Uploaded August 2025 | Updated September 2026, 2 weeks ago

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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 Drew
X: https://x.com/drewhouston
LinkedIn: linkedin.com/in/drewhouston

Connect with Joubin
X: https://x.com/Joubinmir
LinkedIn: linkedin.com/in/joubin-mirzadegan-66186854
Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins: kleinerperkins.com