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.
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.'
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.
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.
There came a time when these two incompatible notions of who I was, well, something had to give. Either that 'something' is where you acquiesce to the world around you and you conform, or you sort of defiantly break whatever remaining bonds connect you to that world and create for yourself a different set of values.
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.
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.
It would be incredibly presumptuous and self-serving of me to believe that Facebook was the end of history. The only way it could possibly be the end of history is if it becomes some sort of artificial super intelligence that takes over the world.
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.
If there's some triumphant end of the story, I guess in a roundabout way I've gotten what I wanted, which is the ability to do interesting things and the wealth to be free.
There's definitely some sort of dissent brewing between labels, publishing companies and artists. A lot of it has to do with older licensing schemes.
You start to accumulate your library of music. You want that music everywhere - that's the point where we monetize. If you want portability, mobility, and access, then you buy 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.
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 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.
The market is ridiculously overcrowded with early stage investors. This results in a talent drain, where the best talent gets diffused and work for their own startups.