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I think the Kalanick you describe here is a ruthless businessman that veers across the line into asshole and that's...not great. But again, it's not the same t

• wpietri 7y ago
  Time will tell. Uber and WeWork are both bets on the ability to get monopoly-level pricing power on a major chunk of economic activity, just like Google and Facebook did. Neither one has a valuation that makes sense without that pricing power, and both of have been trying to buy it via liberal application of investor money. But in both cases, they've never turned a profit and there's no obvious moat. 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.