How to raise a seed round after 170+ investor rejections

It's Sunday and Andrew and I are getting ready for an investor meeting tomorrow. Andrew's given this talk about 50 times to the teams he helps prepare, so we thought — why not make it a podcast everyone can take value from?

I'm wearing a bathrobe, I just went on my run, so this is raw. This is a presentation I've given 50-plus times — as a mentor at Techstars, 500 Global, and countless panels with early-stage founders getting ready for their first raise. It's built off what I did to raise a $4 million seed in 2021–22. I like it because the approach is universal — it's a human-to-human thing: human psychology, human trust, and running a really clean process.

What's the one thing 90% of founders get wrong before an investor call? For me it was thinking the coolest deck in the world would separate me — I was dead wrong.

The deck is not that important. What investors want is energy and passion — but measured. Keep it minimal, especially the first couple of interactions. You're not selling with data; it's not a data dump. You're triggering an emotion: this is potentially going to be enormous, and I have an opportunity to get involved now that won't last forever. And it has to be true — a genuinely big, category-defining opportunity that's moving quickly. Under ten minutes you have to tell the story in a way that triggers that feeling. Everything else just supports it — and if you overdo the other things, it damages it.

The biggest enemy is apathy — the audience checking their phone. So I architected the whole thing as an organic conversation. The blueprint: the first ten minutes is introductions. It's human to human — you meet these people, ask about their firm, their career, their wins and losses, their expertise. People like to talk about themselves, and it lets them give you the hero version of themselves. A lot of people skip this. Don't. Then you introduce yourself — no slides — and tell the story of your career in a careful way that threads the needle: you're incredibly capable, and you happened to be in the right place to see this enormous opening in the economy.

Your intro should flow naturally into the company: my career led me to this discovery, and the discovery was so enormous we had to start this business. Then you cue in your co-founders as the perfect puzzle pieces. Only then do you screen-share. The core deck should take five to seven minutes — logo, the manual insight that worked, the breakthrough, one happy customer, a little traction, a very simple market slide. These are 20-second slides. You're just getting through it.

What do you do when the investor's eyes glaze over — when you feel like you're boring them?

Usually that only happens if you're monologuing and taking up too much air. It's a signal. Throw it back to them: does this match what you're seeing? What interests you about this space? Why did you take this call? Let them talk — let them feel smart again. It's an ego interplay. Conversations are not one person talking for twenty minutes.

The reason the simple version works: while you talk, the VC is a professional hole-poker — their whole career is meeting hundreds of founders and saying no. So hit them with a simplified 'we're going to be a billion-dollar company,' and let them poke holes. We'd had dozens of these calls, so we knew exactly what the holes would be, and we had 25 appendix slides — an answer to everything. 'Why didn't you think about X?' 'Yep, here's the competitive landscape.' Give them a little tummy rub — great question — then boom, the answer. The reverse, cramming all the data into a perfect 13-slide deck, failed every time, because we were just talking and they never got to show how smart they were.

It comes down to who's driving the bus — and VCs are bad bus drivers. Let them drive only as far as reasonable: if they need to see something in the data room, it's ready. But you run the process. If it's too early for them, don't get depressed — just mark it a no and keep in touch for the Series A. You can't leave it open-ended or it drags out forever.

Urgency is private — the round, the info, all of it. I'm not a fan of stretching the truth, and a lot of founders do. But you don't win by giving them more than two weeks. It's more like: let me know by next Wednesday if you even want a second discussion. You can gently say we've already closed a portion, we have appetite, I have twenty of these meetings this week — but this is now-or-never. VCs snap into muscle memory when it's decisive; if you leave it squishy, they don't.

For prospecting we went introductions only — nothing cold. We built a list of about 230 investors from lists like SignalFire, NFX and AngelList, filtered broadly for early/seed and sales tech. Then, for each one, I put their LinkedIn in and looked at mutual connections — who could introduce me. This part had to be manual, because only the founder knows which mutuals they're actually close to. And we tiered them, doing tier 3s first, because you get better as you go.

What we realized was that most of the good connectors narrowed down to about a dozen people who each knew five or ten of the targets. So I flipped the sheet and made the connectors the star. Here's the counterintuitive part: most founders immediately ask a friend 'introduce me to so-and-so' — that's rude and it doesn't work, because you're asking them to burn their social capital on something they don't even know about.

The hack: everybody loves being asked to do a practice pitch. They're flattered, curious, in a position of power, no prep. So we did a real pitch — with real gravity — with every frequent connector. The first couple, we sucked and got feedback. Two or three in, they'd say 'this is amazing, you should meet so-and-so' — we didn't have to ask. Some put money in right away. Once we got good, every practice pitch turned into a genuine warm intro, even from investors.

The gauntlet was brutal — of 223 targets we got to 105 intros, 77 meetings, and a wall of nos. Halfway through I thought, to hell with it, and started asking every 'no' for a ten-minute debrief. Every one was excited to do it — they liked you, they were rooting for you, and now they got to give insight. Most reasons for the no weren't about me — the fund was low on cash, or a competitor, or timing. And they remember you as a real human forever, instead of another face on the subway. The nos gave us some of our best intros — including people who later wired money.

Then one investor came in heavy — $1.5 million, most of the round. At that point we told everyone we only had $700K of space left, and it was a feeding frenzy. We closed the last $700K at a valuation 40% higher than the lead. It's the same company — the market dynamics changed, like a stock price moving on news.

Safe notes changed the game. A safe is future equity — they send cash, no debt, no shares, and it converts at your priced round. It's private and unilateral, so you can set different terms with different people the same day, usually a post-money cap: invest a million at a $10M cap and you get 10% if they raise above it. We did a rolling close — first $500K at a lower cap, then higher as it got safer. That's completely fair: earlier money took more risk.

One thing I wish I'd known: this is a go-for-broke market — you're shooting for the billion-dollar outcome, and it has to be real. If that's not your profile, there's no shame in bootstrapping a great, profitable business; I built an eight-figure services company with no money. But if you're doing the VC thing, look like a VC company and really mean it. Good luck out there.