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A million dollars isn’t cool. You know what’s cool? A billion dollars.
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I suffer from the delusion that every product of my imagination is not only possible, but always on the cusp of becoming real.
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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.
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Spotify is returning a huge amount of money. We'll overtake iTunes in terms of what we bring to the record industry in under two years.
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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.'
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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
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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.
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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.
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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.
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I had a desire to prove to myself that I was actually in control - that I wasnt a puppet.
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In truth the social media elements of the Obama campaign, while extremely innovative, did not produce a lot of results.
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There's definitely some sort of dissent brewing between record labels, publishing companies and artists about the compensation they get from streaming services Spotify is returning a HUGE amount of money to the record labels. If we continue growing at our current rate in terms of subscriptions and downloads, we'll overtake iTunes in terms of contributions to the recorded music business in under two years.
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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.
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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.
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The leader of a company needs to have a decision tree in his head - if this happens, we go this way, but if it winds up like that, then we go this other way.
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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.
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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.
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If I were worried about my reputation, I wouldn't do anything with start-ups
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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.
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Little startups are ridiculously overfunded.
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One of the difficulties in living the lifestyle I lead is that it is hard to get my friends in one place.
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Running a start-up is like eating glass. You just start to like the taste of your own blood.
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You want people using your product because it's a part of your life, then they can't stop using it.
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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.