Underneath the actress’ insecure comic persona lies the fearless heart of a serial entrepreneur. She has parlayed a film and television career into a jewelry collection, a haircare company, a Prosecco brand—and counting. A portrait of a modern renaissance woman.
By Maggie McGrath, Forbes Staff
ON a bright September afternoon in the middle of New York Fashion Week, Issa Rae is sitting on a rooftop patio at Soho’s 11 Howard Hotel showing off her latest project: a 22-piece jewelry line produced with Cast, the San Francisco–based fine jewelry business. The collection—called “Braeve,” a play on her last name—marks a new chapter in her life as an actress, producer and entrepreneur. She is finally creating something tangible.
“Even with [my TV show] Insecure, I can’t hold it. Other people own it, and all I have is I know that I made it,” the 40-year-old Rae says. “Whereas this comes from me. Someone can wear it. I’m wearing it, and it represents me in a way that I think is less fleeting.”
Her career has been anything but ephemeral: In 2011, Rae, then a cash-strapped office temp worker, created the YouTube series The Misadventures of Awkward Black Girl. She crowdfunded more than $56,000 to finish its first season, then partnered with Pharrell Williams to produce a second. Three years later, HBO greenlit her next series, Insecure, which continued her awkward adventures. The show, which ran for five seasons and rang up multiple Emmy nominations (including Outstanding Comedy Series and Outstanding Lead Actress) led to an estimated $40 million, five-year deal with Warner Bros. Discovery that included first-look rights to Rae’s movie ideas.
Today, Rae remains one of Hollywood’s busiest multihyphenates, though she prefers the title of producer. (“Producers make things happen,” Rae said at the 2024 Forbes Power Women Summit.) She has built a flywheel of businesses—many with Rae puns in the names—including her production company (Hoorae), a music label (Raedio) and a pun-free talent management firm (Color Creative) that she launched in 2014. In 2020, she became co-owner of the hair care brand Sienna Naturals, cofounded by her sister-in-law, Hannah Diop, which will launch in nearly 200 Sephora locations in 2025. She also has a Prosecco brand, Viarae, that she developed with E.&J. Gallo Winery, the $5 billion wine behemoth. And she’s an equity partner in Hilltop Coffee, the South Los Angeles coffee chain that Rae has helped expand into Inglewood, Eagle Rock and Downtown L.A.
Despite her budding empire, the woman who played President Barbie in 2023’s Barbie insists she doesn’t have a master plan. “It happened organically, and it happened because these were things that we were all already doing,” she says. Her music label, for instance, grew out of her own music supervision on Insecure. Hoorae’s marketing business was born from her desire to take control of the many ad campaigns she was being asked to do. “For me, it was just about formalizing it and building intention around it.”
Mo Ivory, director of the Center for Entertainment, Sports and IP Law at the Georgia State University College of Law, gives Rae more credit than that. Last year, Ivory taught a law class about the structures of Rae’s business deals and says that compared to other performers her students have studied for the class—including Rick Ross and Ludacris—Rae has never compromised her creative control in exchange for a leg up in Hollywood or a bigger check. “Even though Issa will admittedly say she’s an awkward Black girl, she’s also very savvy. And has been from the beginning,” Ivory says. “She’s always willing to walk away from a deal that’s not right for her. And I think that speaks a lot to the respect she has and the integrity she has for her creativity.”
Rae often attributes that creativity to her upbringing. The middle child of five siblings born to a pediatrician father and schoolteacher mother, she grew up in Potomac, Maryland; Senegal (where her father is from); and Los Angeles. Rae remembers childhood dinners at which her mom would make up fun games like “Don’t Laugh and Smile.” The objective: Be the last person at the table to keep a straight face—which meant dinnertime was essentially a comedy workshop.
In high school, Rae originally wanted to follow in her father’s medical footsteps but fell in love with theater instead. She graduated from Stanford (with a degree in African-American studies) and, after a brief stint in New York, returned home to Southern California to launch Awkward Black Girl.
Yvonne Orji, the comedian who starred as Rae’s best friend in Insecure but who is also real-life friends with her, says the secret to Rae’s comedy lies in her ability to find humor in the “minutiae of every day.” She also credits Rae with an innate ability to take risks and give opportunities to unrecognized talent that Hollywood doesn’t always see or want to invest in.
“I think about the opportunity she gave me. Now [producers] will say, ‘We really want a Yvonne Orji type.’ And I was not a ‘type’ 10 years ago!” Orji says. “She will always give someone the alley-oop. It is up to them to slam-dunk it.”
Rae also understands that not all projects can be a slam dunk. She says her latest film, One of Them Days, starring Keke Palmer and SZA, took seven years to come to the screen. “We were able to make that happen, but that won’t happen again unless it’s successful.”
And despite all the “Rae” puns in her business ventures, she’s focused on building brands that could go on without her. It’s why Issa Rae Productions became Hoorae: “ ‘Hooray’ is just a celebration,” she says, “and while it has my name in punny form, it could still live beyond me.”
That same instinct is also what drew her to add “jewelry designer” to her every-growing list of job titles. “Cast is the most legacy-building collaboration I’ve ever done,” she says. “Storytelling is forever, make no mistake. But sometimes the stories get detached from the storytellers; the best stories do. This still feels . . . tangibly finite.”