Insight certainty 4/5 debate potential 3/5

Lessin: VC's worst outcome is picking a winner without equity upside

Sam Lessin · DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings · Aug 11, 2023 · at 23:22

Sam Lessin, Co-Founder and Partner at Slow Ventures, argues on 20VC that backing a massive startup winner without sufficient fund ownership to generate fund-returning capital is worse than being wrong.

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“You know, I think the most depressing thing in the world is not being wrong. It's being right and not making money. You know, being right to the tune of, like, having these epic outcomes and being like, ah, fuck, that was a one-ex returner of the fund, right? Fuck, right? Like, that's the thing that, like, is kind of the worst case scenario, right? Because those are rare and far, far to find.”

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