Sep 26, 2022 · 1h 20m · how-i-built-this
HOORAE: Issa Rae
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, host Guy Raz interviews creator and entrepreneur Issa Rae, tracing her journey from producing low-budget college web series to creating HBO's acclaimed hit Insecure and building the HOORAE Media empire.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 35.9% of the talking time here. How this is scored →
Guy as informed peer 4.2 Guest teaching 1.9 Guest disagreement 1.1 Guy pushing back 0.9
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:17:00 Pushing Back on Career Timeline Optimism
When Raz points out Rae is only in her thirties with a long career ahead, Rae immediately counters that Hollywood enforces much harsher, compressed timelines and standards for women.
Hardest push from Guy ▶ 17:19 Probing Stanford IsolationRaz directly challenges Rae's university experience by citing quotes about the campus's lack of diversity and asking if she felt isolated in that environment.
Biggest teaching moment ▶ 47:00 Dismissing Algorithmic SEO TacticsWhen Raz asks whether search engine optimization and targeted YouTube descriptions drove her initial surge, Rae explains that true engagement came strictly from high-quality creative work and genuine word-of-mouth.
Guy holds their own ▶ 14:05 Citing Specific Spec Script DetailsRaz demonstrates deep research into Rae's early unpublished writing, recalling the exact title and plot of her teenage CBS spec script submission for Cosby.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Guy Raz Announces The Great Creators Podcast | 0 | 0 | 0 | 0 | Guy Raz delivers podcast announcements and an introductory monologue framing Issa Rae's career and early experimental projects. | |
| Senegalese Roots, Family Background, and Childhood in Los Angeles | 4 | 2 | 1 | 1 | Raz asks well-researched questions about Rae's family background, her father's medical practice in Inglewood, and Senegalese cultural expectations. | |
| Early Acting Passion and Discovering the Sitcom Blueprint | 5 | 2 | 1 | 1 | Raz demonstrates knowledge of 90s TV programming history as Rae recounts winning a physical Moesha teleplay script that served as her writing template. | |
| First Spec Scripts, Poor Man's Copyrights, and Creative Vulnerability | 5 | 2 | 2 | 1 | Raz brings up specific early spec scripts like Tongue Ring, while Rae describes using a poor man's copyright and dealing with early creative insecurity. | |
| Stanford Years, Hip-Opera, and Independent Stage Productions | 5 | 3 | 2 | 1 | Raz suggests Rae felt isolated at Stanford, but Rae clarifies she insulated herself within a supportive Black community and took creative risks putting on plays. | |
| Creating Dorm Diaries and Discovering Digital Distribution | 4 | 2 | 1 | 1 | Raz details his viewing of Rae's college footage while Rae explains the epiphany of Dorm Diaries bypassing industry gatekeepers directly to online viewers. | |
| New York Struggles, Apartment Burglary, and Defining Identity | 4 | 2 | 1 | 1 | Raz probes Rae's post-grad financial anxiety and introvert personality, while Rae shares the emotional impact of having her apartment burgled. | |
| Embracing the Awkward Persona and Returning to Los Angeles | 4 | 2 | 1 | 1 | Raz and Rae explore turning awkwardness into an identity marker, and Rae explains the peer intervention that convinced her to return to Los Angeles. | |
| Moving Home, The F Word, and Developing Production Discipline | 4 | 2 | 1 | 1 | Raz connects Rae's self-directed web series grind on The F Word to standard creative apprenticeship, while Rae emphasizes the discipline gained from weekly deadlines. | |
| Conceiving and Self-Starring in Awkward Black Girl | 5 | 2 | 1 | 1 | Raz describes specific comedic scenes from Awkward Black Girl, while Rae recounts rushing the project to production after seeing a call for a Black Liz Lemon. | |
| Kickstarter Crowdfunding and Scaling with Pharrell Williams | 5 | 2 | 1 | 1 | Raz asks about SEO and marketing tactics, but Rae clarifies success was purely organic word-of-mouth before detailing Pharrell Williams funding season two. | |
| The Shondaland Partnership and the Failure of I Hate LA Dudes | 5 | 2 | 1 | 1 | Raz and Rae review the development collapse of I Hate LA Dudes with Shonda Rhimes, with Rae explaining how conflicting network notes diluted her artistic voice. | |
| Developing Insecure at HBO and Launching ColorCreative | 5 | 2 | 1 | 1 | Raz maps out the timeline of Insecure's development with Larry Wilmore, and Rae recounts draining her savings to fund ColorCreative pilots while awaiting HBO's greenlight. | |
| Managing Insecure and Transitioning to Creative Entrepreneurship | 4 | 2 | 1 | 1 | Raz prompts Rae on shifting from artist to business owner, prompting Rae to explain how digital creators are inherently entrepreneurs managing product and pipelines. | |
| The HOORAE Media Empire, Rap Sh!t, and Reflections on Success | 4 | 2 | 2 | 1 | Raz notes Rae's youth in her 30s, but Rae points out the distinct compressed career pressures and biological clock expectations for women in Hollywood. |
Statements from this episode (13)
Rae avoids sharing finished scripts immediately to protect her initial confidence
“It is, and you don't want, and even now I feel that way. Like, I don't want it, I don't want any negative energy. I don't want anybody to tell me it's not good, or that it doesn't resonate with them. It's always better when you feel good about it. Like, that m…”
Rae: Stanford gave me room to fail creatively that NYU wouldn't have
“I really wanted to go to NYU, and there's no way in my mind that I would have been able to, like, fail, or suck, I'd say, as hard.”
Issa Rae: Self-producing and publishing online is viable path to bypass gatekeepers
“Because I had spent all this time trying to write and send my work to either producers, executives, contests, whatever, in an attempt to get it made, to get it seen. And I was either told why there wouldn't be an audience for this particular work, or that, you…”
Rae: Claiming your own awkwardness is a preemptive defense mechanism
“So in a way, it's a defense mechanism to outwardly claim it before someone else claims it about you. And also just be like, look, I know what it is, guys, ok? Just bear with me. I've already said what it is. Like, we've gotten that out the way.”
Rae: LA's entertainment scene is significantly slower and flakier than New York's
“I left New York and came to LA, and LA felt so slow to me. Like, LA people will be like, I'm working on a script, and you'll be like, where's the script? And they'll be like, oh, it's coming, I got you. New York, I'm working on the script. Where is it at? It's…”
Rae raised $60,000 on Kickstarter for 'Awkward Black Girl' in 30 days
“And we asked for 30,000 dollars, and then over 30 days, you know, people almost helped us to raise almost 60.”
Rae: Genuine word-of-mouth drives viewership much more than marketing optimization
“You can do things to amplify that, but if something is good to people, they're gonna talk about it, and that's gonna be the main source of your eyeballs, your support.”
Pharrell Williams funded Awkward Black Girl's second season through I Am Other
“He had one of those channels and was able to fund our second season via his I Am Other company.”
Rae: Prioritizing big names over a clear creative vision ruins TV shows
“I was just like, I just want to make a show. I just want to work with these people. And I don't really care about what I'm making. I just want to make with them. That is not, that's not, those aren't the right ingredients to make a good show.”
Rae: A TV pilot must fundamentally answer 'why today' for its characters
“One of the most common questions you get that I'll, that'll never leave my mind, but in, in pilots, there's always that question of why today? Why are we coming into this show today? And why are we following these characters on this specific day? What is our w…”
Rae self-funded three $50,000 ColorCreative pilots with her entire life savings
“So what if I do this with other writers and produce three pilots for 50,000 dollars each, and I thought I was gonna have money coming in. I was supposed to have money coming in, but it fell through, and I ended up funding it
With everything that I had made at …”
Rae: Every original ColorCreative pipeline writer eventually landed television industry work
“All of the writers that came out of that have ended up in television in some way”
Rae is working to build a major production studio in South LA
“Down the line, I want to have a studio in South LA. I want to have sound stages, and I'm working towards that, but the idea is to be one of the biggest entertainment media companies, and expand to global properties, and continue to create content in all forms.”