How Keeping It Real Made Issa Rae A Girl Boss In Hollywood

In a world where Hollywood loves to box people in, Issa Rae built her empire by doing the exact opposite—staying 100% true to herself. From a scrappy YouTube series to becoming one of the biggest names in entertainment, she’s proof that keeping it real pays off.

Before the fame, Issa Rae was just another creative trying to tell her story. In 2011, she dropped The Misadventures of Awkward Black Girl on YouTube, a hilarious and super-relatable web series about a quirky Black woman navigating life’s awkward moments. At the time, Hollywood wasn’t really checking for Black women like her who were awkward, introverted, and not fitting into the usual “strong Black woman” or “sassy best friend” stereotypes.

But Issa didn’t water herself down to fit in. Instead of waiting for Hollywood’s approval, she took matters into her own hands. When funding got tight, she launched a Kickstarter campaign—and the people showed up, donating over $50,000 to keep the show going. That’s when it became clear: people wanted to see real, authentic Black stories, and Issa was about to give them exactly that.

After Awkward Black Girl blew up, Issa Rae caught the attention of HBO, leading to her hit show Insecure, which premiered in 2016. From day one, Insecure was unapologetically Black. It wasn’t made to explain our culture to outsiders, it was made for us, by us. From the music to the jokes to the fashion, every detail felt authentic.

Hollywood has a habit of making Black creators change things up to be more “marketable,” but Issa wasn’t having it. She stayed in control of her vision, making sure Insecure reflected the real Black experience: messy, funny, beautiful, and complex.
A lot of people get famous and forget where they came from, but not Issa. Instead of just focusing on her own success, she made sure to uplift others. Behind the scenes of Insecure, she hired Black writers, directors, and crew members, giving people opportunities in an industry that often shuts them out.

And she didn’t stop there. She launched Hoorae, her own media company, to create even more space for Black creatives. Then she started Raedio, a music label that helps unsigned artists get their music in TV and film. She even invested in Black-owned businesses in South L.A. It’s one thing to make it—but Issa is making sure everybody eats.

Issa Rae didn’t have to fake it to make it. She showed up as her full, awkward, hilarious, and brilliant self and Hollywood had no choice but to take notice. By staying true to her vision, she didn’t just build a career; she changed the game for Black creatives everywhere.