A million dollars isn’t cool. You know what’s cool? A billion dollars.

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.

I focus on things that are the highest value and do them perfectly.

Your biggest challenge as an entrepreneur is not concealing your idea from others or keeping your idea a secret, it is actually convincing people that you're not crazy and that you can pull this off.

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.

Little startups are ridiculously overfunded.