What comes after the revolution is inevitably bureaucracy. Whoever wins the revolution builds a bureaucracy

I had a desire to prove to myself that I was actually in control - that I wasnt a puppet.

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

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.'

I've been doing a hybrid of investing and entrepreneurship, which I think initially I wasn't set out to do. But I realized it fit my personality.

I can sort of do what I want. Maybe I have to work harder to prove myself in some new relationship because they've heard some wacky stories about me. But at least I can get the meeting.