# Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”

- Show: [How I Built This](https://hardwarepodcasts.com/podcast/how-i-built-this)
- Published: 2026-11-02
- Length: 1h 15m
- Page: https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo

## Summary

Airbnb CEO Brian Chesky explains how he transitioned from a 'terrible CEO' who deferred to experienced executives to a hands-on leader during the COVID crisis, adopting Steve Jobs' 'founder mode' to save the company. He details the importance of staying in the details, skip-level communication, and empowering rather than giving autonomy to teams, while also discussing the launch of Airbnb.org’s goal to provide one million free nights of housing annually.

## Chapters

- [0:01](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=1) Introduction: Brian Chesky and the Crisis of Leadership
- [3:03](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=183) The Loneliness of the IPO and Post-Success Crisis
- [6:05](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=365) From RISD Artist to Unlikely Tech Founder
- [10:18](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=618) Mistakes of Early Leadership and Deferring to Executives
- [23:10](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=1390) COVID Crisis and the Pivot to 'Founder Mode'
- [35:13](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=2113) Studying Steve Jobs and Reclaiming Control
- [45:53](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=2753) Empowerment vs. Autonomy and Managing Up
- [49:56](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-11-02-airbnb-ceo-brian-chesky-i-was-a-great-founder-and-a-terrible-ceo#t=2996) Airbnb.org and the One Million Nights Initiative

## Topics

- [Leadership, teams & culture](https://hardwarepodcasts.com/topic/leadership-and-culture)
- [Direct-to-consumer & e-commerce](https://hardwarepodcasts.com/topic/direct-to-consumer)
- [Starting a product company](https://hardwarepodcasts.com/topic/starting-a-company)

## Most relevant to

large enterprises

## Mentioned

- Airbnb (company)
- Steve Jobs (other)
- Airbnb.org (product)
- Apple (company)
- Jony Ive (other)
- Ron Johnson (other)
- Hiroki Asai (other)
- Netflix (company)
- Marriott (company)
- United Airlines (company)
- Chase (company)
- Tesla (company)
- Disney (company)
- Nike (company)
- McDonald's (company)
- Sloan Kettering (other)
- RISD (other)
- Y Combinator (other)
- Amex (company)
- Ken Chenault (other)
- Barack Obama (other)
- Joe Gebbia (other)
- Nathan Blecharczyk (other)
- Colin Angle (other)
- iRobot (company)
- Roomba (product)
- Antonio's Pizza (other)
- Thayer Street (other)
- Proctor and Gamble (company)
- Sam Walton (other)
- Walt Disney (other)
- Jeff Bezos (other)
- Larry Ellison (other)
- Peloton (company)
- Reed Hastings (other)
- Charles Eames (other)
- Leonard da Vinci (other)
- Vincent Van Gogh (other)
- Frank Lloyd Wright (other)
- Pablo Picasso (other)
- Rafael (other)
- Guy Raz (other)

## Related episodes from other shows

- [Reflecting on Founder Mode](https://hardwarepodcasts.com/podcast/oxide-and-friends/2024-09-20-reflecting-on-founder-mode) (Oxide and Friends)
- [Tool of the Week Segment | Episode 31](https://hardwarepodcasts.com/podcast/built-2-scale/2025-12-04-tool-of-the-week-segment-episode-31) (Built 2 Scale)
- [Moonshot Engineering Projects: Getting Innovative Initiatives Off the Ground](https://hardwarepodcasts.com/podcast/over-the-air/2021-05-25-moonshot-engineering-projects-getting-innovative-initiatives-off-the-ground) (Over the Air)
- [On-Demand Labor, Operations, and Finding a Co-Founder with Veryable CEO Mike Kinder](https://hardwarepodcasts.com/podcast/manufacturing-happy-hour/2021-09-21-on-demand-labor-operations-and-finding-a-co-founder-with-veryable-ceo-mike-kinde) (Manufacturing Happy Hour)
- [#219 - Managing People at Work with Seth Goldman of JUST Ice Tea](https://hardwarepodcasts.com/podcast/the-startup-cpg-podcast/2025-10-21-219-managing-people-at-work-with-seth-goldman-of-just-ice-tea) (The Startup CPG Podcast)

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