The Debate People
Last night over dinner, someone asked a question that hit close to home:
“Would you rather build a company with a 60-year-old serial entrepreneur… or a 22-year-old Thiel Fellow?”
I’ve been the hungry 20-something trying to break the pattern. I’ve also been the older founder who knows exactly where the landmines are buried.
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The 60-year-old has pattern recognition.
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The 22-year-old brings pattern-breaking.
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One has scars. One has hunger.
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One knows what kills companies. One doesn’t yet know what’s “impossible”—and that’s an edge.
We tossed examples back and forth—Zuckerberg at 19, the Collison brothers at 19 and 21, Vitalik at 20, Palmer Luckey at 21. Every time I sided with the veteran, I remembered the kids who rewrote the rules. Every time I leaned toward the kids, I thought about how many storms the veteran already sailed through.
By midnight, we’d switched sides three times.
Where I Landed
It’s not about age. It’s about whether someone sees the problem so clearly they can’t let it go.
That’s the trait I look for in a co-founder, a teammate, or myself. Because whether you’re twenty-two or sixty, if you wake up every day with that problem rattling in your head—you already hold a real founder’s advantage.
FAQ
Q: Do you prefer working with older or younger founders?
A: Neither. I prefer working with people who can’t stop thinking about the problem they’re solving.
Q: Doesn’t experience still matter?
A: Absolutely. Experience helps you avoid repeat mistakes. Obsession is what carries you to a solution.
Q: How do you spot a great problem solver?
A: They’re already testing—tiny experiments, quick feedback loops—even when resources are thin and odds are long.
Q: Can someone become more of a problem solver over time?
A: Yes. It usually starts with a spark, then grows through curiosity, adaptability, and real feedback.
Q: What’s the connection to your work at Reflekta?
A: Reflekta was born from an obsession with preserving human connection in a way nobody had done before—the same trait I value in any founder. Reflekta: The Feel-Good Soul Tech That Connects Passed with Present.