Eight years after first conceiving the idea for Insecure, Issa Rae’s hit HBO show airs its series finale on Sunday, December 26. Since creating the show, Issa Rae has become one of the fastest-growing media moguls in all of Hollywood. Period. What does Issa’s post-Insecure life look like? In this special episode of the Trapital hip hop business podcast, she gives us a hint at what her future holds.

I’ve written at length in the past about Issa Rae’s growing media empire. On top of hit TV shows, it includes feature films, a brand-new record label Raedio, hair care brand Sienna Naturals, a coffee shop in Inglewood, and too many more “synergies” to name. The media empire has shades of Disney and her personal role model, Oprah Winfrey.

You can ready my full analysis of how Issa built this modern-day media empire here: https://trapital.co/2020/04/23/how-issa-rae-became-the-modern-mogul/

Issa told me she’s taking January 2022 off once Insecure wraps up but that’s a small re-charge for a big year ahead for her Hoorae production company. She’s already announced new shows like Rap Sh*t and the revival of the Project Greenlight series. At this point, one has to wonder, “what is she not working on?”

In my Issa Rae interview, she explains what it takes to balance all these creative and business interests, plus a whole lot more. Here are the video chapters:

0:00 Introduction To Issa Rae Interview
3:00 On The Cusp Of Insecure’s Series Finale, How Does Issa Feel?
4:23 The Never-Ending Balancing Act Of Insecure’s Story
6:41 Issa’s Reaction To The AKA Sorority Controversy On The Show
7:20 How Will Ownership Play A Factor In Issa Rae’s Next Moves?
9:28 Tradeoffs Between Having A Distributor Vs. Direct Ownership
10:52 What Other Considerations Were There Before The WarnerMedia Deal?
11:59 Issa’s Relationship With WarnerMedia & HBO
13:29 The Synergies Across Issa Rae’s Businesses (Media, Coffee, Skincare, Etc.)
17:36 Would Issa Work With A Rising, Independent Streaming Service?
18:33 Issa’s Take On What Went Wrong With Quibi Streaming Service
21:21 Will Issa Rae “Double Down” On One Creative Outlet Or Continue Balancing Them All?
23:13 Taking Lead On The Creative Vs. Taking Lead On Business Endeavors
25:18 How Issa Rae Decides What Projects & Businesses To Take On
27:22 Issa Rae’s Upcoming 2022 Projects

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