This is too cynical for even a turbo cynic like me.
Basically, you’re saying he mislead investors and got a bunch of money, so those investors see themselves being ripped off as a valuable skill, so they invest in him again. Wut?
I say again — why would investors trust him if his only track record is losing investor money?
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.
> I say again — why would investors trust him if his only track record is losing investor money?
Because they look at a serial fraudster and see themselves in him.
If you know he is good at duping investors then you know he is good at gaining investors, and if you think you will be able to well time your exit you will make a shit ton of money off the other investor's investment. Many investors are just straight up gamblers and risk is just part of the game.
Its like people who invest into a ponzi scheme knowing full well it is a ponzi scheme, just thinking they are smart enough to leave before it all comes crashing down. And once you get enough critical mass, other people will invest based entirely on the fact that there is a lot of other investors and a rising price.