
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.

The rise of taste, human authenticity and judgment in an AI world | Adam Mosseri (Head of IG)

Chatbots are not the final interface: OpenAI’s Head of Design on what’s next | Ian Silber

Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)

Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Riverside)

Becoming more strategic, navigating difficult colleagues, founder mode, more | Anneka Gupta

Finding hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)