AI Summary
5 min readThis compilation episode from Lenny's Podcast draws stories of failure from past guests to highlight how setbacks in leadership, product work, and careers often yield the deepest lessons, contrasting with typical focuses on success.
Leadership Trust and Early Missteps
A design leader at Airbnb arrived eager to fix low team engagement and collaboration issues but moved too aggressively without building trust. After a group confronted her with scripted feedback a month in, she listened without defending, shifted to understanding individual motivations, and brought the team along on changes. Engagement scores soon topped the company, teaching that change imposed fails, while co-created efforts with trust succeed.
Paul Adams at Intercom recounted freezing mid-keynote at Cannes in front of thousands, walking off stage mic'd up while cursing, then recovering by returning disarmed, which turned the talk around. He also covered Google social flops like Buzz and Google+, driven by competitive fear rather than user needs, despite adjacent successes like Maps and Android. His mid-project exit to Facebook amid scrutiny reinforced avoiding fear-led projects.
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What you'll learn
- 1 `* (00:02) **Episode Intro: Value of Learning from Failure**`
- 2 `* (03:42) **Airbnb Design Leader: Earning Team Trust After Harsh Feedback**`
- 3 `* (08:04) **Paul Adams: Stage Freeze and Google Social Failures**`
- 4 `* (18:38) **Tom Conrad: Pets.com and Quibi Disasters**`
- 5 `* (33:38) **Sri Batchu: Failing Conclusively in Growth Experiments**`
- 6 `* (39:13) **JZ: New PM Mistakes and Airbnb Plus Miss**`
- 7 `* (44:53) **Gina Gotthilf: A-Side vs. B-Side Career Realities**`
+ Full timestamped outline available in the app
Show Notes
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.
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Find the full transcript at: https://www.lennysnewsletter.com/p/failure
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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
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Lenny may be an investor in the companies discussed.
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