From Insecure to Investor: How Issa Rae Built Her Empire

From Hilltop Coffee to Unrivaled, the Insecure creator has spent years turning Hollywood success into ownership.

On September 25, Issa Rae stood inside the Intuit Dome in Inglewood, a few miles from the neighborhoods that raised her, as the Los Angeles Orbit revealed its name. She wasn’t there as a celebrity guest. She narrated the launch video, and she was there as an owner, alongside fellow investors Alexis Ohanian and Savannah James. Fifteen years earlier, she was posting episodes of a web series about being awkward to YouTube.

Most fans know the shows: The Mis-Adventures of Awkward Black Girl, Insecure, Rap Sh!t. Fewer know how much she owns. Over the past several years she has built a portfolio that runs through production, music, hair care, coffee, prosecco, fine jewelry and now professional sports.

It Started With the Company

Before the investments came the infrastructure. Issa Rae turned her early production work into a full media company, HOORAE, which she founded in September 2020. Under that banner she has produced series like Rap Sh!t and Sweet Life: Los Angeles.

In January 2026, Issa Rae signed a three-year first-look film and television deal with Paramount, which she develops through Hoorae Film & Television. That spring she went back to her internet roots with Screen Time, HOORAE’s first microdrama, created under a content deal with TikTok. In October the company followed with The Compatibility Experiment, a dating series on TikTok and PineDrama hosted by Love Island USA standout JaNa Craig.

Music has been part of the plan from early on. In 2019, Rae launched her record label Raedio in a joint venture with Atlantic Records. Rae has said the label was inspired by her history of centering female, independent and Los Angeles-based artists like SZA, Saweetie and Jazmine Sullivan on Insecure.

Coffee for the Culture

Issa Rae’s most personal investment may be the one closest to home. Hilltop Coffee + Kitchen was founded in 2018 by Yonnie Hagos and Ajay Relan, and Rae has been an equity partner since 2019. The brand has grown from its original View Park shop to locations in Inglewood, Eagle Rock and downtown Los Angeles, plus a shared spot in LAX Terminal 7 with Randy’s Donuts.

The partnership came from a simple wish. Rae, who grew up in View Park and Inglewood, wanted to open a coffee shop in her own neighborhood. It shows in the spaces, which are built as places where the community can gather and create, staffed mostly by locals.

Hair Care, Rooted in Real

On Insecure, Rae’s natural hair was its own storyline, so her move into hair care felt natural. In 2020 she joined Sienna Naturals, the clean, plant-based textured hair brand founded by her sister-in-law Hannah Diop, as co-owner and the face of the brand.

She stepped further into the spotlight in 2024 with the brand’s Rooted in Real campaign, her first video spot for Sienna Naturals. That July, the brand launched on Sephora, opening it up to a much bigger shopper base.

A Toast to Her Own Bottle

Any Insecure fan could have predicted this one. Prosecco was Issa Dee’s drink, and in October 2023 it became Issa Rae’s business. Viarae Prosecco launched as a partnership with E. & J. Gallo Winery. It’s crafted from 100% Glera grapes, grown and made by the La Marca cooperative in Treviso in Northern Italy.

Through Viarae, Rae set out to spotlight Black women in an industry where few have been visible. A year after launch, the line grew with Viarae Prosecco Rosé.

Jewelry She Bought for Herself

In 2024, Rae added jewelry designer to her résumé. She partnered with San Francisco fine jewelry brand Cast on the 22-piece Braeve Collection, sold through Cast and Nordstrom. Rae has said that jewelry marketing usually shows women waiting for a man to gift it, while Cast’s ethos is about women gifting themselves.

Her Seat in Sports

Issa Rae’s newest chapter is sports, and she’s moving fast. In February 2025, she joined San Diego FC‘s ownership group as a Club Partner ahead of the MLS club’s first season, investing through the African private investment firm Pave Investments.

This fall she turned to women’s sports. In September she helped launch the Los Angeles Orbit, the new League One Volleyball team that will play at the Intuit Dome. Weeks later, she joined Unrivaled, the 3-on-3 women’s basketball league founded by Breanna Stewart and Napheesa Collier. It was her first league-wide investment, made through Unrivaled’s oversubscribed Series C, which reportedly valued the league at $650 million. “After experiencing Unrivaled firsthand last season, it was clear that they’re building something special,” Rae said.

What’s Next for Issa Rae

Issa Rae is returning to HBO five years after Insecure ended, this time with her own production company, a studio deal, a TikTok slate and stakes in three professional teams and leagues behind her. The girl from View Park who got her start posting episodes to YouTube now owns part of a team that plays a few miles from home.