Aaron Levie: The Restless Founder Plotting the Future of Cloud Storage and AI

When the team behind Box first went looking for funding back in 2005, they tried just about every trick in the book. They sent Bill Gates a fax. They dropped a prospectus off at Paul Allen’s house in Seattle. And they took a shot at convincing Mark Cuban to join two ambitious college kids with a hunch the way businesses stored and collaborated around information was about to change. Two decades later Box is a cornerstone of the cloud era with $1 Billion in revenue, but co-founder and CEO Aaron Levie is as restless as ever. In this episode, Mike Maples, Jr. of Floodgate speaks with Levie about how he started Box when he was still in college at USC, why it’s fatal for startups to hire sales reps too slowly, and how he’s personally leading the way as the company looks to reinvent itself in the era of AI. Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike. Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

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Aaron Levie: The Restless Founder Plotting the Future of Cloud Storage and AI is an episode from Starting Greatness by Mike Maples.

This episode is 00:40:49 long.

This episode was published on Mar 31, 2025.

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