The Brooklyn Bridge Ventures founder visited Startup School to talk about what school doesn’t teach you, and how to build the connections that actually matter.

Here’s a tension most entrepreneurship courses don’t address: the curriculum tells you the stages, the frameworks, the playbook. But anyone who has actually built something will tell you the process is a lot blurrier than that. Charlie O’Donnell (Courant Faculty), founder of Brooklyn Bridge Ventures and one of New York’s most connected early-stage investors, came to Startup School to talk about exactly that gap, and what to do about it.

“The process is a lot blurrier than school makes it look. Your job isn’t to follow a clear path: it’s to keep moving through the fog.”

ON NETWORKING

Stop asking “can this person get me a job?”

Charlie started his career at GM’s pension fund before making his way to roles where he’d rub shoulders with partners at Carlyle and Blackstone. At the time, his reaction was simple: I don’t want to be the PE guy, so what’s the point of this connection?

Years later, when he was raising his own fund, the KKR contact who could write a $200M check would have been an extraordinary relationship. The 22-year-old version of him had written off the exact person the 35-year-old version needed most.

CHARLIE’S TAKE  

When you’re young and meeting senior people, you have a kind of permission that disappears later, you can ask them almost anything. Take advantage of it. The person you met twenty years ago could become an LP, an angel, an advisor, or a customer. Build a rainy-day fund of people: who has capital, who has reach, who seems like a reasonable human being.

Connections to capital are useful even when you can’t see why yet. When you start as a VC associate, nobody expects you to raise money. But by the time you’re a principal, those relationships become essential, and you’ll wish you’d started collecting them a decade earlier.

ON STAYING IN TOUCH

So how do you actually do it?

This is where most people fall flat. They meet someone interesting, send a LinkedIn connection request with no note, and figure they’ll follow up “someday.” Someday doesn’t come.

Charlie’s prescription is straightforward: customize your outreach, make an ask or say something specific, and keep it up. Cold outreach, done well, goes a long way, and most people are too intimidated to do it at all, which means the bar is lower than you think. If you assume someone won’t reply, plenty of others are assuming the same thing and also not reaching out. That’s your opening.

THE HEARTBEAT EMAIL  

Charlie sends a regular email every 8-12 weeks, a simple update on what he’s working on, what he’s thinking about, sometimes a mix of personal stuff. You don’t need a startup to do this. You just need to tell people what you’re up to. One of his newsletters mentioned he was training for a triathlon; a connection he’d been trying to cultivate turned out to be a swim dad, and that one personal detail opened up a relationship nothing professional could have.

The concept behind all of this is Dunbar’s number, the cognitive limit on how many stable social relationships a person can maintain. Charlie isn’t trying to circumvent that limit. He’s trying to make sure the right people are inside it when it matters.

ON BUILDING IN A BLURRY WORLD

Your edge isn’t the idea. It’s how well you know the market.

Charlie used Strava as a thought experiment. Don’t start by wanting to build a Strava competitor. Start by mapping the ecosystem, understand the players, the gaps, where value is actually created. The goal isn’t to copy the leader; it’s to understand the terrain better than anyone else.

1.     Map the ecosystem first. Map the ecosystem first. Before you build anything, understand who already exists, what they do well, and where the real friction is.

2.     The worst case is rarely as bad as you think. The worst case is rarely as bad as you think. Fear of rejection or failure is usually disproportionate to the actual downside. Most conversations, emails, and introductions cost nothing.

3.     If you know how someone works, it’s easier to back them. If you know how someone works, it’s easier to back them. Investors don’t just fund ideas, they fund people. The more others can observe how you think and operate over time, the easier it becomes for them to bet on you.

4.     Be generous, consistently. Be generous, consistently. Comment, share, make introductions, invite people to things. Always ask yourself: is what I’m about to do likely to make me the go-to person for this thing?

TAKEAWAY

Yes, and.

Charlie’s session wasn’t a lecture in the traditional sense, it was closer to watching someone think out loud about twenty years of compounding decisions, relationships, and small bets. The throughline: stay curious, be generous, and play the long game. The path is blurry, but the people you meet along the way end up being the map.

He also time-shifts a lot, using AI to interview him on runs or in the car, then turning that into content and insight. The medium changes. The habit of reflection and sharing doesn’t.