What Did Barack Obama Tell Brian Chesky About Loneliness?

Brian Chesky says the chief executive job can be lonely in a way founding was not. With co-founders he had friends, nobody was really in charge, and it felt like a college crew. As chief executive he was less able to socialize with employees, the walls felt like they were caving in, and a lot of the emptiness after the IPO was loneliness. He was not happier running a $100 billion company than a $20 billion company. The rush wore off, and he decided he needed more friends.

He wrote Barack Obama a long letter asking for help. Obama told him the problem was simple: he was really lonely. Obama said he had at least 15 friends he could call without catching them up, many from high school, including a fisherman named Bobby he had known since then. That was how Obama said he stayed grounded. Chesky had a friend named Bob he had not talked to in about a decade. Those relationships were dormant because he had put his whole life on hold, stayed closed off at work, and would not admit he was struggling.

During the pandemic he called high school and college friends and started Zoom calls with them. The calls only replayed old stories, so they started taking trips together. He says that changed his life.