AWK WARD AND UP WARD

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 in the 40-year-old Rae,” she 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.
image [https://cdn.magzter.com/1369322608/1740409964/articles/MfpyR5a9X1740484127622/1472612177.jpg]
Game On
"She will always give someone the alley-oop," says Rae's friend and Insecure costar Yvonne Orji (right). "It is up to them to slam-dunk it."
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 she students have studied—like 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 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 l...