Photos by Tate Carlson. Styling by J. Novachis.

Minnesota Business Editor in Chief Steve LeBeau interviews Doomtree Collective CEO Dessa Darling.

Dessa the CEO

By Steve LeBeau
Monday, July 27, 2015

Dessa Darling is famous around the world as an indie hip hop artist, writer and poet. She also happens to be a young entrepreneur. At 34, she is the CEO of Minneapolis-based Doomtree Collective. We caught up with her between out-of-town tours, and asked about the business side of her highly artistic life.
MNBIZ:Tell me about your role as CEO of Doomtree.
DESSA: Which is less important than it could be in any other organization because our hierarchy is essentially flat now. We're an LLC (limited liability corporation), but on the day that we had to file our paperwork, we realized that we all had to, just like in the Boy Scouts, adopt a position in the business management plan. We built them out without a hell of a lot of consideration. I work with Lazerbeak, who manages the operations in Doomtree on a daily basis, to do a lot of our strategic planning from a long-term view. I would say that I'm the second most-involved person in Doomtree in our business dealings.
MNBIZ: How do you actually organize your business structure? Who handles the budget and things like that? You make a living off this, is that correct?
DESSAWe do. Yeah, that's correct. Doomtree is an arts collective of seven people. We all make music, and most of us also have interests in at least one or two other disciplines as well. Doomtree’s primary objective as a corporate entity is to distribute the art that we make and to make sure that the seven members of Doomtree have the money that they need to finance their lives. For us, Doomtree, as an LLC, does whatever we, as human beings, need to have done so that we can pay our rent and do our grocery shopping and figure out how to share what we make with the world.
When we started, we weren't sure what to call the thing. Is it supposed to be a production house, technically? Is it supposed to be a band? Is it supposed to be a record label or a publishing house? Our answer has been, it will be as plastic as we need it to be to meet those two objectives: to share our work with the world and to make sure our lunch is paid. In turns, Doomtree has been a record label. It's been a publishing house. When one of us writes a book, Doomtree is the entity that fronts the money to get that book printed and finds ways to get that book into stores or directly into the hands of consumers. Doomtree has a website that services our fan base around the world. 
Doomtree also now works with a distributor to make sure that the music that we make can be found in some retailers and can be found anywhere online, like in iTunes or on Bandcamp. We work with graphic designers when we need to have the beautiful artwork to accompany our auditory projects. For us, I think we've been well served by resisting the impulse to state plainly what Doomtree is and to keep it flexible enough to make sure that our fundamental needs as artists are met. 
Lazerbeak does the bookkeeping and the daily operations. He makes sure that the quarterly taxes are paid and makes sure that we're paid after we've gone on tour, to figure out who gets what percentage of every t-shirt sale and to make sure that we're paid for our time on the road.
Then I help with a lot of the, as I mentioned, strategic initiatives. When we've got a big campaign up, Lazerbeak and I and the other artists of Doomtree — if they're interested — will sit down and do some planning and creative ways to share the news of the art that we're preparing to unveil, whether that means making a cool interactive game, whether that means doing a real live scavenger hunt, whether that means developing album art that can be used as origami to create a diorama, whether it means trying to figure out how on earth we're going to find 2,000 tiny paper ships in little glass bottles to mirror the artwork on our record covers.
MNBIZ: That's quite an extension in every respect of plasticity you talk about. You're flexible in brainstorming and in doing your marketing.
DESSA: Yeah, I think you're right. We don't have big budgets to take out some spots on billboards. We don't have the budget to have our ads in a lot of shiny, national magazines. For us, it really comes down to trying to find creative and artistic ways to share news of what we're doing so that people want to share it with their friends, because the campaign, in and of itself, is artful. 
MNBIZ: There's kind of a stereotype of the artist that cannot do business. It's like they have a half a brain, and then the business person has the other half. How can you manage to think business-like and create?
DESSA: I think there are artists like that, first of all. But I don't always find the objectives so different. When my brain is engaged in the development of a marketing campaign, it doesn't feel like the work is completely different from the work of making art. I know it does to some folks, but to me they feel very much the same. I'm preparing for a speech later this week, and it feels as creative as an endeavor in some ways as writing an essay. I'm working on a marketing campaign this afternoon, and I pulled over because I got excited about a really cool, new feature I thought that we could integrate into it. I think maybe if I was working at a bank, then creating our marketing plans would be an act of dry number crunching. But I work at a record label where even our marketing we want to be tasteful, clever, funny, smart, so it takes a lot of creative work to make sure that our brand is well represented in that way.
MNBIZ: You have a creative structure which helps.
DESSA:Yeah. I'm trying to think, would it be different if I were brought on...? And there is also the fact that this is my life. This is my primary passion. This is what I'd be doing even if I weren't paid to do it, or at least I think that would have been true at some point in my life. When I punch out of work, I go do more of it because that's what my life is built around. There's not a clear distinction for me between work and purpose and social connections, because the three circles of that Venn diagram all overlap in Doomtree.
MNBIZ: You majored in philosophy at the University of Minnesota, and I’m wondering if you have a philosophical overview of what you're doing, an orientation?
DESSA: For me, purpose is probably the most important driver. I don't use words like fun, let's say, maybe in my short list of adjectives to describe a rap tour, but it feels meaningful. For me, I think I'd prioritize 'purpose' a few rungs above fun. If there were a Jeremy Bentham or John Stuart Mill, where instead of the utiles of 'happiness,' they had been done 'purpose' as the general metric for a moralistic worldview, I would have been on board. How to do that? I don't know. Defining words like 'purpose' and 'meaning' are really tough. I know probably that's where we're going next, and I say I'm ready to do it even as I articulate it to myself. I know that if you were to imagine an annual report or you've got a Cartesian plane and an X and Y axis, but for me trying to maximize meaning and contribution and purpose is the major way that I evaluate myself, in addition to being mindful of how much money I'm making and if I'm working in a way that my body can remain healthy, which is tricky in this industry.
MNBIZ: It seems that a major goal for most businesses is finding good talent and keeping them happy. By virtue of being a collective of talented people, you've already beat what most businesses are looking for.
DESSA: In part, I think it's because we're a business second. The business is instrumental. It's not the objective. Art is the objective, and we need the business to make and share the art. We're already operating in a slightly different paradigm. Nobody said, "Let's make money. How should we make money? Let's write songs." We all said, "Hey, let's write songs. How should we make money?"
MNBIZ: You once said that for your business, it was friendship first, then music, and then finally money, as far as your priorities go.
DESSA: Yeah.
MNBIZ: Is that still true today?
DESSAYeah. That was told to me when I was invited into the collective ten or 12 years ago, and it remains true. Obviously, it's true in different ways. We didn't have mortgages when we made that Neverland blood pact when we all became blood brothers in a living room at 20 and now that the financial responsibilities of being an adult, but for some of the guys, for being a provider for family. I don't want to understate those. But we've remained friends, with the most important thing is great music, good art.
MNBIZ: Speaking of paradigm change, it used to be that the music industry worked a lot differently before the digital age. You came to maturity in the digital age so ...
DESSA: Right, yeah. In interviews, I'm often in this strange position of talking about a model that I didn't quite participate in. Because as the big major labels were in the process of a pretty serious collapse, that was when I was learning to perform and sing and rap. We tried to get signed. When I first started, the objective wasn't to begin a music label. I didn't think that was how to win. I thought you were supposed to get signed, so we sent out demos, and we tried. We got a couple of interested parties that never resulted in an inked contract.
As the years went by, we realized that [out of] necessity, we had built the infrastructure and practices that we're actually doing what we would have asked the label to do: promoting our work, distributing our work, maybe getting us some shows, making some cool merch. We always thought, well, until we get signed, we'll have to figure out how to do some of these things. Then you fast forward five and 10 years and you realize, hey, we got pretty good at these things. If somebody wanted to sign us, they'd have to cut a hell of a deal.
MNBIZ: So you turned into an entrepreneur by default.
DESSA: Exactly. We weren't being hired, so we hired ourselves.
MNBIZ: I think looking back and, once again, generalizing on history, a lot of the artists that got very successful signing to a label didn't handle their money very well at all. They didn't appreciate the responsibility of it.
DESSA: Some of them didn't get a heck of a lot of money. The problem with artists is that most of us are driven by a love of art which makes it complicated, because that doesn't drive very well with an economist's understanding of human motives, which is, well, if they're not paid enough, they'll just stop doing it. That's actually not true of a lot of artists because our bottom line isn't necessarily financial, and a lot of people still play in bands that they have to lose money to keep afloat. Because artists are driven by something other money, it makes them vulnerable to people who might exploit them. If an artist wants to share his or her work, you can get them cheap sometimes or you can get them on lousy terms sometimes. You can take advantage of that fact, knowing that they're willing to share their art and they'll do so even in a financial arrangement that may not aggressively suit their needs.
MNBIZ: One of the general traits I see among young entrepreneurs is a devotion to social responsibility that used to be an option. Now a lot of them are building that into part of their business plans. They have the new B Corps. It sounds like it's shifting with the generation that may be for parallel reasons. The major businesses don't seem as stable as they used to, and so therefore they're doing it on their own.
DESSA: I dig it. I think it's awesome. I don't know anybody who started a B Corp yet, but I've just read about it online and I think it's awesome.
MNBIZ: They put that into their mission statement.
DESSA: We've never drafted a mission statement or a vision statement per se, but for the past 10 years, part of our year-end annual show revolved around making a donation to charitable organizations based here in Minneapolis. I'm working also with GreenNotes, which is a program that helps artists fold in social campaigns into their touring and into their jobs. I was able to tour organic farms and markets around the southeast parts of the United States to talk to farmers about their understanding of organic and local and seasonal and to learn about how our food systems work and to learn a little bit more about why people object to the way that our food is grown and distributed here in this country.
It's definitely been part of our culture and in the arts particularly. It's so much a part of the worldview, I think, of artists based here in Minneapolis that social change is in the air. Very often as an artist you have an opportunity to use your platform for a worthy cause.
MNBIZ: Plus I think that your art in itself is probably an element of social change. I mean it's mental change if you get people thinking and feeling.
DESSA: I hope so. Even sometimes for me, a voice by someone who seems very different is an act of underscoring some sort of a shared human experience. If I hear a woman in Bangalore write a song and I thought, "Oh, I totally know what she means in that chorus." Gosh, I wouldn't even know a woman from Bangalore with such a different set of experiences might have that same feeling too. I guess there really is some shared kernel of what it means to be alive and human. I think that forging connections between really different kinds of people is part of the work that music does, even if that's not its primary objective. Even if it doesn't set out with that agenda, I think that that's what happens.
MNBIZ: You once talked about some financial advice your father gave you: “Keep the overhead low.”
DESSA: That was hugely helpful for the beginning years of my career. It might be the same in every industry, but in this one it felt there was a hockey stick shape to the annual earnings. It stayed low for a long time before finally starting to rise and then rise significantly. So learning how to live on very little and then learning how to live on a little less was an important part of making a career in music work. Everybody knows when the happy hours are, where the cheap neighborhoods are, and when there are sales and specials and how to barter. 
When I first joined Doomtree, I watched the way that P.O.S. — another member in Doomtree — was able to conduct his life often without ever using any money. He'd trade guest list passes to a show for a movie. Then he'd trade that copy of the movie for a sandwich. Okay, now everybody's fed. Then he can share the free pizza that he got for entry to a concert that night. All of a sudden, based on his system of bartering, he was able to handle all his obligations. I thought, whoa, it had never occurred to me that I could get so much done without any money.
MNBIZ: Bartering, the principle of trade.
DESSA: And for very complex trades, where he's got a constellation of unmet needs. The unmet needs of his friends are in his head at all times, and so if he can get a trade done that involves six exchanges but everybody leaves happier, then all the more power to him.
MNBIZ: When you look at the broader world, especially things have changed since the big financial crunch of the recession of 2008, I've actually seen the CEO of RBC Wealth Management, John Taft, write a book basically saying the same thing. You ought not put money as your purpose. You ought to put the public good as the purpose and then use money instrumentally, which is what makes sense. He's saying that all the major CEOs of any worth agree with him, but it's kind of hard to believe it.
DESSA: Yeah, sure, exactly. I'd effortlessly affirm what he said. Money is an instrument. Anybody who thinks differently is not someone who I'm probably inclined to spend a lot of time with. It's an important instrument, but it is instrumental. As for the C suite executives of the world, I suspect that fewer of them hold that position than indie rappers.
MNBIZ: Do you have any ethical reflections on that? How do you handle the ethics in general?
DESSA: Ethics is what first drew me to philosophy. I think that some of the biggest ethical questions that I face in my career do have to do with money and with beauty and the way that beauty is commoditized for sale. As very fair-skinned, college-educated rapper, one of the questions you have to ask yourself to feel like you're being responsible is, “Am I reaping the benefits that are, in part, a product of other people's hard work?” Which is a fancy way of saying, am I one of these people who's co-opting Black art and making a living from it, when other Black artists haven't been able to because of institutionalized prejudices and unequal access to resources? And if I am, what do I do about that? You can't take off your privilege like it's a dress and hang it on your door and then leave your house without it. And I am privileged but I try to find ways to offset my privilege in the same way that one might offset the carbon footprint they create by driving in their car on petrol. 
Those are some of the questions I think about. Does that mean giving money to organizations that help try to close the achievement gap at home? Sometimes. Sometimes it means working with organizations here, like the Southside Family Nurturing Center, that work to try to give kids who are having a rough few years, make sure that they have access to speech therapists and a good meal and some adults that can provide a safe environment for a few hours every day. Sometimes it means saying I'm not going to take this job. You should ask someone else. I don't do that very often, but I have done that because I was asked to give the Nobel Peace Prize Forum keynote speech a few years ago, and I gave it. I was really proud of having been asked, and I was proud of the job that I did. I was also aware of the fact that there might be other speakers in the Twin Cities who ought also be considered, even if perhaps they weren't on the radar of the selection committee. When I was approached, I said, "Wow, this sounds awesome." I told them to ask Toki Wright. If he wasn't available, then ask Brother Ali. And if he wasn't available, then I would do it.
MNBIZ: Did they follow that protocol?
DESSA: They did, yes. They both weren't able to do it, and I did a great job. We're all subject to the limits of our own Rolodexes. If I have to hire a plumber, I can either look in the yellow pages or I can say to my friends, "Does anybody know a plumber?" Maybe between us, we'll all know of three, and then those will be the trusted networks that I go to. All of us build our networks based on the accidental circumstances of where we went to school, and where we got our first job, and what are our husbands or our wives or our partners ... Those are all circumstances that are informed by class and race.
MNBIZ: Most people don't think about that. I think that's one problem of the classical capitalist mentality is that you shut off your feelings and thereby shut off your conscience.
DESSA: I think that's lousy. Yeah, I know what you mean. Sometimes we compartmentalize it, like I take out my conscience on the weekends when I do my youth work, but the business world has its own set of rules. I don't think anything we do is apart from our existence as moral creatures. Everything is subject to those rules. I would not present myself as an exemplar of the moral life. I would count myself as someone trying to strive towards one.
MNBIZ: I like the variation on the offset carbon footprint. You said another phrase. What was it? The commoditization of beauty. Would you tell me more about that?
DESSA: When you look at a magazine, we see a lot of representations of the female form that are often a product of a lot of post-production editing, and the standard of beauty is just really hard to hit. Hard to hit for young and healthy people and harder to hit for not so young and not so healthy people. I always thought that kind of sucked because it leaves a lot of people feeling unhappy or not good enough, and it promotes a culture of fear and sadness: "I'm not pretty enough to be able to meet the standard of my friends. I'm not pretty enough to get a boyfriend." It just creates a lot of unhappiness. 
I think it's a regrettable part of living in the American era is beauty culture just feels like it got out of hand, out of control, and it ran rampant. Now that I'm part of the entertainment culture, I find it very difficult to always have the nerve to practice what I preach, as I look at photographs of myself and I see touched up versions and untouched up versions, and I decide what I'm going to wear on stage. I decide what's sexy and what's too sexy and what feels like the appropriate expression of sexual comfort and what feels maybe exploitative. Those are tough. Those lines are difficult, so deciding how I exist in the world and the images that I share of myself. 
I'm not sure exactly where I land yet, except that I initially thought, "Well, I don't want part of any of this," so I used to take the stage in boy's clothes, very baggy, not androgynous, male, masculine clothing. 
Then that felt like, "Wait a minute, you're letting this whole beauty culture dictate how you present yourself, even if you're doing so in an effort to buck it or thwart it, you're being only compensatory. You're not cutting your own path. You're just choosing the opposite tact." 
Then I thought, "Well, how do I want to dress on stage?" I'm still navigating that. I actually like the idea ... because sometimes I'll do a high-fashion beauty shoot. It is fun to make those images. There's a big artistic opportunity there. At the same time, that's not how I look every day, and if I imply that it is, then I'm contributing to this unreachable standard of female beauty. 
I like the idea of participating in all of it, in both. If I'm going to do a really beautiful, curated shot where I'm in an amazing dress that's got clamps in the back that nobody can see from the vantage point of the camera, and I've got my hair perfectly styled in a way that it would never survive even the slightest exhale from a passing stranger, and I've got my makeup done in these amazing ways that are hiding the rings of fatigue under my eyes ... Then if I'm going to do that photo, then I should also do a plain-faced photo so that if both exist in the world. When you see stars without makeup and everybody puts it in a magazine, I think that actually does a service, so we can say here's a very curated kind of beauty, and lest we all not lose our minds and imagine that's how women actually look on a Tuesday afternoon, here's another version of that same person in their jogging attire looking winded after doing half of Lake Harriet.
MNBIZ: I'm not sure I understand that fully because it seems to me that when you're performing and expressing your art, you don't do that all day, every day either. Sometimes you just read a book and you wouldn't do that on stage. It seems to be how you present yourself appearance-wise is another artistic expression.
DESSA: Yeah. I would say, however, that we all have access to our own private appearances. If we only grant other people access to our curated, public appearances, then we can do nothing else but create an entire culture of inadequacy. Which is to say, if I never let anybody see me reading a book, and all women do that, here's my curated, high beauty, carefully cinched, girdled and made up public presentation, and never grant access past that, then every 15-year-old, who has access to only the public images of how women ought to look, can't help but feel like, "I am not cutting it here," because then we limit the portal of the way that women look to an unrepresentative and impossible standard.
MNBIZ: Just as your business structure is so fluid, you seem to melt between ethics and aesthetics. All that stuff is kind of muddled together.
DESSA: I think for women ethics and aesthetics are very much married, more so perhaps than men. There are so many moral questions in beauty and in seeking beauty. We would consider vanity a sin. Yeah, well, there we go, right? To emphasize too much importance on a particular form of beauty is a sin. The way that beauty fits into your life is fraught with a lot of examples, I think, for ethical conversations. I think ethics can come apart pretty cleanly from beauty, but I don't think that beauty can come apart entirely from ethics.
MNBIZ: You hear about the painters that nobody sees any of their paintings until after they're dead and gone, but you have instant feedback. That ought to have something to do with how you craft your work and your appearance.
DESSA: Yes. I've probably also made myself more available to instant feedback. Yesterday, for example, I finished two poems and I decided I would put them both online for three hours on my Facebook page to see what kind of response they got. Then I would take them off so I could finish polishing those drafts. For me, the immediate reaction of the social networks is an opportunity to connect. It is a way to try out new ideas. But, yes, it absolutely can be a distraction, burdensome and demoralizing.
MNBIZ: The key thing that strikes me is that you have autonomy. Can you comment on that, the value of freedom at work, the freedom to create, the freedom to say what's on your mind?
DESSA: I think one of the best parts of my job is I can say anything that I believe, and although I'm grateful for a lot of help I've had along the way, I don't really owe anybody anything. I don't owe a listener who liked the last album. I'm not morally obligated to give them one that they'll love this time. I don't owe a big record label the next 10 years of my life because I signed a contract. I think beholden artists might have their bravery curtailed. If I owed a lot of money to a king, if I owed a lot of money to a label, if I owed a lot of money to Coca-Cola or something, I'd be scared to make something they didn't like. As it is, I'm terrified to make something people don't like, and I don't owe them anything. I think brave artists make interesting work. I'm eager to try to put myself in a position where I can be brave.
MNBIZ: Push your bravery to the limit.
DESSA: Yeah, and this business will test that. It's uncertain. You are fired every night after you get off stage and rehired every day. It's very unusual that you would know where a paycheck might arrive from five months into the future. Your earnings are determined insanely by a totally capricious market. People will offer you, for exactly the same one hour of service, a rate that might be 20 times more or less than the last rate you were paid two weeks ago for exactly that service.
MNBIZ: Do you count your revenue streams? Is it mainly through a live performance or is there any product sales, record sales, book sales?
DESSA: Yeah. I have quite a few tributaries that lead to the stream that powers my life. Some money that I make is from live performance. Some money that I make is from the digital or physical sale of my records. Some money that I make is from selling merchandise that isn't music, like a T-shirt or a bit of magnetic poetry with my lyrics on it or a tote bag or a skeleton key pendant that references one of the choruses from my song. I make some money from online streaming like when people play my music on Spotify or Pandora, although I could buy a really great cup of coffee usually with that money. 
I make some of my money as a speaker or as a teacher, giving speeches to collegiate audiences or to corporate audiences or to rooms full of other artists. I traveled to South Africa to talk to the artistic community in Port Elizabeth last month about what was working here for us, find out what was working there for them. I sometimes make some money as a writer, either by selling a column or an essay or a poem or by selling the collections of poetry or essays that I've written.
MNBIZ: What's the largest stream right now, the largest tributary?
DESSA: Live, live shows. I participate in a pattern that is much bigger than me when I say that. That has become true for most artists.
MNBIZ: That's a lot more work.
DESSA: Tell me about it. I think this year I will probably play something like 150 or 220 shows, somewhere in there.
MNBIZ: That's like being an athlete.
DESSA: Yeah, an athlete with a hangover.
MNBIZ: That's probably true for a lot of them as well.
Dessa: Yeah, sure. There is a kind of a sharky aspect to the job in the way that if sharks stop swimming, they die. Artists are asked to continue to tour to earn their living wage. That makes for some good live shows. It makes for a lot of touring artists. I think it also potentially penalizes artists who might be really good at composing and recording music but don't have an interest or a particular talent for serving as entertainers for a room full of people. I think that sucks because I bet it's possible to miss out on some really good music. I think also it disproportionately affects women who might be inclined to start a family, because whereas the man can tour just a few weeks after the birth of a son or a daughter, a female musician, unless she's touring in some pretty luxe buses, can't do the same.
MNBIZ: I just realized you're a migrant worker.
DESSA: Yeah, God. I'm going to use that phrase. Yeah, yeah. I mean you're right.
MNBIZ: You travel around to where the work is.
DESSA: Yep, and you can't stay too long. Usually, we'll play between six and seven nights a week when we're on tour. 
MNBIZ: To what extent do you deal with other entrepreneurs?
DESSA: I think at this point, at least as a musician and as a writer, I would say that probably the lion's share of my business communications and my business interactions happen with entrepreneurial people, whether it's someone who has started a screen printing outfit to make the shirts and the bags that we use as our merchandise, or whether it's my manager, who came home after a stint in the Navy and decided to start up an artist's management company, or whether it's the people who hire me around the country to perform. Usually they do so by adopting an enormous amount of risk as individual promoters. Yeah, I think a bunch of my job is built around partnerships with other entrepreneurs.