1) No. We'd do charitable donations individually, not through YC.
2) I don't know of any, but that doesn't mean there aren't any.
3) I like the stuff I work on. You don't need a respite from work you like.
4) We wouldn't trust anyone else enough. We'd rather see if we can cook up some clever way of doing everything ourselves.
5) Write essays.
6) I haven't given up on painting. But the web has opened a window for writing essays that never existed before, so I decided I'd spend a couple years mostly writing.
This may well have been someone kissing up, some of the questions weren't well researched, and this site probably isn't a great place for a personal interview (as opposed to an Ask YCombinator-type open question). All that aside, I would have liked to have seen better answers for two questions.
For instance, it seems possible that a nonprofit startup might be better than a large, existing nonprofit at solving a problem YCombinator's founders care about. And funding a nonprofit startup is not necessarily the same as making a donation. It could be, but it doesn't have to be.
The spare time question might also deserve a more thoughtful answer. After all, the whole point of news.ycombinator.com is that people interested in startups also have other interests. Are there patterns? Are there things to do in one's spare time that seem to go along with creating successful startups, things one wouldn't necessarily expect?
We like startups that have a benevolent angle. But it would be weird to have actual nonprofits mixed in with the regular YC startups. The priorities would be so different; it would throw us all off to have to be switching gears when we talked to them.
As for the spare time question, that was supposed to be a thoughtful answer. That's what I spend most of the time on that I don't spend on YC. From what I've seen of startup founders, there is no pattern to what they do in their spare time. Most have eclectic interests, if that counts as a pattern.
I remember in an essay you wrote a long time ago (I think the one about "doing things you love") you said that if you've found something you love doing, then the "concept of spare time will seem mistaken". So you love working with Y Combinator, but still have spare time? :-)
BTW I really liked that essay and if you had any new thoughts, a follow-up would be great.
2) I don't know of any, but that doesn't mean there aren't any.
3) I like the stuff I work on. You don't need a respite from work you like.
4) We wouldn't trust anyone else enough. We'd rather see if we can cook up some clever way of doing everything ourselves.
5) Write essays.
6) I haven't given up on painting. But the web has opened a window for writing essays that never existed before, so I decided I'd spend a couple years mostly writing.