Latina to Latina

Why Dessa Is So Much More Than an Indie Rapper

Episode Notes

She says her music is driven by “connection, communion and lost.” But listening, really listening, to one of Dessa’s albums and then drilling down to a single song, leads you through a tunnel of convulsing rage, unanswered love, and philosophical rifts on your place in the world. She brings that intense presence of heart and mind to this revealing conversation.

Follow Dessa on Twitter @dessadarling and IG @dessa. If you loved this episode, listen to Latashá and iLe for more on music. Show your love and become a Latina to Latina Patreon supporter!

Episode Transcription

Lyrics (Dessa): 

We lean to turn in the velodrome
All lines are curved in the velodrome
We pitch and roll, wheels
Flesh and bone
Total control and it’s
It’s ours alone
We lean to turn in the velodrome…

Alicia Menendez: 

That’s a track from Dessa’s new album, Sound the Bells, which she recorded with the Minnesota Orchestra. Dessa’s hit the Billboard charts as a solo artist, a member of the Doomtree Collective, and with her contribution to The Hamilton Mixtape. She’s also got projects ranging from the scientific and experimental to a collaboration with Izzy’s Ice Cream, which is all to say that Dessa is a person and an artist who defies categorization. 

Lyrics (Dessa): To see if I might chime.

Menendez: Dessa, there are so many places we could start this conversation. So first, tell me. Were you always a person who was firing on like 10 cylinders? 

Dessa: Oh, man. I mean, I think I’m naturally curious. I would say that I have been interested in more than one thing at a time for a lot of my life, but I think we receive the message when we’re little that your work life is gonna follow one trajectory. You’re not gonna be like, I don’t know, a physicist and a bespoke furniture designer, professionally. But you totally can. 

Menendez: Right. Did you have anyone growing up around you who had that type of life?

Dessa: I did. Yeah. I mean, nobody who was raking in the cash, but my dad had really wide-ranging interests when I was little, too. He had a really strong idea about what vocation and work is, and he said, “Your job…” Well, he didn’t say your job. “Your goal is to do what you love, and find someone who’s willing to pay you for that.” That’s what work is. That’s what work means. You know, he was a musician. He played the lute, which is like the Elizabethan precursor to the guitar. Yeah, it’s just kind of esoteric from jump. 

And then, after that he became a glider pilot, which are those planes.

Menendez: Sure. 

Dessa: Sure. As you do. Those planes without motors. It was long days to earn enough money to raise a couple kids doing those things. But he dug it, and I’m sure that part of that stuck. And also, I think I’m just his kid. I really want the hours that I spend working to count. Not to only finance the hours that I’m not working. 

Menendez: Is your mom like that?

Dessa: I would say to some extent, too. Yeah. I mean, she maybe naturally had a skill that was more lucrative. She worked for Honeywell, and then the St. Paul police department, which is in Minnesota. She’s a really good communicator, so she did television reporting stuff, and then public relations stuff, but she’d always had this side interest in environmentalism, and so even when I was a little kid, like before organic was a thing that we knew, she was part of real radical groups to try to change the food system in the U.S., and she would drag me to these meetings where all these home gardeners and farmers would trade heirloom seeds, called Seed Savers Exchange, so that the biodiversity of the planet didn’t expire as everyone else planted monocrops. Yeah. 

Menendez: I think of myself as a creative, but you make me feel like such a square, and never more than when I hear you talk about Doomtree. In your own words, what is it? 

Dessa: Okay. I would say Doomtree is a collective of artists that make hip hop music and other stuff, too. It’s sort of like whatever the seven of us want to make. Doomtree is the vehicle to try to release and promote that into the world, so it’s a friendship clan. 

Menendez: Does it complicate things, though, when it’s a friendship clan, and then all of a sudden the friendship clan is making money? 

Dessa: It’s a good question. I’ll tell you when we hit it. No, I mean… Yeah, when I was brought in, I was told it’s friendship first, and it’s music second, and it’s money third. Now, granted, that is way too pat and trite a motto to have served as an airtight, fool-proof guide. But it does mean something. 

When I first saw Doomtree, before I was a member of the group, there was very much like a kind of a punk ethos. They looked sort of punk rocky, and there was a lot of bartering goods and services to get the label made. You know, so like when somebody had new music, it was like, “Do you know somebody at Kinkos who could be compelled to photocopy our album art if we brought them sandwiches?” You know?

So, there was just that DIY, get it done vibe. 

Menendez: It is so interesting to watch those performances, which are bombastic, and loud, and there’s this joy to it, and then the contrast of you as a solo artist, which is, as all of my favorite music is, much moodier. Do you feel like you’re sort of one person with them and another person when you’re a solo artist? Or do you see a through line between the two?

Dessa: I think it feels very much like my appetite, aesthetically, was met, was fed. You know? Like I’ve always been interested in anger, love, beauty, and sadness, and their titrated really differently in those two projects, but Doomtree has some super pretty choruses, and the producer, Cecil Otter, who’s a member of the group too, he makes some really beautiful, cinematic, soaring stuff. 

But you’re right, it is like I’m moving my body talking to you now in a sound booth. It is very… It’s kind of like half sport, very athletic stuff, and that’s true of a lot of that era of rap music, you know, that I think I would sometimes leave those shows eager to build a pretty chord, and do some more patient stuff, too. But after a while of doing pretty stuff, I start to get antsy to make something that’s a little bit mean. 

Lyrics (Dessa): I ain’t afraid of it

I don’t drown, won’t stay down

Heat finds a way to rise somehow

Scan the crowd as I’m coming out and I 

Don’t see too many rivals now

Menendez: Do you consider yourself indie by choice or by necessity? 

Dessa: Ooh. They’ve blurred over the years. That’s such a cool question. 

Menendez: I bet. 

Dessa: Yeah, because you’re right, in one way it’s like I’m indie because nobody, no majors were interested, would be the default mode, right? But I would say that on the few occasions that I’ve had with major distributors or industry folks, I was apprehensive about concessions that I might be asked to make.

Menendez: Because the labels are like, “I need a top-100 hit.” Is that it? 

Dessa: Yeah, and it’s just, it’s risky. Taking big risks is not something that people who loan you money want you to do, and-

Menendez: You mean getting up on stage with an entire orchestra and recording an album?

Dessa: Even just like, “I’m gonna do an album in Farsi.” Well, I don’t know how to do that, but if I were someone who spoke Farsi, like, “Well, that’s not gonna get us a radio hit. That’s too risky. I don’t want you to do that with my money.” And you know, when you get a record deal, essentially what you’ve got is borrowed money. 

I would say I’m not… I don’t really have like a middle finger up to every institution. That’s not it. But the kind of risks that I’ve wanted to take, yeah, I don’t know if they’re appetizing to major players. But it’s also not like I’ve had like 18 deals on the table and said no and then stormed off, like Joan of Arc in a blaze of self-righteousness, either. 

Menendez: So then, how do you make the business of making music work? 

Dessa: I would say a lot of revenue streams, like I don’t know if that’s too nerdy to get into, but-

Menendez: No! Get into it with me. 

Dessa: But it’s like the way that you actually pay rent, it’s almost like there’s a lot of tributaries that contribute to the monthly income stream. You know, we’re at the end of the year right now. Some of the money that I’ve made, I made playing concerts, so like people at the door drop their 20, 25 bucks. And then I also write, so if I were to sell an article to a magazine, that might be part of the monthly earning. There is, of course, the music and the merch, which is trickier as you’d imagine, because Spotify has everything for free, so why would people pay for music? 

Menendez: Right. 

Dessa: Right, so you make the music into an art object. You do some cool design features. You sign it in metallic marker and make an event of the object, itself. So, some of it’s, yeah, merch sales. And then I would say I get enough money from Spotify every month to pay 80% of my phone bill, so there’s a trickle there, but not much, so it’s all these things kind of combined that help get it done. 

Menendez: You said to Juleyka, our executive producer, “We’re really a t-shirt company masquerading as a record company.” 

Dessa: I did! So, I just came back from tour. I saw Juleyka just a few days ago. And because the music is free, you do learn how to sell a lot of other stuff at the merch booth, you know? So, over the course of my touring history, I’ve sold t-shirts, tank tops, windbreakers, all those normal soft goods, but also hats, engraved flasks, a bronzed version of a neuroanatomical feature in my own brain, which I had 3-D printed. So, you do get creative. The merch game is key, is clutch. 

Menendez: How do you describe your music?

Dessa: Man, whenever possible I try to avoid doing it, and I just hand somebody… If I can just hand somebody headphones and press play, they’ll know if they’re gonna like it. You know what I mean? There’s not a lot of pitching music you can do. You like it or you don’t. But I will say that it’s word driven. I think I’m a writer and a lyricist probably first. It is usually some combination of anger and beauty, and I, I think for my whole life, will be driven by the themes of connection, communion and loss. 

Menendez: Your mom has said that your music is always so sad. 

Dessa: Yeah, I had finished one record, and I sent her the early mixes, and she said, “It’s beautiful, but yeah, why is it always so sad? You always make music to bleed out to.” I thought, “Why do you know that expression?” 

Menendez: Yeah, how’d you learn that expression, mom? 

Dessa: What moms are you hanging out with? Yeah. But that’s my favorite genre of music. 

Menendez: Mine too.

Dessa: Why do you like it?

Menendez: I think because during those formative years, like the 12, 13, 14, where I think with a few exceptions, you feel sort of alone in the world, and feel that the way you see the world is the way only you see it, there were artists at the time who made me feel less that way, and made me feel like they were in adulthood and sort of had made it into adulthood having lived all of these emotions and all of these feelings, and had come out whole. 

Dessa: Who did you listen to?

Menendez: Tori Amos. 

Dessa: Yep. 

Menendez: Ani DiFranco.

Dessa: Yep.

Menendez: But again, my parents were like, “What is up with this sad music?”

Dessa: Totally. Are you okay? 

Menendez: Are you okay? And you’re like… Yeah, in some ways it can be sad, but it can be really empowering, so I think of a song like Velodrome, and I think you can hear sad, but I think you can hear inspiration in that. That, to me, is like I think when I was 13, that was the type of song that I’d be like, “One day, I’m gonna live in New York City and walk busily down the streets and have this life that is complete, and whole, and things will whip around.” It just… It is so, to me, open to interpretation. 

Dessa: And you just moved to New York from Miami.

Menendez: Yeah. 

Dessa: Do you feel like that’s you now? 

Menendez: Yes.

Dessa: Like I am a person fast walking through New York with a cool place to be.

Menendez: Yes.

Dessa: That’s so cool. 

Menendez: Yes, and listening to the music of a person I’m gonna sit down to and get to ask questions. Yes. It’s amazing. My 12-year-old self would be both underwhelmed and totally pumped. 

Dessa: Totally! Okay, so why would she be underwhelmed?

Menendez: In some ways, my life is so much more domestic than I think my 12-year-old self… I mean, I’m married and I have two children. Right? Like my 12-year-old self would have been like, “You’re a mom? Oh, that’s not cool.” 

Dessa: Did your 12-year-old self not think she was gonna become a mom? 

Menendez: Probably deep down, but not… That wasn’t the ambition. 

Dessa: Okay.

Menendez: Would your 12-year-old self be impressed with this?

Dessa: Both. I think she’d be both. I mean, it depends what moment she cut in on, you know? 

Menendez: Right. Totally.

Dessa: Right. I mean, the stage moments, I think she’d be like, “Awesome!” 

Menendez: We did it. 

Dessa: I think for some of the other moments, that kind of brand of sustained indignation and disappointment in human culture that you have when you’re 14, I think that’s right. I think she was right, and I think I got tired. I think that when you are first freshly introduced to the adult world, the fact that you recoil is rational. And I think we just get used to it. 

Menendez: How does your mom being Puerto Rican show up in your life?

Dessa: Oh, I think it’s really changed over the years. When I was a kid, I don’t know, the things that I perceived about my mom, that I associated with her Puerto Ricanness, was the way she danced, and that was important to her. Movement was important to her, and it was really important to her that her children have rhythm, and so she… My dad once came home and she found… He found her forcibly clapping my hands, but in a really upset and upsetting way, because she was so afraid that if I grew up there, I wouldn’t have any rhythm. 

Menendez: And so, I have to admit. I haven’t seen you dance. Did you get the rhythm? 

Dessa: I’m okay. I made it. Yeah. I made it out. I made it through. The way that she sometimes would cook, she’s a very good cook. And then the way she looked, like I am white looking or white passing, for sure, and my mom is a something, like if I were a marketer, I’d call her a soft ethnic or something. You know, she has kind of ringlets that if, when she cuts her hair short, make an afro, and I think it was something that I gravitated to. I liked it. I wanted to be more like that. I felt a little bummed that my mom looked Puerto Rican, and had a name that can be said in an Anglicized way or in a Latin way, in a Spanish way. So, it’s Sylvia or Sylvia, and the same is true of all her cousins. It’s Irene or Irène, so they all have these kind of nicely convertible names. 

Menendez: So, no one calls you Dèssa? 

Dessa: Nobody. Yeah, except for me, like when I’m drunk and speaking Spanish, which is just humiliating, because it sounds so stupid. But it was something that I wanted more of, and then I think when I started rapping, and people would ask like, “Well, what’s it like to be a white rapper?” I felt like there was a card that I could play, sort of like, “Oh, you haven’t done your homework.” 

But now when people ask that, I’m like first of all, you haven’t done your homework. But second, that’s a question I should answer, and take seriously, because I maneuver through the white world. 

Menendez: What’s the answer?

Dessa: Oh, it’s a long one. I mean, and one that I’m still answering, but I do think that some of the money that I make, and some of the gigs that I get are because I went to college with somebody. It’s like I’m the beneficiary of all of these network connections that I might not be the beneficiary of, right, if I’d grown up in a totally different neighborhood, with a different set of parents, and ended up in a different public school, and then ended up in a different public college. Right? My whole network would be different, so when you fast forward 15 years, maybe you don’t have those connections that can get you paid, and can get you ahead professionally.

I think like a lot of people, you sort of struggle in your own head to try to understand your own life as the product of both luck, skill, and error, and it’s really hard to tell how exactly all three of those variables ought be weighted. But I think in the past few years, a lot of us have been asked to consider the luck of our birth, and that’s appropriate. 

Alicia I recently re-watched your TED Talk, “Can We Choose to Fall Out of Love?” Is it asking too much to ask you to take me back to the relationship that inspired that breakup? 

Dessa: Sure, so I joined Doomtree I think… In my early twenties, like 21 or 22. Nobody was really counting, but I fell in love with one of the members, and he fell in love with me, and this I think was before I was even in the crew. We were dating, and that relationship was big, and intense, and felt a little bit charmed in some ways, that like we got to be on stage together. It’s a big deal. A lot of adrenaline, a lot of love and drama, to be able to pile in a van with all your good friends, all of them dudes. It was like a very intense life. 

I wanted to love this dude. As our relationship went sour, I was also pretty mad at that dude. There was also a show to go on that night, and it was not appropriate to bring my sour feelings into the minivan where the collective art and livelihood of all these people lived. 

Menendez: There’s something that struck me though that you said, which is that you were sort of embarrassed about the fact that it was taking you, it was so hard for you to bounce back from this. 

Dessa: So, as those feelings continue for five years, and then seven years, and then for a while he and I both dated other people, and I think had a pretty good thing going with our partners, but those relationships dissolved, and we ended up trying again. So, over the course of the thing, it’s something like 13 years, or 17 years. It’s just so, so long. So long that it was like, “How am I still so busted?” Yeah, that was embarrassing. It didn’t feel like an empowered feminist way to be, to have your quality of life seriously informed by your feelings for a dude. 

Menendez: And so, you turned to science?

Dessa: So, after trying all the normal ways first, you know what I mean? It was like you talk to your friends, you drink too much, and then you don’t drink at all, and then I ended up moving to New York, at least part time. 

Menendez: Take up Kundalini yoga. 

Dessa: Yeah! You get weird. You do weird stuff. Yeah. That was then when I had been watching like a TED Talk on my laptop, and there was this woman, Dr. Helen Fisher, who was presenting work that she’d done where she had tried to find the locations in the human brain, the exact neuroanatomy that was associated with romantic love. I found that surprising, because I didn’t know there was gonna be particular neuroanatomy that was associated with romantic love. That had just never occurred to me, that that might… I don’t know. There might be a locus for that feeling, you know? 

And then I thought, “Okay, well, if she’s found out where it is, then if I found my love in my brain, maybe I could remove it and stop hurting so much.” So, that was what I tried to do.

Menendez: Did it work? 

Dessa: Medium. Sort of. I would say it sort of worked, yeah. 

Menendez: You got merch out of it in the process. 

Dessa: Oh, man, and the merch is so tight. It did make me feel better. It didn’t solve every problem, but yeah, it did make me feel better. I felt more solid. I still feel pain, but I felt… I was feeling really compulsed. I mean, I was feeling spun out about the dude. Just like the force of my love was outlandish to me, and it was making me so sad. So sad that even though I built this pretty cool life, I was having a really hard time enjoying it, because I wanted that to work so bad, and I felt so immediately the pain of it not working. 

Menendez: You introduced me to a term that I had… I didn’t know the term torch song. 

Dessa: Yeah. Yeah, yeah. I think it’s an old term, from like the sixties. It’s like… Maybe it’s something that’s sung both female and male singers, but it’s usually like it’s an old flame that you’re stuck on. You’re holding a torch for somebody. 

Menendez: And meanwhile I’m on the Google being like, “Is this short for torture?” 

Dessa: Yes.

Menendez: Because that sort of became your thing.

Dessa: Yeah, exactly, so I would contribute to songs about all sorts of stuff, but in my solo work, a good chunk of them were like these kind of spirited, sad, sometimes angry, like… just feeling totally broken by this feeling, and housing all of this totally useless love. This love is good for nothing. It doesn’t help me, it doesn’t help him, no one is helped by this. 

Menendez: In another interview you said something that I relate to so deeply, which is, “I’m a kind of perfectionist sort, who’s always sort of bummed about how the last thing went.” 

Dessa: Yeah. That doesn’t sound that articulate, I have to say.

Menendez: No, it doesn’t. Especially in contrast to the person I’m sitting here with, but let’s go to the essence of it, which is being a perfectionist.

Dessa: Yeah.

Menendez: Can you do what you do at the level you do it without being that person?

Dessa: Ah, man. I’ve been thinking about this a lot today. I don’t know. The story that I’ve told myself is this approach and these ideas, and this degree of hyper-criticalness, is going to make you a bit unhappy. But it is also going to make your work a lot better. If 98% was good enough, then you’d stop there, but I find that to my disappointment, the kind of… That hypercritical approach is very difficult to confine to yourself. 

I’m critical of everything, you know? And that’s not… I was thinking today, is it possible to be uncompromisingly critical and also warm, tender, generous, forgiving? I think there is a natural tension between those things. 

Menendez: Yeah, and especially, I mean, my perception of you not knowing you at all is that you really have access to both. 

Dessa: Trying, but I do think… I don’t know, just I think that that kind of criticality, it can make you short with other people, as well. You know?

Menendez: Yes. No, I know for sure. I used to sort of use as a shield saying, “Well, I know I’m really hard on you, but I’m really hard on myself.” As though that somehow that makes sense-

Dessa: Like that makes it better for them. Oh good, you yell at you after you yell at me? Great. Let’s have a birthday party. Yeah. 

Menendez: But when you hold yourself to a high standard, you do hold other people to a high standard, and I think there’s just sort of a question of how you both enable and empower other people to achieve excellence, without that crossing over into the type of critique that is hurtful and paralyzing. 

Dessa: Also, what if people don’t want excellence like I want excellence? How are you going to treat those people?

Menendez: I think that has been an evolution for me professionally, which is that I can only be surrounded by people who want the same level of excellence.

Dessa: I feel you, but what about the relationships that are not professional? 

Menendez: Oh, that is a whole different-

Dessa: You know what I mean? I just even mean like in a partner, like the fact that I’m like, “I just want you to know that I’m also hard on me,” is not… That is not a consolation, really. Yeah, so the fact that I make weird rules, and for myself, I don’t know. I’m concerned about how that might play out in the rest of my interpersonal relationship. 

Menendez: I have found a way to make it work.

Dessa: How? 

Menendez: I think part of it is finding someone who approximates, has sort of either the same level of self awareness, or the same level of sort of holding themselves to an impossible standard, so at least there is some empathy in there. But then also, really sort of radically coming to terms with the fact that a person is who they are and they’re not a project. Like that was a thing that I used to do, being like, “If I could just tidy this thing up on the margins, then this could be perfect.” 

It’s like, “No. No. This is what it is.” And so, you either have to fully embrace that, the messy parts of it too-

Dessa: But do you do that with yourself?

Menendez: I’ve become a lot more forgiving with myself, I will say. I think also parenthood has forced me to do that in the way that it’s like there’s just less time and space to be in my own head, [crosstalk] with the gifts of children-

Dessa: Yeah, totally. 

Menendez: … which is they really draw you out, and that every day sort of starts fresh. There is not the time and energy to have that mental hangover from the day before. 

Dessa: Yeah, so I’m just gonna have a kid. 

Menendez: You’re gonna find the right person. 

Dessa: Yeah, probably. Probably. 

Menendez: Because it’s okay to be uncompromising, right?

Dessa: I think so. I think so. I mean, I do think that as I grow older, it is also possible that some behaviors that serve me really well in my twenties and thirties, I’m gonna decide when I leave my thirties, “This one isn’t serving me well any more.” 

Menendez: Last question. I would posit that there are a lot of people who want to live the type of life that you are living, in the sense of having lots of interests, having lots of projects, not confining themselves to one thing, but they don’t know where to begin to do that. How about just someone who wants to buck convention?

Dessa: Yeah. Yeah, I’m with this. I think even little bucks go a good, long way towards long-term bucks, like cutting your own hair, getting the weird bicycle, like I really mean it. Eating weird food. I think buying one weird thing at the grocery store, just things that you can do to nudge yourself off of your own monorail tracks. I think that’s good. 

I mean, you can always bail and go back to the way that it was, you know? You can always bail. That said, I think failing sucks. I think… I am very sensitive to public embarrassment. I hate it. I don’t think it’s always curative. I think sometimes it just sucks. I just think that it’s better than the alternative, which is wondering what it would have been like if you had tried to have a fuller life. 

Menendez: Dessa, thank you so much. 

Dessa: Thanks for having me. For real, thanks. 

Menendez: Thanks as always for joining us. Latina to Latina is executive produced and owned by Juleyka Lantigua-Williams and me. Maria Murriel is our producer. Carolina Rodriguez is our sound engineer. Emma Forbes is our assistant producer. We love hearing from you, so email us at, and remember to subscribe or follow us on RadioPublic, Apple Podcasts, Google Podcasts, Pandora, Spotify, or wherever you’re listening, and please leave a review. It’s one of the quickest ways to help us grow as a community. 


Menendez, Alicia, host. “Why Dessa Is So Much More Than an Indie Rapper.” Latina to Latina, Lantigua Williams & Co., January 12, 2020.