Of all the lessons I've been revisiting from the Strongroom era, this is the one I'm most confident AI will never fully solve. Sure, LinkedIn can surface anyone. AI can write your cold email in seconds. A warm intro is a shared connection and a quick message away. But building valuable connections — real relationships — requires trust, and I'll always maintain that trust cannot be built without some face-to-face time.
I went to a conference in Palm Springs last April, and it was just the latest reminder of why this is still a critical ingredient of a founder's diet.
The event was called the Recast Retreat — a small gathering for emerging fund managers and LPs. Despite my anxiety about these events, I'm glad I forced myself into a potentially uncomfortable situation. What I found was two days of conversations I couldn't have manufactured from a desk — fund managers thinking about capital in ways I hadn't been exposed to. Real connections. Real exchanges. And at one point, a colorful smock. That last part matters more than it sounds.
For someone who has spent years telling founders to network more, I should be honest: walking into a room where I don't know anyone still produces real anxiety. Most founders I've talked to feel some version of it — they just don't say it out loud. So here I am, saying it out loud.
The serendipity that changed everything
In 2006, we were in the throes of finding Product Market Fit — no income, a product that wasn't quite right, and a runway that was getting shorter by the month. What changed things wasn't a pitch deck or a spreadsheet. It was networking.
We had built a relationship with a lockbox payments company that moved in adjacent waters. They had a bank client looking for an accounts payable solution for one of their most important clients. We got connected. And after a few weeks, we had an agreement with the bank to deliver a pared-down version of what we had been working on, and they would give us $12,000 to help get it done.
That $12K deal became the foundation of Strongroom's entire direction — not because of what it paid, but because of what it unlocked.
It was a chain of conversations that started with us just being in the right rooms. That's the story behind the lesson. Serendipity got us there. But serendipity only shows up when you're already out there.
So does it still hold in 2026?
This is the question I'm asking across all of these posts — and it's worth asking honestly, not just as a rhetorical setup. AI has genuinely changed what it means to start a tech company. Some lessons from the Strongroom era got easier. Some got obsolete. And some — like this one — turned out to be more durable than I expected, but for reasons that shifted.
Here's the fair version of the challenge: LinkedIn has turned "networking" into a verb that mostly means sending connection requests to strangers, and AI can now write your cold email in seconds. So is the lesson just a relic from a slower era?
Some of the structural barriers genuinely got easier. You can find the right person in minutes. You can research a shared connection and get a warm intro with half the friction it used to take. Cold outreach has never been faster or cheaper to scale.
And look — if your 2006 problem was "I can't find the right people to be in a room with," today's tools solve that. That's real.
But here's what didn't change
A DM isn't a relationship. The part of networking that actually moves things — the serendipitous conversation, the unexpected introduction, the moment someone decides to go to bat for you — still requires physical presence, vulnerability, and a willingness to be genuinely uncomfortable.
You can use AI to draft the perfect cold email. You can't use AI to do the uncomfortable work of actually showing up. The tools made finding people easier. They didn't make connecting with them easier.
Which brings me back to the colorful smock. That was me at a conference full of people I'd never normally be in a room with, doing something I'd never normally do, having conversations that are still paying off weeks later. That's not a story about networking strategy. It's a story about saying yes to the uncomfortable thing and trusting that something interesting will happen.
The Learnings
- Learn to be uncomfortable. The anxiety at the door doesn't go away — you just get better at walking through it. It's a skill built by reps. The best relationship-builders I know aren't the loudest people in the room. They just kept showing up.
- Be yourself, not a performance. People feel a polished pitch. The connections that turned into something — real deals, real partners, real advocates — were built on genuine curiosity and real conversation. Authenticity scales in ways performance doesn't. And trying to be something you're not in a room full of strangers is exhausting on top of everything else.
- It comes in more forms than you think. A cold email that got a reply. A mutual intro. A comment thread that became a coffee. An invitation to a conference where you'd definitely feel like an outsider. Don't write off networking because one form doesn't fit — find the version that works for you. Just know that you still have to put yourself out there for any of it to happen.
So I'd rewrite the lesson for today: you don't need to be a natural networker. You need to be a willing one. Find the room that's a little uncomfortable. Stay long enough to have the real conversation. Use the tools to find the right people faster — but don't let the tools replace the showing up.
The algorithm doesn't do uncomfortable. That part's still on you.