Dessa has heard just about every question local music journalists could throw at her in recent years. We thought we’d get her cohorts in the Doomtree collective to ask some instead — the catch being they had to ask questions they’ve never asked before.




Q: At what age did you realize you were the most serious person in the room?

A: Probably about 5. Adults would say, “She’s 8 going on 40.” My latchkey supervisor tells me she once came into a room and saw me standing on a crate lecturing about the perils of Barbie, how damaging they could be to young girls. So I was already self-righteous at 7 or 8.




Q: Could you elaborate on why you are known as Coupon Man?

A: [Laughs] I am the member of Doomtree who secures our discount hotel rooms on tour. I get really irritated unless I can be guaranteed we have the lowest basement prices. My iPhone has five apps with which I procure those lowest of low prices.


Q: Now that we’ve all been in this rap game for a minute, what’s gotten easier or harder about being a musician since entering your 30s?

A: I know what I’m doing as an artist much more than I did in the 20s, which still leaves a lot of room for uncertainty. I feel more confident, like I have a vision, like I am daily amassing the skills I need to do this. What’s gotten harder: I know this career shortens your bread-winning years. This career is usually condensed into a couple decades, if you’re lucky. So I feel like you’re erasing your own birthdays trying to get more and more done.




Q: What’s your favorite movie trilogy?

A: [More laughs] He knows that I haven’t seen very many movies. Every time someone in Doomtree references a movie, they wait for me to Google the reference. So he’s calling me out.




Q: How have you most been influenced by your Doomtree dudes (not musically, but as a human)?

A: I use Stef [P.O.S.] as a model for a lot of things, especially whenever I find myself apprehensive about how to grow as an artist or treat other people in the industry. He’s developed such a graceful way of doing it. Lazerbeak is one of the most patient and nonjudgmental people I’ve met. Every so often I find myself trying to act like he would. I’ve learned a lot from Sims in the way he treats his relationship. He and his wife, Sarah, have one of the coolest, most clear-eyed marriages, and this business is good at undoing marriages. Paper Tiger is just a full-fledged New Yorker now. And Cecil [Cecil Otter], he says “no” very well.