Fame & Fortune: Jesse Winchester American music's most identifiable draft-dodger
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Bankrate: Have you always managed your own money?

Winchester: I don't budget. I don't really think about it very much. I think of money as another way to express love or appreciation. A hit record is good, you get money for it, because other people like the song, but you have to keep money moving, you can't hang on to it. So if you know somebody who makes beautiful guitars, you pretty much are obligated to support him by buying one of his guitars. If he's a great plumber, you have to hire him even though he might be a little more expensive because he cares about his work. It's a way to express appreciation like that. I try to keep that attitude, and if I have something I want, I buy it and don't really think too much about tomorrow. So far, so good. They haven't come to lock me away yet.

Bankrate: Are you a Canadian citizen now?

Winchester: I'm a dual citizen actually. You only pay taxes in the country in which you live. The transition back to the U.S. was complicated and it's still going on. I had a Canadian company which owned the copyrights to my songs, and that's been a hassle changing that over and dealing with that. At the moment, I have two accountants, one in the U.S. and one in Canada, and that's a hassle. All that kind of stuff just drives me crazy. I'm not a good businessman because I just don't want to be bothered, more than anything. I'd love to be rich but I'm just not willing to do what it takes to get there, I guess. It's interesting, the people who play the stock market; I love the idea of sitting there reading the paper in the morning and see where there has been a series of heavy storms in Indonesia where they grow coffee or something, so you get your broker on the phone and say, buy coffee futures or something. That sort of thinking appeals to me. If I could just knuckle down and do it, it would be fun. But it's just not going to happen. By the world standards, we're right. But as Saki said, "I'd like to be rich by my own standards."