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'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 is no simple answer to what I think.

You have got to be willing to be poor as an entrepreneur.

You actually don't want people thinking your product is cool, because then you're a fad.

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.

The transition strategies are more important than understanding what the outcome state will be.