Yesterday Podcast Aaron Levie | He Cold Emailed Mark Cuban To Invest in His Startup (Now They’re Worth $5B)
Oct 17, 2025
Aaron Levie, co-founder and CEO of Box, shares his incredible journey of building a $5B cloud storage company from a dorm room. He reveals how he cold-emailed Mark Cuban for investment, leading to a pivotal freemium strategy. Levie discusses Box's shift from consumer to enterprise, leveraging the iPhone's launch to drive adoption. He also dives into the transformative impact of AI on business workflows, and offers advice for young founders about navigating innovation without existing templates.
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Dorm-Room Origin And Poker-Funded Scaling
- Aaron Levie started Box in 2005 to access and share files from anywhere using the web browser.
- His co-founder Dylan funded early scaling with online poker winnings before they raised angel capital.
Cold Email To Mark Cuban Led To Early Check
- Aaron cold-emailed Mark Cuban and got a fast, positive reply leading to an investment of a few hundred thousand dollars.
- That early check let them scale, introduce freemium, and decide to drop out of college to focus on the company.
Don’t Hedge — Commit To One Path
- Avoid hedging on architecture or strategy; pick one path and commit fully as a small startup.
- Focused commitment yields upside that a split strategy cannot capture.
