Brian Chesky Traces His Early CEO Mistakes to Deferring to Experienced Staff
Brian Chesky traces his early mistakes as chief executive of Airbnb to deferring to older, more experienced employees when they contradicted his intuition. On the How I Built This podcast, he called himself naturally a great founder and a terrible CEO. Airbnb, which he has led since 2007, now has over 5.5 million hosts and generated $12.24 billion in annual revenue in 2025.
The standard counsel to hire great people, trust them and step aside comes, in Brian Chesky's account, from the chair of a mature company; applied to a young one, he calls it a death sentence. His own deference followed the same pattern: experience spoke from across the table, his intuition gave way, and the outcome was usually a mistake. His alternative is smart, hungry hires kept close.
Source: Entrepreneur · November 4, 2026