Well, if he leaves now, it's not as if he's going off to a terrible fate. He's been pretty well-paid. If he gets an IPO out of it someday, he'll get even more money, but if he doesn't, he gets to step off the burning ship.
Or, to put it another way, he doesn't have to go through firing all of those people that he hired when he was pumping the company up to ginormous size. I think perhaps the fun part of running WeWork was behind him, regardless of how it turns out.
Exactly. If they have a successful IPO and become a profitable company - he gets very rich. If they don't - he still stays rich and gets to gloat about it.
Softbank probably made it clear to him that if there is any hope to salvage the IPO and have a chance at a lucrative exit, this is the only path forward.
That or they found his cereal box and threatened to call the cops.