Issa Rae Shares Her No-Nonsense Playbook for Winning — ‘Don’t Be Afraid To Be A B—ch’

Issa Rae has achieved the unthinkable. She began by creating her own YouTube series, The Misadventures of Awkward Black Girl, and transformed the success of that quirky, relatable show into Insecure—the HBO hit that ran for five acclaimed seasons from 2016 to 2021. Through grit, creativity, and unwavering consistency, Rae turned her vision into reality, proving that with determination and hardwork, dreams really can come true.

In celebration of Black Women’s History Month, Black America Web is diving into Issa Rae’s inspiring “Hustle Playbook,” examining the bold moves and smart decisions that helped her build a powerful legacy in film and television.

Here’s a look at her extraordinary roadmap to success.

Start small, but think big! Don’t wait for the perfect time.

Issa Rae’s career blossomed from humble beginnings. In 2011, she launched and starred in her breakout YouTube series, The Misadventures of Awkward Black Girl. The hilarious show followed her fictional alter ego “J” as she navigated painfully awkward moments with co-workers and love interests, often finding herself in hilariously uncomfortable situations. The series quickly gained a loyal following, racking up over 1.9 million views.

When it came time to produce Season 2, Rae didn’t wait for Hollywood’s green light—she took matters into her own hands. According to Black America Web, the California native crowdfunded over $50,000 to bring the next season of The Misadventures of Awkward Black Girl to life.

Her hustle proved that she didn’t need big studio backing to bet on herself. She believed in her vision, started small, and thought big. And most importantly, she didn’t wait for the perfect moment—she created her own lane, pushing forward through every hurdle and setback.

Play the long game. Consistency builds longevity.

HBO's 'Insecure' Series Finale Premiere Party — Source: Variety

With a growing fanbase and undeniable buzz around her name, Rae eventually caught the attention of Hollywood heavyweights. In 2012, after her viral success on YouTube, Rae met with Casey Bloys, Chief Content Officer for HBO and HBO Max. According to CNN, that meeting marked a turning point. HBO saw her potential and offered her the opportunity to bring her creative vision to the network.

Teaming up with executive producer Prentice Penny, Rae went on to co-create Insecure, the critically acclaimed series that debuted in October 2016 and ran for five powerful seasons until 2021. The show followed best friends Issa and Molly as they navigated love, friendship, career challenges, and the sometimes messy, always relatable reality of adulting. What set Insecure apart was its authenticity. It wasn’t just entertaining; it was honest, vulnerable, and deeply reflective of the Black millennial experience.

Each season raised the bar. Rae and Penny never let up, consistently evolving the storyline and deepening the complexities of the show’s characters. Issa and Molly’s relationship—full of loyalty, tension, growth, and love—resonated with audiences in a way that felt personal. The show also stood out for its cinematic visuals, curated soundtracks, and cultural nuance—and its impact was undeniable.

Insecure earned four Emmy nominations and won a 2018 Peabody Award for excellence in entertainment.

Despite her growing influence, Rae has been candid about the challenges of breaking new ground in the industry. Per CNBC, speaking at the 2022 FutureWorks conference, she admitted that as Insecure gained momentum, she was initially “scared” of being seen as “difficult” when pushing for creative risks. That fear of rocking the boat is something many women—especially Black women—face in professional spaces. But Rae turned to a powerful circle of mentors, including Shonda Rhimes, Ava DuVernay, Debbie Allen, and Mara Brock Akil. Their advice was clear: “Don’t be afraid to be a bitch.” In other words, speak up, take risks, and own your power.

Expand, expand, expand!

That guidance helped Rae not only steer Insecure to greatness but also build a lasting legacy. When the show wrapped its fifth and final season in 2021, Rae’s success was far from over. That same year, she signed a groundbreaking five-year overall deal with WarnerMedia—HBO’s parent company—to develop new television shows and films. Variety reported the deal was valued at around $40 million, a testament to Rae’s influence and potential as a media mogul.

Rae was already thinking bigger. In 2020, she launched her own production company, Hoorae Media, as a hub for her expanding creative empire. Her mission? To create more opportunities for underrepresented voices and tell stories that disrupt the norm. Under Hoorae, Rae has developed an impressive slate of projects across multiple platforms. According to Variety, these include: Tre Cnt, a coming-of-age wrestling drama for HBO, Seen & Heard, a docuseries exploring the Black TV writer experience, also for HBO, Rap Sh!t, a comedy series that followed two women navigating the music industry, and Perfect Strangers for Spyglass, among several other projects.

Outside of the film industry, Rae parlayed her success into other incredible ventures like her buzzing haircare brand Sienna Naturals and her new restaurant Somerville.

Rae has proven time and again that she’s not just a creator—she’s a visionary. From DIY YouTube beginnings to multimillion-dollar studio deals, she’s built her career with fearless authenticity, relentless ambition, and a deep commitment to uplifting others.

Happy Black Women’s History Month to Issa Rae!

Issa Rae: Celebrating Black Women's History Month