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

I lived on couches for something like six months. I had no home. I was totally broke. I would stay at a friend's house for two weeks, then move because I didn't want to become this permanent mooch.

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.

You actually don't want people thinking your product is cool, because then you're a fad.

At every point I am besieged by people who would like me to conform to some social norm of whatever sort of social group they expect me to be a part of. I never have any identification with these social groups.

If I were worried about my reputation, I wouldn't do anything with start-ups

It seems like the right thing to do is tackle problems other people aren't working on.