I've worked in startups a long time myself. Personally I've never seen this problem, feels like it's advice literally specifically for Chesky or maybe a founders at a couple dozen other unicorns. In my experience it's a way more common problem in the other direction. Founder can't let go of the details and is mucking about in everyone's work. Or have literally just become bored with the company and can't even be bothered to hire the professional executives that are supposedly such a problem. Perhaps a hot take, but IME most professional executives/managers/MBA types are actually pretty solid people to work with and do a good job.