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Investor admits he'd make the same costly mistake again

The Full Ratchet · Investor Stories 461: Feast and Famine in Crypto, When to...

“I think three years before that, we could have made another five to 10 x and made history.”

4:39 / 5:18

I think three years before that, we could have made another five to 10 x and made history. It would have been the best private acquisition in 2021 in the history of venture capital. But I support the entrepreneur. I just went with the flow. And I can't change it because I'm a people first investor. I tried my best, failed. It's okay. It's okay. And I don't know what I'll do better. I think I'll keep making the same mistake. My job, as you said, is not to be prescriptive giving put. People want to go, I should go.

About this clip

A venture capitalist reflects on missing out on what could have been the best private acquisition in VC history in 2021, explaining why his people-first investment philosophy means he'll likely repeat similar mistakes. He discusses the tension between maximizing returns and supporting entrepreneurs' decisions, even when it costs millions.

Why this clip

This clip captures a rare moment of vulnerability where an investor openly admits to a massive missed opportunity while defending the values-driven approach that caused it.

4:39 - 5:1838spersonal lesson
exit-timinginvestor-philosophypeople-first-investing

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