I'm making this analogy extreme for the sake of clarity not because I think it's legitimately comparable:
Charles Manson's friends and followers were pretty fond of him too.
Leadership of a company tends to attract rather extreme personalities in all kinds of directions. One of the tendencies that is extremely common is sociopathy. Sociopathy is usually found is charismatic, likable people, but those people don't actually care about your welfare.
I don't know if Chesky is a sociopath or not, I can't say one way or the other, but the way he spoke to EJ smacked of the single-minded self-absorption of one.
But that doesn't mean a sociopath can't be charming as hell at a party. That's how they succeed.