Well, losing all of your friends is a good start. He owns a "punk" label (think pop punk like Thursday and such) who are all backing out on him and then of course the Twitter thing. It's one thing for Presidential nominees to come down on him, and his little power trip isn't that different from Donal Trump's, but they're thousands of miles away, in his mind and probably in proximity. Binside, if he ever had much insides to begin with.
Or, take the easy way and give him HIV. I'm sure he throws a bunch of parties..
He went from college (im assuming some financial education) to interning at a hedge fund to working at a hedge fund to somehow getting rich enough to be an investor.
His life was guaranteed to be a bubble of finance industry 'bros'.