Jesse Boykins III is a Jamaican-American, Grammy-nominated singer, songwriter, producer, and creative director who has released 5+ records independently and via Def Jam records, collaborated with Steve Lacy, Charlie Puth, Theophilus London, Calvin Harris, and others. We talk at length about advocating for yourself and your creative vision, knowing the tools you have in your toolbox and using the right one at the right time, honoring the mission of the project, saying yes to collaboration to lift others art, simplifying everything, and more.
Jesse Boykins III is a Jamaican-American, Grammy-nominated singer, songwriter, producer, and creative director who has released 5+ records independently and via Def Jam records, collaborated with Steve Lacy, Charlie Puth, Theophilus London, Calvin Harris, and others. We talk at length about advocating for yourself and your creative vision, knowing the tools you have in your toolbox and using the right one at the right time, honoring the mission of the project, saying yes to collaboration to lift others art, simplifying everything, and more.
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All music written, performed, and produced by Aaron Shafer-Haiss.
hey, and welcome to this week's episode of the Other 22 Hours podcast. I'm your host, Aaron Shafer-Haiss.
[00:00:12] Michaela: And I'm your host, Michaela Anne. And this is our second year of the podcast. We're so happy to still be here and thankful that you're here with us.
[00:00:20] Aaron: Yeah, because honestly, we wouldn't have a show without you guys. And so, with that, we have a few simple asks before we jump into today's episode. There is absolutely no money in streaming podcasts. in light of interrupting our conversations, trying to sell you a Casper mattress or maybe some kind of powder to drink in the morning Although
[00:00:39] Michaela: I would like to do that if anyone's out there listening.
[00:00:43] Aaron: To keep us from doing that, we have started a Patreon, and over there, you get a bunch of goodies, you get some behind the scenes things, you get inside access, it's a building just like this show builds and develops over time. We're offering all of that for pretty much one price of less than a boutique coffee every month.
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And maybe we as creatives can all figure out how to navigate this business together a little more healthily.
[00:01:32] Michaela: And one of the things we really pride ourselves on with this podcast is that we are not music journalists. We are musicians ourselves. So instead of thinking of these as interviews, we think of them as conversations that we're having with friends, acquaintances, new friends, about just the honest reality of what it is to build a lifelong career around our art,
[00:01:52] Aaron: which is a crazy thing to do.
that's mostly because a lot of it is outside of our control. And so we'd like to keep these conversations focused on what is within our control, being our mindsets, our habits, our routines, creativity in general. And that has slowly over time. Distilled down to the question, what do you do to create sustainability in your life so that you can sustain your creativity?
And today is another episode with a really old friend. Some of McHale and I went to college with at the jazz school, which came to light today. None of us really thought we would be studying jazz, but there we were. And today's guest and conversation is with Jesse Boykins, the third.
[00:02:28] Michaela: And Jesse has had a really incredible diverse career is Grammy nominated songwriter, musician, producer, manager.
Visual art is a big part of his work as well. Video direction. He shares so much insight about doing. So much different stuff. He's collaborated with Vic Mensa, Charlie Puth, Calvin Harris, Theophilus Linden, just to name a few but more than all of that and what I was so excited about inviting Jesse on this because I had a feeling he was the same as the kid that I knew almost 20 years ago He just has such a beautiful, generous spirit that's really community minded.
And as we find out little did I know that we all felt like outcasts in a certain way, which is such a interesting thing to think about how it still translates to the larger music world. How so many of us feel out of place, but go around not letting each other know that.
[00:03:25] Aaron: If you haven't been to jazz school, it is A unique environment full of positives as well as some long term negatives Which you know the movie whiplash everybody knows about but there's a we kind of touch on that a little bit but you know, we checked a lot of boxes that I really love which is, having a vision and having Mission statement in a way a manifesto jessie says but staying open above that learning through adversity Being curious wanting to be challenged You It's just like top to bottom full of so much.
You're going to hear Mikayla and I go, Oh, like quite often in this episode. And
[00:03:59] Michaela: prioritizing creative freedom over all else, over outside validation, supposed number growth, all that stuff, always coming back to how do you feel the most creatively free.
[00:04:12] Aaron: Yeah, it touches on, we touch on creativity. We touch on mindset.
We touch on business. This is one of those all encompassing conversations. So without further ado, here's our conversation with Jesse Boykins, the third.
it has been years. It's good to see your face.
[00:04:26] Jesse: Good to see both of you guys's face. How you guys doing?
[00:04:29] Michaela: We're good. It's probably been, oh my god, 15 years since we've seen you.
[00:04:34] Jesse: Maybe longer, but yeah,
yeah,
[00:04:36] Michaela: Thank you for being willing to do this.
[00:04:38] Jesse: I was going to say, I watched a couple of you guys's interviews and I really liked, it and I miss you guys and I like this, so I'm happy to be here. I'm good. I'm in good spirits. It's very early here, so
[00:04:48] Michaela: are you?
[00:04:49] Jesse: I'm in Los Angeles.
[00:04:50] Michaela: Okay, that's that's what I thought when she said it's at
[00:04:52] Aaron: 10 AM. I'm like, wow, he's up You know,
[00:04:55] Jesse: usually awake and I'm usually awake. She's right. I'm awake at six usually. So This is regular.
[00:05:00] Aaron: What do your mornings look like? If you're getting up at six, do you have a routine that you do?
[00:05:04] Jesse: my therapist slash life coach has been telling me to get a morning routine. It varies depending on uh, what I have to do, but most times I'm up about what I'm going to do. don't usually write a lot of things down. So I try to see what I have to do naturally, like innately what my body tells me to do.
I'm like, Oh, what are the plans? Oh yeah, true. I got to water the plants. Feed the turtle. Okay. my turtle. All right, cool. Go to the gym. Gotta go to the gym got a meeting at 10 o'clock. Okay, cool. I got a meeting at 10 o'clock, so it's like
[00:05:33] Aaron: Mhm.
[00:05:35] Jesse: I try to like just envision my day.
[00:05:37] Aaron: I get up around six too, but that's cause we have a kid. And if I don't get up at six, then it's like, I'm responsible for another human being, like the second I opened my eyes. So if I get up at six, I can like, remember that on my own.
[00:05:48] Jesse: Yeah.
[00:05:49] Aaron: I have to dive into that,
[00:05:50] Michaela: which I don't do that I can manage it very occasionally.
I like wake up and put on a meditation, on my phone and just lay in bed and listen to it. And then starts the onslaught of almost three year old life but it's definitely like, oh yeah, it would be good to wake up and be reminded I'm my own person and not just this gopher for a little child.
[00:06:15] Jesse: doing things always been beneficial for me, especially if I could picture me doing it in a good light, like just happy. was happy when I envisioned me watering a plant, so I better not be talking to them on me. You know, like, So it's like it's a mindset thing.
Yeah.
[00:06:33] Aaron: to kind of get everything in line.
It works better. For me, if I write stuff down, that just works for my process a little bit more. But it definitely makes a difference, rare occasion that I'm on the road these days and not waking up with the kid, I noticed if I like get up and have to get to my tasks and obligations, right off the bat.
I'm kind of
Just like playing catch up all day and just feeling scrambled.
[00:06:55] Jesse: Understood.
[00:06:56] Michaela: So jumping right in, you mentioned a therapist life coach. How long have you been working with someone like that and what was the catalyst for seeking that out? If you feel comfortable sharing.
[00:07:07] Jesse: no, it's fine. We can talk about it. It's fine. I've had two now. So this is my second one and been with her for about a year now. a relationship that I was in actually started it. She said uh, We can't be in a relationship if you don't have guidance. So I Guess this ultimatum is positive. So I'm going to receive this information and do my due diligence to do some research on it. And I found one that a good friend of mine, one of my best friends recommended me because I wanted to find someone who could talk to like hyper creatives, in the entertainment industry. Because I have to deal with so many different types of people all the time. she's been very pivotal currently. A lot of, things that I'm focused on how to treat myself through a lot of the situations and honor, everyone involved and currently we've been speaking about being more objective than subjective. good practice, in regards to where I want to go in my life and what I want to accomplish. it's beneficial. And, I try my best to apply the things, which sometimes is hard when you're stuck in habits. You get habits, and I'm 39 now, so. in order to break these habits, I try my best to accountable and apply the things we talk about, and most of the time I already know, she's just like reassuring me of something that I've already, I'm already keen to, I just, she's just like, now you're going to do it, she's like a accountability fairy godmother,
Yes.
that's what she is, Yeah. That
[00:08:25] Michaela: stuff is so hard we were just talking about this morning. Like I feel like my cycle is like, rock bottom. I'm like, I'm in rock bottom. I got to make some changes. And then I'm like, okay, here's all these new habits I'm going to instill.
And then I'm good for like a week or two. then I start slipping and I'm like, I feel really good. I could like not go on a run. I could not meditate. I could maybe scroll Instagram for an hour. And then all of a sudden I start sinking and seeking. and then all of a sudden I'm like, Oh, I'm back at rock bottom.
I got to go back and make changes where Aaron he's a Virgo and he's super like, All or nothing. Very much so. So he's like, I'm going to make these changes in my life.
And he like sticks with them to a point where sometimes I'm like, dude, can you chill? And
like.
[00:09:09] Aaron: yeah, I go the opposite way.
[00:09:11] Michaela: But it's really beneficial in a lot of ways. if you know your personality needs that helpful accountability, having someone like a coach or a therapist, that's not your problem. partner cause that's so weighted when a partner's like, should you maybe go on a run today?
Cause it might help you like, it's really helpful. just to give our listeners some backstory we all went to college together at the new school in New York city in jazz. my memory of you, Jesse, is that like you had so much energy, you had so much creative energy that you were, from my perspective, I was very much like, I didn't know what I was doing.
ended up at a jazz school. I was very like closeted country folk musician. And I remember you and Chris Turner always being like very encouraging of that. I remember one time you listened to something that Justin Matthews and I had made and you like said something nice about it and I was like, Yeah, but it's kind of folk music.
And you were like, Yeah, no, Michaela. It's nice. Like, Even Chris, we're always just like, yeah, make the music you want to make. so from my perspective, especially being really shy and not figuring out what my path was yet. Like, seemed someone who knew what you wanted to do, and were just overflowing with creative energy, and putting out music, and playing shows all the time.
I'm curious how that has progressed in the past, man, almost 20 years now come to think of it, have you been able to just naturally sustain that enthusiasm Because you've gone on to do a lot of great stuff.
You've put out records with Def Jam. You've done a ton of great collaborations. You've got a Grammy nomination. from the outside looking in, you've achieved great success, but we all know that it looks very different on the inside. So what has that kind of overall journey been like for you? Have you been able to maintain that pure enthusiasm or if you had to work to, cultivate it and regain it at different times,
[00:11:04] Jesse: I do remember telling you that. That's so funny that you remember
[00:11:07] Michaela: it was pretty poignant because I, I felt so out of my element at the jazz school of just I don't know what I'm doing.
[00:11:14] Aaron: I will say you, bring that up. Semi-frequently.
I, Yeah. Like once a year. You're like, Jesse once said like, just make the music. You wanna make
[00:11:24] Jesse: felt out of place too, so I connected with you, I didn't study jazz. I got accepted into the Grammy Jazz Ensemble then someone was like, you should go to jazz school. And I was like, but I don't know anybody. I don't know anything about jazz, so. it was a real eye opener for me and, I had to stay confident in the things that I wanted to create at that time because, it was a very um, polarizing environment as far as everybody being like a jazz head and, shredding and all this stuff
yeah, I'm very much still the same as far as what you're saying, like in support of people expressing themselves with their art form and the things that they've been gifted. Yeah, I think, creativity has definitely kept me sane as far as just my approach and, the celebration of it, I was stuck in my Def Jam deal and they wouldn't let me out,
For a couple months, maybe like a year.
And then stuck in my publishing deal and I had to get out of that deal as well, right after that. that moment in time set me back on the music side of things, but it, opened up my passion for the other expressions I was already doing, kind of like creative direct and, you know, I was always making videos with my friends.
So now we're a little bit more, focused on that. cause at the time I was saying no to, Everything Def Jam was putting in front of me or just anything music related for about three years My personal work and then what I would do is I would just collaborate with who wanted to work with me, That helped me be open to creating new spaces and with new people and for them, not for myself.
I think that kind of opened up a part of my brain that had always already naturally been there, because that's what I was doing at New School. So I was recording Kenneth Whale, I'm in the, eighth floor, and Saunders, and we was, writing everybody's songs, and kind of grew up in that system.
You know, came from chorus and gospel choir and I was in a singing group in high school. We almost got a deal before I went to college. So I was always wanting to be a part of or developing something with a group of people, lot of my music represents that for me. A lot of my albums, I collaborate with a lot of my close friends, a lot of people I love and I admire.
And so that's never left. Actually, it's even more now. Because now I get to executive produce people's albums. So I get to create these spaces for people that I wasn't given the opportunity to create all the time. I'm just more about that honoring whatever the mission is.
And I think that's the main important thing. what is the intention of what we're doing while we're doing it? down to like, let's write a manifesto. So When everybody else comes to collaborate with us, they'll read the manifesto first before they get in the room. So they know what, that we mean business, we're not just shooting things at the wall, you know, we actually understand the direction we want to go in and we want everybody to like add to the vehicle so we can go faster, That's kind of how I look at a lot of things and, things that I'm developing outside of music, I look at it the same way. Like, all right, what's the best group of people I could cast for this web series I'm writing? if I write a manifesto for the web series, who am I giving to first?
So they can champion it to everybody else. And, I try to get the best out of not that much. So, try to be as resourceful as possible and intentional. learned a lot of that going to school too, and just being around jazz musicians specifically, very intentional human beings, when it comes down to one thing, practicing, you know,
[00:14:26] Aaron: Scene. Yeah.
[00:14:28] Jesse: You know, and so to this day, I have this, called, I tell myself every time I get down on myself or I feel doubt or anything, I say, everything's practice. Everything's motivation. that's like jazz. Everything's practice, everything's motivation, you know?
So, I use it a lot, lot of people I work with, that's one of the things I tell them, cause as an artist, it's really hard to find sustainability in confidence, just being happy about something you make continuously and then feel good about it. It's very hard to like, you know? maintain that when you, you have outer things like, Oh, I didn't do that good on Spotify. this person didn't post about it. So is it good? Like, I used to sell CDs on the street and top square.
I didn't care if you liked it or not.
Thank you for the money.
[00:15:07] Michaela: our neighbors are Cuban and Honduran and they have like epic parties next door. They roasted a pig, they're like blasting salsa music, they're having so much fun, they're so sweet.
And I was sitting in our backyard, listening and I was like dancing with next door and I was like, man, this feels like Brooklyn days like Aaron was heavily involved in the Brazilian music scene. And like, this feels like the parties we would go to in Crown Heights with our, Brazilian friends.
And since living in Nashville, and being in kind of like the country Americana folk world it's just. Not that so it started me down this path of nostalgia in my brain and then getting prepared to talk to you. I was thinking about all of the shows that you put on.
I went to so many Jesse Boykin shows you passed out flyers that you like printed. We didn't have Instagram back then our brains are different. Nobody was like how many followers does Jesse have and what kind of shows it is like you literally just passed out Papers it was so community Feelings like a bunch of friends would come and you were so interactive and it just feels like how do we keep that in today's world?
[00:16:12] Jesse: I don't think it's about things being kept, people always ask me all the time like, do you miss Brooklyn? Or, you miss those shows? You know, I recently worked with an artist and he was like, man, I used to be at all your Brooklyn First Museum shows at the Brooklyn Museum at the first Saturdays.
I'm like, you used to go to those? He's like, yeah, when I was like 16. I was like, wait, what? I mean, like He was the king of Brooklyn. I was like, I was active, I do appreciate those moments, they speak to like everything that I create and I create, even the part where you saying like giving out flyers and stuff like I still texting people one at a time, like for my for my album listening party last year, I had an art gallery.
Like I literally, people was like, I'll blast it on the internet. I was like, nah, I'm cool. And I just sent it to the people that I felt would appreciate it the most that's what I care more about. I'm not really like, oh man, like we got 75, 000 followers on Instagram.
I need like 2 million. Like, I don't think like that, I'm just like. Did I make something that could impact people? even if they never meet me, even if they never know who I am, even if they never follow me. Yeah, I did.
[00:17:12] Aaron: Especially when you're talking about like followers, the one thing I like to bring up all the time. A friend had said it to me in passing. She's like, it only takes a thousand fans in the entire world that spend 100 on your art in a year.
And you're making six figures. That's all it takes.
[00:17:25] Jesse: I look At life the same way, cause I was independent for so long, then I toured the world and I've been all these places and be like, man, how did you get to Latvia? I don't know. I wasn't trying to go to Latvia. They was like, but yeah, you been. I was like, yeah, I made this music and this guy DJ from BBC radio played it on the radio in Europe.
And then I was in Latvia. I don't know nobody from Latvia. so I don't owe Latvia anything. Latvia doesn't owe me anything. And that's how I look at people. how did you hear my music? I'm not concerned with how I'm just glad you did If you want to share it cool, if you didn't cool because I didn't know you existed before And you didn't know I existed before maybe you just heard of this new music and never heard of me before and I'm appreciate that interaction and What I'm capable to do with something that I just making a small room with my friends.
So I just acknowledge its power do my best to communicate that with people around me, because I do want to progress I want to continue to experience my version of success, whatever it may be. I want to also be able to create opportunity.
So I have to be open and grateful and.
Thinking in the littlest places I can, you know, just drop the little seasonings when I can sneak it in there and then Hopefully it'll create impact. A lot of the artists I work with, The bigger name artists I work with is based on music.
I made I didn't know them. I didn't meet them randomly at a party or anything like that. I don't really go off that much So they like I heard this album one of my friends were playing. I just want to meet you I'm like, all right, cool. I would like to meet you
So if I'm impacting those type of people, then I'm, good.
[00:18:52] Aaron: the two sides of the coin of making these manifestos, these mission statements, so you can really kind of outline a vision and where you're headed, but then also staying open on that path, because I think it's a double edged sword where you can, make these manifestos and. have this vision, but then it's so easy to get closed off in that you know, kind of have blinders on, where it's like, you need to be on that path, but also keep your peripheral open to be like, Oh, because success might not show up in the way that you had thought of 10 years ago.
There might be this little door over here that's like, somebody's like, come to Latvia and you're like, man, what's in Latvia, nothing's going to be there for me, but who knows? You don't know until you try and things can snowball from there.
[00:19:29] Jesse: exactly. Literally what you're saying. they call me like a five percenter. You know, they say, Oh, you think right brain, left brain all the time. The other day someone was like, Oh man, you're an artist. You're supposed to have your head in the clouds.
I'm like, nah, the clouds are down here with me.
love that. Yeah. I'm with the cloud. They just down here with me, you know, As much as possible just based on the fact that just being a professional, and like you said being open but having some direction. I think it's important. any other way of being actually with getting things finished. I was referenced this movie, The Accountants. I don't know if you guys ever seen it with Ben Affleck basically, I don't know.
basically, it's about this guy who's like on the spectrum and he, they take his equation away from him. He's like people's taxes and he's like figuring out all this hidden money and then they like, oh, somebody died.
So we're just going to erase everything you worked on. He's like, no, I don't think you get it. I got finished. That's me. I have to finish things, but I also have to discover. So it's like to say in double edged sword.
It's like, yeah, I want to find something new, but I also want to finish what I, found before like, you know, I tell all the homies, I'm like, I want to be in a flow state all the time as much as I can, don't want to be too overwhelmed.
Just want to be in the middle try to sustain a little vibe, I'm like, oh, that's cool Yeah, bring that over here. Oh put that right here. Oh, it worked perfect. Ah, like I just want to do that those are my best days
[00:20:37] Aaron: Are there things that you've found that work for you to stay in that state, time, do you kind of have a structure to your like, man, I got a business stuff I need to take care that's separate then from the
[00:20:47] Jesse: for sure I take all my meetings and everything up until about noon one o'clock and then Don't holler at me about no work stuff after that.
if it's not an emergency, I'm just making a pitch deck or researching photos or, you know, I'm writing scripts, I have to get it out.
So I give myself a break. Up until a certain time as far as work is concerned because I consult I used to manage artists for a long time, I'm on a lot of calls, like I don't know what the best way to release music. Let me just interview and say, I want to talk to these people and let's just talk to all these people and see.
If I could have a Eureka moment with someone, their new way of distributing music is the best way and take in the information the first half of the day and then I find some ways to get it off me as far as creating something that's
[00:21:29] Michaela: hmm.
Can you talk a little bit about, because you said you were stuck in your Def Jam deal and then you were stuck in your publishing deal. And I think for some of us, getting a deal was always the goal you wanted the financial support, the resources, the belief that they'd be able to get you or your music out in a way that you couldn't on your own.
[00:21:46] Aaron: And the validation.
[00:21:47] Michaela: And the validation and, and I've been in indie deals for the last 10 years my mindset has been really shifting I've felt super stifled for a number of reasons, but it stopped me from putting things out as I wanted to because of just the layers of stuff you have to go through when you're working with a company and multiple people and the delay and, but then wanting to walk away from that has also been scary because it's like I have to find the financial resources on my own if I'm completely independent.
And also who's then validating me to the industry to say, Yeah, we stamped her. She's good if I'm without anything. So these are all the things I've been going through in my mindset. So if you could share a little bit about your experience of having those deals and then going through and ultimately coming to a place of why you wanted to leave them.
[00:22:38] Jesse: being independent, for a long time, I learned a lot of things, and I learned about all the things I didn't know that I thought I knew you know, it's trial and error. So, within that time, I didn't have proper guidance I just want to make music, get on stage, tour.
do some shows, see the world, eat some food. I never try. And then once I got over that part, I was like, all right I've been to damn near every place I could be. I've been to Russia, I've been every South Africa, like Italy. I'm like, all right, I've been everywhere. I could be, you know, just off playing shows and stuff, but I'm still not, you know, in a, financial situation where I feel confident that I'm gonna be okay, moving forward.
So I, I had to be a little bit more responsible. So, Ultimately I moved to Los Angeles. And Los Angeles taught me a lot, in New York, I didn't get to see anybody's uh, houses or, you know, we, we met up at the park or, you know, we didn't go to each other's houses like that. It was everybody's outside, you know, I'm in LA Miguel was like, yo, come to my video shoot.
I'm like, all right, cool. And I come to the video shoot. I'm like, yo, you got three trailers? He's like, yeah. I'm like, Oh, you got three trailers? He's like, Oh, one's for his clothes. And then one's just for developing like production people. And then, okay, you got like a tent outside for like the cats and stuff.
He's like, yeah. And I was like, you got a director. okay. Because I was doing that. I know there was like a person for that. So like Mm-Hmm. who's styling you? oh, I got two stylists. You got two different people bringing your clothes. Oh, did all the styling. I styled everything. I didn't know.
And no diss to him because he's a brilliant human. You know what I mean? . But just I appreciated him letting me in in that way. And he has no idea about this because we've never talked about it. When we talk, we just talk about music. But him opening my eyes to that. I was like, Oh, wow, this seems cool.
I like this. I think I'm not sure, you know? and so that was the same when it came down to getting a deal. It's like, I'm getting compared to all these people that I'm friends with that are highly successful people. triple on triple platinum, and I'm like, I'm filling in the blank here. I got everything they got. I'm only missing that one thing, I think, right? Yeah, so I go and do my Def Jam deal and everybody who signs me, i. e. the CEO and the head of marketing, who would approve all the budgets for me to make the things I want to make, both leave two months after I sign my deal.
Oh. Mhm.
this is just me and the A& R who signed me. tells me they're not opening up the budget for my LP too. Yeah. Like in my contract, because a new guy came in, doesn't know if he wants to keep me. like, oh, I'm not, one to be kept, or you don't know if you want to keep me.
I don't like the language of that. so I'm gonna go ahead and just tell y'all let me get up outta here. the thing with the deal is if, I leave they have to pay me out, give me some money We don't know if we want to give you some money We don't know yet And I'm like nah, I'm not here to wait on you guys I'm already pretty much set up. I mean, I came to y'all with a pitch deck of what I wanted the next eight months to look like, so for me, it was, more about the education of how something worked, which is what I cared about.
It's oh, everyone in this building is on salary. Oh, you guys don't work off commission. So if my album does good or does bad, you still get paid the same amount of money. Got it.
Educated. Okay, cool. I don't like that.
[00:25:19] Aaron: Exactly that.
[00:25:20] Jesse: Not if I'm giving you records that I'm making. No, no, this is different. Now, if you presenting me with opportunities that propel my career, then cool. But if you calling me and telling me, ah, man, we want you to do this campaign with the journeys. that's not really my bop guys. You didn't do your research.
Yep. Laughter Laughter
you know? So it's like, I think it's just about, self awareness. You learn more and more about yourself the less people involved. fortunately, I learned so much about myself, because there wasn't that many people involved in the beginning of my career.
So I had to know who I was, and I had to know what I represented, and why I did what I did, and down to like, writing all the lyrics to all my songs, and being like, you say that word in every song. That is Why? I think that journey of understanding who I am as an artist and a person helped me make a lot of decisions, even being okay to leave because people are like, are you leaving?
You just got there. I'm like, nah, don't get it. I'm uncomfortable in a way that I can't learn from. I'm okay with being uncomfortable if I'm learning something. If I'm uncomfortable and there's no lesson being taught to me, then I'm like, there's no point. I will take my blows and I will take my dents in my armor and I will move on to the next battle.
it helps when you realize that if no one called you to make something, you made it, you're fine. they need.
Somebody to say, we we need to turn this record in by August, Jesse. No one has to tell me that. that's what I do for myself and so many people. So if you don't have to tell me that, and you're not helping me with the art direction, because I'm coming up with the ideas for art direction, you're not helping me with this, but you want this percent of this.
And you want me to wait the math is, it's getting weird. Now, now I'm thinking it's good enough. I'm starting to question if I even should make art, if I should get a real job. That's too much. What's the point of you? You're not supposed to make me feel like this. You're supposed to make me feel like I can do anything. That's what you're supposed to make me feel like. Your job is to be supportive. So if you're not good at supporting, why am I around you?
Allowing you access to the thing that I made from my heart and my soul that speaks to things you cannot explain or understand?
Why, am I here? I've gotten myself and other people out of deals based on language, being able to express what the importance of creativity is to the world, to executives, to be like, yo, you know, if we didn't exist, you wouldn't exist.
What would you do
[00:27:31] Aaron: Yeah! Yeah. Exactly.
[00:27:32] Jesse: like where would you be at coca cola
[00:27:35] Michaela: record labels are interesting to me because like I worked at a record label right out of college. I worked at Nonesuch and I remember like seeing different things in the press about different bands, like Wilco leaving Nonesuch and like airing different grievances about their record deals.
And I didn't know the ins and outs of What those deals were made up of all I knew of the record label where the people that sat in the office and worked on that band's behalf. So I was like, Oh, my God, but we love you guys. you know, but I wasn't making the contracts and the deal points.
So I have that perspective of like, record labels are made up of people, a lot of them well intentioned, passionate people. But there's all this other stuff that happens, the contracts, the deals, master ownership. And the fact when we created this system of record labels, it was decided that everyone who works at the label gets a salary, paid time off, and benefits, health insurance.
How come it was never decided, okay, if we're going to sign an artist for a year, why don't they get a salary and benefits while going out there to tour and promote the record? And labels who decide oh, one of our biggest marketing points is Based off of you touring, but we're not going to give you any tour support and you have to incur all the expenses of touring.
This is a really backward system.
but we've just accepted it because it's been what it is. And I've slowly been like, wait. I don't like this I'm going to make a record you're going to financially support it and do the accounting all in the way that you guys think you should. I'm not privy to that information.
I'm just supposed to trust you guys are accounting and doing all of it as you are. and in some deals and my deals, for instance, you own my record for the rest of time.
[00:29:18] Jesse: Yes. See, doesn't feel good. I made it!
yeah. Yeah.
[00:29:22] Michaela: Money, Money trumps creativity, skill, the training we all go through to be able to do this.
Money trumps all of it. And I'm like, only because we've agreed on that.
[00:29:33] Jesse: Yeah. My new thing is I tell all the homies to audit. Working with a pretty big artist last year. I was executive producing his album year before last year, but we released last year. And at one point in time, he's like, Oh, we don't have money for this. We don't have money for that. And I turned and I looked at him and I said, Hey, Didn't you record your last album at home?
He's like, yeah. And I'm like, okay. If you recorded your last album at home, shouldn't they owe you money then? He's like, what you mean? I was like recording budget that should go to you. Cause they were going to give it to a music studio. If you were going to use a studio. I was like, you should probably audit them.
I already knew that that was the case. I just, I feel weird that management didn't tell you that. That's the first thing I would do as a person in support of you is to find where money was or where there's dents and we need to fix the dents and not drive the car still act like everything's fine. The car, I'm like, how did I get that scratch? You're supposed to. You're supposed to.
[00:30:21] Michaela: because you think, as the artist you're never really in the position of power. It's always, okay, but let's not rock the boat, let's trust it because we want to keep this deal, we need the support, we need the access
[00:30:32] Jesse: I rocked the boat. I shake shit up. Michaela. out of respect for certain artists, with certain labels or whatever the situation is, I'll honor what the artist tells me. give them something to care about, I'm not unaware of the power I possess. Just as a musician, just as an artist, as someone who's made music, that somebody probably liked that probably know that person. even my UMPG deal, like I was stuck in my deal and I owed him, I don't know, I think I owed him like 25, 000 or 16, 000 or something like that. And they wouldn't let me on my deal because they knew I had records come in that were pretty big records that I was a part of that I wrote.
And I wrote an email to the chairman of the company. And I told her and my rep who's right under her, who was the, vice chairman, I told him in an email I'm the artist, and that feel as if, I'm not feeling supported by the people who I'm in business with, then I'm creatively stumped.
And if I can't reach my full potential creatively, then I'm of no use to anyone, especially not myself. I said that you guys say that you're for the artists but I'm not feeling what you guys spoke to in this wording in this interview that I found and I copied a billboard interview quoted from this person wouldn't let me out the deal and I put it in the email. And I said, hey, look, this research this. I'm delusional here. You said you live like that and that's how you guys live. And I'm telling you for nine months that's not a representation of what my experience is. And I'm willing to pay the money back that I owe you guys.
So it's not even like you're losing money. Just, I just don't want anything to do with you because you don't represent what I represent. you know, everybody got mad and I had to fire my management off of that, cause they wanted me to apologize. And. My lawyer called me the next day and told me, you know, what happened like in the email that they took me out of. So I kept my lawyer. I said, I like you. I'm gonna keep you. Everybody else kiss my ass, including the chairman of that company. that's how am for myself, and I go harder for the people that I care about and I make music with. So, Yeah, I've been in situations where I've had to call, the head of and be like, yo, You don't know me, but you don't want to know me. Not like this.
[00:32:26] Aaron: how did that play out after that? both on a business side and on a creative side. I can imagine what both are,
[00:32:32] Jesse: I got out of my deal and I got
Into a new deal, a better one, Those records that came out, went to my new deal. And got a studio space. And I got a car I was like, Oh shit. I started managing and I got four people publishing deals the next year off of albums that I executive produced with them one of the people I got a publishing deal for and I executive produced his album and made all the music with him that he's been releasing. And then I learned the language of how to communicate certain things to certain people in positions of power.
So when it came time to having to advise anyone else or, people who come to me and be in their own situation and not understand how to go about it, I would do some research with them a little bit or just show them something. it opened up a side of my brain that I was always there, to me it's just reflecting of life really, it's like you go to the grocery store and buy something that isn't good, Like the produce goes back, you go back to the grocery store, right? And you ask to talk to the person in the highest position and you say, Hey I brought this zucchini and I opened it up at the house and this zucchini is not the zucchini you said you had here.
What can you do about it? And they either go, here, you can get your money back for the zucchini. We're so sorry. Or they go, here's a better zucchini. That's life. So hey, I read this contract and everything you said you was gonna do in this contract. It's not really happening I'm feeling like I'm having to do more.
What can you do about it? Hey, we can make the contract better or you know what? I got your money back
[00:33:54] Aaron: know, okay, that contract, that zucchini is not for me and I'm gonna go get my zucchini somewhere else. You
[00:34:02] Jesse: like, It's really simple when you think about from that standpoint from like as practical as possible but we are such overthinkers as creatives and we have so many different voices in our heads that speak to one thing we bring those voices with us to every other thing And i'm like in the creative space It's amazing.
I yes to all of you guys. Talk to me. Tell me Oh yeah, I should add percussion on here. Brazilian percussion on here. We should go 6 8 back to 3 4 halftime. Okay, cool. That part, cool. But on this side, I don't need all y'all voices. who the two most logical is. Y'all come with me.
Everybody else stay.
[00:34:38] Aaron: hmm.
[00:34:39] Jesse: I don't want to have a conversation with someone and they're like, oh, this person is just all over the place. No, I'm not all over the place. It's a lot happening in here but I'm going to get to my point, you know, so I just make sure that I know the point and what it is and why I'm going, same as going to back to a grocery store to get my money back for something.
I'm not going there and being like, yeah, so I bought a broccoli and strawberries from this place. And it was just great. And then I went to, I don't need them to know all of that. I don't like this. hmm.
it. Give me another one and give me my money back. The strawberries I got from the farmer's market does not concern you.
And, the damn broccoli I bought from this random farm driving home that don't concern you neither. So, focus.
[00:35:16] Aaron: The two things that ring in my mind, one is there's this general, stereotyping here, but there's this general expectation that artists, people in our position won't put the effort in to do the things such as like auditing. That's in most people's contract, but they're kind of banking on the fact that you're never going to do that because You got to write this letter. You got to ask a certain way. It's going to take
[00:35:35] Jesse: I get a lawyer to a lawyer to do
[00:35:36] Aaron: Yeah, all of that, you know, and that goes along to having to go to four different markets to get what you want for your recipe or whatever it is. And the second thing in hearing you say all of this is I get the strong sense that you know the tools in your toolkit and you know what tool to use on what thing you're not showing up needing a skill saw with a screwdriver.
Like I'll make this work. it's like, I have this tool. don't need to know how many screwdrivers I have, but you need this screwdriver. So here you go. that's a really strong asset.
[00:36:04] Jesse: That's literally how I look at a lot of things, cause I do so many things I'm presented with so many different ways of expressing the things that I do. I would say, you know, What do you want? cause I can tell you, Oh, I don't have that. we won't even have to waste time.
Mhm.
Instead of me going, Oh, I got this. And then I got this and I got this and I got this and I got this. And somebody goes, Oh, I came here for this. Oh, but I know somebody who could You want this kind of uh, got some, I call them, see if they free, I connect y'all, It's what I asked myself, like in a situation with UMPG and with Def like, what do I ultimately want? And for me, it's creative freedom.
Mhm.
I want to be able to tell myself, I'm going to release this now. If I change my mind and wake up tomorrow and say, I want to put it out tomorrow.
If I say, you know what, I only want to put this out on final. I don't want this to come out on DSPs. I just want freedom.
Mhm.
want my freedom to be championed because I have good intention and my messaging is always to elevate and support and question and cause thought provoking conversation. if you're not in support of that, then we cool.
[00:36:59] Michaela: So my question though is, how do you have the emotional and mental resolve In all of those different moments.
[00:37:08] Jesse: Oh,
[00:37:10] Michaela: and feel like you have the leverage to stand up for yourself and choose those things. Even when you're standing up against a company that, said, actually, we don't know if we want to keep you and start questioning yourself and your worth and your talent and your connection, how to then find your emotional strength to be like, wait a second, my worth is not coming from the outside world.
Not from a company telling me I good or selling out a bunch of shows or undeniable, social media or streaming numbers. But my worth is coming from my knowledge of myself and my being an artist, no matter how many people know who I am or what selling power I have. And that's enough to make me feel confident in standing up for myself and choosing, because I'm asking this personally, because this is what I struggle with.
[00:37:56] Jesse: that's easy. I mean, so funny, you know, because we're in such a like, state of dependency on social media, we like forget, the root of everything, I always often look at everything as like trees or plants, My therapist said this to me the other day and it's so crazy because my company is called new growth creative activities, new growth, She said, we're all seeds.
The seed has all the information to grow, right? Depending on where it's planted, depending on how much water it gets, then it'll grow to this fullest potential. If it's in a bad soil and it's not getting water and not getting love or talk to, then it won't grow the way it's supposed to grow.
But we all have the information. So I remember when I was stuck in my deal, I went back and I listened to. All of my music. at that point, I was not listening to my first project on my second album, my third album.
And then, so I'm listening to my first album. I'm like, wow, I made this in a basement in Jersey and at new school.
My first album. And I was like, I put it out on my space. I got 5, 000 downloads the first week. I think it was. Then somebody asked me to do a show in Baltimore. I had never even done a show outside of Baltimore.
Then I went to D. C., then I went to da da da, then I made a video that was on BTJ. Wow, that's kind of cool Then I go, let me listen to my second album. Listen to the second album, I'm like, oh, I did this album time we moved to Brooklyn. That's how I met Steve Warman, one of the most amazing musicians I've ever worked with.
And me and Jeremy Most did a lot of records, and all my closest friends. Burnis. Oh we tour? Oh yeah, we played, we went to Europe with this shit, London. Oh yeah, Soul Train Award. Great! fuck? I did that at the crib! Then I listened to my third album, I'm like, Hmm, Damn, I did this album with all my homies.
Then I got this label called Ninja Tuna, put it out. they didn't even know why I told them. They wanted a solo album, I told them no, I needed to support my community. And we had this clique called Romantic Movement. Nobody told me that to do either and I just they bought in they did it cool I just go back to me like i'm talking about listening to the senior recitals at new school like I listen to everything to remind myself the fuck I am? You know what I mean like shit important, you know because we get so complacent, and we get so caught up in expectations of other people's emotions. We forget how powerful our emotions are you know what I'm saying? You weren't influenced by the women and the men you were influenced by in the field of music you love. I just remind myself so like I'll go do that then I'll go watch a bunch of prince interviews I well, I gassed myself up.
I'm like, I knew I wasn't tripping. I go watch some kanye interviews. I'm like word i'm with you I watched some bob marley peter tosh back by the time it's time to talk to them I'm lit up You know what i'm saying? I got me and I got my ancestors behind me. They just back there like what's up like everybody with me, I galvanize myself, I think it's important and a lot of times we get so caught up with doing it for other people and other things and other reasons that we Forget like it start with us, have that issue all the time, and that's why I got a therapist and that's why I do the reminder thing why I like play on my albums or like I go like watch old videos of myself that I'm like, I had a durag on with a tall tee.
I'm singing in Crash Mansion, I'm like, yo, who is this guy I need him back. I want him with me now. So that's what I do. Like constantly. Every time I get ready to release album, I go back and I listen to all the versions of me and I try to do like a little transformer super hybrid and I go, ah, let's go.
[00:41:09] Michaela: one of the things I've been thinking about lately because of where I'm at in my career and life and early motherhood also, and the impact of that on a woman's career is, very real. And I'm realizing there's this outside expectation that I internalized Oh, you're supposed to be in certain places by certain times, and that it's just not how it works, But I've really believed that, and I've started to realize that, and I've gone back and been like, remember when like, I wasn't expecting anybody to give me anything.
I was doing everything myself. I wanted to make a record. I paid for it. I like borrowed money against my life insurance policy that my parents pulled out for me
[00:41:50] Jesse: I'm with
[00:41:50] Michaela: first record. Yeah. And I wrote my own press release and I mailed it out I did all this stuff and I'm like, I need that energy back,
[00:41:58] Jesse: know what I'm saying?
[00:41:59] Michaela: yeah, but because I'm in my late thirties and now have a family, I'm like it's supposed to feel different or look different.
And I'm like, we all think we're in these unique experiences alone. And when we talk to each other and when we share and can listen to podcasts of other people's conversations of oh, wow, this artist who I, greatly admire and think has it all together.
Oh, they have these same feelings, even like referencing the new school that you said early in the conversation, I also felt out of place and connected with you on that. I never knew that until this moment.
[00:42:33] Jesse: one, no one.
[00:42:34] Michaela: mind, Jesse, you were like, the king of the school.
[00:42:37] Jesse: I would get off stage some people walk up to me like, I don't know, Jesse. I don't think you've got it, bro. I don't know. People Would tell me that at
[00:42:45] Aaron: Yeah. I heard the same thing.
the thing that rings for me through all of this is like dark side of ambition, your ambitions here. And so like inevitably you're going to constantly compare like where you are assuming that you're at versus where your ambition wanted to be,
[00:42:58] Jesse: Yeah,
[00:42:58] Aaron: record, the day, whatever that is.
And so you're going to see all of those gaps that nobody else sees. you going back and looking at your previous records, Jesse and everything that you've done and how you got there. And What you guys were focused on the firing up were the positives and it's so easy to look back and see how it didn't stack up how it didn't reach far enough and that's going to do the
[00:43:15] Jesse: Oh, yeah, yeah,
[00:43:16] Aaron: pull all the wind out of it.
[00:43:18] Jesse: Yeah. I think both sides are important. You know, I think for me, going back to what you were saying, Michaela, about you not knowing that I was, I felt out of place and you had no idea at the school. Like, I didn't want anybody to know.
I don't spend time in that space.
So yeah, it was a part of my experience, but it wasn't my experience, same, with, certain aspects of my career, I'm like, Ah, man. Grammy nominated, but I still ain't winning a Grammy. Ah, and then I'll go to the air one and I'll meet Harvey Mason Jr.
He'd be like, oh, you Jesse Boykins III. I'm like, you know me? He's like, yeah. I'm like, ain't you the guy who run the Grammy fund? He's like, yeah. I'm like, oh, You're just a man guy.
we had this time, in our youth, I'm sure where you just envision like How crazy this is.
But then you're like, it's not actually that crazy,
you know? And it's yeah, I still Desire certain things, but they don't rule me. people don't rule me. And that's why I love being an artist so much. I seldomly have moments where I think about getting a job and I'm like, yeah, only if I get to write the scope of work.
If I sit down and I say these Are the things that I'm gonna do and if you hit me about any other thing I'm gonna tell you kiss my ass and you gotta still pay me. I'm lit that's
Mm hmm. You know what I mean that's artistry, you know, it's like yeah I will play a show if you pay me this amount of Money or if I feel like it But i'm not gonna do it if you're gonna treat me like shit when I get there, huh?
I'm gonna see you later. You know, We're blessed to be in a space where we can make things that automatically create value for us, even if we don't know how valuable it is in the moment. you never know, something that you created 10 years ago, someone might hear and someone might be like, you know what, we want to put this song in a movie and it's with Tim Burton.
no one can tell you that it's going to happen or it's not going to happen. I love to live in that space. I look at my music that way. I look at everything I create that way. I don't need instant gratification. I don't need everybody to hear it right away.
I don't, that's not my main concern. I just, if I'm going to be intentional, then I'm going to go, you know what? I made this record and I think these five people should listen to it. And I will do all I can for those five people to listen to it. I will find those five people If nobody else listened to it, I could care less.
I look at everything like that, you know, like levers, when I used to do shows in New York, I'd be like, all right, cool. Yes. I'm selling tickets and everybody could come, but I need these three people to pull up to my show.
I will send them flyers, I will tell them they get the backstage access, whatever they want, they get the drink tickets, I don't care, I need them people, so that's how I look at things. It really helps with a lot of things, even down to like, when I'm doing albums with people, you know, I say this thing where I'm like, yo, you're setting up a dinner and you're gonna invite five people that you admire.
To this dinner, who would you invite that narrows everything down? It's, you know, that focuses everything that, you know, we're demographically speaking to, you know, what the style is. You might know what the tempos are based on you because they probably all close in tempo choice and shit. You might know what key like it's like making a grocery list before you go to the grocery store, you know, or making your list. Morning when you wake up before you get on your day. It's all the same, you know We try to make it so complex and i've just been trying to make it more and more simple I just need the simplicity, you know So i'm not concerned with what other people tell me to be concerned with i'm concerned with the things that I concerned with and I will place the people in the space with the same concern Like we all got this concern.
So we're gonna try to figure this out together I like that way better. I don't like being like, well, I'm concerned about this and you're concerned about that. We should work. It's not going unless you say, you know what, I'm going to take the time and push my concern away for a little bit and work on yours.
And then when we finish yours, then we'll do mine. if we get that kind of rhythm going and cool, but you know, if that's not the case I'm at the time in my life where I'm, cool.
[00:46:35] Aaron: That's such a beautiful bow to put on this whole thing, bringing it back to the beginning and Listing things out having intent having focus almost like a monotasking instead of multitasking let's attack this
[00:46:47] Jesse: fighting for what you deserve. it's fighting is bad. I'm, cool with confrontation. come on. I tell people all the time I die for my art and I mean it. if I didn't have it, I wouldn't know what to do with myself.
Y'all, y'all wouldn't have met get what i'm saying like that's how I treat it
[00:47:03] Michaela: I've been thinking about because you've used like the seed and a lot of nature metaphors and thinking of like a dandelion where you like blow it and there's all those seeds that you're like when you're making art You're just like blowing all these seeds out and some of them might land and all these different places You don't know how far it's gonna travel before it lands and
[00:47:20] Jesse: first of all pump breaks put a pin on that because that's a really beautiful you should run with that I like that visual. I get what you're saying. Musically. Oh, that's great.
[00:47:28] Michaela: But not even like, you know, career wise, but also just all the connections it makes. And when I think of years ago we went to New Orleans I remember going to Congo square and I was thinking about all of the history and like the tragic history and the beautiful history and Louis Armstrong.
And I was like, man, everything that happens creates a cause and effect and all these little dots that connect if Louis Armstrong didn't exist, our family wouldn't exist two little white kids wouldn't have ended up going to jazz school and, built this life partnership and a beautiful child.
And like, really trying to take a more spiritual. view of what this is, which I think when you're building a career and there's money and perceived success, it can be really challenging to stay grounded in that
[00:48:16] Jesse: For sure. For Like anything else, what is life without a challenge?
it depends on how you, what you do with it. I love, challenge me please. make me figure this shit out.
[00:48:26] Aaron: that's where I learn, you know, if
[00:48:28] Jesse: Yeah, exactly.
[00:48:29] Aaron: it's like I get bored.
[00:48:30] Jesse: Yeah, let
me figure this out, you know.
so yeah, I think that, the challenges are presented to people like us for us to be able to open up bring light to things that other people wouldn't be able to.
[00:48:41] Michaela: Man. Thank you so much, Jesse. This has been such an insightful, beautiful conversation. We really appreciate you.
[00:48:47] Jesse: appreciate you guys reaching out and congratulations on everything.
[00:48:51] Michaela: Thank you. Thank you so much. You too. All right. Have a great day.
[00:48:55] Jesse: Yeah.