How to teach people to do what hasn't been done is a great riddle.

You become a great writer by writing.

Whenever I talk to people who founded a company, I often like to ask the prehistory questions 'When did you meet? How long have you been working before you started the company?' A bad answer is, 'We met at a networking event a week ago, and we started a company because we both want to be entrepreneurs.'

Don't bother starting the 10,000th restaurant in Manhattan. Find something to do that if you don't do it, it won't get done.

If I had known how hard it would be to do something new, particularly in the payments industry, I would never have started PayPal. That's why nobody with long experience in banking had done it. You needed to be naive enough to think that new things could be done.

When I was a kid, the great debate was about how to defeat the Soviet Union. And we won. Now we are told that the great debate is about who gets to use which bathroom. This is a distraction from our real problems. Who cares?