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For Issa Rae, an “Insecure” Ending Signals New Beginnings

The final season of Insecure is underway on HBO, and Issa Rae is already focused on what’s next, which she discussed on the season premiere of Boardroom’s “The ETCs” podcast.

Listen to the full episode by clicking here.

In Issa Rae’s mind, there was always an endpoint to her YouTube-series-turned-HBO-sensation, Insecure.

She just had to get there. 

“I like to know the writers had an ending in sight, and you’re building towards something,” she said on the Season 2 premiere of Boardroom’s “The ETCs” podcast this week. “Five seasons felt like a good capping point.” 

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So ends one of the most impressive journeys in the internet era of television. The legendary tale is well-known by now: Rae created a YouTube series, The Mis-Adventures of Awkward Black Girl, which relied on crowdfunding to finish its first season. It caught the eye of Pharrell for its second season.

From there, the concept gradually developed into an HBO pilot.

In making her way from YouTube obscurity to a premium television network, Rae blazed a new trail, establishing a template for ambitious creatives who dare to dream big. 

But now, with her flagship series wrapping up the way she always envisioned, she’s on to the next phase of her career. And at the moment, most of it appears to be behind the camera.

For now, she’s running her production company, Hooray Media, into its post-Insecure life. The 36-year-old will steer the ship through a lucrative five-year film and TV deal with WarnerMedia, which gives the likes of HBO, HBO Max, and Warner Bros. television exclusive rights to Rae’s TV work. On the film side, the deal spans WarnerMedia brands, including Warner Bros. Pictures Group, New Line, and, HBO Max.

She already has two new shows up and running with HBO, and she’s knee-deep in production of her next series, Rap Sh*t, a Miami-based series following two friends who kickstart hip-hop careers together. 

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The transition isn’t complete yet, as Insecure kicked off its 10-episode final season over the weekend. The adventures of Issa (the fictional version), Molly (Yvonne Orji), Lawrence (Jay Ellis), and the rest of the gang have to conclude. Rae admits she’s wary about sticking the landing, hoping to give fans a more Breaking Bad-level conclusion rather than a Game of Thrones-type whimper to the finish line.

“There were multiple finales written,” she told The ETCs. “Finally, I had a revelation, and was like, ‘This is the ending that I want.’”

Now, we just have to wait to see what Rae has in store — not only regarding the ending to her proper introduction to the world, but the beginning of her next phase to come.

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