Jereena Montemayor: Carving Her Own Path Through Music, Passion, and Self-Discovery
By. Alicia Zamora
In today’s digital age, where social media can launch careers overnight, Jereena Montemayor has carved out her own path with passion, persistence, and authenticity. In this exclusive interview with Alicia’s Studio, she takes us through her journey—from posting cover songs on Twitter during high school to becoming a rising independent artist. What started as a simple experiment quickly turned into something much bigger. Through sheer dedication, Jereena spent a year consistently uploading covers, each one bringing her closer to a breakthrough. That moment came with her rendition of Childish Gambino’s “Redbone,” a cover that unexpectedly went viral and validated all the effort she had poured into her craft.
Now, Jereena reflects on her transition from covering songs to writing her own music. Without any formal training, she relied on instinct and self-teaching, crafting raw, heartfelt songs in her bedroom and bathroom with just her guitar and a phone camera. It was through this process that she discovered her love for songwriting, leading to the creation of “Rose”—a song that she instinctively knew had the potential to be something special. This pivotal moment solidified her confidence as an artist, proving that she wasn’t just a singer but a storyteller in her own right.
As she continues to carve out her space in the industry, Jereena shares the challenges and triumphs of finding her voice. From early experiments on SoundCloud to navigating the transition into songwriting, her journey is one of perseverance and creative growth. Join us as we dive into this exclusive conversation with Jereena Montemayor, exploring the inspirations behind her music, the lessons she’s learned, and the path that led her to where she is today.
Diving In
Jereena: Hi, my name is Jereena Montemayor!
Alicia: Jereena, you’ve had an incredible journey in music so far. Can you walk us through the pivotal moments that led you to pursue music as a career?
Jereena: I think a big one was making a Twitter account. I actually gained my audience by making covers on Twitter, and that was such a big thing for me. At the time, I made my Twitter account around my sophomore year of high school. I saw how easy it was for people to go viral, and since I liked to sing, I wanted to test the waters. For a full straight year, I was making covers every two or three days, and at max, they would get 50 likes. At that time, I was like, “Hey, you know, I’m popping or whatever.” But eventually, it only takes one video, and for me, it was “Redbone" by Childish Gambino. I think that was a really cool moment for me. I finally felt like, Oh, all those covers went somewhere, and I worked up to that.
Jereena: Eventually, I also started making my own music and putting it out there. I would be in the bathroom or bedroom with my guitar, with my phone camera propped up. The songs would be super raw, but I started posting them, and people liked them. And I was like, Hey, okay, I’m not bad, I guess. I never had any training for singing, and I didn’t take guitar lessons. Everything was very self-taught. So I never really came into this thinking, Hey, I’m gonna be a music artist. That was a really cool moment for me. And I think just making my song “Rose" was another big part of why I’m here. I felt that moment of like, Oh, this is gonna be that song when I was making it. So it was cool to see that all play out and trust the things that I was doing.
Alicia: Yeah, so that’s a big shift because you started with covers. Once you started making your own music, how was that for you? How did you transition into that?
Jereena: It was very different. Growing up, I loved karaoke. My sisters and I wouldn’t make songs, but we would just mess around—it wasn’t really anything serious. Before I even gained an audience, I started playing around with SoundCloud. I would put stuff there for my 200 followers on Twitter. It was great, and people liked it too! So I was like, Okay, that’s something nice that I could still do, but it wasn’t like, I know how to make music or I’m a writer. It was never that. I think once I started feeling comfortable playing with my guitar and writing melodies, it was a lot easier than before. There were definitely moments where I hoped that I wasn’t copying a song. As artists, we have those thoughts like, This melody sounds familiar, but I can’t put a pin on it. There are definitely challenges here and there, but other than that, it’s been a great experience making music.
Alicia: How has your sound evolved from your earlier work to now?
Jereena: In the beginning, when I started making my own music, I was really drawn to heavy R&B—sultry, slow vibes. I eventually grew out of that, and it shows in my recent work. Beforehand, I was really drawn to Sabrina Claudio and Daniel Caesar—essentially that romantic R&B sound. But after performing so many times, I realized that there’s only so much I can do with slow R&B music. I really enjoy my upbeat songs because the audience is a lot more involved with them. It’s definitely a vibe with slower songs when I’m with my guitar, but I get that some artists are meant to perform in that way—where you can hear a pin drop. But for me, I’ve realized that I like to perform instead of just standing while singing. I like to have fun with the audience and include them. I think the songs I had before were very slow and had a specific vibe. I still love them—they’re still a part of me, and I can pull them out whenever I need to. But now, I really want to focus on what I enjoy. I love performing when I release a song, and I’ve realized that you can only do so much with certain songs. I think I’ve eventually grown into finding my sound.
Alicia: I feel like audience interaction is really important, especially at concerts. When I’m at a concert, I want the artist to encourage the audience to sing along or something so I feel like I’m a part of it.
Jereena: I’ve figured that out while performing at so many college shows. I always start off with a cover because it gets them to start singing with me. Usually, that sets the vibe right even if people don’t know me yet. It’s a scary thing when they’re just watching, and I’ve felt all of that.
Alicia: Was there a specific experience or influence that inspired you to start making music in the first place? How did that shape your sound today?
Jereena: I think something that really made me go, I want to do that, was my first concert—Daniel Caesar. Like I told you, he was big during the Freudian era, so all of that was fresh. I think he opened with “Japanese Denim,” and it was my first concert ever. As soon as he came in, all you hear is that pa-chee sound, and I was like, Oh my God. By the time he got to the bridge, I was bawling, just crying because it was so beautiful. And I thought, Dang, I would love to do this one day. At that point, I had just started gaining a small audience, so it became a momentum thing for me. I was like, Okay, I saw that. Now I’m pushing through—I want to do that.
Jereena: Another moment was making “Rose.” While I was making it, even just playing the chords and humming the melodies, I felt it—Oh, this is going to be that song. In the beginning, it was doing great, but by my standards, I thought it would do better. Then, a few months later, it was luckily on people’s Discover Weekly on Spotify, and that boosted it so far up. I was like, Whoa. That reassured me that some things take time. At first, I thought it would do better, but then after a while, I was like, Okay, no, I was right. Things just take time, and I don’t need to rush the process. That was a big lesson for me—to trust what I think is going to be good and just stick with it.
Alicia: You said you had this mindset of doing it by yourself. How did you get out of that?
Jereena: A lot of sessions. I graduated from college in May 2023. My degree wasn’t music-related at all—it was in early childhood education, so teaching. When I started working with my manager, he was very patient with me. I told him that I needed to finish school first, and then after that, we could focus on music. After I graduated, I booked two weeks in New York, where my manager is based. He put me in sessions with a whole bunch of people almost every single day that I was there. That was a big shift for me. I had been in college mode for so long that I wasn’t really creating music. At first, in those sessions, I probably thought my songs were cute, but now when I listen back, I’m like, Woo. I can see how, beforehand, I didn’t have the guts to say, I don’t like that. But now, I know I should have. I definitely figured that out through the confidence of being in the room with people and just from all the sessions I’ve done. It was both difficult and easy—difficult because I was adjusting, but easy because whenever I couldn’t think of something, there were people around with great ideas to bounce off of. It was really cool.
Alicia: Do you think your music reflects your personal growth as an individual? If so, how has it changed over the years in terms of themes, style, or production?
Jereena: Yeah, I mean, I think growing up—yeah, I was outgoing—but I was also somewhat reserved. And I feel like that's how my music was before. Very like, Oh, I like you, you like me. But I think now, I’m just like, OK, I’m a big girl. I can do a whole bunch of different sounds that I probably wouldn't have tried before because I was too scared. But I feel like it’s just more so about feeling comfortable with the music I make and knowing that even if it’s a different sound—something that’s not what people expect from me—it’s still a good song. So yeah, I think transitioning from being an R&B artist to trying to say, OK, I’m not just “Rose” or that kind of sound, I want to make that shift with my music.
Jereena: Other than that, I still stay true to how I write, how I write melodies. There are still a lot of aspects of me that haven’t changed, which is the reason why I still feel connected to my old songs no matter what.
Alicia: What has been the most challenging part of your journey as an artist, and how have those challenges influenced your music and message?
Jereena: I feel like consistency was one of them. I would drop a song and be like, Bye, see you later. Also, now I think it’s the marketing aspect. We don’t live in a time where you can just post your song once and then disappear. There are people grinding and putting their songs out every single day, which I love. I think that shift has been difficult for me. I know it's a business—I eat, sleep, and breathe music—but sometimes, I feel like I’m forcing my music on people if I’m constantly saying, Hey, listen to my music! It’s that kind of energy. And then, there was the two-year hiatus. I think that was a lot of time—not lost—but just a long period of figuring out who I am now. That took a while. I’m also a perfectionist. “Traffic” was made the same week I first went to New York in 2023. It’s still my favorite song I’ve ever written. I told the producer already, I think it’s perfect. I knew from that moment, Hey, we’re gonna be here for a while. But it was good—it turned out really great.
Alicia: Yeah, definitely. I feel like sometimes a break is just needed. It helps you create more. When you were on your break, were you still writing songs?
Jereena: Yeah. A lot of the songs I wrote during that break are the ones I’m releasing now. It was just about finding the sound and the right people to make it with me. So yeah, while I did say time lost, I don’t actually think of it that way. I’m grateful because I really discovered what I like and what I don’t like.
Alicia: What has been the most rewarding moment in your career? Was there a breakthrough moment that made you realize you were on the right path?
Jereena: Oh yeah—“Rose.” I was in my bedroom, and the minute I started humming the melodies, I knew—Oh, this is the song. It was crazy for me to feel that because before, I think I was just doing music for shits and giggles, you know? But after “Rose”, I was like, Wait, I think I can actually do this. And working with that producer, I felt like, This is the first sound that represents me.
Jereena: Before that, when I made songs and people played them, I’d be like, Turn that shit down, turn that shit down. But with “Rose”, I was like, Hey, turn it up! I was super, super proud of it. It was the first song where I really felt good about what I made. That was a big moment for me. And honestly, the messages I get from people—that's been one of the most rewarding things. Sometimes, I’ll get random emails, just paragraphs from people saying a certain song helped them. And I’m like, Whoa. That kind of thing is so heartfelt for me that I literally want to throw up—but in a good way! It’s overwhelming in the best way possible. I love it. It’s so sweet. I wouldn’t trade it for the world. I think sometimes when I get tired of creating, I remind myself why I do it. It’s for those words, those messages. I’m a super sentimental person. Anytime someone says something really sweet and emotional, I’m like, Waterworks—we are going to cry. But I really appreciate those kinds of messages. They help me trust what I make and keep going.
Alicia: Yeah, I definitely feel like, especially for creatives, when you get supportive messages, they mean so much. Like, I can get a comment on something I wrote, and I’ll be like, Maybe I’m on the right path. Maybe people actually like what I’m saying.
Jereena: And you get it too—you’re creating something. Any little message means the world. It’s a feeling you really can’t take back. So I totally get it.
Alicia: “Traffic” is a huge release! What can you tell us about the inspiration behind this song? What’s the story or message you wanted to convey through it?
Jereena: I was actually super, super inspired. I’ve loved Olivia Rodrigo and even before “Driver’s License" was released, I loved her in the series. I would look at her profile, and that’s when I realized how crazy of a writer she was. I became so obsessed with watching her unreleased songs. It was the same thing with me and Twitter—just her sitting in a bathroom or her bedroom, and I was like, Whoa. She was 16 and making these really heartfelt songs. When “Driver’s License” came out, the bridge—I think I started levitating, like, literally. I was like, Something about this bridge—it’s crazy, it’s amazing.
Jereena: I get inspired by good songs, and with “Driver’s License”, I thought, I really want to write a song where I’m so proud of the lyrics and everything, because I hadn’t felt that in so long. I sat down at the piano we have, and I’m not a piano player. I’ll put my hands on the keys and be like, Oh, okay, this sounds nice. I didn’t even know what I was playing. I was taking pictures of my hands at the end because I didn’t know what chord it was. I just thought, These are nice, pretty chords. At first, I wrote something different, but I revisited it the next day. That’s when I switched up the melodies and sang it a different way. The song starts off with getting ready for a date night. And when I said, And your GPS says LA, I wanted to play with the meaning of Traffic. Usually, traffic has a negative connotation, but in this case, I wanted it to mean something different. You want traffic so you can spend more time with someone.
Alicia: When you were writing this, did it come more from personal experiences or more from imagination?
Jereena: It was definitely imagination. I was in Houston. I think this was one of the first songs where I stepped outside of my usual process. Normally, I write about my own experiences, but “Traffic” was one of those songs where I put myself in a different box. I challenged myself to write something outside of what I was used to, and it came out great. That was a big part of why this song felt special to me.
Alicia: What was the reaction like from your fans when you released “Traffic”? Did any feedback stand out to you or surprise you?
Jereena: Yeah! A lot of it was my friends telling me, Dude, I listen to "Traffic" like crazy, and I’m like, Heck yeah! Or they’d say, The bridge, dude… and send me GIFs of people doing a chef’s kiss or things like that. I love that because they’re not musicians—they’re just music lovers. And knowing that I can appeal to my friends, that’s really cool. The audience and the fans were also really, really sweet. “Traffic” definitely feels like a step up—or more like three steps up—from my old stuff. But at the same time, it still resonates with my older songs and the way I write. A lot of it is still the old me, that bedroom-style writing, but it’s more elevated. This time, I was like, Strings? Yes. Drums? Yes. I knew exactly what I wanted on the production side of things.
Alicia: If you could describe “Traffic” in three words, what would they be and why?
Jereena: Ooh, I would say cinematic because when I first started writing it, I wanted it to sound like a soundtrack—like something you’d hear in a movie. And we definitely achieved that with all the elements we put into the production. I’d also say favorite, because it’s my favorite song I’ve ever written and my favorite production I’ve ever done. And lastly, safe. Anyone you feel like you could spend time stuck in traffic with is someone you feel safe with. That’s the feeling I wanted people to have when they listen to the song and think of someone special.
Alicia: Is there a specific moment or lyric in “Traffic” that means the most to you personally? Why does it resonate with you so deeply?
Jereena: I think it’s more about the dynamic of the song. When the bridge hits, I’m singing, No, don’t take me home, and I feel like that’s the exact feeling you have when you’re going home after having a really fun time—you don’t want it to end. Making the bridge really big was my way of expressing that emotion, like No, don’t take me home! It was an emotional connection with the music as well. I also mention the stars in the bridge—something about wanting to stop and watch them. But in reality, I’m watching him, and I’m saying that he’s the star. It’s like this little mind twist, and I think that combination of lyrics and dynamics really reflects everything I wanted to convey.
Alicia: And looking ahead to upcoming projects, what can we expect next from you in terms of releases? How do you see your musical journey unfolding in the next year?
Jereena: I definitely want to work on a lot more upbeat songs—songs that make me enjoy performing live. Right now, I’m working on an EP. I still don’t feel ready to make an album. When I finally say, This is my first album, I want it to feel like the moment. But for now, I’m taking baby steps.
Jereena: A big focus for this EP is making sure I actually enjoy singing the songs live. I picture performing them with a full band because the people I’m working with on this project—one’s a drummer, one’s a bassist, one’s a keyboardist—so we naturally end up doing a lot of live arrangements while making the music. I want that energy to carry through in the final recordings. There’s definitely a lot of upbeat stuff, but also the very lyrical, classic Jereena “bathroom hits” that I love. I just want to have fun with this project. I’ve told a lot of my producers that sometimes, I feel like my songs are very reserved, but I actually have a big vocal range. One thing I want to do on this EP is sing—like really push myself vocally and feel comfortable hitting those notes live. I want my melodies to reflect that confidence. So, expect a lot of singy songs—definitely not whispery, low-key tracks. I want them to be big and fun.
Alicia: Are you planning to experiment with any new sounds or genres in your future work? What direction are you most excited to explore?
Jereena: I have a lot of different ideas. I’ve always loved old-school Demi Lovato—Here We Go Again, La La Land—that Disney Channel era. Those songs were super punk-pop, and any time I do karaoke at home, I have so much fun singing them. So some of my new songs have that kind of influence. There’s also one specific song I’ve been working on that I always describe as the opening track of a 2000s high school rom-com movie—like the scene where the girl’s getting ready. It has that All-American Rejects kind of feel. But at the same time, I still have my very raw, acoustic Jereena songs—just guitar, some strings—that remain a big part of my sound. Aside from that, I definitely want to keep exploring. I even have some Dua Lipa double-clap type songs that I’ve been working on, which I’m excited about. I want to perform more songs like that because I love to dance. Eventually, I don’t just want to sing—I want to perform. So when I make music, I think about whether I’ll be able to create something more visually and physically with it. But yeah, it’s been really fun so far!
Alicia: When you explore different sounds, do you ever feel scared that people aren’t going to like it because they’re used to something else, but you’re creating something new?
Jereena: Oh my gosh, totally. Most of the time, my manager isn’t with me when I’m doing sessions, and since I have creative control, I can do whatever I want. But when it’s time to show the songs, I get nervous. I’m like, Ooh, this is scary—will he like these songs? These are songs that I actually love and enjoy, so it’s nerve-wracking. Surprisingly, the ones I was most scared he wouldn’t like—the ones I thought he might not be the biggest fan of—ended up being the ones he picked out. And I was like, okay, that was actually the song I wanted you to pick! So hearing that from his perspective was really nice. Obviously, he thinks about the business side of things, but as a creative, he also knows me. He reassures me, like, No, this doesn’t sound off. It’s not something too out there or scary.
Alicia: Yeah, I feel like trying something new is always good too.
Jereena: Yeah! You don’t grow when you’re comfortable. So I’m like, Hey, let’s do something scary. I tell the producers, These are the inspo songs I have or this is the kind of vibe I want to embody. I’m really grateful for the producers I work with because they never say, Ooh, this is kind of weird. They’re always so down for it, no matter what. And they always make something great. I think I’m just super blessed with the resources and the people I have around me.
Alicia: If you had a dream collab, what would it be? And what kind of energy would you hope it brings?
Jereena: Growing up, I wasn’t a Belieber or a Directioner—but I was an Arianator. I love Ariana Grande. If I had a dream dream collaboration, it would definitely be her. She stacks her vocals crazy—same as me. There are times where I’m just like, How did she even hear that? And yet, it all works so well. Also, she and Tori Kelly were my biggest inspirations vocally. I studied the way they do their runs and how they hit their high notes. Eventually, it just made sense why I’d love to collab with them. But I’d also love to work with Daniel Caesar. I’m such a big fan. I love him. His Freudian album? Insane. Like, “Blessed”—that song? "Yes, I’m a mess, but I’m blessed to be stuck with you". That’s a crazy lyric. There are certain songs where I’m like, I wish I wrote that. Daniel is so talented.
Alicia: You mentioned that you saw him live. I want to see him live so bad.
Jereena: I’ve seen him like four, five times. No joke. He’s the one artist where I’m like, Fine, I did this to myself—I have to go to every tour now. I can’t miss a single one. So no, I totally get it. He’s amazing.
Alicia: Do you have any upcoming performances or live shows in the works? And how do you approach preparing for a live performance? What kind of connection do you hope to create with your audience?
Jereena: I do have some performances coming up. I call April my Mariah Carey month because that’s when colleges usually have their end-of-the-year events, which is really nice. I’m super grateful for those opportunities. I have a show in Chicago on April 5, and then one in Minnesota on April 12. I’ve never performed in either of those cities, so it’ll be a lot of firsts—but I’m really excited.
Jereena: As for preparation, I feel like I go into autopilot when I’m performing. Even when I practice, I’ve done my set so many times that I feel really comfortable. But honestly, the first few minutes before I go on stage, I still get the jitters. I’m like, This is scary. It usually takes the first few lines of the first song for me to be like, Oh, this isn’t so bad. But those first few notes? Always a little rocky.
Alicia: How do you usually deal with jitters? Do you just go up there and push through?
Jereena: Oh my gosh. So I need vapor rub and cough drops. I love them. Ever since I took a cough drop before a show, I realized, Whoa, my nerves aren’t as bad. When I get nervous, my throat tightens up, which makes it hard to control my voice. Once I started doing vocal warm-ups and adding a cough drop into my routine, I felt so much better. It helps me feel less nervous and more comfortable. I even bring them to studio sessions. My producers know—they’re like, Do you have the cough drops? And I’m like, Duh. And then after they try one, they’re like, I haven’t breathed this well in ages. I get it! I always tell people, If you lose me, just follow the cough drop trail. That’s how they find me.
Alicia: Oh yeah, the vapor rub is so strong—it’s crazy. Some people are like, “Whoa,” because it hits you out of nowhere. There’s also this nasal inhaler version, and it’s insane.
Jereena: No, seriously. That was a life hack for me. It wakes you up instantly. Like, if I’m nervous, I’m not nervous anymore—because that’s all I can focus on! It completely distracts me. So yeah, that’s my warm-up!
Alicia: Music is such a powerful way to connect with others. How do you hope your listeners feel when they hear your songs? What kind of emotional experience are you hoping to evoke?
Jereena: I feel like I really want to set the picture well—so even if someone hasn’t experienced what I’m talking about, they can still be like, Whoa, those lyrics are so well written that I can feel what she was feeling. At the same time, I love that my songs can have different interpretations. It’s crazy—like with “Rose”, I’ll see people playing it at their weddings, and I’m like, No one’s gonna say anything? It’s a breakup song! But okay, have fun! I get it, though—it’s such a pretty song that if you don’t really listen to the lyrics, you might not realize how sad it is.But that’s what I love. I just want people to feel something when they listen—whether they relate to it or not. And if they interpret it in a way that makes sense for them, that’s even better.
Alicia: Yeah, I feel like people have their own perspectives. Like for me, I write music reviews a lot, and it really depends on how you take it and how you hear the music. I can’t even write a review until I’ve listened to the song like 20 times.
Jereena: I love that. You have a system, and it’s working for you.
Alicia: Yeah, thank you!
Alicia: In your opinion, what role does vulnerability play in your music, especially when it comes to writing about personal experiences?
Jereena: I think I’m the most vulnerable when I’m writing alone in my room. I don’t think I’ve ever had a session where I’m like, Guys, this is the tea—here’s everything going on in my life. For songs that are really raw—just me and my guitar—I know which ones those are. But in sessions, I still get nervous. I’m like, Ooh, I don’t know if I want to say this here. And honestly, the industry is still so male-dominated. In most sessions, I’m usually the only girl in the room, and it makes me hesitant to open up. Like, Y’all aren’t the girlies! If I was writing with my girls, I’d be like, Okay, listen, here’s everything, but when I’m in a session with mostly guys, it’s harder to share.
Jereena: So I think that’s why, when I need to be really vulnerable, I prefer to write alone first. Then, once I’ve written something raw, I can bring it to the producers and be like, Okay, now let’s build on this. But the actual writing? That’s just me.
Alicia: Do you ever feel like being vulnerable stops you from writing in a certain way or from writing certain songs?
Jereena: In sessions, yeah. I don’t think I could ever be like, Hey, I’m really sad today, let’s write a ballad. That’s something I have to do on my own. It’s tricky, though—every artist has to figure it out in their own way. I think eventually, once I’ve worked with my producers even longer, I’ll feel more comfortable being like, Hey, I’m feeling this way today. But right now, some things are just for me.
Alicia: If there’s one thing you hope your fans take away from "Traffic" and your music in general, what would it be?
Jereena: Ooh. I hope they still see the songwriter and singer in me—the same me that was posting songs on Twitter years ago. But I also want them to recognize how much my music has grown. I hope they hear these new songs and think, Wow, the quality of what she’s making now is kind of crazy. I really feel like I’m finding my sound with each song I release. Before, I would settle—like, Okay, this seems like a great song, and that would be it. But now, I have so many more steps before a song makes the cut. It’s not as easy as just uploading it anymore.
Jereena: I’m really particular about how these next few songs represent me as an artist. If people remember my name and come back to check out my music, these will be the first songs they hear. And I want them to think, Whoa, this is great. The change is great. But it’s still her.
Alicia: To end the interview, what would you like to say to those who listen to your music?
Jereena: I will always be so grateful. I feel so much love and support constantly—even with how patient my fans are. I know I’m not the most consistent when it comes to dropping music, but I will always keep making more. It’s just about timing—waiting for what feels right and what truly represents me. But everything I’m working on right now? I’m so excited for it. Every song is made with the intention of making my performances more fun and enjoyable and showing a different side of me—something I couldn’t create if it was just me alone.
