Running a start-up is like eating glass. You just start to like the taste of your own blood.
You have got to be willing to be poor as an entrepreneur.
I definitely wanted to earn my freedom. But the primary motivation wasn't making money, but making an impact.
It seems like the right thing to do is tackle problems other people aren't working on.
A million dollars isn’t cool. You know what’s cool? A billion dollars.
The transition strategies are more important than understanding what the outcome state will be.
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
Facebook isn't helping you make new connections, Facebook doesn't develop new relationships, Facebook is just trying to be the most accurate model of your social graph. There's a part of me that feels somewhat bored by all of this.
I focus on things that are the highest value and do them perfectly.
I suffer from the delusion that every product of my imagination is not only possible, but always on the cusp of becoming real.
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.
You just keep pushing yourself harder and harder to achieve more and more - I don't think it's ever quite as glamorous as it appears on the outside.
Little startups are ridiculously overfunded.
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 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.
You want people using your product because it's a part of your life, then they can't stop using it.
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.
Facebook is such a basic utility. It's something that is such a part of peoples' lives, I think it's hard to imagine it going away.
I think the perception of wealth and power is that things just become easier and easier when in reality as you raise the stakes things become more stressful.
If I were worried about my reputation, I wouldn't do anything with start-ups
Look: There's good creepy and there's bad creepy. Today's creepy is tomorrow's necessity.
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.
You can now be a master of your own destiny. I'm not sure why you would sign up with a record label.
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.
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.
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