Why Did Brian Chesky Feel Lonely After Airbnb Went Public?

Brian Chesky says he felt lonely the day after Airbnb went public because the rush ended and his life felt no different than the day before. Guy Raz sets that day as December 10, 2020, when Airbnb finished worth over $100 billion. Chesky went to bed as chief executive of a public company, never having imagined he would lead even a 10-person company. He woke to an empty house, still sheltering in place, put on sweatpants, and sat through a random Zoom meeting. Regular life was back, and the gap set off an inner crisis.

The listing happened on Zoom during the pandemic, with no bell and no gathering of family, friends, or early people who helped build Airbnb, only boxes on a screen. From childhood he had wanted to be special, often without realizing it, and he thinks much of the ambition came from wanting validation. The world's praise felt like adulation rather than love, a drug that wears off very quickly and demands more each time. Standing on the mountaintop, after a life spent climbing, he saw that success was not going to change how he felt inside, and he wondered what other mountain was left.

The questions that opened up were what he wanted from life and why he was doing the work. Airbnb did not begin as an effort to become successful. He jokes that a plan to make money would not have left him inflating air mattresses.