I asked Ray Dalio how he uses AI in his investing process."It thinks it's very smart. It's not as smart as it thinks it is, but it can be smart.""I know a lot that it doesn't know. But at the same time... it can teach me." There's a back-and-forth that ensues. It's not one way street."You have to know your decision-making systems; you can't let it make decisions." In other words, feed the AI your framework and criteria upfront, and then debate it *within the framework you provide*.Video from a r ...

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What's the optimal amount of success to have early on in a fund or in a career, if you’re optimizing for long-term franchise or career value? I think there is such a thing as too much success, too early.When evaluating a founder who’s starting their second company, I’m more excited if their first company was a strong performer but not necessarily a spectacular unicorn. They know what success looks like, yes, but they also still possess an extreme learning and hustle drive.In venture funds, if yo ...

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Which founders honor pro rata rights with little complaint? Age + life experience tends to be predictive.Younger founders who only know bull markets and/or have only experienced good times with their company can be more aggressive about playing hard ball on pro rata.Older founders who've seen downturns and/or experienced hard times in their founder journey tend to be more conciliatory even in a hot round...because they know that when times are tough, you need your insiders. ...

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