I misinterpreted you; I was arguing that he's already succeeded completely, so it doesn't matter if anyone gives him more money.
But, IMO the reason they're still giving him more money is that they're stupid and greedy. They know WeWork was a disaster, but it was a huge disaster. That shows them he's good at running a con, and they want to get in on the next one.
Class solidarity doesn't hurt either. Being a billionaire makes him an actual person in the eyes of other rich people.
EDIT: Also, it's funny you used a16z as an example:
> Not saying you are wrong, but if I am a "capital allocator" at a16z, he would be no-go.
because Andreesen Horowitz are the ones investing in his new WeWork 2.0 startup Flow.