be the equal and the opposite of each other.

[00:39:09] It’s like I’m a big fan of the yin-yang symbol. Mm-hmm. Equal and opposite, they’re balanced. So if you look at Superman, his biggest enemy is Lex Luthor. He’s an alien, he’s human. He’s strong, he’s dumb as a brick Lex is a genius

[00:39:23] Nathan: Right. He’s

[00:39:24] Chris: weird … and rich. Yeah. And he’s physically very weak. So this is kind of, kind of interesting.

[00:39:29] So when we look at world building, we look at the two characters. They’re not separate. They’re part of the world.

[00:39:36] Nathan: Mm-hmm.

[00:39:36] Chris: So when we look at the world of you, your brand, you have what you perceive as your strengths, but you also have the shadow side, which is the part that we hide. And so if I were to tell you the Blue Beetle…

[00:39:47] Can you name the Blue Beetle’s enemy?

[00:39:49] Nathan: No.

[00:39:49] Chris: I couldn’t either, ’cause I don’t know. That’s the problem.

[00:39:52] Nathan: Right.

[00:39:53] Chris: So sometimes they overpower someone, and then they don’t give them a strong counterpart. They’re constantly foils to each other. So in the world of fiction, these two components build that world. You take away one, it becomes much weaker.

[00:40:07] Nathan: Mm-hmm.

[00:40:08] Chris: So what I try to help people do is look into your shadow self, the things that you feel great shame or guilt or anxiety around and you’ve been hiding for a really long time, ’cause you feel the world will not accept you. Once you accept that, the world will love you. And it’s hard, deep work, Karen.

[00:40:25] Nathan: Mm-hmm. Okay, so if we bring this into a personal brand, like, and talking about what you stand for Yeah. Is there an example that comes to mind or, or an individual who’s done this well where they say- Yes … “This is what I stand for, and this is what I stand against”?

[00:40:39] Chris: Yes, yes, yes. And it’s not like… And people are like, “Do they have a team,” right?

[00:40:43] I’m like, “No.” They exist, and their belief systems drive their words and their actions, and we start to see it. And the people who are very consistent at doing this, and they’re not trying to do 1,000 different things, it becomes very easy for us to see. My favorite example is Bryan Johnson. Yeah. He’s the most measured man, right?

[00:41:03] Nathan: Right.

[00:41:03] Chris: He’s a pretty radical millionaire, billionaire. I don’t know how much. He’s got a lot of money. He is trying to live longer.

[00:41:09] Nathan: Mm-hmm.

[00:41:09] Chris: But not just live longer. So we can say, like, what is the key word he wants to be associated with? What would you say?

[00:41:15] Nathan: Longevity.

[00:41:15] Chris: Longevity.

[00:41:16] Nathan: Yeah.

[00:41:16] Chris: Or aging reversal.

[00:41:18] Nathan: Yeah.

[00:41:18] Chris: Something like that. So naturally, what is his enemy?

[00:41:21] Nathan: Time.

[00:41:22] Chris: Time, or you might say death.

[00:41:24] Nathan: Right, death.

[00:41:24] Chris: To keep it real simple.

[00:41:25] Nathan: Yeah,

[00:41:25] Chris: yeah. Yeah. He’s not fighting time. He’s fighting death. He’s just trying to cheat death.

[00:41:28] Nathan: Yeah. Well, I mean, his- Right? If you had a bumper sticker-

[00:41:31] Chris: Yeah …

[00:41:31] Nathan: it’s like, “Don’t die.”

[00:41:32] Chris: Don’t die.

[00:41:32] Well, that’s the third component to this three-part, which is you have what you stand for, you have what you stand against, and you have a line, a rallying cry, a tagline, something that unites these two things. Right. So “don’t die” tells you the enemy and what he stands for. We can infer all the meaning from that.

[00:41:49] Nathan: Mm-hmm.

[00:41:49] Chris: So when we… Uh, and I was asked this recently on a podcast, and I stumbled through it. I’m like, “Let me make up for that right now.” They’re like, “Well, Chris, what’s your triangle? What are your three components? What are you standing for?” Well, I, I, I don’t know a better word, and I hate this word, but I’m gonna say it.

[00:42:04] Like, truly authentic, a personal brand. Mm-hmm. That’s what I want to be known for, and the opposite of that is some form of masking. Mm-hmm. So then my tagline is, “Unblend yourself,” and that should explain those two concepts. Right. The cool thing is, the only part that people see is the bumper sticker part.

[00:42:25] But we can infer the meaning from that.

[00:42:27] Nathan: Right.

[00:42:28] Chris: And so these three things have to work in concert in my mind, otherwise it’s a two-legged table.

[00:42:33] Nathan: Okay, so if we workshop this, going back to my brand, um, and- Oh,

[00:42:38] Chris: it’s all about you.

[00:42:39] Nathan: It’s always all about me. No,

[00:42:43] Chris: I’m just kidding. It’s called The Nathan Barry Show.

[00:42:43] My God, the ego on this

[00:42:44] Nathan: guy. Yes. It’s, it’s incredible.

[00:42:46] Chris: Chelsea, I don’t know how you deal with this.

[00:42:48] Nathan: Yeah. What I’ve said is the, the mission for the company, and this is my individual mission as well, like, we exist to help creators earn a living. And so it’s very po- and every- it’s, it’s like we want clean water.

[00:42:58] Like, of course. Like, great. There’s, everything is positive about that. Yeah. Um, but there’s nothing in there that stands against. Um, and so I’m trying to think of where, where you would get to… I guess you, you’d, you know, you’d be against poverty, you’d be against, um, uh, like ignorance, right? ‘Cause a lot of the way that I believe you achieve is not working harder, it’s understanding the physics of-

[00:43:22] Chris: Your enemy could be burnout.

[00:43:23] Nathan: Yeah. It could be, yeah, burnout. Um, all of those things. But how else would you, would you think about that? Or, like, what questions- Well- … would you ask to draw out? This

[00:43:30] Chris: is excellent. Okay. What you do as a company is different than who you are.

[00:43:34] Nathan: Okay.

[00:43:35] Chris: So we have to do, like, a little palate cleanser and just forget that the company exists.

[00:43:39] Because over time you might be selling and buying companies- Mm-hmm … and you’re not gonna change who you are in that process. We have to figure out who you are and what you stand for, and the company is a mirror to this, but it’s not the driver of this. Okay? So my company’s called The Future. I’m not talking about past, present, or future.

[00:43:57] I’m not … I am just me. The company collects the residuals of me being me. And it’s a very different way of running a company or building a brand because it’s very founder-focused. Because people are like, “How do you differentiate between what The Future makes, posts, and what- Mm-hmm … Chris Do posts?” I’m like, “Well, I write whatever I want to write, I say whatever I want to say.

[00:44:17] And some team collects those parts, repackages it, and calls it The Future.” It’s not the other way around.

[00:44:23] Nathan: Mm-hmm.

[00:44:23] Chris: So I can’t… I have to emphasize this a little bit because people who are in real estate, people who are into Uh, investment, uh, or, or what is it called? Venture capital. Their whole identity is around moving money.

[00:44:35] It’s like, no, it’s not. There’s something bigger that you believe in, and there’s a story there that is connected to your origin that if you’re able to tell, then all the parts will make sense. W- why is it important for me to end this masking thing? Okay, ’cause first of all, I see a lot of suffering-

[00:44:53] Nathan: Mm-hmm

[00:44:53] Chris: in the world, and suffering is, like, probably lowercase S here. There’s this internal struggle in all of us that is fighting for control of who gets to live this life, the real you or the persona you’ve adopted, and it’s really hard to know which is which, especially if you’ve been living in the persona for a really long time.

[00:45:11] Why this matters to me is ’cause I, I’m a ref- refugee to America, uh, from Vietnam, and I grew up, English is my second language. I don’t understand the culture and the customs, and I’m in fights. I’m, I’m picked on, and so I retreat inward because I’m also an introvert And for a long time, I don’t have a voice, I don’t have an identity.

[00:45:32] Nathan: Mm-hmm.

[00:45:32] Chris: I’m trying to disappear. And so there’s a lot of healing that I had to go through, I had to go through to figure out who I’m supposed to be in this life. Some, some sadness, some depression, and once I worked my way out, it’s like I don’t want anyone else to go through that. Mm. That’s important to me.

[00:45:47] So over the course of however long I live, I might build different companies, different products, but they’re all gonna be a reflection of this philosophy. Mm-hmm. I’m just trying to help people self-actualize.

[00:45:59] Nathan: Yeah. I mean, and that’s how I feel as well. Yeah. Like, the, the, w- the company mission and everything else is just an expression of like, like, an outward expression of the things that I believe and the impact that I wanna have on the world.

[00:46:11] Chris: Yeah.

[00:46:12] Nathan: And that’s where I, I feel like I don’t resonate with so many entrepreneurs- Mm … ’cause they’re like, “Oh, I built this company, and I exited that, and I’m doing these other things, and I run all of these things,” and I’m like, “No, this company is, like th- how I plan to impact the world,” and that’s why I’m 13 years into one company, and in 10 years, I fully expect that I will be doing you know, it might have a slightly different shape-

[00:46:32] Chris: Yeah

[00:46:32] Nathan: but I will be doing basically the same thing-

[00:46:34] Chris: Yeah …

[00:46:34] Nathan: of helping people, um, yeah, reach their, reach their full potential and, and get to this point where they not only are having that financial impact for the- themselves and their family, but then it’s turning into something for-

[00:46:46] Chris: Yeah …

[00:46:47] Nathan: many more people.

[00:46:48] Chris: Do you, would you consider yourself as having some degree of self-awareness?

[00:46:52] Nathan: I think so.

[00:46:52] Chris: Okay. So if I spent a couple hours with you and asked you a couple of questions, and we weren’t being taped and all that stuff, I could probably help you surface this pretty quickly.

[00:47:01] Nathan: Mm-hmm.

[00:47:01] Chris: And, uh, and as long as you’re willing to tell the truth and understand- Yeah … a little, little bit about who you are, we can figure it out, and it’s like, oh, it’s a lot of these things, and eventually we find it, and you’re like, “Wow, I didn’t-” Mm-hmm

[00:47:10] “know that was there.” And so oftentimes we can see other people’s problems really clearly. Yeah. We can’t see our own thing. It’s very difficult. Yeah. Anybody who’s ever built their identity or messaging for their company, it’s the longest, hardest thing, and it usually sucks-

[00:47:23] Nathan: Right … ‘

[00:47:23] Chris: cause we’re changing our mind all the time.

[00:47:25] So one, one clue on this is, uh, a friend of mine, Blair Enns, said something to, to this effect. He says, “All strategy is autobiographical.” We dispense advice and strategies based on what’s worked for us.

[00:47:39] Nathan: Mm.

[00:47:40] Chris: Okay? You created something because you had a problem and you dealt with it. Right. Sometimes the problem is the problem, and sometimes there’s two layers deeper than that that’s the real problem.

[00:47:51] So through some ex- excavation, through some listening, through some empathy, we can find that problem pretty quickly. We can start to understand what motivates you, what drives you, and why you’re trying to correct for something that’s happened to you, some wrong that you’ve perceived in the world either done to you or that you experienced that you’re trying to make right.

[00:48:08] Nathan: Mm-hmm.

[00:48:09] Chris: As I say that, I can see your eyes looking somewhere, searching your memory banks possibly.

[00:48:13] Nathan: Yeah. I’m, I’m just thinking through, uh- Yeah, it’s, it’s basically… M- my biggest thing that I realized is how much I spent my childhood feeling like I was a burden on other people.

[00:48:25] Chris: Mm.

[00:48:26] Nathan: And so w- going through this arc of first, you know, hating that feeling and not knowing what to do about it-

[00:48:34] Chris: Mm-hmm

[00:48:34] at all,

[00:48:34] Nathan: right? And then becoming acutely aware of money and, you know, everything that came from that. How to, like, become self-sufficient, right? And so hearing Jason Fried from Basecamp say, “Making money is a skill that you can get better at with deliberate practice,” I heard that and like, I was like, “Wait, seriously?”

[00:48:55] Right? And so then it was like everything is within my, my power. And then spending really a lot of time in the, okay, my identity and my value and all of that is based on the money that I make, the impact that I have on other people.

[00:49:07] Chris: Yeah.

[00:49:08] Nathan: And the hard thing about that, you know, there’s a lot of hard things, but one of them is that then I found that I would do the inverse.

[00:49:14] Can I

[00:49:14] Chris: borrow your pa- paper? Okay, go for it. Okay. You mind if I… I know this is really weird. C- I… No, I wanna write in your notebook. I wanna map some of this- Okay … in case something comes out, all right? Is that okay?

[00:49:23] Nathan: Yeah, go

[00:49:23] Chris: for it. I- I know it’s weird. Never touch my notebook or my pen, but here we go. Okay, keep talking.

[00:49:27] Don’t… Ignore everything- Yeah, yeah … I may or may not be writing down.

[00:49:29] Nathan: And so what I ended up doing is I found that there were two people in my life that I deeply resented, and that was, uh, my stepdad and my younger brother. And the reason is that I perceived them both as, um, being burdens on my mom. And so like I watched my mom struggle with finances, all this, take care of all of us kids, you know, everything, and then like finally achieve her own, after my parents got divorced, like finally achieve her own independence.

[00:50:00] And, uh, she became a nurse, got her master’s in nursing, like got to the point where she was making, um, a really meaningful amount of money and all this, and like doing this into her like late 50s and 60s, and start a new career and, and doing all this. And then marrying someone who was a paraplegic. Um, my brother was still living with her, you know, like not getting a driver’s license.

[00:50:21] Like it was just a bunch of these things, and I’m like, you know, so, so frustrated at both of them, that like they took all of her time and attention. And because I, like I base so much value around like what you create, the independence that you have, not being a burden. There was something like, I don’t know, this is probably four years ago, five years ago or something, um, I realized that like- Like my mom’s gift to the world is to serve and to take care of people.

[00:50:47] And so I was d- like, as I deeply resented the people that she was, like, doing her greatest expression of love to take care of, probably the hardest thing for me is to then allow myself to be taken care of or to be a burden on someone else. And so, like, it’s this, like, full circle of where it’s like, yeah, I, I can achieve this level of in- independence, but then to get to the point where it’s like, oh, I, I have value outside of what I accomplish.

[00:51:12] I can allow myself to be taken care of by other people. I can fully exist, and I can fully accept people who, um, you know, like my stepdad, who, like, he needs someone to care for him, right? He’s, um, confined to a wheelchair, right? All of those things. It’s a long answer to and, and a bit of a ramble, but, um, that’s some of the arc that I went on.

[00:51:32] Chris: It’s fascinating. Have you shared this before?

[00:51:35] Nathan: Uh, a little bit. Not, not in detail.

[00:51:39] Chris: Uh, is your stepdad still alive?

[00:51:41] Nathan: No, he passed away, uh, four years ago.

[00:51:43] Chris: Oh, okay. The paraplegic?

[00:51:45] Nathan: Uh-huh.

[00:51:46] Chris: Have you said this prior to him passing away?

[00:51:48] Nathan: Yeah. Did- I was able to tell him …

[00:51:50] Chris: you told him?

[00:51:52] Nathan: Yep, in, uh, at his, uh, hospital bed.

[00:51:56] Chris: What compelled you to tell your stepfather on his deathbed, quite literally, that you resented him for being a burden to your mom?

[00:52:05] Nathan: I think there’s things that you don’t want to tell someone because of the impact or the burden that it would place on them or how it’d make them feel. And the thing that I realized is most things, if you’ve been around someone for a long time, most things that you’re like, “Oh, I probably wanted to…

[00:52:21] I shouldn’t tell them this,” or that sort of thing, they already know. You told them, like, 500 tiny little ways over time in how you acted, how, like, the little things, right? And so what I realized is I think that I, I think I told him in 500 little ways, and he felt that. And so I told him the opposite. Um-

[00:52:52] I told him that I was so grateful that he was in my life and my mom’s life because I was able To see my mom through him express like the truest nature of who she is.

[00:53:12] Chris: Mm-hmm.

[00:53:13] Nathan: And he brought that out of her And so it was this really special moment to be able to invert that and to basically say

[00:53:30] Not to place a burden on him, but to relieve him of that. Right. Because this is something that I told him 1,000 times-

[00:53:33] Chris: I see …

[00:53:33] Nathan: in subtle ways. But to say, like, “No, actually, I see it the complete opposite

[00:53:38] Chris: now.” Mm. Thanks for sharing that story and for being real with me.

[00:53:42] Nathan: Yeah. Thanks for drawing it out.

[00:53:44] Chris: Oh, we’re not done with the drawing yet.

[00:53:49] Okay. Um, I think in that moment… I’m gonna make a lot of assumptions ’cause I don’t know you well at all. Yeah. So you can say, “You jackass, you don’t know-” Yeah “… anything about nothing.” But-

[00:53:57] Nathan: Just throwing water

[00:53:58] Chris: in

[00:53:59] Nathan: your face. Yeah. Storm

[00:53:59] Chris: out. This is not the podcast I signed up for. I think in that moment, um, you’ve ascended.

[00:54:06] because you kind of let something that’s been eating you up, instead of just releasing on him, you kind of released him of this thing. And I think you did it for him, you did it for you, and maybe you did it for your mom. I don’t know.

[00:54:20] Nathan: Yeah.

[00:54:21] Chris: But we were talking about enemies and what you, what you stand for.

[00:54:27] My, my therapist had asked me this many years ago. He goes, “I’m curious about your wife. Is she anything like you?” I’m like, “We’re the exact opposite.” We’re the exact opposite in every single way I can imagine, but we work. So she’s like, “I have this weird theory about people, is like they’re brought into our lives to teach us something.”

[00:54:44] And, and that sounds, depending on how you interpret that, it could be a negative. It’s, doesn’t sound like a positive to me. But if you think of your mom’s greatest gift is the ex- her expression of love is to take care of people, I think your stepfather came into her life so she can express her gift. Like Superman is Superman because of Lex.

[00:55:04] And so we, we just see it, and I, I think maybe, who knows, this will probably be another session. But there was a child inside of you who was like, “Mom, what about us?”

[00:55:14] Nathan: Mm-hmm.

[00:55:14] Chris: Or like, “I, I will work to support you, but then now you’re supporting this other random dude. You know, what up, what up with that?” It’s crazy.

[00:55:21] But y- you have to believe somewhere that your mom found somebody who completed her in a way that you could not understand, because you don’t have the same lens into the world.

[00:55:31] Nathan: Right.

[00:55:32] Chris: And perhaps your mom doesn’t shine as bright without him. Who knows? But in that moment that you’re able to flip this is the thing I try and help people with, but not from an external point, from an internal point.

[00:55:42] Now, imagine this entire conversation happening inside your heart and your brain, where you feel like, “I’m a caretaker,” and there’s this other side where it’s like, “I need to be taken care of.” And they’re in conflict with each other. Mm. And the resolution that you found was that they’re not in conflict, they’re, they’re complementary- Mm-hmm

[00:56:00] to one another. I don’t know.

[00:56:01] Nathan: Oh, yeah. Right? No, it’s absolutely… Like, the, my, uh, biggest expression or my favorite thing to do is take care of people- Yeah … and to serve them and all of that. And then my- Oh,

[00:56:10] Chris: this is fascinating …

[00:56:11] Nathan: my other favorite thing is to be taken care of.

[00:56:13] Chris: Okay, this is wonderful. Look at this.

[00:56:15] Look at this. I mean, I don’t know what happened. Forget about, uh- … entrepreneurship here. Your whole company and your whole ethos is to take care of other people and help them- Mm … in their business. So what if the world had no problems to take care of? You’d be out of purpose.

[00:56:29] Nathan: Yeah.

[00:56:30] Chris: So in the thing that you saw in your stepfather, it’s like you need that to exist.

[00:56:36] And in your own way, in a very different way, you’re helping a lot of other people, and the greater their problem, the greater of service you can become. So I wrote down a couple of words here. Okay. You’ve mentioned the word burden, like many, many times. Yeah. I wasn’t counting, but like eight or nine times.

[00:56:51] So that, that word has to be somewhere in this-

[00:56:53] Nathan: Mm-hmm …

[00:56:54] Chris: world of yours. You mentioned the word impact slightly, and then I started to, to, um, pull other words out of this, like contribution, carry your weight, dead weight, this feeling of resentment, and this idea of the greatest expression of love is blank, blank, blank.

[00:57:08] We don’t know.

[00:57:09] Nathan: Mm-hmm.

[00:57:09] Chris: Okay? So I wonder if something that’s like the line is something, this is horrible, we’re just kind of workshopping it, but maybe something about never be a burden. Never feel like a burden. Maybe the feeling is more important.

[00:57:22] Nathan: Hmm. Never feel like a burden.

[00:57:24] Chris: Yeah. That could be the, the…

[00:57:26] There, there’s maybe something in there, because I think the word burden or unburdened or something like that. Like, as, as a man- Mm … I would feel horrible if everyone had to take care of me, ’cause I was- Right … not competent, unable to, you know? And clearly the paraplegic guy, he had his own battles to deal with.

[00:57:44] It’s not like he chose to just loaf around and eat potato chips.

[00:57:47] Nathan: Right.

[00:57:47] Chris: You know? It, it was life dealt him a set of cards, and he played the cards as best as he could. But I, I do have similar reactions to you when I see people, like you’re not holding up your end of the bargain. Mm. And maybe that’s also something else.

[00:58:00] We have strong conviction about how we’re supposed to contribute, that we should give more than we take, and in this perspective, somebody was taking more than they were able to give, in the way that we can see on the dimension that we’re looking at.

[00:58:11] Nathan: Yeah, and I think the, the thing about the burden is that it’s, it’s a full circle thing.

[00:58:18] Because if I wanna help people go on the same journey that I did, or that I’m going on, it’s to have all of the tools and the mindset and everything else so they don’t have to be a burden on other people. And so they can fully take care of themselves and them around them and, and all that. And then- To also be able to set that aside and be willing to be a burden on someone, and be willing to accept that help, right?

[00:58:45] ‘Cause that’s the hard thing. I thought if you would’ve asked me, I don’t know, five, five years ago, 10 years ago, somewhere in there, I would’ve thought, like, okay, I… Get me all the tools, all of that. I will get to this point. I’m now, um, you know, fully of service to others. Uh, I would actually keep a little bit of a scorecard.

[00:59:03] Like, if I… The more generous I am- Mm-hmm … the more I know that I have served you more than you’ve served me, and I can know that I’m not a burden. And so I would’ve thought, like, okay, that is the, some self-actualization moment. And then the, the arc in this is like, oh, to come all the way back to a point where it’s like, oh, I have value as an i- individual, even if I can’t, even if I am a burden on people, and to be willing to accept-

[00:59:26] Chris: Mm

[00:59:27] Nathan: that help and everything from that.

[00:59:28] Chris: Mm. Uh, I’m gonna return your notebook to you. Yeah. You can have your, my notebook back. But I was sitting there thinking, the word burden is a judging word. Mm-hmm. It’s a very violent word.

[00:59:39] Nathan: It is, yeah.

[00:59:40] Chris: Right? Because I wonder if when we see ourselves being a burden to someone else because of your feelings towards people in your life, like your stepfather, who was a burden to your mom- Mm-hmm

[00:59:50] drained her resources, and her energy, and her love, and everything that she could give, well, we’re gonna have a pretty negative feeling about that word.

[00:59:58] Nathan: Right.

[00:59:58] Chris: So when someone wants to help you, they want to serve you, but you won’t let them because you see yourself as a burden, and so the last thing you want to do is to become the person you had a lot of resentment towards.

[01:00:09] Nathan: Right.

[01:00:09] Chris: So I think what we wanna do is find some neutral word to describe what this is. And then, then you can be liberated from this idea.

[01:00:18] Nathan: Right.

[01:00:18] Chris: Yeah. And I struggle with this too, because I, I think I need to take care of people, and when somebody’s like, “Can I help you do this?” I … In my mind I’m like, “Please.”

[01:00:27] Yeah. But I’m like, “No, I got this.” You know? It’s not, it’s not out of pride, it’s just, it’s just we’re afraid of receiving help for whatever reasons, ’cause there’s a, an emotional charge against receiving help. So the people who I consider some of my closest, uh, friends are the ones who push past my resistance, and they’re like, “Well, I’m doing it anyways.”

[01:00:47] Nathan: Right. ”

[01:00:48] Chris: I’m picking you up tomorrow at 4:00 AM, and I will take you to the airport, and I will make sure you get on this plane or train.” I’m like, “You, you, you care about me? Oh my God.” You know? Yeah. And they can just push past that. Mm-hmm. And I think, um, I know this conversation has spiraled into a thousand different directions.

[01:01:04] There, I think there’s, like, toxic masculinity, and I don’t know what the opposite version of that is, but I think men need to be able to understand with each other we’re often hard … It’s … We find it difficult to ask for help and to receive help, but to understand, like, I’m gonna give you help regardless, just knowing that underneath that you really do want help.

[01:01:22] Nathan: Right.

[01:01:23] Chris: And not to be a jerk about it. So there’s something there.

[01:01:26] Nathan: Well, I think the, the thing that I wanna end on is- Yeah … you have this idea that you talked about of how the more perfect someone looks online-

[01:01:34] Chris: Yeah …

[01:01:34] Nathan: the less we trust them.

[01:01:35] Chris: Yeah.

[01:01:36] Nathan: And that’s part of why, like, I’m so excited to take this conversation the w- place that we did, right?

[01:01:41] Because it’s just like let’s … You talk about being authentic. I’m pretty sure this is an un- like un-bland conversation. It is. You know? Um, so but how do you bring this level of vulnerability and, like, authenticness and the imperfections through into the brand or the content that you let people see?

[01:02:00] Chris: Okay. I kind of look at it like this.

[01:02:02] Uh, there, there was an article written in Harvard Business Review. I’m, uh, I’m, I’m forgetting the, the two women’s name, but they, they called something like the trust triangle, like, why we trust some people more than other people. And what we’re really trading on is trust everywhere we go. You buy a car or a c- or, or a jacket because you trust that person or that brand.

[01:02:23] This is how we, we do things. We trust this food is gonna be okay. It’s not gonna kill us, right? The trust triangle starts with the top part, which is authenticity, and it’s a very broad, generic word that’s being overused and misused a lot, but it’s really are you who you say you are? That’s it.

[01:02:37] Nathan: Mm-hmm.

[01:02:37] Chris: And a lot of us are not.

[01:02:39] That’s my mission is to close that gap between- Right … this inauthentic self and the real you. And if we can do that, we’re starting off really great. Second part to the trust triangle is this word, they use empathy, but they don’t use it the way that we use it. They’re, they’re … The word empathy to them is are you looking out for me?

[01:02:55] Do I feel like Nathan’s looking out for me? Mm-hmm. Do I feel like Chris has got my best intentions at, in his heart? And the last one is, and it’s a weird one, ’cause it’s like what? It’s logic. Do you talk about things in a way that I can follow?

[01:03:10] Nathan: Mm.

[01:03:10] Chris: So if we look at someone who’s on stage, and we feel like they’re being performative, and they’re presenting themselves to be more perfect, perfect life, perfect wife, perfect everything.

[01:03:19] Yeah. Everything is perfect. Like, ugh. Something about us feels, we, we’re like, “It’s off.” Right. It’s off. All their stories are too manufactured, too polished, and it, it gives us the ick feel. So already we’re, we’re losing trust. And then they’re talking about something, we can feel like, oh, you’re gonna bring and rope me into a book or a course or a master class or a cohort.

[01:03:38] The pitch is coming. I already can feel it. We’re not… Yeah, we can feel the pitch a mile away. It’s like they think we can’t see the train, but we can. It’s like a, it’s a flat line. I can see it coming. It’s coming. I already know. So we’ve lost trust on two things. And, and then they’re, like, able to logically tell us, “Well, I’ll agitate the pain, and the results are great.”

[01:03:55] We see that. You need all three components to come together in harmony for you to have trust. So when we’re being overly polished, it, first of all, requires a lot of mental and spiritual energy to hold something up, right? It’s like we gotta clean the house before everybody gets here. We gotta make sure the lens and the makeup and the beauty filters and all that kind of stuff is perfect.

[01:04:16] It requires too much energy. And I, I don’t know about you, I have finite energy. Mm-hmm. And I wanna spend all of my energy being my truest self. So if I divert that energy away, then what happens to me being in this moment, connecting or listening to you, it’s diminished, and I don’t wanna do that. And it requires some level of bravery to, to speak truth, to be able to say what’s on your mind in a way that’s not violent to other people.

[01:04:42] It, it’s a skill. Just like how Jason Freed was talking about making money is a skill.

[01:04:47] Nathan: Right.

[01:04:47] Chris: I think learning how to use your authentic true voice is a skill.

[01:04:51] Nathan: Yeah.

[01:04:51] Chris: Requires practice.

[01:04:52] Nathan: If you were to give people maybe one question to sit with or a place to start if they’re gonna sit down with their journal, anything come to mind?

[01:05:01] Chris: Wow. Um, I have talked a l- a lot about shadow self and doing this, and I realize how hard this is. Mm-hmm. So I don’t wanna send people down that path.

[01:05:09] Nathan: Mm.

[01:05:09] Chris: Because they’ll try, and like, “This is too weird. It’s too hard.” Yeah. “I, I need my therapist next to me. I need, I need some support.” So I’ll, I’ll do it differently.

[01:05:17] I wanna give them a quick win. So the first thing I can do is to have people figure out their voice phrase.

[01:05:24] Nathan: Okay.

[01:05:25] Chris: So I, it, it turns out, like, it’s a pretty good compass as to who you are, and it’s your North Star. So we… The exercise is write down how you sound to the world, as many different words as you, as you can write, and just write without editing, without thinking, without curating.

[01:05:42] And if you get stuck, say, “Well, how would my friend describe me as my voice? How would my employee or my boss or my partner, my parent, my sibling describe my voice?” And sometimes it’s really weird. We, we don’t think we have the answers, but as soon as I change the phrase or the prompt, they can start to write.

[01:06:01] Yeah. Look at the collection of words and select the three that ring true, that build on each other versus that are redundant. So bold, brave, don’t use those two words. You get to use one of them. Okay. And find your three words, okay? Now you’ll find your three words. Then sit down and try to think, “What is a short two to five-word phrase that sums up these disparate characteristics about me?”

[01:06:25] The example is this. A buddy of mine, he’s a photographer. He teaches embodiment through posing. He, he’s, he’s a real interesting person because the photo is just, um, an artifact of how the person feels.

[01:06:38] Nathan: Right.

[01:06:39] Chris: It’s pretty powerful stuff that he does. So when he came up with his three words, he said, “I’m flamboyant.”

[01:06:44] You definitely are. “I’m very playful.” You most certainly are. And he’s, “I’m vulnerable.” So I sat with those three words, and I was just writing, thinking, “Okay, so your voice phrase is big energy, open heart.” And I said that to him, and he goes, “My God, that is everything I’ve ever done.” I’m like, “I know.”

[01:07:01] Nathan: Yeah.

[01:07:01] Chris: But we don’t put words to it, so we, we don’t know.

[01:07:04] It’s very abstract. It’s like a fog. And all of a sudden, this makes it really concrete. For me, um, just as one more example, I am critical I’m direct, but I’m caring

[01:07:16] Nathan: Mm-hmm

[01:07:17] Chris: And those are important words to me Critical

[01:07:18] Nathan: and caring have that, yeah

[01:07:20] Chris: Yeah, there’s like that kind of polar dichotomy kind of thing.

[01:07:22] So my voice phrase would be hard truths gently told

[01:07:28] Nathan: Hmm

[01:07:28] Chris: And I find, like, how do we use this, right? Hard truth. So if I write something, if I’m on a podcast with you, and people walk away, this is just a lot of generic nonsense, or it’s just he’s playing it too safe, then I’ve failed my own identity. So I need to say what I feel in my heart.

[01:07:42] And al- almost always it is contrarian. It challenges the norm, and it sometime is triggering. I’m not doing that on purpose. It’s just who I am. But if I do it in a way that you walk away feeling like, “What a A-hole,” then I’ve not done the gently told part

[01:07:57] Nathan: Right

[01:07:57] Chris: So I have to use non-violent language. I have to emote through the tonality of my voice that people feel like, “Yeah, that bastard does care.”

[01:08:08] Nathan: Hard truths gently told

[01:08:09] Chris: Hard truths gently told. They don’t always have to be opposing

[01:08:12] Nathan: Right

[01:08:12] Chris: Right? ‘Cause other people have different phrases, and I’m like, “That’s great. That sounds just like you as far as I can tell.”

[01:08:18] Nathan: I love that

[01:08:19] Chris: So do that. See what happens

[01:08:21] Nathan: Chris, thank you so much for coming on. If people wanna follow more of your content, where’s the best place to go?

[01:08:26] Chris: You can find me on all social channels. I’m @thechrisdo, and that’s spelled D-O.

[01:08:30] Nathan: Sounds good. Thank you so much.

[01:08:32] Chris: Thanks for having me, man. Thanks for crying.

[01:08:34] Nathan: Anytime

[01:08:34] Chris: Thanks for being real. I like it

[01:08:36] Nathan: If you enjoyed this episode, check out episode 82 with Dan Martell. Dan built a $100 million company using a specific framework that turns your personal brand into real business results.

[01:08:47] Like the video if you enjoyed it, hit subscribe on YouTube or wherever you’re listening, and I’ll see you next week.

[00:00:00] Jasmine: This model, Nathan, will knock the air out of your freaking lungs.

[00:00:04] Nathan: Jasmine Star made $255,000 in five days on her first course.

[00:00:09] Jasmine: That 197 course ended up generating over seven figures.

[00:00:13] Nathan: And then she built a membership to over 10,000 people.

[00:00:15] Jasmine: Oh my gosh. Like, we just had like 34% Right … growth in a matter of five days

[00:00:19] Nathan: But like many, she watched as the model gradually stopped working.

[00:00:22] Jasmine: 8% of people finish a course.

[00:00:23] Average amount of time of people in a membership is less than three months.

[00:00:26] Nathan: When Jasmine started building around client results, everything changed.

[00:00:29] Jasmine: People want results. They don’t want more information. The way we actually get the quick results, the way we see people making money in 30 days, it is literally…

[00:00:38] Nathan: I love this.

[00:00:39] Jasmine: People want more time.

[00:00:40] They want more money, influence/power.

[00:00:42] Nathan: Everyone defaults to the exact same models.

[00:00:44] Jasmine: Yes. That is what we teach. Result in a timeframe, given support, period, the end.

[00:00:49] Nathan: I love that.

[00:00:50] Jasmine: You send us five questions in a day, and you get five responses back in a day. No, we move fast.

[00:00:54] Nathan: Coaching and accountability. Mm People are not talking about this enough.

[00:00:56] Jasmine: Are we spilling the tea right now?

[00:00:58] I, I think we are I mean, are we like making waves, Nathan? Let’s go.

[00:01:00] Nathan: If you want an offer that produces results, watch this episode to see how she built it And

[00:01:04] Jasmine: I’m gonna tell you the four steps of the 10K Freedom Formula, step one.

[00:01:07] Nathan: I think this episode is the single highest value per minute- … that’s ever been on my show You know I

[00:01:12] Jasmine: like to win, Nathan.

[00:01:13] Nathan: I know you do.

[00:01:14] Jasmine: Give me another thing to win at.

[00:01:18] Nathan: Jasmine, welcome to the show.

[00:01:19] Jasmine: Thank you.

[00:01:20] Nathan: Okay, so if I were to put you in front of a room-

[00:01:22] Jasmine: Mm-hmm …

[00:01:22] Nathan: of 25 creators who are, I don’t know, making half a million dollars a year or more- Mm … and I was like, “Okay, you need to teach a workshop about your favorite thing”-

[00:01:30] Jasmine: Mm-hmm …

[00:01:31] Nathan: go. What would the topic be?

[00:01:33] Jasmine: Uh, making money from a digital offer.

[00:01:35] Like, I, I love it. It’s like I eat, breathe this stuff. I just think that there’s nothing right now in the market, and hasn’t preceded for many years, that has the profitability, the functionality, and the scalability of a digital offer. Especially if you’re having, like, a, a small team or no team at all. I’ve seen solopreneurs crush it, seven-figure businesses, solopreneur.

[00:01:52] Mm.

[00:01:52] Nathan: Okay. So when you say a digital offer, like what- Mm-hmm … are a few of the examples?

[00:01:55] Jasmine: Like- Okay. Well, we can talk- Yeah … about traditional, like we ta- old school, and then what I think is the future.

[00:01:59] Nathan: Okay.

[00:01:59] Jasmine: Are we really starting here, Nathan? We’re starting here. Are we hitting the ground running?

[00:02:02] Nathan: Oh, yeah. We’re

[00:02:03] Jasmine: diving right in.

[00:02:03] Oh, man. Okay. So this is the tea, and this is one girl’s perspective. But this is a girl who’s been in the game for well over a decade. Yep. And so we’ve seen a transition. And so when I entered the game roughly around 2016, um, I had entered into the market, I was a professional photographer traveling the world, trading- Mm-hmm

[00:02:19] hours for dollars.

[00:02:20] Nathan: Yep,

[00:02:21] Jasmine: time for money. Now… Yes. But it was, it was, it was great. I had created a seven-figure revenue stream. And I had, I was selling digital products at the time for like 399, 499 online- Mm-hmm … for photographers to build the business of their business. And so I kind of had a, a knack for photography, a knack for marketing, but blending those two kind of created like a force.

[00:02:38] So I was able to get all inbound. We were charging multiple six figures for complete collections for what we were shooting. So it was, there was that revenue stream, there was an online digital revenue stream, and then I had this idea. I didn’t even know where it came from, and here I thought, I was like, “Oh, I’m gonna create this thing that’s like an online class, and people are going to buy it.”

[00:02:59] Little did I realize that there were things like course platforms, things called webinars. Uh, there were ads. I had no clue. Yeah. And so, um, so I start off with a course for $197, and I had never created a course. I had never had a landing page. I, I didn’t, I didn’t know anything. Like, like Nathan, I had, I had a newsletter list, but it was on my blog, and it was just like an HTML code that I

[00:03:22] Nathan: had just put

[00:03:22] Jasmine: there.

[00:03:22] It’s just like the RSS feed. Just, yeah. Just sign up. It says that if you publish a, a post. Yes, of course. Yeah. Of course. But we, I had grown it all organically, and I was blogging. So I was writing about my photography, and lucky for me, SEO was kind of like my jam. Yeah. So that helped a lot. And so then my blog post would point to an online store.

[00:03:38] But here again, I was charging anywhere from like 499 to 1999. These were low-ticket items- Yeah … that people were buying, but I would wake up, and then I would see money. And I was like, “Wow, this is crazy.” Then I launched a course for $197, and in five days I made $255,000. Nathan.

[00:03:55] Nathan: A different life.

[00:03:56] Jasmine: A different… I mean, it was like, you know, Charlie Bucket, the Willy Wonka Char- Chocolate Factory.

[00:04:00] I was just like, “Oh my God, Grandpa Joe.” Like, our lives just changed. It was crazy. Went on to launch that course again two more times that year. So that 197 course ended up generating over seven figures- Mm … in one year. So I had my photography online store, I was still doing services for clients and editors and art directors, and I had this revenue stream.

[00:04:21] And to me, by that point in time, I was like a photographer like 13 years. Kind of rose to where I wanted to go, and then I realized I wanna go all in on this vehicle. Mm-hmm. And so started creating a multitude of courses, each turning into their own seven-figure revenue streams. And what I heard on the back of all the courses was people had wished that there was some sort of continuation.

[00:04:40] And a lot of what I was teaching was marketing and branding. And marketing at the time, specifically on social media, it was changing so fast that even though I was creating an evergreen course, people wanted to know the nuances. And at the time it was just like, well, what is the thing called stories? And then what is Instagram Live?

[00:04:53] Mm. And I just felt like kind of to create this new course every year, it just felt like very heavy. And so people were asking, “We want real up-to-date things.” And they were asking for a membership, and I was like, “Never. Never gonna do membership. Nope, nope, nope.” And then all of a sudden I thought to myself, “Okay, if we were to create a membership-” And 500 people joined.

[00:05:15] That MRR, okay, that might be, that might be something we could sink our teeth into. So when I say we, my husband and I, business partners, high school sweethearts. Th- I married up. This guy is great. Nobody understands why he’s married to me. Like, everybody always questions, like, “Bro, what happened?” He’s like, “I, like…”

[00:05:29] He somehow, he’s in. He’s in. He’s got beer goggles. And so, um, we, we stay up, and we know we don’t know any code. We don’t know anything we’re doing. Mm. And I don’t know… You, you know, dude. There was, uh, a company called Infusionsoft.

[00:05:42] Nathan: Yep,

[00:05:43] Jasmine: yeah. Dun-dun-dun. We built a membership off Infusionsoft.

[00:05:45] Nathan: Yeah.

[00:05:46] Jasmine: Just on the backend applying tags because n- the software at the time, this is where I’m gonna geek out, the software at the time was granting memberships all in access.

[00:05:54] So if you joined, you got access to everything that was with that, whatever was in that archive. And I had the school of belief, well, when you join this membership, you get what you get that month, and then months thereafter. You don’t get access to an immediate archive. Okay, right. So the only way that we were able to, like, work around this ghetto was Infusionsoft.

[00:06:09] So every month, they would get applied a tag that reflected in their accessibility. It was Frankensteined with WordPress and Infusionsoft. I’m telling you, brother, it was a nightmare. But, but it was, we took what we had, and then we made it work.

[00:06:22] Nathan: So there’s an important thing in there, ’cause everyone has, has done the standard way, which is you get…

[00:06:28] You, you know, you pay, I don’t know, $50 a month, right?

[00:06:31] Jasmine: Yeah.

[00:06:31] Nathan: And you get access to the entire back catalog and everything coming forward.

[00:06:35] Jasmine: Mm-hmm.

[00:06:36] Nathan: And then memberships have this massive problem. Yeah. That the churn is really, really high.

[00:06:41] Jasmine: Yes.

[00:06:41] Nathan: Everyone says, like, sees software and says, “Oh, I want recurring revenue-

[00:06:45] Jasmine: Yes

[00:06:46] Nathan: and all that, so let me do it with content,” and then they find that the churn is not 5% per month, it’s 15 or- Oh, yeah … percent, you know, and-

[00:06:53] Jasmine: Oh, yeah …

[00:06:53] Nathan: and all that. So but what you’re saying is like, no, no, no. You paid, in my made-up example, $50. Uh-huh. You get this $50 worth of content. You don’t get the back catalog.

[00:07:02] Jasmine: Correct. Okay. And at the time, this was 2017. Mm-hmm. Now, a lot has changed.

[00:07:06] Nathan: Yep.

[00:07:07] Jasmine: So when we go back to what was available, we took what was available and then Frankensteined a way that we could reverse engineer- Right … protecting that content, and I say protecting, and that probably what is probably myopic when I speak about it now, but at the time, I was just like, we were charging $29 a month in 2017.

[00:07:23] And I thought that that $29 is worth more than the value of a back catalog. Right. And so then what we did was we allowed people to go back and purchase individual, we called them issues, individual issues. Mm. So immediately, first month of the membership, we started realizing that when we first launched, we had a back catalog of three, and then that month.

[00:07:40] And people were coming in and not just buying the $29 for that monthly membership. They went back and bought the back catalog, and then a month later were charged another $29. So we saw LTV in months one, two, and three exceed what traditionally would be months one, two, and three because of the back catalog.

[00:07:54] Nathan: Okay.

[00:07:55] Jasmine: Mm-hmm.

[00:07:56] Nathan: I’ve, I’ve been in this business a long time.

[00:07:58] Jasmine: Uh-huh.

[00:07:58] Nathan: I have not heard that particular angle on it, but I like it because it changes the perceived value as well. Because so many people get access to the back catalog, binge it, and then end up paying for three more months maybe?

[00:08:09] Jasmine: Well, right now I think the average is less than three.

[00:08:11] Nathan: That’s probably, yeah.

[00:08:11] Jasmine: And so, t- so, and me- Okay. So we, we did that. Right. And I, I thought it was great, except for the fact that what we were creating on the inside of this membership was marketing content, teaching people how- Mm-hmm … to create their marketing for small businesses. So creators, small businesses, people who didn’t necessarily have an entire marketing team.

[00:08:28] So what we were doing is we were teaching the, the strategies, we were giving how-tos, we were giving examples, we were giving templates and resources. Right. All this came in a particular issue. And what I realized was people were learning how, and getting their marketing, but we weren’t integrated. And so they would have to go from our membership, download what they needed- Mm-hmm

[00:08:44] modify on their own, and they were creating their own systems on the backend for their, um, marketing. Okay. And that was a lot of friction. And so then what we decided to do in 2021 when the world was basically a dumpster fire, I know not a single line of code, and I’m like, “Okay, we have to build our own tech stack.”

[00:08:59] Nathan: Right.

[00:08:59] Jasmine: I need a CTO, I need a team. I was very much like Veruca Salt. “I want a Umpa Lumpa.” “I want a SaaS company and I want it now.” No idea. Like, no idea what I was doing. Holy… Like, somebody just, if I can go back to that girl, I would just pat her head, I would hug her- … and be like, “Girl, you, you step away from the tequila.

[00:09:16] We’re not doing this right now.” But we did. And so, uh, started our own tech company, and it was great. We integrate with every social platform- Yeah … that exists today. It is called Social Curator. And we started leveraging AI in 2021. Mm-hmm. So we started, like, very early, and I was like, “Oh my God.” So we were having what we called caption templates.

[00:09:35] And they, think about this as Mad Libs. And so y- let’s say you, the creator, would be able to go in and fill in the blanks, and they were, like, reverse engineered for engagement on social media. And I, and I would just dreamt, I was like, “If, if just one day we were able to have profiles for each of our customers and it would auto-populate in our templates.

[00:09:53] Man, golly gee willikers if that ever existed.” And so then 2021 comes around, and the tech team is really in learning about AI. We start leveraging it, and I’m like, “Oh my God, solution. Here we go. To the moon all the way.” And then by 2022, I’m like, “They’re gonna eat our lunch.” Like, it was clear we could not outpace Sam, Sam Altman.

[00:10:12] Yeah. You know, it was just not gonna happen. Me against, uh, OpenAI and- Him and his

[00:10:16] Nathan: billions.

[00:10:16] Jasmine: Yes. Yeah, absolutely. So, uh, you see the writing on the wall. Right. And you’re like, “What is happening to the industry, and where are we going?” So we’ll pause. In 2020, we saw a massive shift happen in the creator space.

[00:10:27] Right. And so what happened was people were at home more. They had more money. On average, the US household income in 2020 had $15,000 more. Yeah. So we saw social media increase by 40% during 2020. People on average had $15,000 per household, and we saw online shopping increase at almost a pace of 48%.

[00:10:49] Nathan: Right, and yous- I mean, you saw people traveling a lot less, a lot of discretionary spending-

[00:10:53] Jasmine: Of course

[00:10:54] Nathan: didn’t get spent- Of course … ’cause there wasn’t a good way to do it, and then you have stimulus checks- Stimulus checks … coming in.

[00:10:57] Jasmine: Exactly.

[00:10:58] Nathan: Yeah, all of those things.

[00:10:59] Jasmine: So it was perfect for people who had an online business. Not a business online.

[00:11:03] Nathan: Right.

[00:11:04] Jasmine: An online business. And so what you saw was massive growth spikes.

[00:11:08] So we just saw, like, compounding growth. So at the time, Social Curator, we had 6,500 members. Yeah. We had just started, and we opened cart for five days. And we got close to 10,000 people in five. And so we were like, “Oh my gosh.” Like, we just had like 34%- Right … growth in a matter of five days. And so we just saw this compounding growth over that year, and then that inspired a lot of people to go through.

[00:11:31] They bought courses. Mm-hmm. And then they think, “I’m a course creator,” which, hey, maybe you are. But did you count the cost of actual, um, deployment, fulfillment, customer service? Right. So 2021, 2022, you see a boomerang. People who launched creative endeavors realize that that’s a totally different game and a totally different skill set, and many people are just like, “I’m out.”

[00:11:51] Right. So it left a lot of people burned. So 2023, 2024, there’s a trust recession. People are trying to sell digital things online, and people are, like, a little skeptical. So it puts us in this phase of ’25, ’26, what is the future? So when you’re like, “When you talk about a digital resource, when you talk about online business, what are you talking about?”

[00:12:07] And I was like, “Well, the old way, courses, memberships, one-on-one, I think that there is a place for them. But I think that in order to be competitive and to go against the grain, when everybody’s zigging, you zag.” I really do believe what I’ve now coined as the hybrid offer, is that there is a piece that teaches somebody a result.

[00:12:27] Mm-hmm. Period, the end. Nobody wants more information, and no one’s really gonna buy information. That’s just the truth. So what you’re selling is how you get a particular result in a specific time ri- timeframe.

[00:12:37] Nathan: Okay.

[00:12:37] Jasmine: And so what we see on average is about 8% of people finish a course, and about, uh, average amount of time with people in a membership is less than three months.

[00:12:44] So what would somebody pay for a result in a certain amount of time? And so that is what we, that is what we teach, result in a timeframe, given support, period, the end. So the more people who get a result, the more people who refer you. And then when you make another offer that guarantees or promises a result in a given timeframe, now we have trust built.

[00:13:02] So now we’re rebuilding trust when there was a trust recession. Hmm. So we’re now combining a skill set, a result, and a transformation for our customer

[00:13:11] Nathan: Okay.

[00:13:11] Jasmine: Yeah.

[00:13:12] Nathan: I love this, and I love your passion behind it. Where, like, what’s an example of an offer in the old format, and then what it would look like rebuilt in this way?

[00:13:22] Jasmine: Okay, so a course. I help you lose weight.

[00:13:24] Nathan: Mm-hmm.

[00:13:25] Jasmine: Let’s get a little bit more granular. I help women lose weight. And then let’s get even more granular. I help women in their 40s lose weight. Right. So we would see courses in that, in that way. Yeah. But what would happen was the nature is, like, I teach everything about a woman in their 40s.

[00:13:40] So hormones and eating and exercise and all these other things. So people are like, this is a complete, like, drinking from a, a, a fire hydrant.

[00:13:48] Nathan: Yep.

[00:13:48] Jasmine: And so people just don’t do it.

[00:13:49] Nathan: And, and so there’s no result, no

[00:13:51] Jasmine: behavior change. There’s no result, there’s no behavior change, and then there’s no further buying.

[00:13:54] Mm-hmm. They’re not gonna buy again from a person where they didn’t fulfill on the first thing. Right. So a hybrid offer now would be hyper-specific around a specific result. So I help women in perimenopause- Mm … lose 10 pounds and sleep through the night in 90 days. So now- Which is very specific … very specific.

[00:14:12] So people want results. They don’t want more information. Mm-hmm. And information is commoditized. So the more that you can get a transformation, a result, and then you support that result, because we know what happens. Is what I believe in a hybrid offer is the support is what guarantees the result. Because a woman in her 40s in meni- perimenopause can lose 10 pounds, but then what happens?

[00:14:28] There’s vacation, life changes. Right. You go… Like, a ton of things can happen. So as long as you help her get that result and keep it, she becomes a fan, she turns into a fanatic, and she’s the person who’s help endorsing and growing your business thereafter.

[00:14:40] Nathan: Okay. Yeah, that, that makes perfect sense. ‘Cause something that I think about a lot is what actually creates results is usually simple but not easy.

[00:14:48] Yes. And so if you think about weight loss or building a business or any fitness habit or anything else, when you talk to someone… I remember talking to someone who, I found out through, through the conversation, he was like, “Yeah, I used to weigh, like, 350 pounds.” And I was, like, shocked. ‘Cause I was like, “You don’t look like you ever…”

[00:15:02] You know? Yeah. I was like, “What did you do?” And he’s like, “Well, I, you know, tracked what I ate- Mm-hmm … and I exercised consistently.” I’m like, “And?” And he’s like-

[00:15:09] Jasmine: That’s it …

[00:15:10] Nathan: that’s the whole… You know. And he said this line of, like, “It’s simple, but it’s not easy.” Easy. And so what I hear you doing is- There’s an endless amount of information that you could learn.

[00:15:20] Jasmine: Mm-hmm.

[00:15:20] Nathan: And you’re saying, “I’m just gonna distill it down to this one very specific offer- Yep … then this, um, very specific outcome for a specific- Mm-hmm … type of person.” And it’s, it’s taking the niche down advice- Mm-hmm … and making it so much more specific, ’cause- Yeah … most people do it and, like, “Here’s who we’re targeting.”

[00:15:35] We’re actually doing it in terms of, “Here’s how we’re serving them.” And then just saying, “I’m gonna come alongside you- Yep … and make sure-

[00:15:43] Jasmine: Yep …

[00:15:44] Nathan: that we achieve the outcome.”

[00:15:45] Jasmine: Absolutely. And what, what ends up happening is that y- there’s an extension of brand. Mm. So a brand isn’t your name, it’s not a logo, it’s not your colors, it’s not your website.

[00:15:53] A brand is what you make somebody feel. And so what happens is when you have an evergreen piece of content that teaches somebody how to get a result, inevitably somebody will come across a pitfall, perceived or real. Right. And so when you show up and answer their question or support them or just say, “Hey, I see you,” what you made a person feel was seen, and a seen person will go to war for you.

[00:16:17] Nathan: Mm.

[00:16:17] Jasmine: And that dynamic really changes, and I do believe that with this, um… And I, and fully embrace, I love AI. I truly do. But when we see such this massive embracing of it, it’s gonna be super important to anchor as a point of differentiation a human element. Right. ‘Cause that’s gonna become more and more- rich, more valuable.

[00:16:35] Nathan: Yeah, I believe that very deeply. Where, okay, so we think about the structure of the offer.

[00:16:40] Jasmine: Mm-hmm.

[00:16:40] Nathan: How would you price the old offer, and how would you price the, the new offer? Like, if you were coaching a client going through this- Mm-hmm … or you know, another creator.

[00:16:47] Jasmine: We have a framework. So, uh, uh, with our methodology, we go towards the value, what we think that they would pay for it.

[00:16:53] And the reason why we’re doing this, okay, so Elon Musk-

[00:16:55] Nathan: Mm-hmm …

[00:16:56] Jasmine: sells a Cybertruck, but just sells the idea of it, and thousands of people are paying him $1,000 just to get on the list. Right. And so we see, uh, Jeff Bezos. He decides to have his friends and family buy a book on the internet. So what they’re doing is they’re selling, they’re pre-selling the idea.

[00:17:12] So my philosophy is what I’ve seen a lot of creators do, is come up with, “Uh, this is the thing. This is the idea. This is what people want.” And then they put it out there, and it’s, you know, like 1 or 2% of their audience will buy it. Right. And they’re like, “What happened? It must be me.” No, no, no. We’re just actually not really understanding who is it for, what do they value, and what are they inclined to pay.

[00:17:31] Mm-hmm. And so part of the methodology is not to come in with a pre-done idea. It’s to come in- Right … who do you wanna serve and what result do you think you can get? And then we have people interview their, what we think are their dream clients, have their dream clients actually say, without a pitch or anything, what they would actually pay for a transformation, and we’re leveraging two or three different transformations at one time.

[00:17:48] Yeah. So we’re, we’re really i- we’re really trying to build a business, not this is what I think it’s worth. Because oftentimes what I see, specifically for women, is that they over-deliver and then they under-price.

[00:17:58] Nathan: Yes.

[00:17:59] Jasmine: And so what we wanna do is really go in and just, like, test the market, see what the market will pay.

[00:18:02] And then I, I’m telling you like 8 out of 10 times people are like, “I can never charge that. I can never charge that.” And then we put it out in a seed launch, and then people pay. And that is like a frame breaker, that somebody would pay $500, $1,000 for this when they thought that they would be selling something for $87.

[00:18:18] Right, right. That’s the big thing. But we understand the market, and we understand what willing… what people are paying, not for a course, not for more information, but literally a result.

[00:18:25] Nathan: Yeah, so when you make that sh- that shift from information to outcomes- Yep … the willingness to pay is entirely different.

[00:18:31] Absolutely. ‘Cause I always think in terms of, like in business, of conversion rates, right? And where’s the friction in the steps, and it’s like, you know, in a funnel it’s if we get this many people in, then we work our way down. Yes. And I think a buyer thinks in those ways, where you’re almost discounting, like- Okay, if I would pay $10,000 if I could snap a finger-

[00:18:50] Jasmine: Yes

[00:18:51] Nathan: and have this outcome.

[00:18:52] Jasmine: Yes.

[00:18:53] Nathan: Well, now you have to, uh, think about, like, the time value of money, so you have to… Oh, it’s 90 days later, so it’s… Okay, it’s worth less to me. I can’t have it instantly.

[00:19:01] Jasmine: Yeah,

[00:19:01] Nathan: yeah. And then it’s like, well, what’s the likelihood that that information I’m buying is actually the, the information that’s gonna get me there?

[00:19:08] Jasmine: Yep.

[00:19:08] Nathan: Okay, and so we’re discounting further and further.

[00:19:10] Jasmine: Yes.

[00:19:11] Nathan: And so if I would pay $10,000 for the outcome, by the time I’m all the way back at, like, is your information gonna be the right information- Yes … am I gonna stick to it and all this, and then, like, we’re kind of back at $97. Yeah. You know?

[00:19:22] Jasmine: Yeah.

[00:19:23] Nathan: But if I was very, very confident that you would- Mm-hmm

[00:19:25] create that outcome for me-

[00:19:27] Jasmine: Mm-hmm …

[00:19:27] Nathan: you know, then I’m like, “Okay, five grand.” Mm-hmm. Two grand, you know, like, whatever it is. Yeah. I still have to put in the work. Yeah. But it’s a totally different way of pricing it.

[00:19:34] Jasmine: Absolutely. And one of the things that we realized, and so this is on the back of having courses that ranged from, well, we started off at 147, and then we worked our way upmarket.

[00:19:42] So a DIY course for $3,000. And what we heard again from the courses, even if, even if, so we had two tiers. You can buy the DIY course- Mm-hmm … or for a, somewhere between four or six weeks, I would go live and answer questions- Right … for the first four or six weeks of the program. And so even with that, people were saying, “I just wish I had somebody over my shoulder.”

[00:20:02] And- They

[00:20:02] Nathan: want another level beyond that …

[00:20:04] Jasmine: 100%. And then what I realized was, like, that’s not really gonna work. I- This was the same story that I told myself when it comes to building a membership, was, “That’s not me. That’s not going to work.” And then I heard it so many times, it was like a big slap to the face.

[00:20:16] And so then instead of saying, “That’s not gonna work,” I started asking, “Well, how could that work?”

[00:20:21] Nathan: Mm-hmm.

[00:20:21] Jasmine: What would have to be true?

[00:20:23] Nathan: That, that is my favorite question in the entire world. Isn’t it? Is what would have to be true? Yeah. I ask that question all the time. My team both loves it and rolls their eyes.

[00:20:30] Jasmine: Everybody, but, uh, so I, I do, too, when it’s my own… Like, when I ask myself this question. Yeah. It’s like I, I have that same reaction. And then when we kind of just distilled what has to be true- Mm-hmm … when we laid it out, I looked at it and I, I asked myself,

[00:20:42] “Is that what you want to solve?” Is that. Because it’s not for everybody. Right. Like, systematizing a singular approach, training people on that approach, courting and cultivating and recruiting really talented business coaches to come in and use their experience, yes, but what we’re teaching is this.

[00:21:00] Nathan: Right.

[00:21:00] Jasmine: And this is the system. So a, a lot of times people are like, “Well, business is a mid of, a bit of art and science.” It is, but there’s a lot of science here.

[00:21:08] Nathan: Right.

[00:21:08] Jasmine: There’s a lot of science that can get us, like a, an outcome.

[00:21:11] Nathan: When the more specific you get on the outcome- Yes … the more it moves from art to science.

[00:21:15] Jasmine: Absolutely.

[00:21:15] Nathan: Like if we said, “Hey, we need to build a successful business that does half a million dollars a year in revenue,” there’s a thousand ways to do it.

[00:21:21] Jasmine: Yes.

[00:21:22] Nathan: But then if you compress the timeline-

[00:21:23] Jasmine: Yes …

[00:21:24] Nathan: and then you com- you know, the more constraints you put on it, the more it, it moves into science- Absolutely

[00:21:28] in a way that you’re like, “Great, then do steps A, B, and C in order.”

[00:21:31] Jasmine: Absolutely. And a lot of times the people we’re working with, they’re, um, “I don’t want to do webinars.” Mm-hmm. O- okay, great. “I don’t have an endless budget for ads or any money.” So we started- Right … understanding who the demographic was and then reverse engineering, well, what needs to be true for them for this system to work?

[00:21:46] And then we’re very forthcoming. Like, these are the steps you have to take. That might not be aligned for you. There’s, there’s literally 1,200 ways to get from California to New York. This is our one way. Right. We feel really good with this one way, and we see people get results. If that’s not aligned with you, no problem, but this is the one way.

[00:21:59] Mm-hmm. So we needed coaches that would really step into that and, and believe it. Right. And so that was one of the things that we stepped on. So now we have business coaches using our framework to help business owners create a digital offer in 90 days. Mm-hmm. So it’s, I call it a friendly pressure cooker.

[00:22:16] It’s like you want a digital offer that’s going to make money. We see people making money in the first 30 days. It’s just how bad do you want it?

[00:22:23] Nathan: I love that. Okay, so to get really specific then.

[00:22:25] Jasmine: Yeah.

[00:22:27] Nathan: Take us through the details of your offer.

[00:22:29] Jasmine: Mm-hmm.

[00:22:29] Nathan: Right? Because it’s always- Y- you take all the things that you learned- Mm-hmm

[00:22:32] and then you apply it in your own business. Yep. And so who do you, like, who’s the ideal client?

[00:22:38] Jasmine: Mm-hmm.

[00:22:38] Nathan: How do you price it? What’s the exact, uh, positioning-

[00:22:41] Jasmine: Yeah …

[00:22:42] Nathan: and the, and the promise?

[00:22:43] Jasmine: Yeah. So it- we were taking all of the information that we were getting, and we heard it from the SaaS side is like, “Jasmine, do you also provide social media managers?”

[00:22:52] So people wanted the solution. Right. They also wanted the implementation, and I didn’t want to build an agency. Yeah. That’s not at all what I had wanted. And so then what we heard on the back, of course, is, “Well, if I just had somebody looking over my shoulder.” Mm-hmm. “If I just knew that it was, that I was doing it right.”

[00:23:04] And so we found that our greatest clients are coming in two forms. The creator who has an audience but really doesn’t have the business acumen, and doesn’t really know where to begin, and gets, like, easily overwhelmed, like all the things. Where do I start? Yep. And then a service provider. So we see a lot of success from, like, one person in particular.

[00:23:20] She was a doula. Mm-hmm. And she’s based in Arizona, and she has four clinics, and she’s like, “I can’t keep on multiplying in this way.” And there was a lot of doulas who wanted her training. There was a lot of moms who wanted to sit under her tutelage. She was really good at what she did. So she created a digital offer, and then created rapidly growing six-figure revenue stream off a digital side of her rather dominant in-person business.

[00:23:41] Mm-hmm. So we see wedding planners. We see photographers. We see service providers do something really different and provide a service for those in their industry, and that’s become a big game changer. So creators with large audiences without knowing how to monetize, and service providers. Right. And then also people who have the dream.

[00:23:54] Mm-hmm. We see people coming in who’s like, um, like so for instance, there was a, a woman who worked at Kroger. Management. Worked all the way up. She has two kids, and she’s just like, “I really believe…” And I’m not gonna talk about specifically what her offer was. It’s not out into the world yet. But she was so saying, “I, I, I can’t stop thinking about it.”

[00:24:07] And to me, I look at that and I’m like, “You have the grit.” Yeah. You have the grit. So we can help you build the business and the offer, and you’re gonna have to work on building the audience. But, like, we can do that. But largely, it’s the creator and then the service provider that wants to get into digital.

[00:24:18] Nathan: Okay. And so then what’s the, the structure that you’re taking them through in, in I guess the support that you’re providing that? Yeah. And, and is it a 90-day timeline?

[00:24:28] Jasmine: It is a 90-day timeline.

[00:24:28] Nathan: Okay.

[00:24:29] Jasmine: It’s a 90-day timeline. And so that’s what it is. It’s a result in a specific timeframe. Mm-hmm. That is the hybrid offer.

[00:24:34] Our result is a system and your streamlined business to consistent 10K months. And that’s the floor. That’s not the ceiling. Yeah. But what… And, and it’s crazy ’cause I had hundreds of conversations with people, and I kept on asking, like, “What’s the magic number?” And I heard it a- again and again. I heard two things.

[00:24:49] Mm-hmm. Financial freedom, financial freedom. And so I heard so many times, and we’re like, “Wait a minute. What are people’s definition of financial freedom?” Right. And I was like, “I wave a magic wand and my magic just happens right now. What, like, what, what does it look like?” And people are like, “I could just make $10,000 a month.”

[00:25:02] Mm-hmm. And my mind was blown ’cause I kept on hearing it again, and again, and again. Right. So what we did in titling the offer was just reverse engineer what they told us. Consistent 10K. Mm-hmm. Like, that’s what they wanted. But then a crazier thing happened, is when we made that the title, when I was sitting…

[00:25:17] So I did sales calls at the beginning, ’cause I’m just gonna get in the mud. I’m gonna figure out- Right … where the biggest obstacles are. I’m gonna f- like really go in and hone in on the script of what we were gonna be telling people. And they s- what I heard again and again, “Well, that’s too good to be true.”

[00:25:30] So- You, okay … we heard they, everybody w-, like hundreds, hundreds of- Yeah … conversations I had. This was what they wanted, and then we put it out, and, “Well, that’s just too good to be true.” So what I’ve started realizing is the minute I started asking people, “But what would change?” And Nathan, $4,000 a month That will, and I am talking about again and again.

[00:25:49] Now, I would say 95 of the pe- 95% of the people that are interested, interested in this offer are women.

[00:25:55] Nathan: Yep.

[00:25:55] Jasmine: So that plays into it. But when I deeply understood that women who still maybe still have their jobs but would like- Mm-hmm … an additional $4,000, or they are stay-at-home moms who want to work while their kids are at school, but they want the flexibility of it.

[00:26:08] Right. $4,000, Nathan, shifts everything in their reality, and that they get to do it from home. And so I started realizing, okay, that there was something, like, deeply embedded here, and so we created the 4K Freedom Formula. We, me, and my husband. So I said, how do you explain this really simple way of walking people through the process?

[00:26:30] And I’m gonna tell you the four steps of the 4K- of the 10K Freedom Formula, but you’re gonna think, Jasmine, that’s, that’s, that’s stupid. That everybody knows that. And so what I’ve done is I’ve collapsed a decade of experience- Mm-hmm … into something formulaic. So what I’m about to tell you is not gonna blow your mind.

[00:26:45] You’re gonna be like, “Okay, and?” So step one is to clarify your message- Mm-hmm … and your niche. Like, this is, this is groundwork.

[00:26:52] Nathan: Yep.

[00:26:53] Jasmine: With so much noise, the way that you cut through the noise is not by being louder, but it’s by being very specific. Mm-hmm. So we’re gonna hone in on who that person is, and we’re gonna speak a message to their pain point.

[00:27:03] Like, we want the nail through the foot type of pain. Somebody who says, like, “Just anything, but get me out of this pain,” that’s the kind of messaging that we want. Or, “Get me the solution. Sell me the dream-” Yeah … “life of my foot without the pain.”

[00:27:14] Nathan: Right.

[00:27:14] Jasmine: And then part two is to create marketing just for that person because now the algorithm has been so specific.

[00:27:21] It’s so good at showing people just what you’re talking about, not necessarily to your followers. Much to the chagrin of a lot of people. So if you are speaking to a specific person about a specific thing, the algorithm will actually show it, maybe not to a lot of people, but to a lot of people who could potentially put money in your pocket.

[00:27:35] Mm-hmm. And then once you have marketing that’s really effective speaking to somebody who wants a solution, then what we do is we move towards engagement. And so a lot of times people struggle initially, like, just to set up a funnel. What do I say? All of the tech involved. That will come, but how about we learn how to have a conversation?

[00:27:51] Right. And so we move them into Instagram DMs. Have a conversation, realize what this person wants, and don’t hesitate to make an offer, and then you can get them into funnels, and then you can get them offers. But in the beginning, it’s like, how do we build trust now? It’s less with a megaphone and more with a handshake.

[00:28:05] Mm. And that’s what we’re seeing. So that main trust-come-building pony is gonna be into DMs, and then you’re gonna get them into the business. And step four of the 4K Freedom Formula is to build systems that scale.

[00:28:15] Nathan: Mm.

[00:28:15] Jasmine: Like, it’s not rocket science. It’s simple. It’s not easy.

[00:28:21] Nathan: Yeah, I think that’s something that I see over and over again in businesses that scale, is that they usually achieve that scale through simplifying- Yeah

[00:28:29] and reducing. And everyone’s like, you know, “Nathan or Jasmine, like, give me the secret to break through- Yeah … whatever number or whatever else.” And, you know, it’s this hard thing where you’re like There isn’t one. Yeah. Like, there’s, uh, you know, it’s, it’s the things that you already know or that you’ve heard repeated over and over again.

[00:28:46] Yep. But actually executed really well.

[00:28:48] Jasmine: Yep.

[00:28:49] Nathan: And actu- like, a level of focus and discipline that most people aren’t used to. Mm-hmm. And because they do things like they listen to podcasts like this, and then they get a new idea, and they run off and go chase a shiny object, and they do something. You know, they’re like, “Oh, someone was just on saying that LinkedIn is the next thing,” or that, you know- Yeah

[00:29:05] whatever else. TikTok Shop is the next thing, and then they jump from thing to thing.

[00:29:08] Jasmine: Yep.

[00:29:08] Nathan: And instead, you’re like, “Look, here’s the four things that matter.” Yep. Nail each one of them. Do it in sequence.

[00:29:12] Jasmine: Yes.

[00:29:13] Nathan: And I promise you it’ll work.

[00:29:14] Jasmine: And then do it, do it again, and again, and again. Mm-hmm. And then continue doing it when it doesn’t work, and continue to do it when there’s crickets because every iteration is actually illuminating the next step.

[00:29:24] Nathan: Mm-hmm.

[00:29:24] Jasmine: And so it, it, it, it, it, it almost happens seamlessly, but it only g- it only rewards those who don’t stop walking.

[00:29:32] Nathan: Right.

[00:29:32] Jasmine: And many people will get the system, and then they just stop. And if anything, if I’ve learned anything in my career is, like, success only goes to those who don’t stop walking.

[00:29:42] Simple, not easy

[00:29:43] Nathan: Yeah. I mean, the first rule of compounding is to not interrupt it prematurely. Oof. And almost everyone interrupts it prematurely. Yes. That’s a, uh… Is that a Buffett or a Munger quote?

[00:29:51] Jasmine: I

[00:29:51] Nathan: don’t know. Both of them. One of those two, but We love them. Both of them, yeah. Okay, so in that specific offer, what does the support look like?

[00:29:58] ‘Cause I think a lot of creators listening are gonna totally understand the clarify the offer- Mm-hmm … um, all that. Okay, great, I now have a, a promise and outcome.

[00:30:08] Jasmine: Mm-hmm.

[00:30:08] Nathan: Oh, 90 days, that’s smart. Mm-hmm. That, you know, all that.

[00:30:11] Jasmine: Mm-hmm.

[00:30:11] Nathan: And I know how to film the videos, and I know how to- Mm-hmm … write the emails, but, like, what do you actually provide on ongoing support?

[00:30:17] Jasmine: It’s as much as what a client wants. So there was the old way of coaching- Mm-hmm … which what we saw a lot of, which would be you’d meet with your coach by 30 minutes once a week. But what we started seeing was that people became inactive about a day or two after meeting with the coach. Or they would say, “Okay, well, I’m gonna- Right

[00:30:32] hold off a little bit and come back.” So what we created is asynchronous coaching. So you are going to be submitting a question to your coach, and your coach gets back to you that day with a video response with your worksheet. So they’re like, “Let’s walk through this. Now, I’ve noticed this in your niche.

[00:30:44] Let’s take this back to- Mm-hmm … your beta testers. Let’s see what they’re saying with this. When are you gonna get this done?” And then you respond Thursday. So that your coach is like, “Hey, Nathan, it’s Thursday, tell me about the responses.” Mm-hmm. So they become almost like a, a project manager staying to the system, keeping you accountable.

[00:30:58] Because what we heard was not a matter of I don’t know what to do. We’ve laid everything out.

[00:31:03] Nathan: Right.

[00:31:03] Jasmine: It is somebody telling you what to do, when to do it, and how to do it. And oftentimes you get… A lot of times people are uncomfortable creating content in a way that they haven’t before, AKA more than once every three weeks whenever you feel like it.

[00:31:17] Nathan: Right.

[00:31:17] Jasmine: So in order for an online offer to work, you have to create content. It’s just conversations to let people know what it is you do, and yet we stop ourselves for fear of judgment, fear of success, fear of failure, whatever it may be. So then you have a coach who’s saying, “Well, okay, what we put in is what we get out.

[00:31:32] So do you wanna put in one post this week, or are you planning on putting in four? What’s your number?” Right. And then they keep you to the four. They’re just like, “Okay, we’ve noticed that there was two post out. You gotta post on Saturday, or we’re gonna miss the goal. Do I have your commitment for that?”

[00:31:43] Mm-hmm. And really it is project management support and accountability.

[00:31:48] Nathan: Yeah, and I, I think being that mirror to reflect back of like you told me-

[00:31:51] Jasmine: Yes …

[00:31:52] Nathan: when you signed up- Yes … that you wanted this outcome in 90 days. Yes.

[00:31:54] Jasmine: Yes.

[00:31:54] Nathan: We reverse engineered all the steps.

[00:31:56] Jasmine: Yes.

[00:31:57] Nathan: Uh, and, and just saying, like, “So what commitment are you gonna make?”

[00:32:00] Yes. And it’s like, “Oh, well, I’m gonna … I’ll have this done by Thursday.”

[00:32:02] Jasmine: Yes.

[00:32:03] Nathan: And so then Wednesday being like, “Okay. So- Yeah … where, where is it?” You know?

[00:32:07] Jasmine: You know, I, um, you and I are, are fans of Sam Parr.

[00:32:11] Nathan: Uh-huh. Sam’s the best.

[00:32:11] Jasmine: And, uh, on his podcast, My First Million, he often talks about… And no, Sam’s fit. Okay?

[00:32:16] The guy’s, like, built. Yes, he is. Like, his muscles have muscles, right? Yep. It’s like his six-pack has a 14-pack. And so, and he posts often about this. And he says that he, uh, subscribes to a daily check-in- Mm-hmm … from, like, a, a food coach. Yeah,

[00:32:28] Nathan: m- uh, My Body Tutor, I think,

[00:32:29] Jasmine: is the company. Yes. Yeah. Okay, okay. I heard this years ago, and I’m driving and I hear this.

[00:32:34] I was like, “Why does Sam need an accountability buddy?” “That’s crazy.” And what I realized was you don’t need the accountability, but to have somebody over your shoulder. And what he would said, he would, he would take a picture of everything he ate, and he would send it to his coach. Like, “I’m keeping accountable to you.”

[00:32:51] And I thought that was bat trash crazy. And what I realized is that it is so effective. Mm. And I kind of ate my own dog food, and I said, “Okay, well, this is… I’m creating an offer for something that I don’t necessarily need for myself when it comes to business, but this is what I heard. The market’s never wrong.”

[00:33:07] And then at the top of 2026, I decide to invest in a rather very high-ticket offer for a nutrition and a fitness coach. And when I told my family what I had invested, they’re like, “Oh, my. Que loca. Oh, my God, you’re crazy.” Like, this is like, what are you doing? And what I realized was my coach is watching every caloric value I input.

[00:33:28] Mm-hmm. Asking me to upload workout videos, asking me to keep track. So I l- it’s like a part-time job, but I have never gotten this result in the entirety of my life. And it feels like- Right … I’ve been dieting for as long as I can remember. So to get a result seeds more desire- Right … to keep the result, and that’s what paying for have- somebody having eyes on your stated outcome, and then that person holds you accountable.

[00:33:50] Nathan: What I like about this is that everyone defaults to the call as a way to provide-

[00:33:56] Jasmine: Yep. You see it.

[00:33:57] Nathan: Yeah.

[00:33:58] Jasmine: You see it.

[00:33:58] Nathan: And, and they either do it in a one-on-one call. Yep. Like, I am your coach. Yep. You’re probably paying me thousands of dollars a month for this to be, or, or say at least $1,000 a month- Mm-hmm. Yep

[00:34:08] for it, it to be worth it for the time investment and everything else. Or we’re doing it in a group coaching format.

[00:34:13] Jasmine: Right.

[00:34:14] Nathan: And that’s like, I feel like that’s optimizing for the information being shared again.

[00:34:21] Jasmine: Again.

[00:34:21] Nathan: Whereas you went straight to it and you’re like, “No, it’s the accountability.” Yeah. Like, you already have the information.

[00:34:25] You already have the playbook. Yeah. It’s the accountability that matters, and we don’t need a 30-minute or a 90-minute- No … Zoom call- No … to get the accountability. No. You actually need those 30 to 90 minutes to do the

[00:34:35] Jasmine: thing. 100%. 100%. And that’s what we, that’s what we realized. And I think that there was a lot, there is a lot of pushback because people come in and they have this preconceived notion of what coaching is.

[00:34:43] “Well, no, if I don’t get my, my f- 30 minute every week”, and I’m like, “Okay, no problem. This is not for you.” The way we actually get the quick results, the way we see people making money in 30 days, is not by a weekly check-in. It is literally y- you send us five questions in a day, and you get five responses back in a day.

[00:34:59] No, we move fast.

[00:35:01] Nathan: Okay, so I’m thinking about w- what else is important in the, this asynchronous accou- like, coaching and accountability? Mm-hmm. Because people are not talking about this enough.

[00:35:09] Jasmine: Mm-hmm.

[00:35:09] Nathan: Like, I, I imagine there’s

[00:35:12] Jasmine: a bunch of things. Are we spilling the tea right now? I, I think we

[00:35:12] Nathan: are. I

[00:35:12] Jasmine: mean, are we, like, making waves, Nathan?

[00:35:14] Let’s go.

[00:35:16] Nathan: Well, because everyone defaults to the exact same models. Yes. And they don’t realize-

[00:35:19] Jasmine: Because this model, Nathan, will knock the air out of your freaking lungs. I am surprised. I, I should probably be wearing veneers. Like, I’m probably walking around with an iron lung after being punched in the back so many times from this business model.

[00:35:30] But yeah, we can talk about that, too. So- It’s hard, dude. It is hard. So- It’s a people business.

[00:35:36] Nathan: Yeah. Uh, okay, so what goes into the accountability behind the scenes? Like, as an operator at scale- Yes … like, how do you pull that off for not just 10 clients or- Yeah … 50 clients, but, but doing it for

[00:35:48] Jasmine: hundreds? Okay, so this is where I will say I am nothing without the team.

[00:35:52] Nathan: Yeah.

[00:35:52] Jasmine: The team are system driven. Mm-hmm. This, the … You have to have, like, operators on operators for this level of success and guaranteed outcomes. So we have an ROI guarantee. If you do the work, and we have our coaches keeping you accountable. Yeah. If you do the work, and in 90 days do not make back what you invested in the program, we’re gonna work with you another 90 days.

[00:36:09] Like, we know it works. Mm-hmm. We’ve just seen it work. And so very few people will do that, but I’m just like, “We don’t mess around.”

[00:36:15] Nathan: Okay, there’s an important thing in your ROI guarantee. I hear people say that, and I think there’s a big trap that they run into, where they say If you don’t achieve this outcome-

[00:36:25] Jasmine: Mm-hmm

[00:36:25] Nathan: in the promised time period, we will give you your money back. And I think that’s a terrible thing to do.

[00:36:30] Jasmine: I do, too.

[00:36:31] Nathan: Because it puts you at odds.

[00:36:33] Jasmine: Yes.

[00:36:33] Nathan: Where now you’re trying to help the client achieve the outcome. Yes. And they’re sort of like, “I mean”-

[00:36:38] Jasmine: Yes … ”

[00:36:39] Nathan: we’ll see.”

[00:36:39] Jasmine: Yes.

[00:36:39] Nathan: You know? Yes. But what, so you had the ROI guarantee.

[00:36:42] Yeah. And I, like, cringed slightly. Yeah. And then you said what it was. Okay. And it was the, “We’ll work with you another 90 days.” Mm-hmm,

[00:36:47] Jasmine: mm-hmm.

[00:36:48] Nathan: And it’s like, oh, no we’re just aligned-

[00:36:50] Jasmine: Yeah …

[00:36:51] Nathan: for the

[00:36:52] Jasmine: outcome. We’re aligned available.

[00:36:52] Nathan: And so it, it’s a, like, I think most people would miss that difference, and it’s a very, very important

[00:36:56] Jasmine: difference.

[00:36:56] Thank you for pointing it out. Thank you for it. But I, I will say, uh, probably, you know, a few times a week, um, I will hear people say, “Okay, well, um, I want the ROI guarantee to be that when I make that money, then I’ll buy the course. So I would like to get access to the hybrid offer. I would like to get access to your program-” Yep

[00:37:13] “your method, and when I make the money, I’ll make it back.” I was like, “Heck no. Heck no. I believe in me, babe.” Yep. “I don’t know if you’re gonna show up and do the work. Like, I will. I don’t know about you.” So, um, but yes, and so the operator’s on operators. And so the, the key thing here is, yes, I sit as CEO, and yes, we still have Social Curator, and yes, there are still DIY courses.

[00:37:31] But my main focus, it’s like I am focusing on one thing- Mm-hmm … and that is a consistent 10K. It is a new business model. It’s forcing me to develop muscles I never thought- Mm … I would even possess. And so I’m thankful. There is a future version of me who’s looking back at me and saying, “Baby girl, good job.”

[00:37:46] Like, “We don’t know how you’re getting out of bed every morning, but God bless.” Yep. Like, you, you, you’ll, you’ll hang, girl. You’ll hang. So, uh, we have a director. Mm-hmm. And then we have a head of customer success. And underneath the customer success, we have lead support, and then we have a team of coaches.

[00:38:00] And right now we have seven.

[00:38:01] Nathan: Okay.

[00:38:02] Jasmine: We like to keep it really small. We wanna make sure that the people that we’re working with understand our core values, are fully signed up, and, and understand. Mm-hmm. They’re all experienced coaches. That’s gonna be, like, a major thing. You have to have street credibility.

[00:38:12] You have to do something on your own and/or coach other people to do it. Right. So they come in, they adhere to our program, and so we have the coaching board. And so what I’m going through is we do all asynchronous communication in Slack. So e- I have purview of everything. I am reading every conversation.

[00:38:25] I am seeing every single client. Whether or not I’m interjecting, that’s neither here nor there. I need to see the trends. I need to make sure that any gaps are, like, fulfilled, and I need to make sure, how are we responding? What is the expectation? Where are we at? And so where I see myself in guiding that team is going in, and every eight weeks, I’m having a coaching board meeting where I get to share a vision, what’s on my heart, what’s on my mind.

[00:38:46] What is our level of accountability? How are we serving these people? So I- it’s pure vision casting for that arm of the business because the operators in it are so fully dialed in. Mm-hmm. And the coaches, the, it works so well because there are people who are made for coaching and maybe not so much made for, like, the drive of building their own book of clients.

[00:39:01] And so this is, like, really satiating and fulfilling for them, and we’ve operationalized that they get to just be in their superpower.

[00:39:08] Nathan: Right.

[00:39:08] Jasmine: Show up and serve, make sure they get it done, and then people, when they get the results, it’s really fulfilling for them. So we have operationalized a part of their business they didn’t really actually want to do.

[00:39:17] They get to stay in their superpower. I cast vision. And then we have the arm that is marketing, and we have the arm that is sales. So sales, marketing, and customer success.

[00:39:25] Nathan: Mm-hmm. Okay. So let’s dive into the marketing side then.

[00:39:28] Jasmine: Yeah.

[00:39:28] Nathan: W- as you bring in these l- you know, these leads, people who are interested, what does the top of the funnel look like?

[00:39:34] Jasmine: Well, okay, so this is a little bit crazy. So I told you that this offer’s been around for six months. Yeah. And in the beginning, I wanted to see, I wanted to break my frame of what was possible.

[00:39:42] Nathan: Mm-hmm.

[00:39:43] Jasmine: So I said, “Can we just launch this thing on a DM funnel?” Like, let me see. Right. Let me build a system. Let me bring my own brain.

[00:39:50] You’re

[00:39:50] Nathan: putting a

[00:39:51] Jasmine: constraint

[00:39:51] Nathan: on it to say- Absolutely … I, I used to sell in all these other ways.

[00:39:53] Jasmine: Yes.

[00:39:53] Nathan: We’re just gonna do this one method.

[00:39:54] Jasmine: Absolutely. And then I set a goal in 2026 to add four different types of funnels. Like, w- whether or not we’re gonna hit it, I like- Okay … I just like it. Come on, let’s play big, right?

[00:40:03] Let’s play big. And I don’t want just an average funnel. I want, like, the mack daddy Cadillac of funnels. Yeah. And I want four up and going. And I watch numbers and metrics like it’s my job, because it is. So this DM funnel was promising enough that we were getting cost per conversations for, like, $4, and then we were dropping in a VSL, and we were watching click-through response rate when people were dropping off, and I kept on iterating on the VSL.

[00:40:27] And this was me still in that proof of concept phase. Mm-hmm. It’s like, can we turn somebody from the internet with the right messaging into a high-ticket offer? Mm-hmm. Does that actually work? And so a bunch of constraints, quite bit of doubt, and then actually seeing that it works. And I’m like, “Huh. All right.”

[00:40:44] January, we introduce a webinar funnel. Now, that’s the school I dwelt in. That’s the world. Yeah. So I tried a few different topics. I think we’re still iterative. I have one solid one, and then I want to introduce more industry-specific style ones, kind of hone in on that messaging, create evergreen funnels and specific ad targeting, because Andromeda is so phenomenal right now.

[00:41:02] Like, it’s so good that, yes, it might cost more for a CPL, but they’re gonna be so much more qualified and more inclined buyer. Mm-hmm. So the more finite I get with… Because the offer works. We know exactly who we’re targeting. Right. But if I say service-based business, it’s less likely to land than if I was like a chiropractor, a doula- Mm-hmm

[00:41:18] a photographer. So that’s gonna be, like, in the future. What we have is a DM funnel- A webinar funnel, and then we have a n- no-show funnel that only exists in email. Okay. So if you sign up, you don’t come, I’m sending a micro-training. And so we’re tagging every single one to say, where is this lead gen?

[00:41:35] Because on average, which nothing to brag about, it’s, like, I would… We’re, we’re working on our show-up rate, but our aver- our sh- average show-up rate is 24%. Yeah. Not ideal, but that means that there’s 76% of the people who signed up that are not getting access. I don’t really believe in a replay. Most people don’t watch it.

[00:41:49] I feel like it’s a waste of time, and then it just kind of, like, sits there. I wanna create something that’s fast and expiring. So I said, “I created a micro-training. You could watch this micro-training,” and if enough interest is sparked, they’re gonna either gonna go back to the webinar or they’re gonna go straight to book a call.

[00:42:01] Depends on how hot that lead is. And so that’s where we’re at right now, and I do believe we’re gonna be creating another funnel around the summertime. And so it’s us, like, creating the system, testing the system, fortifying the system, starting super scrappy- Mm … and just going. I mean, it is so scrappy right now, Nathan, and I feel like, mm, the humility it takes to understand that it used to look one way, and you used to have time.

[00:42:25] And what has changed is there’s less time, more competition, more fake, more noise. How do you serve a specific person with a specific outcome in the quickest amount of time? And I have to say, that’s gonna come at the cost of things being beautiful and branded. It’s, can I get you something- Right … that changes your dang life, and it might be in a black-and-white PDF.

[00:42:43] Maybe. Maybe.

[00:42:45] Nathan: What I respect so much is you getting to, like, the top of the game in the course, community, like, that whole space, and then constantly- … questioning and reinventing and out. So many people get comfortable, and then at some point they realize, like, oh, why, you know, does what worked in 2020- Yeah

[00:43:04] not work today, right? Mm-hmm. It’s like, well, a lot has changed. Yeah. So you’re constantly reinventing. But I, so I wanna go upstream one more notch- Yeah … from the webinar and, and DMs. Are you, is that mostly paid traffic to get people to that? Or is it your organic social posts? It’s

[00:43:19] Jasmine: a mix. Okay. It’s a mix. And I know that, so I, what I wanted to do is to get proof of concept from a warm audience.

[00:43:24] But is that really proof of concept- Mm-hmm … as much as it is, like, people know, like, and trust you have been in the game for over a decade. Right. And they’re gonna be like, “Okay, I get it.” You throw an offer in front of them.

[00:43:30] Nathan: You get results. And they’re like.

[00:43:31] Jasmine: Yeah. Yes. And so, um, what we wanted to do was to start mixing it, but not at the cost of a, of, of our profitability.

[00:43:37] Right. Like, we knew that warm was gonna be converting higher for less. And so we’ve been in, kind of in this, like, transition point now, like six months into it, venturing more and more into cold traffic. Mm-hmm. So yes, we’re running ads. Um, but we keep them as low CPLs. I’m not trying to say like, “I need a mega launch.”

[00:43:52] I’m not on that timeline. Yeah. I’m in the long game here. I would rather focus on getting the right message to the right person at the right cost than me trying to be like, “I need 2,000 people to sign up right now.” Mm-mm.

[00:44:01] Nathan: Yeah. Okay. And then those web- webinars that you’re running, are those real time, top

[00:44:05] Jasmine: live?

[00:44:05] Real time. Okay. I show my phone. You know, like, people always doubt. I always start it with the same. Today is June 27th. I’ll hold it up. Yeah. And we don’t send out the replay because- Yeah … we want it to be real- Yeah … and in time. Mm-hmm.

[00:44:16] Nathan: And is that, you’re doing, like, one webinar a week? What’s the cadence that you do?

[00:44:20] Jasmine: Um, it, it’ll change depending. Like, so for, y- you know, in the month of May, because it was a holiday, we decided not to do one. Mm-hmm. So we’ll, we’ll do them, like, maybe two or three times a month.

[00:44:27] Nathan: Yeah.

[00:44:28] Jasmine: Mm-hmm.

[00:44:28] Nathan: That makes sense.

[00:44:28] Jasmine: Mm-hmm.

[00:44:29] Nathan: Um, I, I like the hold up the phone. Yeah. It’s basically like the, uh, the hostage proof of life.

[00:44:35] Jasmine: Yes. Like, hold up the, the newspaper. It is a newspaper. Yes. I am a real person. Exactly. Exactly. I want- ‘Cause you know there’s, like, all these, like, tricks and people- Oh, there’s- But it’s the trust recession. Mm-hmm. So I find myself having to over-index, and I’m okay with it. Right. Because gangsters are okay over-indexing.

[00:44:47] Like, I’ll show you. I’ll open my kimono. You’ll see it all. Yeah. Like, you wanna play this way? Let’s go. Mm-hmm.

[00:44:52] Nathan: Okay, so what else are you doing to over-index on trust?

[00:44:55] Jasmine: Uh, go- going live. Mm. Noth- It, it’s unrivaled. It’s unrivaled because everything now is edited for the .6 second attention span.

[00:45:03] Nathan: Yep.

[00:45:03] Jasmine: Like, every good editor will tell you to move the frame .6 seconds for a short-form vertical video.

[00:45:08] And so our brains are shifting. So when you are going live, when I’m going live on Instagram, and then there’s, like, a, a brain fart, or somebody sneezes in the background, or if I bring somebody on camera with me and they’re, like, in a bathrobe, and you’re like, “Oh, my, oh, my.” And so pe- when people get to see the real un- literally unfiltered version of you, their trust in you just raises.

[00:45:27] This is unrivaled. Mm. So outside of in-person events, which are hard-

[00:45:32] Nathan: Yep …

[00:45:32] Jasmine: and expensive, going live is the second-best thing. Mm. And just bringing people on, talking to them, seeing them, report, like, re- reiterating their question to make them know that you saw them and you heard them and you’re serving them, game changer.

[00:45:47] Nathan: Mm. Yeah, it’s so interesting because- As I’ve been, you know, taking social content a little more seriously, something that my team kept pointing out is that when I deliver, like, to the camera-

[00:45:57] Jasmine: Dude, same …

[00:45:58] Nathan: all of that, it’s-

[00:45:59] Jasmine: Same … th-

[00:45:59] Nathan: they’re like, “Nathan- I know … you’re doing your speaking voice again.”

[00:46:02] Jasmine: Yeah, they call it my professor voice.

[00:46:04] Oh, yeah. “Hi, welcome. I’m Nathan Congett now.” ”

[00:46:07] Nathan: In today’s episode.”

[00:46:08] Jasmine: Yes.

[00:46:09] Nathan: And so we started doing more where we’ll just be sitting in a podcast studio. Yes. Thankfully, we have lots of podcast studios at

[00:46:15] Jasmine: Kit. Yes, swag. You know? Yes, Kit, let’s go.

[00:46:17] Nathan: And, uh, they’ll just be like, “Ask questions.” And sometimes I’ll slip into it, and they’ll be like-

[00:46:21] Jasmine: You did it

[00:46:21] Nathan: “You’re doing it again.” Yes. “There’s no cameras here.” And I had one where like, uh, I was talking about ano- another podcast called TBPN that sold to OpenAI, and I was talking about that story. And I watched the clip back, and I was like, “This is bad.” Like, the retention, you know, like, I’m, like, looking up. I’m li- you know.

[00:46:40] And that did, like, s- 50,000 views. Mm-hmm. And I was like, “Wait a second. How did that do really well?” Mm. And they’re like, “Because it was an interesting story- Yeah … and you came off as authentic.” Real. Mm-hmm. “It came off as real.” Mm-hmm,

[00:46:48] Jasmine: mm-hmm.

[00:46:50] Nathan: And so it’s so interesting of, like, changing when we think, “Okay, the bar is here.

[00:46:54] I’ve gotta-

[00:46:54] Jasmine: Oh, yeah …

[00:46:54] Nathan: show up in that way.” And it’s like-

[00:46:55] Jasmine: Oh, yeah …

[00:46:56] Nathan: no, you just- No … you need to connect

[00:46:58] Jasmine: And if you can hold somebody’s attention… So actually, here’s, here’s the tea. Here’s stuff that, that the iterative process and, like the iterative process and the ideation process. I often sit with my husband every morning.

[00:47:08] What we try to do at minimum is to get, like, about 21 minutes undisturbed before our daughter wakes up.

[00:47:13] Nathan: Okay.

[00:47:13] Jasmine: So we make our coffee, and we’re, like, silently sitting in the living room, and one of the things that I had said is, like, I see so much of live, real, long form being, being a thing, and then obviously cutting it into micro-content that serves in different ways, but, like, people going deep.

[00:47:27] And I’d always joked, I’d always joke growing up. I’m like, “I belong on QVC.” Like, I can talk. Like, I can sell you that iced coffee from Blue Bottle. I will tell you about that bean roast. I will hold it up. Whatever it is. I’ll make sure that happens. Whatever it is because I understand the power of connectivity with people.

[00:47:41] Mm-hmm. I’m a, I’m a human. Like, everything I do is rooted in sales psychology. Like, psychology of the brain. What gets somebody to buy? Literally buy a theory, buy a vote, buy ideology, buy a religion. I’m so fascinated with this. And so I had said that I firmly believe that despite my best efforts in creating content, both with a DSLR and an iPhone, and doing the preplanned, not planned, off the cuff, I said, “I think it would be unrivaled if I had a call-in show.

[00:48:08] And I do a call-in show, and this is what I do. This is, like, the Latina version of Dave Ramsey.” Yep. Maybe not so, uh, political on one end or the other, but it’s like we’re talking business. Right. Like, this is what we do. And I was like, “I kind of feel like that would be my jam.” And he’s like, “Well, then what’s stopping you?”

[00:48:22] And I was like, “Well, I, like, it’s a studio. It’s who’s gonna vet these callers? Like, how does it look?” Mm. And so then I made the commitment that I’m like, “No, you’re going back to always how you started.” It’s like you take what you have. And so I went back. So three years ago, I did this thing called Coffee and Conversations.

[00:48:36] Every Tuesday at 9:00 AM, I would get a French press. I would make coffee, and people would come in and ask questions, and I would do it for about 30 to 35 minutes, and it was so good. Why did I stop doing them? Mm. The pandemic. I became a mom. It just was a lot of things. I think going back to that, and I wanna earn the right to make an, a strategic investment in maybe renting a studio or renting a producer or working along those.

[00:48:56] But until I do that, watch me just, like, kind of like slave away, Ed slay, on Instagram Live refining a skill set that I think sets me apart from other people. So what’s the big takeaway? Not that Jasmine knows how to talk. It’s what do you have in the palm of your hand? What skill set do you have? What makes you different?

[00:49:12] Let, different is better than best. And so whatever people have right now, to use that, position that in light of your offer. And so just getting super scrappy right now in all of those ways, because we are really hedging. It is a new arm of the business. I’m gunning for profitability- Mm-hmm … where traditionally a people person business is less profitable.

[00:49:31] And I’m like, “Well, how do we break the frame of that? What kind of restrictions do we have to have? Con- uh, constraints do we have to have?”

[00:49:35] Nathan: Constraints.

[00:49:35] Jasmine: Mm-hmm.

[00:49:36] Nathan: Yeah. Are there constr- like, are there constraints that you’ve put on it in order to maintain profitability?

[00:49:40] Jasmine: Oh, absolutely. Like, uh, if the DM funnel isn’t producing over a certain percentage, we’ll cut the spend.

[00:49:45] We gotta make- Mm … new inventory. If our closers are not closing at 35%, we’re gonna de-prioritize you. Like, if you aren’t showing up and setting your own calls and finding ways to win, you’re gonna be de-prioritized. It’s, it is, it is truly American. Like, you cut me open and an eagle flows out. This is, like, purely democratic.

[00:50:01] Results over feelings, 100%.

[00:50:04] Nathan: Yeah, and I love that you are all in on the content and everything else- Yeah … but watching the metrics all the way through. Oh, yeah. ‘Cause you’re building… Like, I, I can picture the engine that you’ve built for this business.

[00:50:14] Jasmine: Yeah.

[00:50:15] Nathan: It’s beautiful. Okay. Let’s dive in on the DM funnel-

[00:50:17] Jasmine: Okay

[00:50:17] Nathan: specifically.

[00:50:18] Jasmine: Okay. ‘

[00:50:18] Nathan: Cause I think that there’s a lot of people who have sold primarily through email or webinars- Yeah … and like that are like, “Wait, we gotta talk to people individually?”

[00:50:25] Jasmine: Mm-hmm.

[00:50:25] Nathan: But then they also experience the one-on-one. What are some of the mistakes that you made in the DM funnel early on that you’re like, “Okay, if I could go back,” and be like, “Hey, Jasmine.”

[00:50:33] Jasmine: Uh, well, the crazy thing is- … is I would be responding to DMs, and most people were thinking it was AI.

[00:50:39] Nathan: Mm.

[00:50:39] Jasmine: And I was like, “Oh, man.” Like, what… So I found that the thing that was gonna be really effective is just to send a voice memo. And so I realized that I talk faster than I type.

[00:50:48] Nathan: Yep.

[00:50:48] Jasmine: And- I

[00:50:49] Nathan: believe you.

[00:50:51] Jasmine: Most people listen to my podcast and they’re like, “I listen to other people’s podcasts at 1.5, but yours I’m listening at 0.75.”

[00:50:55] Nathan: I think this episode is the single highest value per minute- … it’s ever been on my show. You know

[00:51:00] Jasmine: I like to win, Nathan.

[00:51:02] Nathan: I know

[00:51:02] Jasmine: you do. Give me another thing to win at. Um, so one of the things that I realized was that if I’m sending a voice memo, that actually worked really well. And then I realized it’s, like the uglier I looked, AKA it’s like 6:47 in the morning and it’s kinda dark and my hair is messy from the gym and I’m wearing a big oversized sweater.

[00:51:15] Yeah. And I’m like, “Listen, Natasha, are you gonna let fear get in the way or are you gonna make a decision? Let me know.” Like, people are like, “Oh, my God.”

[00:51:24] Nathan: Right. ”

[00:51:24] Jasmine: She literally just showed up and did that.” And I think that we always think about like scaled conversion, which, hey, I am all for. I love that. But there’s also the power of seeing somebody and then getting them to trust so that if they get on a call, um, they’re fully bought in.

[00:51:41] It’s just a matter of like, let’s make it official. That’s different. And I like… And I’ll, I’ll do, I’ll do whatever it takes to get an outcome. And so, uh, I think you know that. Like, for those people who don’t know, I kind of stalked Nathan. He, uh, was recording a podcast in Los Angeles.

[00:51:57] Nathan: Yep.

[00:51:58] Jasmine: I got tickets to come to the podcast because I wanted to ask.

[00:52:01] I need, I wasn’t asking him a favor. Uh, not even a favor. I was gonna ask for like a pretty big thing. Like, I wanted to get specific things from Kit to facilitate a course I was having- Mm-hmm … for around funnels and course building and all that other stuff, and I knew that I just couldn’t get to you just by email or like DM.

[00:52:18] And so bought tickets to the podcast. My husband and I arrived early, sat front row or second row, and then we dispersed and you had an outdoor cocktail event on the rooftop. Yep. And so I realized that most of the people were using the logical way to exit from the back and up the staircase, but I noticed that you had left the stage, went behind the stage, and somehow ascended.

[00:52:40] And I was like, “If he went up, I don’t know.” I’m

[00:52:42] Nathan: going that way.

[00:52:43] Jasmine: So then everybody’s walking this way. I jump the stage, and then I follow Nathan up to the top. Yep. And I’m one of the first people, and I’m like, “Hi. I’m totally creepy, but I need to ask to see if, what Kit can do, uh, for- Yeah … this particular course,” and then look what happened.

[00:52:56] So all to say, I will do whatever it takes to, to work, and if that is an effective DM funnel that has me sending voice memos, like watch me send voice memos. I

[00:53:05] Nathan: love that. One quick thing on that story. So Haley, who runs all of our events, Creator Community at Kit, and, uh, she and I have worked together for like, I don’t know, eight years now.

[00:53:13] It’s a long time. Um, when she saw you in the audience, she’s like Jasmine Star’s here. And then I, I think, if I remember correctly, when you came up, she’s like, “Oh, you must be here to talk to Rachel.”

[00:53:25] Jasmine: Yes.

[00:53:25] Nathan: And ’cause you- Yes … and then you’re like, “No, to Nathan.” She’s

[00:53:28] Jasmine: just like- Okay, we have to fill the audience in.

[00:53:29] Hold on. The podcast you were hosting with Rachel Rodgers. Yes. And so Haley’s like, “Jasmine’s not here for Nathan.” No. No way.

[00:53:34] Nathan: Nathan doesn’t have that cool of fans. But- But I love the dedication to make things happen.

[00:53:41] Jasmine: Yeah.

[00:53:41] Nathan: Like, I’ll give an example of this. Must’ve been like 2015, 2016, I was trying to get, uh, Tim Ferriss as a customer for Kit.

[00:53:49] And, uh, my friend Ryan Delk was like, “Look, don’t try to reach him.” And we had a few friends in common. We’d talked on the phone once, like we had connections, but he’s like, “Tim is not the person who’s gonna switch his email list from GetResponse over to Kit. You have to figure out who his right-hand person is- Oh

[00:54:03] and then meet with them.” And so I figured out there was this guy, Adam, who lived in Colorado, and then I was like, “Oh, I gotta figure out a reason to be in Colorado.” And Ryan’s like, “That’s a reason.” That’s, you know? Yeah. And so I just emailed Adam and I was like, “Hey, I’m gonna, um- … you know, I’m gonna be in Boulder-

[00:54:17] on either this day or this day. I’ve set up meetings with either one. You know, are you in town either, either day?” And he’s like, “Yeah, this one would work.” And we ended up, he had his son with him. We ended up like going for a walk around the block. He had the stroller. Like, but we just connected-

[00:54:29] Jasmine: Mm-hmm …

[00:54:29] Nathan: and built it from there, and it was all about like show up in person, make these things happen.

[00:54:34] That’s right. And I think too often we’re trying to think, maybe it’s like back to the funnels, conversion rates, efficiency, like that brain takes over.

[00:54:43] Jasmine: Mm-hmm.

[00:54:43] Nathan: And you’re like, “Well-

[00:54:44] Jasmine: Mm-hmm …

[00:54:45] Nathan: I don’t actually know what opportunity will come from it.” Mm-hmm. And it’s like, look, if you landed- Two clients on Tim Ferriss’ level this year-

[00:54:53] Jasmine: Amazing

[00:54:54] Nathan: like, that would change- Game over … the business.

[00:54:55] Jasmine: Yep.

[00:54:56] Nathan: And so maybe you should be willing to get on a plane for it. Yeah. Maybe you should be will- you know, whatever, drive across town. What- whatever the action is to go above and beyond. Yeah. And it works so well. Like, as an example, Tim has been on Kit for the last eight years now, you know?

[00:55:12] And he’s one of our biggest customers, and-

[00:55:14] Jasmine: See, but here’s- … so much has happened … what you need to do now. You need to go and put, like, CIA agents around- Well- … in Boulder, protect h- his number two’s house because- … we don’t want nobody else setting up walks with

[00:55:26] Nathan: him. You know what I’m

[00:55:27] Jasmine: saying? That’s right. No, I’m just kidding.

[00:55:28] I’m just kidding. Uh, he now lives in- In- … Albuquerque That’s right. That’s

[00:55:29] Nathan: right. And you should go there. Um, okay, so I wanna make it really practical with the offers ’cause I’m still fascinated by- Okay … the outcome and, and shifting that. If we can go with an example, maybe using Kit as an example.

[00:55:43] Jasmine: Mm-hmm.

[00:55:44] Nathan: ‘Cause we do something that is very… I’m gonna get in trouble with my marketing team for saying this, but it’s generic, right? In the sense that we… Like, you can use Kit 100 different ways-

[00:55:54] Jasmine: Okay …

[00:55:54] Nathan: in 100 different industries and all of this. Like, whatever you’re trying to do, we probably have the software to accomplish it, so long as it’s generally audience related.

[00:56:03] Okay.

[00:56:04] Nathan: And so what I’m thinking about is if you were to design an offer in this style- Mm-hmm … for Kit or another company along those lines, like- Mm-hmm … how would you think about packaging that and saying like, “Okay, what’s the outcome we’re creating? What’s the timeline-

[00:56:17] Jasmine: Mm-hmm …

[00:56:17] Nathan: on from there?”

[00:56:17] Jasmine: So what does your, what does your dream client want?

[00:56:21] Nathan: Uh, they want to grow their email list.

[00:56:24] Jasmine: But really- In order to- … at 2 o’clock, at 2 o’clock in the morning they wake up and they’re like, “Ah, gotta grow that email list.”

[00:56:29] Nathan: No, they want income.

[00:56:30] Jasmine: That’s right.

[00:56:30] Nathan: Right. And so they- You know, pr- probably very similar to, to your dream client in the sense that they, you know, there’s some freedom number.

[00:56:37] If I could make- Mm … $1,000 a month on the side. If I could get to- Mm-hmm … you know, if we go more to the professional creator, someone who has traction, then they’re like- Mm-hmm … okay, how do I get to that 10K a month?

[00:56:47] Jasmine: Mm-hmm.

[00:56:47] Nathan: On from there.

[00:56:48] Jasmine: Mm-hmm. So first things first, I would set up as many calls… I like the, I like 100.

[00:56:54] I don’t know what that is. I just like it. You could set up 100 calls with people who you think are your dream demographic. Obviously, we all want the Tim Ferrisses of the world. Mm-hmm. But at the end of the day, who are not your whales but not your minnows, like, who are your dolphins? Mm. These are the people, like, they’re sticky enough, they’re not gonna, like, move away.

[00:57:09] They have just enough to keep, like, that, that amazing- Right … care that entrepreneurs always have. Yeah. Like, you wanna speak to the dolphins, 100 dolphins, and ask for what is, what is their magic number? If what you believe is they want money, but here again- Mm-hmm … that’s a hypothesis. First we need to ask.

[00:57:22] Right, we have to test it. Like, yes. So let’s just say you felt pretty, uh, certain with the hypothesis. Then you would have to understand, well, what is that number? Mm-hmm. And then w- how do they want to get that number?

[00:57:32] Nathan: Right.

[00:57:33] Jasmine: And so w- what we think is, like, we apply our, our service, our commoditized product- Mm-hmm

[00:57:38] and say, “This is how they want it,” but we’re not actually sure. But if we can find a way to help them reach their financial goals in a way that they want, and we could use our SaaS offering to do that- Right … well, then, then we have something cooking there. But I couldn’t necessarily go and, like, prescribe, like, “This is what people want.”

[00:57:53] But I can generally tell you that there’s three main drivers. People want more time. Mm-hmm. They want more money, influence/power.

[00:58:00] Nathan: Right.

[00:58:00] Jasmine: And so w- until you’re actually certain what those main drivers are for the dolphins, you might be surprised. It might be influence. Mm-hmm. There is, like, this insatiable thing right now that, like, mattering really matters.

[00:58:12] And it’s not a driver for me. Perhaps early in my career it was. Perhaps when I was in that dolphin status, like, I wanted to matter, and being able to matter. So how do we reverse engineer the offering that Kit has to actually help them matter? How do they get brand exposure? How do they get more light on what it is?

[00:58:27] Right. And so based on what it is they want of those three main kind of levers, what that magic number is. And so let’s just say it is influence. It’s like maybe they want 100,000 followers. Mm-hmm. Okay, and then on what specific platform? So how do we reverse engineer using what you provide to get them there?

[00:58:41] What are the strategies? What are the three steps that will help them convert their newsletter follower list into followers, but followers who actually engage? Because if they engage, then it incites other people to come in and do the very thing they want. So it’s like the whole strategy is, how do we get what you provide- Mm-hmm

[00:58:54] to get somebody into action so that person gets a result? The more definitive that result becomes in a specific amount of time, then people are like, “Heck yes.” And so that actually is power. Power is doing something that somebody told you to do, and you got the result that you wanted. Mm-hmm. Now you say, “Whatever you tell me-

[00:59:13] I’m gonna continue to do.”

[00:59:14] Nathan: Yes.

[00:59:15] Jasmine: And so as a provider, if somebody says, “I trust Kit. I went through this offering. I got this really, this result that I wanted. Tell me what’s next. How do I say more? How do I do more? How do I talk more?” I think it’s pretty fascinating what, uh, Alex Hormozi has done with school.

[00:59:30] Nathan: Mm-hmm.

[00:59:31] Jasmine: There’s a lot of dominant power in a community because what they’ve done is they’ve just created a very formulaic, this is how you make your first dollar online.

[00:59:39] Nathan: Right.

[00:59:39] Jasmine: And then they give you the steps to $100, $1,000, and the aspirational model of $100,000. But what happens is they don’t start something like, “We’re here to give you a million dollars from an online community.”

[00:59:48] Not at all. What do they do? It’s levers of power built over trust and results. Fascinating. Mm. It’s psychology.

[00:59:55] Nathan: Yeah, I love that. I think there’s- So many things, like, w- as you’re talking, it makes me think about our ideal client is actually not the person who has o- 10 subscribers or 100 subscribers. It’s probably the person who has 10,000.

[01:00:10] And so if we were to make an offer and, and, you know, do those 100 calls, it would be about how do you get that person who has 10,000 subscribers on their email list to then, you know, figure out exactly what they want and then create that outcome. Yep. Yep. And so we would get more specific. And then we’d probably go, I g- I guess, you know, we’d slice it this way based on audience size, and then we’d slice it another way based on verticals and try to understand, yeah, what, what outcome we want to go

[01:00:34] Jasmine: for.

[01:00:34] It’s so funny. You approached, you approached it exactly like an engineer. I do. You literally, you literally went sideways. I did. Segmented. I was like, he literally just- … uh, drafted the exact methodology. You saw the spreadsheet- I did … play through in my head. I did. I did. I did. I did. I saw the roadmap actually happening- Yep

[01:00:48] unfolding in front of us.

[01:00:49] Nathan: Yep, that’s, that’s how it works. I wanna dive in on messaging. Okay. ‘Cause that’s something that you’re talking about in your offer, how getting everyone very, very clear on messaging. Mm-hmm. You’re helping all your, all your clients with this. Mm-hmm. Like, how do you approach that for your own offer, and, and what matters so much in reaching the right buyer?

[01:01:04] Jasmine: Okay, so there’s two ways that I would be discussing this. Because w- when you’re just beginning and getting a digital offer, I am not re- I, we gotta get the message right for a specific person. Okay. And then as you mature in business, you understand it. In order to go to cast your net wider, you’re gonna have to start speaking a little bit differently.

[01:01:18] Mm-hmm. And so, uh, I think of, in terms of three different groups of people when it comes to any strong offer. And there are people who are aware they have a problem and are actively looking for a solution. There are people who are aware they have a problem, but they’re not really looking for a solution because they’re not sure it exists or it’s outside of what they can imagine.

[01:01:37] And then there’s people who aren’t aware that they have a problem. So in all of that messaging, I’m not gonna be focused on the person who isn’t aware, because the amount of information that it would require for me to educate them on w- what they don’t know. So for instance, if I wanted to focus on the person who doesn’t know they have a problem, I would say, “You feel really stuck in your 9:00 to 5:00, and you hit a financial level.

[01:02:00] Like, there’s no way you can get past this.” And so I have to break their frame of reality, I have to sit outside of their universe of what they think is possible, cast a vision, and then get endless pieces of content building a new set of belief. Mm-hmm. Then once they actually believe, I have to convert them.

[01:02:17] That, to me, is not the game I want to play, but a lot of people are there. In fact, anybody, like in the big tech AI, like right now, for people who are in the game, we understand that AI is, i- is, is the future. Right. But the amount of people actually using it is so, so, so small, and what people are talking about is like the little people know, it’s like negative.

[01:02:33] Like, we don’t want that. Mm-hmm. So AI, early AI founders have to be in the game of, “We need to break your frame of reality. We need to teach you-” Right … “why it’s important and what’s possible.” We saw this happening with NFTs back in like 2020. Yep. They had to, “This is what an NFT is. It is a digital piece of landscape.”

[01:02:47] So that amount of push, no thank you. Okay. That’s not in the business that I wanna get into. So there is the person who’s aware of the problem and is looking for a solution, and so I am creating content with a message that is, you want to start a business and you’re not exactly how, because you’re a service provider.

[01:03:03] Or you wanna start a business, like you have people following you, and you know you have a lot to say and people trust you, but you’re actually not quite sure what the business should be. Okay. Then there’s messaging of, “I know I have a problem, but I am not aware of the solution.” That messaging changes ever so slightly of, there is a life that is different from what you see.

[01:03:21] And while you think it is impossible that you would be able to create 10 consistent 10K months- Mm-hmm … this is how you do it. And so that two types of messaging works really effectively. So when people put out their offer, we wanna know there are people who are looking for that. Right. You speak to them differently than the people who know, but they actually don’t believe that an offer or a solution exists.

[01:03:41] Nathan: How do you seg- Like, how do you segment someone into one of those buckets?

[01:03:44] Jasmine: Well, good for us, Meta and Andromeda. Like, that’s mostly… Like, I mostly speak to those platforms because I know that there is- Mm … really effective ways to do it on YouTube. I just haven’t dipped my toe. It is a, it’s a big beast, and I really, really wanna start focusing that, like, later in 2026.

[01:03:58] So right now, like, how do you eat an elephant? One bite at a time, and my first bite is gonna be with Meta. And so Andromeda is so unrivaled in serving up content. And so the words that you use, the caption that you write, um, any time that you add closed captioning, all of that is being read by the algorithm, and it’s serving it up to people who are kind of going into the, “Can I create a course?”

[01:04:18] Or, “What does digital marketing look like?” All of that stuff is being spoken to because that’s what we’re using in our copy for the ad itself.

[01:04:24] Nathan: Okay, if someone has never heard the word Andromeda before-

[01:04:26] Jasmine: Okay …

[01:04:27] Nathan: like, break that down.

[01:04:28] Jasmine: Um, in the most simplest form, and I know somebody who’s really in the game- Yeah

[01:04:31] is gonna be like, “You said it wrong.” That’s okay. Okay. An- Andromeda is the way that Meta is serving up their ads. Andromeda is the version of what is looking at what you’re creating as an ad. And this newest version is called Andromeda. And Andromeda, I like to think of her almost like a siren at sea.

[01:04:47] She’s hearing what it is you’re saying, and saying, “This person needs to hear it, and this person needs to hear it.” So the broader the messaging, “I hope you build a business,” it’s probably not gonna be served up because it’s just still so broad. The more specific you get with the message, and then the cleaner the transformation, what is it that somebody really wants?

[01:05:04] And, um, I would be cautious. I know what my people want, and what they want is financial freedom. But I can’t use that in an ad, because it triggers. Like, that’s just too broad. Yeah. And so what we’ve got is more honed-in messaging. What is it that you want? Financial freedom, yes, but is it 5K a month, 10K a month?

[01:05:20] There is a way to do that. And when you start mentioning those types of things and just, like, online resource creation, um, online offers, digital marketing, all of those words are being read and served up to people who have already previously consumed that style of content.

[01:05:33] Nathan: And so you’re making sure that, that that is going to a particular reel, and it’s in the, the captions and all the details for that reel, that you’re then serving as an ad.

[01:05:40] A

[01:05:40] Jasmine: reel, carousel, or a static image. Static images will still kill. That’s the crazy thing. Okay. Oh, yeah, still. One, one really strong photo is better than a mediocre reel.

[01:05:48] Nathan: Hm. Mm-hmm. Okay.

[01:05:49] Jasmine: Mm-hmm.

[01:05:50] Nathan: And so then you’re, you’re having those perform well as organic content and then running them as ads if they do well?

[01:05:54] Or how do you approach that? Uh,

[01:05:56] Jasmine: we’re testing it. So, um, sometimes we’ll put a piece of organic content, and I’m like, “That, that did surprisingly well.” Obviously, we’re gonna turn that into an ad. Yeah. We might change the caption a bit. But we are starting off with a, here again, messaging. Like, going to my organic audience, being like, “Do you want consistent 10K months?”

[01:06:10] It seems a little bit out of line maybe, because what I mostly speak about is, like, marketing- Yeah … branding, sales. So the ads are very specific and tailored to somebody who may or may not have that much familiarity with me.

[01:06:20] Nathan: Okay. And then from that content, is it… Like, how are you going from there to DMs?

[01:06:24] Is it usually a ManyChat, like comment a word, hand-raiser type of thing, or-

[01:06:28] Jasmine: Yeah, but I- …

[01:06:28] Nathan: reply to a

[01:06:29] Jasmine: story? I believe in, like, the human component- Yeah … because we ran split tests with ManyChat and, like, me, or me and my assistant. And, like, we’re talking about massive. Like, over 80% difference in people responding.

[01:06:40] And they always say speed to lead, which how fast can you respond really matters. And yes, it’s true, but not speed to lead at making somebody not trust you.

[01:06:49] Nathan: Right.

[01:06:50] Jasmine: And that’s what we notice. So I’m like, I would rather just sacrifice a little bit of the response time and then have that person… Like, sometimes people come back and be like, “Oh, there was a typo.”

[01:06:57] I’m like, “Great. Well, at least they know I’m real,” you know? Yeah. So I- it’s gonna be human, for sure.

[01:07:01] Nathan: And then when you’re responding in, with a, a voice memo or something else- Mm-hmm … are you batching that in some way, or you’re just- You’re just jumping in when you have time? How does, how does that look? So,

[01:07:11] Jasmine: okay, this is like, that’s a really good question.

[01:07:12] Okay, so the real real is there are people who are just so clearly qualified- Right … that when somebody comes in and, like, they have a large following, or they have a service-based business, or they’re, they, they have a digital offer and they’re like, “I’m, I’m just kinda struggling at that 3K mark or 5K mark”- Mm-hmm

[01:07:25] I’m going to be hand-holding and, and expediting with videos and, and voice memos. Right. Like, let’s just get you on the fast track. There’s other people that would require a little bit more work, so I might just… And you have, like, um, uh, in Instagram you have saved replies, or in Meta you have saved replies.

[01:07:38] Right. So I will just type in, like, three letters, and then I know that’s the response that I’m sending in. Yeah. So I don’t have to hand type everything. So the quick replies are a game-changer.

[01:07:45] Nathan: And what I’m realizing is you have different inboxes in Instagram.

[01:07:48] Jasmine: Yes.

[01:07:48] Nathan: And so you could have someone on your team very easily be like, “Hey, this is going into the inbox that you need to pay attention to.”

[01:07:55] Jasmine: That’s if I was way more organized. Like, I’m just being real. Like, you have your primary, you have your general, and then you have your requests. Right. And I know that, like, I probably should go through and indicate who’s primary- Mm-hmm … and who’s general. It’s just, I d- I don’t. And then when you run Meta ads, those, if you have a response, like comment the word this, it’s not ManyChat, but Meta has to run it.

[01:08:13] Right. And so if Meta’s running it, they’re dropping it into the primary account. So I’m like, “Ah,” like-

[01:08:17] Nathan: And they’re, they’re all in primary.

[01:08:18] Jasmine: Yes.

[01:08:19] Nathan: Yeah.

[01:08:19] Jasmine: Yeah.

[01:08:20] Nathan: Yeah. So. That makes

[01:08:20] Jasmine: sense. Mm-hmm.

[01:08:21] Nathan: Okay, final thing. I wanna dive into a specific offer, ’cause you and I have a friend in common in Franny Wilson- … from Ampersand Studios.

[01:08:27] We love her. We love her. She’s the best. I was at her studio yesterday. I had this interesting experience because I had her on my show- sometime last year. Mm-hmm. And I was interviewing her. I w- actually for my book, and I was like, “You know what would be fun? If I interview you for the book, and we just run it as an episode.”

[01:08:44] Jasmine: That’s good.

[01:08:44] Nathan: And so I was learning about, you know, her, like, the iterations through her service-based business, how she’s productized it over time. And at the exact same time, she’s planning her ready-to-post-

[01:08:54] Jasmine: Mm-hmm …

[01:08:54] Nathan: content, uh, subscription for small businesses basically. Mm-hmm. She l- she’s like, “Hey, we’ll come-” And

[01:08:58] Jasmine: she planned that while she was in my mastermind.

[01:09:00] Nathan: I know. Okay. So that’s the thing, where she’s like, “Okay, I’m going to go and show this.” She’s like, “Here’s this thing. I’m gonna show it to Jasmine-” Mm-hmm … “you know, tomorrow,” or something like that. “What do you think?” Back and forth. And so it was… Like, she showed me a bunch of the changes and edits that you made, and then I…

[01:09:14] Like, that took it from, like, “Oh, that’s a cool idea,” to, “I wanna buy it.” Mm-hmm. And I actually just hit the one-year mark. We just renewed for the next year.

[01:09:21] Jasmine: And your content’s amazing.

[01:09:23] Nathan: Thank you. So w- um, I’m curious, like, the things that you noticed, like that you tweaked in her offer or those types of things that you said, like, “Okay, here’s how it’s coming in,” versus

[01:09:33] Jasmine: what was meant.

[01:09:33] Okay, to the best of my memory, one of the things that stuck out was, like, how do we systematize?

[01:09:37] Nathan: Yeah.

[01:09:38] Jasmine: Because death by decision really ruins a client relationship. Mm-hmm. And when, um, you became… Like, you became the avatar, and I’m like, if, if working with Nathan is a dream, and she said it was, so I mean, I’m not being, I’m not being nice.

[01:09:49] I’m just being honest. She’s like, “How do we work more with, with the, the Nathan avatar?” Right. And I said, “Well, he is very successful. He’s very busy and makes so many decisions in a day that what you want is to have him look at something and clearly say, ‘I get it. I want it. Make it fast and give me the deliverables.'”

[01:10:05] Right. And so in the beginning, there was a lot of options. “Well, you could do this, or you could do that.” Yeah. “No, you could do this, and you could do…” And I’m like, “Oh, my God. If there’s more than, like, three here, it’s gonna be too much.” So we just went back down and said, “What do they really want?” Mm-hmm. “Where are you most profitable, and then how can you sh- systematize on the back end?”

[01:10:20] Because I think with, with the thing with art, it’s, it becomes hard to systematize because it’s a flair. And I’m like, “Babe, we’re running a business. N- we’re not a docent in a museum. So let’s make this so that it’s optimized for your profitability, for the ease of the client, and then make them have a long LTV.”

[01:10:34] And here you are a year later- Right … and that’s LTV. Like, that’s chef’s kiss. Like, that’s the dream.

[01:10:39] Nathan: Yeah, and so I saw the first version of it, and she wasn’t pitching it to me or anything like that. She was just like, “Hey, here’s the thing I’m working on. W- what do you think?” Which as a side note, is a great way to-

[01:10:48] Jasmine: Great.

[01:10:49] Nathan: Perfect … to

[01:10:50] Jasmine: pitch

[01:10:50] Nathan: something. Perfect. That’s how I always do it when I’m trying to hire someone. I’m like, “Hey, I, I have this role. Do you know anyone that might be a good fit?”

[01:10:56] Jasmine: How can I make this job description a

[01:10:58] Nathan: little better? Maybe, maybe you. Would you want… But with that, you’re right. It was a ton of options- Mm-hmm

[01:11:05] and a lot of decisions to make, and I… it seemed complex- Mm … both for her to fulfill- Uh-huh … and as a client. Uh-huh. It’s like I, I need, I don’t need any more complexity in my life. Yeah. And so then after she, you know, workshopped it with you in the mastermind and came back and said, like, “This” It was like, “Oh, so I can just click a buy button- Mm

[01:11:24] and then I get this outcome?”

[01:11:26] Jasmine: Mm-hmm.

[01:11:26] Nathan: Right? I have… You know, I need to give you 90 minutes to two hours of my time- Yep … every couple of months. Yeah. And then you’re going to drop a reel every single week that’s, like, authentic to me. Yeah. I don’t have to do it any- like- Yeah … sold. I’m in.

[01:11:39] Jasmine: Yeah.

[01:11:40] Nathan: And, you know, I’ve spent well over $10,000 now

[01:11:44] Jasmine: on that offer.

[01:11:44] Oh, amazing. Hey, because I tell her too, I was like, “I gotta get to Boise because I wanna buy this offer.”

[01:11:48] Nathan: Yeah.

[01:11:49] Jasmine: This offer is for the Nathans of the world, and if I can be like a Nathansita, like, you know- … the smaller, less successful Athena version, yeah, I’ll do it. I’ll do it.

[01:11:58] Nathan: Oh, that’s amazing. Well, thank you so much for coming on the show.

[01:12:00] Thank you.

[01:12:01] Jasmine: Thank

[01:12:01] Nathan: you. Where should people go, one, if they wanna check out the offer that you have? Yeah. ‘Cause then there might be people in, in the audience who are like, “Um, I’ll take that 90-day outcome.”

[01:12:08] Jasmine: Nice.

[01:12:08] Nathan: Uh, and then two, if they just wanna follow, you know, everything you’re doing and- And- … they, they want a podcast that they can listen to at 1X and still have to-

[01:12:16] hurry to take notes.

[01:12:17] Jasmine: Well, you can find me @jasminestar, uh, all social platforms, jasminestar.com. But to test out getting a voice message or a video from me, just DM me the word method- Oh … and then we’ll, we’ll get, we’ll get kicked off.

[01:12:28] Nathan: I

[01:12:29] Jasmine: like it. You’ll see it right there. Follow you on Instagram. Yeah. Jasmine Star.

[01:12:31] Jasmine Star.

[01:12:32] Nathan: DM the word method.

[01:12:32] Jasmine: Method. Yep.

[01:12:33] Nathan: Amazing. Thanks

[01:12:34] Jasmine: so much. Thanks, Nathan. Thank you.

[01:12:35] Nathan: If you enjoyed this episode, check out episode 71 with Tiffany Umann. Jasmine built consistent 10K months on the back of coaching, and Tiffany took that same model all the way to seven figures. Check it out if you wanna see how a coaching business can scale beyond the founder doing everything.

[01:12:51] Like the video if you enjoyed it. Hit subscribe on YouTube or wherever you’re listening, and

[01:12:56] I’ll see you next week.

[00:00:00] Ankur: The Teachable exit was about 250 million.

[00:00:02] Nathan: Ankur Nagpal built Teachable and sold it for $250 million. And then he built Carry and sold that for 76 million.

[00:00:09] Ankur: The only reason I was able to sell Carry is because we didn’t raise that much. A very large, very prestigious firm offered us $40 million.

[00:00:18] Nathan: Of funding.

[00:00:19] Ankur: And the worst part is we were tempted.

[00:00:20] Nathan: I built Kit, got a $200 million acquisition offer from Spotify, and turned it down. Ankur raised capital and sold companies. I bootstrapped mine and kept it.

[00:00:31] Ankur: Founders can sell their company and pay zero taxes on 10 to 15 million bucks. To me, it felt like black magic.

[00:00:37] Where it gets crazier now is the 10 to $15 million limit is per shareholder.

[00:00:42] Nathan: I feel like we should not g- keep that information, ’cause it’s

[00:00:45] Ankur: absolutely…

[00:00:45] Nathan: We talk about the bets we make on other people’s companies, and why product market fit is still critically important.

[00:00:51] Ankur: The thing that doesn’t materially become easier is how hard it is to find true product market fit.

[00:00:56] Everyone tells you really nice things, and you have to kind of filter out that .

[00:00:59] Nathan: We took opposite paths. I

[00:01:01] Ankur: think bootstrapping should be higher status. VC means you kind of failed to, like, run a business and grow with profits. The

[00:01:06] Nathan: question is, do either of us regret our decisions?

[00:01:09] Ankur: Nathan, I’ve been doing for 10 years straight, and I hate it, but it works

[00:01:16] Nathan: Ankur, thank you for coming.

[00:01:19] Ankur: Thank you for having me.

[00:01:19] Nathan: I feel like we grew up together in the software world, where as you were building Teachable, you were always, like, 20% ahead of Kit in revenue or somewhere in there. And so when I was like, “Wait, how do you get a better deal on Stripe fees as you pass 10 million ARR?”

[00:01:37] or something like that, you know, Ankur’s who I would turn to. And then we were also both building in the creator economy. We shared a lot of customers, and, um, yeah, learned a lot from each other and all that. But for anyone who doesn’t know, will you share just a little bit of the, the h- the arc of Teachable, um, over the years, and then we’ll dive into more of the conversation.

[00:01:55] Ankur: Absolutely. So, um, I started Teachable back in 2014. What year was ConvertKit?

[00:02:01] Nathan: Uh, 2013.

[00:02:02] Ankur: 2013. So very, very similar timelines. Um, it first started as a platform for literally my buddy and I, where we thought it would be really cool if we had a place where we could teach our own courses without having to go to a marketplace.

[00:02:15] That was the first version of Teachable. Then the creator economy effectively blew up over the next few years, and by the time we reached 2020, right before the pandemic, we were doing about, you know, 25 million in revenue. Our creators were selling hundreds of millions in courses every year. Um, at that point, we received a pretty nice acquisition offer that I took, and I think I spoke to Nathan around it, like, “Hey, we’re gonna do this.”

[00:02:39] And, um, and yeah, we ended up selling the business and then COVID hit. The business basically doubled from 25 to 50 million in revenue in the next three months. Um, but at that point, you know, I was fairly relieved to be out of that business. And, and yeah, I haven’t been super directly involved in the creator economy since, but I’ve gone on to start another business that I’m sure we’ll talk about.

[00:03:00] Nathan: Yeah, so I remember ta- you and I were talking along with another mutual friend, and they said like, “Oh, wow.” Like, you sold at the perfect time as the world was shutting down. And then it was that whole thing, it was like exit at the perfect time, you know, the stock market was down like crazy. And it was like, wait, did you sell at the worst time as it then went up like crazy?

[00:03:19] And ultimately, I mean, you hold meaningful equity in the, uh, in the parent company, so I think you did just fine.

[00:03:24] Ankur: Yeah, totally. And like my general philosophy is I feel like life has been so good to me. I don’t want to be that annoying rich person wishing that things could have gone slightly better. Like, things went pretty fucking well, so I’m fairly happy.

[00:03:39] Nathan: I, I think, I think that’s great. Um, how did you think about- That decision to exit versus keep going, uh, at that stage and, and, like, w- what tipped it over to saying yes?

[00:03:51] Ankur: The short answer is after building a business for almost six years, and I wanna hear your version of this, but I started feeling a bit tired.

[00:03:59] Like, it takes a lot to build a business. Like, you have to push unnaturally hard for many, many years. And we reached an inflection point where I looked at what we had, and I saw our technology, I saw our platform, and to make it dramatically better, like in my mind, if we had to, like, really give it a go, my assessment is we have to rebuild this whole thing from scratch.

[00:04:24] Meanwhile, the business was growing, and we weren’t actively looking to sell, sell the company, but when an offer came in from people who I thought were very smart, very good, very kind, all of which are important, um, it just, you know, found me at the perfect point of being kind of tired. It became basically a no-brainer.

[00:04:42] Curious for your perspective. How, how are you still building this company so many years into it?

[00:04:47] Nathan: Uh, I am, I am a little tired in this moment, but I think that’s because we’ve been building out this space till, like, midnight or 1:00 AM the last, like, four or five days. Part of the reason that I wanted to talk is that we have very different approaches, right?

[00:04:59] You know, despite building for similar amounts of time, I’m on company number one, you’ve exited company number two, you’re now running a fund, you’re now doing other things.

[00:05:09] Ankur: I, I think I’ve tried at least twice to see if you’re interested in selling, representing different parties. And not, not in recently, but back in the…

[00:05:15] And you’re always like, “I think I may do this forever.”

[00:05:18] Nathan: Yeah. And th- what I … The way that I’ve thought about it over time is build a business to sell it, so it has all of the things that investors really want, so recurring revenue, high gross margin, uh, a durable customer base that’s spread across a lot of different, um, users and all of that, and then don’t sell the business.

[00:05:39] ‘Cause turns out, uh, I believe that a business that is really good to sell is probably also really good to own and operate. Um-

[00:05:45] Ankur: There’s a, there’s a really great quote I love. It’s, like, “Build your business like you’re going to own it forever, otherwise you might just have to.” And I think that’s I think that’s, that’s sort of testament to how you’re thinking about it.

[00:06:00] Nathan: Yeah, and I, I’ve- I feel very lucky that the customer base that we have is one that I, like, am deeply in love with. Uh, this, this, uh, stage that we’re on is actually a bookcase. Uh, in true New York City fashion, it’s, um, used for all kinds of things. It folds down, uh, to turn into a stage for events and folds back up.

[00:06:20] Uh, but it’s our, our, um, New York Times bestselling authors who are on Kit, and there’s, I don’t know, 25 or 30 of them or something that we had showcased, uh, on here last night. And, you know, I just feel really, really lucky that we get to serve those customers. So I plan to run this business for a very long time.

[00:06:37] Uh, I always tell the team 10, 10 years, and they’re like: “Wait, didn’t you say 10 years, like, five years ago?” And I was like: “Oh, no, it’s a rolling 10 years.” But I think the, the biggest thing that’s made that difference is having both a business model that endures, like recurring revenue is amazing, um, but then also having a customer base that we really care about.

[00:06:57] And, like, I would spend all of my time with creators and, and love every minute of it. Um, so yeah, my… I- I fully expect to be… We’ll do some event and you’ll be like: “Oh, yeah, I sold company number six.” And I’ll be like: “I, I still have company number one.” I don’t know if you have any thoughts or commentary as, as we’ve, uh- You know, had these conversations over the years, but-

[00:07:16] Ankur: No, I mean, look, I, I respect and admire that.

[00:07:20] Like, I think, I think there are some people who sort of build one business and see it as their life’s work, and I think that’s incredibly admirable. Every time I’ve started a company, the idea has always been build it, you know, without, without aiming to sell. Like, I think if you start a company with the goal that you’re going to sell it…

[00:07:39] And sometimes I get concerned. Like, I’ll go speak to a group of founders, and everyone who hasn’t even started their company wants to know about the exit. Like,

[00:07:45] Nathan: what’s- What are the multiples? How do you feel about the market in this? It’s like you haven’t provided- Yeah … any value to anyone. Companies are just, it’s just a value exchange, and spend all of your time on how do you create value and not, you know, what could my possible exit be?

[00:07:58] Ankur: Totally, totally. But at, at every point I’ve- I have an open mind where I’m building the business. And I think as a founder you’re always willing to sort of hear what your business may be worth. And at any given point there’s, like, some kind of expected value math in your head, um, not just on what is the financially best outcome, but what is the best outcome for every single stakeholder, which means every single investor, every single employee, past and present, every single customer.

[00:08:28] And then your job as the founder is to try to find the equilibrium point across all of that.

[00:08:34] Nathan: That makes sense. Okay, let’s talk about Carry. So you just sold Carry, is it a month ago? Yeah. It’s quite

[00:08:39] Ankur: recent. Uh, well, the deal was signed about two months ago, and will hopefully close in two days, so.

[00:08:45] Nathan: Okay. And then actually, I think you can say some of the numbers on there of the, uh, the Teachable exit was around 200 million?

[00:08:53] Ankur: The Teachable exit was about, we were doing about 25 million in revenue, and it was a 10X, so about 250 million.

[00:08:59] Nathan: Okay.

[00:08:59] Ankur: The Carry business we were at about 4 million in annualized revenue, and, uh, all in the exit was about 75, $76

[00:09:09] Nathan: million. Okay. And then, um, that’s a fantastic multiple.

[00:09:12] Ankur: It is a fantastic multiple, but again, I think different types of acquirers pay for different things, and we’ll get into that.

[00:09:18] But with the Carry business it was, you know, acquired for different reasons than sort of- Right … pure multiple on revenue.

[00:09:24] Nathan: Yeah, um, so, you know, what is Carry as a business, and, um, like where were you planning to take it?

[00:09:30] Ankur: So the, the vision behind Carry has always been that while I sold Teachable, um… As a little bit of background, I’m a first-generation immigrant here.

[00:09:40] I did not grow up in America. I moved here for college. I know nothing about the US financial system. And while selling Teachable I, you know, talked to lawyers and accountants before structuring the sale, and it blew my mind to learn about the sort of- Well, I mean, to me it felt like black magic in the US tax code, uh, where by talking to the right accountant, I was able to save many, many millions of dollars by learning about things like the QSBS tax break and all of these different things.

[00:10:09] Um, the vision behind Carry always was there’s so much cool stuff in the tax code. There’s no good way to productize it to the average person. Um, so Carry was a platform to do that for business owners. The first and primary product we had was a one-person 401. So for anyone who’s self-employed, typically your employer provides your 401, which again is a quirk or nuance of the US tax system.

[00:10:33] But if you’re self-employed, no one does that, and that was our primary product.

[00:10:36] Nathan: That was my experience as well, where as you learn these tax things over time, you talk to your, uh, CPA that you hire and you’re like, “Anything else I should do?” And they’re like, “Yeah, no, you’ve, you’ve pretty much covered it.”

[00:10:44] They’re like, “You’ve… You’re dialed in.” And you’re like, and then you go talk to a founder friend and you learn about QSBS or QSBS stacking or some of these other things, and Then you go back to your accountant and like, “What about this?” And like, “Oh yeah, no, you could totally do that.” And you’re like, “What?

[00:10:58] You have one job, and you did not do that job.” For any- Do you wanna give a, a quick explanation of QSBS for, uh- Yeah … ’cause I feel like we should not get- Yeah … keep that information ’cause it’s,

[00:11:08] Ankur: it’s- Absolutely. It’s quite- So QSBS is something, uh, that blew my mind, and I only found out about it about, uh, two months before selling my first business.

[00:11:16] But the way QSBS works is if you are a startup founder, which is typically the founder of a C corp. So as a creator, most creators aren’t set up to be a C corp. Um, you probably shouldn’t, since there’s downsides of being a C corp, like double taxation, but if you are raising venture money or you want to go public someday, you likely are going to be a C corp.

[00:11:36] I’m guessing you started as an LLC and then converted? Yep,

[00:11:38] Nathan: and then we converted.

[00:11:39] Ankur: Yep, exactly. So the way this works is if you hold shares in, in this C corp for five years and you sell your business, you pay no taxes on up to $10 million. Uh, last year there’s a new rule change that changes it to $15 million.

[00:11:53] Um, so that means founders can sell their company and pay zero taxes on 10 to 15 million bucks, which is, one, super crazy. Where it gets crazier now is the 10 to $15 million limit is per shareholder, so you can actually multiply it. I can give shares to my family members, to my mom, to my dad, like people can do it to their kids.

[00:12:14] Now as a family, you multiply that from 15 to 30, 45, $60 million. Um, it’s actually remarkable because people think of how high taxes are in America, and there’s tax breaks like this for business owners that a lot of people don’t know about.

[00:12:29] Nathan: And there’s even layers beyond this of like if you convert from an LLC to a C corp later, it’s 10 times the basis and, and there’s all kinds of other rules within that.

[00:12:37] But it, it just points to how important a business like Carry is because it’s explaining these things and making it accessible when really you, otherwise you, you have to be an insider or someone has to tell you, you know, like other founders or something like that, to then know that this exists to be able to, to implement it.

[00:12:54] Okay. So with Carry, what were the, what were the things that Carry was acquired for, uh, versus what Teachable was acquired for?

[00:13:01] Ankur: Yeah, absolutely. So with Carry, we were at about 4 million in ARR about three and a half years in, and our path was decent. Like it, you know, it was… The way I think about it is it’s probably similar to a lot of the early Teachable and ConvertKit growth where we were doubling year on year, which is, you know, 100% year on year growth.

[00:13:23] But given everything happening in the world today, it wasn’t a growth rate that was satisfactory to me. I wanted us to be growing faster. Um, what I felt is we found product market fit in this, like, pretty small niche, and this would keep growing, it would keep compounding, but the path to hitting 100 million in revenue was still, like, 10 years out or some amount of time where I felt like the time it would take to build a massive business from this, um, was too long for my amount of patience.

[00:13:54] Um, as this was happening, I was being recruited by AngelList to run their new public venture fund, USVC, which to me sounded like the coolest opportunity in the world. Um, it’s a fully public venture fund where I could tap into all the content and marketing I had been doing while, you know, running a portfolio, opening up access to private markets for, like, every person.

[00:14:16] It also had some form of regulatory arbitrage, or not arbitrage, regul- regulatory work that has gone into it because Prior to this type of structure, only accredited investors could invest in startups. So this seemed like a very good opportunity. Um, however, every time we had a conversation, I, I told the AngelList team that I had certain obligations to all the stakeholders I mentioned, to my team, to my cap table, to myself, to actually find a good outcome for the Carry business.

[00:14:49] Um, and after a lot of negotiation, this whole thing was structured as a acquisition that was at least in part to have me come on and run this venture fund moving forward. And as a result, the multiple is, you know, far more generous than someone buying it for revenue.

[00:15:05] Nathan: Yeah, that makes sense. Uh, that, and I was very curious about to what extent the technology was acquired, the, um, you know, some of the…

[00:15:12] If AngelList wa- wants to run that across a much bigger portfolio, or if it was really about the team or whatever else.

[00:15:17] Ankur: So, so here’s where it gets a little crazy. So AngelList said they wanna buy us. After a lot of negotiation, we got up to 70 million across cash, equity, earn out, a lot of that. But then it turns out they didn’t actually care about the entire platform underneath.

[00:15:34] So I basically negotiated for the ability to take the underlying platform and sell that to a second buyer. So we took that, and then we found a second buyer for the Solo 401k platform. Um, but all of that, right, that 4 million bucks in revenue only was able to get 6 million in a sort of very simple all cash asset deal.

[00:15:56] So that kinda shows you, like, multiples and how bad they can be when you have to sell a business versus when someone is coming to you to buy a business. It’s a completely different game.

[00:16:06] Nathan: Yeah. Okay, so talk about that, ’cause that’s an important distinction of, uh, businesses being bought versus being sold.

[00:16:11] Ankur: So the core Carry business, which was being bought in a way that it was opportunistic, we were able to sell for $70 million. Then what’s left, which is, you know, the u- underlying asset that was generating 4 million a year that we had to sell. You know, I had to get rid of this thing, and I wanted to find a good partner.

[00:16:29] We were only able to sell that for 6 million. So you see the difference, right? 70 million for basically talent and, like, the promise for what could be, and 6 million for the actual asset.

[00:16:40] Nathan: Yeah, that’s a huge difference. Okay, let’s talk about another difference in how you and I operate, um, r- in fundraising versus, uh, staying bootstrapped.

[00:16:50] And we actually, we’ve done some secondary transactions, and so we can get into the, the pros and cons of that. But yeah, how do you think about raising? ‘Cause you raised for Carry. You, you could have self-funded that from there. What was the reason that, uh, you raised money for Carry specifically instead of purely self-funding?

[00:17:06] Ankur: There were a couple of reasons. Um, one big one is fintech is fairly expensive. Like, as, as we would’ve kept building it out, there was a high cost of compliance. Could I have funded it fully from my balance sheet? Probably, but it would start getting a bit irrational- Right … where I now have, you know, a lot of my money in this company when I already believe my time is my most valuable asset, and I’m investing that in the business.

[00:17:32] Um, so that’s why I did raise venture funding. However, that’s also relevant because when you raise venture funding, you have… You effectively sign in, in my mind, an implicit promise that you’re going to, like, go for broke. You’re going to try and grow really, really fast. You’re not gonna pay yourself a lot of money.

[00:17:53] You’re not gonna be wildly profitable and kind of chill. You’re going to live a pretty hard life for the goal of trying to make this worth billions of dollars. Um, and I think that decision is related to why I felt like we weren’t growing fast enough. Had this been a business that I fully owned, 100% growth is fine.

[00:18:12] You know? I can take my time. But because we raised venture capital and I signed that implicit promise, I had to free myself, or at least felt like I had to free myself of that implicit promise in order to, like, you know, be able to do what I wanna do.

[00:18:25] Nathan: Yeah, and I think that’s… You have a lot of flexibility when you either stay self-funded or you set the expectations of, like, this is the style of business that, that you’re building.

[00:18:36] Totally.

[00:18:36] Ankur: Totally, and I, I always tell founders, ’cause sometimes founders don’t realize that’s what they’re doing when they’re raising venture capital, because VC for whatever reason is seen as higher status. I think it shouldn’t be. I think bootstrapping should be higher status. I think VC means you kind of failed to, like, run a business and grow with profits.

[00:18:54] But because of VC seen as higher status, you s- now see so many people, um, who don’t know better raising venture capital, and then getting, you know, sort of trapped where they have businesses doing millions of dollars a year, but maybe it’s growing 50 to 70% being profitable. A really good business, but a lot of great founders feel super trapped because of the way they’ve raised money for it.

[00:19:17] Nathan: Every time in decision-making that I’ve felt unsure of when I’m trying to decide between A and B, well, I have some family members who, uh, optimize for what’s the best story. Like, what’s the most entertaining outcome?

[00:19:27] Ankur: Do it for the lore.

[00:19:28] Nathan: Do it for the lore. That’s one way to do it. Um, something that I’ve always thought of is what preserves optionality.

[00:19:34] Like, people think like, oh, you decided to raise funding or you decided to stay bootstrapped, and that was a moment in time decision. It’s like, well, no, actually, you can, you can cross… It’s very easy to w- relatively between the market and a bunch of us to go from bootstrapped to venture-backed, assuming you have traction and all of that.

[00:19:53] And so at any point, you know, if you stay bootstrapped, you’re, you’re preserving this optionality. Now, if you then don’t If you’re not able to grow, then you lose that optionality pretty quickly ’cause no one wants to fund a, a flat business. But then once you go to the, to the other side and you raise funding, it’s very hard to go back.

[00:20:08] Now, there are companies, uh, you think about Zapier, um, you know, people… They’re a venture-backed business. I think they raised a couple million to get to a few hundred million in revenue . So it’s like-

[00:20:20] Ankur: And then they raised a few hundred million.

[00:20:21] Nathan: And then they raised a few hundred million. Yeah.

[00:20:23] Ankur: E- even Hotmart was very similar.

[00:20:25] They raised 400K, and then 10 years later they raised 100 million. Yeah. Like it’s… I, I will say if you are raising money too, within the spectrum of raising money, how much you raise is very important. The only reason I was able to sell Carry in this kind of deal and everyone still did somewhat well is because we didn’t raise that much, and it almost was in that way.

[00:20:47] There was a time when we were doing about 300K in ARR, a very large, very prestigious firm offered us $40 million Ah, we were looking to raise, like, five.

[00:20:58] Nathan: Right.

[00:20:58] Ankur: And the worst part is we were tempted. We thought about it pretty hard. And just to be

[00:21:01] Nathan: clear, that, that was $40 million, uh- Of

[00:21:03] Ankur: funding …

[00:21:03] Nathan: of funding

[00:21:04] Ankur: at- They wanted a third of the company.

[00:21:06] They wanted to… It was a big, big growth fund. They wanted to deploy a lot of capital.

[00:21:09] Nathan: Right.

[00:21:10] Ankur: And we were tempted. I thought about it. I talked to the team. The team honestly was more for it, but I ultimately decided against it for two reasons. One is it makes an entire spectrum of, like, okay outcomes bad.

[00:21:25] Like, I wouldn’t… Like, this deal would not have happened. And two, I just didn’t trust we wouldn’t do dumb shit with it. Like, we probably would’ve, you know, made stupid decisions. Right. Um, but that makes a big difference because, again, we sold this business at 76. The reason 76 was psychologically important, you may be like, “Why aren’t you saying 75?”

[00:21:43] It’s because 75 was the valuation of our last round, so we wanted to at least nominally clear it for it to feel like a sm- at least a small win, even if nominal for everyone involved.

[00:21:54] Nathan: Right. Yeah, that makes sense. And especially in, in a lot of these, um, a lot of these different markets, this happened a lot in 2021, where people raised amounts of funding that limited their options in a huge way, and, and the, the idea was that more funding is always better, and it’s just, it’s not the case.

[00:22:14] So I have a huge amount of respect when I see founders who you know in a hot market can, can raise a ton of money, and then you see them do these very strategic rounds where they’re like, “Oh, I actually only need $2 million or $6 million to get to the next stage.”

[00:22:28] Ankur: Yep. A lot of people don’t know that almost every time you raise venture capital, you have to pay it off before anyone sees a dollar.

[00:22:36] So there’s a lot of companies now that have raised $200, $300 million. If they sell for less than that, like, unless the deal is restructured, no one makes anything. Investors always get their money back- Yeah … before anyone sees anything. Yeah. So large rounds can really, really change, uh, the math when you exit your business.

[00:22:54] Nathan: Yeah. Okay, so since you’ve built two businesses, you have the advantage of, uh, being able to start from scratch on round two. What are some of the biggest things that you did differently in round two versus round one of building the company?

[00:23:06] Ankur: It’s funny, ’cause round one overall went better, so I don’t know how, how useful, useful the lessons are.

[00:23:12] Um, but round… With round two, we were able to Hire good people much faster. A lot of the things that first-time founders really struggle with or spend a lot of time on become very easy as a second-time founder. Like fundraising is very easy, hiring people is very easy. Um, all these things become much easier.

[00:23:35] The thing that doesn’t materially become easier is how hard it is to find true product market fit. If anything, it’s… You almost have to filter out the bullshit because if people think you’re a founder that’s been successful before, they will be nicer to you than they otherwise would. So everyone tells you really nice things, and you have to kind of filter out that bullshit.

[00:23:55] Um, yeah, there’s a really nice, good quote I liked where I’m like The best way to play being a second-time founder is if you can use the hype to your advantage without believing it yourself. Um, because you will be more hyped up, yet the hard things continue to remain the hard things.

[00:24:13] Nathan: Yeah, and you feel like you should be making progress faster because you’ve learned all these other skills, and, and maybe you will.

[00:24:19] Like, fundraising might go faster, um, the first few customers and all that. But product market fit might not go faster at all, and it might even take longer if people are lying to you, like, “Oh, Ankur, like, great idea. I cannot wait to do this.” And you’re like, “Great. Will you pay for it?” They’re like, “Well, I don’t know.”

[00:24:34] Ankur: And, and I… And at some level, you, you and other people put more pressure on you. Like, everyone who joined the team joined the team because they’re like, “Okay, this guy succeeded with his last company. This is my, like, ticket to success as well.” And yeah, and then the first time, everyone almost expects you to fail.

[00:24:55] The second time, you’re expected to succeed in a way that you’re like, okay, like, you know, I’ve been on panels talking about building a successful company. It’s kind of embarrassing if this goes poorly after telling other people what they should be doing. So yeah, there are, you know, pros and cons.

[00:25:08] Nathan: Yeah, is there anything now as you look back over two companies and two exits where you’re like, okay, if I were doing round three, uh, and it was a, it was a company rather than a fund, uh, that you’d focus on or that you would do differently?

[00:25:20] Ankur: So I generally believe in order to get good at something, you need so many repetitions, and like an N of two, N of three is still not that many where you generalize. But one of the things I think I would think long and hard on is, again, like, how you fund the business affects so much of the strategy. So pretty early on, make a very clear line of like how big do I want this business to make and accordingly fund it.

[00:25:50] Like, with Carry, it was sort of in between, um, versus like, okay, if you have something that is and can truly, truly be venture scale, go and actually build that or fully retain optionality.

[00:26:02] Nathan: Okay. That makes sense. I wanna go to questions from all of you who have joined us in just a second. Um, but before we do that, I’m…

[00:26:09] So think about the question that you wanna ask. Uh, Daniel on our team is gonna have, uh, a mic to pass around. As you think about going into running a fund from here, like that’s a… You’ve done a lot of angel investing, so you’re familiar with that side. But what are the, like, the biggest skills you think you have to learn, you know, the, um, and ways you need to level up individually to, like, tackle this next stage?

[00:26:30] Ankur: So in between Teachable and Carry, I ran couple of venture funds, so I have a lit- little bit of experience there. What drew me to this role at USVC is It’s running a fund, but we’re kind of building the whole thing, ’cause it’s a public venture fund. It’s a very different type of product. Like, there’s a whole product aspect to it as well.

[00:26:51] Um, the challenges with it are it’s, you know, it’s a very, very hot time to invest in private companies, and-

[00:26:59] Nathan: Okay, let’s talk about that for a second. Um, I think that HubSpot at this moment has, like, a three times ARR multiple, maybe, maybe less.

[00:27:07] Ankur: Uh- That SpaceX is going public at 2 trillion with, like- … tens of billions in revenue.

[00:27:12] Nathan: Yeah.

[00:27:12] Ankur: Um-

[00:27:13] Nathan: Shopify put up, like, an insane Q1, and the whole market’s like, “Eh, I don’t know. We don’t care.”

[00:27:18] Ankur: Yeah. It’s, it’s definitely… Running a, you know, running a public venture fund now, these are things that are quite important and quite significant to us. But the way we’re doing this is we’re not simply making this a vehicle to index the later stage names.

[00:27:32] Like, there’s… Like, if you pay attention to private markets, there’s so much capital now in OpenAI, Anthropic, SpaceX. We’re taking a longer term strategy where because we provide liquidity every quarter, we will have some exposure there, but also investing in the early stage fund managers and, and things that will pay off, you know, one, three, five, seven years in the future.

[00:27:54] Um, the general thesis we have is- Every single year, more new companies will be started that will be more valuable than all the companies started before. And building our fund with a, with a way that, you know, if you believe that thesis, this is a vehicle to bet on that.

[00:28:10] Nathan: Yeah, that makes sense. Okay, was there anything that you’re like, “Ooh, I’m gonna have to figure out this part in particular,” or it’s gonna be, be difficult to

[00:28:17] Ankur: implement?

[00:28:17] The, uh, the part that, the part that we’re still figuring out is it’s … There’s a lot of ways I can get myself, get myself into trouble from a regulatory perspective that I’m discovering, since this is now a public security. Right. And yeah, I, I’m gonna try my best not accidentally go to jail. I think that’s probably a good, good priority.

[00:28:34] Audience member: That seems like a good goal. Yeah.

[00:28:36] Nathan: All right, who has a question they wanna kick us off

[00:28:38] Audience member: with? Thanks, guys. That was awesome. Um, Ankur, this is for you. So you mentioned it was way easier on your second company to recruit people, to hire great people. I think that’s the core to any business, is the team. What was most effective in pitching them to come over?

[00:28:53] Because it’s a combination of vision, incentives, you as their boss. Like, what, what did you find was kind of most effective to attract great talent?

[00:29:01] Ankur: I think there’s two dimensions that helped a lot. One was top of funnel. Um, having an audience was very, very helpful. I was able, I don’t know, I tweeted I’m starting a new company, and there were, you know, almost a million impressions on that.

[00:29:14] You know, tons and tons of DMs. And so top of funnel became substantially easier. I went to a bunch of people and I, you know, told them, “Who’s the best person you know for this?” And then when it came down to closing them as well, the strategy we picked is like early on, pick a strong founding team, um, and be f- very generous with equity to the first, like, five or seven people, um, in a way that I didn’t, did not when I started the company.

[00:29:40] I did not have a co-founder that had an equal amount of equity as I did. As a result, I could be very generous with the first five people. Um, so the combination of both those things made early hiring, you know, substantially easier than the first time around. Um, and even then, every time we did have a role, hiring only got hard when we needed, like, specialists when we were further along.

[00:30:02] Like a head of engineering is still hard when you’re, you know, two, three, four years in, but the entire founding team hiring was, was quite easy.

[00:30:08] Nathan: Recruiting is so, so important. A couple things that worked well for us, um, being a distributed team made it easier, and I know there’s so many benefits to being in person in one office.

[00:30:19] We’ve talked about that as a c- as a Kit team. Like, oh, if the Kit exec team was all in one room, you know? And it’s like, okay, well, who’s moving? ‘Cause we’re in New York and Charleston and Boise and like, um, you know, all over. So but being a remote team, you can pull from, uh, so many places. Exactly as you said, like having a personal brand or a reputation, um, is so important.

[00:30:40] It, it helps so much. Like if that’s going to be- We can debate how useful it is at a small scale for acquiring customers, but it’s very useful for acquiring talent. Even if it just gives people an opportunity to say like, “Oh, um, who is this person that I’m about to interview with?” Or, “I’m thinking about taking this job.

[00:30:57] Let me go scroll through their LinkedIn posts and all of that, and see the content and get a feel for who they are, and who they’ve been over the last, like, three to five years.” This is someone who’s shown up consistently online for a while. Another thing that, that really helps is in direct outreach, the thing that I do, is I go to everyone that I would want to work on my team and I say, “Hey, here’s the, here’s the job that I put together.

[00:31:18] I wrote it up. Um, do you know anyone who would be a great fit for this?” ‘Cause there’s some people where, like, they’re doing such important or prestigious work or whatever that you don’t… You know, and your company is so small that, uh, you’re kinda awkward about like, “Do you want this job?” And they’re like, “No, it pays a quarter of what…”

[00:31:36] You know, like, that there’s an interaction there that could be awkward. But if you say, “Hey, I think of you as a legend in this space. You must know other people like you. Who, um, who would be a great fit for this?” And they’ll often say, like, “Oh, let me think about it.” And then some, you know… So say 70% says, “I’ll think about it and let you know.”

[00:31:52] 20% or 30 or, you know, 28% say, uh, “Oh yeah, here’s someone that would be a good fit.” And then a small fraction go Actually, I’d be interested in that. And it’s such a great lead-in to the conversation without any of that, uh, that awkwardness.

[00:32:07] Ankur: A great way of doing this also is to appeal to people’s ego, right?

[00:32:10] Just post who’s the best person you know at growing a YouTube channel, and now you’ll start seeing people nominate themselves- They can nominate themselves. … other people nominate. Yeah. And then now you have a list of prospects that you can go reach out to.

[00:32:21] Nathan: Yeah, it would be crowdsour- crowdsourcing and playing to ego is a good one.

[00:32:24] Yeah.

[00:32:24] Audience member: I’m curious to hear for, from both of you on this question. What are some contrarian beliefs or, like, hot takes that you hold that helped you get to where you are?

[00:32:34] Nathan: I’ll go with one. Um, I pay people the same amount globally, uh, independent of where they live or their local cost of living. And so we have team members who we’ve hired in Poland and other places who have shaped the entire company and are thrilled because they make…

[00:32:54] Like w- someone told me that when he, when he joined Kit, he tripled his salary, and he makes even more than that now. And he has shaped our entire product in a massive way. And so we have a globally distributed team. We hire from everywhere, and we don’t get any of the economic advantages of doing that. Um-

[00:33:11] Ankur: That sounds like it’ll be hard to recruit people from New York and San Francisco then.

[00:33:14] Nathan: Um, I mean, I have… What do I have? 11 people in New York.

[00:33:18] Ankur: Okay.

[00:33:18] Nathan: Um, and a decent number. We, we pay-

[00:33:20] Ankur: So yeah, you basically- We pay quite a- … pay New York salaries to everyone.

[00:33:23] Nathan: Yeah. And, and it is hard, right? Yeah. Um, to some extent, but we have, uh, we have team members who go above and beyond in a massive way because the- they’re so thrilled to be a part of the team.

[00:33:35] Um, I would- wouldn’t necessarily recommend it for everyone. It’s just a personal philosophy that I have. It’s a contrarian take, and, uh, it’s paid off very well for me. What’s one of yours?

[00:33:43] Ankur: Don’t talk to or listen to your friends when starting a company. Um, I find friend feedback to be anywhere from useless to actively damaging They’re going to be nice to you.

[00:33:56] They typically don’t really have an understanding of, of how hard things are. They’ll say all the positive things. I also think when you’re starting something, like, just doing shit is a better way of going about it. Um, build something, send a link, see if someone buys. That kind of activity is much better at testing an idea.

[00:34:14] What I’ve seen a lot of people doing is they’ll go grab coffee. They’ll, they’ll sit down with 5 people, 10 people, 20 people, and this is bad because, one, you don’t get useful feedback. Two, it feels like work. Because it feels like work, you’ll do more and more of it, and you’ll be like, “Wow, I’ve spent a month kind of working on my idea,” but you actually haven’t done much.

[00:34:32] So I tend to think it’s better to just work on things, try things, and see what happens.

[00:34:37] Nathan: Yeah, it’s, uh, it’s performative, uh, work, and it’s just performative to yourself. It’s, it’s really not, not helpful. Uh, we’ll go to another question and I’ll think of more hot takes ’cause this could be a good segment that we do.

[00:34:47] We’ll go here and then, uh, up to the front after that.

[00:34:49] Audience member: Great talk, guys. Well done. Um, I was gonna ask, what are you seeing working well for some GTM strategies? So what are you seeing that’s probably not working anymore over the last 10 years? What’s working now?

[00:34:59] Nathan: Okay, you g- got me onto a hot take. My least favorite startup and business advice is, especially, and this is the worst because it sounds smart and it’s not.

[00:35:09] What got you here won’t get you there. And people say that because they, they do these things. They’re like, “Okay, when we got our first 10 customers, now we need to do something different,” and, and on from there. Um, ’cause the, the… this advice is both true and false simultaneously. Like, it’s true 50% of the time and it’s wrong 50% of the time, which means it’s useless ’cause you don’t know which half.

[00:35:29] So something that works really well still, I believe, in go to market is direct sales And that’s something, you know, that’s basically how Kay got our first, uh, 20,000 ARR for sure. The, uh, uh, sorry, 20,000 MRR that then scaled into 100,000 and beyond, and then we stopped doing it because, like, oh, no, we’re a grown-up company and we do scalable important things.

[00:35:52] And we should’ve kept doing that all the way along because turns out direct sales gets easier. You have brand reputation. You can name-drop your customers. The, the trust comes. You know, like, you can build network effects. You can systematize your outreach and your closing funnels and y- you know, all of this stuff.

[00:36:06] Ankur: Are you still doing webinars, Nathan? I’ve been doing webinars for 10 years straight, and I fucking hate it. But it works.

[00:36:12] Nathan: Um, I am no longer teaching the webinars. Uh, but yeah, we’re, we do, you know, two to four a week. Um, so that was another one for us that we stopped doing webinars because we’re like, oh, we’re onto the next thing.

[00:36:22] Like, uh, grown-up companies should, you know, do paid acq- acquisition funnels or, you know, that sort of thing. Often what got you here done better is gonna be the thing to get you there. And now my approach is very much around what’s the flywheel that I can build where I can do the same thing over and over again, systematize it, and make it 1% better in each iteration, um, and, and go from there.

[00:36:44] So as far as what I’m seeing work really well in go-to-market, direct sales still works. You know, go recruit top customers. Your sights move higher up. You know, years ago I was reaching out to, um, individual creators or Pat Flynn or, you know, people on that scale, and now our direct outreach is turning into people like Tom Brady and Emma Grede and, um, you know, on a different scale ’cause that’s just where we’re playing now.

[00:37:08] Um-

[00:37:08] Ankur: How do you direct outreach to Tom Brady?

[00:37:10] Nathan: You figure out who the right… So it, it’s the right-hand man principle You figure out who are the behind the scenes people that actually call the shots. Everyone’s trying to get like, “Oh, if I could just get three seconds of time of the right person, how do I position my…”

[00:37:23] And it’s like, what are you doing? They’re not the decision maker. They don’t, they don’t care. And so this would be a good example of, um, how we got Tim Ferriss on the platform years ago, it’s probably 2017, is I figured out, okay, who actually calls all the shots behind the scenes? Who’s the producer of the podcast?

[00:37:36] Who’s running the brand and all of that? Where do they live? Who can introdu- introduce me to them? Turns out getting the introduction to the person whose job it is to look at opportunities and filter through them, like it’s way easier to get in front of them because the last thing they want is the person they work for, um, coming to them later and be like, “Wait, you had this opportunity and you didn’t show it to me?”

[00:37:54] You know? So they’re gonna look intently like, is this something we should look at? Uh, and then go meet them in person. Um, I’ve had a bunch of times in my life where people have said like, “Hey, if you’re ever in New York, like yeah, let’s meet up.” And I was, “Great, if I’m ever in New York or in Boulder or wherever, you know, I’ll, I’ll do that.”

[00:38:08] And it’s like, no, no, no, that is the reason. You’re like, “Oh, funny enough, I’m gonna be in Boulder next week.” You know? And they… How is Monday at 4:00 sound? You know? Or, um, that kind of thing. That,

[00:38:18] Ankur: that’s exactly how we signed Pat Flynn to our platform. I, I told Pat I would be at trying to… One of the podcast conferences or something, and as soon as he replied, I booked my ticket and flew in- Yeah

[00:38:29] just for that meeting. And yeah, then he signed up and became an advisor and our biggest affiliate.

[00:38:34] Nathan: There’s an interesting filter on this kind of thing where cold outreach that’s an e- like an email, especially now, it’s even easier to send decent cold outreach, AI written at scale, right? And so our filters are higher.

[00:38:46] But if you say something like, “Hey, I’m gonna be at this event, um, you know, before or after your talk, I’d love to grab 20 minutes to ca- to catch up”, or you know, that type of thing ends up working really well, but you don’t actually have to already have the ticket to the event or already be going. You can line up the meetings, and if they’re not good enough, you’re like, “Oh, shoot, I, I couldn’t, couldn’t make it.”

[00:39:07] Or if you get the meetings, then you’re like, “Great, I’m going.” Um, so yeah, uh, I love the, the unscalable things that then you can systematize and do over and over again for go-to-market. What are you seeing works in go-to-market?

[00:39:18] Ankur: It’s crazy to me this still wor- this works because it’s the most obvious thing.

[00:39:22] Nathan: What a, what a hook. Uh.

[00:39:24] Ankur: I’ve been, I’ve been creating content too long. But I’ve, I’ve had really good success. I turned this off about a month ago, but before that, I had very good success with full AI content creation on channels I didn’t care about. So Twitter I care a lot about. I don’t want Claude writing, writing it for me.

[00:39:43] LinkedIn and Threads I don’t really care about that much. So I trained it, gave it keys to the kingdom, and you would think, you would think it would just be a bunch of slop, but it actually for both platforms gave me my best month ever as long as it was like, one, correctly trained, um, which meant giving it a lot of training on stuff I had actually done, things that worked, and then creating some kind of reinforcement loop where it stored every post and the performance.

[00:40:10] It would look at it, evaluate what worked, and kind of rewrite it. Um, I turned both of those on and it still works, and a lot of the accounts that are doing it well, you don’t even realize it. But a lot of this is automated. Um, the one caveat is you have to be o- like, some weird shit happened and I had to be okay with it.

[00:40:28] Like, it posted on my LinkedIn saying, “Life growing up in India.” I did not grow up in India. This was, this was, this was… Yeah. Uh, but it also replied to a bunch of people on LinkedIn saying shit I wouldn’t have. So there were small downsides. So I wouldn’t, I wouldn’t use it on platforms I care a lot about, but if your idea is you wanna grow and you don’t mind being a bit cringe or whatever, um, the right training still works, and I think there’s probably a brief window of time before we’re fully flooded with it, but I’m sup- I, I thought it already wouldn’t work.

[00:40:58] Nathan: And so if you were to execute on that, it’s giving it the library of content, either the huge back catalog that, that you have over time, um, or You could do like full context dumps in- into it where you could potentially for, you know, every day for three weeks straight, you could be recording voice memos on a walk, you know, as you’re walking the streets of New York or walking to the gym or whatever, dump that in there, and then- Yep

[00:41:23] it would feed off that.

[00:41:24] Ankur: The two things that made it work that wouldn’t otherwise are, one, like the fact that it could kind of learn how I wrote. Because otherwise you, you know, it, it reads like the standard AI sloppy read, but that’s only because you haven’t taught it how you write. Um, and the second thing is like just breaking down the anatomy of like what makes the post work.

[00:41:43] Like, oh, this is a hook. This is like a call to action, and kind of either saving that as a skill or something.

[00:41:49] Nathan: Yep. Um, and if you specifically have it brainstorm a bunch of different hooks off of an idea you give it, and you, you can select one and, and that makes a big difference. But especially don’t say like, “Write this entire thing.”

[00:42:02] If you say, “Write 10 hooks for this,” have it flow into this other one. The thing I would say is, um, there’s a markdown file, uh, called Tropes. I think it’s at tropes.fyi, and if you go download… It’s just all the common AI writing tropes that we all see and hate. And, uh, you can load that into your project, and then in any writing it’ll be like, oh, let’s not do the It’s not this but that, you know, or those common things

[00:42:26] Ankur: Also, it’s kind of bad, but repetition works.

[00:42:28] Like, if you have something that really works well, you can chop it up in different pieces for the rest of your life. I mean, again, I, I love Justin Walsh, but you read his content, it’s like, uh, he… The same thing dissected down slightly differently over and over, um, and you can apply that to anything.

[00:42:45] Audience member: Yep.

[00:42:45] Nathan: Okay, who’s got the next question?

[00:42:47] Audience member: I want to ask you, uh, knowing that, uh, when you build something in the morning, that, uh, the AI is evaluating so fast that the afternoon what you built has already been passed, and knowing that the VO is there, Lovable, Grok build, whatever the systems are available right now to build.

[00:43:06] So I wanted to have your point of view as investor, how you’re able to manage now, uh, the way that you’re going to invest in a company, knowing that it’s pretty easy to build something now on the side of the software.

[00:43:19] Ankur: To me, that’s a good thing because now we should be able to build dramatically better and more delightful things, right?

[00:43:27] Like, if all you’re building is, like, form entry or whatever, sure. But because we now have AI, I think there’s an opportunity to build, like, insane things that just could not be built before. Uh, but I do think, again, if you are going the route of venture capital, every investor is going to ask, you know, “What happens with AI?

[00:43:48] Does this become better or worse?” And if it doesn’t really go anywhere, things get much, much harder. Um, I’d love to hear Nathan’s answer to this question, since you’re… I mean, you see, again, we’re talking about HubSpot stock, and, you know- Right … there’s a whole con-

[00:44:00] Nathan: Yeah, I think, I think that we’ll learn over the next year or so which companies, I was, I was gonna say, have durable moats.

[00:44:07] Uh, I do think that there’s not much… Like, what’s a moat when the ocean… Like, what’s a moat in the middle of the ocean? It’s not really a, a, a thing. Um, I, I do think the valuations will come back as we see, um, or, or for types of companies, as, as we see what ends up being, um, being durable. Before you had to…

[00:44:28] Like, the person who had the idea and the person who had the skills to execute on the idea either had to be convinced that, to work together or, uh, be one employed by the other or something like that. Now, in more and more cases, that can be the exact same person, and you can go through so many iterations, and you can be like, “Oh, wouldn’t it be cool if this…”

[00:44:49] And then you, you know, speak it into existence. And you’re like, “Oh, actually that wasn’t as good as I thought,” or, “This is way better than I thought.” And so I think it’s really exciting that, um- Having ideas you can execute on them, you know, yourself now without needing someone else, at least for those early versions.

[00:45:07] Um, I think, so I, I think it’ll result in much better software products, much better platforms. Um, I do think that the speed of execution matters more than it ever has. It, it was the most important thing before, and it’s probably 10 times as important. Um, and so you have to, like whatever used to be a quarterly and then a monthly iteration cycle is probably a weekly cycle, and we should expect that to shorten further.

[00:45:35] My least favorite phrase is, uh, “By the end of the.” ‘Cause it’s just like a made up thing in business. Like, “Oh yeah, I’ll have that to you by the end of the week. Uh, you know, I think if we finish that by the end of the quarter, that’d be good.” I was like, why is June 30th the date that that… You know? Like, and so it just mean- it’s, it’s a signal inside of your company that someone did not think that through, and they just chose a convenient thing instead of thinking like, “Okay, that’s probably gonna take 36 hours, so yeah, no, we can have that by Wednesday at noon.”

[00:46:06] Yeah.

[00:46:07] Ankur: Can someone clip this video and whenever Nathan, someone says that in the ConvertKit Slack, it’s just a video of- … going under red.

[00:46:13] Nathan: There’s an agent-

[00:46:14] Ankur: It means you did not think it through.

[00:46:16] Nathan: There’s just an agent. Yeah. The best thing is I would probably say it, and then it’ll just reply to me. Um, I think, uh, who- Yeah, right there.

[00:46:24] You have a question?

[00:46:25] Audience member: Yeah. So one of the big things is like urgency, right? Like, for both of you, like in the companies you’ve built, like, like being able to move as quickly as possible to like solve the problem, because again, as the previous person said, like building is also easier. So getting to your first customers, building that sort of relationship, and building that mo- is more important than ever.

[00:46:43] So in that context, how do you guys, like what are your like first principles to stay focused in urgency? Because like everybody talks about moving fast, but I feel like sometimes you don’t necessarily know exactly what to do, but you want to do. If that makes sense. So like what are like the sort of north stars you sort of set to keep yourself like aligned?

[00:47:01] Ankur: Every business I’ve had has had like metrics we deeply cared about, so there was always the urgency still in some way, shape, or form had to kind of make sense for those metrics, and that always kind of focused us back. So for Carry, it’s like, okay, did this add customers or increase assets on platform?

[00:47:19] And if not, was it a building block to either of those things? Otherwise, like why are we doing it? Um, and that did help. I still personally believe, yes, there are downsides of like manic urgency or whatever, but speed of iteration is one of the only sort of controllable inputs that meaningfully changes the probability for success.

[00:47:41] So I’ll st- I’ll take the trade-off of someone doing like stupid shit fast versus the whole, you know, measure twice, uh, cut once approach. Um, but part of that is that’s the nature of how I like to work. There are founders who are the opposite, you know, very methodical, four years to launch a product. That can work for people, it was just not my specific style.

[00:48:03] Nathan: You have to be right for that, that ’cause you, you have so fewer, so many fewer, uh, chances for iteration. Uh, but I think that level of urgency is just towards a specific outcome. So you have to paint a picture of what the future looks like because you need to rally people Towards that outcome. You need a work back plan of how we’re going to get there and, uh, the metrics that you’re going to look at along the way.

[00:48:27] Um, but even the… You know, there’s little things like, uh, we have a new COO who just came into Kit, and he was like, “Hey, we’re, we’re evaluating our revenue and our growth numbers too infrequently.” I’m like, “We’re doing it every week.” He’s like, “No. Watch. Here’s how you calculate it on a daily basis, and here’s the outcomes.

[00:48:40] Here’s how it’ll shift the mindset for the team.” And I’m like, “Great. Okay. Let’s, let’s see that.” Um, but it really comes back to paint the vision for where we’re trying to go so we all understand that collectively. What are the metrics we’re going to use to track that? And then a work back plan. And then when you have that, then just absolutely as fast as possible.

[00:48:58] Did you have a question back here?

[00:49:00] Audience member: Yeah, I was gonna ask about you guys’ content workflows. I mean, you’re both super busy guys, but also prolific creators. So I’m just curious how you kind of balance those two things.

[00:49:09] Nathan: Content workflows. Do you wanna go first?

[00:49:11] Ankur: So I was actually just having this conversation.

[00:49:14] I, I realize I don’t like creating content for the sport of it. Maybe some people actually like it. I kinda don’t. And when, now that I’m no longer running Carry, where part of it was creating content, like you’ll see my content has dropped off 80 to 90%. Um, which was interesting, ’cause there are some people who do it truly for the love of the game.

[00:49:33] May- maybe you do. But I realize for me, content’s, it’s relatively speaking not a bad way to grow a business, and I like doing it for that reason. It can be fun in pieces. But I’m not a content creator at heart where I, I love this shit. Um, Twitter, I still like sometimes, you know, posting stupid things. But other content always takes a lot of effort for me, so my goal has been automate as much of it as possible, either with AI or have someone kinda do a lot of it for me.

[00:50:01] It’s just not what I found to be the thing that gives me joy.

[00:50:04] Audience member: When, when you were though, ’cause research and strategy is obviously a big part of content that actually performs, like did you, did that take a lot of your time?

[00:50:12] Ankur: Research and strategy was not a big thing for me. What, what helped a lot, at least with the content I did, which worked a lot of it, which was around personal finance, is a lot of this I was kind of learning myself.

[00:50:24] So every time I discovered something that legitimately I found surprising or, um, I did not know about, that I would share that, and that created a really nice reinforcement loop. Like, I was learning about a topic and I could share that, and that in turn found other people who were doing that. But I never went down the process of, okay, let me research popular topic, or popular videos in this topic or whatever.

[00:50:47] But then again, the channels that grew for me were all the text-based channels, which is very different. I never… I bet if I had to do a YouTube, that’s what the strategy would look like.

[00:50:56] Nathan: Yeah, I think that chasing what you’re interested in helps a ton. Um, we often have this idea that we need to be an expert before we can, you know, share from there.

[00:51:07] But often, like the most interesting things are what we just learned, and th- ’cause that excitement comes through, you know? Mm-hmm. When, when Ankur’s like, “Okay, I learned all the details of QSBS, let me write it up.” And people are like, “Wait, how do you know that?” And then they ask questions and, and it’s fresh.

[00:51:21] The other thing is, you know, we say like basically because someone teaches, we perceive them as an expert. And so- I would take the thing that you’re learning, the thing that you’re most excited about, and I would create content around that, and I would do it in real time, even if, um, you’re wrong about it.

[00:51:37] Or not wrong about it, even if you’re early on with it. So like, for example, I was learning to code in Ruby on Rails. This is like 20- uh, 2012, 2013. And I was getting stuck on the most basic things, and I would read these tutorials written by the experts who had contributed to the programming languages and everything else, and th- their tutorials, I w- I was getting stuck on things that weren’t covered.

[00:51:57] And then I came across a blog by someone who was, like, six months ahead in the journey than me, and they were writing stuff about like, “Oh, yeah, the total beginner gets stuck on this.” That everyone else was expert like, “How could, how could you be that dumb to get stuck?” And I was like, “Well, I was.” And so following someone who was just ahead of me in the journey ended up being the most useful thing.

[00:52:16] And so I try to pay that forward of sharing what’s fresh, what’s exciting, um, ’cause it often ends up being the most useful. But your question about workflows, just to talk about it. So, um, I, the last, like, year or so have made a big investment in building up my personal brand, and, you know, as a creator first and then kinda went behind the scenes, just heads down running the software company, and then now I’ve, um, brought back the, the content side of things, uh, ’cause I believe so much in the leverage of it.

[00:52:44] Um, but this time I’ve done it with a team. So, um, w- I have Chelsea, who’s here on my team, uh, in the back there, uh, who runs the… like, all of the operations for my personal brand as well as the Kit exec team. Um, and then she has reporting to her a head of content and head of social media. And so then they both are helping to pull ideas that I’ve shared, uh, help me re-record it.

[00:53:09] You know, it’s like, “Hey, this thing that you said in a podcast, like, there’s something there. Let’s write a newsletter about it. Let’s, um, uh, let’s re-record an Instagram Reel about that.” You know, maybe something that I fumbled over live, they’re like- There’s something good there. Let’s just ask you a question and give the crisp version that that will work as a, um, as a reel.

[00:53:27] And then we also work with a couple agencies. So, um, there’s an agency that does all of our podcast editing and, and clips. Uh, they’re called 7X Content out of the UK. Uh, and there’s another one called Ampersand Studios, uh, that we work with, uh, out in Boise, that they’ll come up with content ideas. Uh, and they’ll say like, “Hey, why don’t you, you know, create a reel or a post about this?”

[00:53:50] Uh, but really the podcast is at the core of everything that I do, um, or any time that I’m talking. And so the team is really good at mining when I say something interesting, and then deciding, okay, is that packaged well enough that it can be posted? Or is that interesting thing, could it be repackaged?

[00:54:08] Could we get you to say it again in a different format or with a better hook that then it’s worth posting? And so the ideas come first, and then we go, um, down from there, and that’s where the team can really help. Versus what a lot of people do, where they outsource the ideas and everything else, and it’s like you’re just another talking head on the internet.

[00:54:26] Ankur: I’m excited to see the real version of how EOD means you’ve not thought it through. So

[00:54:31] Nathan: looking forward to that. Yeah, exactly. See how that plays out. Um, who else has a question? I think we have time for… Let’s do two more. So we’ll go here and then back over to here.

[00:54:39] Audience member: Hey, guys. Uh, thanks for doing this talk today.

[00:54:42] Uh, I had a little bit more of a specific question. I know you guys mentioned you have a strong background in angel investing. Uh, so a few f- friends of mine, uh, and me are building an alumni angel network actually for our school, Rutgers. Um, but Rutgers doesn’t traditionally have a background of like, uh, startup operators or, um, I guess investors or people that go into that route compared to like Harvard or Stanford or other Ivy Leagues.

[00:55:05] So I was gonna ask from a background like yours, what would you suggest that, um… Or like strategies that we should use to try to build that, considering that it’s like a more of an emerging ecosystem now?

[00:55:16] Nathan: Well, first I was gonna say angel listing or angel investing is something that, uh, I thought would be really cool and fun, um- I don’t enjoy it at all, and I don’t enjoy the g- the, the K-1s that come back from it and everything else.

[00:55:29] So that was something that, you know, my hot take is I don’t like angel investing and, um, and I don’t know, I did 10 or 12 or something like that. Made some really good money on some of them, but I was like, “Oh, wait, I don’t… Just because everyone else does this as a founder, I don’t need to do that.” And it’s so freeing to be like, “Oh, yeah, no, I don’t, don’t do angel investing.”

[00:55:46] But you have a different take. I was,

[00:55:47] Ankur: I was gonna challenge the other assumption. Yeah. Um, well, yeah, I always say angel investing is, like, the most expensive newsletter subscription in the world, right? Like, phew. But, um- Yeah,

[00:55:56] Nathan: how to, how to lose money $25,000 at a time.

[00:55:58] Ankur: Yeah. I guess I would ch- I, I… Yeah, I would just challenge your assumption a little bit.

[00:56:03] Like, what, what about it makes you think there’s, like, network effects of tying it to a specific university? Like, is it the fact that… Like, what, is it the fact that, um, you’re gonna invest in other Rutgers founders? Or, like, why, why tie it to the university, I guess? I

[00:56:19] Audience member: guess the assumption was that, uh, you know, we wanted to build that ecosystem up within Rutgers, like, to build a brand image, and to kind of pay it back, pay it forward to, you know, where we came from, that kind of thing.

[00:56:29] Ankur: Got it. Um-

[00:56:30] Audience member: Because, like, for context, like, we built our, um, like, our Rutgers Entrepreneur Society, like, our club from the ground up, as well as, you know, a few other programs that are all, like, that coincide with each other. And so, like, passing that on to the next generation kind of thing, building it over n- or over time.

[00:56:47] Ankur: Got it. Makes sense. Um, so I think with, with angel investing, my general sort of guidance to people is it can be, it can be profitable, it can be fun. However, it’s a sort of thing that if you wanna do it, you wanna take many shots on goal. Um, it’s like, whatever budget people start out with, like, divide it into at least 20 little slugs because each…

[00:57:10] Like, as an aggregate, this model works because one company is an outsized success, and the only way to have any kind of predictability around it is to have a large sample size, um, of companies. Now, if I were to think about what I could do to grow this investment club, I think, I think it’s do you, do you get access to a lot of interesting deals?

[00:57:32] Like, any of these investment clubs really work when you have one thing truly kind of work, and then that becomes, becomes the example. So I would turn that back to you. Are there, I don’t know, very successful companies started by Rut- Rutgers alumni or something, and use that to kind of bring people in?

[00:57:48] Audience member: Mm.

[00:57:49] Got it. I mean, yeah, there are a few. Like Bloomberg, for example, one of the founders of Bloomberg was a Rutgers alumni. But I guess what we’ve noticed is that a lot of, uh, founders who have previously been from Rutgers, or founders, investors, whatever, they tend to kind of levera- or they, when they move up to a higher brand, I guess, for example, like their company or, uh, let’s say an MBA or something like that, they tend to, you know, drop the Rutgers, uh, affiliation per se.

[00:58:13] Ankur: Yeah, that would, that would be kind of be the challenge I would think as well. Like, I went to Cal Berkeley. I have… My school pride extends to sports, not beyond. Like, I don’t, I don’t like… Yeah, I watch the football team, I watch the basketball team, but I don’t feel super strongly or connected to, like, a very large state school with tens of thousands of people, and, um, that I picked because I didn’t get into Stanford.

[00:58:34] So I don’t, you know, I don’t, I don’t have super strong affiliation.

[00:58:38] Nathan: I would say, uh, think really clearly about the problem that you’re trying to solve. Sometimes we get excited about our particular solution, you know, like, oh, we’re going to use technology to network, you know, the angels in, in this community or whatever else.

[00:58:50] But it might be if you’re… If reputation is what you’re solving for, there might be better ways to… Like, storytelling of the companies that have come out from Rutgers alumni or something like that might be a much better way to accomplish that so that people are like, “Hell yes, this is the school that I went to,” instead of like, “Well, that’s where I started, but then I got an MBA from wherever else.”

[00:59:09] So think about what you’re optimizing for and work backwards from that. Um, let’s jump over… I think you’re one of the last ones, so maybe we can, Daniel, pass the mic over and-

[00:59:16] Audience member: My question is more about, uh, like you’ve been like a 2X, 3X founder now. Uh, how has your approach towards product market fit really changed over the years and all the time that, uh, you’ve like, uh, done things and, uh, like even for you, like, do you think there’s like a change?

[00:59:36] Because, uh, you, you both mentioned it’s like the hardest thing for you all. So how, how do you all approach that if

[00:59:44] Nathan: How do, how do we approach which part of it?

[00:59:46] Audience member: Uh, product market fit in general. Like, how has it changed for you over the years?

[00:59:51] Nathan: Yeah. I mean, you could say that I haven’t started another company because I’m too scared to face the abyss of a product market fit over again.

[00:59:57] Like, that’s the, uh, that’s the hard- like the absolute hardest thing, and you can’t buy it. Like, yeah. I’ll think about my answer more. Do you have, have some thoughts?

[01:00:07] Ankur: Yeah, I think, I think it’s not binary. I used to probably in the past think it’s more binary, like you either have it or you don’t. But with Carry, we had product market fit for a relatively small market.

[01:00:20] So we had like small product market fit, which was a good, not great company. So as I think about product market fit now, I think it’s, it’s as important as ever, but it’s not just any kind of product market fit. It’s product market fit in a very, very, very large market. Um, so that does change my thinking.

[01:00:37] Um, I think from … One thing I may do differently if I ever am stupid enough to start another company is I would probably promote and market it a lot less early on, find other signals, and try and like really make the product market sort of engine work before fully even committing to like, okay, I’m gonna go out and raise money or whatever.

[01:01:03] Like, I’d be fine taking that risk off my balance sheet and see, can I build something that is working in a really good way? And only then go out and raise capital, go out and, you know, do the whole company thing.

[01:01:17] Nathan: I think that’s a hard part about having an audience or a reputation as you come in, because it’s sort of like getting the advice from your friends and them lying to you.

[01:01:25] Your audience can do that in the same way. They’re like, “Oh, this is the coolest thing. I’d buy it just ’cause your logo is on it or, or because you’re, you’re building it.” And it might not be sustainable. And so you have to … You both should take advantage of every single opportunity you have. Like, I had this idea when I launched Kit early on that I didn’t want to use my audience because that was cheating somehow, which is the dumbest idea.

[01:01:48] Like, if you’re trying to, like, do one of the hardest things ever of, of build a company, like, use every advantage you have. Like, every unfair advantage. Um, but then you also have to, if you rely on an audience, you have to go find the people who don’t know you at all, and seek them out, and be like, “Hey, will you buy it?”

[01:02:06] And they’re like, “I have no idea who you are, but actually that sounds like that solves a real problem for me. So yes, I will, I will buy that.” All right, we gotta wrap up there. This has been a lot of fun. Thanks for coming to the very first, uh, live podcast at Kit Studios. I appreciate it. And Ankur, thanks so much for coming out.

[01:02:21] Ankur: Yeah, thanks for having me.

[01:02:24] Nathan: If you enjoyed this episode about building a company on your own terms, definitely check out episode 81 with Justin Jackson. He’s the co-founder of Transistor, which is a beloved podcast hosting company he built without any outside money. So that’s a great bootstrapping story if you’re interested in keeping control of what you build.

[01:02:41] Like the video if you enjoyed it, hit subscribe on YouTube, wherever you’re listening, and

[01:02:45] I’ll see you next week.

[00:00:00] Tyler: We are all tenants on YouTube’s land, on Meta’s land, on TikTok’s land, and, and they can kick us off at any time.

[00:00:07] Nathan: YouTubers are sitting on businesses worth far more than they realize. Many have built their entire enterprise on a platform they don’t own.

[00:00:13] Tyler: If any of your channels goes down tomorrow, you have no way to reach your audience.

[00:00:18] Nathan: Tyler Chow has spent 20 years as an entertainment attorney at Disney, Skydance, and BuzzFeed, and she was lead counsel on 18 feature films. Now she represents some of the biggest channels on YouTube.

[00:00:29] Tyler: One thing I want to caution creators about is-

[00:00:34] Nathan: She explains what makes a business worth buying, but also why some creators don’t need to sell at all.

[00:00:39] They actually just need to take a sabbatical.

[00:00:40] Tyler: The number one question I get from creators is, “Tyler, is this it? Like, do I just make videos for the rest of my life, because I’m getting really tired?”

[00:00:48] Nathan: Investors and studios are buying up creative businesses, and Tyler’s the person who runs those deals. A

[00:00:53] Tyler: lot of creators will say to me, “Well, like, what product should I launch?”

[00:00:56] Mm-hmm. Like, I don’t know. And this is my favorite strategy.

[00:01:00] Nathan: I love that

[00:01:05] Tyler, welcome to the show.

[00:01:07] Tyler: I’m so honored to be here. Thank you for having me.

[00:01:09] Nathan: So you and I have some of the favorite, like, our, some of our favorite topics in common- Mm-hmm … which is building large businesses, creator-led, and doing it in a way that is sustainable and everything else. Yes. So we, you’re talking to creators right now about how do you build for an exit, how do you protect your IP, all of those things.

[00:01:28] What are some of the things that you’re seeing right now in the creator space? Because you’re talking to private equity or any of these others. You know, they’re coming and they’re saying, “Hey, you have attention, we have money. What should happen?” Like, what, what are you hearing from the private equity side and the creators and, and the match or the mismatch that’s happening right now?

[00:01:43] Tyler: Well, so what’s super exciting is private equity fund, studio streamers- Mm-hmm … all understand now, right? We’ve, we’ve been talking about it for years- Right … but they finally are here. They get it. They get it. They’re like, “Okay.” Clearly, you know, Unilever last year saying, “We’re dedicating 50% of our ad spend to creators- Wow

[00:02:03] in digital media.” And I think that was a big indicator for the big Fortune 500 companies to start paying attention. Mm-hmm. So the private equity funds are coming and saying, “Okay, we wanna buy YouTube channels.” But what does that mean? I just came back from Cannes Film Festival. Mm-hmm. My first time. I, I, I was in Hollywood for 20 years and I never got invited.

[00:02:23] But now that I represent big YouTubers, now they wanna hear me talk. Yes. And so it was, it was r- quite a, you know, kind of watershed moment, and they had their first creator summit there. And I think private equity funds are saying, “Well, what does it mean to buy a YouTube channel?” Right? Mm-hmm. Or, what i- what does it mean to buy a creator-led business?

[00:02:42] Because they think, “Well, it’s a YouTube channel. I guess there’s AdSense dollars, you know, I think there’s brand deals, but there’s so much risk around the key man.”

[00:02:50] Nathan: Oh, yeah.

[00:02:50] Tyler: Right? So what happens if this YouTuber doesn’t wanna make videos anymore? You know, are, are we buying, I guess, is it maybe the back catalog?

[00:02:58] Is it the videos? You know, can we, can we license it to streamers? And, and yes to all of those. But the clients that I’m selling for $100 million have 15 revenue streams in addition- Mm … to their YouTube channel, because they’re building on their own land. They have an email list. They have a newsletter. Yep.

[00:03:17] You know, that’s very important. Owning your audience is The data, you know, data is the new oil. Like, you need to own your audience. I was at a master class back in December with te- 10 of the biggest YouTubers, all over 10 million subscribers. I asked them, I said, “With… You know, can you raise your hand and let me know how many of you have an email list of your audience?”

[00:03:38] Do you know how many raised their hands?

[00:03:40] Nathan: Oh, I’m guessing four.

[00:03:42] Tyler: One.

[00:03:42] Nathan: One. Oh, no, 10%.

[00:03:45] Tyler: I know. And I said, “So if y- any of your channels go down, goes down tomorrow- Right … you have no, you have no way to reach your audience.” Mm-hmm. 10 million plus. And I think the horror on their face, I think they’re starting to figure it out.

[00:03:57] Because what we’re seeing in the marketplace is a lot of creators are approaching burnout, right? Yeah. We’re six years from COVID, where a lot of creators started their channels, and the number one question I get from creators is, “Tyler-” Is this it? Like, do I just make videos for the rest of my life? Mm.

[00:04:16] Because I’m getting really tired. Right. So a lot of them are coming to me asking me, “Okay, what is … Like, how do I get off this hamster wheel?” And so that’s where a lot of the interesting conversations are happening. I’m running three active exits in, in the creator space right now. I have about three to five YouTube channels that are sort of behind them who are saying, “Okay, I wanna exit in a year or two.

[00:04:37] Get me buttoned up. You know- Mm … do I have clean chain of title?” Which, by the way, they don’t even really know that until I explain, you know, “Do you have clean B-roll? Do you have clean music? You know, do you have, um, work-for-hire language for your employees or independent- Mm … contractors?” The answer to that is usually no.

[00:04:52] Nathan: Okay, so I wanna dive in on the mistakes that people make and how to fix them early. But before we do that, let’s talk about the business model.

[00:05:00] Tyler: Okay.

[00:05:00] Nathan: So when we’re going to, say, an exit for $100 million, like, what actually is being purchased in that?

[00:05:06] Tyler: Sure.

[00:05:07] Nathan: There’s the channel and the audience, but also usually there’s a bunch more revenue streams.

[00:05:11] Tyler: Right. So sometimes, you know, the newsletter can be very valuable. Yeah. But a lot of my client, Jim Louderback, you know, he sells brand sponsorships and placements in his newsletter. It’s that captive audience. You know, if you have- Right … 30,000 of a specific audience in your newsletters, like, brands and, and the buyers potentially want that audience.

[00:05:31] Do you have a community? Mm. Do you have a course? Uh, do you have physical products? And my favorite right now are technical products.

[00:05:38] Nathan: Okay.

[00:05:38] Tyler: You know, um, apps. And I’m sure you’re seeing this, like, every single, every other one of my clients is like, “Oh my God, with Lovable and Claude, I’ve created three apps.”

[00:05:47] And it looks great- Yeah … and it’s beautiful, but then we, we bring, I will bring in a proper CTO for them who are, who are actually- Who can scale it … who are auditing it right now to even see if this is something that can go to market. Digital products I think are really important. I mean, I, I recently met someone who made six figures, you know, selling an $89, you know, digital product.

[00:06:09] Um, I think there are so many different ways to make money off-platform, right? I’m a, I’m a big proponent of, you know, we are all tenants on YouTube’s land, on Meta’s land, on TikTok’s land. Yep. And, and they can kick us off at any time, and YouTube is doing huge cleaning up right now, right? They’re terminating channels.

[00:06:27] They’re de- demonetizing. I’m sure you’ve heard of the stories, uh, probably friends who’ve asked you, “Oh my God, I lost my Instagram page. Can you help me get it back?” Mm-hmm. And Meta just doesn’t even respond to … There’s n- no live person. So the anxiety of building on someone else’s land is, I think, becoming more and more clear to creators- Yeah

[00:06:46] that they need to build somewhere else.

[00:06:48] Nathan: What are the things that you’ve said or how have you been able to convince them, besides the fear of loss? Like, we’ve, we’ve covered that, but- To get them to say, “Okay, I have five million subscribers to my YouTube channel, you know, I’m going to follow in the footsteps of like…”

[00:07:00] I think, like, Veritasium is a good example. They’ve built a really meaningful email list. Sure. I,

[00:07:04] Tyler: yeah, we should talk about Veritasium and MatPat. You know- Mm-hmm … those are the two YouTube channels that have sold to private equity, and they’re case studies right now. You know, private equity funds look at them and say, “Well, was that a successful acquisition?”

[00:07:16] Yeah. And the attention and, um, the views have gone down- Right … right, since… I mean, Veritasium has done a really good job. Like, he, Derek didn’t even really tell anybody for a year.

[00:07:28] Nathan: Yep.

[00:07:28] Tyler: And he’s like, “Surprise. Like, I’m actually not the owner anymore, but you guys haven’t noticed.” And

[00:07:32] Nathan: hadn’t been for quite a while.

[00:07:33] Tyler: Right, and I, and you haven’t noticed any difference, and this is, you know… So I think he’s done a really good job. You know, MatPat, I, I, um, I don’t follow it quite as well, but I, I, and I don’t know, you know, I wasn’t their attorney on those deals, so I don’t quite know, you know, the structure. But I do think, and you, we were talking about this off camera, I sometimes will convince m- creators or my clients to not go towards an exit, you know?

[00:07:58] Mm. The, the $100 million one that I’m running right now, we went out to market 18 months ago, and we were told that his business was worth 35 million.

[00:08:06] Nathan: Okay.

[00:08:06] Tyler: And I told him, I said, “You know what? Let’s wait three years. I think you’ll hit 100 million- Mm … in three years.” And I was wrong, because we hit it in less than a year.

[00:08:14] But that was because in that year, we built out the team, we, we, we put in more revenue streams. We built an amazing technical app, a budgeting app- Mm … that we’ll pro- we could probably spin off for 30 or 40 million on its own. And that’s what investors are looking for, right? They’re, they’re wanting independent streams of income that does not rely on the creator’s face.

[00:08:35] Nathan: Right.

[00:08:35] Tyler: Mm-hmm.

[00:08:36] Nathan: So in that example, if someone comes to you and, and says, “Hey, I have this $30 million exit,” as an example, “and should I take it or not? And if I were to take it, can you help me shepherd it through to the, to the finish line?” And you’re saying, “Hey, I actually think, you know, if you’re asking for my opinion, I think no, you shouldn’t, because you could triple this over the next few years,” what are the things that you’re encouraging them to do between, you know, day one when they bring it to you and a year or three years later when it’s like, “Hey, this is worth three times as much”?

[00:09:06] Tyler: So typically I will come in and do an audit for them and say, “Okay, what does your cor- corporate structure look like?” Okay. You’d be surprised. I’ve seen creator businesses making 10 million a year that goes through one single LLC, right? So they need a parent company. They need subsidiaries. Mm. You know, one that holds the YouTube channel, one that holds the technical app, one that holds the pr- pr- you know, physical products because every, you know, revenue stream has its own liabilities.

[00:09:32] Let’s say you have a supplements, you know, product line. Right. I wanna make sure that if anyone gets sick from that line, that they only, they’re only suing the product line, right, that LLC, not your YouTube channel, not your technical app, not your courses, you know, not your other things, not your real estate, you know.

[00:09:49] Mm-hmm. Because I also have clients who have their real estate in all of the same LLC, right? And so that’s kinda step one. Step two is what do your employment and independent contractor agreements look like? Do you have work-for-hire language that actually says you own the IP that they have created for you?

[00:10:06] This is very important for technical creators, you know, um, for creators who have technical apps if they have people building code for them. If they… If you don’t have that agreement, like, that CTO or that senior developer can walk away with the code and say, “That’s mine.” And I had this happen to one of my clients Where the CTO walked away with a lot of code, and they had to start over, and it was terrible ‘

[00:10:30] Nathan: Cause everyone assumes I hired you.

[00:10:33] Mm-hmm. I paid you for a service to write this code- Mm-hmm … and so I own it.

[00:10:36] Tyler: Mm-hmm.

[00:10:37] Nathan: And that is not the default way that it works. It works that way if it’s in the contracts.

[00:10:41] Tyler: Correct.

[00:10:41] Nathan: But otherwise, it’s not.

[00:10:43] Tyler: So first is, uh, corporate structure. Second is e- employment, independent contractor work for hire. Mm-hmm.

[00:10:51] Now, there’s also another wrinkle in there, which is huge, is do you have hidden misclassification lawsuits in there that the buyer will tear apart? Because that is something that’s huge in the creator economy.

[00:11:03] Nathan: And is this misclass- classification of employees, or

[00:11:07] Tyler: what? Well, so you, you will have independent contractors who work for you.

[00:11:10] Right But they really are employees. Mm-hmm. Because they’re working eight hours a day for you, 40 hours a week. They might be abroad or, you know, they’re mi- they might be remote, so you think, “Well, they’re not a full-time employee.” I, I know of creator businesses that have hundreds of independent contractors who are, who should be W-2 employees who are not.

[00:11:29] Once a buyer comes in and sees that, they will walk away- Mm-hmm … from that deal or reduce, you know, the purchase price by 50% because those are just lawsuits waiting to happen. And this is a, the, the… I, I will share this kind of like very insider information. Here’s what happens. Let’s say you have an independent contractor who works for you for a couple years.

[00:11:51] They leave, and, and you leave on good terms, right? Mm-hmm. Then they go file for unemployment, and then the labor d- commission will say, “Wait a minute. We’ve never received any W-2 from you. Why are you filing for unemployment?” Then they come and audit the creator.

[00:12:08] Nathan: Mm.

[00:12:08] Tyler: And that’s when they find the hundreds and hundreds of misclassifica- in misclassified employees, and those fines are very expensive.

[00:12:17] Mm-hmm. And so that’s something that I deal with for a lot of my clients. You know, do you have disgruntled employees? I mean, you look at MrBeast and his latest lawsuit of that woman, you know, who says that she took a call in the labor room, you know, and was, was let go when she came back from maternity leave.

[00:12:34] Those types of gender discrimination- Mm … you know, um, sexual harassment, any of those things, those are heavy, expensive lawsuits that buyers are going to be looking for in due diligence.

[00:12:46] Nathan: Right.

[00:12:46] Tyler: Clean chain of title. Do you… Every video you’ve made, do you actually own the music, the B-rolls? Um, is, is… I mean, reaction channels are worthless.

[00:12:58] Like, if you have a big- Okay … reaction channel, no buyer will touch that because you don’t own any of those videos.

[00:13:03] Nathan: Mm-hmm.

[00:13:03] Tyler: Right? You could have hundreds of millions of views per video, but no one will touch that. Reaction… I mean, my one advice to anyone who’s watching, you know, is if you have a reaction channel seriously reconsider it.

[00:13:17] Or do it the right way. Go to the small creator that you’re reacting to and ask, either ask for their permission, co-collaborate with them on YouTube- Yeah … or pay them $50, you know, or what- whatever minimal amount to get their, their, the rights to, to that video. Because I’m seeing IP trolls coming out of the woodworks attacking big creators.

[00:13:38] Because you know what they do is they, the IP trolls, let’s say y- you’re a big creator and you have a compilation video with, like, 50, you know, TikToks in there. What the IP trolls will do is they will go to the 50 individual ones and buy the clips. And then they go- Oh, and so they own it now … and then they go to the big creator and

[00:13:57] Nathan: say- Because it actually probably only cost a couple hundred dollars-

[00:13:59] Tyler: Yes

[00:14:00] Nathan: per, per clip or something

[00:14:01] Tyler: like that. Or less, right? Yeah. And or they even say, or, or they’re even trickier and they’re like, “Oh, we are a clearing house, a licensing house. Give us the clips and we will sell them out, you know, and license it to studios.” So then they go back to the big creator and say, “Pay me six figures or I will take your channel down.”

[00:14:18] Nathan: Mm-hmm.

[00:14:19] Tyler: And w- I’ve had to step into some of those deals and negotiate with them because YouTube actually says now, “We don’t help big creators with copyright strikes- Mm … because it’s a, it’s a legal issue that they cannot help with anymore.” They’re not gonna

[00:14:33] Nathan: get in the middle of.

[00:14:34] Tyler: Because YouTube- Mm-hmm

[00:14:35] probably gets millions of copyright strikes a day. Yeah. And they just can’t step into that. They used to. I, I heard in the past four or five years ago, you know, the big YouTubers would get help from YouTube, but now they don’t do it anymore.

[00:14:47] Nathan: Hmm. Okay, so that’s a whole bunch of things on the negative side, right, that you go through and clean up.

[00:14:52] Anyone who’s listening who’s like, “Wait, I’m, I’ve got 100,000 subscribers,” or or you know, “I, I just earned $100,000 a year in revenue-

[00:14:58] Tyler: Mm-hmm …

[00:14:59] Nathan: wait, I can actually start to fix this now.”

[00:15:01] Tyler: Oh, yeah. I mean, it’s much easier to fix it sort of earlier on-

[00:15:05] Nathan: Right …

[00:15:05] Tyler: than to try to do it, you know, backwards to, to try to capture maybe the hundreds of, you know, independent contractors or editors- Mm-hmm

[00:15:13] or people or, or, or B-roll clips that you’ve used or music clips that you’ve used. And, and I think most creators are savvy enough now. Yeah. They use, you know, like Epidemic Sound- Epidemic Sound, yeah … or, you know, different companies like that. And, and so I think music at least they understand. B-roll, B-roll is tricky, right?

[00:15:32] ‘Cause people will pull movie clips right into their- You’re right … and, and they think it’s fine. And I think in general it’s fine. You know, the advice I give to creators is if your use is positive or neutral, it’s probably fine. It’s only when you go really derogatory or you take y- or you say, “This is a terrible,” you know-

[00:15:49] Nathan: Yeah

[00:15:50] Tyler: “piece of film,” then maybe the studios will come after you and say, “Well, n- I, I didn’t give you a license or permission to use this.”

[00:15:57] Nathan: Right. Okay, so what should people do on the positive side? Mm-hmm. Uh, like let’s go maybe less on the IP and legal side and more on the on, the business side.

[00:16:06] Tyler: Sure.

[00:16:07] Nathan: Right? Of if we have this channel, we have all this attention, what do we direct it towards in order to build, like, real enterprise value?

[00:16:15] Tyler: So I think for a lot of creators, and you know, I say YouTube a lot because- Mm-hmm … that’s where most of my, my i- my clients are, you know? Yeah. The, the ones making long-form content are the ones creating media and real businesses. Um, sorry for the ones who are, are watching who might have short-form content.

[00:16:30] It’s just like it, it’s not quite there. I mean, I think short-form content you can make good living on the brand deal side. Mm-hmm. But there’s less sort of enterprise value. You know, you can’t license your content to Netflix or, or Tubi. You know, you can’t really become a production company in that way.

[00:16:46] Right. Um, so I think on the YouTube side, your first two revenue streams are AdSense and brand deals, and you should have those. Mm-hmm. Those are your kind of your foundations. We’ve talked about, you know, could you do brand placements in newsletters? What about a community? What about some type of course?

[00:17:03] You know, a lot of my clients tend to be educational or professional channels, so they have some type of wisdom or knowledge to impart to their audience.

[00:17:11] Nathan: Right.

[00:17:11] Tyler: And then the actual revenue streams that can come from having a physical product. You know, I, I know the biggest ones that people talk about are like Feastable and Prime and Emma Chamberlain Coffee.

[00:17:21] Now, I think consumables are, have very sh- small margins. It’s not a great, you know- Yeah … um, you have to just sell a lot, right? Like MrBeast does sell millions of, upon millions of units of Feastables and, and that’s how he makes money. But I think, you know, having digital products, I think having different types of physical products, technical products, that’s where we see really high multiples.

[00:17:45] You know, th- those are the 10 or 20X multiples that we’re seeing because buyers love reoccur- recurring revenue. Yeah. Right? It’s a SaaS product. You build it once, you can sell it to 10 million people, and it’s like, what’s your monthly, you know, revenue? What’s… You know, they look at churn. But it’s the easiest, I think, product to make for creators, especially with Lovable and Claude.

[00:18:06] You know, you can go make a lot of apps on your own now.

[00:18:09] Nathan: And you have the distribution. So what’s becoming the harder part, it used to be that building software was very hard.

[00:18:14] Tyler: Right.

[00:18:14] Nathan: And now building software is quite easy, relatively. Mm-hmm. Now building it in a way that scales and is secure and all of that.

[00:18:20] Tyler: You do need to bring a CTO in, okay? Yes. I, for, for all of the, the kind of like the vibe coders out there who are like, “Oh my God, I have this great product,” I, I’ve, I actually have three clients right now who all have told me the same thing, and I have another client who’s a senior developer who, who is offering fractional CTO services.

[00:18:37] Mm-hmm. So she’s coming in actually auditing these apps and saying, “Okay, actually, do you have a viable-” product, or do you think it’s, like, pretty right now? Right. Because that’s different, right? When you, when you put it out into the marketplace, and then you’re actually getting customers to use it, you know, that’s different.

[00:18:55] Nathan: Yeah. So having that checked, you know, by a- Mm-hmm … someone who, who’s a professional and, and, you know, building a team behind it is really important. But I, I think the advantage swings even more in the favor of creators now because they have distribution. Yeah. And they have brand.

[00:19:10] Tyler: Mm-hmm.

[00:19:10] Nathan: Um, so before if it was, like, maybe 50/50- Yeah

[00:19:13] like distribution and brand and software.

[00:19:16] Tyler: Mm-hmm.

[00:19:16] Nathan: Now the, the software’s become substantially easier- Yeah … and the distribution brand is, you know, still just as effective as ever.

[00:19:23] Tyler: And, and I think it’s really exciting because… And, and, and so a lot of creators will say to me, “Well, like, what product should I launch?”

[00:19:31] Mm-hmm. Like, I don’t know. And I… And this is my favorite strategy. Ask your audience, you know, “What products do you love? What is a pain point that you’re struggling with right now that maybe we could solve together?” Um, one of my clients, um, uh, is called A Life Engineered. You know, he has a small channel.

[00:19:49] It’s… I mean, small. Okay, 200,000, right? Like, he’s- Right, in the

[00:19:51] Nathan: scale

[00:19:52] Tyler: that you’re working with. In the scale of… Some of my clients have 10 or 100 million, right? Right. But it’s a great, very niche audience, right? So he, w- what his channel is about is, so he was a level seven engineer at Amazon. Do you know this channel?

[00:20:07] Have you heard of it? I don’t, no. Okay. So he was, he started this channel while he was working at Amazon. Amazon knew and, you know, they were fine with it. And his product wasn’t competing with anything he did in his day-to-day, was he was teaching engineers soft skills on how to do well on interviews, how to do well on their, you know- Mm-hmm

[00:20:25] 360 reviews within the company so that they could get to the next level engineer. Yep. Because that’s 100,000 usually, you know, every time you, you elevate a level. So then he, he launched a course that taught people how to do it. And we launched his course two times. It made over 400,000. And he was like, “If I’m doing this part-time, I wonder what I could be making full-time.”

[00:20:48] Mm-hmm. And so he quit his job last year, did it full-time. And what’s really cool about that is he asked his audience, like, “What is your pain point?” Right? And for a lot of them, they said, “Well- I always do terribly on my internal reviews. You know, like, I don’t know how to promote myself. I don’t know w- how to remember w- what I did well.

[00:21:07] And he actually has this great idea called a brag binder, right? Every time you do something well, like print out the email and just, like, put it- Mm-hmm … in this binder, ’cause you know we forget as time goes on. And then at the end of the year, show it to your supervisor and say, like, “These are all the things I’ve done this year.”

[00:21:21] Right. “You probably don’t know that because you’re not in the, my day-to-day.” And that’s really smart. So they’re very tactical things that he was helping his audience solve. They had a pain point. So I think, you know, poll, y- poll your audience and say, like, “What product would you need?” You know, a lot of photographers do this really well.

[00:21:37] You know, they, they create certain pieces of, of equipment that is like, that they needed for themselves. And so- Right … so then of course, other photographers need it. I think there’s really a way to involve your audience, because when you involve them, they feel a sense of ownership, right? There’s this creator called Mai Pham who has a hoodie.

[00:22:00] It sounds really simple, but she’s really smart. You know, she does an exclusive launch every three to four months. It’s that single design. When it sells out, it sells out. She never repeats it. Mm. So, like, people go crazy. Like, you know, she puts out a password that you have to enter. And I know this because I actually have bought her hoodies.

[00:22:20] Right. And I buy a lot of creator-led products just to see how they are, and it was… Nathan, it’s like the best hoodie I’ve ever owned. And it’s like $140. Yeah. It’s really soft. There’s like an individual, like, you know, um, message in there. Things like y- what you’re s- what you seek is within. You know, it’s very Zen-like.

[00:22:37] But what she’s really smart in doing is she brings her audience in every step of the way, from design, you know, she shows them the design. She has them vote on it. She takes them to the factory. She shows them, like, when, when the products go wrong, you know, when the stitching is wrong. So she’s … So by the time the product comes out, like, the audience is so, you know, invested in this product.

[00:22:59] They’re like, “We need to have it because we helped her design it. We helped her-” Mm-hmm “… you know, produce this product.” And I think that’s really smart. And she makes millions of dollars a year, by the way, selling these hoodies.

[00:23:11] Nathan: I think one of the best things is when creators introduce artificial scarcity.

[00:23:15] Mm. And it can even be real scarcity at first, right? Yeah. ‘Cause you’re like, “I don’t know. Are people gonna buy 1,000 of these? 10,000?” Mm. Let’s, let’s do 2,000 to play it safe. Mm-hmm, mm-hmm. And the audience is like, “Are you kidding? We’ll buy 2,000 in-” Yeah … “12 seconds,” you know? Mm-hmm. But you end up in this place where if you deliberately- Say, sell 50% of the demand that you had- Mm-hmm

[00:23:34] or you, you know, cap, cap supply at 50%. Mm-hmm. Then you stay on this train of, like, people always wanting more.

[00:23:40] Tyler: Yeah.

[00:23:41] Nathan: And so there was a… When one of my kids, this is years ago now, was a baby.

[00:23:46] Tyler: Mm-hmm.

[00:23:46] Nathan: There was a baby carrier that was made by a small company.

[00:23:50] Tyler: Okay.

[00:23:50] Nathan: And they only had so many of them, and so they kept selling out.

[00:23:53] It’s like- Was

[00:23:53] Tyler: it the one on the hip?

[00:23:54] Nathan: Yeah. ‘Cause I loved

[00:23:55] Tyler: that

[00:23:55] Nathan: one. You can do it as a front carrier- Yeah, yeah, yeah … or the hip or all of that. Yeah. And it, it was an excellent carrier. Mm-hmm. People loved it and all that. Mm-hmm. But instead of figuring out, “Okay, how do we scale supply 10X to be able- Mm … to fulfill all the demand?”

[00:24:06] They said, “Wait a second. This is a feature, not a bug.”

[00:24:08] Tyler: Mm.

[00:24:09] Nathan: And so what they said- Smart … is every Thursday at 11:00 AM Eastern, we will post all the inventory that we have in our Facebook group.

[00:24:16] Tyler: Mm-hmm.

[00:24:17] Nathan: And then whoever gets one gets one, and then the rest of the time, you know, maybe there’s some used ones selling or…

[00:24:22] And they just continually got more and more demand, and people would be like, “Wait, how did you get one?” It’s like, “Well, I was in the Facebook group- … at 11:00 AM Eastern, and I bought it immediately.”

[00:24:28] Tyler: The exclusivity is so smart, but it’s just human psychology. Right. Because if you’re, if you’re told you can’t have it, you’re like, “Well, I need it.”

[00:24:36] Nathan: Right.

[00:24:36] Tyler: Right? And so, you know, I’m, I’m actually launching a, a creator exit accelerator soon, and I’m, I’m, I’m, I’m capping it at 10 spots because- Mm-hmm … I, I think that’s how you give, you know, people the right attention. But when people hear 10 spots, like, I already have a few signed up. They’re like- Right

[00:24:50] “Well, I want my place in that same 10 spots.” So I’m not trying to create scarcity because I have to do actual audits with them, you know, one-on-one, so like over- It involves your time. Yeah. Yeah. And over eight weeks. Like, I can only do so many. So humans are interesting because if you tell them, “Well, you can’t have it,” they’re like-

[00:25:08] “Oh, no, I need it.” Right? So there, that, there’s definitely some strategy that we’re, we’re, we’re- Yeah … sort of, you know, I think imparting to your audience that think about a pain point that you can solve. Mm-hmm. And then be realistic about how many, you know, items, you know, how many units you can launch.

[00:25:24] Because… So this is another part where, you know, a lot of my clients come to me and say, “Well, I wanna la- launch a physical product.” And I say, “Okay. Well, it’ll probably cost $10,000, you know, to do this first initial launch.” Right. That’s not a small amount of money. You know, that’s an investment. So perhaps that first launch is 500, you know, units- Mm-hmm

[00:25:43] or 1,000 units, and it’s a test, you know? And, and so I think a lot of the times a la- the launch is small, and so then there is a sense of scarcity.

[00:25:51] Nathan: Right.

[00:25:51] Tyler: And maybe that’s what happened with Mae Fam, is she just launched 500 at a time and just it sold out so quickly that she just kept it, you know, sort of small.

[00:25:59] But that’s also how you really keep a check on quality. Mm-hmm. And you know, I think our audiences have- Been burned by, you know, bad creator-led products where they just slap their name on it, and they’re not really checking quality. So I think the audien- you know, our audiences are very hypersensitive- Yeah

[00:26:17] about like, “Oh, are you putting a good quality product out into the market, or are you just trying to make money off of us?”

[00:26:22] Nathan: Yeah. Something else I’ve seen make a big difference in the quality of the company-

[00:26:27] Tyler: Mm-hmm …

[00:26:27] Nathan: is if you’re selling a either a rec- a recurring product or a repeat purchase.

[00:26:33] Tyler: Okay.

[00:26:33] Nathan: Right? And so if you’re thinking about, you know, you mentioned software.

[00:26:36] Mm-hmm. It’s obviously a recurring purchase. Mm-hmm. There’s plenty of subscriptions, like I think about there’s a author and creator named Sahil Bloom-

[00:26:42] Tyler: Yes.

[00:26:42] Nathan: He’s great … who launched his Wild Roman product, right? It’s not true recurring.

[00:26:46] Tyler: Mm-hmm.

[00:26:47] Nathan: But if it’s a skincare line, you’re like, “If you like it, it’s a repeat purchase,” and then actually they’ll get you on a, a subscription and-

[00:26:53] Tyler: So the, so that is the best model, right?

[00:26:55] So if a buyer is looking at your business, and, and I like to say, like, the gold standard is Mark Rober’s CrunchLab- Yeah … subscription boxes, right?

[00:27:02] Nathan: We, we get it every month.

[00:27:03] Tyler: Right. My six- Is it every month or every three months? Because I think in the beginning it was every three months. Is it every month now?

[00:27:08] Uh, it’s m-

[00:27:08] Nathan: m- my six-year-old puts together a CrunchLabs box every single month. Does he? And he could not be more excited.

[00:27:15] Tyler: Okay. Okay. Yeah. You know, I have a seven-year-old. I need to get that for him because the o- so I don’t let my kids watch YouTube. Mm-hmm. But the only channel he’s allowed to watch is Mark Rober- Yep

[00:27:23] because I know that’s safe, right? Yeah.

[00:27:24] Nathan: Our, our kids, it’s, it’s Mark Rober, Chef Nick, and Dude Perfect. Oh,

[00:27:28] Tyler: okay. Those are the three channels. So ours is Mark Rober- … and Cleo Abram is a little- Oh, yeah, yeah … favorite. We’ve, we’ve just introduced Cleo- Yeah … to him, and he really loves her. Okay. Um, I’m a- I’m actually about to go speak at Open Sauce in July and- Oh, nice

[00:27:40] I told my son, I said, “You know- … the speakers have been invited to Mark Rober’s CrunchLabs.” And he was like, “I need to go.” And so I, I think I might be bringing him. That’s amazing. But, but that’s the sort of like l- intense love and loyalty, right, that Mark Rober-

[00:27:55] Nathan: Mm-hmm …

[00:27:55] Tyler: who I know has probably 50 or 100 people in his R&D lab, right?

[00:28:00] Right. Who, who are, who are thinking of those ideas, who are able to get those customers to come back month after month, and that’s really important for a br- a buyer, like a private equity fund. They’re looking at- What is revenue that will keep occurring every month- Mm-hmm … for us versus, you know, sort of a one-off.

[00:28:20] Nathan: Launch driven. Mm-hmm. The best case scenario is that you have a brand that can be more than that person, right? Right. If they don’t show up to make a video- Sure … that’s still working, and that brand is promoting a product that will, will be purchased over and over again even if the creator doesn’t show up or a video isn’t made.

[00:28:36] Right. Uh, and so then probably the worst case scenario is the, the one-off, launch driven, entirely tied to the creator identity. Is that kind of a two ends of the spectrum?

[00:28:45] Tyler: I, I think so. And, you know, there, and there’s, there’s also a, an importance of naming your products, right? Mm-hmm. You know, I, I, I think … I don’t know.

[00:28:54] You, you get them every month. Is, is Mark Rober’s name on the CrunchBox? The, the CrunchLabs? I, I think it’s CrunchLab is, is the p- It i- The brand. Yeah. Okay.

[00:29:01] Nathan: That’s the brand of the company. They have their own YouTube channels- Yeah … for, for CrunchLabs. It might say by Mark Rober.

[00:29:08] Tyler: Okay.

[00:29:08] Nathan: But I, I feel … Like, as I watch from a distance, you’re like, “Oh, I see what’s happening here.”

[00:29:13] Mm-hmm,

[00:29:13] Tyler: mm-hmm.

[00:29:13] Nathan: It’s not like we’re trying to remove Mark or hide him from it, but you’re like, “Oh, this is its own thing.”

[00:29:17] Tyler: Yes, because we want it to be its own thing. You know, my, my client has, has, um … You know, Caleb Hammer has a, a, um, budgeting app. It’s called DollarWise. Mm-hmm. It’s, it’s standalone name. Mm-hmm.

[00:29:28] Right? Like, we don’t … It’s, it … We specifically, when I was doing the trademark and naming it, we were like, “We don’t want Caleb Hammer in there.”

[00:29:35] Nathan: Right.

[00:29:35] Tyler: You know? And so that’s what buyers want, is they want something that can be standalone, that doesn’t depend on this YouTuber wanting to make videos or not.

[00:29:44] Nathan: Mm-hmm.

[00:29:45] Tyler: And, you know, uh, uh, we, we talked about the key man risk a little bit, so let’s tease it out a little bit more. Yeah. As, you know, when, when private equity funds are looking to buy these, these creator-led businesses, the requirement is that the YouTubers, and I know Veritasium and Matt have both did this, they stayed on for two to three years- Mm-hmm

[00:30:02] to kind of have, have more of a smooth transition. They’re there when, when they hire sort of, um, co-hosts, you know, to kind of wean the audience and teach the audience, “So here are the new hosts, you know, here are the new faces of the channel.” Ideally, the business is so independent, right? It has a full team, executives, right, who are running the company without the creator- Mm-hmm

[00:30:28] right? Who could allow this creator to leave after 12 months or 24 months, and the business would still run really well. I have a f- a five pillar, um, framework for what’s really sustainable in a business, and one of those pillars is the team. Like, who do you… Who’s your team, you know? My favorite phrase that I like to say right now is, “I can raise capital all day long, but the hardest capital to raise for creators is human capital.”

[00:30:52] Mm. Right? Mm-hmm. Like, hiring the right people, bringing in great operators who can run with things on their own. That’s really hard. Um, I mean, I think one thing MrBeast is doing really well is the churn is very high at his company, so it’s like, you know, we’re, we’re getting a, a, you know, like there’s a, a big pool of people now that we can pull from, you know, leaving MrBeast, and so they’re going to all the different companies now.

[00:31:16] I mean, Cody Sanchez is president, was, was- Right … Jimmy’s president. So it’s like, as time goes on, like we’ll get more adults in the room-

[00:31:24] Nathan: Yeah …

[00:31:24] Tyler: for lack of a better word. Now, there are all, a lot of people in corporate America or traditional Hollywood who, who also want to get into this space, who are coming in.

[00:31:33] You know, you look at Dhar Mann’s, uh, you know, president- Mm-hmm … Sean, he was at Discovery. So, you know, there, I think there are a lot of people who are interested and, and supportive of creators who are saying, “I’d like to come help you build.” And that- Mm-hmm … I think is the best s- you know, scenario, is if we can get really ex- you know, experts who’ve been doing this for 20 years who can come in and really help you guide that.

[00:31:55] I mean, I worked in Hollywood for 20 years at the big studios, and so I feel, you know, that I have sort of the expertise, but I have a deep love of creators. You know, I started my own YouTube channel three years ago- Right … because I had a midlife crisis, and I just fell in love with my fellow creators and realized so many of them get taken advantage of, right?

[00:32:13] You know, you, you see these brand deals or these contracts that get presented to creators that you would never see in Hollywood or in corporate America, you know, owning their name and likeness or their formats in perpetuity. But you have young creators who are like, “Oh, my God, someone wants to pay me $5,000 for a video?

[00:32:29] That’s insane,” right? “Here, I’ll sign whatever you want,” and that’s a problem.

[00:32:33] Nathan: And there’s all kinds of details in there that they- Mm-hmm … should never sign.

[00:32:35] Tyler: Sure.

[00:32:36] Nathan: Yeah. Going back to CrunchLabs. Mm-hmm. ‘Cause I, I do think that’s the, the best example- Yes … of a creator business done really, really well. Like, the, the IP is totally unique.

[00:32:44] It has its own brand. The fit, b- like, the, the creator product fit is- perfect. You know, like- Mm-hmm … it, ’cause sometimes you see these products where a creator comes out with that, and you’re like, “Okay.”

[00:32:56] Tyler: Mm.

[00:32:57] Nathan: Any- that’s cool. I think that’ll work. But anyone, any one of these, like, 50 people could have made that product.

[00:33:03] Sure. Sure. Whereas, are there other ones that are at the top of your list where you’re like, “Okay, this was done really well,” or, “This has the potential”? Maybe it’s still early on, but has the potential to be really big.

[00:33:14] Tyler: Um, you know, uh, I did a video about this. So there, there’s this creator called Amanda Rach Lee.

[00:33:20] She’s a- Yeah … bullet journal creator. She’s been making content on YouTube for over 10 years. She started when she was, like, 10. And then I think during COVID, when she was, like, 19 or 20, um, people asked her, you know, “W- why don’t you launch a bullet journal of your own?” And I think for her, it was, there was a hesitation because it’s like, it’s a blank journal.

[00:33:40] Nathan: Right.

[00:33:40] Tyler: Right? But she, she ended up putting her own designs in there. I think each month she did a design for each one. She sold… So it was $50, I know because I bought one. Um, and you know, creators are very transparent, so during that first day when she had the launch, she was showing how many units were being sold.

[00:33:57] Nathan, I think she sold a million units that first day. Right? That’s $50 million.

[00:34:03] Nathan: Yeah.

[00:34:03] Tyler: Yeah. That’s, that’s incredible. But that was a great fit, right? Right. It’s a perfect fit. For 10 years she had been doing journaling- Mm-hmm … writing. Like, there was no better product for her to make than a bullet journal.

[00:34:13] And so now she has a whole line of, like, pens and stickers and everything around that ecosystem. Mm-hmm. Um, another creator, Caroline Girvan, is a fitness creator. Uh, for years, so, so her story was great. So she was a CPA in Ireland, and during COVID, because everybody was locked down, she’s very fit, she’s like, “I’m just gonna do videos at home, and I’m gonna have you guys come along with me.”

[00:34:36] She never did a brand deal. She never made any money. And then I think three years later, she disappeared for six months, and people were like, “Oh my God, where did she go?” Like, “Did she go have a baby? Did she quit YouTube?” Right. And I was like, “I bet she’s building a fitness app.” And sure enough, six months later she, she launched this fitness app.

[00:34:55] It was, like, $20 a month or $99 for the year. Mm-hmm. I bought one ’cause I wanted to support her, and on the bottom, you know, it showed how many members she had, and it was something like 5,000. You know, so if you times 5,000 times 100, you know, like, what is it? Yeah. Half a million- Yeah … that she made on that first day.

[00:35:13] 500,000. Yeah. Right. And, and she has stopped making YouTube videos. Now, that I think is amazing because she has, she used, you know, YouTube as sort of a launchpad. To go and build on her own land. Because that app is hers, right? No one will ever take that away from her. Right. YouTube can’t kick her off. Um, she can do what she, whatever she wants over there.

[00:35:34] And that is what I really want creators to do, is to build on their own land, have their own email list, newsletter. You know, building on different platforms. I mean, there are ones like, there’s Uscreen, there’s TopFan, you know. Yeah. There are ways for you to just be on your own land, where you don’t even really have to be on YouTube anymore.

[00:35:53] I mean, you should still be on YouTube, because YouTube gives you AdSense. And if you’re, if you have the audience there already, you should just diverse all of your- Right … revenue streams.

[00:36:02] Nathan: I wanna get into the, how the AdSense is valued in the back catalog- Mm-hmm … and, and all of that in, in a moment. But I had a creator on, uh, Ben Greenfield, who is big in the fitness space.

[00:36:12] Mm-hmm. And he was telling me how much he has separated his whole Ben Greenfield brand from Kion, which is his supplements brand.

[00:36:20] Tyler: Okay.

[00:36:20] Nathan: Like, early on, he used the Ben Greenfield brand and, you know, like, a top 10 health podcast and all of this- Mm-hmm … to launch Kion and grow to a meaningful scale. But then he’s been very, very deliberate to keep it separate.

[00:36:33] Tyler: Actually, I didn’t even know those were connected. Okay, yeah. I, I know tho- I know them separately- Yeah … but I actually didn’t know they were connected.

[00:36:37] Nathan: So he’s the founder- Okay. Okay … uh, majority owner. Love that. Yeah. You know, he has a team and all of that. But he’s said he’s just watched so many people-

[00:36:45] Tyler: Mm-hmm

[00:36:45] Nathan: see where, you know, either through a, an acquisition or, like, a deal goes south. Um, or actually, well, an example of this that, uh, I was talking to someone else about recently is Mark Sisson with- Mm-hmm. Mm-hmm … um, Primal Kitchen.

[00:36:58] Tyler: Yeah.

[00:36:59] Nathan: Right? Like, textbook perfect exit.

[00:37:01] Tyler: Mm. Mm-hmm.

[00:37:01] Nathan: Incredibly well done. I think it was a $200 million ex- exit to Kraft- Mm-hmm

[00:37:06] in what? 2017 or so- like, it, it was a while ago.

[00:37:09] Tyler: Okay.

[00:37:09] Nathan: Um, but one thing I didn’t realize is that Kraft, through that, because it was so intertangled-

[00:37:14] Tyler: Mm-hmm …

[00:37:14] Nathan: Kraft owns all of Mark Sisson’s, the whole blog. The Mark’s Daily Apple blog-

[00:37:19] Tyler: Oh …

[00:37:19] Nathan: had to be acquired through that.

[00:37:20] Tyler: Interesting. Okay.

[00:37:21] Nathan: And they ultimately ended up shutting d- Kraft looks at it and they go, “We don’t know what content is in here,” and all that.

[00:37:28] Let’s just shut it down.

[00:37:29] Tyler: Oh, well

[00:37:30] Nathan: that’s heartbreaking. And so

[00:37:31] Tyler: because,

[00:37:31] Nathan: because it wasn’t, uh, untangled and wasn’t able to be untangled- Mm … or wasn’t worth it to, you know, a many, many billion dollar company. Then the creator is stuck in this position of like, “Hey, but I want my decade worth of content.”

[00:37:44] Tyler: Well, did he try buying it back?

[00:37:46] Nathan: I’m not sure in that case.

[00:37:47] Tyler: Okay.

[00:37:48] Nathan: Um-

[00:37:48] Tyler: So, so this is a great- Yeah … sort of segue that I, I want to highlight. You know, Nathan, when a lot of creators come to me and say, um, “I want an exit-” Mm-hmm … or, “I want an investor,” and I will say, “Why?” And they’re like, “Because I want free cash.”

[00:38:04] Nathan: Mm-hmm.

[00:38:04] Tyler: Right? Because they think it’s free cash.

[00:38:05] And I, and I say, “Okay, but realize when you bring in an investor or a buyer that, you know, you pr- might have started this channel in your bedroom as a teenager, and you’ve never worked in corporate America. You’ve never had a boss.” Right. “But that’s what an investor or a buyer is, right? They’re coming in and telling you how to run your channel, how to make your content, what products to do, what brand deals to take.”

[00:38:27] It’s very, very sobering, and it’s a wake- Mm … you know, it’s, it’s, it’s not something I think creators think about. And then once I tell them that, and I’m like, “You’re making a million, $2 million on your own. You could make-” Right … “$5 million if we, if we set this up properly. Do you need to exit? You know, do you need to sell it?”

[00:38:47] Because there are these stories, right, where they sell- And then the channel or the business is destroyed- Right … or, or, or taken apart. You know, this is one of the bad, you know, nightmare scenario with private equity funds. You know, I, I think… I don’t know if you, you real- y- if you remember this, but in Pretty Woman, like, Richard Gere was a p- private equity- Oh, yeah

[00:39:09] fund guy, and his job was to tear companies apart.

[00:39:12] Nathan: Right.

[00:39:12] Tyler: You know, I think that, that they were… He was trying to acquire this company, and the son was sorta like, “You’re gonna tear my company apart.” Right. And I think a lot of creators and startup founders don’t realize that sometimes this can happen, right?

[00:39:24] This brand or this audience you’ve built maybe doesn’t stay the same anymore. Now, there are things you can do if you’re willing to stay on and, and give it a, a better transition. This is why I think having a l- a good lawyer on your side is very important. Right. Right? You can structure what that next phase of your business looks like.

[00:39:45] If you’re just getting a check and walking away, like, you could very well, like, you know, Mark, Mark’s, uh, you know, f- with, um, Primal Kitchen, like, that could be the cautionary tale. Right.

[00:39:56] Nathan: Yeah, and it might be in that case that you’re totally fine with it, ’cause you’re ready to move on. Yeah. Maybe. And the exit was for $200 million.

[00:40:01] Sure. Or it could be like, “Hey, can I have this, this side thing that doesn’t mean anything to you but means a lot to me?” Something that I’ve seen is people buying back their companies.

[00:40:12] Tyler: Mm-hmm. Mm-hmm.

[00:40:12] Nathan: And so Catherine Lavery, uh, sold her company Best Self, which was a-

[00:40:17] Tyler: Okay …

[00:40:17] Nathan: a journal and, like, conversation cards company.

[00:40:20] Tyler: Mm-hmm.

[00:40:20] Nathan: They had won one of the Shopify Build a Business challenges years ago with, like, Tim Ferriss and Tony Robbins- Nice, nice … and all that. And built a really meaningful company, sold it to private equity. And then two years later, three years later, bought it back for the price of the inventory that was in the warehouse.

[00:40:36] Tyler: Hmm.

[00:40:36] Nathan: So like got this crazy deal to buy it back.

[00:40:38] Tyler: Okay.

[00:40:39] Nathan: Um, another-

[00:40:40] Tyler: Is it because they kind of let it die? Or- Yeah,

[00:40:42] Nathan: it, it-

[00:40:42] Tyler: Okay. Okay.

[00:40:42] Nathan: You know, you got professional managers who came in- Yeah … and said, “We know better.” Yeah. Sure. “All of this.”

[00:40:47] Tyler: Sure.

[00:40:47] Nathan: And then they inflated salary costs. Mm-hmm.

[00:40:50] Tyler: Mm-hmm. And,

[00:40:50] Nathan: um, turns out the scrappy creator-led business was run pretty well.

[00:40:54] Tyler: Yeah.

[00:40:54] Nathan: The other one is J.D. Roth- Okay … who wrote the blog Get Rich Slowly.

[00:40:59] Tyler: Okay.

[00:40:59] Nathan: And he actually did something similar to the Veritasium folks-

[00:41:01] Tyler: Mm-hmm …

[00:41:02] Nathan: where he… You know, this is probably one of the earliest exits in blogging. I wanna say it was sold in, like, 2013 maybe.

[00:41:08] Tyler: Mm-hmm.

[00:41:09] Nathan: He wrote the blog himself for a long time, gradually brought in other editors.

[00:41:12] Sold it, but didn’t tell anyone.

[00:41:13] Tyler: Okay.

[00:41:14] Nathan: And so a full year or more after the sale-

[00:41:17] Tyler: Okay …

[00:41:17] Nathan: he announced like, “Hey, I actually sold the blog.” And people were like, “Oh, it’s gonna be terrible now. This is straight garbage, all of this.” Mm. Like, “I knew it would go downhill.” And he’s like, “I’ve- I sold it a year ago

[00:41:27] Tyler: Ah.

[00:41:27] You

[00:41:27] Nathan: know? And

[00:41:28] Tyler: you guys didn’t

[00:41:28] Nathan: know. And, and you guys had no idea.

[00:41:29] Tyler: Yeah.

[00:41:30] Nathan: But he ended up being able to buy it back a few years later because… Yeah.

[00:41:33] Tyler: So that’s a great point, right? So when, when I structure an M&A deal, I make sure there’s a buyback clause.

[00:41:39] Nathan: Mm.

[00:41:39] Tyler: Because for this exact reason. Because sometimes you don’t know who you’re getting into bed with, right?

[00:41:46] Yeah. Who, who the buyers are. And because it’s all like dating, right? The first few dates are always great. Yes. But you have no idea n- like until a couple years later how it’s really going to play out. So having that buyback is really important because sometimes there are a lot of private equity funds who buy businesses thinking, right, they could, they could do certain things with it.

[00:42:04] Mm-hmm. And then for whatever reason, maybe they can’t or maybe they’re more focused on these other portfolio companies, they just kinda let it languish. And so the creator might go and, you know, travel the world for a year or two- Right … and be like, “Wait, I really miss my company,” right? Mm-hmm. “I miss, you know, my audience.”

[00:42:21] So, you know, having that buyback where you might lose a little bit of money or, or not. You know, like your example about the inventory was a great one. Maybe all that creator needed was to take some time off. Do you know what I mean? Yes. Like, maybe… And because so many creators- You

[00:42:34] Nathan: didn’t need an exit, you needed a sabbatical.

[00:42:35] Tyler: Yes. Like, we hit burnout, and we think, “Well, I can’t make videos anymore.” You know, it, it’s, it’s just hard when you’re on all the time and you’re making… Mm-hmm. You have to make content every single day, and you feel like you can’t take any time off. I… You know, there’s a, there’s a creator named Vanessa Lau.

[00:42:54] Do you know who she is? I don’t. Okay. So she kinda makes content, you know, f- I don’t know, for creators, like, to start their YouTube channel or their Instagram. She actually took a wh- like a whole year off, and, and her channel definitely took a hit. Mm-hmm. And like, you know, like, she lost subscribers, but she has come back, and she, she’s chronicled that journey.

[00:43:13] But it was so important for her to take that time off- Mm-hmm … because she had been basically pushing herself for, like, five years to just make content every single day. And, and her mental health was just, like, destroyed. And she took that year off, and now she’s come back, and it’s been really refreshing to see that her audience came back and- Mm

[00:43:33] picked up where she, she left off. So maybe w- m- something creators can take out of this conversations is maybe it’s okay to take some time off. Like, maybe you don’t need to sell your business. I mean, this isn’t something I’ve said before, but I, it just came- Right … came out organically, but maybe you just need to take some time off

[00:43:49] Nathan: Yeah, and I think knowing that as the creator you have options.

[00:43:51] Tyler: Mm-hmm.

[00:43:52] Nathan: And that the exit may be incredible. If you’re working towards that, great. Yeah. Or it might be, you know, designing a b- a business to keep for a long time. Something that I focus on when I’m building Kit is to build a business that’s set up in such a way so that it’d be really desirable to purchase.

[00:44:07] Tyler: Mm.

[00:44:08] Nathan: Because investors want the same… Like, investors wanna buy really good businesses.

[00:44:11] Tyler: Yeah.

[00:44:12] Nathan: So if you look at what do they value? Uh, recurring revenue- Mm-hmm … a great team in place- Mm … a great, uh, brand, not a lot of key man risk- Sure … you know, all of these things. If you have all of that in place and you’re like, “Oh, I have a perfect business to sell,” guess what?

[00:44:25] You also have the perfect business to keep- Yeah … and to operate. Yeah. And so, you know, view- that- that’s the position that I’ve been in is having acquisition offers and being like, “Okay, that’s amazing. What would you be looking for to make this business better?” And they’re like, “Oh, well, you d- have to fix X, Y, and Z.”

[00:44:38] And I’m like, “Great, thanks. I’m just gonna go fix- Mm-hmm … those things,” because that outside perspective really

[00:44:43] Tyler: helps. Oh, nice.

[00:44:44] Nathan: And then you have a business that-

[00:44:45] Tyler: Okay … you can keep and run for longer. So you use the due diligence, like, you know, to sort of benefit yourself then. I love that, actually. I’ve used it

[00:44:51] Nathan: once for that.

[00:44:51] Tyler: Okay.

[00:44:51] Nathan: Yeah.

[00:44:52] Tyler: Because, you know, the one thing I want to caution creators about is, let’s say you have a buyer come, come to the table and say, “We wanna buy your business.” The creator’s super excited, right? Right. Because maybe it’s 10, 20, $30 million. But what you don’t realize is maybe this buyer, who’s probably a competitor to you, just wants to look at your tech stack and, like, know your code and know, like, your vendors.

[00:45:15] And so one of the cautionary tales I have is please, like, if a buyer says, “Hey, just give us the raw files. Like, we’ll just, we’ll just analyze it ourselves,” please don’t do that. Please have an attorney. I know I’m sort of like a broken record, but especially- Yeah … with an exit, like, please have an attorney guide you.

[00:45:32] Please have a really strong NDA in place- Mm-hmm … you know, that has residuals protection. It has, you know, a non-, um, solicitation, non-circumvent, uh, trade secret protection because you don’t want that. Because some buyers- Right … will come to the table and say, “This is a buy or build situation,” meaning, “We’re gonna take a look at your product, see if we wanna buy it, a- and if we don’t, we’re just gonna go build it ourselves.”

[00:45:58] Right. Like, they’re very honest about it . I’m, I’m actually, like, very surprised. So you have to be so careful- Mm-hmm … that you’re not showing them your, your tech stack, you’re not showing them your vendor list, you’re not showing them the code, for sure.

[00:46:10] Nathan: The thing that I would be most curious about, so if I was coming in to acquire a company-

[00:46:13] Tyler: Yeah

[00:46:13] Nathan: ’cause you’re talking about, like, give me all the ra- raw files. Yeah. What I would most want is I want the cohort retention data-

[00:46:19] Tyler: Mm-hmm …

[00:46:19] Nathan: for your customer base- Yeah … by segment.

[00:46:22] Tyler: Yes.

[00:46:22] Nathan: So if I have that and I know, oh, from, for this product, if someone comes from the YouTube channel, they stay on average for 12 months, or, you know, any of those things.

[00:46:29] Mm-hmm. Like, that is insanely valuable data.

[00:46:32] Tyler: Totally.

[00:46:32] Nathan: And so you’re exactly right. People are like, “Well, they wanna pay me $10 million potentially, so here you go.” Yeah. And you’re just like, you just gave away something that’s so valuable. Mm-hmm. And that person might say, like, “Great, now we’re going to AI code our- Yeah

[00:46:46] own competitor for it,” or whatever else. “But thank you for letting us know that-”

[00:46:51] Tyler: I know … ”

[00:46:51] Nathan: this particular segment of customers is twice as valuable as that segment.”

[00:46:54] Tyler: Exactly. Most creators just aren’t thinking about it. They’re just heads down- You know, making a product, they’re not really business-minded, right?

[00:47:02] Because they’re not thinking about like, well… You know, I, I had a w- I had one client come in and say, “I think we could probably exit at four to, four to $8 million.” And then I ran, you know, the projections and the models, and I looked at the multiples of, you know, I, I did the com- the comparisons against, you know, kind of recent, um, exits in the last 18 months.

[00:47:23] And I was like, “I think we’re closer to a 10 to 20 X here, so we’re probably in the 30 to $40 million range.” And they were just blown away. They still don’t believe me, but I- Yeah … I think that’s the range we’ll end at. And this is why it’s nice to bring in, you know, experts and advisors to tell you, “No, you’re wrong.”

[00:47:43] Because they think like, “Well, I’m only making one or $2 million in, in revenue a year.” Mm-hmm. But like you’re not realizing what the multiples are and what the market is and, and what similar, you know, products to you have just exited at. Um, and that’s where, you know, I, I, because I do this so often, I can run those comps for them.

[00:48:00] Right.

[00:48:00] Nathan: And y- yeah, you’ve seen inside a lot of businesses.

[00:48:02] Tyler: Mm-hmm. Mm-hmm.

[00:48:03] Nathan: How do you recommend that creators think about cashflow versus enterprise value? So building for maybe the, the lifestyle and the savings and investing now-

[00:48:12] Tyler: Mm-hmm …

[00:48:13] Nathan: uh, versus like, oh, I’m just trying to grow the brand and the revenue as high as possible, who cares about profit, so that I can have this big exit?

[00:48:21] Tyler: Do you mean they, they reinvest everything back into the business? Yeah, exactly. Okay. Well, I find most creators do that, right? They, they really do- They do, yeah … they really do put everything back in there. You know, the issue I’m seeing is a lot of creators are not taking salaries for themselves. Which is fine, but realize that buyers are going to calculate that in there, right?

[00:48:41] Because when they acquire, they acquire your business and they have to have a substitute, you know, like a, a replacement- Right … CTO or CEO, they’re gonna have to add in another 2 to $400,000 for that. So like you’re, you’re inflating your numbers by not taking a salary, but buyer- Someone’s gonna see

[00:48:57] Nathan: through it immediately.

[00:48:57] Yeah.

[00:48:57] Tyler: Like buyers- Yeah … are gonna calculate that immediately, right? So your margins are really not as good as you think it is, right? Right. Because you are, are investing everything back in or you’re not taking a salary. Um, so I think some creators, you know, or founders get caught up in that and they’re like…

[00:49:13] And, and it’s fine And I’ve said this to my clients, they’re like, “Well, should we keep some cash, you know, o- on the side? Um, or should we be putting it back into the business?” Mm-hmm. And I say, “I think it’s fine to put it back into the business, because the buyers will understand that.” But hopefully you are taking some money for yourself, because you gotta like, you know, like not just kill yourself.

[00:49:33] Like, because there is… ‘Cause that’s how burnout hap- happens, right? Right. When you’re not taking care of yourselves. I mean, I think as founders we really have to understand that we can only push for so long, right, before we burn out. And if you burn out, that’s when you get to the ki- that kind of desperate point of like, “Oh, I have to sell my business,” or, “I have to exit.”

[00:49:52] Whereas if you maybe were a little slower with your growth… Here, here’s an example. I, I have a client who to- came to me six months ago saying, “Okay, I, I know we’re ap- approaching burnout. We, we hear everything you talk about, you know, on your LinkedIn or your YouTube, so we need, we wanna diversify and launch a product.”

[00:50:10] So we came up with a great product. It was actually sort of like, like a CrunchLab subscription box. Yeah. Like house hacks, you know? Mm-hmm. And um, so they, they went away, and they were like, “Okay, we’re gonna work on it.” And I think three or four months later we talked again, and I was like, “How’s the box going?”

[00:50:24] And they’re like, “We have to put out th- five short videos a day. Like, we don’t have time,” right? And so they’re foregoing, right, their future self- Mm … for this kind of immediate, um- The short term … in- instant gratification. And the thing is, with a lot of creators, they’re addicted to this dopamine hit of like getting the high views, right?

[00:50:44] Getting the AdSense. Mm. So it’s like, it’s hard to wean them off of that hamster wheel of saying, “Well, but if you had a product line,” right? Like a physical product or a technical product, like, that can make up for some of your AdSense, right? Right. Like, maybe you don’t need to put out so many videos, because you’re actually making money over here.

[00:51:00] But that’s the sort of- Get dopamine, you know, like, reduction. I don’t, I don’t know how to solve it.

[00:51:08] Nathan: Right.

[00:51:08] Tyler: You can … I actually, I do know how to solve it. Here’s the solve. You just have to hire an operator to come- Okay … launch that product for you, right? You have to hire, maybe it’s a fractional CO, which, you know, I, I have, uh, access to.

[00:51:20] Or you hire a company that does it. You know, one of my clients is Whaler, and they actually have this company within their umbrella called Moby Ventures. So Moby actually launches physical products for creators. Mm-hmm. Um, Nami, uh, Matcha, which was from your mom, Ashley. I don’t know if you’ve heard of it.

[00:51:39] Yeah. Okay. So that’s b- from Moby, right? And, and, and Ashley just lets them, you know, launch it and, and ship it and, and, and take care of all the customer service for her. So all she has to do is take a, you know, do the marketing, right, and do the videos for it.

[00:51:55] Nathan: Yeah. Yeah, I think seeing those different examples is really helpful, ’cause then creators can say, “Oh, that’s what I want.”

[00:52:00] Mm. Do I want to be totally in it on R&D and the whole process? Mm-hmm. Mm-hmm. And I, and I love operations, and so let me … Maybe I’ll bring the camera behind the scenes and even, you know- Sure … bring the, the audience on that journey. Or others are like, “I want nothing to do with that.” Yeah. “I wanna make the videos, and I want someone else to run the entire company.”

[00:52:18] And it’s very different ways of operating.

[00:52:20] Tyler: I think it’s usually the latter. You know? Yeah. I, I think they love making the videos. They love interacting with their audience. I don’t think they want to be packaging and shipping boxes, right? And I, I don’t want- Yeah … to be doing that. But, you know, I, I think

[00:52:35] Now, but the R&D part, maybe they wanna be involved in that. And I think there are, uh, third party, you know, vendors and, and, and operators out there who can do it. I u- I know Fourthwall does some sort of that. Yeah, they do. Right? And so there are company … Now, creators will say, “Well, I don’t wanna give up that, that revenue.”

[00:52:54] And I said, “Well, but you’ll be making 80% of money that you wouldn’t have been making in the first place. It’s no different than what you pay to your managers for your brand deals.” Mm-hmm. Right? You wouldn’t have gotten the brand deals on your own. So 80% is better than nothing.

[00:53:07] Nathan: Yeah.

[00:53:07] Tyler: Right? And so that, they, they do get caught up in that a little bit too.

[00:53:11] Nathan: Yeah, for sure.

[00:53:12] Tyler: Mm.

[00:53:12] Nathan: One way that I was thinking about the enterprise versus, uh, enterprise value versus cashflow-

[00:53:16] Tyler: Mm-hmm …

[00:53:17] Nathan: is really looking at the creator business and seeing, do you have something that is an acquirable asset? Because you were talking about the, the dopamine hits or the- Yeah … the treadmill of the five reels a day- Mm.

[00:53:28] Mm. Mm … or a week or whatever.

[00:53:29] Tyler: Sure.

[00:53:30] Nathan: Um, and those all may be bringing in short-term money. Yeah. But the moment that YouTube audience disappears, whate- or the moment you stop making them, it’s gone.

[00:53:37] Tyler: Or the algorithm changes.

[00:53:39] Nathan: Right? The algorithm changes.

[00:53:39] Tyler: Yeah.

[00:53:40] Nathan: Yep. And so all of that is- You have to take the day-to-day revenue or the monthly revenue that you’re getting, and either you, like, invest it in, back in the business to make a product, you know, like your subscription box- Mm-hmm

[00:53:54] or whatever else- Mm … that’s going to have enterprise value. Or you need to take a chunk of it out of the business and go put it in the S&P 500 Yeah … you know?

[00:54:03] Tyler: Sure.

[00:54:04] Nathan: And just say, “Look, I don’t have enterprise value that I’m building in this business- Mm-hmm … but I have great cashflow.” Mm-hmm. “And so 30% of the cashflow is going straight into the stock market.”

[00:54:12] Tyler: Yeah. And I have some clients who say, “You know, I wanna take, um, some cash off the table- Mm-hmm … so I can go buy a house or I can do some investments.” And, and so that’s also a good idea, is, is how do you bring in investors? You know, I like investors, um- Who are angel investors, right? Yeah. Bring in people who will give you $100,000.

[00:54:34] That’s a rounding error, you know- Mm-hmm … for, for, for their cash flow. Um, maybe bring in 10. I’m actually structuring this for one of my clients right now. For his app, let’s bring in 10 or 20 at 100,000 each, and they won’t look over your shoulder. They won’t, like, ask you like a private equity fund. Right.

[00:54:50] Like, “Hey, how’s the business? Show me your monthly revenue.” They, they just won’t care, right? They just, they just hope that when you sell one day, that that’ll be worth something.

[00:54:59] Nathan: And- And then they’re probably already a fan of you- Yes, yes, totally … and your product, and they want you to win. Mm-hmm,

[00:55:03] Tyler: mm-hmm.

[00:55:03] Nathan: And before I wanted you to win.

[00:55:05] Tyler: Mm-hmm.

[00:55:06] Nathan: And now I have all of those same feelings, plus I have some upside in it- Sure … which is even better.

[00:55:10] Tyler: Yes, exactly.

[00:55:11] Nathan: Yeah. That’s something actually that I did. You know, so Kit did not have any outside funding-

[00:55:16] Tyler: Okay …

[00:55:16] Nathan: for a very long time.

[00:55:17] Tyler: Okay.

[00:55:18] Nathan: And in 2021, we had an acquisition offer from Spotify.

[00:55:21] Tyler: Okay.

[00:55:21] Nathan: We turned that down.

[00:55:22] Tyler: Okay.

[00:55:23] Nathan: And that then resulted in a bunch of team members being like, “Well, hold on. How do we get liquidity?”

[00:55:28] Tyler: Mm-hmm,

[00:55:28] Nathan: mm-hmm. And so we ran a small secondary transaction.

[00:55:31] Tyler: Okay.

[00:55:31] Nathan: So no primary capital into the business, all secondary, and it ended up being about $6 million- Okay … uh, that came in at a $200 million valuation.

[00:55:40] Tyler: Nice.

[00:55:41] Nathan: And all from founders- Mm-hmm … you know, people that are friends of mine that I respect, you know, like Dharmesh Shah, the CTO of HubSpot- Mm-hmm … you know, and, um, people like that, and we’ve done another round since then. And in hindsight, I would’ve done that much sooner-

[00:55:56] Tyler: Yeah …

[00:55:56] Nathan: because having 20 to 40 people who are in your corner and cheering for you, like it matters.

[00:56:04] Tyler: Who are advisors to you, by the way. Yeah, and they paid for that. Like you can call them. Yeah- … you can call up a- anytime and say, “Hey, like, what should I do here?” That’s so valuable.

[00:56:11] Nathan: So I think, I think of, like, two examples. Mm-hmm. Uh, one is a gentleman named Noah who runs a software business in a totally different space.

[00:56:17] Tyler: Mm-hmm.

[00:56:18] Nathan: But when I have, like, software problems, I, I’m talking to him. Mm-hmm, mm-hmm. And he’s, he’s put a couple million dollars into, into the business and, you know, buying shares from former team members.

[00:56:27] Tyler: That’s

[00:56:27] Nathan: great. Um, another one is James Clear who wrote Atomic Habits, right? He’s-

[00:56:30] Tyler: I’m so glad we’re talking about this ’cause I wanna talk about books, right?

[00:56:33] Yeah. ‘Cause books is big for creators right now. I’m doing several book deals for creators, but I’m a big fan of James. L- tell me, tell me what you wanted to say.

[00:56:40] Nathan: Yeah, so with James-

[00:56:42] Tyler: Mm-hmm …

[00:56:42] Nathan: you know, authors are huge for Kit.

[00:56:44] Tyler: Mm-hmm.

[00:56:44] Nathan: We, at any given time, probably half the New York Times list- Wow … is, has a Kit newsletter.

[00:56:48] Tyler: Mm-hmm.

[00:56:49] Nathan: I feel like we have tons of the space, and we, we dominate the space compared to any of our competitors. But if you were to walk into Barnes & Noble I have had this experience where I’m like, “Oh, kit customer, kit customer” as I’m- Mm-hmm … pointing at books. Mm-hmm. And I’m like feeling, “Oh, this is great. We have so many of them.”

[00:57:03] Mm-hmm. Realized, wait, I can see 1,000 books from where I’m standing, and I can point to five-

[00:57:08] Tyler: Mm-hmm …

[00:57:08] Nathan: 10 that are kit customers. Mm-hmm. Like, okay, we have a tiny fraction of the market.

[00:57:12] Tyler: Mm-hmm.

[00:57:12] Nathan: And so having James as a shareholder, you know, he’s like, “Great. How do we get this person on the platform? How do we make this happen?”

[00:57:19] And it’s different than a paid advisor, ’cause he actually put his money into the business.

[00:57:24] Tyler: But he’s- Well, I love that. Yeah. I lo- that- that’s genius, right, is having fans and customers, you know- Mm-hmm … be on your cap table, be advisors to you. Let’s talk a little bit about books. I love it. I, I, you know, I actually am writing a book m- right now myself.

[00:57:39] It’s called Creator to CEO.

[00:57:40] Nathan: Nice.

[00:57:41] Tyler: Um, and I have an offer from a major publisher. I, I haven’t taken it. I, I don’t know that I wanna go with them, because I do have this fantasy, because I’m an IP attorney and I say to creators- … “You should own your IP,” that I should- … you know, hybrid publish. Yeah. I should self-publish.

[00:57:55] But I also wanna be a, a New York Times bestseller, and I know if you go self-publish, you can’t, you just can’t touch that, right? You ha- like Alex Hormozi will never be on the New York Times- Right … bestselling list, but he has sold a lot of books, right? Yes, he has. Um, so tell me… I, I mean, I, I know you’re supposed to be interviewing me, but like- However

[00:58:12] tell, tell me how creators should be thinking about books, you know? My client Ca- Caleb Hammer is, is writing one right now for Penguin, and I also represent Derral Eves, you know- Mm-hmm … who has, uh, the YouTube formula. I think, um, for myself at least, I think a book maybe will allow me to reach an audience that n- n- maybe mi- might not typically- Right

[00:58:33] see me from YouTube or LinkedIn. Um, how are, how should creators be thinking about books? Like, should they, should they all- Yeah … go write one?

[00:58:40] Nathan: I, I think the books are fantastic because it condenses- Mm … so much exper- experience that you have into something so attainable for 20 bucks.

[00:58:50] Tyler: Sure.

[00:58:50] Nathan: And then it also transfers a huge amount of credibility.

[00:58:52] Right. Right? And so every author that I’ve seen, even if they’re big on social media, you know, and, and all their content, publishing a book- Usually with a traditional publisher- Mm-hmm … puts them into a different category.

[00:59:06] Tyler: Sure. I

[00:59:07] Nathan: actually just did a podcast episode with James Clear and Madeline McIntosh. Uh, I think it dropped just a couple weeks ago.

[00:59:14] Okay. So it’s on the show. So Madeline was the CEO of Penguin Random House US.

[00:59:18] Tyler: Okay.

[00:59:19] Nathan: And she left a couple years ago, and started, along with James Clear and a few others, Author’s Equity-

[00:59:24] Tyler: Okay …

[00:59:25] Nathan: which is, like, their dream publisher.

[00:59:26] Tyler: Okay.

[00:59:27] Nathan: And so on that episode, they break down exactly why they started it- Yeah

[00:59:31] how it’s going, all that. Mm-hmm. And so I signed with them for my book-

[00:59:34] Tyler: Oh,

[00:59:34] Nathan: okay … which is coming out in December.

[00:59:35] Tyler: Oh, congrats.

[00:59:36] Nathan: Thanks. Um, and it’s, it’s a hybrid model where they, you, as the author, you don’t pay anything out of pocket.

[00:59:43] Tyler: Okay.

[00:59:43] Nathan: What happens is you make 70% of all revenue-

[00:59:47] Tyler: Wow …

[00:59:47] Nathan: and, of, uh, sorry, of all profits on the book.

[00:59:49] Um-

[00:59:49] Tyler: So that’s flipped.

[00:59:50] Nathan: And they make 30%,

[00:59:52] Tyler: so it’s flipped. Right, because for traditional, uh, publishers, you only make 30%.

[00:59:55] Nathan: Or less. Yeah. Yeah. Mm-hmm. And so what they’re doing is basically you split all the expenses 50/50. So Author’s Equity will pay for all the costs of cover design, everything else. Design,

[01:00:06] Tyler: okay.

[01:00:07] Nathan: And, and they’re very cost-effective with all of it. And then after that, after those profits, or, sorry, once the book is profitable, then you get the revenue split on it, that 70/30.

[01:00:18] Tyler: Okay.

[01:00:18] Nathan: A lot of people just think about the money-

[01:00:20] Tyler: Mm-hmm …

[01:00:21] Nathan: but they don’t realize, like, all the second-order effects of that.

[01:00:25] Tyler: Mm-hmm.

[01:00:26] Nathan: So for example, Author’s Equity has a better Audible deal than you could get on your own.

[01:00:31] Tyler: Oh, interesting.

[01:00:32] Nathan: I actually have a few friends who have self-published audiobooks- Mm-hmm … that have sold a million copies or more, who have switched that to then sign through Author’s Equity-

[01:00:41] Tyler: Okay …

[01:00:41] Nathan: because they’re making more per copy.

[01:00:43] Tyler: Okay.

[01:00:43] Nathan: But then another thing is no one really can make Amazon ads profitable for books.

[01:00:49] Tyler: Okay. ‘

[01:00:49] Nathan: Cause if you think about it, if I, if I as the author am making $3 per hardcover- And I’m trying to get someone to make a $20 purchase on Amazon to buy the book. Like, I can’t get a return on ad spend that’s enough for that $3 to cover the 20.

[01:01:03] Mm-hmm, mm-hmm.

[01:01:03] Tyler: Like,

[01:01:04] Nathan: that’s never going to happen, so people don’t do it. Author’s Equity has a different model where they will put up all the money for the ad spend.

[01:01:10] Tyler: Hmm. Interesting.

[01:01:11] Nathan: They will take it out of the expenses for the book.

[01:01:15] Tyler: Okay.

[01:01:15] Nathan: And then, you know, because $20 came in, you had maybe $3-

[01:01:19] Tyler: Right …

[01:01:19] Nathan: uh, in actual hard costs-

[01:01:21] Tyler: Right

[01:01:22] Nathan: uh, printing costs. So then of that 17, like you can actually probably get to a positive return on ad spend.

[01:01:27] Tyler: Wow.

[01:01:28] Nathan: And then the profits, maybe there’s only $2-

[01:01:30] Tyler: Mm-hmm …

[01:01:31] Nathan: in profit all the way at the end for that book, and as the author you’re making 70% of that, and it’s not very much. Mm-hmm. But guess what? You just got the book in the hands of readers, and you got paid to do that.

[01:01:41] Tyler: Yeah.

[01:01:42] Nathan: Whereas Penguin or Hachette or whoever- Mm … they’re never gonna become super sophisticated with ad spend.

[01:01:48] Tyler: Totally. So with Author’s Equity, are they able to go into Barnes & Noble?

[01:01:53] Nathan: Yes.

[01:01:53] Tyler: And, and, and so you can get on the bestselling

[01:01:56] Nathan: list? So w- and a good example would be- Okay … Joseph Nguyen wrote the book Don’t Believe Everything You Think.

[01:02:00] Tyler: Mm-hmm.

[01:02:01] Nathan: And he self-published.

[01:02:03] Tyler: Mm-hmm.

[01:02:03] Nathan: Sold over a million copies.

[01:02:04] Tyler: Okay.

[01:02:05] Nathan: And never hit the New York Times list.

[01:02:08] Tyler: Sure.

[01:02:08] Nathan: He should have dominated the New York Times list.

[01:02:10] Tyler: Yeah.

[01:02:10] Nathan: But he’s self-published, so he’s never- Right … going to make it on. So he republished the book with Author’s Equity. Okay. And then spent like 25 weeks on the New York Times list.

[01:02:17] Tyler: Wow.

[01:02:18] Nathan: And he was able to use all of his marketing savvy. Like, he’s a genius when it comes to, uh, BookTok- Mm. and TikTok Shop. Mm-hmm. And, you know, all of that to get the book in the right people’s hands, and he actually trained the Author’s Equity team on how to use all of his methods.

[01:02:32] Tyler: Amazing.

[01:02:33] Nathan: Um, and so yeah, he was able to, you know, hit the New York Times list and do everything in that way.

[01:02:39] Tyler: Um, can I get an introduction- Yes … to Author’s Equity? I will introduce you to Madeline and James. I, I w- I would, I would love to talk to them. What is your book called? What is the title?

[01:02:47] Nathan: Yeah, it’s called The Ladders of Wealth.

[01:02:48] Tyler: Okay.

[01:02:48] Nathan: How to Master the Skill of Making Money.

[01:02:50] Tyler: Wow.

[01:02:50] Nathan: Comes out December 8th.

[01:02:51] Tyler: Amazing.

[01:02:52] And is it, does it have sort of a creator focus or no?

[01:02:55] Nathan: Um, it’s like m- an entrepreneurship focus. Oh, okay.

[01:02:58] Tyler: Okay.

[01:02:58] Nathan: Y- Creator is part of that. In The Ladders, I talk about how every, as you move… It’s basically a framework for how you earn more money and build wealth over time, and as you move between the ladders, an audience- Mm-hmm

[01:03:10] is the most valuable thing you could have in that.

[01:03:12] Tyler: Yeah.

[01:03:13] Nathan: This is, you’re like trying to launch a new product, trying to go a new direction.

[01:03:15] Tyler: Mm-hmm.

[01:03:16] Nathan: Um, it’s a whole other thing. So yeah- What- … audience is a chunk of that.

[01:03:19] Tyler: What is your goal for your book? ‘Cause this might be helpful for- Mm … all of creators to think about.

[01:03:24] For me, you know, actually the one goal is like if I can get more speaking. Yeah. Like, if I can speak i- to corporate companies or, or- Mm-hmm … traditional Hollywood studios, I think there, you know, there is a desire for that. But I think that, that gives you a sense of, you know, credibility and expertise, right?

[01:03:40] What is your goal for your book?

[01:03:42] Nathan: Yeah. The, the- Biggest top level goal is I’m trying to write the roadmap that I wish I had as a kid.

[01:03:48] Tyler: Mm. Okay.

[01:03:49] Nathan: Right? Where, you know, 14-year-old me was like, “Okay, how do I-

[01:03:52] Tyler: Mm-hmm. ”

[01:03:53] Nathan: How does even the whole world work?” I’m trying to, to map it out- Sure. Yeah … and be like, “Look, this isn’t a…

[01:03:56] it isn’t luck.” You know, like- Mm-hmm … there is an ac- actual concrete steps you can take. And I wanna get that message to as many people as possible. So it’s kind of a crazy thing, but I wanna sell a million copies of this book.

[01:04:08] Tyler: Okay.

[01:04:09] Nathan: Or r- I actually don’t care about selling a million copies. I care about getting it in the hands of a million readers.

[01:04:14] Tyler: Mm-hmm.

[01:04:15] Nathan: And then if we… Like, everything has to tie back into business in some way.

[01:04:19] Tyler: Okay.

[01:04:20] Nathan: And so I think about the opportunities to grow and promote Kit are packaged in a way that don’t, it doesn’t lend itself to media or podcast tours or things like that, like getting the message out in front of more people.

[01:04:35] Tyler: Mm-hmm.

[01:04:36] Nathan: It’s like if you were to try to go on, um, you know, Good Morning America. Mm-hmm. And you’d be like, “I have a software company.” Mm-hmm. And they’d be like, “Oh, oh, okay?” Mm-hmm,

[01:04:45] Tyler: mm-hmm. ”

[01:04:46] Nathan: Well, we don’t care.”

[01:04:46] Tyler: Yeah.

[01:04:47] Nathan: You know? But if you’re like, “I have a book coming out and it’s about this,” and they’re like, “Okay, great,” you know?

[01:04:51] Yeah. It’s packaged in a way- Yeah … to get the message out there.

[01:04:53] Tyler: Got it.

[01:04:53] Nathan: And it’s a much more approachable thing-

[01:04:55] Tyler: Mm-hmm …

[01:04:55] Nathan: for someone to come into my world.

[01:04:57] Tyler: Mm-hmm.

[01:04:58] Nathan: Um, and so I want the book to do that for Kit. Got it. Because Kit’s a big business. We have over 100,000 active creators on the platform and, and all of that, but we still, we just have the tiniest bit of the market right now.

[01:05:11] Mm. And so it could be way bigger.

[01:05:13] Tyler: Interesting.

[01:05:13] Nathan: And I think that the right book will help get Kit in front of a lot of new audiences.

[01:05:19] Tyler: Yeah, that’s super cool. Yeah. How long did it take for you to write it?

[01:05:23] Nathan: Uh, somewhere between 2 years and 12 years, depending on how you count.

[01:05:28] Tyler: Okay. Um, I’m trying to write this thing in six months, so wish me luck.

[01:05:31] Nathan: I, I think it’s doable. Yeah. I think, I think what I would say on writing a book is write every single day-

[01:05:37] Tyler: Okay …

[01:05:38] Nathan: no matter what. I only finally made progress when I-

[01:05:40] Tyler: Really? …

[01:05:41] Nathan: when I did that.

[01:05:42] Tyler: Like, how, what was your… Like, give me some, some tangible, like, an hour a day, or, like, what, what finally made it work for you?

[01:05:48] Nathan: I would say, like, any amount.

[01:05:50] Tyler: Okay.

[01:05:50] Nathan: Um, you could say 20 minutes.

[01:05:52] Tyler: Okay.

[01:05:53] Nathan: Right? ‘Cause you could always ha- find time for 20 minutes.

[01:05:55] Tyler: Okay.

[01:05:56] Nathan: And I think the, just that relentless progress is really important. Finding a really good editor-

[01:06:01] Tyler: Okay …

[01:06:02] Nathan: makes a big difference.

[01:06:03] Tyler: Do they help with that, or do you-

[01:06:04] Nathan: Yeah. Okay. So actually, Author’s Equity hired…

[01:06:06] The first editor that they… The way that it works is in traditional publishing, the editor who acquires the book also often helps you develop the concept and all of that. Sure,

[01:06:17] Tyler: sure.

[01:06:17] Nathan: Author’s Equity has split those.

[01:06:19] Tyler: Okay.

[01:06:20] Nathan: And so they say, “We love this book.” And Author’s Equity only publishes, I think, like, 20 books a year, so- Okay

[01:06:25] they don’t do a lot.

[01:06:26] Tyler: Okay.

[01:06:26] Nathan: Um, and they have to really believe in the book and the marketing behind it ’cause they’re taking a big risk- Sure … uh, on it. But then what they do is they hire, like, a developmental editor to work with you.

[01:06:40] Tyler: Okay.

[01:06:40] Nathan: And so having those calls every week-

[01:06:42] Tyler: Mm-hmm …

[01:06:43] Nathan: you know, I, accountability, turns out,

[01:06:46] Tyler: helps- Yeah, yeah.

[01:06:46] When, when someone’s gonna ask you, “Hey, how far did you get this week?” “How’d you get?” Right.

[01:06:49] Nathan: And you’re like, “You, you said you’d finish these two chapters.” Did you? And you’re like… And so often for me, it’d, it’d be like the night before- Yes … or the day before, I’d be like, “Oh, I’m gonna call with Zach tomorrow.”

[01:06:59] Tyler: Mm-hmm.

[01:07:00] Nathan: And he’s gonna very nicely ask, “Did you do what you say- Mm-hmm … like, you said you were gonna do?” Mm-hmm. And I’m gonna be like, “No.” And

[01:07:07] Tyler: so then- See, I need that. I need a deadline because, because I, you know, I have, I have my law firm, I have my Creator Arc M&A, I have, you know, all of these things. I’m al- also trying to make content, like the book just…

[01:07:19] And, and my two kids. Right. So the book always, like, just slips through the cracks. Right. So if I have no one sort of like holding me accountable or keeping me on track, I think it’s really hard.

[01:07:29] Nathan: It was the biggest thing for me. Like, I only made progress when I put it as the number one thing.

[01:07:33] Tyler: Okay.

[01:07:33] Nathan: Where I said, “At least 20 minutes of time writing the book.”

[01:07:36] Tyler: Okay. It

[01:07:36] Nathan: has… Like, that’s a non-negotiable for the day.

[01:07:39] Tyler: Okay.

[01:07:39] Nathan: And it sounds terrible, but I was like, “Okay, that’s more important than time with my kids- Mm-hmm … or working on a kit or all that.” Mm-hmm. The truth is, none of those things ended up, like-

[01:07:50] Tyler: Suffering,

[01:07:50] Nathan: right? … suffering.

[01:07:51] Tyler: It’s just the mental game, right?

[01:07:52] Nathan: It was just- Yeah

[01:07:52] what did you put first. Mm-hmm. And then I was like, “Oh, well, I can actually make sure I get the, the 20 minutes of writing in before anyone wakes up or before- Right. Right … whatever else. And often that would be an hour or more. Mm-hmm. Um, but that consistent progress-

[01:08:05] Tyler: Thank you. That’s helpful …

[01:08:06] Nathan: matters a

[01:08:06] Tyler: lot.

[01:08:06] Okay, I’m gonna, I’m gonna do that.

[01:08:07] Nathan: I like it.

[01:08:08] Tyler: Mm-hmm.

[01:08:08] Nathan: Um, okay, the last question that I wanted to ask about on the acquisition side is, you see the back catalog in music- Mm-hmm … be really important.

[01:08:17] Tyler: Yes.

[01:08:18] Nathan: You know, with Justin Bieber and everybody else selling- Mm-hmm … selling their masters, selling their, their catalogs.

[01:08:23] Mm-hmm. Does that matter in YouTube? Or is it really people are looking at, like, what is the channel doing today?

[01:08:31] Tyler: Well, I think there’s certainly that, that can be one revenue stream, right? I, I think a lot of, I, I, I’m putting my clients’, you know, catalogs on Tubi or, you know- Mm-hmm … Netflix. I actually was at Netflix last week, and I met with the executive who did Mark Rober and Jordan Matter’s deal.

[01:08:47] Yeah. And they’re, for Jordan Matter, it’s like I, I lo- I love to share this story. So I was speaking w- uh, in, in, in this group of creator e- experts, and Jordan came and spoke. I, I spoke first, and then Jordan spoke after me, and he was kinda sharing about, you know, his daughter Stylist’s- Mm-hmm … skincare line, right?

[01:09:03] That, like, do you know that story? And the guy’s at

[01:09:05] Nathan: Target and everything else.

[01:09:05] Tyler: Yeah, like that full 40,000. We

[01:09:06] Nathan: actually got to hang out with J- uh, with Jordan in Dubai-

[01:09:09] Tyler: Oh, okay …

[01:09:09] Nathan: a few months ago, so he was lovely.

[01:09:11] Tyler: Yeah. So just, you know, the, the 40,000 p- you know, kids who showed up for her- Mm-hmm … la- product launch, you know, her makeup line.

[01:09:18] So what’s so great about their overall deal on Netflix is, you know, it’s, it’s a moment in time, right? It’s, it’s where a big streamer or studio says, “Okay, YouTubers are clearly important.” Right. “We need to get them on our platform.” And I asked Heather, I said, “Well, why is it important, you know, to have YouTubers on, on the s- on wh- our, our…

[01:09:40] or on Netflix?” And she said, something that was really clarifying was she said, “A lot of parents don’t allow their kids to watch YouTube.”

[01:09:48] Nathan: Right.

[01:09:48] Tyler: Right? I, I don’t w- allow my, my son. Um, but they will let them watch it on Netflix, right? Mm-hmm. ‘Cause it’s safe, right? ‘Cause they, they do curate what, what is o- on there.

[01:09:57] They, they make sure it’s nothing, especially, uh, if it’s, you know, under the parental kids channel.

[01:10:02] Nathan: Yep.

[01:10:02] Tyler: So Jordan Matters, they took 10 of their videos and put it, uh, you know, YouTube videos, right, on a catalog. That show became like number three or four in all of Netflix. Not just in kids, but all of Netflix.

[01:10:19] Yeah. And I was like, “What is that about?” And, and she said, “It’s just wholesome content. You know?” Mm-hmm. “It’s, it’s, it’s a relationship between a father and daughter. It’s, you know, it’s her navigating her teenage years with her friends. You know, she’s very brand safe.” And it introduces a whole audience, right, who has never heard of them because they’re, they’re not on YouTube.

[01:10:40] To go back to your point of like YouTubers who have back catalogs who are brand safe, like could be selling these, you know, catalogs- Right … to a Netflix, to a Tubi, Amazon, Hulu, H- Disney, because they all need content right now, right? Because this is free content basically that they didn’t have to greenlight or, or pay, you know, m- a budget towards.

[01:11:03] And Tubi’s doing this in a big way. Tubi’s also doing original content. You know, Netflix is doing- Yeah … original content. What I say to my clients is, you know, think of your back catalog as just additional revenue. Another thing I like to tell my clients to think about is to have a network of channels, right?

[01:11:20] Okay. So not just your own channel. So, you know, let’s say one of my clients is a, a, a male finance creator. Well, can you have like a female creator? You know? Mm-hmm. Maybe a, a, a, a gay or lesbian creator. You know, like all finance still, right? Yeah. Um, who will capture different parts of the, of the demographic that you’re not capturing.

[01:11:39] It diversifies, you know, the key man risk. Mm-hmm. And for a, a private equity fund or a studio to say, “Oh my God, you have 10 channels?” That’s amazing, right? That’s a business we would wanna acquire.

[01:11:52] Nathan: Well, I think that example is so important. Like any acquirer or, you know, any founder is like, “Well, I see the potential.

[01:11:59] I could go d- go and do these things. Once this is successful, I can go and start those other channels.”

[01:12:04] Tyler: Yeah.

[01:12:04] Nathan: And everyone … You know, the acquirer is like, “Yeah, hypothetically.” And so some friends of mine, uh, built a, uh, virtual assistant staffing company called Belay, and they sold it for, I think it mid … Like 100 million.

[01:12:16] Between 100 to 200 million. Nice. And something that they did is they realized they would be going into these conversations and saying like, “Oh, you can hire a great CEO to replace us.”

[01:12:25] Tyler: Mm-hmm, mm-hmm.

[01:12:26] Nathan: And they’re like, “Wait a second. Why make it a hypothetical?”

[01:12:28] Tyler: Yeah.

[01:12:29] Nathan: And so they hired a great CEO. They trained them.

[01:12:31] They did all of that. Waited 12 months, and that CEO took the company to market and ended up selling it to, you know, to private equity and- For

[01:12:38] Tyler: more?

[01:12:39] Nathan: And all that. I, I think for an amazing acquisition. Okay. Yeah. Like everyone was very, very happy with this.

[01:12:43] Tyler: Okay.

[01:12:43] Nathan: And the owners were just in the background.

[01:12:46] Tyler: Mm-hmm.

[01:12:46] Nathan: And so it wasn’t like, oh, the, you know, the, the private equity folks aren’t thinking Could we hire operators who are just as good as the founding team? Mm-hmm. Or that’s something that’s like, oh, no, there’s a team already in place. And so it’s that same thing of like, okay, can you make the leap from one channel?

[01:13:02] Can you back yourself out of, you know, can you take care of some of these issues beforehand, before the acquirer brings it up?

[01:13:10] Tyler: I think so. And, and some creators are. You know, Jesser is one of my clients, and he has several channels, you know? Mm. And, and I think creators, to reduce their potential path down to burnout They are thinking of having smaller, younger creators come in, you know, who have the drive, you know, who have the sort of the fresh- Right

[01:13:32] you know, eyes on, on content. Because they’ll be bringing in a new group of audience. Mm-hmm. And, and, and sometimes m- some of my clients are going to creators who have maybe 10,000 or 50,000 subscribers already, and then asking to acquire. Right, they’ve proven that you can show up consistently. So, yeah, so they, they acquire their channels.

[01:13:50] Mm-hmm. And then they bring them in as an employee, and then so that channel just becomes part of the network that they have.

[01:13:55] Nathan: Yeah.

[01:13:55] Tyler: So I’m doing this with several clients right now, which I think is really smart, and it’s, it’s … You know, basically you’re, you’re becoming your own studio or, or proper network, you know, like an NBC or like an ABC.

[01:14:08] So.

[01:14:09] Nathan: Yeah.

[01:14:09] Tyler: Mm-hmm.

[01:14:10] Nathan: Yeah, that makes a lot of sense. Well, we could talk all day about- Yes … all of this. Yes. Um, thank you so much for coming on.

[01:14:15] Tyler: Of course.

[01:14:16] Nathan: If people wanna learn more about what you’re doing, follow your channel, all of that, where should they go?

[01:14:22] Tyler: Um, so my handle is thecreatorsattorney, and you can find me on YouTube or LinkedIn.

[01:14:27] I write quite often on LinkedIn. Um, you know, this moment in time, Nathan, is so cool. Like, I just came back from Cannes Film Festival, where I brought my clients, Creator Camp. Mm-hmm. They just announced today, Deadline announced that MT- MK2 acquired all Europe rights for their film. Wow. Do you know about this film, Two Sleepy People?

[01:14:44] Nathan: I don’t know about it.

[01:14:45] Tyler: So they made a film, $100,000, over 100 days. They gave themselves that goal, that they were- Okay, wow … gonna make it 100 days. And- I love

[01:14:53] Nathan: constraints.

[01:14:53] Tyler: Yes.

[01:14:54] Nathan: And that, that’s quite the constraint.

[01:14:54] Tyler: Yes. And so the two creators were, uh, the American Baron and, and Carolyn Grossman, and it’s about two people who work together.

[01:15:04] So it’s like Severance meets Eternal Sunshine of the Spot- Spotless Mind. So it’s two coworkers who work together. Apparently, they take this, like, melatonin, um, gummy that allows them to dream every night that they’re married to each other, but then when they wake up, they totally don’t remember that.

[01:15:20] Nathan: Okay.

[01:15:20] Tyler: And they wanted to go into the theaters, and they just did it. They went to independent theaters and said, “Hey, can we show our films in your theaters?” And they were like, “You’re crazy. You’re not a studio, but sure.” Like, they gave them a goal. “If you can pre-sell every theater at $10,000, we’ll let you do it.”

[01:15:38] Okay. But they did two, and then they did 10, and then so they did several hundred, and they would drive in their RV and actually go show up at- To the showings … every single one- I love that … of these showings. And Kickstarter picked it up. Um, we, you know, they spoke to Adweek back at South By. We took it to, to France.

[01:15:55] We took it to the Cannes Film Festival. And this was their first year, the Creator Summit. And so on stage was Markiplier, you know. Okay, him. He, he had Iron Lung, and Seb, this French creator whose film actually premiered at the Cannes Film F- Film Festival. So, you know, I’ve been talking about this for three years.

[01:16:13] I left Hollywood behind, you know, to come represent and protect these young creators. And This moment is here. You know, when I left Hollywood, so many of my former colleagues said, “Don’t do it.” Right. Like, “It’s a terrible idea.”

[01:16:26] Nathan: You’re taking

[01:16:27] Tyler: this huge risk. “There’s, there’s no money in this space. You’ll be babysitting kids.”

[01:16:30] And now, Nathan, I have three offers from the biggest law firms in Hollywood asking me to bring my book of business in. Right. And I actually said, “I don’t think I need to.” Yeah. “But thank you so much.” You know? And so it’s, it’s q- quite a moment in time for creators. Um, I, I really think it’s, um… You know, I think Colin and Samir said this, you know, this is, uh, the, the era of abundance for creators.

[01:16:55] Mm-hmm. It is. And, um, this is such a lovely conversation. Thank you for having me. I’m, I’m a big fan, you know, of what you’re doing, so thank you.

[01:17:03] Nathan: Yeah. Thank you so much. If you enjoyed this episode on building a valuable YouTube business, one of the best examples I know is Ali Abdaal. He joined me on episode 35, where we break down how he’s scaling his business towards $10 million.

[01:17:16] We get into revenue streams, the team, and how it all can run without him. You’ll see exactly what Tyler described put into practice. Like the video if you enjoyed it. Hit Subscribe on YouTube or wherever you’re listening, and I’ll see you next week.