How Dropbox Beat Big Tech in the Cloud Wars
- Author
- Kleiner Perkins
- Published
- Mon 25 Aug 2025
- Episode Link
- https://share.transistor.fm/s/1a0cf8fc
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 Drew
Connect with Joubin
- X
- Email: [email protected]
