Meet The Tech Exec That Inspired Issa Rae To Launch ‘Misadventures of Awkward Black Girl’

Imagine checking your Twitter and seeing a tweet from Issa Rae crediting you as the inspiration for the start of her career in entertainment. 

That’s what happened to Leslie Pitterson, a communications executive who wrote an article Rae says changed her life. 

The year was 2010, and Pitterson was a Columbia University student at the time, working as a busy freelance writer. She penned an incredibly thoughtful article for Clutch Magazine that explored the oft-overlooked nerdy Black girl trope in TV and film, a representative that resonated with Pitterson and so many others. She beautifully illustrated that when Black women did come across our screens, they showed up strong, uber-confident and incredibly put-together which is flattering, but exclusionary and even intimidating to those that don’t see themselves that way. 

“I was seeing Black women onscreen at that time who were already kind of,  ‘made it,’ ” Pitterson explained. “ I just felt like so many of the portrayals with us were either incomplete or they were too glossy—they glossed over what our actual lives felt like and I wanted to put that observation I’d made out into the universe.”  

Fortunately, Pitterson’s April 2010 piece was in Rae’s orbit. 

About 10 months later, the first episode of Misadventures of Awkward of Black Girl (MABG) was posted on Youtube, effectively shifting the landscape of the TV industry for Black creatives from then on. 

A sign of her social media savvy even back then, Rae sent Pitterson a thank-you note in the form of a Tweet to acknowledge her influence. It simply read,  “@LesliePitterson, the character your article inspired,” followed by a link to the first MABG episode. 

“I was incredibly flattered, not because I could’ve predicted the massive success of the web series, or Insecure or Issa, but just because she’d read my work and was moved by it,” Pitterson shared with Essence. “As a Black woman in the media industry, you don’t always feel seen.” 

Much like Rae, Pitterson’s star has risen significantly since her freelance days of writing 7-8 pieces in her Harlem brownstone. The Columbia University grad has led communications teams for Morgan Stanley, Nielsen and most recently, head of comms (formerly) for Google. She said she can relate to Rae in that she had to break through to an industry that is traditionally white male dominated. 

“I try to be really honest with folks about the career climb,” she said. “One of the things I try to make sure I’m real with people about is they’re going to be moments where you feel alone. And so it’s really important to create a community. Although I’m no longer there, my experience at Google was incredible because I was able to create enough of a community to feel supported. Mentors like Vidhya Srinivasan and many others were able to help me navigate that fairly uncharted territory of being one of the only women on my leadership team. I was usually the “only” a few times over when I showed up to these meetings: the only woman, the only Black person. So it’s really important to be connected with people that understand that unique space you’re in. And this extends throughout my entire career. Mentors from my former workplaces like Bonita Stewart of Gradient Venture and Mandell Crawley from Morgan Stanley were integral in helping me make the climb. You can’t go It Alone. You just can’t.” 

With the recent culmination of Rae’s incredibly impactful series Insecure, Pittersen said she’s honored to have held a part in inspiring a different kind of Black Girl Magic representation. 

“The beautiful thing about seeing MABG and  Insecure is they’re so authentic,” she shared . “It’s really important we validate each other and that when we see stories, we do our part to maximize them. Our voice, every one of our voices, has power.

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