Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”
How I Built This with Guy Raz
- Published
- November 2, 2026
- Duration
- 1h 15m
- Summary source
- description
- Last updated
- Nov 2, 2026
Discusses Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a S…
Summary
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…
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Show notes
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