When the pilot that later became Insecure was still in development at HBO, Rae founded a production company, ColorCreative TV, as an initiative to support minority screenwriters by showcasing and selling their work. In 2014, Issa told Ebony , “We’re providing a unique opportunity to get your pilot made,” she said. “Instead of going through the development process that can take a year, we’re getting content made within a month and exposing it to an audience to get support behind it.” ColorCreative has since grown into a management company. In 2020, Rae and her producing partner Deniese Davis brought on former CAA agent Talitha Watkins to run their management division.

After the success of her web series, Rae borrowed its title for her book of nonfiction essays, The Misadventures of an Awkward Black Girl. In the book, Rae talked about growing up as the daughter of Senegalese immigrant parents, and the struggle she had with not feeling “Black enough” as a kid. After its release the book became a New York Times bestseller.

After filming three seasons of Insecure throughout South LA, Rae made her own permanent stamp on the region. She partnered with Ajay Relan and Yonnie Hagos to open a second location of their coffee shop, Hilltop Coffee & Kitchen, in Inglewood, CA. Rae told Eater Los Angeles that she envisioned the cafe as a community hub and center for creativity. “I just feel like it’s so important to have these spaces where you feel safe, where you can be creative, and have a sense of comfort. To know that it’s your space,” she said. Rae also invested in Hilltop’s third location in Eagle Rock, which opened in November 2020, according to LA Magazine.

Music has been a huge part of Rae’s shows, from their hit soundtracks to Rae’s mirror raps. In 2019, Rae made her own entry into the music industry, co-founding a music label called Raedio with Atlantic Records. She told Pitchfork,  “Music has always been an essential part of every project I do and working with emerging talent is a personal passion.” Rae also had a cameo in the music video for Raedio’s first artist, Teamarrr.

After years on her own HBO show, Rae took her executive-producing skills over to Netflix. She EP’ed and starred in the rom-com The Lovebirds, co-starring Kumail Nanjiani. Since that gig, Issa has landed numerous other EP projects, including A Black Lady Sketch Show for HBO, the romance film The Photograph, the upcoming docuseries Seen & Heard and comedy series Rap Shit for HBO.

In 2020 Issa became the co-owner and face of Sienna Naturals, which was founded in 2011 by her longtime friend Hannah Diop. Rae told Elle, "I've known Hannah for a long time, and I got to see the brand evolve from her home. It’s expanded so much beyond that. The care and the research that has gone into this natural, safe, healthy brand, I knew that I wanted to be involved." The eco-conscious line became available at Target earlier this year.

Issa’s known for her fashion-forward looks on and off-screen. Earlier this year she partnered with the clothing brand Madewell on the fashion brand’s spring campaign. Over the campaign’s six-week run, she referenced other young Black creatives, including author Yaa Gyasi, art curator Autumn Breon, and poet Tonya Ingram, according to Fast Company.

In January, Rae followed in the footsteps of Shonda Rhimes and Alicia Keys by creating her own Masterclass. Rae’s class for the subscription service, subtitled "Creating Outside the Lines," includes lessons detailing her journey through Hollywood, and analyzing scenes from both The Misadventures of Awkward Black Girl and Insecure for writing tips. “In my MasterClass, I want to tell you everything that I’ve gone through, every mistake that I’ve made and everything that I’ve learned so far, so that you can do better than I did. If you have a desire to create, this class is for you,” she told Variety.

Rae shook Hollywood last March when she announced her overall deal with WarnerMedia. The deal, valued at $40 million over five years, gives HBO, HBO Max, and Warner Bros. Television exclusive rights to her television work, as well as first-look rights for her films at WarnerMedia film brands. “They wifed me up,” Rae told Variety. In addition to the deal on future projects, she also has projects in development at Netflix, Lionsgate, Sony and Universal.

Just this week, Issa announced her partnership with Converse on a new sneaker line called, "Issa Rae By You!" A remix of the brand's popular Chuck 70 shoe, Issa's limited edition line is centered around her "daily affirmations and manifestations," as per an Instagram post. The sneakers, co-created with graphic designer NickyChulo, can be customized with the words and phrases that inspire the multi-talented star, including "Run With It" and "Walking In Your Purpose." 

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