With Uber, at least there was a real business, with some real differentiation and not the tremendous Capex overhead of real estate to weigh down the business. Imagine if Uber had to employ all of the drivers full-time and also own the cars outright, that would be a dramatically different business.
But everyone is happy when things are moving up and to the right, but in this case, the losses outweighted revenue. It's one thing for a startup to be burning x% of revenue to grow market share, but to literally every year burn more capital than revenue at such a massive scale is completely bonkers.
The only logical conclusion is that Masayoshi Son was calculated in this. In that he had some belief that WeWork would work, but additionally if he was able to markup his shares through his own investments, he could then raise a second vision fund based on the supposed returns of the first one.
Obviously that plan is now shot with Uber trading below the value of his private investments, and with WeWork it is an even larger hole that he has dug for himself, because not only is it's value dramatically less than when he invested, but there is a real possibility that the company may not be able to get on to solid financial footing.
Softbank would literally be the only investor willing to put in more capital at this point, and they almost have to in order to save the business, but at that point, don't be surprised if the entire cap table is completely redone.