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.

Little startups are ridiculously overfunded.

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.

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

You want people using your product because it's a part of your life, then they can't stop using it.

I suffer from the delusion that every product of my imagination is not only possible, but always on the cusp of becoming real.

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