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In this special compilation episode, we delve into failure—an overlooked source of wisdom. From freezing onstage in front of thousands of people, to coworkers staging an intervention, to huge product investments that went to zero, we’ve pulled our favorite stories of failure from 100+ podcast episodes. I hope these stories serve as a gentle nudge to view failure not as a setback but as a crucial detour toward growth.

Listen now on Apple, Spotify, Overcast, and YouTube.

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

In this episode, you’ll hear from:

(00:00) Lenny: Why I’m focusing on failure

(03:25) Katie Dill: The single meeting that changed how Katie leads forever

(08:03) Paul Adams: Freezing onstage in front of thousands of people

(18:38) Tom Conrad: Lessons from Pets.com and Quibi—two of the most famous product disasters of all time

(33:19) Sri Batchu: When you fail, make sure you fail conclusively

(39:00) Jiaona Zhang (JZ): One of the biggest product misses at Airbnb

(44:32) Gina Gotthilf: Everyone has an “A side” and a “B side,” and we should all share our B sides more

(57:57) Maggie Crowley: Her favorite interview question about failure, and lessons from a personal failure

(1:00:33) Thanks for listening

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.