Why Does Hiring Great People and Getting Out of Their Way Fail?

Brian Chesky says hiring great people, trusting them, and getting out of their way is what a mature company does, and it is a death sentence for a young company. A young company should not hire big grownups who do not understand its stage. It should hire people just a little ahead who are smart and hungry, and the founder has to stay close to them and close to the work.

The hard part of the job is a culture where people still do the desired work when the leader is out of the room. Becoming profitable and managing expenses are easy next to that.

He usually deferred when an executive's experience collided with his intuition, and he calls that a mistake. Many of those executives were old enough to be his parents, came from big companies they had managed rather than built, and had trouble applying that scale to a company that still had to be built. He was intimidated, a bit of a people pleaser, and shy about telling older people what to do.