Wilco’s lead singer, Jeff Tweedy, has figured out a few things in life. In the most recent issue of Grid magazine, I profiled Tweedy the entrepreneur, examining how he’s built a sustainable, self-reliant business around Wilco’s music—a tricky proposition for any mid-sized act in the age of Spotify, as attested by the industry vets who discussed the article with the New Yorker.
Tweedy, a practiced interviewee, knows the power of a telling anecdote. When we first met in March, in Wilco’s loft space in northwest Chicago, he shared a story with me that didn’t fit in the article.
I asked Tweedy, whose band has a gold-certified album and two Grammys, how he defined success. Here is his reply:
I’ve felt successful for a long time, because I’ve been able to not work at any other job and take care of my family. My wife hasn’t had to work for a while. But before that she did something she loved to do, she had [the music club] Lounge Ax.
I think that that’s how it’s been defined for a long time. There was a moment when we bought a house in Michigan—we’d had a vacation cabin in Indiana that was kind of far from the lake, and then we bought this house that was a little closer to the lake—and I went for a bike ride by the houses right on the lake, Lake Michigan, and there’s these giant houses with heliports and stuff like that. And I was like, ‘Oh wow, these are beautiful.’
Then I realized that that’s a game that you’re going to lose, if you start thinking of success in those terms, in terms of your acquisitions. I know that there’s people who do that, and I just don’t see how any of them are ever happy—if we have a heliport, so-and-so has two heliports, and I don’t think there’s any end to it. And I was happy to have had that realization, and very, very content with what we have.