American actress and writer Issa Rae has crafted a path for herself that goes beyond traditional Hollywood boundaries. From her breakout YouTube series The Misadventures of Awkward Black Girl to her Emmy-nominated HBO hit Insecure, Rae has evolved into a media mogul with a business empire crossing entertainment, beauty, and community-driven ventures, according to Forbes.
The actress has achieved these feats through a relentless focus on ownership, creative autonomy, and building brands that will outlast her own stardom in Hollywood.
Rae’s journey began in 2011 with a crowdfunded web series that resonated with audiences craving authentic Black narratives. By 2020, she would transform into a Hollywood powerhouse, leveraging her success into ventures like Raedio, a music label prioritizing artist ownership of masters, and Hoorae, her production company consolidating film, TV, and marketing verticals. Today, her portfolio includes: Sienna Naturals, Viarae Prosecco, Hilltop Coffee + Kitchen and Braeve Jewelry, as per Forbes.
Sienna Naturals is a Black-owned haircare brand co-founded with her sister-in-law, set to launch in 200 Sephora stores in 2025. Viarae Prosecco was launched in partnership with E.&J. Gallo Winery. It blends her love for celebration with luxury branding while Hilltop Coffee + Kitchen is a community hub in Inglewood, which reflects her commitment to investing in underserved neighborhoods. Braeve Jewelry, on the other hand, is a 22-piece fine jewelry line with Cast, designed to leave a tangible legacy.
Rae’s empire isn’t just about diversification—it’s about retaining power. Unlike many creators, she refuses to sacrifice creative control for financial gain. This belief extends to her talent management firm Color Creative, which amplifies underrepresented voices; it also extends to her collaboration with American Express to fund Black entrepreneurs.
Her ventures also address systemic gaps. For example, Rap Sh!t, her Max series canceled in 2024, was a case study in vertical integration: Hoorae developed the show, Raedio handled music, and her marketing agency Fête secured product placements. Though axed amid industry cutbacks, the project exemplified her model of uplifting new talent—like first-time showrunner Syreeta Singleton—while challenging Hollywood’s retreat from diverse storytelling.
Rae’s success hasn’t shielded her from industry turbulence. The 2023 strikes forced layoffs at Hoorae, and cancellations like Rap Sh!t and Sweet Life: Los Angeles highlighted what she calls Hollywood’s “backsliding” on diversity pledges. “There aren’t a lot of smart executives anymore,” she told TIME, criticizing conglomerate leaders for prioritizing “universal” stories over culturally specific narratives.
Yet Rae remains undeterred. She’s developing two new HBO projects, including a corporate comedy and a show set in an “alternative present,” while planning a studio campus in South L.A. to foster local talent.
Her resilience stems from a philosophy of “passion over plan”: “These ventures happened organically because they were things we were already doing,” she said.
Legacy Over Labels
Rae’s ultimate goal is to create institutions that endure beyond her. The rebranding of her production company to Hoorae and her focus on scalable businesses like Hilltop Coffee underscored this vision. Even her Prosecco line and jewelry collection are designed as legacy projects: “Storytelling is forever, but this feels tangibly finite,” she said.
