Aaron Levie, co-founder and CEO of Box, has guided the cloud content management platform from a dorm room project into a publicly traded company with over $1B in annual revenue. In his second appearance on B2BaCEO, Aaron reflects on his founder journey, sharing how Box capitalized on cloud computing and their recent push to integrate generative AI. But our conversation goes far beyond Box. Aaron’s role has given him a unique vantage point on what the latest advances in AI mean for founders. We explore the AI applications that excite him most, where he sees opportunities for startups over incumbents, and the potential areas in AI that founders might be overlooking. (0:00) Intro (2:26) The Box journey (4:23) Transitioning to enterprise (8:26) Building a GTM flywheel (11:45) Lessons from the enterprise journey (15:16) Where AI is heading (18:14) Facing the innovator's dilemma (20:54) AI agents (26:15) Why AI is positive sum for the economy (30:24) The AI doomer debate (34:22) The evolving model ecosystem (40:30) Parting advice for founders