It’s not cool. I think being a wealthy member of the establishment is the antithesis of cool. Being a countercultural revolutionary is cool. So to the extent that you’ve made a billion dollars, you’ve probably become uncool.

My interactions with Sorkin were agonisingly weird. He is by far the weirdest person I have ever met. I had dinner with him and a few hours before I got an e-mail from his assistant saying, 'Sean, this does not need to be a long conversation. Aaron is only going to use it to win your trust.'

Gray hats are the ones who think they're doing good, but they're not. You learn that when the FBI shows up on your doorstep.

Part of the challenge of being an entrepreneur, if you're going for a really huge opportunity, is trying to find problems that aren't quite on the radar yet and try to solve those

Running a start-up is like eating glass. You just start to like the taste of your own blood.

One of the difficulties in living the lifestyle I lead is that it is hard to get my friends in one place.

You can now be a master of your own destiny. I'm not sure why you would sign up with a record label.