The Managers on the Front Lines of Rap’s Generational Shift
Music managers don’t exactly have a sterling reputation in the broad pop-culture consciousness. Casual fans usually only hear about them when there’s serious drama (either personal or financial), and they’re frequently seen as trying to cynically swoop in on the New Hot Thing with only a cursory interest in the art they’re making. But nowadays, with artists being visible 24/7 and the industry undergoing tectonic shifts seemingly every few years, the role of a manager has changed, and so have the people doing it.
It’s not uncommon for people in music to straddle multiple roles — producers and A&Rs, singers and songwriters — but an increasing number of rappers have decided to try their hand at management. In most, but not all cases, these figures have put their own artistic career on the back burner to focus on developing new talent, sometimes to cultivate a more prosperous music scene in their beloved hometown, and sometimes to work in vastly different subgenres than those they could as vocalists.
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Now, the complicated tensions between a budding superstar and their team play out in real time. XXXtentacion stabbed one of his early managers over a financial dispute, and then the manager talked about it in an AMA on the XXX Reddit. First Access Entertainment, which managed Lil Peep at the time he passed, is facing a wrongful-death lawsuit filed by the late artist’s mother, Liza Womack. Last year, Chance the Rapper sued his ex-manager Pat Corcoran, alleging that his “inattention, incompetence, betrayals, and competing business direction” adversely affected Chance’s career. A-list artists have mobilized fans to go after industry figures and publications, and it feels inevitable the same could happen to an ex-manager.
“To me, the managerial space went from being a manager to a GM. Back then, you could just be the fucking manager at McDonald’s, making sure the burgers was in the thing and you’re cool,” says Barry Hefner, co-founder of the management company and label SinceThe80s, which boasts J.I.D. and Earthgang as clients. “Now, you’re pretty much the GM of a team.”
“I just think it’s so funny that there is someone sitting at home who doesn’t work in music that cares enough about this stuff to know who the EVP of marketing at RCA is.”
Managers have always leveraged their relationships around the industry, but now, Hefner says, that is crucial in figuring out how to position new talent. In the case of SinceThe80s signee SoFaygo, Hefner thought back to a decade ago when he was watching Travis Scott’s rise, and decided the pair would be logical partners. Faygo is now signed to Scott’s Cactus Jack label but retains management through SinceThe80s.
“The thing about it is you are the label. No matter how you want to look at this shit,” Hefner says. “Young manager, old manager, I don’t give a fuck. The same way that artists are now collaborating with other artists now more than ever, it’s the same thing with executives.”
Beyond how the day-to-day job is changing, managers are now having to contend with being public figures and drawing both interest and ire from fans online. Justin Lehmann, who runs Mischief Management and manages Aminé, posits that it’s part of the shift in music culture, alongside obsessing over sales numbers as a means of claiming that your favorite act is superior to their peers. In his mind, it’s not all that different from the way hardcore NBA fans use the moves of their team’s front office to prove they are better and smarter.
“That stuff has happened in sports, I think, for a longer period of time, but has now spilled over into music, where you have massive groups of people that care about the charts every single week and chart positioning,” says Lehmann. “I just think it’s so funny that there is someone sitting at home who doesn’t work in music that cares enough about this stuff to know who the EVP of marketing at RCA is, or whatever example [you choose].”
Alec “Despot” Reinstein is part of rap’s transforming new class of managers, but he admits he got into this lane of the industry as much to perform a kind of philosophical experiment as he did to bring out the best in young artists. “I never understood what management was as an artist, or why I needed it, or why anyone needed it,” he says. “I think that maybe I became a manager just to try to understand why managers exist, and I still don’t know why. I really don’t.”
The sample size is small, but Despot’s unconventional career fits the broader trend of artists who pivoted to management. Stat Quo, who declined to speak for this story, was a longtime signee to Shady/Aftermath, but never put out an album on the label before getting involved as Lil Xan’s manager. He also works with Cole Bennett, perhaps the most in-demand music-video director in rap today. Houston’s Chedda Da Connect, of “Flicka Da Wrist” fame, moved behind the scenes to manage Don Toliver (they even have a peculiar unreleased song together called “Avatar Booty”). Blog rap mainstay Mikkey Halsted serves as the manager for G Herbo — a union of two Chicago musicians whose art occupies different niches. Fee Banks, once a supporting player in Lil Wayne’s Sqad Up group, has become a pivotal player in the Louisiana music scene through his work with Youngboy Never Broke Again.
“I feel like a lot of artists from that era are the perfect managers,” Zeke Nicholson, SinceThe80s co-founder, said.
Halsted gives significant credit to his own former managers, No I.D. and Quality Control Music co-founder Coach K, for preparing him to work behind the scenes. His current roster includes a number of Chicago-based artists, including Herbo and versatile vocalist Tink, as well as rising singer Feather. One of his main goals is to create infrastructure in his hometown, which has always been rich in talent, but lacking in its own industry spaces run by veteran figures.
“We’ve got to look within to fix our situation. I feel like once we do that, we’ll be on the right path and be able to really start building the institutions that can help our people in a real way,” he says. “I can’t look for anybody outside of Chicago to do that, we have to do that.”
Halsted has been managing Herbo since he was 16, and acknowledges that working with artists that age presents its own unique challenges. The industry has had to deal with these more and more, as social media has made it feel like the average age of a famous rapper is notably younger than their counterparts 15 or 20 years ago. For these reasons, Halsted says the younger acts he ends up working with are usually Chicago-based, since he can connect with them more easily than other managers.
“I grew up in the ghetto of Chicago, so I can relate to them. You’ve got to have a certain skill set to be able to relate to those kids, everybody just couldn’t do it,” he says. “You could have a great business plan laid out, but you don’t understand how to really relate to them in a real way.”
Halsted, who has been candid about the negative aspects of his time on Cash Money Records, explained that he was never in a situation where he had all of his creative needs handled, meaning that he had to learn how to be self-sufficient, even within the label system.
“I’ve never been at a label where I could just depend on the label and they roll it out and do all that. No, we were hand-to-hand with it,” says Halsted. “Management and artists in that era had to be shoulder-to-shoulder many times. That prepared me for being able to manage a Herb or a Tink or everybody else that I managed.”
As Lehmann notes, artists moving into management feels like a logical extension of the rapper-as-mogul tradition that encompasses everyone from global business power players like Jay-Z to savvy label founders like Yo Gotti to more local and regional examples. Even though streaming and social media have made it possible for artists in the most remote places to reach a wide audience, getting hot in your city or state remains the preferred path for many artists and their teams.
“When I’m talking to new artists, I’m like, ‘You’ve got to build the interest. We could do everything that we could do. We could curate it, we could shoot the dopest video. We could use all the tricks. I can get you a video on the page with the director that has X amount of millions of subscribers already, but you still have to connect. The connective tissue from you to the streets still has to be relevant,’” Halsted explains.
While it’s easy to see why rappers can transition into management, the rapidly changing hip-hop landscape means there’s always a significant learning curve for artists setting out on this new path. “It sucks because most of this shit didn’t exist at all when I started making music – or none of it did,” Despot sighs. “It’s a little disheartening to see how A&Rs function now because a lot of is straight-up ‘Tell us this artist’s name, we’ll go and run the numbers and we’ll see what he’s doing on Soundcloud, what he’s doing on Spotify, on YouTube, whatever,’” Despot says.
For the last few years, one of his main artists has been Houston rapper BBY Kodie. A charismatic rhymer with a quietly menacing edge, Kodie feels like a perfect postmodern rap star, but Despot says he spent years beating down doors on Kodie’s behalf. He didn’t find a receptive audience in label execs until his flip of Kelis’ “Milkshake” went viral nearly two years after its initial release.
“I was taking label meetings and a lot of major labels were like, ‘This music is great. I like it. But the numbers aren’t there,’” Despot recalls. “And then the second ‘Milkshake’ went viral on TikTok, a lot of labels called me back and everyone was like, ‘Okay, let’s go.’”
Still, there can often be a disconnect between gaudy streaming numbers and how many of those casual listeners will attend a concert. Part of the role of an experienced manager nowadays is not just to affirm an artist for how far they’ve come, but to show them just how much farther they have to go.
SoFaygo scored massive viral hits like “Everyday” and “Knock Knock” before he turned 20, and his first free show in Atlanta was packed with thousands of hyped fans. That’s enough to have any young artist feeling themselves, so the SinceThe80s team knew it would be important that his next scheduled show should emphasize that he’s still scaling the mountain, not lamping at the top.
“Then he goes to Rolling Loud on the main stage and now he has to realize, ‘Damn, all these people might know my name but they don’t know my music. They might know one song or two songs.” says Hefner. “Being a new artist and touring post-pandemic is a completely different monster,” Nicholson adds.
Like most musicians turned managers, Despot’s own artistic output has slowed, though it hasn’t stopped. He said sometimes that makes his position guiding younger artists a challenge because he’s still thinking of himself as an artist. “It’s hard for me to operate as a manager because I still think like an artist and still am one,” Despot says. “Even walking into some major label meetings and having an A&R sit down with me and be like, ‘Yo, I was a huge fan when you were a rapper.’ And I’m like, ‘Fuck you, I’m still a rapper.’”
Historically, the manager has been seen as more aligned with the interests of the label than the artist themselves, part of the persuasion bloc that pushes them to never pass up on a lucrative opportunity, even if it’s deeply uncool. But that dynamic is upended when the manager knows what it’s like to be in the artist’s shoes and is willing to push back on their behalf.
“A label, they’re used to hearing from the artist ‘That’s corny. I don’t like that.’ But they hate hearing that from the manager because they’re like, ‘You’re supposed to be working with us,’” Despot says. “I’m not supposed to say the word ‘corny.’”
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