Chesky: Learning via trial and error as CEO wastes years unwinding empires
Brian Chesky · How Brian Chesky Is Redesigning Airbnb for the AI Era · Invest Like The Best · May 5, 2026 · at 7:43
Airbnb CEO Brian Chesky explains the hidden organizational cost of trial-and-error management when scaling leadership.
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“You do not want to learn on the job how to be a CEO. In other words, trial and error is bad for a CEO. You know why trial and error is really bad? Because you hire somebody, they build an empire, they leave, and now you get to unwind their empire, and it takes like four years. So you've wasted years.”
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