I guess people often think the things they imagine making themselves happy would make someone else who has that happy, and I just don't think that's the case that often. I don't think money buys happiness after a point, a certain amount gets rid of a lot of discomfort and stress and brings relief and security, a bit more can buy some happiness, after that it's just number go up.
I say this as somebody who has never had any admiration for this guy (not because of a specific grievance, but because I don't follow tech leadership and am generally pessimistic about them).
That being said his early life is crazy enough that a movie could save him. Lazy thinking is fickle, after all.
He's also spent his life building a large, very influential company.
Could it be that those are the things he values?