Why Does Brian Chesky Say He Was a Great Founder but a Terrible CEO?

Brian Chesky says he was naturally a great founder and naturally a terrible chief executive. He calls that a classic story. He does not know a founder for whom becoming a chief executive felt completely intuitive, though he is sure exceptions exist.

Founding felt intuitive. He leaves open whether people are born good founders, then treats a lifetime of practice as the real answer. A child makes things, builds things, and practices being a founder, so founding a company is probably not the first attempt to make something. He puts his own practice at 20 years, starting as a child: designing, taking Christmas toys apart, and selling things to friends. By the time Airbnb was founded, he and co-founder Joe Gebbia had decades of that practice. The chief executive job was the part that was not intuitive.