This story is part five of Boardroom’s Black History Month “Playmakers” series highlighting figures across sports, business, culture, and entertainment who are working to effect socially conscious change.
Part I: Patrick Mahomes | Part II: Karl Fowlkes | Part III: Nicole Lynn
Part IV: Chris Paul | Part VI: Quinta Brunson | Part VII: Broccoli City
Throughout her prolific rise, Issa Rae has made it her mission to elevate people of color from all walks of life.
It pays to be awkward. Or at least it worked for Issa Rae. For the last decade, fans have watched the actress, writer, and producer catapult from YouTube star to an empire builder, elevating Black voices in television, film, philanthropy, and more along the way. At 38, Rae toes the line between an executive who has accomplished everything and someone just getting started. She has an incomparable knack for grasping the audience’s attention in 30 minutes, squeezing the most out of every second while still leaving viewers hungry for more.
“Media mogul” doesn’t do Issa Rae justice because she is more than someone influencing how we consume content. She is unapologetically Black, roots for everyone Black, and is the epitome of a Boardroom Playmaker.
Insecure is the new Awkward
Rae relates to many within the Black community because her material specifically caters to people of color. The Los Angeles native’s breakout series, The Mis-Adventures of Awkward Black Girl, premiered on YouTube in 2011. The series showed interactions between J (Rae) and her colleagues from a first-person perspective, and they really were not that different from experiences most Black people face on a daily basis. It was an early test of whether Rae could make long-lasting content relevant past the early 2010s. She passed with flying colors, and Insecure was born.
In 2013, Rae and Larry Wilmore began work on the comedy show with her as the star. Much like the aforementioned project, Insecure chronicles the life-changing moments of a twenty-something Black woman in southern California. HBO picked up the pilot in early 2015 and the show ran for five seasons before ending in 2021. The series picked up multiple Emmy, Golden Globe, NAACP Image Award nominations among a host of other honors over the course of its storied run, solidifying a permanent impact in television and Black culture.
“I always knew I was going to do these five seasons,” Rae said to Variety. “Now that it’s coming to an end, and we’re shooting, I have no regrets. But there’s an element of knowing I’m going to miss this, and I don’t want to take this for granted. There’s no feeling like doing your first TV show and doing it with people who are also fresh with you, and growing and building with them.”
The hit show may have come to an end too early or at exactly the right time, depending on who you talk to, but it paved the way for ex-staffers to pivot to other transformative opportunities. According to Time, co-executive producer Regina Hicks went on to co-create Netflix comedy series The Upshaws. Former production assistant Kindsey Young now writes for Grand Crew, an NBC program led by fellow Insecure alum Phil Augusta Jackson. Amy Aniobi created her own mentorship and networking program Tribe, which caters mostly to writers of color.
Issa Rae is More Than an Entertainer
Sure, millions take notice when Rae premieres a new on-screen project, but her impact reaches far beyond Hollywood. In 2017, the Stanford grad went viral for a candid red carpet moment at the 2017 Emmys. When asked who she was rooting for, Rae told Variety, “I’m rooting for everybody Black.”
Her remarks resonated with many, and to this day, memes, GIFs and merch forever connect her to that five-word response. Rae wasn’t speaking in jest. Since that moment, the Rap Sh!t creator has done her part in elevating Black voices. In 2019, minority-owned restaurant Hilltop Coffee + Kitchen opened a second location in downtown Inglewood. Its co-founders, Ajay Relan and Yonnie Hagos, partnered with Rae to bring the new restaurant next to Inglewood City Hall and Stevie Wonder’s radio station, KJLH. Rae herself still lives in the neighborhood and her media label, Hoorae, is headquartered there.
Rae also lends her support to initiatives like Destination Crenshaw, an infrastructure and economic development project celebrating Black art and culture on Crenshaw Boulevard. In September 2021, Rae teamed up with American Express to encourage all Black-owned businesses to officially certify their companies through a newly launched program in partnership with the U.S. Black Chambers, Inc.’s (USBC) ByBlack initiative. It was the launch of the “first national certification program exclusively for Black-ownership designation.” Rae is also the co-owner of Sienna Naturals, a Black-owned hair care brand for natural coils.
Building an empire comes with its challenges, but Rae has learned to evade the stereotype of being labeled difficult while remaining authentic to her craft.
“Don’t be afraid to be a bitch,” she said on an October 2022 episode of Meghan Markle’s podcast, “Archetypes.” She also revealed more wisdom she absorbed from equally successful Black women in show business like Shonda Rhimes, Ava DuVernay, Debbie Allen and Mara Brock Akil.
“They really stressed to me that I could never have this opportunity again,” Rae continued. “They were like, ‘You have this show with HBO, you’ve been wanting this the entire time, and you’re scared to say no or be a b-word? What if you never get this chance again?'”
The takeaway? No matter the accolades and opportunities that continue to roll in, never feel too comfortable and always remain ambitious.
“I don’t care how settled I may feel in my career, I don’t care how much praise I get, I approach every project thinking, ‘What if I never get to do this again?’ I’ve never been stagnant, I’ve never been satisfied … that hunger just remains in me.”
More hit shows and Black icons will come along, but one constant remains: Issa Rae is the blueprint.
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