Figure out how you're going to make your living on the side. Develop skills to support it: economic skills or other skills that you're going to need. If you want to be a film producer or director, you're going to have to lead people, you going to need to know how to run an organization. How are you going to learn that? Go and run WHRB, or The Crimson, or the Young Republicans, or whatever the hell you're interested in.

THC: Do you ever doubt that you made the right decision?

RG: Oh yeah, all the time. I still doubt it. I'm 40 years old, I don't own a house, I don't own anything! I have a van with 170,000 miles on it. I own a bunch of albums. One of my roommates from college is now almost a billionaire. He became a venture capitalist in Silicon Valley, and now he's going to be worth a billion in a couple of years. And God bless him, it's great. That's what he wanted to do, he set out, and was in the right place at the right time. When I'm hanging out with him, I think, "Goddamn, I could have done this." Maybe not been as successful as him, but I know I could have done it.

THC: Do you think he might envy what you do?

RG: I think so, a little bit. He's so damn successful that it's hard for him to envy anybody. I think my friends from Harvard that envy me are the ones that have gone into business and haven't succeed on that level, or have wound up working for big companies. And I envy them for the fact that they've got pensions coming and houses and there's a point at which they're going to be able to retire and not have to do it anymore-and it's not too far from now. For 40 years old, some of them could retire today, and many of them will be able to semi-retire in 10 or 15 years. I'll still be struggling to pay the rent. But I've got a lot of stories. And I've got a legacy of music that seems to matter to some people. That's something.