I'll be very interested to learn how often this happens. Certainly Kalanick and Neumann managed to walk away billionaires from companies that have never turned a profit. But I'm hoping that is a rare outcome.
Just because Uber hasn't turned a profit doesn't mean they aren't worth $xxB.
If you actually believe Kalanick cashed out his shares at an overvalued price, go short Uber and make tons of money. That said, you're probably wrong.
It depends on what you mean by "worth". Market price is market price, after all. But it's perfectly plausible that Uber will never turn a profit. It's indisputable that Uber was severely overvalued for a long time. And when thinking from a systemic perspective about whether Kalanick should be a billionaire, we have to reckon with the externalities.