Dear professional and personal friends that I know and love:

I'm never going to follow up on your ask to "keep me in mind if you hear of anything."

Here's why.

It's my care for you that's causing me to say it. I want to see you successful, but I also don’t want to be someone who sets you up for disappointment. So bear with me.

Two different people I really like a lot said some version of this to me in the last couple of days: “Let me know if you know of any job openings or work opportunities.”

In both cases I probably said “sure” but I'll probably fall down on that.

Put yourself in my shoes for a second. You're imagining that I'm sitting on some curated list of opportunities, pattern-matching them against you. What I actually see is a newsfeed — a blur of lots of random opportunities, in theory aimed at me, but the feed doesn't even do a good job of that.

What are the chances they're going to be relevant for you?

There's a bigger problem underneath that, though. People wildly overestimate how well other people know what they would clearly be good for, and what they're interested in.

Ask yourself: how many times have we actually spoken about work? Have I worked directly with you before? Have I seen your work firsthand, and how long has it been since work even came up?

Do we often discuss the details of the type of work you do and the successful deliverables you had?

One of the people who asked — someone I've known for maybe 15 years — I have a vague sense they're design oriented, but I don't think they've ever specifically been a product manager or a designer in a traditional sense. I know they're community oriented, because they're personable and outgoing and seem to be connected to a lot of people, but I don't think they've specifically had a community job either. Plus, I'm not up to date on what they want going forward. Their resume, if I remembered it, is in the past. I could not write the job description of the thing they're looking for.

Fifteen years, and I've got adjectives, not a role.

That's not a failure on my part, by the way. We interact socially, across communities that are tech and tech adjacent. We know lots of people in common. People just aren't sharing as much as they think they're sharing — and they're certainly not sharing with any specificity that would be helpful for me in identifying the perfect role for them, or writing an email to somebody else as to why they're perfect for this role.

Specificity alone doesn't fix it either. When somebody says, "Hey, do you know anyone at Ramp?" — I don't know. I'm connected to 5,000+ people on LinkedIn, and I don't really know if anyone I know has moved over there. Now, "would you mind taking two minutes to check if you know anyone at Ramp" — that's a finite ask, it's easy, and I'm happy to do it.

Off the top of my head, though? I'm lucky I remember my Social Security number. How and when you package up the ask matters.

Then there's the thing I hate to say, but it's true: being friends with someone does not mean you're comfortable professionally vouching for them. Those are two different things.

Both of these people — if you asked me, I would let them watch my child. 100% yes, without reservation. That is literally the highest trust I could ever bestow on somebody.

Would I stake my reputation that they could effectively launch a field marketing campaign? I literally have no idea if they'd be good at that or if they even want to do that.

I have no more idea if they're good at this than they would have as to whether or not I'm a good VC.

Now, because they know my character, they might believe me to be a good partner to a founder on a board, but if they're being honest, they really couldn't say whether or not my ability to pick investments is any good and whether or not someone should put money with me. I think, because they like me, they assume this to be true, but it's honestly not the same thing.

I know plenty of assholes who are excellent investors from a returns perspective, and I know plenty of excellent ones who never found that big fund-returning winner and couldn't raise another fund.

A third friend bumped into me recently and said they're curious to get back into the tech scene, particularly interested in robotics. Here's what's missing: I have no idea what level of seriousness they're at. If they're not robotics curious enough to have spent time figuring out how a robotics company can use their skills, it's really hard for me to imagine them at the top of anyone's candidate pile — because there are robotics obsessed people out there who are going to make their value add to a robotics company really obvious. Next to them, you look random.

So what actually works?

Show me some insight and professional sharing about your job. Something that makes you seem current, professionally curious, and adept at change — and ideally something that carries a little social proof. For example: "I have a bunch of clients, and the first question they always ask me about implementing AI is X. Here are three reasons that's the wrong question, and what I normally do in my engagements is A and B, and those things ensure a much more effective outcome."

If I read that, I think: this person seems really professionally organized, thoughtful, and focused on client success. That's also pretty insightful, and I'm definitely going to find myself repeating it to others — or sharing it with a portfolio company. All of a sudden you've gone from "I have some vague notion of what they do" to "if I introduce them to somebody, that person is going to have a really thoughtful, engaging conversation and be glad they got the introduction, regardless of fit."

The assumption is that you have to brag. That's not it.

What you're really doing is sharing what you've learned, which is the opposite of bragging. It says: whatever gaps I have in my knowledge, I am constantly in a process of filling them, and I fill them by connecting to other smart people. I would much rather introduce that person than somebody who tells me they won a bunch of awards or scored a bunch of new clients — because I still don't understand why that's happening.

People have confidence in the method.

It's this exact shift that we hope to convey in our Visible Work course, which we're filling the remaining seats for this week. It's not just that social media bragging is cringy. It just isn't useful. If you want to work with awesome people, you have to figure out the most effective thing to give to your network in order for someone to make a connection between you and some cool opportunity.

You might be thinking: sure, that works if you have an audience, but nobody reads my posts. It doesn't matter if nobody reads your posts, because everybody has something of a network. If you've been working professionally for over a decade, you can't tell me there aren't 50 or 100 people that, if you bumped into them, you wouldn't say, "hey, keep me in mind for x."

Start there.

An update newsletter with a thing you learned, sent to 100 people — anybody can do that. It has nothing to do with posting on LinkedIn or trying to go viral. Just don't bother asking anybody to keep you in mind if you're not giving them the right information to be effective about it.

The sharing replaces the asking, because if you share, you're going to generate inbound. Send me something concrete that I can forward to specific people — where I get to say, here is my wonderful friend, here is a thing that is going to make you think, here is another way of looking at a problem you almost certainly have, and I'm happy to make an introduction.

That is what I would love from you.

I really do want to be helpful.

“A phantom in a box, shadow in your head.” — White Zombie

Nobody ever asked for VCs to start quoting song lyrics—but if you’re going to, it might as well be someone happily partnered for 20+ years, a longtime vegan and animal welfare advocate, and known for being professional and kind to crews and fans.

Rob Zombie > Kanye

People are usually surprised to find out I'm a Rob Zombie guy. I’ve seen him live, as well as Marilyn Manson, and Rammstein. That's not the expected profile of someone who writes about pitches and startup boards. It's exactly that kind of detail, by the way, that gets strangers to write to you. Nobody ever sent me a personal note because I'm a VC. They send notes because of the specific, slightly off-profile human things I put out into the world.

The quote is from “More Human Than Human” which is the corporate slogan of the Tyrell Corporation in Blade Runner, which builds replicants—machines convincing enough to pass as people.

Rob Zombie borrowed a lie about machines pretending to be people. I'm going to use it to say something about people can use machines to be more human.

Two weeks ago, I got a cold email from Earnest Sweat. It opened with "We've never actually met." In the note, he referenced that on October 12, 2016, I did an 8pm video hangout for a group learning about VC, and Earnest was one of the people on that call, trying to break into venture with no idea how.

Ten years later, he's raising his own fund, and he wrote to tell me. We caught up this morning.

How did he know I’d care or reply?

What probably made it safe was twenty years of writing that reads as an invitation instead of an instruction. If I only published one sided, authoritative pieces telling founders what to do, the only thing that invites is disagreement.

Instead, I get a lot of "I've been reading what you've been writing, and I'd like to connect." Earnest knew I coach investors. He knew I'd be receptive before he ever hit send. Ten years of public silence or only reposts of portfolio company funding announcements and he probably never reaches out.

For me, content has always been a means of creating, and more importantly, inviting connection.

Yet, people assume scaling your content with AI (the slop cannon) will do the opposite and make the internet less human.

It’s an issue I’ve thought a lot about as I’ve developed this small quarterly cohort of a handful of folks called Visible Work.

We're about to run another cohort of Visible Work in about a week (we have a couple of slots still open) and I've been forced to think hard about what the thing I'm teaching even is. I know enough not to think of it as “thought leadership”, so I had settled on the idea of making your accomplishments more visible.

Visibility, though, in a world of AI, has begun to feel too much like an attempt at cutting through with more—more posting, more thoughts, more slices and dices. Thanks to AI, we’re drowning in more, and it’s becoming less personal.

I want more human, and better connected, yet somehow in less time.

That’s what I think we’re teaching now—using AI to make it count and have accountability to be intentional about how you connect. It’s about finding the Venn diagram between who and how you’d really like to work and using the tools to get organized and accountable around it.

Here's an example.

For years, I'd send out a personal update to a list of a couple hundred people I curated by hand — it’s something we do as a project in Visible Work.

Replies would come in, and then life would get in the way, and those replies would sink to the bottom of my inbox and disappear. The most meaningful part of the entire exercise, actual humans actually responding, got dropped too often. Now, my AI Chief of Staff captures every reply and holds me to answering them. Yes, the email is mass, but the people who engage with it get more personal interaction than they used to, not less, thanks to AI.

My social media project manager, also an AI construction, caught something worse. I had a draft of that email ready to go, and it pointed out that I never once asked anybody how they were doing. A letter whose entire purpose is staying connected, and I'd written the whole thing about me. That got fixed before it went out. I write content as an invitation to connect — or at least I say I do.

What I learned was that the most human thing, or the ideally human thing, was screening everything against that filter of my values and intentions.

I've stopped trusting myself to be the only screener, rushed by a five year old who can brush her teeth, but still wants me to, using funny voices for the characters on her brushes.

Humanness in AI also comes up when we're building the invite list for our annual 400+ person tech party—an event I’ve been curating since 2008. I ask: who am I not thinking of that should be here? Who are the design people, the people who actually made New York tech what it is, the folks from my inbox and calendar I've engaged with this year who should be there? Someone could say the thoughtfulness isn't really mine if a machine is doing the remembering.

I'd flip that.

The thoughtfulness is knowing that I will forget people — everyone does — and using a tool to make sure I don’t.

Sometimes the connection runs backwards through the machine. Someone I met at a coworking space ages ago — lovely person, but not a super close professional contact — replied to my last update saying her family grabs an off-season Airbnb with a few other families for a weekend — board games, no agenda. That reply turned into a conversation in my own house last night about which families from my daughter's school we'd actually do that with. Now we might do it. A mass email produced an idea for a better friendship in a 1:1 exchange.

Now for the part I can't do yet, but want to.

I lost my dad in December 2024. This past year, a fellow dad I know lost his. I happened to be at a playground next to his building this week and thought, I should see how he's doing. I should just ask him to coffee. The only reason that surfaced was geographic accident.

What I actually want is a screen, or even better, a serendipitous nudge: who in my network just lost a parent? Who just lost their second? Those are conversations I have a lot of thoughts about and continuously deal with, and I would show up for them.

Would I create a WhatsApp group for the other orphans in my network? Maybe. I'd never thought about it before this week — the idea came out of talking it through with Claude by voice while my daughter climbed some monkey bars quite independently and without help, as she prefers.

That’s another hack we talk about in Visible Work—time shifting. No one has time to sit down and write against a blank screen, but a voice chat with an AI? I’ve done it at midnight on the way back from Beer League ice hockey games—reclaiming otherwise lost time to do things that connect me better and yes, make me more visible.

Here's what gets me: the platforms have this data. Facebook knows. Instagram will show you the post, and then there's no next step, no way to act on it. I'd argue Meta is even incentivized to build it — if Instagram said, “Hey, this is the 4th person in your network to lose a second parent, as you have—would you consider creating a WhatsApp group for them?

I would engage with that support group for years—and I’d certainly rather be doing that than leaving angry comments on Bruce Blakeman posts, none of which I asked for, but some Meta PM decided I needed to make their dashboard look better. Rage got them a few clicks before I ultimately blocked him for my own good, but the Parentless group would have kept me for a decade.

They build the rage machine anyway, probably because the median Meta product manager probably hasn't buried a parent yet, and tech generally overindexes for guys who never cried in therapy.

Which brings me back to what Visible Work is actually teaching, because I hope that it’s nothing like what people assume a thought-leadership course would teach. Publish what invites, not publish more. Track who you owe a coffee, not your posting cadence. Measure whether someone replied and whether you replied back, not impressions.

It’s been a work in progress over the two years I’ve been doing them and this time, I want to push these levers even more. Some weeks, the most important "visible work" isn't writing anything — it's the twelve coffees over three weeks that create the conversations worth writing about later.

If you’d like to join a small group of people who have decided to care about who and how they work, and are willing to use some tools to scale things that have a net effect of better connection to humans who can create opportunity, join us at Visible Work to build a connection engine, not a content engine.

In what ways have you used AI to keep you better connected to humans? I’d love to hear your tips. Funny story, but a young VC I know told me she found her dad’s ChatGPT account and it was full of searches that helped him engage in better conversations with his wife and his children.

I’m not crying. You’re crying.

If I handed you the cash equivalent of your vested equity today — two million dollars, or whatever crazy number the last valuation of your company would imply — would you turn around and put all of it back into the current Series D?

Maybe you’d rather spread it out among the three other well-funded competitors who are all doing the same thing—infrastructure for agentic e-commerce or fully automated AI-driven GTM?

If you’re a founder, the amount of money is probably 10x that or more.

Very few people would say yes and nobody would deliberately build the portfolio you're already sitting on.

Maybe the company IPOs big and you feel lucky.

What if it doesn’t? Would you regret not diversifying?

If your equity is options, you don't own anything yet — you own the right to buy something. Converting paper into anything sellable means writing a check. Sometimes a big one. For an early employee, often an engineer, at a company that's marked up a few times, the exercise cost alone can rival a down payment on a house.

Then, there’s taxes.

Exercising ISOs on a company that's appreciated triggers AMT on the spread between your strike and the current 409A — a tax bill on paper you can't yet turn into cash. If the company IPOs, fine, you cover it. If the company drifts and your shares end up worth less than what you paid the IRS for the privilege of owning them, congratulations, you got hammered on a bet that didn't work.

This happens to people. Regularly—and it’s becoming more of an issue as AI defines what the market is looking for in both an employee and a founder.

Take engineering. The engineering role gets redefined every decade. Mathematicians in the fifties. Craftspeople in the seventies, writing elegant systems by hand. Hackers in the eighties who could ship. Architects in the nineties managing complexity. Web generalists in the 2000s moving fast. Specialists in the 2010s, deep in cloud, mobile, SRE.

In the last eighteen months it happened again, faster this time.

The scarce thing right now isn't code. AI does that. It's judgment — what to build, what to kill, what "done" actually means, the ability to see the whole system at once.

Being an IC these days is feeling a lot like being a founder of your own mini-company.

So why not run your own company instead of doubling down on expensive equity someone else controls?

The engineers who got dramatically more valuable in the last two years are the ones who compose systems, not the ones who type fast. The engineer you want at employee #7 today is the same person who could ship a business with a laptop and a Cursor subscription—only before, starting a company came with a lot more risk and overhead.

Plus, managing employees. Ew.

I hear both sides of this constantly. Solo economics have never been better — one strong engineer with good taste can build a cash-flowing company that used to require a team, a round, and eighteen months of management.

Yet, employee #60 at Cursor just bought a boat.

The upside got bigger everywhere at once—and there’s never been more fear that it might all come crashing down.

If the current wave is turning you into someone who could go start their own thing, then the opportunity cost of your position in someone else's company is bigger than it was two years ago. You're taking concentration risk right when you're turning into the person who could walk.

Plus, there's a whole ecosystem of secondary funds, family offices, and syndicates that want to buy private-company shares off early employees and investors. Some are excellent and price fairly. Some are vultures. Most need the company to sign off, which drops the whole thing back on the founder's desk.

If you're that founder: are you going to let people take money off the table? Real tension here. Enabling secondaries keeps good employees from leaving purely for liquidity and admits that a ten-year run to IPO is a big ask. It also sets a price on your own paper, moves your next round negotiation, changes your ISO strike, and messes with the head of every employee who doesn't sell. Not free. Not automatic. Not something to figure out for the first time when a key engineer walks in with a resignation letter and a lawyer.

None of this is Google-able. Situations differ. The tax code punishes bad timing. The wrong move turns money you thought you'd found into money you actually lost.

Sometimes you should sell. Sometimes you shouldn't. If you haven't sat down and figured out what your equity is actually worth, what routes exist to get at any of it, and whether you'd deliberately construct this position from scratch today, you're letting the situation decide for you.

That’s why I'm doing a webinar on secondaries and employee equity with Qapita. Both audiences welcome — engineers who own the paper, and founders deciding what to do about the people who own it.

Wait… what?

You read that right. I haven't sat down and written a newsletter post from scratch all year.

Not one.

Oh, I've published plenty and I stand behind all of it, but none of it started with me at a keyboard and a blank screen—which is how I did it for the first twenty-one years of this publication.

Nowadays, that kind of feels like writing in script using a fountain pen the way I did back in Our Lady of Guadalupe elementary school.

Is this an admission that I’ve been AI slopping you, my loyal readers, this whole time?

Not at all… but what I am doing, I’ll leave it up to you to decide what to call it.

It makes me think of my friend Amanda McGrory. Amanda is a 7x Paralympic medalist that uses a wheelchair, but I’ve heard her say “Let’s walk over there.” I know what she means, obviously… I’ll be walking my slow ass next to her as she valiantly resists the temptation not to just leave me in the dust. The result is what anyone traveling next to her would expect, but she’s using an aide to participate.

The difference here in my “writing” is that you can’t see the aide I’m using to produce this writing—but more and more, you’re probably assuming it’s in there somewhere. For the record, I’ve manually typed all of the em dashes that have appeared in this post up to this point. I’ve been using them for over 20 years and I don’t plan to stop now.

My challenge is that I don’t have a ton of time to write, but I’d like to do more of it, while still making sure what I produce is authentic. I've been writing this newsletter since 2004. There's no fund brand or book brand or coaching brand sitting on top of me. It's just Charlie, and the business of Charlie, no matter who was signing the checks at the time, has run on people recognizing my voice when they see it.

That’s why I produce these posts in a very particular way that I’d like to share with you. I go into it more deeply with the cohort members of my Visible Work thought leadership class and we’ve got a group forming for September, but I’ll just share the post process for now.

First off, writing isn't one thing. It's a stack.

You pick a subject, you figure out what you actually think about it, you get your thoughts in an order that works for the point you’re trying to make and for the reader’s understanding. You turn that into sentences, and then you edit.

Those are different skills and I don't have an edge on all of them. Turning thoughts into sentences is just transcription—and that’s a commodity. I don't transcribe any better than Claude does.

Where people go wrong is where they turn a topic into sentences using AI, attempting to skip a step by outsourcing the thinking and insight. “Give me a post about X” versus, “Here’s what I think about X… it’s a function of A, B, and C, and I don’t think C matters anymore. Help me turn that into a draft.”

In fact, not only do I not skip out on the thinking these days, I double down on it through voice conversation. I used to have to sit down to write—and my sit down time didn’t always come at a time when I had the most energy or enough bandwidth to push my thinking. Sometimes, because it was 2AM, I just pushed through.

Or, it just didn’t get done at all—and the worst post is the one you didn’t write.

Now, I have lots of time to write because I run voice conversations and “Claude interviews” when I’m at the gym or doing other things—like this morning when I was making my daughter’s lunch for camp. The most useful thing AI does for me isn't composition or insight or research. It's that it time-shifts my voice into the hours where I've actually got something to say. I’ll outline something I’m thinking about or a topic and ask Claude to interview me. I’ll specifically tell it to use as “as many of my own words as possible” when it turns the interview into a draft.

That works for me because of how I already think. I speak the words in my head. I sit on a lot of panels and go on a lot of podcasts. I'm often writing what I've said and speaking what I wrote. Talking was never the workaround. It's where the voice—how I write and my style—lived the whole time.

Typing was just the step where I did my own transcription.

Figuring out what I think is different. That's a step where I do have an edge (hopefully).

It's got a second use case I took a while to appreciate, so I wasn’t good at it for a while. My writing could and should be transactional. Monday, I wanted to let my audience know I’m going to a comedy event tonight where I’m on a panel. In this post, I’m letting you know that I’ve got this cohort opening. These are effectively marketing leads that my business needs to generate. I haven’t always tied my writing into these needs very well, but when it works, it works really well. If I can thread the needle through being both informative, interesting, inspiring, AND if I can drive some clicks, everyone wins.

That’s where tying my calendar, tasks, projects and goals into my writing planning using AI has helped a lot. It gives me a sense of my “marketing needs” for the next week or do so I’m not completely starting from scratch on what to write about.

Professional writing should have a job. Done poorly, it sounds salesy and self-promotional. Done right and it can entertain and accomplish a revenue goal. It can get me a VC coaching client, get me noticed for teaching, and it used to put me in front of founders to invest in. If you think of yourself as a company (the company of you, with lead gen demands and a sales funnel) then a lot of what you write is transactional whether you admit it or not. It's hard to sit inside your own head and work out what somebody else would find interesting about you. Most people are bad at that question and a machine is actually pretty decent at it. Asking what your ICP would actually care about can be a game changer.

I won’t say it’s gone perfectly. A friend recently called me out and told me a post didn't sound like me.

What he caught was the language because I didn't do my normal passes—line by line edits where I read it in my head and decide whether I could say that and sound not just human, but Charlie-like.

Why didn’t I do that? Interestingly, it was because the insight I shared wasn't mine to start with. I'd asked a bunch of questions about whether a startup's market size narrative had anything to do with the history of home pregnancy testing, and the through-lines that came back weren't ones I'd have drawn.

Pointing Claude at that product go to market was my idea, but the analysis was largely Claude’s. Perhaps unconsciously, I didn’t do the language pass because it would have felt like stealing ideas that weren’t mine. I was just the muse.

Most of the time, I start with an interview, so the raw material is me before any editing happens.

Here’s how the editing works, like in yesterday’s post about pitching, when I orchestrate a narrative but not all of it is interview driven:

The first draft came back competent, which is the problem with competent. Nothing in it was wrong. I just wouldn't have published a word of it as written.

Initially, it had me sitting in a pitch meeting nodding along "because I'm a professional and also because I'm a little bit of a coward."

Huh? I'm not a coward. Saying it to your face is the entire thing I'm known for as a VC, and it's most of the reason founders take the meeting in the first place. The machine reached for a self-deprecating aside because self-deprecating asides test well I guess, and to get there it made a claim about my character that's the opposite of true.

Once I flipped it, that correction turned into the premise of the whole post. I say it out loud, most VCs won't, and “here's what they're not telling you”.

A few lines later: "I will say a version of it out loud." Nobody talks like that. I don't say "a version of it." That's the sound of a sentence that's been sanded down. I sent it back and asked for a pass on the whole piece, and the AI tell turned out to be sitting in the verbs the entire time. I am not concluding. It is being ranked. You have built a beautiful deck. Every one of those is one contraction away from sounding like a person you know. There was also a paragraph where ninety seconds "holds" three things, and then holds them again, and then holds them a third time.

“Holds” is not a word I have used out loud in my life other than in fantasy baseball.

The bigger pattern took a few rounds to see. It builds up to jokes and I start at them. It wrote "you're brilliant, you're standing in front of me being brilliant, that's not in question" as a cushion before getting to the part where you're going to hire idiots.

Cut.

It wrote a careful escalation, some of your hires will be very good, some will be fine, some of them will be, and I say this with love, absolute idiots, one sentence after I'd already said most people are idiots.

Cut.

Every soft landing it laid down in front of a punchline came out.

It describes jokes instead of telling them, too. Its version of the competitive landscape slide was "four quadrants and you're in the upper right one, which is my favorite quadrant." That's accurate. That's not funny. Mine runs the horizontal axis from Hard like a fork in the eye to easy like Sunday morning, the vertical from Awesome down to shitty, and puts Brad up in the corner with all eight of his checkmarks.

Same observation. One of them is my writing, even though it’s not me writing. Also, no one is ever writing. We’re all typing anyway, but saying I “typed” a newsletter post sounds just as weird as it would for Amanda to say anything other than walking.

Here's the lesson, and it's not the one people expect from a post like this. The draft is not a thing you edit into shape. It's a thing you argue with, and you only get to argue with it if it's specific enough to be wrong.

The best argument in that whole post isn't in the draft anywhere. I read the section on making revenue sound easy, and I typed one sentence back: anything that sounds hard falls out of my top five opportunities out of two thousand in the funnel. That's the actual mechanism. That's why difficulty kills you, and it's not because anybody sat down and decided your business was too hard. It came out of me because there was something in front of me specific enough to react to.

A vague draft gets you nothing. A confident, wrong, specific draft gets you your own opinion in about four seconds.

Claude then wrote my sentence up into four paragraphs and I cut three of them.

I don't have a word for what that is. It isn't writing the way I did it in 2004, and calling it editing undersells the part where the argument comes out of my mouth first. Prompting is the word people use and it covers about four percent of it.

Whatever it is, it's mine when I've fought with it and it isn't when I haven't. The one time I skipped the fight, somebody caught it immediately.

I’ll stick with “writing” for now. After all, it’s taking me the same amount of time.

I’m just not sitting for most of it.

P.S. Here’s that thought leadership cohort again. Hopefully you’ve learned something or enjoyed this post enough where it doesn’t come off as too transactional to share.

“What is all this?”

That's what's running through my head at slide seven of your deck. I'll say it out loud, right to your face, even if most VCs won't. They nod. They write you a nice note on Thursday.

The unedited version in my head is just: “No.”

“No no no no no.”

“What's even happening here?”

“Where's the money?”

You've built a beautiful deck. There's a slide with all the other people doing something that I might find if I Googled "AI sales trainer." Luckily, none of them have any more than three checkmarks next to the eight arbitrary qualities you picked. You? You've got all eight. Good fucking on you, Brad.

Or did you go with the quadrants? Horizontal axis goes from Hard like a fork in the eye to easy like Sunday morning. Vertical axis goes from Awesome down to shitty and there you are, awesome AND easy. Bullseye.

Meanwhile you've yet to answer the only question I care about:

Can I make a shit-ton of money?

That's it. That's the whole meeting. Everything else in that deck is there because someone told you a deck needs eighteen slides and you're a conscientious person who does the assignment.

Here's the part only a VC knows: when your meeting ends, the investor who liked you has to walk into a room with four people who weren't there and describe you in about ninety seconds. That's the actual product of your pitch. Not the deck. The ninety seconds. Ninety seconds is three things: "there's a giant pile of money here," "these guys have figured out how to reach it without heroics," and "this is happening right now and we're either in or we're watching."

So. Money. Is there a lot of it?

Not "the global market for logistics software is $340 billion," which is a number you got out of a Gartner PDF and which means nothing to me, because you're not getting $340 billion, you're getting whatever the fourteen customers who actually have this problem will pay you, and I want to know what that is. Tell me what one customer is worth and how many of them exist.

That's a real number.

I can do arithmetic. I like arithmetic. Give me the arithmetic and I'll do it in my head while you're still talking and I'll get excited without you having to tell me to get excited.

Second thing, the money has to be easy to get. Complexity kills enthusiasm. If I don't understand what you're doing, or if it seems like the customer needs to download eight things before they save a penny, we're done here.

The problem, besides your dumb customers not realizing how awesome you are, is you're going to hire people, and most people are idiots. I’m an idiot. You’re an idiot.

Have you done anything stupid today? Of course you have.

I mean, they’re nice and they'll seem smart when you hire them, but it turns out interviewing well is something idiots have learned how to do, like your idiot dog learning how to play dead.

He’s not aware that he’s acting or even what death is. He just wants a biscuit.

So when you show me a sales motion that needs a twelve-week consultative process run by someone with a domain PhD and a relationship with the CFO, I'm not thinking "sophisticated." I'm thinking: who's doing that in year three? It's not you. In year three you're in a room with your board explaining why the number moved sideways. It's your fifth sales hire, who you haven't met yet, and who's worse than your first four, because that's how hiring works.

The business has to work when normal people who get sucked into internet comments are running it on a normal day.

Founders get this exactly backwards. They perform difficulty on purpose. They think complexity is a moat, so they explain how hard it all is, how many integrations, how deep the workflow goes, how long the deployment takes, and they think I'm hearing "defensible." I'm not hearing defensible. I'm hearing expensive and slow and dependent on a caliber of person you can't hire at scale for the salary you can afford. Complexity isn't a moat when you're twelve people. Complexity is a hiring problem you haven't had yet.

You're not being graded on whether you're smart. You're being graded on whether the money still shows up when someone less smart than you is running the thing.

Now picture the position you've actually put me in, because I don't think founders see this part. I look at something like two thousand companies a year. I invest in five. Five. Your pitch isn't being graded, it's being ranked, and it's being ranked against 1,999 other things, most of which are also good, plenty of which are run by people smarter than both of us.

Almost nothing gets rejected in that process. Things finish fortieth. Fortieth and dead are the same outcome, and they feel identical from where you're sitting, which is why you get the "we're a little early for this" email and learn nothing.

Third thing, and it's short. Is this happening now?

Not "the market is growing at 14% CAGR." Something changed. Something broke, or got cheap, or became legal, or stopped working the way it used to, and because of that a thing that was impossible in 2023 is now merely hard, and there's a window before everybody notices. I want the sense that this train is leaving whether or not I'm on it. That's not urgency theater, it's not "we've got a term sheet from a fund I won't name," which I can smell from across the room and which makes me trust you less, not more. It's just: here's the change, here's why now is different from eighteen months ago, here's what happens to whoever moves first.

If those three things are true and you say them in the first four minutes, I'll sit through your regulatory slide happily. I'll ask you questions about it. I'll look like the most engaged investor you've ever met, because I'm not evaluating you anymore, I'm doing the thing where I imagine jumping into my money bin like Scrooge McDuck.

If those three things aren't true, no slide fixes it. There's no font. There's no narrative arc. There's no coach who can put the eighteen slides in an order that turns a small market into a big one—although there is one who will tell you whether you’ve nailed the first four minutes or not and will be honest with you about it.

So how else do you know whether you've got it or not?

For starters, you can let a bunch of comedians roast you.

No, that's not a euphemism for fundraising. That's Pitch Roast Live, which is what happens when somebody looks at Shark Tank and a comedy roast and decides those two formats belong in the same room. Four founders pitch. Three comedians and a VC take the pitches apart in front of a paying audience. One founder wins. Noah Obstfeld runs it, it's at Caveat on Clinton Street.

I'm the VC on the panel Wednesday night.

Comedians are better at this than investors are, which is the part founders don't see coming. A comedian finds the soft spot in your pitch in about nine seconds, because that is the entire job, and they don't have a fund's worth of reasons to be polite about it. If your business is confusing, they get the laugh on the confusion. If your market is small, they get the laugh on the market.

Noah gave me ten free tickets. Code NEXTNYCVIP at registration, first come, at luma.com/pitchroastaugust.

Bring a founder who needs it more than you do.

Lately I've been down a rabbit hole on the history of the commercialization of home pregnancy testing.

Yes, a guy looking at this market and sharing insights might feel a little bit like Columbus "discovering" a place where people had been living for thousands of years. 🫣 Bear with me.

You're a VC in 1976, two years before the first at-home test hits American shelves. Here's what you almost certainly get wrong.

You size the market as doctor visits and lab assays. That's where testing happens today. The at-home version looks like a convenience play on a fixed pool of demand — a slice of something that already exists.

You assume one test per event, because that's how the clinical model works.
You listen to the experts, and the experts hate it. Physicians called them dangerous. The worry was that women couldn't be trusted to run the test correctly or handle the answer without a doctor in the room.

You look at the product and you're unimpressed. Fifty dollars in today's money. Two hours to a result. A test tube of sheep red blood cells (yes, it was that baaaaaah-d), a dropper, a vial of purified water, and an angled mirror. Eighty percent accurate on a negative.

You pass, because, in addition to the tiny market, WTF? Sheep's blood?

Every one of those objections is reasonable.

Here's what you missed. The thing limiting how many pregnancy tests got run was never how many women needed one. It was that getting one meant a doctor, a specimen, and a week of waiting.

A 1979 analysis said it plainly: testing at home let a woman keep her doctor out of her sex life.

That demand had never had a way to express itself, so it never showed up in anyone's volume data. The friction ate it before it got counted.

By 1990, women were buying multiple pregnancy tests for every live birth--seven by one UK study's findings. By 1987, a third of American women had used one. Then, ovulation tests landed in 1986 and turned a one-shot diagnostic into something people bought every single cycle.

Nobody in a 1976 investment committee was going to price the privacy or convenience market size correctly. Not because they were stupid, but because they never needed it.

That's why I find Dr. Mariam Elgabry's work with Nurfy so fascinating.

Nurfy is an appliance that runs real microbiology cultures on your kitchen counter in under 18 hours, with swappable cartridges for gut, vaginal, skin, and respiratory.

Lab-grade microbiology, no lab.

Gut health is the ovulation test. Somebody with IBS measures, changes something, measures again, and does that for thirty years. UTI and STI are the pregnancy test — one-off, high price tolerance, because when you find out at 9pm that you have a UTI, nobody's confused about what happens next.

If you underwrite this as a sliver of the lab services market, you'll reach the same conclusion as everyone who looked at a mirror-and-test-tube kit in 1978 and saw a novelty.

The market was never small.

It was locked up like CVS deodorant.

“I don’t know, Rob. You’re the f*cking CEO. You tell me.”

The first deal I ever did as a venture investor was to back Rob May, the founder of Backupify, an idea he pulled off a tweet of mine and turned it into a $100+ million exit to a company that then sold for over $1 billion. Rob was constantly checking with his board on where they thought he should go on different decisions. While I'd like to say I was concerned about the direction a bunch of investors who weren't in the day-to-day as much as Rob was would take the company, I was actually just trying to get him to be less of a time suck.

You run the company. The buck stops with you, and everyone else in that room, me included, is just along for the ride. I'm not telling you that to make you feel good. It's how the job actually works, and most founders behave like it isn't true.

There are a hundred decisions to make every quarter, and if you're not the one making them, your board will exert a lot of pressure for you to execute its own ideas for how things should be done. That's not a coup. Somebody has to steer, and whatever space you leave open, somebody fills. Deferring feels like the safe, humble move. It isn't. Every call you punt becomes a call somebody else makes for you, and before long you're running a company that's being shaped by people who show up four times a year.

Now, some boards can legally replace the CEO. They can set your pay. I'm not going to pretend that power isn't real. There's just a wide gap between the power that's written into your docs and the power that ever actually gets used in the room. Think about prorata rights. Your investors technically have them, but if the only term sheet on the table has the Series A taking the whole round, nobody is throwing themselves on the tracks to enforce prorata. They don't have the leverage, and they're not going to blow up the deal to make a point, so they fall in line. Boards are the same. They will not fire a founder who's doing the job over a fight about one hire or one marketing plan, because doing that torches the very thing they're invested in. They need you to win. So the leverage is mostly yours, whether you're using it or not.

None of this means you get to do whatever you want and tell the board to go pound sand. You make the calls, and you owe them clarity, thoughtfulness, and a real explanation of how you got there. You lead, they understand, and you never leave them guessing. Everything else is just working that out across the three decisions that actually run a company: people, product, and how fast you spend money.

People

Most people conversations go sideways because there's no future org chart. Not the org chart you have today, the one you're building toward. When that picture is missing, board members fill the gap with "I think you need a VP of Marketing," and suddenly you're arguing opinions about product led growth.

You shut that down by showing up informed. "I talked to two later-stage founders who do something close to what we do. One builds this team one way, the other does it completely differently. His team skews way more technical than ours, so I'm going with the sales-led version, and here's why." That's an org chart built forward, out of how companies that already made it actually operate. Compare it to the founder who invented one from a low-information seat, or the one who's just duct-taping hires onto whatever problem flared up last month. A board can feel the difference instantly.

Then instrument the thing. "I think you need a product person" doesn't survive five minutes with a founder who can rattle off the top features customers asked for, the promised delivery dates, and the fact that the team is beating every single one. Now you're having an actual conversation about whether the org is performing, instead of trading anecdotes.

Boards also pay attention to who you drag through the door. They get quietly nervous when the company hasn't built a machine that keeps surfacing genuinely impressive people, the kind the board figures it can learn something from, not the kind the board suspects it knows more than. Hiring the best risk-taker in your existing network is a different thing from going out and landing someone so good you're a little surprised they said yes. If you're going to bet on a weird resume, own it, but then come back with "left-field background, and three weeks in they've already blown past everyone who ever held the seat." You don't get the free pass that comes stapled to the Harvard grad. You buy it with results.

That's really the whole game with a board: anything you're doing that they wouldn't expect, you over-explain. Here's the unconventional move, here's exactly how I'm tracking it, here's the early signal that'll tell us if the risk went bad. Do that and the weird decision stops scaring them. It starts reading as proof you're on top of your business.

You can hear it break in real time when it turns into "I don't think Bob's that strong" against "I think Bob's great." Nobody wins that. So move the fight to different ground. Picture this as a 500-person company. Where does Bob sit on that org chart, and is there really nobody more qualified to run that function at that size? If you can't honestly argue Bob belongs on the team you're trying to build, you've got your answer today, and it's grounded in something real instead of a vibe.

Product

Every product conversation should run off a strong North Star, and not because it looks good on a slide. A clear philosophy does your filtering for you. If the whole bet is that this social app should never feel like dating, then any idea that even smells like dating is dead on arrival, and every board member can see that for themselves without you having to knock it down. The question stops being "here's my idea" and becomes "does this fit," which is a much shorter meeting.

The other half is a real product process with a real owner. Plenty of business-minded CEOs will tell you they own product when what they actually do is generate ideas, and the ideas come from whatever they heard on the last enterprise sales call rather than any deliberate product work. Run it that way and you've announced, without meaning to, that anybody's idea counts, board members included, because you've got no system for telling a good idea from a loud one.

Velocity

Velocity is just a word for how fast you spend money, and it's where a board's anxiety is usually legitimate. These are growth investors. They know that if you don't hit escape velocity, there's no next round to raise, and the second you took venture money you signed up for a certain pace. Real thing. The unease when it's not happening fast enough isn't the board being difficult.

You earn room here with early wins. If you're a first-timer, or just not the kind of founder who can wave a hand and summon another round, you need to prove early that your spend turns into growth, before anybody starts murmuring about your burn. It works like a political honeymoon. You build up the popularity first, then spend that mandate on the big, risky proposal, because if you load up the truck on the big bet before you've banked any trust and it doesn't pay off by the midterms, you lose the ability to govern. Show that growth arrives roughly when you said it would, without betting the company to get there, and you've bought yourself room to take bigger swings later.

Get everyone honest about the bar, too. This is knowable. Talk to next-round investors about the deals they actually did and what made it to a partner meeting. Maybe 2x annual growth is a non-starter for your Series A and 5x makes you a lock. Now the whole table is staring at one number everybody already agreed to, and the meeting quietly turns from "go faster" into "okay, how do we clear a bar we've all accepted without doing anything stupid."

Posture matters even when the numbers aren't where you want them. The founders who stay in blocker-removal mode, always digging into why they can't go faster, keep their board's respect. The gun-shy ones lose it in a hurry. Hiring is where you see it most. Ask a founder why sales still isn't working and you'll hear, "we tried to hire someone to run it and it didn't work out." Ask what they learned from the bad hire and how they went about replacing them, and half the time the honest answer is they didn't. They quietly had the founder pour in time they don't have, or they gutted it out with the team they already had. One miss and they stopped hiring for the whole function.

Which is the real tell, and the question I'd leave every founder with: after a mistake, do you move faster or slower? A mistake is supposed to sharpen you. One less thing you'll ever get wrong again. The founders who come out of one accelerating are the ones I want to write checks to. The ones who come out flinching are the ones I start losing sleep over.

You've got more room to drive this than you think you do and nobody's coming to take the wheel…

…Unless you let go of it.

Founders aren’t the only ones under funding pressure. I know because it’s half of what I talk about with my VC coaching clients.

A VC is only as good as their track record. They need to get good deals over the finish line to have a shot at fame and fortune. They also need to get deals out the door for other reasons:

• If you’ve started a new fund, you want to announce a first deal so people know you’re legitimately putting money to work.

• If you’re near the end of a fund’s life, you might want to finish that fund out so you can get the management fees layering in on the next (hopefully bigger) fund.

• If you’re competing with others in your firm, especially for a partner spot, there could be a sense of “What have you done for me lately?”

So while founders are always wondering how they can get checks in the door, it’s not always straightforward how a VC gets one out the door while still maintaining a high bar.

Lowering the bar doesn't make sense in the long term, because pushing a dud through only delays the inevitable black mark later. Bad deals are also a time sink. You need something fast and good, and that won't happen if you passively wait for deals to come to you—especially if you don't work for Benchmark or Sequoia.

Even if you do, it won't happen if you're junior. You need to go out and get something, and you need a carrot to entice the right deal to reveal itself.

Most investors pitch themselves wrong. They think the carrot is money. It isn't. Money is the most commoditized thing in venture. Everyone has it, everyone's offering it, and the best founders know money follows everything else. Announce to the world that you're actively deploying and you'll get an adverse selection problem—a wave of companies who need capital right now, which is not the same as companies worth backing. The good ones aren't sitting around waiting for your term sheet. They're heads-down building, and won't interrupt that to talk to a check.

"Why would someone talk to you if they don't need money?" is probably the most important question a venture professional can ask.

What the best founders actually want is revenue and talent. They know that if they have revenue, driven by top talent, the money takes care of itself. So if you want their attention, don't lead with the thing they already assume they can get. Lead with the thing that's genuinely hard to find.

I was talking with an investor recently about this exact problem: how to shake something loose before a deadline. My suggestion had nothing to do with announcing capital. Go find a top-tier, first non-founder sales hire—someone who's built sales teams before, someone specifically looking for high-growth companies in a particular space. Take that person and signal to a curated group of high-quality pre-seed and seed investors that you know someone exceptional who's out exploring top companies, with strong $1mm+ revenue growth that is mostly founder-led. 

That's going to shake loose more high signal companies than just asking, "Who's raising?"

The last your upstream deal sources want to do is unintentionally hand a one-off firm a head start on a fundraising process that hasn't even started yet. 

Offering top talent changes the ask into an offer, even if a lot of things might need to line up to actually close that hire.

Revenue and sales leads don’t need as many stars to align, because the right customer can always be closed.

This is how I've run an event series called Always Be Closing. Instead of gathering founders to pitch investors, we partner with top-tier companies that could actually buy startup products, everyone from Datadog to ConEd to KPMG, and we ask a very different question: “Who wants to sell into these companies?” It doesn't matter where a founder is in their fundraising. If they've got a product that solves a problem one of these buyers is looking to solve, of course they say yes. We've curated a buyer with real intent, so the founder knows it's a good use of their time. 

That's a carrot. "Come meet capital" is not.

The best part is for the investor who isn't in the most competitive position, whether that's because they're junior or because their fund just isn't a door-opening name. Access to a Fortune 1000 buyer, or to someone who's been there and done that at the early stages of a company that eventually IPO'd, is all the cred you need. Companies at the highest level of competitiveness will take your meeting if you're the one holding those things, even if your fund isn't high on the ladder. The letterhead stops mattering. What you can open the door to starts mattering.

Money doesn't shake deals loose. Specificity does. Go find the buyer, the operator, the talent a great founder actually wants, and become the person who has access to it. The right deals will reveal themselves once you're offering something they can't get everywhere else.

Everybody's figuring out how to prompt an AI right now. Be specific, give it context, tell it exactly what you want and what a good answer looks like, and it gets you there faster.

Founders should be doing the same thing to VCs.

Here's what I mean: The pitches that actually move me aren't the ones where someone walks me through their TAM or tells me how much their customers love them. They're the ones where the founder hands me the test before I've even asked for it.

"Call this hospital's head of supply chain and ask how long it takes to onboard a new vendor. She'll tell you nine months. Then ask what she'd pay to cut that in half."

"Ask any board member in a building less than 100 units whether they feel like they’re getting their money’s worth out of Buildinglink."

That's prompting your VC. You're not asking me to take your word for anything. You're telling me exactly who to call and exactly what they're going to say.

When I make that call and the answer comes back the way you said it would, the whole dynamic shifts. You've just done my diligence for me and handed me the result with the receipt attached. You know your customer well enough to predict what they'll say to a stranger who calls them cold. That's not a pitch skill. That's evidence you've actually been in the field doing the work, which is the thing I'm really trying to figure out in the first place.

Think about what a normal pitch actually is. It's a contest of opinions. You think the market's ready, I'm not sure it is. You think people will pay for this, I've seen ten companies die believing exactly that. So we go back and forth, and the meeting turns into you trying to convince me your read on the world is right and mine is wrong.

Nobody wins that one in a conference room.

The minute you can say "Don't believe me? Here's who to ask," you've taken your own opinion off the table and mine along with it. Now we're both just checking your prediction against what the customer actually says. You made yourself easy to verify, and easy to verify is about the most credible thing a founder can be.

VCs don’t like doing a lot of work when the payoff is unclear, so you have to ask yourself how you can make my work easier.

This only works if the story holds up, obviously. Send me to a customer who gives me a shruggy "yeah, it's been fine" and you've done worse than not sending me at all. Now, I know you either don't really understand your customers or you were hoping I wouldn't bother to check. So, don't point me at answers you haven't already heard with your own ears. The move only works because you did the listening first. You've had the conversation enough times that you can call the response before it happens, instead of crossing your fingers that it goes your way.

Which is the actual point. Prompting your VC isn't a trick for steering diligence. It's just what naturally comes out of a founder who's done the work. The ones who know their market cold don't need me to trust them.

They point me at the truth and get out of the way while I find it.

Some of the best operators I know are terrible in their own board meetings. On the other hand, I know quite a few founders better at smooth talking their boards than they are at actually executing.

That sounds like a contradiction. It isn't. Running the company and running the board meeting are two different skills, and plenty of founders are great at the first and bad at the second. How much that costs you comes down to one thing: how often your investors see you anywhere else.

Some investors are in it with you every week. A standing call, a Friday text thread, a Slack channel they actually read. Some founders want that. Plenty can't stand the idea of investors that far into the day-to-day and keep them boxed into the boardroom on purpose. That's a fine choice. It has a price. The less your investors watch you operate, the more the board meeting becomes the whole story. Box them into that room and the room has to be perfect, because it's all they get.

They don't sit in your standups. They don't see you unblock engineering, talk a key hire off a ledge, or make the call that saves the quarter. If the meeting is all they get, then ninety minutes every six or eight weeks becomes their entire read on how you run the company, even when it has nothing to do with how you actually run the company.

So you can be crushing the job and still lose ground every meeting. The benefit of the doubt. The room to operate. The investor's instinct to back you next round instead of manage you through this one. Losing your investors' confidence in a board meeting is its own problem, and it has very little to do with how the business is doing. It also compounds.

I've watched how a good operator turns bad in that room. Someone asks the hard question: Q4 revenue, when you hit break-even, what CAC payback looks like once you turn spend back on. The founder who knows the business cold pauses. Not because they don't know it. Because they know it too well. They know the real answer depends on five things that aren't settled yet, doubly so before product-market fit or before the go-to-market is predictable, and they won't fake it. So they hedge. In a room that rewards whoever sounds surest, an honest hedge reads as not knowing your own numbers. The most grounded person at the table comes off as the least in control of it.

That pause doesn't stay empty for long. An investor, a board member, the exec who always sounds certain, somebody's confidence rushes in to fill it. Not because anyone's out to get you. Because that's how rooms work. That's the confidence vacuum, and it's how "I lost the room today" becomes "I lost the company" a few reasonable-sounding decisions later.

If you're not good in that room, the first fix isn't to grit your teeth and nail the next meeting. It's to stop asking one meeting to carry everything. Show up more often, in more formats. Send a monthly update good enough that nobody walks in cold. Call your board members one at a time before the meeting so nothing in the room is news. Surprises are what hurt you. Text when a number moves, up or down. Confidence you build a little at a time doesn't blow up over one rough ninety minutes, and the founders who own the room usually did the work before they ever walked into it.

The second fix is to get good in the meeting itself. One of the ways to do that is to get help—bring the amazing people you hired into the room. If your bench can’t wow your investors, you have a bench talent problem. Plus, it’s sometimes easier to critique and coach someone else than it is to coach yourself.

What I don’t meet when I say get good is to fake confidence—for a founder to perform a certainty they don't have. That's how you actually lose the company. You commit to numbers to win a meeting, then burn two quarters explaining why reality didn't cooperate. Bravado fills the vacuum with the wrong thing. Knowing your numbers cold was never about predicting the future. It's being fluent enough in what drives the business that you can sit in the uncertainty without flinching when someone pokes at it. "Fourth quarter revenue depends on X things. Here's the range and the impact on cash. Here's the one input that moves it most. Here's what we're doing this month to tighten it."

That’s actually the most confident thing you can say in that room.

My friend Chris Fenster is joining me for a webinar on this Wednesday, June 24th, at noon ET. Thirty minutes, free: The Confidence Vacuum. Join us.

He's spent eighteen years inside the financials of hundreds of startups at Propeller Industries as a fractional CFO, which means he's watched plenty of excellent operators freeze on the one question they should have owned. He's seen it from the operator's chair as well as CEO of the company. I'll bring the board seat: what losing the room looks like from the other side of the table, and why the founders who keep control are never the loudest ones in it.

We're getting into it. Bring the question you've been dreading.

To the investors reading this: you've sat across from this founder. Sharper than anyone in their own building, somehow can't win the room they're sitting in. I want your stories. Where did you work with a founder who was better at the job than at the board meeting, and what actually turned it around?

Hit reply.

Nobody thinks of the board meeting as the job. It is. The founders who keep their companies are the ones who figured that out before it cost them.

There’s also a book worth checking out on this written by Bred Feld and Matt Blumberg: Startup Boards. It’s the perfect next thing to read after you raise when you’ve read my book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded. :)

The first check I ever wrote into Edward Woodford of ZeroHash went into a company that doesn't exist anymore. He was building an exchange for alternative commodities, futures on markets where some weird regulatory friction had scared everyone else off. My favorite artifact of that world is that it's still illegal to trade onion futures in this country. In the 1950s a couple of guys cornered the onion market, the onion lobby (there was an onion lobby) got Congress to ban the contract, and the ban stuck. Polymarket and the CME can list a future on almost anything now. They still can't touch onions.

Edward had a master's in finance, an MIT stamp that gave him more credibility than either of us should have trusted, and a deep, almost academic conviction that if he could just get the thing licensed, he'd have a business.

He got it licensed. Then he looked up and realized he was about ten years too early.

We talked about this last week on a Founder Unfriendly AMA, and he put it better than I could. He'd treated regulation as a sufficient condition for success when it was only a necessary one. Getting licensed was the whole company in his head. It turned out to be the price of admission to a game he hadn't started playing.

That mistake is the reason ZeroHash exists. The second company was the inversion of the first. ZeroHash doesn't make anyone successful. It lets people become successful more easily. It clears the necessary condition, the regulated part everyone else avoids, and hands you back the rest of the problem, which was always yours to solve. Edward spent two years learning the expensive way that clearing the hard technical bar is not the same as having a company.

He has a name for this now. He calls it the sequence of mountains. You fixate on the one in front of you, get the license, get the product built, get the book out, and you climb it with everything you have. The problem is that there's another mountain behind it, and another behind that, and the discipline almost nobody has is sending someone to start up the next one before you've finished the first.

I spent an hour last week with a founder who's standing on top of the wrong mountain and doesn't know it yet.

He's a designer, twenty-five years making beautiful things for the home at brands you'd recognize. He's building a physical product for the kitchen, in a category everyone assumes is finished, and his version is, objectively, gorgeous. He spent two and a half years and several trips overseas getting it to the point where it can actually be manufactured, which is the real reason a thing like this doesn't already exist. The material he built around is a nightmare to engineer. That same choice is why his economics are better than the incumbents', because it runs in small batches where the conventional approach forces orders in the tens of thousands of identical units. He knows the category cold, every unit volume and every margin. He has patents filed. He has the thing in his hands.

His deck spends slide after slide establishing, beautifully, that he can build the product. The materials, the engineering, the certifications, the accessories, the consumables that turn a one-time purchase into a subscription. Every slide is a flex of competence about the thing he's already extraordinary at.

The thing that actually decides whether he has a company isn't in the deck at all.

He has no idea whether he can reach a customer cost-effectively, because he's never had to. His whole career, the audience was already there. He designed inside brands that had spent decades and fortunes building the channel he plugged into. Now he's starting from zero, the platforms have made virality close to impossible (it's hard enough to get the people who already follow you to see your stuff), and his answer to "how will you reach buyers" is a number in a marketing budget. Not a person who's done it. Not a playbook from a launch like his. A line item. I asked who was going to spend that money, which operator would run the pre-launch capture and the ad flow and the whole motion, and the answer was no one yet.

That's the lesson, and it's the one Edward paid two years for. You climb the mountain that matches who you already are. The markets academic obsesses over the license. The product designer obsesses over the product. Each one climbs the mountain he already knows how to climb and puts off the one he doesn't, the one he keeps promising to hire someone for later. The mountain you put off is almost always the one that decides whether the company lives.

The fix isn't to admire the problem. It's to start up the second mountain now, in parallel, because it takes longer than you think. Years ago a portfolio company of mine, TinyBop, put a grad student on a weekly newsletter of beautiful things for kids, puzzles and games and the stuff their future buyers already loved, and grew it to fifteen thousand obsessed readers before they had a product to sell. When they finally dropped the app, it spiked the App Store on day one, because the audience was already standing there. I have a founder right now building a machine that cuts the production time on high-end wigs by ninety-five percent, a genuinely hard, multi-year build. The reason I have almost no anxiety about her is that over those same years she built an email list of fifty thousand people. She's an eleven out of ten on the question that sinks most hardware founders: when you're ready to release the hounds, who are you releasing them on?

This founder is sitting on the perfect tool for that and treating it like a risk. A presale. If somebody set up the campaign tomorrow off his existing deck and sold fifteen hundred units, that's not a problem to manage. That's the best thing that could happen to the company. It answers, in public and with money, the two questions his deck can't: do people want this, and can this team create demand from a standing start. The product, by then, is the easy part. The audience never is.

None of this is "ideas are cheap, execution is everything." It's narrower than that. Founders keep mistaking the mountain that's hardest for them for the mountain that's hardest for the business, and pour their best years into the first while the second sits there unclimbed.

If you've gotten far enough to put a deck in front of me, you can probably build the thing. The real question is whether you've spent two years climbing the mountain you already knew how to climb.

“I respect you enough to believe that you should have a really high bar for your own personal investment in this. What data has your company provided you that has earned your time, your money and your emotions?”

This is what I’ve started asking founders as a way to give context to my feedback — because it lands better than, “This won’t work” or “I don’t want to back you.” It gets the founder objectively dispassionately assessing whether they’re a good bet—because it makes them take a look about whether their own bet is based on something tangible.

It’s something that has come up a lot from founders who have read my book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded, because they say it makes them feel like they have a lot more work to do than they realized, or they’re not as close to landing an investment as they thought.

When a founder gets discouraged, the instinct is to read it as the universe handing down a ruling — the idea is bad, I'm not good enough, time to fold. Sometimes that's true. More often it's noise: bad data that looks like signal, or real data about the wrong variable. The founders who make it aren't the ones who never get discouraged.

They're the ones who can tell which kind they're looking at.

So before you answer should I stay or should I go, figure out what you're actually discouraged about. There are three main candidates, and the right move is different for each.

Start with your space and the problem you’re working on. This is the easiest one to assess honestly, because it isn't about you. Are meetings easy to get? Are there investors you can name who are actively hunting in your area right now? Or are investors telling you that it’s a graveyard — a place people are too scared to visit anymore. You can answer that without any of it being a referendum on your worth.

A cold space isn't a verdict on you. It just raises your bar on everything else.

Then there's your team, which is where most people flinch. Recruiting is a selection process, not an affirmation process. A genuinely good person wants to see the value in everyone, and I respect that, but at some point you have to pick, and not everyone has the same potential. The bar that matters isn't whether you rate your team highly. It's whether an investor who actually plays in your space would call it top-tier.

That requires knowing your space at a level most founders never reach. Not "we should probably find someone with manufacturing experience." More like: who ran manufacturing at the companies that won, and at the ones that died? What were the team mistakes? Have you talked to those people?

I know a food business that started as a mom-and-pop and brought in a "business guy" to run it. He's one of the sharpest, highest-character people in my professional circle, and he'll tell you himself he was the wrong person for that job. They didn't need a brilliant generalist. They needed someone who understood how a change to a manufacturing process moves a margin. That's not a knock on him. It's a knock on the match — and the gap between those two things is the entire game.

Insiders have an advantage, and you should want one. Grit is evenly distributed. Deep, specific domain expertise is not. A top-tier team is a team of unfair advantages — unique experience, real relationships, knowing the people and the failures firsthand. A skills match is nice. A skills match alone will not overcome a cold space. If you're going to raise venture, you need an outlier score somewhere.

The third thing is the idea, and this is where founders sabotage their own diagnosis. They lead with the product. Here's what I built, here's what it does. The trouble is that when you pitch product-first, the feedback comes back muddled — you got a no, but you can't tell whether it was the idea, an implicit read on your team, or the fact that nobody's excited about the space at all.

So don't lead with the product. Lead with the team and the problem. Here's who we are, here's what we've done, here's the problem we're chasing — how excited would you be to back a team like this to go solve it? If the answer is "I'd love to see what they build" or "I've been looking for someone on that exact problem," you may be in the rare category where someone pays you to go explore before you've even nailed the idea. If it's not, you're on a different track, and that track runs through clarity, proof, and people who back you specifically.

There's a trap here that sinks more founders than any cold space. It's very easy to hear "you're too early, go raise from angels and people who already know you" and file it as a stage problem — we're just early, the idea's good, the team's great. If you can raise on the social capital you've built through your own relationships, keep one thing in front of you: you're cashing in social capital, you're not clearing a VC's bar. You're great to them because of the relationship. You'd be a cold no to a stranger. That's fine. Just don't confuse the two, or you'll spend that money operating like you're on the institutional track when you haven't earned a spot on it.

Now, the part about whether to stay or go. An investor who actually cares about you — and the good ones care about every founder, not just the fundable ones — will sometimes crush a waste of time early. Not cruelly. Early. The pain of realizing you went down a rabbit hole for a few months is nothing next to the slow grind of staying lashed to a sinking ship for years.

The catch is that the same feedback lands completely differently depending on how much you've already bet. I've had spirited, almost funny arguments with founders about how terrible their space is — "yeah, everybody hates this space, but I think there's something here" — and they're totally fine. They've still got the day job. Nothing's been wagered yet. They welcome the pushback. The founder who's over their skis is a different story. Quit the job, spent the money, burned the social capital. Hear the same thing once you're that deep in, and it feels like being told you wasted years.

The most respectful thing anyone can tell you is that your time and emotion deserve a high bar — so what has this idea actually done to clear it? If you can name the signal, good — keep going. If you go quiet, that isn't anyone calling you a failure. That's the evidence answering for itself.

That question matters even more if you're a woman, a founder of color, an older founder — anyone who can't be sure whether the discouragement you're getting is an honest read or bias. The defense works in both directions: make the argument explicit. Honest feedback has reasons you can name. Bias doesn't.

So should you stay or should you go? Stop treating it as a feeling.

It's a reading.

Get honest about which of the three — space, team, idea — is actually the thing holding you back, and ask what signal you've earned the right to keep betting on. If you can't name it yet, that's your answer for now. Not forever. For now.

I can't remember the last time I went through a drive-thru window. I'm not sure I ever have, to be honest. I’ve never had a non-NYC address and I normally walk to the restaurants near me. So when a founder spends the first ten pages of a deck walking me through the suburban drive-up experience for their healthy fast casual concept, I'm sitting there blinking silently, nodding along, thinking: “OK, I guess I'll take your word for it.”

For the vast majority of products, no individual investor in that room is your target customer. You're far more likely to be pitching someone who will never use the thing you've built than someone who intuitively understands what's good about it and what isn't. That's true even on the consumer side. Especially on the consumer side.

A demo used to be proof that you could build—and that meant something. Today, that means less and less when you can vibecode something faster than you can read this essay.

Now, showing the product boils down to "trust me, people are going to love this," you've handed me a coin to flip. Unless it genuinely knocks my socks off—unless I happen, by accident, to be exactly the customer—I've got nothing to go on but vibes.

There are only three things that get you out of that trap.

The first is prior product success. When you’re the team that previously launched X app that grew to a million users in three weeks, then I’ll probably take a chance on you. Funny enough, when tech is moving so fast, that prior success probably means less and less. If your team previously launched a successful DTC brand in 2010, how relevant is that going to be today?

What you really want is traction. People are already using it. They like it. They come back. That's not taste anymore—that's evidence. You've removed me from the equation entirely, which is exactly where I want to be when I'm not the person you're building for.

If you don’t have that yet, show me insight. Don't tell me people want healthier alternatives. Tell me what you discovered about the customer that nobody else saw, and walk me through how you got there. This customer needs a smaller version of this. That one doesn't use half the features and would happily pay for a stripped-down option at a different price point. This segment wants flexibility the incumbents refuse to give them. When you can take me down that path—when I can understand exactly why you built what you built—you're not pitching a product anymore. You're pitching your judgment, and judgment is the thing I'm actually buying.

Judgement also gives me the confidence that when customer preferences change or when you pivot the product, that you’ll make the right call.

Insight without evidence, though, is just a nicely-worded opinion. "People want healthy alternatives" isn't an insight, it's a horoscope. What's the data behind it? And can you point to the pattern? Four companies made a version of this same bet in adjacent markets and it worked—here's why we're the ones to do it in this one. That's called plausibility and it’s the difference between a founder who's theorizing and a founder who's been paying attention.

We're now in a world where a team that doesn't like its growth numbers can rebuild the entire product over a weekend. AI-driven coding means whatever you're demoing today might not survive the month. By the time I'd see real results, half of it could be torn down and rebuilt twice.

So the product you put in front of me isn't a prediction. It's a rearview mirror. It tells me where you've been, not where you're going. What I'm actually trying to figure out is whether this team can find product-market fit—whether you understand the customer well enough to keep iterating toward something that works, long after the version in this deck is gone.

That's why pitching me with the demo or a story about features is a losing game. The artifact is temporary. Your taste, your traction, your read on the customer—that's what survives the rewrite.

So stop asking me to vote on your product. I'm not qualified, and even if I were, I'd be voting on something that won't exist in six months. Show me you know who you're building for. Show me you've been right before, or that you're right now.

Everything else is just a guess you built a UI around.

Everyday, throngs of mostly junior investors join deal flow calls--regularly scheduled check-ins to "compare notes" on what's out there and being considered.

It's a careful dance. You want good deals back, but you don't want to give away most of your good stuff. You're saving that for better firms than who you're on the Zoom with now.

But wait... Do they think you're the better firm or do they think they are? Are you getting their best stuff or are they just trying to tease you out of yours?

What if you share something you like and they neg it, or worse, they've already passed on it? Are you going to be in your head about it now and suffer from a loss of enthusiasm?

My personal opinion is that these calls are a colossal waste of time--and it's one of the aspects of the job that I hope AI eliminates. Tools like Harmonic allow VCs to search the universe of founders faster and more directly to fill their pipeline. I also think we'll see a lot of movement in better, more informed CRMs where these tools get to know more about what we're looking for, enabling higher signal intros and sharing directly to the handful of investors who care about this one specific thesis.

Instead, I think junior investors need to develop taste and sharpen their judgement if they're going to be valuable contributors to their firm—or even developing visible expertise so that they’re able to source founders first, before others. If you can get someone to seek you out for your feedback before they seek you out for a check, that’s a superpower.

(Note, this is something I help early/mid career and aspiring VCs think through in my coaching practice.)

So what should they be doing when they connect with others?

How about sharing ideas, not deals?

It might not lead to fuller pipelines, but could it lead you to that one insight that turns into your best deal.

Any agent can shuttle bulk company data around and screen for rightness of fit, leaving you more time to meet with thoughtful people--not just investors, but operators, buyers, designers, educators, researches and ask what they believe about where value is being created, what the true nature of problems are, and what problems are around the corner.

If everyone had a better view of what bottlenecks everyone hits next, it wouldn't be that hard to surface who is working on it.

How much of your time do you or people on your team spend learning from others unrelated to a specific in process deal?

When's the last time a conversation with a peer sharpened your thinking? Gave you better pattern recognition? What meetings make you faster and more convicted for when the right deal finally shows up.

The other problem with deal sharing calls and meetups is that even when you trust the person sharing, the signal is still weak. 

Deals in the consideration phase are not deals. They're hypothetical interest. The only meaningful signal is a professional investor who has actually committed. Everything else is hand-waving.

Why do we keep scheduling these calls?

A lot of it comes from how VC networking actually works in practice, especially for junior people and smaller funds. Nobody gets structured training on how to build relationships in this industry. We hire hustlers, send them out to "network", and deals become the default common currency. Deals are concrete, shareable, and make you sound plugged in. Adding them to a pipeline looks and feels like work. 

It's something you can show to GPs--who probably wouldn't think highly of their team if the answer to what they've been doing all day is, "Thinking about what comes next." In what ways do you reward better thinking at your firm versus more pipeline adding?

The 25 most knowledgeable people about a specific domain is a mix of experienced operators, early employees at relevant companies, potential customers, and yes, some investors. There's no version of reality where all 25 of the best people to push your thinking to are all VCs. 

So why are other investors such a disproportionate percent of our calendars after founders?

The logic is that someone with hundreds of deals in their CRM must be a more efficient path to finding one you actually want to do. It isn't. It's just a bigger haystack. If you want to know which enterprise security product is quietly changing how buyers behave, the person who can actually tell you is probably an enterprise security buyer — not someone who's been pitched by fifty companies trying to sell to enterprise security buyers.

Let's stop pulling rabbits out of hats for each other and spend more time debating what makes for good magic or where magic goes from here.

Catch my episode of “Inside Startup Funding” here (or wherever you eat your podcasts), where I discuss the lessons of my new book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded.

“…In an instant, the thing exploded into gobs and gobs of thingamabobs.

One by one, the thingamabobs became all of the things we know today ...big things, little things and even very complicated things.

Everything was in its place. Well, everything except for one small, shapeless thingamabob.

No one knew what it was.

And no one was clear what it was for.”

Feels like how some founders holding on for dear life think about their financial model.

Ask them about whether they’ve even built one and you either get "not yet", because it feels too early, too premature or "yes" because someone told them that they needed one.

Box checked.

Very few founders have a clear sense of what a model should be doing for them at an early stage and what kind of professional input can help them get more out of it. That gap is expensive. Not just financially when it comes to hiring the wrong person— it costs founders the clarity they need to make better decisions, move faster, and walk into investor conversations with something real behind the number they're asking for.

Before you've committed to anything, the first model isn't really a model. It's a sanity check — back-of-the-napkin math on how big this thing needs to get, and how fast, for it to be worth doing at all. What does full-time success look like? What kind of cash flow supports what size team? Is the ceiling high enough to be venture-backable, or is this a lifestyle business, or neither?

Can you even describe what a scaled version of this looks like?

Most founders skip this entirely. They go straight to building, or straight to raising, and never sit with the question of whether the math of the business works in principle. If you're only using this stage to make sure you have enough runway to get started, you're leaving the most important question on the table: is the ceiling on this thing high enough to be worth the effort? Once you can describe what scale looks like, you can start backing into which assumptions have to be true to get there. That's when the model becomes a tool for building, not just a check on your own sanity.

This is where my book, Founder Unfriendly, starts out—helping founders figure out whether their thing is actually a thing, and then quickly getting right into “You've got something — now how fast should you go?”

Once the sanity check passes, the model's next job is to answer a question most founders never actually ask:

“If money weren't the constraint, how fast would you want to grow?”

Not how fast you could grow — how fast you could grow while still making good decisions.

Here's the exercise, taken straight out of the book: Take your current plan and ask: could I go twice as fast without things blowing up? Run the numbers. If yes, do it again — twice as fast as that. Keep going until you hit something uncomfortable. At some point, the model will tell you that you need to hire six salespeople next month, or spend half your budget on paid ads. You'll look at that number and know, viscerally, that you cannot do that well.

That's the constraint.

That's the ceiling on smart growth for this version of the company. Now you know something useful: the number you actually want to raise is the one that gets you to that ceiling — not beyond it.

It also tells you something about the thing you need to figure out—how to raise the ceiling.

This exercise also tells you what your marketing needs are. If the model says you could handle 200 new customers a month operationally, then the question becomes how you generate 200 new customers a month. That dictates where your time goes, where you spend money, what content you produce, who you hire.

The model isn't just financial planning — it's telling you what kind of company you have to become to grow at the rate you want to grow.

Most founders skip this and go straight to the investor conversation, where someone asks "how much do you want to raise?" with no real answer behind it. The doubling exercise is how you get an answer that isn't just a number you pulled from comparable rounds.

Too many founders set their raise it based on some notion of how much they think they can raise, rather than what ask actually makes for the best version of the company at this stage—and the best version of the company is the one that makes for the best pitch. Every company has an optimal amount of fuel — the number that launches the business into orbit with the right trajectory.

It's not always the case that asking for more is harder. Pitching with a worse pitch, because you’re describing a worse version of the company, is harder. Sometimes, the $2M ask makes for a far weaker pitch than the $4M ask, because $4M is the number that funds the hires and the experiments that actually prove the thesis. The exercise of treating money as if it weren't a constraint isn't abstract — it's how you find that number.

Build the plan that makes the most sense, figure out what it costs, and then make the case for it. That's a fundable pitch. Asking for whatever you think you can get is just negotiating against yourself before you've even walked in the room. If you’re not sure how to do that, or you need a gut check, I can help you.

Once you have some signal, maybe some revenue, and potentially a runway deadline coming, the model's job evolves. You're not modeling the business anymore, you're modeling the decisions. When do I need to raise? What do I need to show to raise it? What does burn need to look like to get there? If you're only using the model to avoid running out of money, you'll update it when an investor asks and ignore it the rest of the time.

The more useful version — running it regularly, watching where actuals diverge from plan — turns it into a feedback loop. That variance is data. It's telling you which assumptions were wrong, which bets are paying off, and where to put more resources. The model shouldn't just be tracking what happened. It should be informing what you do next.

When you’ve gotten product-market fit, this is where things get genuinely complicated, and where most finance hiring misfires happen. You've raised money. You're spending it. You think you need someone to help you “track” it. You conflate someone who can close your books accurately with someone who is doing variance analysis, informing hiring decisions, and giving you a window into improving unit economics. If you're only using it to track what already happened — to make sure the books close and the burn rate looks right — you're leaving the actual decision-making value on the table. The question isn't just "are we within budget." It's "which of our bets from last quarter paid off, and what does that tell us about where to put resources next quarter."

As you grow, now you have financial coordination around department heads. You might have multiple revenue streams and cohorts. The model has to translate across the organization — finance talking to the head of growth, talking to the head of sales, talking to you. This is when you need someone who can own the model as a communication tool, not just a math tool. Most founders get here and realize their model doesn't actually reflect how the business works. It reflects how they thought about the business two years ago.

The version of the finance function you need to support this model is directly upstream of the decisions you're trying to make, while founders often treat it as a lagging function. They hire when the mess is already bad—when it’s too much for them to keep track of on their own.

Next week I'm sitting down with Anthony Rosen of Propeller Industries about how to match these needs to humans, titles and org structure. He’s been CFO for 60+ startups across the full arc from pre-launch to $250M+.

If you're a founder who's starting to feel that pull, that sense that your spreadsheets are no longer making sense and something needs to change — come to the conversation before you make the hire. Register here.

The most honest thing you can say about a formal advisor relationship is this:

It's a workaround.

When a founder tells me they need an advisor to open doors in an industry they don't know, or to fill in a knowledge gap they don't have, I hear:

“We don’t know the right people.”

A need for an advisor can be a tell that the network they built before starting their company didn't extend to that industry, or that the relationships they cultivated weren't deep enough to call in that favor for free. Unfair? Maybe. Networks take decades to build and most first-time founders don't have enough of them—but can we just be honest that they’re not a flex?

The best founders I've seen operate don't have "advisors" in the formal sense. They have ten to twenty years of real relationships — people who'll take a call on a Sunday because the relationship is genuine, not because they're vesting monthly into 0.5% of your cap table.

That gap — between the relationship you have and the one you need — is what advisors are supposed to bridge. They can, but you should be clear-eyed about what you're buying and how obvious it is to a funder.

I wrote about this dynamic differently in 2016, in a context that had nothing to do with advisor agreements. A panelist at a startup event told a Black female founder that if she wanted to raise funding, she should hire a white guy to be the face of her business. I had seen this play out firsthand — female founders who brought in a finance type to lend credibility to the meeting. In every single case, the guy detracted from it. He dominated the conversation, cut the founder off, and tried to form some imaginary financing-bro bond with me that didn't exist.

The person I wanted to hear from was the founder and the "advisor" only made her look less confident in her own vision.

The same dynamic plays out in advisory boards, just more slowly and with less drama. You bring someone in because you believe their name, their network, or their domain knowledge will compensate for something you don't have. Sometimes it works. More often, the gap you were trying to fill was really a relationship gap — and a formal agreement with a relative stranger doesn't close a relationship gap.

It just puts it on your cap table.

There's a second version of this mistake that's more subtle. Sometimes a founder finds someone who should actually be working with them — not as an advisor but as a full-time hire or a genuine fractional contributor. They can't afford the salary. So they limit the time, limit the cash, call it an advisory relationship, and hand over equity to make it feel like compensation. These are not the same thing. If the honest answer is that this company would be materially better with this person inside it every week, working on real problems, then an advisor structure isn't a clever workaround — it's a way of avoiding the question. Either you find a way to bring them in properly, or you acknowledge that you're not actually at the stage where you can afford what they'd actually cost, which is useful information. Advisors are not fractional hires without the money. They're a different kind of relationship, and conflating the two is how you end up with someone vesting into your cap table while neither of you is quite sure what they're supposed to be doing.

The advisors who actually help are almost always people founders already have a real relationship with. They know the business. They've seen the founder operate. When the call comes at a bad moment, they pick up anyway.

If that description doesn't fit the person you're thinking of formalizing — if what you really have is two good meetings and a lot of mutual optimism — slow down. Have a few more conversations. Ask them for help before you offer them equity. See if they actually show up.

Real relationships don't require a vesting schedule to activate.

Workarounds are fine. Sometimes they're exactly what you need. Just don't confuse the workaround for the thing itself.

Have more questions about advisors and how to bring them on?

Join our upcoming webinar with our friends from Qapita who specialize in cap table management.

I stopped making new investments out of my fund, but I’m still a gatekeeper of sorts. I run conferences like the Pre-Series A Offsite, VC/Founder Coffee Meetups (like the ones happening next week), and Open Office Hours, where founders are getting intro meetings with investors this week thanks to our tech lawyer friends at Foley Hoag and cap table management software provider Qapita.

Across my twenty years of active investing, I’ve also judged pitch competitions and gone through various other types of applications. I keep seeing two types of founders who are both leaving things on the table, for different reasons.

The first type is openly in stealth. They've told their network they're working on something, they're just not saying what it is yet. I respect the instinct, but it's missed potential.

At least if you wrote "I'm working on something in the logistics space, more soon" that gets your inner network curious about what you're up to. It puts you on the radar of investors who use tools like Harmonic to surface founders by background and signal. If your career history is relevant, you want to be findable before you're ready to fundraise. It opens the door for people in your customer space to reach out unprompted.

None of that requires you to say anything about the product. You're just leaving it on the table.

The second type is a more serious problem. It's the founder whose public profile gives no indication they're working on anything at all — and who is simultaneously applying to things, requesting introductions, trying to get into rooms. I see this constantly. The email is a gmail.com address. The LinkedIn has no mention of any kind of startup. There’s no website for the company — not even a landing page.

That's not stealth. That's confusion. When someone reviews that application, the disconnect between what you're asking for and what your profile shows doesn't read as discretion. It reads as someone who has no idea what kind of competition they’re up against.

The gmail address isn't the problem. The problem is what it signals: You might have thought of this idea today.

A founder who's been heads-down on something for nine months looks identical, in an application, to someone who had the idea in the shower this morning. The gmail address, the blank LinkedIn, the missing domain — they erase the elapsed time.

They make nine months of work invisible.

You can fix this without revealing anything about the product.

I'm not asking for product specs or competitive positioning. I'm asking for a breadcrumb trail that confirms you're a real person who has been working on a real thing. A custom domain email — the kind that costs a couple of dollars — doesn't prove your idea is good, but not having one means you didn't bother to eliminate one way you might be taken as unserious.

That's low-hanging fruit.

The domain doesn't even have to be your company name. If you're building an travel platform using AI, grab travelphds.ai as a working project name. If you have a holding company, use that — and let the history of that entity say something about how long you've been at this.

If your company doesn't have a brand yet, use your own name at a personal domain. That's actually not a bad look, because ultimately you're the one being backed. A blog or a simple profile at your own domain says: I've been thinking about something, here's who I am, here's where this is headed.

I don’t mean you need to become a “thought leader”, the sound of which probably makes you throw up in your mouth a bit.

When people hear "build a public presence," they assume I mean self-promotion. I don't. Self-promotion almost certainly means claiming something beyond what's true or at least putting a sales or influence angle on your story. A landing page or a LinkedIn job listing that says you've been working on this for nine months is just accurate.

A blank profile is actually the distortion — it makes nine months of work look like nothing happened.

Reflecting reality isn't self-promotion. It's just honesty.

You don't have to stake out positions that might age badly. You can be a public student. If you're building a co-op management tool because you serve on a co-op board and the existing software is overbuilt for a 20-unit building, you don't have to announce you're building anything. You can just start talking about what it's like to be a co-op board member. Ask other people how they handle the same problem. Document what you're learning. That's low-risk visibility that still leaves a trail — it shows you've been thinking, you understand the customer, and you're not starting from zero.

The concern I hear sometimes is that any visibility tips off competitors. Notice what I'm actually asking you to make public: who you are, and what problem you've been thinking about. Not what you're building. The former CTO of a defense company working on ethical battlefield AI can say exactly that without revealing a single thing about the product. What it does reveal is who should be talking to that person — and that's the point.

You might not think this is a big deal, especially because the cost of invisibility shows up earliest at the smallest asks. It’s not "you can't raise a Series A." It’s earlier than that. Think about Tech Week in New York — 500 applications for 100 seats at a single event. Some of those connections could genuinely change the trajectory of a company, but the people reviewing those waitlist applications aren't doing deep diligence. They're pattern-matching in seconds. A gmail address doesn't get you through that filter, and the introduction that would have come from that event doesn't happen, and you never know what you missed.

There are VC or customer dinners happening that you don’t know about because no one thinks of you for them when you’re building in secret.

That's the asymmetry. The downside of a minimal public presence — a few dollars on a domain, a LinkedIn profile that reflects what you're actually doing — is nearly zero. The upside is staying in the game on the small opportunities, the ones that don't look important until later. The downside of invisibility compounds quietly. You don't get a rejection notice.

You just don't get asked.

If you've been at this for six months and your profile looks like you might not even be the same person working on it — that's not stealth. That's your work being invisible. Those aren't the same thing.

By the way, if you're building something early and want to think through how to make your work visible in a way that's honest and useful — not performative — that's what Visible Work is for. The next cohort starts on May 18th and we’ve still got a few seats open.

A few months back I got a backchannel reference call about a founder I'd backed. His company hadn't returned anything to investors when it got sold, and I hadn't really heard from him after the sale.

The easy thing — the thing most VCs do — is to say "I haven't heard from him, I don't really know about the new company" and move on.

Instead I called the founder. I figured he probably felt too awkward to tell me about the new thing, and I was right.

We had the conversation that should have happened a year earlier. It was awkward for him — the natural thing after losing someone's money is to disappear, and he had. It was frustrating for me, because the relationship had quietly withered and I'd been letting it. Somewhere in the middle of the call we said the thing out loud: nobody talks about this. There's no template for the post-loss check-in. Everyone's just supposed to figure it out, and most people don't.

We both walked away grateful for having had the conversation. I wound up saying nice things about him for the reference.

That could have been it. Most of these moments end there. But here's where I think I work differently — and it's the thing I'm trying to pass on through the Visible Work cohorts I run:

I wrote about it later that day. (What's Next After You Lose Someone's Money)

It remains one of my most engaged posts in the last year. Lots of people reached out to say thanks for naming something they'd been quietly dealing with and didn't have a good answer to.

It wasn't a contrarian take. It wasn't a framework. It wasn't a term I coined that's about to become the insight of the year. I just shed some light on a thing nobody was saying out loud that lots of people were feeling. I wasn't trying to grow followers. I was trying to be helpful.

Being helpful wound up helping me, too.

You see, I had a book lunch coming up for Founder Unfriendly and I was actively looking for podcasts to join—especially ones that weren’t just successporn about rocket ship revenue growth unattainable to 99% of founders.

A couple of days after the post went up, an email landed:

Charlie,

I host a podcast all about how to design challenging conversations — so that they're more effective and impactful. This seems like a really worthwhile topic for exploration in a live episode — if you're up for recording a conversation in 2026, let me know?

Best,Daniel

That's Daniel Stillman, who runs The Conversation Factory. I said yes immediately — partly because his email was specific in the right way (he'd actually read the post, named exactly what he wanted to talk about), and partly because I was trying to get on more podcasts for the book launch.

We recorded a few weeks later:

That whole sequence — the reference call, the follow-up with the founder, the post, Daniel's email, the recording — is what thought leadership should actually look like: Full of thoughtful conversations that inspire you to find ways to help others.

That’s not how most people describe social media channels these days, but it doesn’t have to be.

You don’t have to be a linkbaiter just to get follows.

Consider that the search for work is the search for utility:

“Will someone pay me to help others in the way that I like helping?”

By modeling the ways that you want to be helpful ahead of the work, you increase the chance of attracting interesting work opportunities. That’s why I’ve held onto this small Visible Work cohort that I started working on a few years ago. Helping someone find the way they want to display their helpfulness and scale their generosity, in ways that leads to more meaningful work, is incredibly rewarding.

We’re running the next Visible Work cohort starting May 18th. It will be about ten of us—people who want to be more visible at work without turning into LinkedIn personalities. You can sign up here.

If you can't think of what to write, the problem usually isn't the writing. It's that you're letting too many interesting conversations pass — or not having enough of them in the first place. You're finding it hard to get inspired to share, because you're not getting inspired enough by others, or you lack the mechanisms to lower the friction to share them when you do.

The good news is the fix is the most enjoyable thing on your list. You don't have to grind out content. You have to call the founder whose app you love. Email back the person who reached out for advice. Have the dinner that's been kicked around the calendar for three months.

The conversations are the work. The writing is just what falls out when you pay attention and build the scaffolding to make sure they don’t get lost.

If you haven’t already, check out my book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded and my new AI fundraising coach and companion guide.

_____

Strava's AI just told me I crushed the NYCRUNS half marathon in Brooklyn with my 1:35. It said I “sustained high intensity throughout with impressive heart rate effort.” I got similar feedback when I ran the NYRR NYC Half.

Not true.

In reality I’m in a slow recovery from from a torn proximal hamstring tendon and I haven’t been able to pinpoint why I just wasn’t running at the speeds I wanted to, despite feeling like I’m in good shape. It felt like I had another gear that I just wasn’t able to shift into.

I took my Strava data from these races, along with peak previous performances on the same course, and uploaded it to Claude with the following prompt:

“I would like you to compare two sets of races on the same course... the Brooklyn Half and the NYC Half. 2026 times are after a torn tendon (ischial tuberosity). Is there any insight you have into what's hindering me in this post-tear recovery?”

A minute later, I had charts, insights and the ability to query it further.

The charts told the story across both races: I ran nearly four minutes slower at Brooklyn than I did pre-injury and almost six minutes slower at NYC. My pace didn't sustain — it collapsed in the back halves of both. The heart rate effort wasn't impressive, it was suppressed: my max HR in NYC was 168, twenty-two beats below my pre-injury max on the same course, and my average HR across both post-injury races was actually lower than in previous races, not higher.

Strava's sentence contradicts the data Strava parsed to write it.

The aerobic base is intact, but the ceiling collapsed (max HR way down across both post-injury races). The fade compounds in late miles, gets worse on hills, and there's a tell at mile 11 of Brooklyn where my HR dropped to 152 on a flat stretch — which means the bottleneck isn't cardiovascular, it's neuromuscular.

Probably some mix of actual inhibition and a subconscious unwillingness to fully load the hamstring. I asked it, “Is it a lack of trust in my hamstring?”

It said this:

“A few things in your data make me think it's partly trust but not entirely:

The mile 11 Brooklyn data point — 7:17 pace, HR 152, no hill — is interesting. If it were pure protection, I'd expect HR to stay elevated (you're trying, the muscle is just guarding). Instead HR fell off a cliff. That looks more like "the system disengaged" than "I'm consciously holding back."“

It even suggested a specific workout I could run to differentiate the two.

That's an incredibly useful piece of analysis. It tells me what to bring to my trainer.

Strava only told me I was a champ. Womp. Womp.

Here's the part that should bother everyone established at the top of their category right now: Strava had everything Claude had and more. Years of my training history. Heart rate trends. The same course from last year. My recent volume, my old races, my injuries embedded in the titles and descriptions of races.

They had all the data and produced a fortune cookie. Claude, given four files and a question, produced actionable insight.

Similarly, my friend Margot Mazur posted last week about giving up on Duolingo after ten years and building a Spanish tutor on Claude in a weekend. Hers asks her questions about organic agriculture, local food culture, wine, and Mexican history — all things she actually cares about — instead of teaching her to say "the rabbit is eating an apple."

It tracks where she keeps slipping up. It recommends a podcast or a film at the end of each session. She says it's better than any language tool she's ever used, including the ones she's been paying for.

Duolingo should have built that. They've had her error patterns, her engagement history, her stumbles and her wins, for a decade. They had every piece of information needed to make Margot's tutor—all they needed was a scan of her Instagram for interests, and yet they shipped a green owl that guilts her instead.

Classic innovator's dilemma — except AI changes one thing about the dynamic that I don't think most incumbents have internalized yet:

AI makes the competition your own users.

Christensen's original frame was disruption from below by smaller, scrappier competitors. The threat was someone you could see — another company, a startup, a new entrant. You could at least watch them. Now the threat is invisible. Your most engaged user, the one paying you the most and the one who actually understands what they want from your product — they can build a version that beats yours over a weekend, for peanuts. They don't need to start a company. They don't need to raise.

The defense isn't more AI features. The defense is actually using what you know about the user.

If you're building an AI product right now, the bar is not "we have AI." Every product has AI. The bar is: did you use what you know about this specific person, on this specific day, with this specific history, in a way that makes them feel seen? Or did you ship a generic congratulations?

Strava had prior year's race times on the same course. They had my HR profile. They had a multi-month gap in my training history that lines up with exactly the kind of injury I've been mentioning in my own race titles and descriptions for months. None of that requires a structured "injury" field — a model trained on this data should be able to read it.

They shipped "you crushed it."

That's not an AI problem. That's a "we didn't actually look" problem.

Matt Slotnik (h/t Yoni Rechtman for the share) wrote a piece this week diagnosing the same problem in the public software markets, and his prescription is the right one. Incumbents have to build — but not in the measured, multi-year roadmap way they're used to. Take real free cash flow, stand up a small empowered labs group with an actual CEO mandate, and let it ship for the install base unencumbered by existing offerings, pricing, or messaging. No sacred cash cows. Compensation structures have to change. Talent assessment has to change.

Because, in Slotnik's words, “Prevent defense never works.”

Even Anthropic and OpenAI run labs efforts. The companies actually on the frontier know the frontier moves, and that building unencumbered by the past is how you stay ahead. The companies not on the frontier are running multi-year roadmaps in a world where the frontier shifts every six weeks.

That's not a strategy. That's a way to look surprised on your next earnings call.

Margot is going to keep her Claude tutor. I'm going to keep using Claude to read my training data. We are both, for now, still paying Strava and Duolingo, because the data lock-in is real and the migration cost is non-trivial. But every month, the gap between what these platforms could do with our data and what they actually do widens, and the cost of routing around them keeps dropping. Strava for example, doesn’t support multi-sport natively. I started thinking about vibe coding my own multisport Apple Watch app.

How long before I start selling it to other triathletes and packaging it with much better analysis? I could probably have it done in a week.

The first incumbent to actually do what Slotnik's describing — take real cash flow, build a labs group with teeth, and ship something that genuinely understands its users — is going to look like a genius. The rest are going to find out what it feels like when the disruptor is the paying customer.

It's a question I got a lot before Founder Unfriendly came out and became the #1 Bestselling Business Entrepreneurship book on Amazon, and honestly, it's the right question to ask. The market for fundraising advice is flooded. You can find advice on raising a seed round in about three seconds on Google. You can even have Claude create a raise plan for you. (H/T Tristan Pollack)

So why spend a year of your life on this?

Conversion, not search

Thinking about cutting through makes this feel like you're trying to win at search when really you think you need to think about it as winning at conversion. You're not trying to be the most findable on a certain topic. You're putting something out there so that when you do get found, you have transparency around your thinking.

A book is a brochure for your brain.

When a customer (in my case, a founder who might want to sit down with me in a fundraising workshop) gets referred to you or hears your name, they're going to ask: Who is this person and do I trust them?

At worst, they find nothing. At second worst, they only find what other people say about you which may or may not work out for your current focus.

Ideally, they find something direct from you that explains how you actually think.

A book, moreso than other mediums like newsletters, also gives you an excuse to be visible without feeling like you're just talking about yourself. You can reach out to your entire network and say, I wrote this thing, and suddenly you have permission to have conversations you wouldn't have had otherwise.

There's a market demand for books. People are reading them. They're looking for good ones—always recommending, even more so than newsletters, which I find people saying they’re more often unsubscribing to. (Doesn’t mean you shouldn’t write one—just means the bar is high to make a good one worth reading.)

A reader is Reading This!

Writing a book demands something different from you than a blog post ever will. When someone pays for your work, you owe them something. You have to think about the full scope of what they need, not just what you feel like complaining about that day. You become accountable. And that accountability forces empathy.

Doing some customer empathy exercises is critical to any successful career. When you write a book, for example, you are forced to think about scope. If someone is going to pay for this, how do I make sure I don't leave them with unanswered questions?

The writing process also trains you in a specific way. Once you're in "sharing mode," you become hyper observant. Every conversation with a founder became research for me. I noticed the questions people actually ask, the confusions they have, the gaps in what's out there.

Training that observational muscle makes you better at everything else you do.

Bots Eat Brains… Brrrrrraaaaains

Writing can also be a future proofer for you as a knowledge worker. If you're going to scale up your output, which is what your competition is doing, you'll probably find yourself teaching agentic tools how you do what it is that you do and your own unique insights into things.

One of the most exciting aspects of writing a book for me has been creating a corpus of knowledge that I used to power a customized chatbot to help founders with fundraising.

I built a free companion to the book at thankstoai.thisisgoingtobebig.com — Claude-powered exercises where founders stress-test their pitch, decode investor signals, and simulate investor conversations. Book buyers unlock an AI coach trained on the book plus my actual founder feedback sessions — real judgment patterns, not a generic chatbot.

Check out some of what it’s telling founders:

Team Human

Vibe coding and chatbotting aside, there’s also something very human I didn't expect to learn from: the asks. When you're ready to launch, you realize how much you need people. That reveals everything about whether you've actually been generous or just taking. It's a litmus test for your relationships. If you sit down to build your outreach list and realize you don't have people who feel like you've helped them, that's a problem way bigger than selling books.

This has been something I've been grappling with over the last couple of years. I feel like I've spread myself too thin and created a lot of small amounts of value for a lot of people. A great event, a newsletter, but further down the funnel I haven't done enough for people I held in higher regard or who I thought were very values-aligned. I realize I probably treated them the same as some random person who showed up to one of my events and found it helpful, but I never really did anything extra for them. In this way, the writing of my book has left me with some network and relationship building to-dos.

Let’s Work on This Together

We talk a lot about network building and mapping in this small thought leadership cohort I run called Visible Work. We put 10 or 12 professionals together three or four times a year who were interested in getting out there more in online conversations and engaging their network.

Building and engaging an audience sounds like it's just about selling some product or service now—or in my case, a book. It's not. It's social capital that compounds. Whether you're job searching, hiring, fundraising, or just trying to be useful in your community, the best time to plant a tree is twenty years ago. The second best time is now.

I've been writing this newsletter since February of 2004.

Over that time, a lot of people say they want to do what I do—share their thinking, build their voice, get their ideas out there, but they're stuck. They haven't gotten started, or they're not convinced it's worth the effort. This Visible Work cohort is the answer to that. It's not necessarily about writing a book. It could be a newsletter. It could be LinkedIn posts. It could be videos.

The end goal is the same: you get practiced, you find your voice, you build an audience. One day, if you want to, you can level up to something bigger like a book, but even if you don’t, you’ll be glad you invested in this social capital rainy day fund when you need your network’s attention on something.

If you want to learn more, drop me a line to find out about our May cohort.