Analyzing 13 Years of My Investing History: Part Three

In Part 1 and Part 2, I looked at the numbers – valuations, forecasts, returns. Today, I’m looking at the people.

I went back and tagged the founders I’ve backed with a few attributes: first-time vs. repeat, technical vs. sales, and “insider” (industry veteran) vs. “outsider.”

The data challenged two of my strongest prior beliefs.

I tend to love the “industry expert” – the founder with 15 years in supply chain logistics building the next-generation logistics platform. I think a lot about founder–business fit and the why this founder question.

But the data tells a more complicated story.

My biggest outliers – the 50x+ outcomes – disproportionately came from naive outsiders. Not because expertise is bad, but because deep industry knowledge can come with a hidden cost: the inability to imagine something fundamentally different.

The insiders knew how the system worked. They built better versions of what already existed. The outsiders didn’t know what was “impossible.”

The takeaway for me isn’t that domain expertise is useless, but that in the earliest stages, the curse of knowledge is real. We sometimes refer to this as “incumbency bias.” Naiveté can be an asset, provided it’s paired with obsession and a willingness to learn fast.

The second surprise was around storytelling.

We talk a lot about product-led growth, technical moats, and first principles. But when I looked at the companies that survived the Seed-to–Series A slog, one pattern kept showing up.

The founder could tell a compelling story.

I’ve seen brilliant technical founders who couldn’t quite capture belief long enough to raise the capital needed to get lift-off. And I’ve seen founders with average early products build extraordinary companies because they could raise belief – from employees, investors, and customers – even before there was clarity, when the data alone wasn’t enough.

Finally, there’s what I loosely labeled “the chip.”

This one is hardest to quantify, and I’m the least certain about it. But I tried to track something like hunger – how badly the founder needed this to work.

I saw slight underperformance from very comfortable repeat founders coming off massive exits. Many hired faster, spent earlier on brand, and felt less urgency. My best performers were often first-time founders, or repeat founders with a more modest prior exit who felt they still had something to prove.

None of this is definitive. We’re in the business of exceptions but they’re useful guideposts for my next decade of investing.