Issa Rae has built a multifaceted career as an actor, producer, director, and entrepreneur.

With a net worth that Celebrity Net Worth estimates to be around $20 million, Rae first gained a devoted following through her 2011 YouTube series “The Misadventures of an Awkward Black Girl,” and later cemented her cultural impact with the Emmy-award-winning HBO series “Insecure.”

Despite her achievements, Rae admits she doesn’t feel successful — at least not right now. Appearing on the first episode of KevOnStage’s “Not My Best Moment” podcast on Nov. 11, 2025, Rae shared that she currently feels stagnant in her career.

“I know that I appear successful to other people, but right now, no, I feel really stagnant… because I only feel successful when my sh-t is on the air. I don’t have sh-t on the air right now,” Rae said, acknowledging that creating shows is her first love.

“Like I can have the 18 businesses that you said, and those are like great passion projects, but like what I do and what I get excited about isn’t happening right now. So no, I don’t feel successful. Yeah, I’m optimistic, but I’m not successful right now,” she added.

Reflecting on her early days before “Insecure,” Rae recalled pouring every cent she had into an independent pilot. With directors and cast members in place and production underway, Rae couldn’t back out — much to her business manager’s distress.

“It was the stupidest thing I’ve ever done because it was literally all the money I’d ever made in my life until that point,” Rae told KevOnStage.

She also touched on “cancel culture” and how it is constantly resurfacing old tweets on the platform now known as X. Rae admits that early in her career she left no room for error. At the time, she used a program to scrub her online footprint, deleting thousands of tweets at once as her visibility began to rise.

“I say that I’m rich right now, and that is great, but that’s a very current thing. I think about that constantly. I know that I can save now, and that was my issue before; it was just really hard to save money,” Rae said.

“But yes, this can all go away immediately, and it could go away for some sh-t that we were just talking about because a clip surfaces, or people decide they don’t f–k with you anymore, and I pride myself on being able to create on a dime,” Rae added.

Beyond entertainment, Rae has made investments across the beauty, tech, and sports industries — all aimed at serving Black audiences.

How Issa Rae Built Her Empire

As AFROTECH™ previously reported, Rae released her memoir “The Misadventures of an Awkward Black Girl,” a New York Times bestseller, in 2015.

She later expanded her creative footprint with the launch of Hoorae — an incubator and management arm dedicated to nurturing Black talent. The company was initially founded in 2014 as ColorCreative TV.

In March 2021, Hoorae signed a five-year, eight-figure first-look deal with WarnerMedia to develop new television projects.

Rae’s first feature film released under Hoorae, “One of Them Days” — starring SZA and Keke Palmer — hit theaters on Jan. 17, 2025. The film earned $14 million in its first four days, Vulture reported.

Rae also ventured into music, launching her record label Raedio in 2019 in partnership with Atlantic Records, as AFROTECH™ previously shared.

The multi-hyphenate is the co-owner of natural haircare brand Sienna Naturals as well, which she launched in 2020 alongside Hannah Diop, per AFROTECH™. The company focuses on plant-based ingredients and sustainable practices.

An Inglewood, CA, native, Rae, additionally invests in real estate, specifically in Los Angeles — a move that was intentional as she expands her commitment to Black communities and local businesses.

“It was a big deal to purchase property in South L.A., and our ultimate goal is to have a studio, and that is in the works,” Rae told Marie Claire in 2022.

“I have such a love for where I come from and my city, and I also just approach my business ventures with my lifestyle in mind,” she continued.

In addition to TV show “Insecure,” Rae has appeared in films such as “The Photograph,” “Little,” “Barbie,” and “The Lovebirds,” as well as voiced Spider-Woman in the animated hit “Spider-Man: Across the Spider-Verse.”

Her production company also produced HBO’s comedy series “Rap Sh!t.” Rae created the series and co-wrote several episodes before its cancelation in 2024 after two seasons, per Deadline.

In 2023, Rae had expanded her entrepreneurial portfolio further by launching a prosecco line, Viarae, in partnership with E. & J. Gallo Winery. That same year, the media mogul joined the new ownership group that purchased the U.S. SailGP racing team — a move described as “the largest team acquisition in SailGP history,” AFROTECH™ previously reported.

As of February 2025, Rae also became a club partner in the San Diego Football Club (SDFC), joining its ownership group through a partnership with Pave Investments, per AFROTECH™.

“Joining San Diego FC’s ownership group is an incredible honor, and I am thrilled to be part of building something that represents and uplifts this vibrant community,” Rae said in a press release.

“Soccer is a universal language that has the power to bring people together, and I look forward to contributing to San Diego FC’s journey as we make history in MLS,” she continued.