The Best of Both Worlds
Kai Ivey: Full-Time Talent Manager, Part-Time Kai$$.
We linked up with a good friend of mine, Kai Ivey (@kai.ivey)—full-time talent manager, part-time rapper. One thing I really love about Kai is not just how good she is at what she does, but how effortlessly she does it. On top of that, she’s hilarious and just authentically herself—a trait that draws people to her whether she realizes it or not.
What’s funny is, for someone doing so many cool things, she’s incredibly lowkey about it.
When you meet someone and find out they rap, that alone is pretty interesting (depending on where you live these days, lol). But honestly, one of the coolest things about Kai is her work in talent management. It’s not every day you get to pick the brain of someone behind the scenes like that.
I hope this conversation gives anyone thinking about a creative career a new perspective—reminding you that there are so many ways to be part of the creative and entertainment world, even if you’re not the one on stage (although we HAVE to get Kai$$ on stage ASAP).
Friday, May 23, 2025, Norfolk
Cayla: So Jason was asking me before we came in here, "What does Kai do?"
Jason: Because you're not just an artist, are you?
Kai: Yeah… I never really think of myself as an artist. I forget I do music half the time. And the 9-5… I do cool stuff! I just don’t really talk about it.
I work in talent management—mostly influencer marketing. I've been doing that for almost five years. I handle everything from social strategy to brand deal negotiation, pitching… I actually use my degree, which is super cool. I’ve hit a lot of big milestones, but I don’t talk about it much.
That’s my work, and I really do love it. And then there’s the music—which I don’t even have the desire to make a living off of.
Jason: You want to keep it lowkey?
Kai: It could blow up however it wants—I don't care. But I appreciate having my 9-5.
Jason: So you actually like having a 9-5?
Kai: Yeah. I love it. I’m not working towards a rap career. If it happens, cool. But I'm not chasing it.
Jason: So would you leave your 9-5 if your music blew up?
Kai: Honestly? It would be a big struggle for me. I'd try everything to avoid leaving it.
Jason: What?! Don't block your blessing! You could always come back to a 9-5 later.
Kai: Could I though? I feel like I couldn’t go back.
Cayla: Playing devil’s advocate—if your music blew up, you’d basically be choosing a lifestyle. Music comes with that. But even if you can’t go back to “corporate,” you could still do the kind of work you do now—just in your own way.
Kai: Right.
Cayla: So what are you working towards career-wise?
Kai: There’s never been a title I’m after. I’ve always said I just want to make ideas happen. That can show up in a lot of roles. Even now, my creators come to me like, "I want to throw an event," and six months later—it happens. That’s my thing.
If I keep doing music or anything creative, I’ll probably have to step away from talent management at some point. But I see myself still working with brands or marketing—maybe in a higher-level or consulting role. I still appreciate that world and don’t want to lose it.
Jason: That’s dope you love what you do. Most people don’t.
Kai: And I love music too. I know if I dedicated myself fully, I could "blow" or whatever. But I don’t want that pressure. I like moving at my own pace. I don’t want the expectation to keep putting stuff out.
People already press me now. Right now, I like that music is something I do for me.
Jason: Where do you pull inspiration for your songs?
Kai: I was just talking about this. When people say they're inspired by someone, they tend to make similar sounds. That’s limiting to me.
I do get the Karrahbooo comparisons though.
Cayla: I think it’s the energy you both bring—like the way you make listeners feel.
Kai: I wasn’t offended. I like Karrahbooo. But I don’t want people to box me in. I also realize people haven’t heard a lot of my music yet, so I can’t blame them.
I pull inspiration from so much though. The other day I was listening to Jungle’s "Candle Flame" and thought—I need to make something like this!
Jason: That’s alternative. So you can go deeper in the bag.
Kai: I have stuff that sounds completely different from what I’ve put out. But I also work in marketing, so I know how to ride the wave for a bit.
Jason: And people are fcking with it too.
Kai: Exactly. Having a marketing background helps with my music. I’ve done this for others—now it’s just about the music. That’s why I haven’t dropped a lot yet.
Cayla: Is it because you’re still figuring out what you want to say or how you want to be perceived?
Kai: Yeah, kind of. I overthink it. I’m getting better in private, but I want people to hear the progression too. So now it’s about: what do I want to say at this moment?
Jason: Do you get nervous when releasing music?
Kai: Nope. I truly don’t care. Even if no one listens, it’s still number one in my library. I really don’t care.
Jason: So you're excited more than nervous?
Kai: Yeah. I’ve had overwhelming support from the start. I have no expectations. I’m not chasing streams. When I hit a milestone, I’m like—tough. But nah, I’m not nervous. I just won’t perform.
Jason: Why not? Everybody says that at first.
Kai: Performing makes me nervous. I’m fine with public speaking. I just don’t think my music is for that big stage.
Cayla: Some music is best experienced in certain settings. If you had the right vibe, I think you’d perform differently.
Kai: I’ve been thinking about that a lot.
Cayla: Some artists need different types of stages. Beyonce is built for the arena. Not everyone needs to follow that blueprint.
Kai: Right. And some aren’t even following the blueprint right! (laughs)
Cayla: (laughs) Facts.
Kai: Like when JT did her club tour? Perfect. Or when Drake dropped "Honestly, Nevermind"—he should’ve done a club tour for that particular project. Not everything has to be an arena.
Cayla: It’s about tailoring it to YOU.
Kai: Exactly.
Cayla: So I want to know more about your talent management work. You said your clients come with wish lists—how does it actually work?
Kai: They’ll come to me with goals, or I’ll help them figure those out. Then I deep dive—check socials, past partnerships—and I come back with a plan. Post this many times, tag these people, host this, attend that. We check in every three months and adjust.
It's a mutual relationship. I've learned a lot: you can’t be an amazing manager with a bad client. If they don’t have the work ethic or drive, it won’t matter how hard you work.
Cayla: Right.
Kai: I’m lucky—my clients are great. I've been able to grow into different categories too—beauty, lifestyle, music, entertainment. It lets me flex creatively in new ways.
Cayla: I love that. A lot of creatives think getting a manager is the magic answer, but they’re not even doing the work themselves.
Kai: Exactly. People outsource too early. You need a manager when you’re missing opportunities—when your inbox is crazy, or you're so busy you can’t focus on the creative. My job is to clear the path so you can create—but you’ve got to actually create.
That’s when things can really move.
Cayla: What are the top three skills that make you a great manager?
Kai: One: being hella proactive—anticipating needs before they come up. Two: being super flexible and willing to work whenever. Opportunities don’t wait. Three: having a loving level of assertiveness—being cool with your clients but also holding them accountable.
You can’t let things slide, because when they don’t grow, they’re going to look at you.
Cayla: (laughs) True.
Kai: And yeah, basic office stuff matters too. I literally start every day with a typing test. (laughs)
Cayla: (laughs) I love that!
Kai: Gotta stay sharp.
Jason: Does managing others ever take away from your own life?
Kai: Nope. I’m super intentional about me-time. My clients know. I’ll work whenever, but I also make space for myself—whether that’s creative work or just personal stuff.
Cayla: So what’s on your wish list, both corporate and creative?
Kai: On the corporate side—I’d love to do more speaking: panels, workshops, college talks. People need to know there are creative careers behind the scenes too, everyone doesn’t have to be the star.
On the music side—I just want to drop more. I’m sitting on so much. I also want to get into production and engineering.