Why Does Brian Chesky Watch How People Treat His Assistant?

Brian Chesky asks his assistant how nice people are to her, because success makes everyone nicer to him and he becomes a bad read of character. Some people were very obsequious with him and would not treat her well.

He kept letting new people in on purpose. Stopping new friends means stopping growth and stopping learning. He would ease in rather than hand over something like a bank account. The risk of a few people violating his trust was better than the risk of living alone the rest of his life. A few people did break his trust. It was not irreparable, and taking the risk was 100 percent worth it. His default was to trust and let the consequences land wherever they landed.

Refusing to date so nobody can break your heart is the same trap as refusing to start a company because it might fail, refusing to hire someone because it might not work out, or refusing to exercise because you might get hurt. You are going to die anyway. You might as well live.