Are your family and friends supportive of what you do? Yeah, but it took a while. I had to call my mom and say, “Thanks for helping me pay for college, but I’m in a thing called Doomtree now!” (laughing) It took a few years, but I remember making my dad a mixtape of rap music and trying to explain what else it was besides what he sees on TV. Those first few years, as far as the business and income side of it goes, were a pretty slow build. I probably didn’t reassure them too much because I was still figuring it all out. But in the past three or four years, I’ve been able to remind them that I’m okay—I don’t need a Christmas check anymore.

What was the progression from starting out in Doomtree to being able to support yourself with music like? In the early days of Doomtree, we burned our own CDs, made copies of the album art on a photocopier, and slid everything into empty jewel cases. Everybody used their own computer, or a family computer, until the day we found somebody who let us borrow a 10-CD burner, which decreased our production time from about 4 days to 10 hours. Once we reached a point where we thought we could move 1,000 CDs, we took a master recording to a company to duplicate them professionally.

For shows, our growth was informed and directed by organic demand. When we could draw 30 people, we played at tiny venues; then when we could draw 500 people, we started moving up to mid-level venues, which is still where we are in a lot of cities around the country. Here in Minneapolis, where most of us live, we can usually play larger venues for 1,500 or 3,000 people.

Are you currently touring? Yeah, we’re touring for our most recent record that came out in January, All Hands. We’ve cut the tour up into a couple of legs, which is nice. We’re currently touring the West Coast.

Do you feel a responsibility to contribute to something bigger than yourself? Yes, neurotically. The fear of death is the subtext there. (laughing)

Are you creatively satisfied? For brief moments. It feels awesome to finish something that I think is good, but it’s tough sledding to get there. I don’t feel relaxed or happy when I’m sitting in front of a computer screen writing an essay or in front of the piano figuring out a bridge. I mostly feel frustrated that I don’t know what I’m supposed to do to make it awesome. The moment I figure it out, I experience a great afterglow for a few hours, but then it’s over. I’m extremely proud of the good work I’ve completed, but the actual creative process is kind of a slog for me. The actual act of creating is all about not getting it right until the second you do, and then the creative process is over. Afterwards, it’s like, “Tight. Time for dinner.”

What advice would you give to a young person starting out? I’m a little wary when I’m asked to give advice because I know that there are so many different ways to get there. That said, if I were to give advice, it would probably be similar to some of what I said in the commencement speech I gave at my alma mater a few years ago: learning to live inexpensively is good form for a creative because money is going to be tight in the first few years. As human beings, we should be careful about how romanced we are by advertising. I know I sound like my mom in her sod house right now, (laughing) but paying attention to how much you let into your head and being skeptical of the culture in which you live is important, and part of that skepticism would sometimes entail frugality. You don’t need the name brand shit. Once you’re making money, it’s fine to re-evaluate your spending decisions; but in those first few years when money is going to be scarce, you will buy yourself hours of creating if you can forego the nice car or the latest shoes and live a little under the radar.

How does living in Minneapolis influence your creativity or the work that you do? It’s a little tough to say, because I haven’t lived anywhere else. Minneapolis is my control group and my experimental group, so I’m not sure how it would change if I lived elsewhere. Minneapolis has provided me with a great foundation—they really care about the arts here. For example, people generally vote yes during local elections to devote some tax money to supporting the arts. When people go out on dates or out with friends, they usually see a local band. That isn’t the case in every city, but in Minneapolis it’s baked into the culture. There’s an amazing number of good local bands here, and more hip-hop than you would think. Rhymesayers is based here, and they have artists like Brother Ali and Atmosphere showing the hip-hop community that an artist-owned and -operated indie label can put somebody in the top 10 Billboard charts.

I have been thinking about spending some of my time in New York, and this year I actually started renting out Airbnb’s there between tours. After traveling over the past 10 years, I have to say that I do like some of the onslaught of sensation that happens when I’m in places like New York. When I’m stuck on a song or a story there, I can walk around and see a three-legged dog or a pregnant woman smoking a cigar or something that might jolt me out of my writer’s block and put me back on the page.