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

ℹ️ EPISODE INFO

Released

November 2, 2026

Duration

1h 5m

Channel

How I Built This

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

When COVID hit and Airbnb lost 80% of its business, Brian was forced to rethink everything he knew about leadership. In this conversation with Guy Raz, he shares why conventional management advice can be dangerous for startups, what he learned from Steve Jobs and Barack Obama, and why becoming a billionaire left him feeling lonelier than ever. Brian also discusses Airbnb.org, the nonprofit providing free emergency housing to people in crisis, and his ambition to expand its impact. *Subscribe to How I Built This:* https://www.youtube.com/@HowIBuiltThis?sub_confirmation=1 *CHAPTERS:* 00:00:00 - Introduction 00:00:08 - Airbnb's $100 billion IPO and the loneliness that followed 00:02:49 - From art school to Airbnb CEO 00:06:58 - Why Brian calls himself a terrible CEO 00:10:00 - The leadership advice that nearly derailed Airbnb 00:20:13 - How Barack Obama helped Brian confront loneliness 00:30:07 - The COVID crisis that changed everything 00:36:31 - What Brian learned from Steve Jobs 00:38:23 - Why Brian embraced hands-on leadership 00:56:22 - How Airbnb.org is helping people in crisis 01:00:42 - What's next for Brian and Airbnb #HowIBuiltThis #brianchesky #airbnb #GuyRaz #foundermode #startupadvice #businesspodcast *ABOUT HOW I BUILT THIS* On How I Built This, Guy Raz interviews the world's best-known entrepreneurs to learn how they built their iconic brands. Subscribe to the channel for more conversations with the founders behind the world's most successful companies. *LISTEN TO HOW I BUILT THIS* Apple Podcasts: https://podcasts.apple.com/us/podcast/how-i-built-this-with-guy-raz/id1150510297 Spotify: https://open.spotify.com/show/6E709HRH7XaiZrMfgtNCun *FOLLOW HOW I BUILT THIS* Instagram: https://www.instagram.com/howibuiltthis/ Facebook: https://www.facebook.com/howibuiltthis X: https://x.com/howibuiltthis *FOLLOW GUY RAZ* Instagram: https://www.instagram.com/guy.raz/ Website: https://guyraz.com/ *CREDITS* How I Built This is produced by Podcast Pointman and part of the Vox Media Podcast Network.

🎤 SPEAKERS

• Brian Chesky

  guest

  Co-founder and CEO of Airbnb.

• Guy Raz

  host

  Journalist and host of NPR’s How I Built This.

🧾 EPISODE SUMMARY

In this episode of How I Built This, featuring Brian Chesky and Guy Raz, Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO” explores Brian Chesky on loneliness, crisis leadership, and Airbnb’s founder-mode reset Brian Chesky describes the day after Airbnb’s Zoom IPO as emotionally empty, prompting a personal reckoning about ambition, validation, and what he wanted beyond success.