But again, it's not the same thing as Holmes (fraudster) or Neumann (purveyor of fantastical bullshit).
I agree that WeWork's vision is now more obviously likely to fail than Uber's. But WeWork's transition from hero to goat happened quite recently. Uber got a cash infusion from their IPO that gives them something like 18 months runway, but with their stock down 30% from IPO, they can't do that forever. We'll see what happens when they have to break even. Especially if they have to start paying their workers fairly. And if the margins in that business turn sufficiently positive, I expect people will be eager to compete.
And even if they do manage to pull it together, I'm still comfortable putting Uber in that category, as Kalanick wasn't just an asshole, but a willful criminal who got his money through the same performative asshole/genius shtick. He may ultimately get away with it. But I think he's decreased the likelihood people will fall for it again.
I also think you're giving Uber way too much credit. They are the dominant player because Kalanick was unusually terrible and because his investors gave a terrible person a lot of money. He didn't invent remote taxi dispatch (which was a telephone-era innovation) and he wasn't first in the anybody-with-a-car-can-be-a-taxi game (which was Lyft). He was just more willing to break laws and be a dick to competitors.
I believe that if Uber hadn't appeared on the scene, things would be about the same (by which I mean we'd have people ordering rides via smartphone) but in a healthier way (by which I mean not burning billions per year, less worker exploitation, fewer negative externalities, and healthier municipal regulation).
So I'll give plenty of credit to the smartphone pioneers, especially Palm and Apple. But not much to Kalanick.