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

Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time. But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company become increasingly chaotic. Looking back, he says Airbnb succeeded in spite of his leadership, not because of it. Then COVID hit, and Airbnb lost 80% of its business in a matter of weeks. Facing the possibility of losing everything he'd built, Brian completely reinvented the way he ran the company—and soon after, much of his life outside work, too. In this episode, Brian explains why some of the most common leadership advice can be disastrous for startups, what he learned from Steve Jobs and Barack Obama, and why the day after Airbnb’s IPO was one of the loneliest of his life. Plus, how Airbnb.org is providing free housing to people in crisis—and why Brian wants to expand that effort to one million nights a year. What You'll Learn How an art school graduate with no business experience became the CEO of Airbnb Why Brian describes himself as “naturally a great founder but naturally a terrible CEO” How following conventional leadership advice created chaos inside Airbnb Why Brian believes "hire great people and get out of their way" can be a death sentence for startups How losing 80% of Airbnb's business during COVID forced Brian to reinvent his leadership style What studying Steve Jobs taught Brian about getting into the details How Barack Obama helped Brian understand and confront his loneliness Why reaching a $100 billion valuation left Brian feeling empty How Airbnb.org grew from helping people displaced by Hurricane Sandy into a global nonprofit—and an ambitious plan to provide one million nights of free housing annually How Brian thinks about Airbnb's future—and why he has no plans to stop building Timestamps: (00:03:23) - Airbnb goes public at a $100 billion valuation, but Brian wakes up feeling empty (00:06:05) - From art school to Silicon Valley: How Brian became an unlikely tech founder (00:10:37) - "I was a great founder and a terrible CEO": Brian's early leadership mistakes (00:13:21) - Why hiring experienced executives and getting out of their way didn't work (00:17:59) - The self-doubt and chaos of running a fast-growing company (00:23:41) - How Barack Obama helped Brian confront his loneliness and reconnect with old friends (00:33:55) - Why Airbnb's early success led to overconfidence and costly distractions (00:38:10) - COVID wipes out 80% of Airbnb's business—and forces Brian to change (00:40:05) - What Brian learned from Steve Jobs about hands-on leadership (00:47:44) - Why Airbnb's leadership overhaul drove away much of its executive team (00:50:54) - The 70 revisions of a single press release that helped Brian redefine excellence (00:52:12) - How Brian gets honest feedback from employees who might be afraid to disagree (00:57:38) - Why Airbnb is reconsidering some of its long-held beliefs about its business (01:00:48) - Airbnb's plans to provide free housing for people in crisis (01:05:09) - Why Brian hopes to keep building for the rest of his life Production Credits Our production is handled by Podcast Pointman. Follow How I Built This: YouTube → @HowIBuiltThis Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com Learn more about your ad choices. Visit podcastchoices.com/adchoices