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Boardroom is a sports, media and entertainment brand co-founded by Kevin Durant and Rich Kleiman and focused on the intersection of sports and entertainment. Boardroom’s flagship media arm features premium video/audio, editorial, daily and weekly newsletters, showcasing how athletes, executives, musicians and creators are moving the business world forward. Boardroom’s ecosystem encompasses B2B events and experiences (such as its renowned NBA and WNBA All-Star events) as well as ticketed conferences such as Game Plan in partnership with CNBC. Our advisory arm serves to consult and connect athletes, brands and executives with our broader network and initiatives.

Recent film and TV projects also under the Boardroom umbrella include the Academy Award-winning Two Distant Strangers (Netflix), the critically acclaimed scripted series SWAGGER (Apple TV+) and Emmy-nominated documentary NYC Point Gods (Showtime).

Boardroom’s sister company, Boardroom Sports Holdings, features investments in emerging sports teams and leagues, including the Major League Pickleball team, the Brooklyn Aces, NWSL champions Gotham FC, and MLS’ Philadelphia Union.

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

Last Updated: September 29, 2022
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. 

https://www.youtube.com/watch?v=kBb2Pbh20m4
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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.


Never miss an episode of “The ETCs.” Subscribe to the show on Apple PodcastsSpotify, and Stitcher.

Sam Dunn

Sam Dunn is the Managing Editor of Boardroom. Before joining the team, he was an editor and multimedia talent for several sports and culture verticals at Minute Media and an editor, reporter, and site manager at SB Nation. A specialist in content strategy, copywriting, and SEO, he has additionally worked as a digital consultant in the corporate services, retail, and tech industries. He cannot be expected to be impartial on any matter regarding the Florida Gators or Atlanta Braves. Follow him on Twitter @RealFakeSamDunn.

About The Author
Sam Dunn
Sam Dunn
Sam Dunn is the Managing Editor of Boardroom. Before joining the team, he was an editor and multimedia talent for several sports and culture verticals at Minute Media and an editor, reporter, and site manager at SB Nation. A specialist in content strategy, copywriting, and SEO, he has additionally worked as a digital consultant in the corporate services, retail, and tech industries. He cannot be expected to be impartial on any matter regarding the Florida Gators or Atlanta Braves. Follow him on Twitter @RealFakeSamDunn.