How Dropbox Beat Big Tech in the Cloud Wars

25 Aug 2025 • 92 min • EN
92 min
00:00
01:32:34
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How do you win when your competitors are the biggest companies in the world? This week on Grit, Dropbox co-founder and CEO Drew Houston retraces the path from a bus-stop prototype to competing head-on with Google, Apple, and Microsoft. He explains why grit is “learning to run toward discomfort,” and the moments he realized founders keep going “for the love of the game.” Guest: Drew Houston, Co-Founder & CEO of Dropbox Chapters: 00:00 Trailer 00:52 Introduction 01:35 Towards full autonomy 16:20 Coming back to school 21:45 Golden ticket to California 25:23 No one’s born a CEO 28:15 Y Combinator and a co-founder 37:53 The craft of being a great CEO 53:41 Metabolizing the stress 1:10:14 Tactical advices and frameworks 1:27:48 Who Dropbox is hiring 1:29:35 What “grit” means to Drew 1:32:10 Outro Links: Connect with DrewXLinkedIn Connect with JoubinXLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner Perkins

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