§ ENTERTAINMENT · 2 MIN READ

Issa Rae Bought Back the Block

She turned a YouTube series about being awkward into an HBO empire. Then she did the rarest thing in Hollywood and brought the money home to South LA.

By Culture

August 22, 2026

Issa Rae Bought Back the Block

THE SHORT VERSION

Issa Rae launched The Misadventures of Awkward Black Girl on YouTube in 2011 after no network would cast the character she knew was real, and it became the HBO series Insecure, which ran five seasons. She kept the investment in South Los Angeles, where her production company Hoorae is based and where she co-owns Hilltop Coffee in Inglewood.

Issa Rae grew up in South Los Angeles and built her start on YouTube with The Misadventures of Awkward Black Girl.
Her HBO series Insecure was filmed across real South LA neighborhoods on purpose.
She reinvests where she is from, including co owning Hilltop Coffee in Inglewood and building her Hoorae media company in South LA.
Nobody greenlit her. She greenlit herself, then treated the neighborhood as an investment instead of a backdrop.

There is a version of the Hollywood story we all know by heart. Talented kid makes it, moves to the hills, and the old neighborhood becomes a line in interviews. Issa Rae looked at that script and rewrote it, which is fitting, because rewriting scripts is literally her job.

Issa Rae. Photo: wblsfm1075, CC BY 3.0, via Wikimedia Commons. Edited by Culture.
Issa Rae. Photo: wblsfm1075, CC BY 3.0, via Wikimedia Commons. Edited by Culture.

Awkward, On Purpose

She grew up in South LA, in View Park, and her origin story should be taught in every media class. No network would cast the character she knew was real: a regular, brilliant, awkward Black girl. So in 2011 she cast herself. The Misadventures of Awkward Black Girl went up on YouTube with no gatekeeper's permission, found its audience directly, and proved the demand that executives swore did not exist.

HBO eventually agreed, and Insecure ran for five seasons as one of the defining shows of the decade. Emmy nominations, a Peabody Award for her work, and a generation of Black women who finally saw their actual interior lives on premium cable.

The Camera Stayed Home

Watch Insecure with a map open sometime. That is not a backlot. She shot across real South LA, Inglewood, Leimert Park, Baldwin Hills, and she framed those neighborhoods the way they deserve: in golden light, full of life, worth looking at. For people who only knew South LA from the evening news, that was a re-education, delivered weekly.

“First she put the neighborhood on screen. Then she put her money in it.”

Owner Moves

This is the part I respect most. The production company, Hoorae, is hers and is planted in South LA. She co-owns Hilltop Coffee in Inglewood, so the corner shop where people write their screenplays is one she has a stake in. Ownership, location, payroll: all pointed home.

The Playbook, and How to Run It

Nobody was going to greenlight her, so she greenlit herself. And when the money came, she treated the neighborhood as an investment, not a background. Four moves, in order:

1Cast yourself. The role you cannot get is usually the one only you can play, and proof of demand beats a pitch about it.
2Publish where the audience already is, without asking. Start the channel and put the first episode up this month.
3Shoot where you are from and name it on screen. Specificity is what made Insecure feel like a place instead of a set.
4When it pays, buy something on the block. A stake in a real storefront is what turns a career into an economy.

The last step is the one most people skip, and it is the one you can start smallest. Spending at the shops around you is the entry-level version of what she did with Hilltop.

Tyler ran the same play from Hawthorne, and Kendrick ran it from Rosecrans. Build your thing, then bring it home. That is the whole playbook, and she ran it in public.

§ QUESTIONS PEOPLE ASK
How did Issa Rae get started?
Issa Rae created and starred in The Misadventures of Awkward Black Girl on YouTube in 2011, after networks would not cast the character she knew was real. The web series found its audience directly and proved a demand executives said did not exist, which led to Insecure at HBO.
Where did Issa Rae grow up?
Issa Rae grew up in View Park, in South Los Angeles.
What does Issa Rae own in South LA?
Issa Rae's media company Hoorae is based in South Los Angeles, and she is a co-owner of Hilltop Coffee in Inglewood. Insecure was also filmed across real South LA neighborhoods rather than on a backlot.
What is Hoorae?
Hoorae is Issa Rae's production company, and it is planted in South Los Angeles.
Where was Insecure filmed?
Insecure was filmed across real South Los Angeles neighborhoods, including Inglewood, Leimert Park and Baldwin Hills. Shooting on location was a deliberate choice, and the show showed those places in a light most national television never gave them.
How many seasons did Insecure run?
Insecure ran for five seasons on HBO and became one of the defining shows of the decade, earning Emmy nominations and a Peabody Award for Issa Rae's work.
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