Just watched the Big Short movie again and one of the things that struck me on second viewing was how risky a short position really is - even if you have complete confidence in your decision. A short position is not only a bet against the thing you’re shorting but also involves careful timing which nobody can predict. Investors are required to pay premiums on their positions so while you’re waiting for the market to tank, you’re basically paying into it for an unknown period of time.
Shorting Uber seems like a sound idea. Their business practices are suspect and they are wildly overvalued. But I wouldn’t be so confident that they are headed into the basement anytime soon.