Episode #18 of Yesterday:Aaron Levie is the co-founder and CEO of Box (NYSE: BOX), a cloud storage company used by over 100,000 businesses worldwide, including 67% of the Fortune 500. He co-founded Box in 2005 while a student at USC, initially funding it with online poker winnings before securing an investment from Mark Cuban off a cold email. Under Aaron’s leadership, Box grew from a dorm-room startup to a publicly traded company with more than $1 billion in annual revenue and over 2,000 employees. In this episode, Aaron shares the unfiltered journey behind that growth: The early pivot from a consumer product to an enterprise-first model, to navigating the “innovator’s dilemma” He also discusses how the iPhone and the broader mobile revolution reshaped Box’s product strategy and accelerated enterprise adoption. TIMESTAMPS: 00:00 Intro 01:34 Box Origin Story 04:24 Funding the Company with Online Poker 05:46 The Cold Email That Landed Mark Cuban 07:06 Dropping Out of College for the Dream 09:52 Advice From Mark Cuban 11:12 Enterprise vs. Consumer 12:50 Using the “Innovator’s Dilemma” 15:59 The iPhone Launch 17:46 The ChatGPT Moment 21:02 AI Pivot 26:05 SORA Video Generation 29:45 Why Most Companies Are Failing 33:12 Agents Automating Everything 35:50 Jack Dorsey’s Favorite Entrepreneur 38:13 Advice for Young Founders Presented by Rho: Rho is the all-in-one banking platform for startups, used by Perplexity, Product Hunt, and thousands of other companies. You get everything you need to manage your startup’s cash & a team that’s obsessed with helping founders beat industry giants. Learn more at rho.co/yesterday Sponsored by The Cannon Project (TCP): TCP recruits founding GTM and engineering teams for startups like Ramp, Cursor, and Decagon while investing through their flagship venture fund, TCP 1. Apply for roles and learn more at thecannonproject.com

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