We have a bias in entrepreneurship toward successful people. We want advice from founders who made it, investors who backed winners, executives who led companies to meaningful outcomes. The logic makes obvious sense — learn from people who’ve done what you’re trying to do.

But about two years ago I had a conversation with someone whose company didn’t make it. He’d built a B2B software startup, raised a seed round, got to about eight employees and $400K in ARR, and then ran out of runway when a second funding round didn’t come together. He shut down the company about eight months before we talked. And the conversation I had with him was more useful than most of the success-story conversations I’ve had, because he was able to be honest in a way that most people building toward something can’t be while they’re still in it.

What He Said

We were talking about customer conversations — specifically, about how he’d handled them in the early days of his company. And he said something I’ve thought about many times since: “I spent the first eighteen months listening for confirmation that I was right. I should have been listening for evidence that I was wrong.”

He expanded on it. When he talked to customers or prospects, he was listening for the signals that validated his thesis — the pain points he’d built his product to solve, the feature requests that matched his roadmap, the enthusiasm that confirmed the market was real. He was doing what most founders do: seeking evidence that they’re on the right track. And he was good enough at the product and good enough at the conversation that he found plenty of that evidence.

What he was filtering out — unconsciously, not deliberately — was the contradictory evidence. The customers who thought the product was interesting but didn’t change their behavior when it was available. The prospects who said “we’d love something like this” but couldn’t articulate a specific situation where they’d actually use it. The churned customers whose stated reason was “wasn’t the right fit” but whose real reason, on honest reflection, was that the problem wasn’t painful enough to justify the switching cost.

Why This Hit Me Hard

I recognized myself in what he was describing immediately. When I’m in a conversation with a prospect who’s engaging with the AEO concept, I feel the pull toward the confirming signals — the “this makes sense” moments, the “I can see why this would matter” acknowledgments. Those signals feel like progress. And they might be. But they’re not proof of anything. Someone finding your thesis interesting is not the same as them having a problem painful enough to pay to solve.

What my failed-founder friend was really describing was a discipline of deliberate disconfirmation — actively looking for the evidence that would prove you wrong, rather than passively accumulating the evidence that proves you right. It’s harder than it sounds. Humans are not naturally built for it. We’re built to find patterns that confirm what we already believe. Deliberately looking for the contradicting patterns requires overriding an instinct that’s usually useful.

How I’ve Tried to Apply It

Since that conversation, I’ve tried to build disconfirmation moments into my process deliberately. After a prospect call that feels good, I make myself ask: what did they say that didn’t support my thesis? What questions didn’t they ask that I would expect an interested buyer to ask? What enthusiasm might have been politeness rather than genuine intent? I don’t always find the contradicting signals. But looking for them has made me sharper at distinguishing real signals from noise, and it’s made me faster at noticing when something isn’t working before it has become a serious problem.

I don’t think my friend failed because he was a bad founder. I think he failed because he was a normal founder — one who, like most of us, had a harder time holding space for evidence that contradicted what he’d invested so much in believing. The discipline of active disconfirmation is hard precisely because it asks you to take seriously the possibility that you’re wrong about something you care deeply about being right about. That’s uncomfortable work. But it’s the work that tends to separate the founders who catch problems in time to fix them from the ones who discover them too late.

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