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Published · transcript-backed

Lenny Rachitsky: uncertainty

12 Apr 2026 Lenny's Podcast Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

“We interviewed, this is me and Terrence Rohan. I don't know if you know him, VC.”

— Lenny Rachitsky

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Everything needed to verify it.

Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
uncertainty
Recorded
12 Apr 2026
Publisher
Lenny's Podcast

Transcript context

…It's like a startup. I mean, that is actually the startup. I use this prism as an investor, which is when I make a seed investment or series A investment, let's say, I want half of my friends who are VCs to laugh at me. Literally laugh because I know most of the people I compete with pretty well. And so I'm running this algorithm through my brain. Are these people going to laugh? If so, this is potentially a great investment because it's an ugly baby. And ugly babies are the ones where there's real alpha. That's so interesting you say that. I did some research recently on what are signs. We interviewed, this is me and Terrence Rohan. I don't know if you know him, VC. We interviewed early employee, people that have joined early generational companies many times. They joined OpenAI early before anyone knew about it. Palantir, really early, Stripe. And so we asked them, "What did you look for?" And there's three patterns. And one of them was exactly that. The idea, people laughed at them. They thought it was crazy. This is never going to work. Palantir, for example, OpenAI, for example. Yeah. My parents used to laugh at almost all my jobs in tech. It used to be very funny. They thought I was going to be homeless because most of them did not make sense to them.…

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