A recap of our fireside chat with Charlie O’Donnell, founder of Brooklyn Bridge Ventures and author of Founder Unfriendly
We invited Charlie O’Donnell to join us for one reason: pull back the curtain. No polished talking points. No “founder friendly” performance. Just the uncomfortable, useful truth about how investment decisions actually get made. And girl, did he deliver!
Charlie’s approach was an unapologetic push for founders to take ownership and control. From his point of view, it matters less why VCs act a certain way, what matters is what founders decide to do about it. At one point, Leslie Feinzaig called “Founder Unfriendly” the “Lean In” of fundraising advice books – the system might be stacked against you, but you have to go for broke regardless.
Charlie started with helpful VC context. When you’re seeing 2,000 deals a year and writing five checks, you use proxies. You trust the team from a known shop. You take the warm intro over the cold email. Charlie’s babysitter analogy landed hard: if a parent you trust recommends their sitter, you skip the background check. You extend trust because someone you trust extended it first. VCs operate the same way — it’s rational, it’s fast, and it shapes who gets a meeting. Understanding that is the first step to working around it.
From there, the conversation turned to what founders actually do in those meetings. 80 to 90 percent of your pitch has to be about where you’re going. The check is a bet on future execution, full stop. Your traction, your early customers, your scrappy wins to date — those are evidence. Evidence that you might be able to pull off the real story: here’s where this goes, here’s how big it gets, here’s why I’m the one to take it there. Lead with your destination. Everything else is context.
And once you’re in the room, be clear-eyed about what you’re hearing on the way out. “Watching you.” “Staying in touch.” “Really interesting.” These are passes. A VC who wanted to invest could have invested before you proved anything, when your equity was cheap. They chose not to and that is valuable information. If you don’t hear an honest reason, it’s your job to extract one. Structure your pitch like a sales conversation — state your goals up front, and at the end, ask whether you hit them. Less than 1% of founders do this, which means the ones who do stand out immediately.
The most layered part of the conversation was about bias. Charlie spoke openly about what he carries into rooms with female founders — the socialized assumption that women are less likely to swing for the fences. He doesn’t deny it – he’s working on it. But for female founders, it’s a safe assumption when you’re pitching an investor that they may share some of this bias – that’s the world we have to face. This means that if you’re going for a big outcome, you have say so explicitly. Put the hockey stick in the deck. Name the IPO potential. Say what this company could become. If you leave it unsaid, VCs will fill in the blank with their own assumptions — and those assumptions were shaped by a world that has rarely looked like you. The hour-long conversation was full of uncomfortable gems – and you can watch the full thing here.
