From TV to Music Mogul: How Issa Rae Is Giving Artists A Leg Up

There’s a line out the door at Hilltop Coffee + Kitchen in Los Angeles’ Inglewood neighborhood, but Issa Rae, the creator and star of HBO’s Insecure, strolls right past it, nonchalantly making her way in through the crowd. “I love working out of coffee shops. It always bothered me that I had to leave my neighborhood to do that,” says Rae. So a year ago, when she purchased a building for her company, Issa Rae Productions, she decided maybe she should open her own inside it. Her business manager “was like, ‘Cool. Are you going to be serving the coffee? When are you going to have time to do that?’ ” Rae says with a laugh. So she partnered with Hilltop’s owners for this location, less than two miles from both her office and The Dunes, the apartment complex where her character, Issa Dee, lived for the first two seasons of Insecure. “The vision for it was always to service communities of color that don’t have these spots,” continues Rae, settling into a broken-in leather couch. “It is a way to foster networking, collaboration, and it’s a community space that’s ours.”

Rae, who is 35, grew up in Los Angeles’ affluent black neighborhood View Park, and her love for her city shines through on Insecure: She frequently shoots at classic Angeleno spots like the now-closed music venue Maverick’s Flat and late-night diner Swingers, and she chooses songs by local artists like Derrius Logan and Overdoz to bring the show’s narrative to life. Insecure’s music synchs — from Leikeli47’s “Girl Blunt” in the Coachella episode to Daniel Caesar’s “Blessed” in the final scenes of season two — have become its trademark, often directly shaping how Rae will write a scene.

On this morning at Hilltop, Rae is wearing a sweater printed with the phrase #TellBlackStories. It could easily serve as a thesis statement for every Rae venture — including her newest, a major foray into the music industry. In October, Rae and her longtime business partner Benoni Tagoe launched Raedio, which Tagoe describes as a “five-vertical” audio content company comprising publishing, live events, music supervision, a music library and a label that’s a joint venture with Atlantic Records.

“I would watch [Insecure] every week just to hear what she was using,” says Atlantic chairman/COO Julie Greenwald, who had seen several of her own artists, like Janelle Monáe, featured on Insecure. All of them, says Greenwald, saw increased attention on Shazam and streaming platforms following an episode’s airing. “Her usage of music is extraordinary,” Greenwald says of Rae. “It’s not just a five- or 10-second blip. She lets the music really set the stage and be part of the narrative.”

“We talked to every label, literally,” recalls Tagoe, now Raedio’s president. “We felt like a hit artist. Ultimately, we decided to go with Atlantic because the team over there understood the vision.” That West Coast president Kevin Weaver had handled the Fast and the Furious and Greatest Showman soundtracks — a realm Raedio hopes to break into — made Atlantic a particularly attractive partner.

When Greenwald told her team of a potential meeting with Rae about a new label venture, they “lit up,” recalls Greenwald. “I felt like I had this crazy obligation to deliver or they were going to kill me.” She was confident that Rae would “create her own path forward and use her resources and her outlets to help break and develop artists.”

Rae — who wants to develop artists who not only perform but produce, write and direct for various media — was impressed by Greenwald’s immediate trust in her vision: “To have Julie Greenwald herself really vouch and ride for us felt like an asset in a major way.”

Before arriving at Atlantic, Tagoe and Rae found that few labels were ready to embrace their approach, including giving artists ownership of their masters and providing signees with health care. “Most major labels can’t offer [health care] because they have hundreds of artists,” says Tagoe, who formerly worked for AEG and, for several years, handled day-to-day management for the Jonas Brothers. “We’re just doing what makes sense. If it is a true partnership and artists are doing things for you, you should be providing things for them.”

The other businesses under the Raedio umbrella will, Tagoe and Rae expect, financially support the label. The audio content company will focus on music supervision — “a natural next step,” says Rae, given her experience with Insecure. That vertical will be overseen by Raedio’s first acquisition, music supervision company Bonfire Collective, and will provide in-house music supervisors for Issa Rae Productions and for already greenlit projects on Netflix, Hulu, HBO and Starz (on the latter, the upcoming strip-club-set series Pussy Valley).

“I had been looking for an opportunity to grow my business because the projects [we’ve] been doing have gotten bigger and more demanding,” says Bonfire founder — and, now, Raedio’s head of music supervision — Stephanie Diaz-Matos. During its five years in the industry, Bonfire has worked on music-centric projects like Netflix’s The Get Down and rom-com Someone Great, which helped catapult Lizzo’s “Truth Hurts” onto the Billboard charts.

“The truth of the matter is that music supervision is a good ol’ boys club. At the end of the day, people have their favorites,” says Tagoe. “So it was great to tap into a company that already has the relationships and the experience. It no longer becomes a question of whether or not our company can do the job.”

Issa Rae Productions will now use Raedio music supervisors for projects that were previously contracted to third parties. (Tagoe adds that they’ve lined up 10 to 15 TV projects for 2020 alone.) “I love [scriptwriter] discovery and kind of plugging them into these existing pipelines that they otherwise might not have had access to,” says Rae. “We’ve been able to do that for fairly unknown, unrepresented writers to get them their first TV show, their first features, etc. So I’m excited to be able to do that on the music side with qualified people.”

While its live events division is still in development, Raedio has paired up with Kobalt to collect its publishing revenue and manage its music library, which will mainly include royalty-free tracks for film and TV use (pricing will depend upon licensees’ needs). “In terms of aligning with someone who bridges all her companies together, this is a first for us,” says Kobalt chief experience officer Jeannette Perez, who explains that Kobalt will supply songwriters and producers to create material for projects and pitch Raedio’s library to other brands and music supervisors. Raedio will pair Kobalt creatives with label artists at writing camps geared toward producing music specifically for shows (it has already done so for Insecure and Pussy Valley) that can then be added to the Raedio library.

“It makes a lot of sense for them to want to start a library,” says Perez. “They are equally involved in film and television and making sure that they can bolster that creative with music that is authentic to the kind of visual they are creating, but then it can also be used for other companies, other studios, other supervisors. This library is going to be high-quality, full songs made by creators who are authentically making music in multiple genres.”

It’s just one element of what Rae and Tagoe hope will become a uniquely all-encompassing music service that provides opportunities traditional labels can’t for creators who are often overlooked. “In trying to sign artists their main question is ‘Why you?’ That’s an important question to ask,” says Rae. “All I can say is ‘I believe in you. You get to experiment with us. We can plug you into way more places than your average label.’ ” Much like Rae’s show and even the coffee shop where we’re talking, Raedio will, she hopes, organically fill in a gap both in the industry and her community. “I want to prioritize female artists, L.A. artists and black independent artists,” says Rae. “That’s what I’m always searching for.”

You were a presenter at the Grammys, and you got to give ­Tyler, The Creator the best rap album award. What was that night like?

Well, that particular day I was excited to be at the Grammys, but Kobe [Bryant] had just passed, and it was at the Staples Center [home of Bryant’s team, the Los Angeles Lakers]. I was crying all day. I just felt like, why am I here? But I was happy that Tyler won, because I love him, and I love that album [IGOR]. His speech after getting it was amazing. It was a nice little L.A. moment. I didn’t get to tell him this, but one of his songs is opening our fourth season.

After his win, Tyler said that he felt the word “urban” is a politically correct way to say the N-word — essentially that it’s an umbrella term used to lump black people into one category. Do you agree?

One hundred percent. On the film and television side too. It’s an ugly word. I think he articulated it beautifully. It’s another way of saying “This is a n—er show. So let’s market it to the n—ers,” and that’s it. It’s very insulting. That comes about because you have people in charge who very much think along those lines. It’s vague, but everybody knows what it means.

How did you decide to start your own label?

I had been approached in the past by a couple of different labels to be an artist, and I’m not [on Insecure, Rae raps in character]. I’ve got no intentions of doing that. Then somebody else put the bug in the ears of me and other people around me about starting a label. I was like, “That seems more my speed.” I had those conversations internally like, “Hey, can we do this? If we make this happen, do we have the support staff to make this a legitimate thing?” And everybody was onboard.

What made you feel Benoni should be Raedio’s president?

He worked with an extensive number of artists in the past before he started working with me. Beyond that, he’s just very smart, very business-savvy. He’s always thinking about the future in a way that I really admire. He has been by my side for a very long time, and he has a great eye for artists and talent, in terms of building businesses around talent.

Is there a certain type of music you’re especially interested in?

I’m open. I know what I like, but that doesn’t mean we wouldn’t seek out artists [in all genres] who are just phenomenal. Ultimately, because I want Raedio to live beyond just me, we have to be smart, as we grow, about expanding to other genres that I don’t necessarily fuck with. A good song is a good song. A good artist is a good artist.

How involved will you be with the label day-to-day?

I am 100% involved in [finding artists and in synch placement]. I know that I am not a musician and I try to trust artists. All I can do is give feedback. It is very collaborative. Sometimes I’m like, “Oh, we got to sign this person!” and they’re like, “Ummm, no.” For our first artist, [pop/R&B singer] Teamarrr, I am listening to everything and I am giving my opinion about everything. I want her to succeed.

Has the conversation around Taylor Swift fighting for her masters shaped your decision to let your artists own theirs?

Absolutely. That was something that was really important in our negotiations with Atlantic. We want to be artist-friendly. That’s a huge part of being able to have longevity — to have a stake in your own career is to own your masters. I understand, especially when you become fucking Taylor Swift, you want some sort of ownership over your work. But coming from the TV side, I don’t own Insecure. HBO owns that at the end of the day. I have to have my own distribution arm to be able to own my work. I think now artists are so much more hip to the fact that “Oh, I don’t ever have to sign with anyone unless I absolutely need the money,” and even then it’s easier to negotiate.

Why did a music supervision company feel essential for Raedio?

It is the most direct way to get awareness [for artists] and for [new music] discovery. It’s a way to make some cash without any strings attached. My younger brother is a musician and he complains about how long it takes to get paid. Synchs are potentially lucrative and lead to people wanting to maybe see you perform live, which is the other bread and butter of the industry.

Right now you’re in the thick of editing season four of Insecure, including making music edits. What’s that process like?

That’s the best part to me — placing songs. Today I have to watch the seventh episode, and every time I watch an episode I’m on pins and needles. If the music’s not right, I’m automatically not going to like the episode. So I always want to send notes like, “Hey, let’s try this. Let’s try this performance shot. Let’s change the song to this.” Music is just so important to the storytelling.

Is there a particular synch in Insecure that’s a personal favorite?

Kendrick [Lamar]’s “Alright” [opening the first scene of the series]. It draws you in, but I was like, “We’re going to have to replace this because by the time the show comes out the song is going to be old and I want something new and fresh to represent L.A.” We did the sound mix and we saw it for the first time on a big giant screen and by the end I was like, “I miss ‘Alright.’ ” Kendrick’s from L.A., it embodies the spirit of the show, it starts it off with a bang and you feel good going into it. It represents the relationship between Issa and [her best friend] Molly in a really good way. I pulled the [HBO] exec to the side and was like, “How much is it going to cost? I know we opted to replace this. Can we do it?” And they ate that money up, but we got “Alright” back.

You’re currently starring in two movies, The Photograph and The Lovebirds; you’ve written a New York Times bestseller, The Misadventures of an Awkward Black Girl; you run a production company; you co-own a coffee shop and, now, a music company. Is there a particular mogul you’ve modeled yourself after?

I always say that I model myself after Diddy, Ellen and Oprah: Oprah for being able to diversify her businesses and being a major influencer in that way; Ellen for being able to make a business out of being herself; and Diddy for his business acumen in expanding beyond hip-hop. I’ve looked to them in terms of ways to make my own imprint.

Where do you get your business acumen from?

Being on the internet. When I just wanted to put out some shit that I had written, and then being forced to market it and then build a team around it and then having ideas about promoting it. Even from a young age, my mom used to call me bossy. Only now do I realize that I wanted to be that. I wanted to be a boss because, why the fuck not? I liked feeling like I was working or in business. I liked feeling like a leader. And it is not always fun, by any means, but there’s an element of accomplishment that I feel in executing projects.

This article originally appeared in the Feb. 15, 2020 issue of Billboard.