Venturing in Public — 4/30/25
Everyone in venture says they take risk.
Most of the time, they just pay high prices or go off strategy. And sometimes that’s the right move since venture ultimately is a business of exceptions.
We’ve internalized this idea that you have to be in one of the three breakout companies per year—at any price—because of the “power law.” But that’s not real risk taking necessarily – that’s following the herd.
Real risk looks different:
• Writing the first check when no one else will
• Backing someone weird, not pedigreed
• Going off-thesis because your gut won’t let it go
I missed the first fintech wave—Plaid, Mercury—because I couldn’t picture a new fintech ecosystem forming. I underestimated how fast trust, compliance, and distribution could shift and the idea that a better UX could change adoption of a financial service.
That wasn’t a market miss—it was a failure of imagination.
Real risk in venture isn’t just paying up.
It’s being early, being lonely, and being willing to look wrong… how else do you characterize taking risk?
