Skip to content
Lenny's PodcastLenny's Podcast

Failure

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. — Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps: https://sendbird.com/lenny | Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ Find the full transcript at: https://www.lennysnewsletter.com/p/failure Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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.

Lenny RachitskyhostGuest (Airbnb leader sharing an intervention story)guestPaul AdamsguestTom KonradguestMaggie Crowleyguest
Dec 13, 20231h 1mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 3:25

    Lenny: Why I’m focusing on failure

  2. 3:25 – 8:03

    Katie Dill: The single meeting that changed how Katie leads forever

  3. 8:03 – 18:38

    Paul Adams: Freezing onstage in front of thousands of people

  4. 18:38 – 33:19

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

  5. 33:19 – 39:00

    Sri Batchu: When you fail, make sure you fail conclusively

  6. 39:00 – 44:32

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

  7. 44:32 – 57:57

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

  8. 57:57 – 1:00:33

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

  9. 1:00:33 – 1:01:11

    Thanks for listening

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome