1. What's your favorite part of a typical day?
Walking to University Avenue in Palo Alto for breakfast and mulling over ideas.
2. What part of your job would you gladly give up?
Arguing with companies that want to acquire Y Combinator start-ups. Even the nicest big companies behave like assholes during an acquisition.
3. What skill would you most like to improve?
Y Combinator is pretty good at picking start-ups by comparison to most other people. But they're wretched, and we're merely bad. I would like to advance from bad to mediocre.
4. What's the simplest thing you never learned to do?
Unix system administration. It's the computer equivalent of sweeping the room, but I've never learned it.
5. If you could go back and do one thing differently, what would it be?
I wish I had taken advantage of all the free time I had in high school and actually learned stuff, instead of spending so much time hanging out with friends.
6. What keeps you up at night?
A thousand little tiny worries to do with 145 start-ups. It's like having 145 kids.
7. Who gives you the best advice about your business?
My co-founders Robert Morris and Jessica Livingston.
8. What accomplishment are you most proud of?
There's nothing that I've done that seems really big. Y Combinator is pretty good. Some of my essays may be good. But I doubt I've done anything anyone would care about in 100 years.
9. If you were going to start a company in another industry, what would it be?
I keep telling myself not to do this, but I've often thought of starting a publishing company that makes books that are actually nice physical objects.
10. If you were made dictator for a day, what's the first change you would make?
My impulse would be complete transparency for everything that goes on in Congress.