CEO-LIKE:
ISSA RAE’S
GREATEST ROLE
WRITTEN BY: ALISA GUMBS | PHOTOGRAPHER: TAYO KUKU JR. | VIDEOGRAPHER: DONAVAN JOHNSON
THE ACTRESS, PRODUCER, AND
SERIAL ENTREPRENEUR OPENS UP
ABOUT HER APPROACH TO BEING THE BOSS, LEADING AUTHENTICALLY, AND
EMPOWERING HER TEAM
Even if she hadn’t been wearing bright orange head to toe, you could have seen Issa Rae coming from a mile away.
She walked up to the podium at the Black Enterprise Women of Power Summit with a megawatt smile and a confident stride. The eyes of 1,800 Black women were transfixed on her as she grasped the tiniest piece of paper, jotted with handwritten notes, and launched into telling a story as only she could—with her signature dry humor, hilarious facial expressions, and impeccable timing.
In trademark fashion, she turned an everyday story about an awkward business meeting into a comedy gold mine.
Rae’s credentials as a skilled storyteller are unquestioned, from her award-winning web series The Mis-Adventures of Awkward Black Girl to her hit HBO show Insecure. And though she wears many hats—both in front of and behind the camera—actress, writer, director, and producer among them—her most impressive role is businesswoman. Just check out her ventures:
Doing what nobody else does
Creating has always come naturally to Rae, and she sees being an entrepreneur as an extension of that. “I love to create things from the ground up, whether that’s telling stories, whether that’s projects, and businesses in particular,” she says.
“For me, I ask: one, what’s missing, and two, how can I fill that void? If it’s an existing establishment or an existing venture, how can I make it better? But there’s something about building things from the ground up that just feels satisfying to me.”
Like many aspiring entrepreneurs, Rae wasn’t sure that she could turn her vision into a profitable and sustainable enterprise, despite her talent and ambition.
“I’ve always wanted to be in the business of us, to tell our stories. But I never knew if I could be successful at that, if that was something that I could make a living off of, if there would be longevity,” Rae says. “I didn’t know that I thought it was possible.
Making it happen in Hollywood, where so often people get their foot in the door by knowing the right people or being in the right place at the right time, was even more daunting. The digital revolution gave Rae the opening she needed not only to break into the industry but to believe in the possibilities.
In building her ventures, Rae’s been intentional about reimagining how business is done.
“There are traditional ways, there are ways that sometimes feel archaic, of running businesses. Even in thinking about what a CEO is, there’s a specific image in my mind of what those people look like, what their interests are. And it doesn’t necessarily always reflect us,” she says.
Instead, she approaches being the chief executive in ways that feel authentic. For her, that means “being comfortable with myself, moving with integrity, being transparent, and constantly being open about learning,” she says.
“I don’t think I could do my job if I’m not authentic to myself. Even in creating businesses, I’m always thinking about what the most real version of me needs and wants to say. And that’s how I operate,” she says. “I think if I were a false version of myself or showing up otherwise, it wouldn’t work.”
Having her own production company positions Rae to achieve that long-held goal of making sure Black audiences are served.
“For me, the No. 1 intention and focus is us,” she says. “To have a company, several companies, that consider us first and not as a stepping stone or as a way in feels like my particular purpose.”
“It’s disheartening when you’re trying to tell stories that you feel are authentic to us, that we crave, that we miss, that we know exist, and to have a power-that-be tell you, ‘No, we’re not going to fund it.’ I wish that was a story of the past, but it still happens now,” she laments.
“But it’s more heartening to know that we are in more positions of power,” she continues. “And we’re putting our powers together to ensure that they don’t shut us out anymore.
There’s no better insight into Rae than someone who’s known her her whole life.
“Despite our personal relationship going back to birth—with us being siblings—our professional relationship didn’t really start until around 2020,” says Malick Diop, one of Rae’s older brothers and the chief financial officer at HOORAE.
Diop is putting his Wall Street background and extensive experience in mergers and acquisitions, debt and equity capital raising, and risk evaluation and mitigation to use for the fiscal stewardship of his sister’s company. He started his career at JPMorgan as an investment banking analyst before becoming a senior credit analyst with AIG and a managing director at Morgan Stanley.
As the CFO, he helps HOORAE and each of its verticals with budgeting and forecasting, identifies capital needs, and helps set and execute overall strategy.
Being part of Rae’s team felt like a no-brainer, Diop says: “I would describe Issa as a practical visionary, meaning she has very large and clear ambitions, coupled with the determination, work ethic, and willingness to trust and empower others to help her turn her visions into reality.”
“It’s pretty rare to see a creative genius in her own right that is simultaneously selfless and committed to uplifting other voices and uplifting her community.”
Like Diop and many of the company’s executives, Monique Francis signed on for one simple reason: “I believe in Issa’s vision for HOORAE and the impact she wants to have in the world.”
Francis, a purpose-driven marketer with expertise in helping brands connect to audiences through culture and storytelling, was formerly a client strategist at MediaLink, part of United Talent Agency. Before that, she held several marketing and brand consulting roles at Creative Artists Agency and Synapse Group, a Time Inc. company.
“In my previous role at UTA, I represented brand clients looking to drive their businesses through entertainment and culture. We were constantly pitching Issa as the ideal partner, as one of the most relevant, multifaceted, and influential figures in culture,” Francis says.
Now, as the person responsible for marketing strategy and operations across HOORAE’s divisions, including building its portfolio of brands, expanding its collective reach, and partnering with other companies to grow its business, Francis sees Rae’s influence firsthand.
“Though she has a demanding schedule as a multi-hyphenate creator and entrepreneur, she is not just a figurehead of her business. She is involved,” Francis says. “She cares about what happens at her company and the people that work there.”
That investment in people is one of the things Francis is most impressed by.
“In an industry where we often have to have already done the job to get the job, Issa is willing to take a chance on people and throw her support behind those she believes in,” Francis says. “She has not only changed lives, she has changed industries and will continue to do so for years to come.”
Taking a chance on people is a recurring theme in Rae’s approach to business.
“I’ve known Issa since 2011. I was a big fan of her web series, and I tried to partner with her to redevelop it for TV. Issa turned down the chance to work with me at the time, but we stayed in contact and worked on a few projects together,” says Montrel McKay, now Rae’s president of development and production, who works with her to build out HOORAE’s film and TV slate and produce the projects that are greenlit to production.
McKay began his career in entertainment at the talent agency WME, where he helped establish non-traditional content distribution strategies. He later became the vice president of development at production company Electus, where he developed series for broadcast, cable, and streaming platforms. He was also a senior vice president at Apex Entertainment Ventures, a subsidiary of Publicis Groupe, leading their foray into original content investment.
McKay is grateful for the opportunity to collaborate with Rae over the past five years: “Issa’s a creative genius who leads with integrity, and she works harder than anyone else that I know in our business.”
“She is open-minded and doesn’t have an ego. She believes that she can learn from anyone and only cares about finding and producing the best ideas. She does not see limits for herself, and it inspires everyone around her to think and execute at the highest levels,” says McKay, whose shared vision with Rae is to grow HOORAE into the “biggest and most revered” production company, and eventually indie studio, in the world.
McKay isn’t the only one who can trace his business relationship with Rae back to her groundbreaking web series.
“Issa and I had mutual friends, and when I saw what she was building with The Mis-Adventures of Awkward Black Girl, I sent a long email detailing all the things I felt I could bring to the table. We soon met up to discuss, and the rest is history,” says Benoni Tagoe, now the president of Raedio.
Tagoe is a serial entrepreneur with more than a decade of experience building businesses around creatives and influencers. He started his career as an assistant to the Jonas Brothers, eventually becoming part of their day-to-day management team.
He went on to produce content for TV and new media platforms and started his own management and consulting company, The Bizz Plan.
Now he serves a dual role as the head of business development for what used to be Issa Rae Productions (now HOORAE) and the president of Raedio. “We call it an ‘audio everywhere’ company because we aim to exist wherever audio does,” he says.
“Issa is an incredible mix of creative meets businessperson,” Tagoe says, echoing her other executives’ praise for her willingness to take risks and the trust she places in the people around her.
“It’s not every day that you meet up with a generational talent, let alone get the opportunity to work with them. Issa Rae has a perspective and voice that is undeniable.”
Rae isn’t just (famously) rooting for everybody Black. Since the beginning, she’s put on for her city—reppin’ Los Angeles to the fullest.
Rae tapped fellow Angelino Kaylin Cotton as her chief of staff, a role in which she streamlines procedures and enhances collaboration and communication between HOORAE, Raedio, and ColorCreative.
Cotton first honed her millennial approach to leadership by managing employees and retail locations for companies such as Sketchers and Target before taking on positions at Live Nation, specializing in internal diversity, equity, and inclusion communication and programming, and at Shonda Rhimes’ media company, Shondaland, building out the company’s brand guidelines and events.
“Issa is the definition of a revolutionary powerhouse. She represents things that I feel mirror who I am, such as being a Black woman from South L.A., one who has worked to build a successful brand and give people who look like her opportunities that they may have never imagined,” says Cotton, who has had plenty of experience being the youngest, one of few women, and singular Black person in the room.
“Our collaboration has been amazing. Issa empowers me daily,” says Cotton, who serves as adviser, confidant, and sounding board to Rae as the CEO and the entire executive team. “That makes it so easy to go through my days knowing that I have someone who is supportive and, importantly, trusts me to execute.”
Surrounding herself with powerful women is another secret to Rae’s success.
“Women are my support system, the source of my confidence, my inspiration. I love women. I love being around women. I love laughing with women. And most rewarding of all, I love working with women,” Rae says.
And with Rae calling the shots, the days of women being left out of the decision-making are done: “It’s a question that I frequently ask myself whenever I walk in a room: Where are the women? Where are the Black women? Now I’m in a position to make sure that they’re there.”
Joining Rae in her mission to make sure women are well-represented in the entertainment industry is Talitha Watkins, president of ColorCreative, the management and production company that focuses on representing women and people of color and that is looking to change the way the entertainment industry does business with both groups of creators through ownership, commercial success, artistic fulfillment, and visibility.
Formerly a motion picture agent representing producers, writers, directors, and actors and a cultural executive at leading entertainment and sports agency Creative Artists Agency, Watkins has also served as the vice president of multicultural marketing at Universal Pictures and as an assistant general manager with Telepictures Productions.
Even though they didn’t meet until 2019, Watkins has been “creatively aligned” with Rae since the first season of her web series. “I loved her storytelling and her hustle to deliver content for her growing audience,” she says.
Watkins says Rae is a “natural-born leader” who has been “steadfast on her mission of representation.”
“Her commitment and consistency are two of the reasons that I chose to align with her in my career,” says Watkins. “I am a true fan of her work. And, after getting to know her better, I am an even bigger fan of her as a human.”
CONSTANTLY EVOLVING
Despite all the things Rae has already accomplished in her career and with her businesses, she doesn’t feel like the work of trailblazing is behind her … yet.
“I feel like, in so many ways, I’m still having to clear a path and prove myself over and over again. And I’m willing to do that,” Rae says. “You can’t take that position for granted at all.”
Unsurprisingly, her team is in alignment, recognizing their successes but acknowledging the work still to be done.
“The company has already grown so much, yet we’re just getting started. We collectively have big aspirations for continuing to build HOORAE’s brands, expand into new areas of business, and grow our incredible team,” Francis says. “I feel like I’m strapped into a rocket ship that has just taken off.”
“We want to continue to be status quo breakers in business,” Tagoe adds. “It has been one big upward trajectory, and I don’t see it stopping anytime soon.
”The ride so far has certainly been bumpy at times, but Rae has handled it with perseverance and grace and, always, with laughter.
“The journey to be fearless in the pursuit of what I wanted to do was absolutely terrifying. It could be such a public failure. And that’s honestly what motivates me.
I don’t want to be a part of anybody’s group chat,” Rae jokes. “So, I just have to move correctly.”