Airbnb CEO Brian Chesky Thinks He Can Make Cities More Affordable

About this episode

Next year, Airbnb will mark its 20th anniversary. Through its evolution—from a few air mattresses placed on an apartment floor to one of America’s best-known American technology companies—it has been led by Brian Chesky. And at a time when Silicon Valley doesn’t champion introspection, Chesky, 45, is an outlier: someone who has become a prominent voice on company leadership and a frequent investigator of his own character. “The primary weakness of me as a founder running a company was people had to pay for my immaturity in my thirties,” he told me during a recent interview at Airbnb’s headquarters in San Francisco for our new interview series, The CEO Moment . “But I said it was a good…