Why Issa Rae Embraces Being A Multi-Hyphenate Entrepreneur?

Jo-Issa Rae Diop, commonly known as Issa Rae, the HBO Insecure creator and actress, is making her mark in television, film, and now, music. Her ever-expanding empire is emblematic of her success as an entrepreneur—one who is empowered to disrupt Hollywood’s status quo. Within a few months into 2020, Rae is currently in the process of wrapping up production for the wildly popular and award-winning show, Insecure debuting again on April 12th and doubling down as lead actress in two feature films, The Photograph, and The Lovebirds. This is all while she’s ramping up her record label, Radio and serving as co-owner of the black-owned and operated Hilltop Coffee shop of her hometown, Inglewood, South LA. Many ask themselves, “How does she manage it all?”

Rae is inspired by providing accessible platforms to aspiring creatives and for her fans as well. She believes that the key to being successful is garnering multiple streams of income to create mobility and ownership. As a transitioning business owner, Rae is centering herself in enhancing her production company, Issa Rae Productions. Putting emerging voices on the map by creating additional opportunities for others—especially for those who look like her—is another main priority for her.

Forbes had the opportunity to sit down with Rae to discuss her upcoming projects, how she’s established herself as an entrepreneur, and where she sees her businesses scaling within the next three to five years.

What inspired you to expand your business empire from television to music?

“The opportunity and passion for both industries! With music specifically, it is part of every project that I do. Music plays such a vital role in my journey since my web series, Awkward Black Girl, and I also write music and, it inspires me in so many different ways. I’ve been approached with the opportunity in more of the talent side but that didn’t really suit what I wanted until the idea came to have a label. Then I thought this falls in line with exactly what we’re already doing on the television and film side, which is breaking new artists and writers into the music space and giving them a platform to excel. To have the opportunity to do that on the music side just excited me so much, and we already had the faculty in terms of my executive, Benoni Tagoe, who’s had a background in music, I just felt like he would kill this opportunity and run with it.”

How is your label, Raedio different from others?

“Providing our artists the opportunity to own their masters is a massive part of the difference. We are very artist-friendly during a time when there are a lot of artists that don’t trust music labels. Our music label provides our artists with instant access. Television shows are the new DJs in some ways, in terms of visibility and discovery of new music, and we’re able to plug our artists across those platforms pretty immediately, and that’s just a great way to showcase talent. We’re also looking for multi-hyphenate artists, so being able to sing and rap is one thing. Still, we’re also looking to build careers within the music industry and outside of it, which differentiates us from other labels.” 

How often do your two worlds, music and television, merge?

“They merge every day! Every edit of this season of Insecure is placing songs to make sure the episode is right. Beyond Insecure, I look to music to inspire my potential next project or to refocus while writing. Music is ingrained in my fabric.”

With two leading roles in the upcoming movies, The Photograph and The Lovebirds, share why audiences need to see diverse representation in mainstream film.

“So that you know it’s possible. That other people exist outside of you. For me, it was just so affirming to see people who looked like me on television. If I didn’t grow up in the nineties, I don’t know if I would think I could have the career that I have. I’m still in awe of the opportunities that have come my way, but I credit the people who came before me and showed me that it was possible. If being on-screen inspires some other little girl, that’s all that I’m here for. “

Why did you decide to partner with Hilltop Coffee + Kitchen to launch a coffee shop in Inglewood, Los Angeles?

“It was just a dream collaboration. I told my business manager that I wanted to start a coffee shop in Inglewood, and he said, “Cool, but are you going to grind the beans, like who’s going to run it?” Then I realized that I don’t know anything about running a coffee shop. Then he came a year later, and let me know if these guys who opened up a coffee shop in View Park and they want to open one in Inglewood, so our visions aligned, and I was just so excited to join them in expanding. I never run a coffee shop before, but I knew that I wanted one in my neighborhood to facilitate the community. I was just tired of having to leave my neighborhood to write and have an office because I can’t write at home. Most of my peers feel the same way, so it’s been such a success so far. I have a lot of fun meetings at our coffee shop, and it’s my second home.”

Where do you get your entrepreneurship drive and grit? What keeps you inspired to keep innovating and rebirthing yourself?

“I ask myself that every day. Whenever I’m tired, I’m like, “Why am I doing this? I should sit here and collect a check and be cool.” There’s just something about me that feels restless and that I don’t want to lose this window of opportunity that I have. Since I was younger, I loved to stay busy. My mom always used to say, “You’re bossy, and you can’t sit still.” I have lived up to that. She was just forming my identity. I guess I blame her.”

Why is being a black woman entrepreneur important to you? What have you learned over the years being a businesswoman and owning your own production company?

“I’ve learned that black women have been running things for a while. We don’t necessarily get the credit, but there are a lot of black female entrepreneurs. I’m proud to be one of them, and I think it’s important to showcase that. We do a lot and juggle a lot always, and which is expected of us, but it’s also important to realize that this is an actual skill. We are good at this, we are doing it very well and have been for years.”

How can other women empower themselves to launch their businesses and take their careers into their own hands?

“It starts with you having a pep talk with yourself. “Are you ready to do this? Asking yourself, “What is holding you back?” For me, it came down to differentiating what I didn’t have with what I had, which allowed me to start because I kept saying, “I can’t do this because I don’t have this.” Then it just became a matter of stopping the excuses and making it happen. I also wouldn’t be where I am if I didn’t have an honest and supportive friend and, of course, family members who asked the right questions. You have to be practical and have some plan in mind, but you also have to leap.” 

Where do you see yourself and businesses growing in three to five years? 

“My knees are tired! For me, it’s just getting to a place where I can sit back and let my leaders lead. I’m always going to want to invest from a distance, but I want to be able to have my music partner, Benoni, to taking control of Radio and weighing in. That pound cake verse that Jay Z has where he talks about how his associates have made billions because he’s paved the way for them is “goals” for me. It’s not even from a monetary perspective; it’s really about ownership. I think the more we create those pipelines for black women to continue to own, then the more successful and rooted we will be in our neighborhoods.”


Photo Source: Getty Images – Forbes