My First Million ft. Aaron Levie

Picking enterprise over consumer, why AI makes everyone busier, and the mental trick that shortens anxiety spirals. Three decisions that look obvious in hindsight and almost never are.

With Aaron Levie

"Every single person that is like the most AI-pilled right now is just drowning in work because we're kicking off way more work for ourselves." — Aaron Levie

Aaron Levie, on the episode

Aaron Levie is the co-founder and CEO of Box, the enterprise content platform he started with three co-founders in college before dropping out in 2005 and 2006. The pop framing of Box is a file storage company that got lucky picking enterprise over consumer. The actual operating system is sharper: Levie has spent 20 years making a series of bets that looked wrong at the time and right in retrospect, and he has a specific set of frameworks he uses to explain why. This conversation covers the enterprise pivot, the psychology of turning down half a billion dollars in your mid-twenties, why AI is making every founder work more not less, how a therapist's single word changed how he handles crisis, and the six books he thinks predict 100 percent of what happens in technology markets.