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The naivety framing is sharp. Training yourself to stay naive while avoiding clout-chasing are fundamentally different skills, and the tension between them probably explains why most people end up doing one or the other but not both. Side projects while everyone's asleep is relatable, though I wonder if it actualy does signal hedging to founders or if that's just projected anxiety. In my experience the people who keep building tend to understand product intuition better than pure pattern-matchers, which seems like it'd be an advantage when evaluating early stage stuff.

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