If you're a consumer founder who's gotten passed on by investor after investor, you've probably been told some version of "You're a little too early for us"—or you've assumed that most VCs just don't understand consumer. There's some truth in that—but mostly if you’re pitching the wrong investors.

It's not the whole story, and honestly, stopping there doesn't help you. The struggle runs deeper. It starts before you ever send a pitch deck.

Most consumer founders bootstrap their way to a first product. They scrape together savings, make a first run, and sell it to people they know. That's admirable—and consumer investors often value that capital efficiency early on. The problem is when you overspend time in the room explaining how you've done a lot with a little and never get to the bigness of what you're actually building. The bootstrapper mindset got you here, but if it's still the loudest thing in your pitch, you're signaling the wrong thing.

So, yes, you need to be able to say in your pitch meeting that one day, you’ll sell $300 million of yogurt, energy drink, or whatever protein infused snack you’re hawking—and not just say it, but lay out the plan.

The first money often makes it worse. While more experienced consumer founders might raise from angels who've seen big outcomes in the category, the average first timer is taking money from folks that haven’t seen the big win. Yes, there are more angels with consumer operating experience than there used to be—but that's mostly true at the top of the market. The longer tail of CPG founders is still raising from friends and family, and that dynamic is actually more treacherous in consumer than in tech.

The average tech founder's circle doesn't pretend to understand enterprise software or the LLMs under the hood, but everyone in a CPG founder's circle eats food, uses skincare, and drinks beverages—which means everyone has an opinion. They think they know something about it because they like it. That confidence leads to messy money: onerous terms, early payback provisions, cap table landmines that will haunt the founder for years. The conversations that come with that money are shaped by people who are optimizing for "please don't lose your savings," not for "here's how you go dominate a market."

By the time a consumer founder is in front of a real consumer investor, they've already internalized the wrong framing.

Then, there's the business selection problem. Consumer founders don't often choose their category because the unit economics are beautiful. They choose it because they love ice cream, their kids had an allergy, or they wanted to share something about their culture, for example. This means they often end up defending economics that were difficult from day one—seasonal, low-margin, capital-intensive, brutally competitive. Passion-driven selection tends to produce another blind spot: founders routinely overestimate the size of the white space they've found and underestimate the credibility of the competitors already in it. Just because a problem is highly relevant in your daily life doesn't mean there's room for a venture-scale business solving it.

Now consider Chad Janis, who built Grüns—a gummy greens supplement—to over $100M in revenue in two years, then hitting $300 million before selling to Unilever for $1.2 billion. That is a genuine big win and what made it possible isn't what many consumer founders want to hear.

Chad didn't come from a passion for greens supplements or a childhood love of gummies. He came from Lazard and Summit Partners, where he spent years as a board observer to DTC brands like Solo Stove, Brooklinen, and Dr. Squatch. He had access to the proprietary financial data of over 300 brands. He knew exactly what best-in-class LTV-to-CAC ratios looked like before he ever launched a product.

He also thought differently about the product itself. The supplement industry's instinct is to optimize the formula—more ingredients, higher doses, clinical strength. Chad's instinct was to optimize for behavior. A nutritionally perfect product that people find too unpleasant to take daily is worth nothing. So instead of building a better greens powder, he asked why people stop taking greens powders—and built something that removed that friction entirely. That's not a marketing insight. That's a strategic one.

And critically, he could answer a question most consumer founders can't: why can this product exist now when it couldn't before? Investors ask this of every tech founder—what changed in the infrastructure, the tooling, the market, that makes this the right moment? Consumer founders rarely have a good answer. Chad had three. Switching from gelatin to pectin created a vegan-friendly base with higher heat tolerance that could actually hold dense, earthy superfoods without turning into sludge. Microencapsulation allowed bitter minerals and botanical extracts to be masked and time-released in ways that weren't previously possible in a chewable format. And advances in low-sugar matrices increased solids density enough to pack 60 active ingredients into a single gummy—something that was physically impossible with earlier formulations. These were genuine technical breakthroughs that made the product buildable in a way it simply wasn't five years earlier. That's the same structural argument a SaaS founder makes when they say "this only works now because of LLMs" or "cloud infrastructure made this unit economics possible."

Consumer founders almost never come in with that argument.

He was equally deliberate about competition. Rather than avoiding AG1—the dominant player in the category—he used them as a foil. He positioned Grüns directly against their "green sludge" reputation, and built around the three things AG1 couldn't easily change: taste, convenience, and price point. He pioneered an 8-count grab-and-go sachet format that required inventing new machinery because nothing on the market could handle it. For the first eight months, that meant 20 people in gloves sitting around a table, hand-packing and clamp-sealing bags. That's not glamorous. But it's what serious operational execution looks like before the flywheel starts spinning—and by the time it did, Grüns was shipping 4 million gummies a day.

Throughout all of it, he ran the business against a single non-negotiable rule: a minimum 3x fully burdened LTV to CAC. Not as a target—as a floor. He refused to acquire a customer who didn't hit it.

In other words, Chad Janis raised like a VC because he was one. And not coincidentally, he's exactly the kind of experienced operator that consumer is less likely to produce on its own—someone who'd been inside the room where the playbook lives before he ever started building.

Now, is prior VC experience the only path? No. Some founders figure it out mid-flight. Some catch a trend early enough that the traction speaks for itself, and they hire their way to operational competence once the flywheel starts. That happens. But I'd rather be a prepared founder who understands the targets and vets their ideas against them than someone who gets lucky once and can't explain why. Lucky is not a fundraising strategy. And it's definitely not a repeatable one.

But there's one more thing worth naming, and it cuts both ways. Tech investors dipping their toes into consumer don't always understand product in the consumer sense. They can't evaluate whether a drink tastes better, whether a formulation is more aligned with what a particular consumer actually wants, whether a brand will resonate.

As Mike Duda of Bullish put it: "VCs are better at figuring out what other VCs might like than what the typical American consumer might."

If they don't like it personally, it's an easy no—which means consumer founders are often being evaluated not on whether their product will win in the market, but on whether it appeals to a room full of people who aren't their customer. Subjective product quality is essentially a non-argument in that room. The only language that reliably works is traction and economics—something that feels like science, not art. The problem is that early consumer founders often don't have enough of either. Consumer products don't go viral the way apps do. Retail distribution doesn't produce the kind of explosive week-over-week growth curves that make a VC's eyes light up. You're selling into a slow-moving, relationship-dependent channel—and not all products have the economics to make DTC work—especially if you only have a single SKU.

So here's the question to ask yourself before you walk into that meeting: Can you lay out a plan that shows you understand what Chad Janis understood going in—the unit economics, the LTV-to-CAC floor, the competitive positioning, the operational realities? Can you articulate the specific success metrics you're aiming for and make a credible case for why you can hit them? Can you explain why this product couldn't have been built five years ago and what's changed? Can you name the companies whose distribution, infrastructure, or consumer behavior shifts have paved the road you're about to drive on?

Or are you just telling them it tastes great and it's less filling?

Because that's the difference between the consumer founders who raise and the ones who don't. Not passion. Not product. Not even traction, necessarily. It's whether you've done the work to turn a great idea into an argument that sounds like science instead of art.

I backed a micro-mobility company about six or seven years ago. The company was run by a Hispanic founder. He was gritty, insightful, and every bit as hardworking as anyone I've ever funded. Yet, he struggled to raise. Ultimately, the company went under. Not having enough capital to push product innovation was the biggest issue.

I saw that Joseph Cohen had raised $14.2 million in total for Infinite Machine, with investors including a16z's American Dynamism fund. They’re building what can reasonably be described as Tesla for ebikes. They literally look like a pregnant Cybertruck gave birth to an ebike. I’m told it’s really fun to ride and as a big fan of the Revel scooters, I believe it.

If you’re looking at the two companies, the easy read is: bias. Hispanic immigrant founder couldn't raise, connected white guy from Penn clears double digit millions.

Case closed, right?

I thought it was an interesting example by which to dig deeper into the nature of how bias and capital access works.

It also make me think about a phrase that someone brought up to me recently:

“Comparable companies.”

She was sharing that Black founders, for example, “…have been shown to raise roughly one-third as much venture capital as comparable startups formed in the same year, industry, and state” versus their white male counterparts.

What should we count as a comparable startup? I see founders looking to who else raised capital all the time wondering, “Why that company and not them?”

Two NYC micromobility companies getting two wheeled vehicles in the hands of customers. We can put aside that they were different looking products and one was a rental model vs the other is a sale.

Those things change and VCs know it. These companies look pretty comparable.

Yet, I’ve taken a pitch from both of those founders and I know they aren’t.

I first met Joseph Cohen about 16 years ago when I was working for First Round Capital. Josh Koppelman had suggested I meet this founder he had met at Upenn. Josh called him a “rocket ship” if I recall.

He was building a product called CourseKit to replace what everyone agrees is god-awful software made by Blackboard. Blackboard is installed in nearly every major college and university, and one of the many things it does is run the Classroom software where homework is uploaded and the syllabus is posted. It's been there for 20 years. Nobody likes it, so his premise wasn't a bad one.

I thought he was pretty dismissive of the way software actually gets purchased by university IT departments. He believed that once everybody was using his software, administrations would have to concede, and they would tear out the system they had been using for a long time and replace it with a product built by a startup. I was pretty sure he had never even spoken to anyone within the university IT stack.

That didn’t hinder his confidence.

I didn’t see his pitch for Infinite Machine, but I’m 100% sure it was wildly different from the company I backed because of what each founder believed he was allowed to say.

My founder's pitch was always stuck between two modes: the big vision he wanted to build and the off-the-shelf scooters he was actually renting to show near-term revenue. He never fully committed to the "we're going to burn cash for 18 months and change urban mobility forever" pitch so it got muddled. Investors kept asking about the state of the company now, the nature of the progress he had made up to that point, and the downside economic risk of the current model—all questions he was probably more likely to get as a minority founder, but he couldn’t see his way out of them.

A “better fundraiser” could have judo moved these questions into a conversation about growth, but this wasn’t a failure of pitch skill or imagination. I think it's a completely rational response to growing up in a household where money was real, risk was real, and "we might go to zero" was not an abstract investor concept but an actual lived experience. He was pitching the way someone pitches when they've been taught that financial responsibility matters, but he was pitching in front of people who don't care about financial responsibility at all — they care about whether, if the risk was ramped up high enough, this could return a fund.

I'd be willing to bet Joe, on the other hand, walked in with a swing-for-the-fences pitch, blessed by a UPenn network of founders and operators to pressure-test it before he ever walked in the door.

That's the starting line. Not the room. Not the partner across the table.

When people talk about bias in venture, it feels like they're usually pointing at the decision-maker. Or, at least it felt like that to me as a straight white male decision maker.

You hear stories about the partner who asked the wrong questions and the room that looked like a fraternity reunion.

Did you get mistaken for a courier at the office of a VC firm?

That stuff is real and so are the numbers of who gets funded, but I still think we're focused on the wrong barriers.

Venture pitches come down to trust and fit. Do I trust that you can do what you say you’ll do and is what you’re saying you’ll do something really big?

Because we only get a small sample of a founder relative to the decade we’re going to spend with them going forward, VCs are bound to use proxies to assess trust. I didn’t work with you, but I know people who did. I don’t know how much work you put into diligencing this idea but other people tell me you’re really smart.

That’s a perfectly logical approach to a difficult problem. Why wouldn’t you rely on your network to help you make a trust decision?

Think about how you'd hire a babysitter. If your closest friend's sitter of five years suddenly became available, you'd jump at the chance to hire that person if you needed one. That's not bias — that's sensible risk management. You're not discriminating against strangers. You're prioritizing known quantities.

Investors do the same thing—and it’s a hard argument to make that they shouldn’t.

If you were early to a successful company, I can trust that you know what great looks like and the bigness of big.

If you’re in networks already adjacent to venture, I can trust you’ll source capital and talent faster and more easily.

As someone who built a fair diverse portfolio of female founders and founders of color, I saw first hand the extra miles that some of these founders had to go, because they didn’t begin on the same starting line.

They might have run faster and harder, but some people start out so far ahead, it’s difficult to suggest they don’t have a better chance of winning.

If you're a founder who came up without venture-backed friends, without the network of people who've already been selected by this system, without the nine months of cash runway to get to meaningful traction before you even start a conversation — you walk into that first pitch meeting already behind.

It’s not because the investor is prejudiced—obviously everyone has their biases, but those aren’t nearly as impactful as the fact that every rational signal they use to assess credibility is a signal underrepresented founders had a harder time acquiring than someone else.

If resilience was a driver of startup success, that experience would be an advantage.

I just don’t think it is.

The number one thing a founder is looking for is speed—and it’s hard to go faster when your better networked counterpart is running in a lane with one Mario Kart boost pad after another.

I backed a lot of underrepresented founders at Brooklyn Bridge Ventures. What I watched — and was slow to fully admit — wasn't that investors were treating them differently in rooms. It was that by the time they got to the room, they were starting from a fundamentally different position. One group of founders, on average, had enough cash to bootstrap for close to a year. The other was closer to zero net worth. One group had a text thread full of people who'd been through a raise before. The other was figuring it out first in their networks.

Same grit. Same intellectual capacity. Completely different starting lines.

I’ve heard some people identify this as a “pipeline problem” but that makes it sound like there aren’t enough capable founders from underrepresented communities. That’s B.S.

I think the issue is that these high potential founders aren’t getting networked in the same way—and where that begins for VCs is in the hiring practices of your companies. When you’ve got founders who keep referring to their AE’s as “salesguys” and who aren’t checking the counts of who even got interviewed for positions, you’re compounding a gap between who the industry sees as insiders versus outsiders.

If we' were to ever truly measure “comparable”, it would account for who had the warm intro network, who had already worked inside a funded company, who had the financial cushion to spend another six months iterating before going out to raise.

Strip all that away and you're not measuring bias anymore — you're measuring a gap that bias built long before the meeting happened.

Here's the uncomfortable part, and I'm going to say it anyway: if you're an underrepresented founder, you have to accept that the way credibility is measured isn't going away. You can argue it should be measured differently and maybe you'd be right. But in the room, today, the investor is still going to weight proximity, track record and network density, and they're going to do it largely without realizing it.

Fighting that in the meeting is a losing play.

What you can fight — and what actually moves the needle — is getting onto the treadmill earlier. Find your way into the networks where funded founders live. Do the work that gets you known inside ecosystems, not just adjacent to them. Understand that your job, unfairly, is to accumulate the credibility signals that other founders got handed by forcing your way in—and risk getting seen as pushy or overly ambitious, because we’re not trying to climb a highly political corporate ladder.

We’re trying to jump the buildings in the Matrix. It’s overly ambitious by design.

That's an ask that shouldn't fall on you. The fact that it does is an injustice.

Should the system work towards making itself more fair? 100%.

Can you afford to wait for that?

I've been doing a lot of talks with students and founders related to my new book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded which is now available for pre-order. (If you enjoy my writing here, please consider buying it now. If you e-mail the receipt to founderunfriendly@next.nyc, I’ll invite you to this amazing AMA series we have with founders from Datadog, Brigit, Zerohash and more…)

Here's how the post-talk networking usually goes: a minority of the people follow up with a LinkedIn invitation, and that's pretty much going to be it. They'll never follow up again. Ten years from now, either one of us will notice the other as a potentially important connection that seems valuable, but we have no idea how we're connected.

That's not a relationship. That's network lint that just gets in the way of a search to find a useful bridge to someone.

There’s a better way to establish yourself as a three-dimensional, memorable professional that adds value and offers a connection from a position of strength, no matter how down the ladder you feel.

I Will Follow

First, LinkedIn has a Follow button. It's one-directional. Use it. Follow me and set a notification to get my posts as they come in. You don't need my permission and you don't need me to accept anything.

Then, engage. How about a generous repost of my book announcement on LinkedIn?

“I just had the chance to hear Charlie speak to my class and given how much I learned in just an hour, I’m excited to dive into his book for founders.”

(Or, you know, your own version of that…)

That's your baseline. It costs you nothing but a little time and attention and it keeps the door open. No one is going to find it annoying.

Message in a Bottle

Soon after the talk, email me. Not a LinkedIn DM — email. You can get my e-mail. That’s probably one of the easier things you’ll figure out in your career.

Tell me what specifically you took away from what I said. Not "great talk," but this specific thing you said changed how I think about X. Tell me something about you, briefly. And then — this is the part almost nobody does — offer something.

But what? What’s a student or young professional have to offer? That’s where people get stuck.

The trick: have something ready before you even know who you're going to meet.

The best version of this isn't scrambling to find something useful after the fact. It's walking into any talk, any panel, any networking event with an offer already in your pocket. Something you can deploy for almost anyone—or at least a way of figuring it out quickly.

If you run a student podcast or a newsletter that goes to your marketing club, that's an asset. You can offer almost any founder or investor a platform, however small. If you're involved in a student org that could serve as a test group, you can offer user research — put an app or product in front of 20 people in your demo and send back what you heard. Those are standing offers. You bring them everywhere.

I Would Walk 500 Miles

But even if you have none of that, you have time and a willingness to do legwork that busy people won't do themselves. That's more valuable than you think. Say you meet someone building a proptech company that sells to real estate management firms. You probably don't know any property managers. But you could spend a week emailing 20 of them, introducing yourself as a student researching what technology they use in their operations. Some ignore you. One or two respond. And now you've done something the founder couldn't easily do — gotten a cold inbound from a potential customer — and you have something real to hand them.

Whoever you meet or listen to on a panel or podcast, if you can't figure out who the type of person is that they would accept a connection to any time from anyone, then you haven't understood exactly what this person does for a living and how they earn or what motivates them. You have to ask enough questions or do enough research (PS - AI can be a great partner for this) to understand the type of lead they find indispensable.

This kind of thing is a skill, and the best networkers I know started developing it early.

Ali Hamed, one of the best fundraisers I've come across, was doing this kind of legwork as a student — figuring out what connection someone needed and working hard to make it happen before anyone asked. He asked me for an introduction to one of First Round Capital's portfolio companies. Later on, he forwarded me a note from that founder thanking him for the valuable introduction to a potential customer he had made.

Mitchell Green, founder of Lead Edge Capital, used to blind-email people to each other at the beginning of his career when he was long on chutzpah (look it up), short on connections. I don't necessarily recommend it, but he was uncannily good at it. He once connected the founder of a direct-sales jewelry company to the COO of Avon.

When the founder asked how she knew Mitch, the COO said she didn't — but that he'd sworn she absolutely had to meet this person.

It was, in fact, a fantastic connection.

You don't have to go full Mitch, but I'll tell you one thing: most emerging VCs will take a warm intro to a real family office that's interested in venture. Almost any founder will take a meeting with a potential customer. The threshold for a useful connection is lower than you think, and the willingness to make one — cold, unbidden, with no guarantee it lands — is rarer than it should be.

Here's why this matters beyond the immediate relationship you're trying to build: if you can't figure out how to create value for someone when you're just starting out, with no title and no track record, you're going to have a hard time moving up. Every job you want assumes you have this skill. The people hiring you are banking on it. The question is whether you wait until you're hired to prove it, or whether you show it now — before anyone's taken a chance on you.

There's one more move before the LinkedIn request.

The heartbeat email.

This is exactly what it sounds like: a short, periodic update on what you're working on, thinking about, and learning. Once a quarter is plenty. The pitch to someone you've been orbiting is simple — I send this to a small group of people whose feedback I value. No pressure to respond, just wanted to keep you in the loop as I figure things out. That's it. No ask. No agenda. Just you, showing up consistently, as a real person with a point of view and a trajectory.

If they don’t like it, they can unsubscribe. That’s pretty much the worst that can happen, because if you never reach out, you wouldn’t have had a relationship anyway, so you’re not losing anything.

There are lots of simple tools out there link Mail Merge from Digital Inspiration that allow you to send this out. Claude Cowork can queue this up as individual notes for you as well, even tailoring them to the person.

If someone glances at it and something catches their eye, great. If it sits in their inbox unread, fine. The point is that over time, you stop being the person they vaguely remember from that talk once. You become someone they've heard from. Someone they've seen engage. Someone who's been quietly building in their peripheral vision.

Then you send the LinkedIn invite. By that point, you're not a stranger asking to be let in. You're a memorable, helpful, three-dimensional human being — exactly the kind of person worth having in a network.

You can tailor this in a way that feels authentic to you, as long you don’t end up in the worst case scenario—rediscovering this person ten years from now when you try to fundraise for your startup, realizing that you could have been slowing building up a connection with this person over time in a non-transactional way, but instead you have to go in cold.

You can find more advice like this in my book! Get it now!

Every emerging manager gets asked the same question eventually, usually by an LP who has seen too many pitch decks: “Why do you exist, and what are you genuinely better at than everyone else?”

A thesis and a network are table stakes. Everyone has those. And in a world where founders can get further on less capital than ever before, and where the number of funds multiplied wildly a few years ago, table stakes aren't going to hold up much longer.

The funds that are going to matter are the ones that have built something irreplaceable beyond the checkbook.

This isn't a new idea. First Round Capital didn't rest on having a great platform — they looked around, saw that other funds were doing content, and decided to build one of the most important repositories of startup knowledge that exists. The First Round Review raised the bar for what "being helpful" even means—and a huge percentage of the founders that they back, as they’ve discovered, have been subscribed well in advance of ever pitching the firm. Similary Jason Lemkin didn't just throw a SaaS happy hour — he built SaaStr—the preeminent conference and community in the space, which is even its own business.

These aren't investors who did the minimum viable version of differentiation and called it a day. They went all the way.

The next generation is doing the same thing, and the pattern I keep noticing is that none of them started by asking how to differentiate their fund. They started by asking what problem founders in their space actually had — and then built the thing that solved it.

Sophie Purdom, who I interviewed about this last summer, noticed that nobody was rigorously tracking every transaction in the climate tech space. Not as a fund strategy, just as a genuine gap in how the industry understood itself. So she and her co-founder started doing it, newsletter by newsletter, for six years. That data became Sightline Climate, now a thirty plus-person company selling market intelligence to corporates, banks, and governments. The investing came later, almost as a natural consequence — founders sought her out because she understood their space better than almost anyone. She calls it "earned deal flow." The differentiation wasn't the plan. Solving the problem was the plan.

Vic Singh, a GP at RRE Ventures, is co-founder and CEO of Originalis, building what he describes as the operating system for venture capital. He started from the observation that venture is a craft business that somehow runs on file cabinets — unstructured data, non-repeatable processes, institutional knowledge that lives in people's heads and degrades every time someone leaves. The problem he's solving isn't abstract. It's the one he lives every day: how do you move fast enough to win a deal without cutting corners on the work that tells you whether you should? His board pushed back on tackling network intelligence specifically. He did it anyway, because he knew from experience that the signal you actually need — relationship strength, domain expertise, recency — has never lived in any database.

I went in depth around the problem in this interview here:

What's interesting is that you're seeing this problem get solved from both sides simultaneously — vendors like Vic who are also practitioners building for the industry, and firms building internally for themselves. Melody Koh at NextView recently stepped back from full-time deal flow to focus on building the firm's own AI and data infrastructure internally. When I asked her why it had to be her and not an outside hire, she was direct about it: workflow problems belong to the people actually in the workflow. Someone who has never decided whether to spend a partner's time on a company can't build tools that make that decision better. You can buy scaffolding. You can't buy the judgment about which problems are worth solving.

USV took a different path to the same destination. Spencer Yen and the USV team spent three months building a team of internal agents — Arthur for deal analysis, Ellie monitoring investment emails, Sally for meeting transcripts, Connor tracking the calendar. What started as a simple meeting recap email became, incrementally, the foundation for how the firm organizes everything it knows. The problem they were solving wasn't "how do we become an AI-native firm." It was simpler: how do we make sure the context from our conversations doesn't get lost?

Everything else followed from that.

Mike MacCombie has built 146 communities across cities, stages, sectors, and functions. Not because community is a good differentiator on a pitch deck, but because he understands from a behavioral science background that the highest-trust networks are the ones that compound — and that founders in his verticals need access to each other as much as they need access to capital.

The thing worth noticing is that none of these people are building to impress LPs. They're building because they identified something founders or the industry genuinely needed, and they had a specific ability to provide it. The fund differentiation is real, but it's a byproduct.

Which brings me to the question I'd ask any investor who's reading this: what problem are you solving for founders that nobody else is solving? Not what makes your fund unique on paper. What do founders in your space actually need that they can't get anywhere else — and are you the person to build it?

It’s something I try to help my coaching clients—VCs and those trying to break in—think about.

If you don't have a clear answer to that, that's where to start.

You’re sitting in a board meeting watching your CEO paint a picture of the next 18 months, and everything they’re saying is…

…not impossible, but...

But you know the assumptions underneath it. And you’re about to have to present the model that’s supposed to back all of it up.

That tension — between what’s possible and what’s probable — is the part of the job you feel your reputation is tied to. Not the spreadsheet. Not the close. The job is being the source of truth in a room that has strong structural incentives to prefer the optimistic read is what causes you the most anxiety.

CEOs raise money by being ambitious. VCs invest by underwriting ambition. And the CFO sits in the middle of that, responsible for keeping things grounded in a culture that was explicitly built around believing the improbable.

I had lunch today with a group of startup CFOs and some of nextNYC’s supporters from Stifel Bank and KPMG, and this was the topic that kept surfacing.

Two approaches came up that I thought were genuinely useful:

The first was the audit committee. This is a standard governance mechanism that plenty of startups skip because they think it’s too formal for their stage. It’s not. The audit committee gives the CFO a dedicated forum — a smaller group of board members with finance or operational backgrounds — to walk through the numbers and assumptions without the CEO in the room. That last part matters more than it sounds. There’s a specific dynamic that happens when you try to have a grounded conversation about probability and a founder who raised a Series A on vision and conviction is sitting across the table from you. The audit committee lets the CFO actually do the job of informing the board, rather than managing a real-time negotiation between what the numbers say and what the CEO wants the room to believe.

The second approach was about shifting towards clarity on how the inputs all roll up and who owns them. One CFO described her role as essentially educating the board on how all the levers work — not just presenting the model, but making sure every board member understood which driver produced which outcome, and who in the organization was accountable for each one.

Instead of “we’ll hit 50% quarter-over-quarter growth,” the conversation becomes: “we can hit 50% QoQ growth if marketing delivers X leads and sales closes at Y efficiency — and here’s who owns each of those. They’ll go into more detail on how their teams will try to get to those levels.”

That’s not only more honest, but it’s also strategically smart. It distributes accountability where it actually lives. The CFO stops being the person who either sandbagged the plan or failed to deliver it. The model becomes a collective assertion rather than a personal prediction.

Both of these are really about the same underlying move: creating structural conditions for honesty in a context that otherwise makes honesty very hard.

Startups don’t fail because CFOs ran out of ideas for keeping things grounded. They fail because the incentives, the dynamics, the whole culture around fundraising makes it easy for everyone to agree on a number — and very hard for one person to say the number isn’t real.

You can’t opt out of the ambition. That’s not how these companies work, and you wouldn’t want it to be. But you can build the forums and the frameworks that give the truth somewhere to go.

That’s the job. The spreadsheet is just the vehicle.

For more insight into how your board and cap table can affect your plans, check out our upcoming webinar: Your Cap Table is Your Strategy.

In 2010, Facebook launched Places. It was their answer to Foursquare.

It failed almost immediately—not because the feature was bad.

The graph was wrong.

When people built their Foursquare networks, they did it knowing exactly what the app was for. A Foursquare friend request meant something very specific: You’d be ok running into this person IRL. Facebook's graph was built for something else entirely—reconnecting with classmates, staying in touch with family, documenting life milestones. By the time Facebook tried to bolt location sharing onto that, nobody wanted to tell their grandmother where they were having drinks on a Tuesday.

The graph had no context. It failed.

I've been thinking about this a lot lately, partly because I've been poking around Goodword’s relationship management platform and a handful of other "network management" apps. Also, I was talking to Vic Singh, who is building Originalis—an operating system for venture capital.

He said something that crystallized the whole problem.

Vic was explaining how Originalis uses network intelligence to help VCs figure out who they should pull in for diligence on a deal, who they should be warming relationships with before a fundraise, and who the right follow-on investors are when a portfolio company goes out for a Series B. What he kept coming back to was: you can't do any of that if the underlying graph doesn't know what the relationships actually mean. You might have a connection to someone on LinkedIn, but does Originalis know that you met them once at a conference versus that they were your co-founder for three years? Those are not the same relationship. The strength, the recency, the context—all of it matters.

Without that, you're not working with a network. You're working with a contact list.

That's the problem every consumer network management app has failed to solve, and most of them haven't even tried. There are lots of other apps that have asked for my network as well—to help me figure out who to share the app with.

Here's what typically happens: you download one of these apps and you start alone. You need connections to make it worthwhile, but you don’t know who you know that’s already on. In the early days, you might be the first one through the door.

It asks you to connect your LinkedIn, Facebook, etc., or upload your contacts. You're then handed a decontextualized blob of everyone you've ever emailed or connected with—your college roommate, the person you met at a conference in 2017, your kid's pediatrician, a founder you passed on, your high school friend who sells insurance now. They're all in there.

There's no single player mode. There's no foundation. And there's no way to act intelligently on a graph without understanding what each relationship actually is.

What makes this harder is that "network management" isn't even one problem. For me, right now, it's at least five distinct ones: making more time for individual friends when I'm a time-poor parent of a toddler; building a lightweight professional CRM for non-sales relationship work like VC coaching, finding activity partners (local cyclists, softball players who can rake), trying to find more couple friends in Brooklyn with similarly aged kids who also have a Wednesday date night. These all involve discovery, scheduling, and accountability at different times.

Those are not the same problem. An app that tries to solve all at once will likely solve none of them well.

What would it actually take to do this right? If you’re really going to be the next LinkedIn or the world’s best personal CRM, what’s the first hurdle?

I’d start by helping people understand who they actually know before you try to do anything with that information. Run a structured interview. Superhuman scaled plenty while still requiring a 1:1 chat to walk you through their app, so we’ve seen it work before when someone considers the problem important enough and the system promising.

Walk a user through their circles. Where did you grow up, and do you still talk to anyone from then? Walk me through your resume—what communities did each chapter create? Where does your kid go to school, and how do those parents communicate? What WhatsApp groups are you in? Layer in cross-platform data—calendar, email, some entity resolution to figure out that OldMetsFan1986 on Instagram is actually my friend Bob.

Then, critically, ask what success looks like in each circle. Not "do you want deal flow?"—that's a LinkedIn question. Ask: what does being a good friend look like to you? What do you regret not doing better?

That messy, friction-heavy onboarding is the product. The features everyone's building on top of it are only valuable if that foundation is there. Vic had to fight for this at Originalis. In his first board meeting, one of his investors told him nobody had ever cracked the network intelligence problem and he should skip it.

He didn't, because he knew the whole thing falls apart without it.

Most consumer apps skip it because it doesn't scale the way investors want things to scale. So we keep getting apps that ask for your whole contact list, build features on top of a broken graph, and then wonder why nobody sticks around or finds value.

Facebook Places was sixteen years ago and we still haven't learned this lesson.

One of the best pieces of fundraising advice I ever gave — and honestly didn't fully appreciate until I said it out loud — came out of a conversation I was having with Lauren Pearl, a CFO advisor who works with a lot of early-stage founders on bias in fundraising.

Specifically, the well-documented phenomenon where female founders get asked disproportionately more risk-focused questions than their male counterparts. The HBR study on this is worth reading. The basic finding: investors ask women "prevention" questions — what could go wrong, how do you protect against downside — and men "promotion" questions — what's the opportunity, how big can this get.

Lauren was making the point that founders who face this kind of bias need to be extra prepared. Have the numbers buttoned up. Be ready to defend the model. Know every assumption. I agree with all of that, up to a point.

Here's where I pushed back: Don't answer the question.

Not literally — I don't mean be rude or evasive. I mean: getting the question right and answering it well are two completely different things. And if someone's spending 70% of the meeting asking you about downside risk, and you spend 70% of the meeting answering those questions thoroughly and correctly, you've still lost.

Nobody has ever written a check because the founder did a great job defending the bear case.

The goal of a pitch meeting isn't to answer every question you get asked. The goal is to spend as much time as possible talking about why this thing could be massive. Investors write checks based on upside. Full stop. And if the bias in the room is pulling the conversation toward risk and downside — intentionally or not — then your job is to redirect without being dismissive.

That's actually a harder skill to teach than "know your numbers."

I've watched founders — and this is much more common among women, in my experience — answer a question so thoroughly that they spend five minutes in the weeds when they should have taken fifteen seconds to acknowledge it and pivot back to the opportunity. Something like: "Great question, and we've modeled that out — happy to go deeper after if useful — but what I think is actually more interesting is how fast the dentists who adopt this are growing..."

That's not dodging. That's selling.

There's a sales technique that's actually decades old — you've probably seen it and not realized what you were watching. The opener is something like: "Here's how I'd like to spend our time together. I'll give you a quick overview of what we're doing, and you can tell me pretty quickly whether this is something worth going deeper on. Does that work for you?" And then the whole room has opted into your agenda. They consented to the structure. It's elegant. It works.

Founders — especially founders who are likely to face tougher scrutiny than average — should be doing the equivalent of this. Not just preparing answers, but preparing the architecture of the meeting. Where do you want the conversation to go? What question do you want them to ask you? How do you get there from wherever they start?

The power dynamic in a fundraising meeting feels real. Someone has money, you need it, and they're asking the questions. But that's not actually how it works if you're good at this. The best founders I've seen treat the meeting like a conversation they're leading, not a test they're taking.

You're not there to get graded. You're there to show someone a picture of a future that's so compelling they're scared to miss it.

The bias question and the room-control question are connected in a way that I think doesn't get discussed enough. If you know going in that the questions are likely to skew negative, then the countermove isn't just having better answers to those questions. It's having a plan to keep the conversation from living there.

You can be prepared for every single worst-case question and still lose the meeting if that's all you talked about.

Want more takes like this? Check out my upcoming book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded.

A founder I've been working with described a feedback session we had as being "ripped apart."

Call me a New Yorker, but I don’t think I ripped him apart.

In my view, I'd offered some observations — things that weren't landing, a framing change or two, and things he needs to sharpen and answer for himself. Normal stuff based on my 20 years in venture and the kind of feedback that, if you're going to raise money, you need to be able to receive, process, and use.

But, in his retelling, it was something more dramatic. Something that happened to him.

When I pointed this out — gently — he paused and said, "I think I might have rejection sensitivity disorder."

I’d never heard of it, but it’s actually a real thing. Or at least, a real observed phenomenon if not a clinical diagnosis. In my research, Rejection Sensitive Dysphoria is most commonly associated with ADHD, and it refers to “intense emotional pain in response to perceived or actual rejection, criticism, or failure”.

The reaction is neurological, not just psychological — and it's often disproportionate to what actually happened.

For any founder that experiences such a reaction, fundraising presents a problem. Raising money is basically a prolonged, structured rejection gauntlet. You pitch 50 people. 45 say no. Of the 5 who say yes to a meeting, maybe 1 writes a check. And that's if things are going well.

If every "no" lands like a referendum on your worth as a human being, you are going to have a very bad time.

I had another founder — different conversation, different feedback — who responded to something I said with: "Your response made me laugh and crumble simultaneously. I appreciate the frankness — it is the kindest thing."

Laugh and crumble simultaneously. That's a reaction she can build on and learn from. Not defensive, not devastated — but kind of both things at once, held together. That founder didn't experience the feedback as an attack, even though it wasn’t easy to take. They experienced it as information, delivered by someone who cared enough to be honest. It was emotional, but still usable.

Same input. Completely different reception. That gap is can make the difference between success and failure in a pitch. When you’re able to turn rejection into a roadmap, you can get to work on achieving your end goals.

When rejection is a flash flood, it makes you feel like the path has been washed away.

I've been thinking about this in a different context too. A friend of mine threw a big birthday party dinner recently, and the turnout was genuinely great — warm, full of energy, the kind of night you remember. I found myself struck by it.

At first I felt like she's just better at maintaining friendships than I am, because I might not have gotten the same turnout, but then I realized a lot of people got that invite. It’s kind of how she runs all of her gatherings—let everyone know, and whoever shows up, shows up.

In that sense, she has a remarkably high tolerance for what most people would experience as rejection. The invite list was large—way larger than most people would feel comfortable sending, so technically far more people said no than yes.

But she didn’t seem to mind that at all. She just experienced the people who showed up.

I do the same thing with a conference I run for founders called the Pre-Series A Offsite. We get around a dozen or so Series A check-writing VCs to spend a full day with us. It’s a huge ask, but it makes it worthwhile for the founders who attend. That’s why we’ve been able to get companies like Spring Health ($2.5 billion valuation), Hugging Face ($4.5 billion valuation), Brigit (acquired for $460M), Air ($63M raised), Hone ($52.4M raised), and MixLab ($41.6M raised)—all before their Series A. Founders are busy, so we have to make it worthwhile.

To actually get our dozen investors this time around, I had to send 77 invitations. That’s about a 15% acceptance rate, or if you’re focused on the other side, 85% of the VCs that we ask don’t want to come. :)

So while some people might think, “That’s amazing that you get all those VCs to come from firms like Lightspeed, GV, Insight, etc” what they don’t see is everyone who didn’t even respond.

I’m fine with that. People are busy. It’s a huge ask. Maybe I’ll get them next time.

Most of us quietly curate our invitation lists to protect ourselves from the sting of low attendance. We tend not to ask hard questions of people we know won’t go easy on us. We stick to friendlies and narrow the ask to control the outcome. We'd rather invite 10 people and have 8 show up than invite 100 people and have 30 show up — even though the second scenario is objectively better as an outcome (unless you’re an introvert, of course).

The founders who fundraise well tend to have this same quality. They can send 200 cold emails, hear back from 12, meet with 6, and move on without a crisis. They're not deluded — they know most people will say no. They just don't let the no's accumulate into a story about themselves.

What I keep coming back to is how invisible this is as a constraint.

You can't fix a constraint you can't see.

I don't think low rejection sensitivity is something you either have or you don't. I think it's something you can work on — deliberately, by separating the outcome from your identity. A pass on your pitch is information about fit, timing, and stage. Feedback that makes you crumble is only useful if you can also laugh.

The kindest thing someone can do for you is tell you the truth. Whether you experience it that way is up to you.

If you got passed on and you're blaming the cap table, I want to push back on that.

I recently hosted a webinar with Qapita, my favorite cap table management software and nextNYC sponsor, with Holly Neiweem, Managing Partner of Apprentice Ventures, and Colin Kirby, who heads the emerging companies and venture capital practice at Foley Hoag. Between them, they've seen it all — 90-investor cap tables, departed co-founders sitting on 40% fully vested, angel investors still on boards three rounds later with no follow-on check to show for it. And their message was consistent: a messy cap table is almost never the actual reason a deal doesn't get done.

Holly put it directly: there literally isn't a cap table that can't be cleaned up with the right amount of time, effort, and money. Colin backed her up — no cap table issue is too big, it's all a function of how good the company is and how much capital wants to come in.

So if an investor passed on you and cited cap table issues, here's the hard part: they probably just weren't that interested.

Vague feedback is a pass, not a to-do list.

Holly made a distinction that every founder who's been passed on should internalize. When an investor is genuinely interested and the cap table is a real obstacle, they get specific. They tell you exactly what needs to be fixed. They ask for documentation. Sometimes they help you think through how to get there.

Vague feedback — "the cap table feels messy," "you gave away too much equity" — is a softer way of saying no. It's the same thing LPs do to VCs. Nobody wants to be the bad guy, so they reach for something structural and inarguable. Don't let that become the story you tell yourself about why the round didn't come together.

That said — if it's actually broken, own it upfront.

Cap tables can create real friction. Not unsolvable friction, but real. The issues that actually give investors pause aren't the math — they're the signals. A departed co-founder with 40% fully vested isn't just dead weight. It's a question about your judgment and your relationships. An angel still on your board three rounds in, who hasn't written a follow-on check, is a flag about the power dynamics inside your company.

What makes those things workable is transparency. Holly was clear: founders who get ahead of the mess — who walk in and say "here's what happened, here's what I learned, here's what I'm doing about it" — can get deals done. Founders who make investors piece together the narrative through diligence? That's where things fall apart. Because if you're not straight about your equity, they'll wonder what else you're not being straight about.

The percentage obsession is mostly noise.

One more thing: stop comparing your cap table to your friends at YC. Colin was blunt about this — don't listen to anyone who tells you there's a magic number you need to be above to raise your next round. Every company gets here differently. If a founder has 18% going into their Series A instead of 25%, that's a conversation, not a dealbreaker. And if the company is working, there are always mechanisms to true things up later.

The real question was never whether your percentage is "right." It's whether you and your co-founders are still properly incentivized to build something great. That's what investors are actually evaluating.

Investors who want in will find a way.

They'll negotiate around complicated terms. They'll help you think through how to approach a difficult co-founder. They'll work with the lawyers on the cleanup. What they won't do is manufacture interest that isn't there.

So do the honest postmortem. Is there something structural that genuinely needs fixing before you go back out? Fix it. But don't let "the cap table" become a convenient explanation that lets you avoid the harder question — whether your pitch, your traction, or your story is what actually needs work.

I had the good fortune of starting my career working for two of the most recognized names in venture capital — Fred Wilson at Union Square Ventures and Josh Kopelman at First Round Capital. 

When I was at Union Square, Fred Wilson was the most visible VC in the NYC ecosystem. That meant I had a door-opening name I could drop. The problem was that when the door opened, people were often a little disappointed that I was the only one who walked in, instead of my boss.

At First Round, the dynamic was different but the lesson was the same. The first deal I ever did was a co-investment with a prominent East Coast firm. Their lead partner pushed to have Josh Kopelman named as the board member — not me — even though Josh had nothing to do with the deal. I had sourced it and done the work. 

It didn’t matter. They wanted the name on the board.

If you’re a junior investor right now, none of this is surprising. You’ve felt it. You send the email and it goes unanswered. You get the meeting, but the founder is clearly waiting for your partner to join, or even explicitly asks. You make the intro internally and someone senior takes over. You’re working hard for the firm, but it’s not clear that your long term value as an investor is accruing. 

Are you actually gaining “juice”, or just renting someone else’s?

When a prominent GP walks into a room — especially one who built and sold a company — they carry things you don’t yet have. They have a track record. They’ve signed checks that mattered. They’ve sat on boards that produced outcomes. Founders can Google them and see proof. They’ve made money for LPs. They’ve made money for themselves. They’ve made mistakes publicly and survived them.

They also carry pattern recognition that’s been stress-tested. They’ve seen cycles. They’ve seen companies break and recover. When they give advice, it’s coming from scar tissue, not theory. And, maybe most importantly, they have accumulated trust — with founders, LPs, and other investors. That trust shortens the sales cycle for everything they do.

You don’t have that yet. Not because you’re incapable of earning it. You just haven’t yet. You can’t compress two decades of reps into two years of hustle.

So if you’re trying to compete on the same axis — pure authority, pure brand, pure “take my meeting because I’m important” — you’re going to lose. The question isn’t how to fake that signal. It’s how to build leverage in a different way.

The Disadvantage Is Real

When you’re the low-status person at a firm, the math is simple. Founders want the GP. Operators want the GP. LPs want the GP. The firm’s signal sits with the most senior person, and everyone else is trying to borrow it. If your firm has a strong brand, you draft behind it. If it doesn’t, you’re pushing uphill.

So your outbound doesn’t convert. You’re emailing founders who don’t know you, don’t know your firm, and don’t have a clear reason to take a meeting with you specifically. When the numbers don’t convert to enough high quality deals, the instinct is to do more outbound, but that’s usually the wrong move.

What You Already Have (But Aren’t Using)

Most junior investors miss this: you already have access to a network that most people would never get. 

Your firm’s GPs, portfolio founders, and LPs — especially operators, founders, and successful executives — are sitting there, dramatically underutilized. They chose to invest in your firm, they are aligned with your success, and many of them have the exact networks and perspective you’re trying to build from scratch.

The problem isn’t access. It’s that you’re not using it. Start reaching out.

You’re actually not asking these people for favors. You are offering them something. Smart, accomplished people have a constant need to stay relevant. They have ideas they want to express, perspectives they want sharpened, and stories they want told. They need to feed the beast of staying relevant in a changing technology landscape. If you show up with real curiosity and offer to capture that conversation, you’re solving a problem for them.

Don’t overproduce it or pitch it as a podcast. Just say: “I’m trying to get smarter on [topic]. You’ve seen more of this than almost anyone I can think of. I’d love to record our conversation — not sure what I’ll do with it yet, but I’d love to have it.” 

Almost nobody says no, and if they do, it doesn’t matter. There are other fish in the sea.

The Flywheel

Start inside the firm. Ask your GPs who the two or three people in their network that you should talk to about your focus area. Get the intro, have the conversation, record it, ask good questions, and actually listen. 

At the end, ask one simple question: who else should I talk to?

That question compounds everything. A warm introduction from someone credible is worth far more than dozens of cold emails. If you do this consistently, patterns start to emerge. You hear the same problems repeated, you notice what smart people disagree on, and you begin to form a point of view. That’s your thesis—not something you declare, but something that emerges.

Only after that should you start sharing it publicly. Not to perform, but to signal. When you’ve had real conversations in a space and write something thoughtful about what you’ve learned, the right founders start finding you.

P.S. If you really want to level up, ask them what their needs are–and spend some extra time trying to offer an intro back to them. Are they looking for customers? Is one of their angel investment founders looking to install OpenClaw and see what they can do with it? Be that resource.

Other Winning Recipes

In Margin Call (which is a highly under the radar movie with an amazing cast) Jeremy Irons says:

“There are three ways to make a living in this business: Be first, be smarter or cheat.

Now, I don't cheat.

And, although I like to think we have some pretty smart people in this building, it sure is a hell of a lot easier to just be first.”

While you lament the fact that everyone wants to talk to your boss, you need to see that as a window. The GPs at your firm have their time taken up by LP fundraising, firm administration and a ton of other commitments–and they’re often limited in the hours they’re working by additional family and outside commitments.

That supply demand imbalance is an opening for you–an opening to get to things before they have an opportunity for those things to find them.

So if the hot shot team that built the whole backend stack for Plaid has a new deal with three term sheets on it and your main GP is your firm’s only shot at getting in, you should be out figuring out who else at Plaid might be ready to leave, or who the most backable and trusted folks are.

That kind of thing is how I sourced Moat for First Round Capital. I was out at a networking event (a Blip.TV event for you NYC OGs) and met Mike Walwrath, former CEO and founder of Right Media, an online advertising exchange marketplace that was acquired by Yahoo for $850 million four years before. We got into a conversation about cycling and all the bells and whistles one can have on road bikes when you sell a company for that much. (I’m now that bike guy, only without the big exit to justify the expense.)

Someone stepped into the circle that he introduced as one of his investors… not someone who was one of his investors–meaning he clearly had a new company going.

I stepped aside and immediately called Josh Kopelman from the event–because I knew my rung on the ladder. I wasn’t going to be able to get us into that deal, but I knew that Josh could. He made the call and we wound up with a small but very profitable slice of Moat, which later sold for almost exactly what Right Media had sold for.

I wasn’t upset about not having the juice to pull the deal off myself. I was glad to be attached to a partner that did. 

The Time Audit

Do yourself a favor and check on whether you’re making the most of the opportunity you have being connected to far more experienced investors.

Pull up your calendar from the last month and bucket your time honestly. What meetings are you getting into that you could only get into because of where you are? Does your calendar reflect being associated with the best people in the network around your firm or is it basically at replacement player level–no different than anyone else who is connected to some money.

Think about the founders you’re trying to back–the ones you would feel lucky to be in a deal with. Would they be spending time answering cold emails from analysts? Who in the ecosystem would they be trying to spend the most time with? 

You should get to those people first and your partners are the ticket.

The gap between those two is your roadmap. Block two or three slots each week for higher-quality conversations that your GPs enable and protect them. 

If a slot opens up, don’t fill it with whoever happens to ask. Fill it intentionally with the best people in your firm’s network–the ones your GPs don’t have time to engage with but you do.

Remember, you didn’t sneak into the building. You’re in venture because your firm—your General Partners—chose you. They saw past the lack of a track record and recognized a specific, high-potential signal in you. 

You are an outlier in a hyper-competitive field just by being on the inside.

So, let's stop with the imposter syndrome and get to work.

Sixteen years ago, I wrote that, “Business plan competitions are the air guitar championships of the startup world.”

I meant that you can mimic all the movements of a startup without any of the real risk-taking or building. My criticism then was that we were teaching students to pitch without teaching them to build.

Fifteen years later, that gap matters even more. In a world where AI can help anyone ship a working product in a weekend, and where entry-level jobs are disappearing, the ability to actually build something—even something small—isn't just a nice skill to have.

It might be the whole ballgame—and I’m curious how many universities are thinking this way about their entrepreneurship programs.

Entrepreneurship Is No Longer a Track, It's a Survival Skill

I've taught or spoken in entrepreneurship related classes at Yale, Harvard, NYU, Fordham and countless other schools. I've been a judge at tons of student pitch competitions.

When I first started teaching, the technology students were most curious about was Web 2.0—blogging, digital media, what it all meant for marketing and communications. I was handed what was essentially a digital media class and turned it into something about the entrepreneurial mindset, but the audience for that framing was narrow. Learning these tools was mostly about getting ahead inside a company—the kind of thing that might help you get promoted at L'Oreal or P&G for leveraging blogs and social media for earned brand awareness.

After 2008, when banks stopped hiring, that changed. Tech went from a career accelerant to a viable career alternative to finance and MBAs sought out venture dollars instead of Goldman signing bonuses.

Now we're in a third moment.

With layoffs, AI absorbing entry-level work, and stable career ladders disappearing, being a builder—or an orchestrator of AI agents who build on your behalf—might actually be the only path college graduates have to a stable economic future. The idea that entrepreneurship courses are for the small segment of students who think they might start a company someday is just wrong.

Every student coming out of a university right now—especially in this job market—should be learning to think and act entrepreneurially, and that means trying to figure out how to generate income now.

Part of that means thinking about income sources differently. AI tools make cottage industries newly viable. You find a niche problem that isn't large enough to attract venture funding but matters enough to a small audience willing to pay. A student who builds something that earns even partial income while they're in school has changed their relationship to financial stability and professional risk in a meaningful way.

Fall in Love With Problems

One issue I see with that is students aren't fluent enough in the problems they're trying to solve. This isn't their fault—it's mostly a function of not yet having enough life and professional experience. You can't deeply understand the pain of managing a sales team or navigating a broken supply chain if you've never done it.

Second, entrepreneurship programs tend to attract people who are idea-oriented rather than problem-oriented, and they’re rarely builders. It’s still a bit of a novelty to teach entrepreneurship to computer science grads like I do at NYU Courant, and there aren’t many vibe requirements when you get a business degree.

Most of the time, when students self-select for being interested in entrepreneurship classes, you get a room full of aspiring founders who couldn't ship anything.

AI has now made that inexcusable—but has it changed how entrepreneurship is taught?

Vibe coding, no-code tools, agents—a student today can go from idea to not just a working demo in a weekend, but the actual product. The technical gap that kept entrepreneurially-minded students on the sidelines is largely gone. But the first problem—the fluency problem—remains. In some ways it's getting worse, because now students can build faster than they can validate. They can have a polished demo for a problem nobody actually has.

The fix isn't more hackathons. It's more conversations with people outside the university.

The Skill Nobody Grades

This is the piece that's consistently missing from entrepreneurship curricula: networking and relationship building. Not the cringe, transactional version—genuine curiosity about what real people face at work.

Students can't get input on what paying customers actually struggle with unless they're actively talking to them. And yet I still meet students who don't know the basics of staying in touch with people. They freeze up around "what would I even have to offer?" They haven't been shown how to expand their curiosity outward.

After I graduated from Fordham, I started an alumni mentoring program—52 pairs of recently graduated students connecting to juniors and seniors about to start their careers. The program has grown tremendously since then and continues to this day, but shouldn’t something like this be mandatory at all schools, for every single student?

Building professional relationships to inform your entrepreneurial interests shouldn’t be optional. It should be an assignment. Each semester, you should send an update to your network—to all the speakers that came into your classrooms and the alumni you met at sporting events. You should get credit for doing the thing that actually builds a career.

How else are you going to get to know an industry well enough to build a startup around it?

What AI Actually Enables (And What It Doesn't)

Here's how I'd tell students to use AI right now:

Use it for individualized coaching. Career offices can't scale for everyone, but AI can. An agent can check in, ask who you've been reaching out to, help you craft a follow-up email, and prep you for an informational interview. It can help figure out which alumni you should be reaching out to and how to approach them—new areas to explore, newsletters and podcasts to track, etc. The coaching infrastructure that used to require a full staff can now be partially automated—which means it can actually reach every student.

Use it as a writing companion, not a ghostwriter. Do the informational interview with alumni yourself. Talk through your ideas in your own words. Then use AI to shape the outline, tighten the draft, sharpen the argument. Your voice stays in it.

Ask it what entrepreneurial ideas might come out of your conversations—not necessarily venture backed ones, but what kinds of tools and services people would pay for now, so that you’re not cash flow negative the day you graduate.

Use it to test faster. No-code tools and AI-assisted development mean you can put something real in front of potential users quickly. That's powerful—but only if you're willing to hear no. Students' ideas don't get challenged enough. The bar for "is this actually worth building" needs to stay high even when building gets easy.

The opportunity here isn't that AI makes entrepreneurship easier. It's that AI removes excuses. The tools are available. The coaching can scale. The only thing left is the willingness to talk to real people, stay curious about their problems, and keep a high bar for what's truly worth working on.

That's what I'd want every entrepreneurship program to teach.

I wrote a book called Founder Unfriendly: What Investors Won't Tell You About Getting Funded, coming out April 28th. It's aimed squarely at the founders who don't have easy access to capital or well-connected networks—which is most of the students in entrepreneurship programs. If you run an entrepreneurship program and want to discuss bringing me in to speak, or getting the book in front of your students, I'd love to hear from you.

There’s an assumption founders make about hiring part time roles. At some point, when we can afford it, we’ll stop patching things together and hire the real person. We’ll commit to the singular owner. We’ll professionalize the function.

Fractional or modular support is what you do before you’re serious or successful.

I see this mistake everywhere. A founder hires one early marketing leader and expects them to own brand, demand gen, content, performance, product marketing, analytics, and team building.

It works for a while when you’re growing off a small base. Having someone do a smattering of things is better than having no one on it.

Then the job changes when you need focus and specialization to move the needle.

The skill set that got you from zero to traction isn’t the same skill set that scales paid acquisition, builds a content engine, or manages a team of specialists. Suddenly the first hire isn’t wrong. The role has outgrown the shape it started in.

Finance is a case study of the same dynamic.

Founders talk about hiring a “finance person” as if it’s one job and I recently interviewed my friend Chris Fenster at Propeller about this.

In reality, that early person, be it a VP, Director or Head of Finance, has a title that compresses bookkeeping, controllership, compliance, forecasting, fundraising support, board credibility, and strategic partnership into a single person. At scale, those are separate seats.

Subscale, they’re awkwardly collapsed into one—often times with the person being above average at one of those things and doing their best for the rest.

When you can afford four or five W-2 employees, specialization makes sense. Most companies can’t. Even companies that can afford one senior hire usually cannot afford all the jobs that person is implicitly being asked to do.

The common instinct at that point is to “fix” the function by making a bigger hire, mostly to solve an accountability issue to get “someone responsible for this.” That’s rational, but it doesn’t create capacity.

Chris said something in our conversation that reframed this for me: “If you’re subscale, it’s almost impossible to solve a systemic subscale problem with a scale solution.”

In other words, the reason this feels so hard isn’t that you’re bad at hiring. It’s that you’re trying to install a permanent, enterprise-grade answer to a company that hasn’t stabilized yet.

Plus, the job definition when a company is in hyper growth mode isn’t normally stable enough to justify locking it into a rigid, full-time box.

Early-stage companies are volatile by design. The work changes every few quarters. One quarter you need scrappy execution. The next quarter you need process discipline. Then you need institutional polish. Then you need deep specialization. Committing too early to a singular, fixed owner in a function whose requirements are still evolving often creates fragility rather than stability—be it finance, marketing, or any number of other areas.

Modular support is not a budget workaround in that environment. It is a flexibility tool. It lets you match resources to the actual shape of the work as it changes.

There is also a healthier mental model here: assume planned transitions. The early marketing generalist you hire is unlikely to be your VP of Marketing at $100M in revenue. The Series A/B finance director is unlikely to be your Series D CFO.

That’s not a failure. It is the normal arc of scaling.

Accepting that reality changes how you design the function. You document processes. You standardize workflows. You avoid over-titling in ways that make layering impossible later. You build redundancy so the company is not dependent on one person’s private playbook.

Modularity also supports that approach. You can maintain internal accountability at the top while surrounding that leader with specialized capacity that handles repeatable, lower-stack work. As the company grows, you can peel off the most standardized pieces and systematize them. That frees your senior talent to focus on judgment-heavy decisions precisely when complexity spikes.

What surprises people is that this logic does not disappear at scale. One of the more counterintuitive things Chris shared is that about half of their new work at Propeller comes from companies already doing $30M+ in revenue. Modular isn’t disappearing as companies scale; in many cases it becomes more valuable because it creates redundancy, standardization, and leverage for senior leaders during hypergrowth. Even companies doing tens of millions in revenue continue to use hybrid models. At that stage, modularity isn’t about scrappiness. It’s about resilience. Boards want accountability, credibility, and reliability. They do not care whether your most repeatable workflows are executed by a perfectly staffed internal team or a standardized external partner.

They care that the numbers are right, the systems are durable, and the leaders are focused on strategy instead of mechanics.

Fractional or modular is not what you do until you can afford to build the “real” thing. It is often how you build the real thing intelligently. I recently told an up and coming food business that their next step beyond pop-ups shouldn’t be a lease—they should work up through a step function. Commit to a weekend food court that will cost $6k, not a signature that demands $60k. Even if you’re blowing the doors off, keep the flexibility.

The work changes too fast to justify rigid commitments. Later on, the work becomes too complex to rely on single points of failure. In both phases, modularity is a feature.

The goal is not to avoid hiring. It is to avoid pretending that a singular early hire can permanently solve a function whose requirements are still in motion. If you design your organization around flexibility, documentation, redundancy, and the steady migration of repeatable work down the stack, you give yourself room to grow without breaking every time the job evolves.

That’s not a compromise. That’s strategy.

If you’re interested in geeking out over finance functions and how to staff the back office and ops infrastructure of a company, check out our next conversation with Chris, How Finance Leaders Should Actually Implement AI in 2026.

There’s been a pretty common belief in the venture and startup world that is changing:

If an employee wants to sell shares, they’re probably thinking about leaving.

If a founder takes some money off the table, they’re losing faith or they’re going to take their foot off the gas now that they’ve got some money.

I think VCs and founders are getting increasingly convinced this framing is off.

In a recent webinar with Amit Majumder, Head of Equity at Qapita (a Carta competitor and global equity management platform that helps startups and scaleups manage cap tables, employee equity, and investor reporting). We talked about how selling some equity can actually be a retention tool, not a warning signal.

The core misconception is simple: people assume early liquidity means lower commitment.

But I think the opposite is often true, and you can see the tide shifting. Recently, Clay announced a $55 million tender offer of employee shares at a $5 billion valuation, and here’s what they cited as the reason:

“This tender is designed to give our team the flexibility to use the value they create every day. Whether it’s buying a home, taking care of family, funding a passion project, or simply getting more breathing room, we want people to have options when life calls for them.”

For more insight into how Clay thinks about equity compensation, check out this part of an interview that Co-Founder Varun Anand did with First Round’s Brett Berson.

Varun said:

“…Treating people well and treating people in the right way and being generous with your best people, pays long term dividends, not only for doing the right thing, but also for the company and for both people involved.

And it feels not standard for how most companies handle compensation.”

When someone is in a suboptimal personal financial situation — where 90–99% of their net worth is tied to a single, illiquid company — it creates pressure. And pressure leads to bad decisions.

Not because people are unethical. Not because they don’t believe. Their entire financial life is riding on one outcome. How do you think that impacts conversations with their family and their day to day stress levels?

Giving employees and founders a chance to diversify a little while continuing to earn more equity in the aggregate can create real peace of mind. That peace of mind can meaningfully lengthen how long someone is willing to stay and keep taking risk with you.

Recently, Clay announced a tender offer, which I think is a great example of this more modern approach. It’s a signal that liquidity doesn’t have to be a binary “all or nothing” event at the very end of a company’s life.

Another data point from Qapita that stuck with me:

They’re seeing that only the first ~2.5 years of vesting is meaningfully retention-driving for most employees.

After that point, many people are already overexposed. Additional vesting alone doesn’t feel motivating unless it’s paired with refresh grants, education, and sometimes liquidity.

Equity seems to work better when it’s treated as a living system:

• Ongoing refreshes.

• Clear communication about dilution and value.

• Education around taxes and risk.

• And, in some cases, thoughtful tender offers.

This creates a counterintuitive takeaway:

Letting people take a little money off the table can make it easier for them to stay all-in.

Huge thanks to Qapita for partnering with nextNYC on this webinar series and pushing this conversation forward. If you’d like to learn more about what they do, you can reach out to their US partnerships manager Paul here.

Check out our next webinar on Fixing Broken Cap Tables on Tuesday, Febuary 17th.

A lot of my coaching clients have the goal of becoming a Principal or Partner someday. I almost never start by talking about titles. Instead, I ask a different question: three to five years from now, what kind of founders will already want to talk to you before you ever reach out? Not because of where you work or what’s in your bio, but because when they look at your background, they immediately recognize shared experience or unusually deep understanding of a problem they’re actively wrestling with. If you can’t answer that question clearly, the path to becoming a great investor is still mostly theoretical.

A recent example makes this tangible. Aliisa Rosenthal, OpenAI’s first sales leader, recently joined Acrew Capital as a General Partner after helping build OpenAI’s enterprise sales organization from a handful of people into hundreds at OpenAI, generating billions in revenue at unprecedented growth.

If you’re a B2B founder doing early enterprise sales and starting to think about how to scale go-to-market, it’s not just obvious why you’d want to talk to her — it’s almost inevitable. She was a sales leader in the single hottest category right now: enterprise AI. More importantly, she lived the exact transition many of those founders are in: moving from founder-led or product-led motion into building a real enterprise sales organization. That moment — when something is working but not yet systematized — is both the point where founders desperately want experienced guidance and the point where a firm like Acrew often wants to lean in. She doesn’t need to explain why she’s relevant to that stage. Her resume already encodes the overlap between what founders need and what her fund wants to fund.

When I asked her about what her experience enables her to offer founders, she replied "I can really help founders understand the current AI buying landscape - which has changed dramatically over the past few years - to navigate GTM strategy. I can also tap into my vast network of GTM operators to help them land the right initial team."

That’s what I mean when I talk about reverse-engineering your future deal flow. What are you uniquely positioned to help founders with?

Most people intuitively know that some experiences are more valuable than others, but they underestimate how steep the curve actually is. I think about it as a pyramid: a very small number of top-tier, generational experiences at the top, a larger middle of better-than-average experiences, and a broad base of average experiences. If your long-term goal is to work with fund-returning founders, you have to internalize something uncomfortable: those founders will seek out a very small number of people.

Not “someone who has sales experience.” Not “someone who worked in product.” But someone who built a sales team for a breakout company. Someone who led product through hypergrowth. Someone who scaled infrastructure at meaningful volume.

Level-setting matters. You don’t accidentally end up in that top sliver. You either take real risk to pursue a small number of high-potential operating bets, or you become deeply connected to those stories by documenting, studying, and sharing them. Ideally, you do both.

When I zoom out, I see two primary ways people become magnets for great founders. The first is shared experience. You were in the arena. You lived the specific pain: first enterprise customers, first VP hire, first broken process, first time something stops working. This path requires both risk tolerance and selection skill. You’re effectively placing bets on companies early with your career. The real question isn’t “Is this a good job?” It’s “Is this a problem I want to be known for understanding deeply?”

The second path is research and proximity. Not everyone will land inside a generational company early. But you can still build gravitational pull by becoming someone who studies a problem obsessively, interviews the best operators in that domain, synthesizes patterns, and shares what they’re learning in public. Over time, founders start to associate you with a category of insight. You become “that person who really gets X.” That association compounds.

Early in a career, I don’t think the right posture is “future expert.” It’s fast, continuous learner. You signal this by asking thoughtful questions, publishing what you’re learning, interviewing people who are ahead of you, and constantly expanding your knowledge graph. When you join a company, you’re not just bringing your own effort. You’re bringing the people you know, the people you can call, and the people you learn from. That extended network becomes part of your value. Over time, a pattern forms: you become known as someone who can figure things out quickly and knows who to go to. That reputation travels.

Here’s the part most people miss: your resume is quietly turning into a filter. It determines who reaches out, what kinds of conversations you have, and what kinds of opportunities cross your path. You don’t wake up one day and decide to have great deal flow. You build toward it by stacking intentional experiences, credible proximity, and public learning. Years later, it looks inevitable. In reality, it was designed.

I’m not writing this as someone claiming to have “done it right.” I’m writing as a long-time observer of venture careers, watching what compounds and what quietly stalls. I spend a lot of time helping people zoom out and pressure-test their assumptions about what actually leads to being sought after by great founders.

If your ambition is to someday be another firm’s version of Aliisa Rosenthal — someone whose background naturally pulls in a specific class of founders — that outcome isn’t accidental. It’s designed through a series of career choices, learning loops, and positioning decisions that stack over time. If you want a thinking partner to help map that path deliberately, that’s work I enjoy doing in my coaching practice.

I’d see ads like “Book Alexis Ohanian for $2,000” and think: “Really? He’s a good guy, but does he really need the money?”

(As it turns out, Alexis uses his Intro earnings to support causes like climate change and to positively impact the lives of marginalized people… but that’s a lot to squeeze into an Instagram ad.)

It felt off–especially when influencers routinely decry charging founders for anything. The thinking goes that founders should only take advice from people who are successful enough not to need to sell their advice–folks who are writing checks versus receiving them.

But over the last year, while writing my book and spending even more time with early founders, my view has flipped. The fact of the matter is that anyone successful enough to be making investments is prioritizing their limited time. They’re trying to spend as much time as possible with folks who have the highest immediate upside potential–and they’re lucky enough to be surrounded by a lot of people worth investing time in.

The question I’ve come upon is where that leaves everyone else who is still trying to figure it all out–whose idea isn’t quite there yet, or whose next steps are surrounded by more questions than confidence?

That’s actually most people by number.

When I think about those founders, I think about the value of their time. It’s a big theme of my upcoming book.

Founders dramatically underestimate how expensive their own time actually is.

Most people who start companies are already:

• Forgoing high-paying jobs

• Delaying financial stability

• Taking real personal risk in their prime earning years

• Raising from friends and family–folks who often aren’t nearly as wealthy as professional investors.

That’s not cheap.

And yet, I constantly meet founders who are doing something incredibly costly: spending months (or years) building in the wrong direction because they’re missing one or two critical insights that only come from someone who’s been down this road before.

Not motivational advice.

Not “you got this.”

Not vibes.

Real, direct, experience-backed feedback.

The hard part? That kind of feedback is surprisingly difficult to get.

VCs often want optionality. They don’t want to offend you. They don’t want to be the person who says, “In my experience, this argument doesn’t hold” or “I don’t think this is going to work.”

What if you figure it all out?

Friends want to be supportive. They’re rooting for you and they’re usually not in a position to evaluate your idea with real pattern recognition anyway.

So founders end up in a weird middle zone: lots of encouragement, very little truth.

That’s where I’ve started to see real value in paid, targeted conversations.

If you’re quitting your job to start a company, staying at that job two or three months longer and spending a couple thousand dollars of this additional salary you didn’t originally plan on having on the exact right high-level feedback from the exact right person can be a fantastic trade if you don’t already have access to these networks.

This way, you get your ideas challenged earlier, avoid putting good money after bad ideas or you get real confirmation that you’re onto something worth pursuing

Either outcome is incredibly valuable.

That’s why I’ve decided to become an expert on Intro, which is where I’ll be directing founders who want advice.

My goal in these sessions isn’t to tell founders what they want to hear. It’s to get to the heart of the argument, stress-test it, and give them advice they’re unlikely to get elsewhere.

To kick things off, I’m donating the first $2,000 of my Intro proceeds directly to the National Brain Tumor Society in memory of my parents. Both of my parents ultimately passed from brain tumors–my mom six years ago when an otherwise operable brain tumor was complicated by a long struggle with COPD and my dad from CNS Lymphoma a year ago.

NBTS is the largest non-profit organization dedicated to the brain tumor / brain cancer community in the United States.

In addition to traditional nonprofit research funding, the National Brain Tumor Society also operates the Brain Tumor Investment Fund as a separate venture philanthropy subsidiary.

I wouldn’t be who I am today if it wasn’t for them–and so making more time for founders and tech community professionals, and raising money in their honor, seems like a fitting way to kick things off with Intro.

If you’re a founder who’s early, in motion, and willing to have your ideas challenged, you can book time with me on Intro–or if I can be helpful in your path towards breaking into venture capital, you can book some time with me here: https://intro.co/charlieodonnell

(I can also chat about starting non-profit boathouses, breaking into triathlons, learning how to swim as an adult, or parenting–but the latter is probably where I have the least verifiable expertise.)

Or, if you don’t need anything in particular back for your support, you can support my raise directly here: https://nbtsevents.braintumor.org/charliesparents

I don’t think founders should blindly pay for advice.

But I do think founders should treat high-quality, well-targeted feedback as an investment.

Sometimes a few hundred dollars today can save you a few years and tens of thousands of dollars, if not more, tomorrow—and the time is the one thing you can never get back.

I’ve spent most of my adult life on social media.

I was early to blogging, Friendster, MySpace, LinkedIn, Twitter, Foursquare, etc.

I’ve written newsletters, run communities, hosted events, and watched every generation of “this is the new way to connect” rise and fall. I’m not anti–social media by any means—but over time, I’m lamenting how anti-social it’s all become. I don’t have Threads friends the way I used to have Twitter friends—and in an algorithmically driven experience, following doesn’t really mean I get to see what the people I care about post anymore.

Finally, I found something that feels like the next social network for me.

E-mail.

Not newsletters. Specifically, what I call Heartbeat E-mails.

A Heartbeat E-mail is a periodic update you send to a small, curated group of people you actually care about. Friends. Former colleagues. Mentors. Peers. People you’ve had coffee with and genuinely want to stay in touch with. It’s not marketing. It’s not a public broadcast.

It’s a way of saying: here’s what’s been happening in my life lately—professionally, personally, humanly, and please… write back.

What surprised me most is how effective it’s been—so much so that it’s now a part of our Visible Work curriculum. (Visible Work is a small, structured cohort starting next week that helps thoughtful operators, investors, and founders turn what they’re already thinking and doing into clear, consistent writing and ideas people actually engage with. E-mail me if you’d like to see the details and the syllabus. We’ve got two spots left.)

First, it keeps me top-of-mind for people I care about—and that has had a very real effect on my friendships. I’ve noticed that when I send these e-mails, friends follow up with actual movement toward getting together. “Oh, I meant to reply to this earlier—want to grab lunch?” I’m seeing people more often because I’m present in their mental landscape more often. Not through an algorithm, but through intention.

Second—and this one matters more—it creates space for real conversations that don’t quite belong on LinkedIn.

At one point, I shared something deeply personal in a Heartbeat E-mail: that my dad had suddenly gotten very sick. He was dealing with memory issues caused by CNS lymphoma, and it upended my life in ways I wasn’t prepared for. After he passed, it sent me down a rabbit hole of asking friends a hard question: “Do you know what you’d do if your parents became incapacitated tomorrow?”

The response was overwhelming.

People wrote back saying it prompted them to finally have difficult conversations with their parents. Others shared stories they hadn’t really talked about out loud before. One person I deeply respect—someone I don’t get to see often—reached out to say she was going through something similar with her mom, and it led to a long, honest conversation about family, illness, and navigating changing relationships with parents.

I probably wouldn’t have been on her call list otherwise.

That’s not a story I would have posted on LinkedIn:

“What I learned about B2B Marketing when my dad kept forgetting he had brain cancer.”

Heartbeat E-mails live in that middle space: semi-professional, semi-personal. And it turns out that’s where most meaningful relationships actually exist.

There’s another reason I’ve come to love them: they extend the half-life of a coffee meeting.

You know the pattern. You have a great conversation. You talk about what you’re working on, the thing you might need help with, the idea you’re excited about. And then… nothing. A year goes by. When you finally reconnect, you find yourself re-explaining the same context all over again and the other person has no idea what happened to that thing that was so important that it demanded one on one time.

Heartbeat E-mails solve that.

They’re the natural follow-up to a good conversation. Instead of that coffee being a one-and-done interaction, it becomes the beginning of an ongoing thread. People get to see what you actually did with the ideas you talked about. They see your progress, your pivots, your questions. You don’t have to reintroduce yourself every time—you’re continuing a conversation instead of restarting it.

Over time, something else happens: You become more three-dimensional.

Most people in our lives exist as two-dimensional abstractions. A job title. A company. A vague memory. But humans only have the cognitive capacity to keep about 150 people in meaningful orbit—their Dunbar number. To earn one of those slots, you have to feel real.

Memorable.

Human.

Heartbeat E-mails do that quietly and consistently.

When people know not just what you do, but what you’re thinking about, struggling with, learning from, and occasionally laughing about, you stop being a name in their inbox. You go from a dot to a line. You become someone they root for. Someone they think of when opportunities arise. Someone worth keeping track of.

This also scales.

Not infinitely, and not artificially. I started out with 100 people and the list has grown. When I have a good meeting or catch up with someone, I manually add them. There’s no sign-up page or CTA.

That discovery is one of the reasons I teach this practice inside Visible Work.

So many smart, thoughtful people want stronger professional relationships—but they don’t want to become content creators. They don’t want to shout into the void. They want a way to be seen and remembered as themselves.

Heartbeat E-mails offer that path.

They’re not about going viral. They’re about staying connected. They’re not about personal branding. They’re about being human at scale.

And for me, after all these years on social media, they’ve quietly become the most meaningful network I’ve ever built.

If this resonates—and you want to learn how to build a practice like this in a way that feels natural, sustainable, and true to you—that’s exactly the kind of work we do in Visible Work.

There’s a well-documented dynamic in fundraising that most founders feel long before they ever read about it.

Research (including a now widely cited Harvard Business Review article) shows that women and underrepresented founders are far more likely to be asked downside-focused questions—about risk, competition, defensibility, and failure—while white male founders are more often asked upside-focused questions—about scale, vision, and growth potential.

I’ve seen this play out in real life for more than 20 years as a venture capitalist, especially in public pitch forums and live Q&A settings. And while investors rarely think they’re doing this intentionally, the effect on the founder across the table is very real.

The Trap: Treating Every Question as Sacred

One pattern I see over and over is that female and underrepresented founders tend to be extremely conscientious in how they answer questions. They take each one seriously. They assume it deserves a direct, precise, fully reasoned response.

That instinct makes sense.

There’s a real power dynamic at play. Capital feels scarce. Access feels fragile. And if you don’t often feel like you’re in the driver’s seat in rooms like this, the natural reaction is to respond exactly as asked—carefully, thoroughly, and defensively.

The problem is that if you do this for the entire pitch, the conversation slowly drifts away from the most important thing: why this company could be big.

Pre-WritE the Storyline

The founders who navigate this best don’t wait for the Q&A to define the conversation.

They come in with a clear storyline they intend to deliver—and they return to it no matter what they’re asked.

That doesn’t mean dodging questions. It means answering them through the lens of the upside.

For example, let’s say your core thesis is that once customers adopt your product, expansion revenue is the real unlock.

An investor asks:

“This market is crowded. How are you going to cut through?”

A literal answer might spiral into a long explanation of competitive dynamics and go-to-market risk.

A stronger answer sounds more like this:

“We’ve already cut through—we’re seeing strong early adoption and unusually sticky usage. What’s exciting about that is what it enables: once customers are in, we see clear expansion paths that meaningfully grow revenue per account over time.”

You’ve answered the downside question. But you’ve ended on the upside.

Do this consistently and something interesting happens: by the time you’re done reinforcing your growth narrative, the original risk-framed question often fades away. Many of those questions aren’t deeply held objections—they’re habits. If you don’t linger there, neither will the investor.

Stop Trying to Prove You Belong

There’s another pattern that quietly eats up valuable pitch time: founders trying to establish that they deserve to be in the room.

Here’s the reality most people don’t internalize.

Investors see thousands of companies a year. They only take meetings with a small fraction of them—often 10–20%, sometimes less. If you’re sitting in that meeting, you have already cleared an initial bar.

Investors are not in the business of giving pitch practice. They are looking for companies that could return their fund. If they truly believed you were unqualified to build this business, you wouldn’t be there.

Which means this: you do not need to over-qualify yourself at the start of the meeting.

Unless your prior $500M exit is literally the hook, spending your opening minutes walking through a respectable but non-extraordinary career is usually a mistake. That early window is short. That’s where the hook belongs.

Assume you’re qualified. Act as if you belong. Start with the story.

Once you’ve hooked them—once they’re leaning in—that’s the right moment to talk about the team, the capabilities you’ve built, and what you’ll need to add next.

You can’t control the questions you’re asked. But you can control what the investor remembers.

For founders who disproportionately receive downside-focused questions, the goal isn’t to fight the dynamic head-on. It’s to redirect the energy of the conversation—again and again—back to the opportunity.

Write the story in advance. Return to it relentlessly. And don’t spend your limited time in the room trying to prove you deserve to be there.

If you’re in the meeting, you already do.

Most people in venture feel lucky to be there.

At least at first.

Breaking in is hard. The odds are long. And when you finally land the role—associate, senior associate, principal—it can feel like you’ve won the job lottery. You don’t question it. You focus on learning, executing, proving you belong.

But after a few years, once the novelty wears off and you’re past the point of just being grateful to have the seat, a quieter question sometimes creeps in:

Is my firm actually right for me?

Not in a dramatic way. Nothing is obviously broken. The people are smart. The work is interesting. On paper, everything looks fine.

But you start to wonder. About the partner path. About the firm’s long-term trajectory. About whether you’re growing faster than the platform—or whether the platform is growing at all.

And if that question even might have an answer other than yes, a second one follows immediately:

How do I explore that without creating risk for myself?

That’s a tough question. Venture is small. Reputations travel. Signaling disloyalty—even unintentionally—can feel dangerous. And it’s not always obvious who you can talk to without tripping a wire you can’t untrip.

The first thing I tell my venture coaching clients is that moving from one VC firm to another is not a simple job search.

It doesn’t behave like one. It doesn’t follow job-search timelines. And it doesn’t reward job-search behavior.

Firm-to-firm moves are slow by design, because the candidate pool already exists—at least at the senior level. You’re unlikely to get a senior level or partner track position in venture if you don’t already have some investing experience—and that’s a finite pool. Narrow it down to a specific sector and they already know dozens of plausible candidates.

They’ve looked at deals together or competed head-to-head.

It’s extremely unlikely they’re going to ignore all of that context and hire someone simply because that person decides it’s time to look.

Which means the real starting point isn’t who’s hiring.

It’s who already knows you, and what they think of you.

Time to Take Stock in Your Network

I encourage people to start with a brutally honest inventory of their relationships. Who would actually hire you tomorrow if there were a seat? Who would take a serious meeting? Who knows your name but not your work? Who barely knows you exist?

If most of your relationships sit in the middle, that’s not a failure. It usually just means you’re earlier in the process than you think.

But relationship strength alone isn’t the whole story. What matters just as much is how you’re categorized inside other people’s heads.

Every partner you interact with is unconsciously force-ranking you. Not on paper, but mentally. Once that classification sets, it’s surprisingly sticky. Relationships are the input; perception is the output.

The Rankings

At the bottom of that mental ranking are people who technically work in venture but aren’t really considered candidates. They’re seen as executional, with no visible judgment, no ownership, and no independent point of view. These are people who could take a first call if it came to them, but aren’t likely to “find” anything versus just “sort”.

Above that are people who are clearly competent but findable out in the pool. Smart, capable, trustworthy. The kind of person who would do fine in the role, but doesn’t yet bring a clear edge. If they left, the firm could replace them with someone similar and keep moving. That’s not enough to trigger a firm-to-firm hire and risk being seen as poaching.

If I’m going to poach someone from within my circles, they better be more than just “replacement level”.

The first real inflection point is when someone is seen as a good VC currently, and maybe a very good future one, who still needs a platform. At this stage, people think: I’d bet on them, I’m just not sure how much of this is them versus their firm. These people get meetings, or maybe their business card does.

From there, the shift is to independent judgment and reputation. People seek meetings with them. This is when people believe you can originate, not just execute, regardless of what firm they’re at. Co-investors start following you, not just your firm. Founders reference you by name. Other VCs ask what you’re seeing.

Your judgment and network begins to travel.

The next step up is where firm-to-firm moves actually start happening. You’re seen as an outperformer—someone who makes wherever they sit better. You consistently get to things earlier, go deeper in a space than peers bother to, and become associated with a category or insight. This is where speed and depth compound. You’re not louder; you’re earlier, because you’re deeper.

Above that is the moment people sometimes describe sheepishly as: we’d rather have them inside the firm than outside it. Firms follow your writing, show up to what you host, and hear your name from portfolio companies. You’ve flipped the dynamic. You’re no longer pitching yourself; you’re creating pull.

At the very top are people whose names shortcut conversations. They’re associated with a sector, a talent pool, or a way of seeing the market. Hiring them isn’t about filling a role; it’s about acquiring leverage. Rarer still are people who bring true proprietary advantage—deal flow others can’t access, an angel or advisory footprint, pattern recognition built through ownership. At that point, the ROI is immediate.

To recruit or Not to Recruit?

I’m skeptical of recruiters at the senior end of the market.

Once you’re in principal-to-partner territory, if you need a recruiter to find you a role—or a firm needs a recruiter to find you—you’re often already starting at a disadvantage. Joining an existing partnership without pre-existing trust is incredibly hard. The best firms don’t need help identifying talent. They’ve been tracking peers and up-and-comers for years, and they have the gravitas to pull someone out of a seat they already occupy.

That doesn’t mean recruiters are useless. This advice doesn’t apply the same way to associates or other junior folks, and it only partially applies to principals. But the more senior you get, the more relationship-led these moves become.

A venture recruiter should be additive, not foundational. Talk to them to get a sense of the market, comp, and which firms are expanding—but your best shot at landing those firms is if you already know them.

Party Fouls

There’s one other practical point I emphasize in coaching, because people underestimate it: try very hard not to get caught looking.

Once it becomes clear inside your current firm that you’re actively exploring, your timeline accelerates whether you want it to or not. Even well-intentioned partners start planning around the possibility that you might leave. You may stop getting pulled into certain conversations. The firm may quietly begin hedging. At that point, the move is no longer fully on your terms.

This doesn’t mean being secretive or dishonest. It means being intentional. Build relationships, do great work, share projects, and explore alignment before you signal intent. The strongest firm-to-firm moves happen when you still have leverage—when staying is a real option, not a shrinking one.

Is moving Worth It?

Another thing people underestimate is how hard it is to verify whether the grass is actually greener.

Everyone puts their best foot forward during a hiring process. You don’t see the cracks right away. You see them six months in, or a year in, when incentives, personalities, and firm math start to reveal themselves.

If the firm you’re considering has been around for a while, your best source of truth usually isn’t the current partners trying to hire you. It’s someone who used to work there. Former principals. Former partners. People who left without drama. Those conversations will tell you far more about how a firm actually operates than any interview process ever will.

It’s also worth naming that many people don’t leave firms because they want to. They leave because the firm itself is winding down or structurally changing. In those cases, searches are often conducted with transparency and partnership support. Those aren’t failures. They’re reminders that firm-to-firm moves are often driven by circumstance, not ambition.

What people consistently get wrong is thinking these moves hinge on timing, optics, or saying the right thing.

They don’t.

They hinge on where you already sit in other people’s heads. You don’t get ranked higher because you declare readiness. You get ranked higher because people already have evidence.

Put Me In Coach

There’s also a specific anxiety that comes up here that’s worth addressing head-on: the fear that switching firms is a negative signal.

In practice, it usually isn’t.

Firms don’t grow linearly, and partner seats don’t magically appear. Sometimes a firm simply has the right number of partners for its size, and that’s it. I often use a baseball analogy when coaching people through this. You can be a top-tier rookie and still be blocked by an All-Star who plays the same position. There’s nowhere to go. In baseball, that player gets traded from a position of strength to a position of need. Venture doesn’t have trades — but the dynamic is the same. Blocked is blocked. And that’s structural, not personal.

Good firms understand this. In many cases, a thoughtful move is actually read as self-awareness, not failure — especially when it’s paired with strong references and a clear track record. Staying in a seat with no path out of loyalty or fear rarely improves how you’re perceived.

That’s why outperforming matters, and why it has to be visible. Outperforming doesn’t mean being busy. It means being ahead. In practice, it comes down to speed and depth. Depth lets you see things earlier: talent before it’s obvious, teams before they’re fundraising, patterns before they’re consensus. That’s where most top-tier firms don’t have time to go—and where ambitious senior people can stand out.

A common mistake is waiting until you’re “looking” to become visible. That’s backwards. The strongest moves happen when firms find themselves following you—reading your work, hearing about what you’re building, repeatedly running into you in deals. At some point the thought flips from interesting to we should probably be on the same side of the table.

People also overthink the first real conversation. They worry about sounding eager or saying the wrong thing. In reality, most outcomes aren’t that fragile. If there’s real alignment, it shows. The best framing is usually honest and direct: you admire how they think, you feel aligned with their values, and you’d love to explore whether there’s a way to be helpful. Good firms don’t recoil from that; they appreciate it.

More often than not, the immediate answer isn’t a job. It’s let’s do a deal together. That’s not a no. That’s the path. Working together builds trust faster than any interview process ever will.

Finally, a word on economics. Carry, clawbacks, and restrictive clauses matter, but behavior matters more. I’ve seen aggressive and vindictive exit behavior. I’ve also seen thoughtful, professional transitions. How a firm handles your departure is a culture tell. If a firm can only keep people through golden handcuffs rather than admiration, alignment, and opportunity, that’s worth paying attention to.

The question I leave people with is simple: if someone evaluated you tomorrow, what concrete evidence would they have that you operate at the next level—without your current firm’s brand doing the work for you?

If you can answer that clearly, you’re probably closer than you think.

If you can’t, that’s not a failure.

It’s a roadmap.

This is Going to Big Big is written since 2004 by Charlie O’Donnell, former VC and current coach to active and aspiring venture professionals and professional pitch deck skeptic.

One of the lessons I’ve learned over two decades in venture—one I genuinely regret not internalizing earlier—is that I spent far too long trying to meet everyone.

In this industry, the more you put yourself out there, the more the world pushes back with opportunities. A blog post hits, a tweet goes viral, you speak at a conference—and suddenly you're inundated. Founders, operators, students, service providers, “Let me show you want I’m working on” DMs. It becomes an unending parade of people you could talk to.

And the mistake most VCs make—especially early in their careers—is confusing volume with progress. Just because you’re taking all the meetings doesn’t mean you’re closer to finding the next big thing.

It’s the same magical thinking as a baseball player believing they could, in theory, hit a home run on any pitch. Sure—anything could happen. But that’s not how plate discipline works. Some pitches are simply more hittable. Some have a massively higher probability of leaving the park.

The real question is: are you structuring your calendar around the pitches that give you the highest probability of success?

Who Asked for Those Meetings?

Try this simple diagnostic:

How many meetings on your calendar this week are there because someone asked you…
versus because you asked them?

If you’re honest, the ratio is probably not where you want it to be.

Inbound meetings are easy.
- They’re flattering.
- They’re available.
- Take enough of them and they will probably pull you toward the median.

Outbound meetings—the ones you initiate—tend to come from intention.
- They reflect curiosity, hypothesis, and strategy.
- They represent people you believe have:

• better-than-average networks

• better-than-average chances of success

• domain expertise you can’t get anywhere else

• or simply a track record that skews outcomes upward

Those are top-quartile meetings. And top-quartile meetings are what drive top-quartile fund performance.

VC Time Is Finite. Meeting Quality Is Not.

This business has a built-in illusion: more meetings = more shots on goal. But in reality, you don’t have infinite shots. You have finite hours.

Every meeting you take displaces another one you could have taken—or one you could have proactively sought out.

Start scoring your meetings the same way you score anything else:

• Did this meeting have a better than average chance of resulting in a high-quality opportunity?

• Did it move your thesis forward?

• Did it expose you to real insight rather than generic “spray and pray” ideation?

• Was this the best possible use of that hour compared to the meetings you could have sourced?

If not, that hour was expensive.

Take a concrete example.

Who would you rather take your next meeting with?

1. A cold inbound from a random founder who “invented a new payment solution” coming out of their Harvard MBA program that has a consulting background, or…

2. The most interesting person you could find in a list of early Stripe alumni—people who have lived inside one of the highest-leverage fintech ecosystems on the planet, who know where the bodies are buried, who understand the infrastructure gaps, who have seen world-class execution firsthand.

Which path gives you a higher likelihood of finding an extraordinary founder doing something truly new? Who is more likely to both identify a legitimate opportunity and attract the talent to go after it? Someone who has the Ivy credentials or someone who could name ten people they worked with at a generational fintech company they’d hire the day the funding closed?

Even if that Stripe alum isn't starting something new, she might be a great co-founder to that recent business school grad who decided they wanted to be a founder before they sought out a problem to solve.

The call to selectivity might sound like gatekeeping, but I would argue that being more intentional about your calendar increases selectivity. Instead of just relying on the kinds of inbound your existing network happens to put in front of you—and given that our networks tend to look both physically and on a resume quite like ourselves, you know that that means—investors should be more thoughtful about who winds up on their calendar.

The Risk of Overcorrecting

This advice can sound like a call to narrow too early. That’s not what I’m arguing. Early exposure is how you develop taste and judgment — focus just ensures that exposure compounds instead of diffusing.

Refactor

Stop believing you’re “missing out” by not taking every meeting. You’re actually missing out by taking too many of them—because they crowd out the high-probability conversations.

Your calendar is not a to-do list.
- It’s an asset allocation.
- It’s exposure management.
- It’s a statement of your strategy.

If you want better outcomes, you need better meetings. And better meetings come from focus, not volume.

I suggested to one of my coaching clients that they cancel the worst meeting on their calendar every week--the one where they're the least excited to meet the founders, and replace it with someone from a list of formerly exited founders in the spaces she cared about.

Within a month, she had a lead on her first deal from those latter meetings.

Refactor your calendar.
- Shift the ratio from inbound to intentional.
- Stack your time with people who genuinely increase your chance of success--that you're really excited to meet.

The biggest unlock isn’t finding more founders. It’s finding the right founders—and making sure you actually have time for them.

Have a rubric for what gets a meeting from you—relevance to your thesis, potential for learning, or perhaps the source.

Who has leant their creditability to this intro and do they lend it sparingly or widely?

Some folks might worry that cancelling a meeting or saying no to an intro might be rude. In my experience, leaning on respect for the other person’s time is always the way to go. If you don’t have the right level of enthusiasm or interest in a meeting, it’s actually best that you give someone their time back.

Along the same lines, I often deflect introductions with a thoughtfully written e-mail that, while it takes me a few minutes to write, takes me far less time than a full meeting would have taken.

Without intention, especially as a venture investor, your time budget will quickly run out and you’ll be left wondering why everyone else seems so much better prepared to find that next big opportunity even though you’ve all been working equally hard.

This is Going to Big Big is written by Charlie O’Donnell, former VC and current coach to venture professionals and those trying to break in, and professional pitch deck skeptic.

I recently got hit up for a backchannel reference on a founder I had backed. His company didn’t return anything to investors when it got sold, and I hadn’t heard from him after the sale—so I didn’t know about the new company.

It’s perfectly reasonable to feel a bit awkward after you’ve lost someone’s money, regardless of whether they’re an individual angel or a venture capital investor. Just because it isn’t technically a VC’s own money wouldn’t make it any less of a black eye within their firm, right?

The follow-up after a loss might not be a conversation you’re excited to have—but it’s the best thing you can do for your reputation and your growth. Here’s how to have that conversation so these loose ends don’t come back to bite you.

What do I mean by that?

Well, it’s a bit awkward to have to respond to a reference check with, “I haven’t heard from them, so I don’t know anything about this new company.” That’s going to make the new potential investor wonder if maybe you left on bad terms or whether the founder has any reason to think I wouldn’t want to speak with them.

That’s the funny thing—most founders wouldn’t imagine I’d want to chat with them after they lost my fund’s money, but as long as they worked hard and did their best, why wouldn’t I? Every startup investor knows going in that the chances of success are going to be low. Do founders really think that VCs just have a broken relationship with the founders that don’t make a big return—which is most of them? That would be a lot of unnecessary bad blood out there, especially since the majority of people aren’t stealing from the company or moving to Fiji to kick it on the beach with the money.

When you were in the trenches with a founder, watching them fight tooth and nail to make something of your investment, you’ve gained a ton of respect—more than you could ever lose with a negative financial outcome. The idea that they’d rather back a complete stranger than work with you again doesn’t square with how they invest. They asked their own investors to give them 30 or 40 shots on goal because they know the first one, two, three, or twenty might not work out.

Could you imagine if their investors cut them off after one bad deal?

I’m not saying every VC will be thrilled to talk to you after a loss—but you can’t control what they think about your past performance. You can only impact the relationship going forward—and just leaving the loop unclosed isn’t the best way to handle it no matter what they think of you.

Let’s assume the worst—they think you’re a total loser. (I guess that’s the second worst. Let’s hope they don’t think you’re a crook because of actual theft. That’s probably unrecoverable.)

Maybe nothing will change the fact that they think you’re unbackable, but wouldn’t you rather follow up with them and tell them everything you learned about the experience and what you could have done better? I’m not saying grovel and self-flagellate. I’m talking about a fair critique and self-assessment.

You could come back with something like, “I just wanted to say I appreciated your support and that I’ve been thinking about my performance as a founder. I think I should have done more of A and B and less of C. C didn’t quite provide the returns given the amount of time I spent on that, and I think I could have realized that earlier if I paid more attention to it. Do you think that’s fair? I’m curious if there’s anything else you noticed that would serve me well the next time I do this.”

You could even weave a pitch for the new company into the request for feedback (as they say… “Ask for advice…”).

“This will be particularly important given what I’m working on now. We’ve seen an opportunity to take advantage of X disruption to a Y billion dollar market, and I’m going to need to be much better at A and B if we’re going to make this work.”

If the new company is in their wheelhouse and they’d ever consider backing you again, they’ll inquire now.

If they don’t want to back you again, at least if someone asks, they might not be so quick to say, “This guy was a total loser and I’d never back him again.”

Wouldn’t you rather they say something like, “Yeah, you know, I just spoke with him, and I think he learned a lot from the first time around—and yeah, the new company is interesting.”

Another reason why you should be reaching out to all of your prior investors postmortem is to weed out any unresolved issues. If anyone does have a problem with you—you’d rather know it than have rumors of your incompetence or malfeasance kneecapping your new raise.

Is it likely that anyone’s going to reach back out to your prior investors? 100%.

They’d be remiss not to.

Obviously, in the best of all cases, your prior investors can’t wait to see the next hard thing you attempt and want to give you money again. Even if only a handful of them do, that speaks volumes.

If they don’t, wouldn’t you want to know why?

Wouldn’t you rather hear it from them and get a chance to address the criticism?

Just ask directly: “If this was in your wheelhouse, is there any reason you’d hesitate to back me as a founder again? How would you advocate for me to your team? Would there be any fair criticism you’d have trouble addressing?”

Everyone knows the risks when you start a company or invest in one—and the best founders cultivate relationships that transcend financial outcomes through clear, honest communication and acceptance of fair feedback.