By Chris Heivly, Managing Director at Build The Fort and Startup Community EIR @ Techstars

Let me tell you something you probably won’t hear too often from a well-known business tycoon or from a new founder on a startup pitch stage: “I know what I’m doing, and I’ve made a ton of mistakes.” A founder said this to me a few weeks ago, and it really resonated with me.

Those two ideas might feel like they don’t belong in the same sentence. Like oil and water or apples and oranges. But in startup life, they not only coexist — they have to. It just might be equivalent to an entrepreneurial theorem.

Look, confidence is critical. As a founder, community builder, or frankly any type of leader, you’ve got to project enough belief that others want to get in the boat with you. But if that confidence isn’t tempered by a solid dose of humility, you’re not learning. And if you’re not learning, you’re going to hit a wall — fast.

Every mistake I’ve made (and I’ve got a greatest hits album of them) has taught me something I couldn’t have gotten from Google (and now Perplexity). I’ve hired the wrong people, chased the wrong metrics, and stubbornly waited too long to pivot away from the very vision I sold to my team. But I’ve also learned how to recognize those previous flaws as well as talking about them in public with the aim of showing up vulnerable over showing up polished.

The trick is to hold both truths in your hands at the same time. You can know what you’re doing — based on battle scars and reps — while still screwing up in new ways. That’s not failure. That’s growth. That’s the real founder journey.

The founder’s two truths: you’ve got the confidence to lead and the public scar tissue to prove you’ve learned everything the hard way.

So here’s my message to you: Don’t trust the person who claims to have all the answers. Trust the one who admits where they’ve blown it — and tells you what they’d do differently next time.

Startup life isn’t a clean, linear arc upward. It’s a squiggly mess of bold bets, missed shots, and the occasional home run. If you're feeling like you're just winging it most days, congrats — you're doing it right.

Because in this game, the only people who actually know what they’re doing… are the ones who’ve made enough mistakes to earn that confidence.

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