HOORAE: Issa Rae

Obsessed with TV and passionate about writing, Issa Rae sent an unsolicited script to CBS’s Cosby when she was still in middle school. By her 20's, she realized there was a certain type of character that was absent from the media landscape—a character she would eventually inhabit in her breakout YouTube series, "Mis-Adventures of Awkward Black Girl." From there, Issa created the five-season HBO hit Insecure, but first went through a bruising gauntlet of rejections and reversals as she learned to navigate Hollywood. Today, Issa has built a company—HOORAE Media—which produces her new HBO show, Rap Sh!t, and multiple other TV and film projects. Listen to The Great Creators https://podcasts.apple.com/us/podcast/the-great-creators-with-guy-raz/id1640546593 launching September 20th See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

  Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2 a.m. kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan,

• 0:46Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt. We get support from U.S. Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't.

• 1:32Guy Raz?

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• 2:14Guy Raz?

  Now you're earning 3% cash back on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association pursuant to a license from Visa USA Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer.

• 2:58Guy Raz?

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• 3:40Guy Raz?

  Value estimate based on $50 per visit rate to purchase additional visits or bring a guest to the Delta Sky Club. Make every trip feel more rewarding with the card that upgrades your travel. Apply today at delta.com/cardsocial. Offer ends November 4, 2026. Minimum spending requirements and terms apply. Flights are fulfilled as flight certificates valid for Delta Comfort or Delta Maine to select domestic destinations. Book 21-plus days in advance. Up to $80 per person and taxes and fees apply. Other restrictions apply. When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up, and getting on with my day.

• 4:23Guy Raz?

  And it reminds me a little bit of the founders I talked to on this show, because the best ones obsess over things their customers will never see. Tiny details, invisible improvements, relentless iteration. And not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage. It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular gas in port fuel-injected engines. Actual results may vary.

• 5:07Guy Raz?

  Visit mobili fuels.com for details. Hey, it's Guy here with a very exciting announcement. I have a brand new podcast. It's called The Great Creators and it launches on September 20. And each week, I'll be interviewing some of your favorite actors, comedians, and musicians about their lives, their work, and where they find creativity. So please check out The Great Creators. It's available wherever you find your podcasts. And please do subscribe so you won't miss any of the episodes. And our first episode is with Stephen Colbert. So check out The Great Creators wherever you get your podcasts. And we'll include a link in the show notes to this episode, too. Thanks. Now enjoy How I Built This.

• 5:55Speaker 01

  I think that's also the embarrassing part of working in Hollywood, is you get these announcements of things that are happening and the support. And then they just disappear. And while there's not an announcement that it's not going, you still get those questions.

• 6:10Guy Raz?

  How's it going?

• 6:11Speaker 01

  Yeah, how's it going? What? It must be great.

• 6:12Guy Raz?

  How's Shonda?

• 6:13Speaker 01

  Ah, Shonda's... And then it's just like, oh, yeah. Just different direction. You know, I was just working on a lot of things, so, you know. Maybe just don't ask me. Maybe just don't. Do I ask you about your work every day? No. Do I ask you how your project's going? But no, like, it was just, it was really devastating. And I thought it was over for me. I thought nobody's gonna want to work with the failure who couldn't make a show with Shonda Rhimes, who couldn't, like, make the layup.

• 6:48Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 7:00Guy Raz?

  I'm Guy Raz, and on the show today, how Issa Rae refused to wait for permission to make TV and made her own, and how she turned her YouTube content into a brand, two hit TV shows, and eventually, a Hollywood production company.

• 7:24Guy Raz?

  There's something to be said about thinking of a startup like a sandbox. Most of us learned our earliest skills in the sandbox. We learned how to use a shovel, we learned how to search for buried treasure, and in my case at least, I learned not to eat sand anymore. But the point is, it was a place to experiment, even as toddlers. The concept of the sandbox in business is important because it can be a place where you can try a bunch of stupid things out and sharpen them over time before anyone really notices. If you remember a recent episode about Dogfish Head Brewery, Sam Caligoni's sandbox was throwing any fruit he could find into his batch of homemade beer.

• 8:09Guy Raz?

  He'd invite friends over and let them try it. Sometimes it was great, but mostly it wasn't. And Sam was doing this long before he went on to build his craft beer business. For Issa Rae, her sandbox was making videos and throwing them up on the internet. Sure, it would have been great to make something with the backing of a major Hollywood studio, but when you're young, inexperienced, and unknown, very few studios are interested. From a very early age, like age 13, Issa Rae was writing scripts. She even submitted some unsolicited scripts to sitcom producers in LA in the 1990s.

• 8:50Guy Raz?

  In college, she'd recruit friends to act out her ideas and video them with a camcorder she checked out from the library. And she started a web series that, if you look really hard, you can still find on the internet. Very few people saw those videos. And as you will hear, Issa cringes just a bit when she thinks about those videos today. But none of that matters because she was playing in a sandbox, building up skills and confidence and techniques that would serve her well 10 years later, when she finally did get a chance to do it on a Hollywood-level scale. At age 22, she wrote an entry in her diary, which would ultimately shape her entire career.

• 9:33Guy Raz?

  She wrote, "I am awkward and black." And over the next few years, Issa discovered there were a lot of women who felt the same way, and it would inspire her to make a web series based on this concept called, of course, "The Misadventures of Awkward Black Girl." Now, it didn't cost much to make, but Awkward Black Girl eventually got noticed by some influential artists, including Pharrell and Shonda Rhimes. That low-budget web series would lead to a deal with HBO and Issa's first major TV show, Insecure, which ran on HBO for five seasons. Today, Issa is one of the hottest young producers in Hollywood.

• 10:15Guy Raz?

  She's built a production company that has audio and video and film divisions and a talent management arm that works with rising artists. And she's just getting started. But the path to success, as you will hear, was filled with lots of rejection, lots of failure, and endless uncertainty. Issa Rae was born in LA and moved around a lot as a kid. Her dad was from Senegal, and the family relocated there for a few years when Issa was young. Then, the family moved back to the US, where Issa attended grade school in Maryland, before heading back once again to Los Angeles. Her dad was a doctor and opened up a family practice there.

• 10:56Speaker 01

  Yeah, I remember him, you know, he opened this practice in Inglewood. And I remember... Visiting it, he had maybe like a launch party. That's not what you call it, but it was something.

• 11:11Guy Raz?

  The medical practice launch party.

• 11:13Speaker 01

  Yeah, like a warming, an office warming party. And I just remember seeing it decorated to be catered to kids. And I thought that that was super beautiful. And, you know, I was in this neighborhood that was, he was servicing predominantly black and brown patients. And it was just like, oh, my dad built something.

• 11:33Guy Raz?

  Yeah.

• 11:33Speaker 01

  From the ground up. This is, that stood out to me as, you know, something that was distinctly his and special.

• 11:40Guy Raz?

  He's a pediatric specialist, right? Is that right?

• 11:43Speaker 01

  Yeah, he's like a family practitioner, but yes, he's a pediatrician.

• 11:47Guy Raz?

  Which is always really helpful to have in the family.

• 11:49Speaker 01

  Oh, 100%. But also, he's the most dismissive of any, any ailments we may have. Cause he's just like, he's seen it all, so.

• 11:59Guy Raz?

  He's seen it all.

• 12:00Speaker 01

  But it's, it is really helpful. Like even just the other day, I was like, ah, I have this thing, but if it doesn't go away in three days, I'll just, I'll ask my dad what's up. And he's, if you're worried, he will ease your worries. So that's the convenient part.

• 12:13Guy Raz?

  That's actually, when you say dismissive, actually, that's a probably surprisingly comforting.

• 12:17Speaker 01

  Yes.

• 12:18Guy Raz?

  Like, oh yeah, some big deal.

• 12:19Speaker 01

  100%.

• 12:19Guy Raz?

  Just go, go to work.

• 12:21Speaker 01

  Exactly that. If, if he's concerned, then I'm concerned.

• 12:25Guy Raz?

  All right. So the whole family moves out to LA and you start middle school there. A magnet school that was a sort of a science focus, magnet school. Were you a science focused kid?

• 12:37Speaker 01

  No, but my dad, again, you know, he was a doctor and so I, and he was very clear about how proud he would be if one of us became doctors. So for me, I was like, it's gonna be me then. Of course I'm gonna make him proud. I want to be a doctor too. Just like him. And of course, even seeing his practice, seeing his name.

• 12:56Guy Raz?

  Yeah.

• 12:57Speaker 01

  On the clinic was special. Going to school, going to middle school and being like, oh, your last name is mispronounced. Diop, joke.

• 13:05Guy Raz?

  Jope.

• 13:06Speaker 01

  But you're, is your dad, like, is your dad my doctor? And that was special to me. So for me, that was, the vanity of it might have kind of stoked my interest in science and medicine.

• 13:21Guy Raz?

  Yeah, and I guess I should mention Ray is your middle name, your last name.

• 13:23Speaker 01

  Ray is my middle name, yes.

• 13:26Guy Raz?

  Tell me about sort of home life, like, like cultural life. Was, was Senegalese culture a big part of? Of your upbringing, the food you ate, or celebrations, or even communities that you, your family spent time with?

• 13:40Speaker 01

  Yeah, definitely. It was, it was, I would say, perfectly balanced because my mom was, my mom was Christian, my dad's Muslim, and she's from Louisiana and he's from Senegal. And by way of living in LA, we had a lot of relatives come visit us. But Senegalese culture is such that if someone knocks on your door from Senegal and wants to stay with you, you have to let them.

• 14:07Guy Raz?

  They're in.

• 14:07Speaker 01

  Yeah, they're in. So a lot, we had a lot of Senegalese relatives staying with us over, over the years.

• 14:15Guy Raz?

  What, how did you become interested in acting? Did that start in high school?

• 14:19Speaker 01

  That actually started in elementary school. It started in Maryland. I remember the exact moment was being cast as Demetrius in our fifth grade play. And I was like, I'm the only girl cast as a boy. But this play is kind of cool. And when I'm on stage, people are laughing in a way that I intend them to. And I feel good at this.

• 14:43Guy Raz?

  And did you, I mean, when you were on stage, what was it about? I mean, because it's, it's scary to get on stage as a kid and as, even as an adult, right? Was it, did you feel comfortable in front of people performing?

• 14:56Speaker 01

  I did. I didn't feel that fear as a kid. Like, I definitely feel, feel that fear as an adult more than anything.

• 15:03Guy Raz?

  Yeah, because we're more, we're more afraid of being judged.

• 15:05Speaker 01

  Absolutely. And kids, you're just like, oh, we're doing you a favor. Our teacher told us to perform and we're entertaining you. So you're happy that we're here. And there's just an escapism and, that I've always admired about trying on someone else's personality, trying on someone else's skin. And, you know, it's, people talk about it all the time. It's really liberating to just not be you for a moment, to be in someone else's head.

• 15:32Guy Raz?

  Yeah. What, did you do any plays in high school?

• 15:35Speaker 01

  I did, I did all four years. I had an amazing drama teacher who was really intentional. It was a Jewish drama teacher who was intentional about making sure that we were well versed in, you know, some of the Black and Latino playwrights. And he just introduced me to a whole new world of theater and was so passionate about it.

• 15:57Guy Raz?

  And when, when you were in high school, did you already start to think about, maybe that could be a profession?

• 16:04Speaker 01

  Yeah, when I was in middle school and I moved to LA, I was already writing. I was writing a lot.

• 16:09Guy Raz?

  Where, what were you writing?

• 16:12Speaker 01

  Well, I was writing teleplays. I had the opportunity, you know, I was obsessed with television, starting in elementary school. Like, I had a lineup, I had a program, I knew what I was watching at a certain time. So much so that my mom had to condense, like, you can only do an hour of TV on weeknights. And then it became a half an hour, but I was still sneaky, and that means that I was catching up on weekends. And I just wanted, as soon as I found out we were moving to LA, I was like, oh, my gosh. LA is where Hollywood is and where TV is. Maybe this is my chance to be able to write. And my childhood friend had tickets to Moesha, a taping of Moesha. And to sit in that live studio audience changed my life.

• 16:57Speaker 01

  And I got, I won a teleplay. I won a teleplay of that episode.

• 17:03Guy Raz?

  You won, right, you, this is, Moesha was on UPN, I think, in the 90s.

• 17:07Speaker 01

  Yeah.

• 17:08Guy Raz?

  And, and you went to go see a live taping of it?

• 17:10Speaker 01

  Yep.

• 17:11Guy Raz?

  And they would just give away, like, the, the, the paper script every ep, like, to somebody, somebody in the studio audience?

• 17:18Speaker 01

  Yes, and I got one, and in my hands was the blueprint of how to, to write a sitcom. And I studied that front and back.

• 17:29Guy Raz?

  Yeah, I mean, that must have been amazing, because this is pre-internet. Like, it was, the, the ability to just get that kind of information wasn't, it wasn't available.

• 17:37Speaker 01

  Absolutely not.

• 17:37Guy Raz?

  So you get this hard copy of an episode of Moesha, and you're like, wait, this is amazing. This is how it's done?

• 17:46Speaker 01

  This is how it's done, right in front of me, and I got to see it play out, and I got to, I remember the movements. And the episode's gonna air when it airs, and then I'll be able to, like, follow along. And it really was, like, I started writing right away.

• 17:59Guy Raz?

  So you would look at this, so you could see the script? Because I, I know you've written, you've talked a little bit about this in your book that came out in 2015, about how, like, 90s television really just, I mean, it was, it was the right time and place, because you were that, you were the age where you were watching a lot of TV, and there were all these amazing shows on, including Moesha that you, you loved. And then you had this template to kind of plug in your story using this. This is, as you write, the blueprint, right? And what were you, tell me like what you started to write? What were the stories that you were starting to write?

• 18:33Speaker 01

  Well, I did one original, self stupid. One original sitcom called Ronnie about a middle school boy living in LA, trying to avoid gang violence. Because I had seen South Central, a short-lived sitcom that one of my heroes, Gina Prince-Bide Wood, wrote for.

• 18:54Guy Raz?

  She also did Love and Basketball, I think, right?

• 18:56Speaker 01

  Yes, she did, which also changed my life. So that was it. I was trying to make a funny but dramatic sitcom. And then Cosby came out. I was like, I gotta be commercial. Like, you know, I can't just go out the gate with an original. You know, I have to, I have to pay my dues and show that I could write for an existing show. I don't know where I got that from. But Cosby had just come out with his CBS sitcom. And I wrote an episode of that.

• 19:23Guy Raz?

  And I think your episode was called Tongue Ring, is that right?

• 19:28Speaker 01

  Wow. Yes, yes, it was. It was about, it was about Erica Alexander's character getting a tongue ring and Cosby's reaction to that. Because tongue rings were all the source of judgment.

• 19:43Guy Raz?

  And it was radical, definitely very radical in the 90s.

• 19:46Speaker 01

  Yes, it was.

• 19:47Guy Raz?

  And did you, and you sent that to CBS, right?

• 19:49Speaker 01

  Yeah, and my grandmother taught me, she was very encouraging. She taught me how to copyright it the bootleg way to make sure that no one stole my idea by mailing it to myself first. And then, you know, I did my due diligence and then sent it out with a cover letter as well.

• 20:05Guy Raz?

  Oh, wow. This is like before people, people had LegalZoom, right? Like now people, that's so smart. So you mail it to yourself, then you could prove that it's your IP and then you send it. And did you ever hear back from them?

• 20:18Speaker 01

  Oh, yeah, for sure. I got rejection letters, which I thought was really generous. Because, you know, they can't take unsolicited scripts. And so, in my mind, that wasn't, that wasn't a rejection of my work. So it was still, it was just like, oh, I need, I need an agent. And I'm 12, 11, 12, so I'm not there yet. And I kind of just gave up on it.

• 20:40Guy Raz?

  Who would you, who would you allow to read your stuff when you were in high school?

• 20:44Speaker 01

  I was always, I was definitely protective about letting people read my stuff.

• 20:48Guy Raz?

  Because it's really personal.

• 20:50Speaker 01

  It is, and you don't want, and even now, I feel that way. Like, I don't want, 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 moment when you finish and you're like, man, I did it. And I, I mess with it. I love it. Like, for someone else to taint that, I was very aware of, of that, and really insecure about that. And I remember I did let, like, my, I let my high school best friend read one of my scripts. And she was really, she was positive, but she was just like, is this about you? And I didn't like that question, because it was like, the main character that I had written was,

• 21:34Speaker 01

  you know, kind of based on me, and was a projection of a lot of my insecurities about myself. But her asking that directly, I was like, you, you're supposed to, like, follow the character. I wrote about a very specific character. And I just didn't like that feeling. And I don't think I let anybody else read what I had to write until I had to. I absolutely had to.

• 21:56Guy Raz?

  So, I know, I know that, that after you finished high school, you went, you went to Stanford for college. And how did you feel as a student at Stanford at that time? Because I've, I've seen you quoted, you know, kind of talking about it, how it just wasn't diverse, right? I mean, you get to this place, it's 2003. It's, of course, this world-class school with all these resources, and computer labs, and great professors and all this stuff. But, but, but it sounds like maybe, at least initially, you felt isolated there.

• 22:29Speaker 01

  I, well, the opposite. I think I, I isolated myself in, in a bubble, because I was used to being around, you know, predominantly black people, and... Ultimately, I just didn't really, I wasn't interested in being outside of that bubble and really sought like my community. And so I found myself like really just craving what I had and what I grew up with. And the drama department at Stanford was not as catering to people of color

• 23:04Guy Raz?

  Yeah.

• 23:04Speaker 01

  as my drama teacher was. And so like even the productions that were putting on didn't really appeal to me. I wasn't a big musical person.

• 23:13Guy Raz?

  Right.

• 23:13Speaker 01

  So I was just like, ugh, this is not for me. But luckily, a girl was, had started like this theater company just to put on her own play. And she put on a hip hopera and cast me as one of the leads. And that experience was incredible, just to watch her pull the resources together to make it happen. And also seeing that she was an amateur in the space, it just made it like less intimidating for me to feel like I could do it too.

• 23:45Guy Raz?

  But it sounds like from, from what I've read, like that community of friends that you had, that was kind of the beginning of grinding through ideas that would eventually, you, you have to go through that to get to what you would eventually get to. Like you really started to, I mean, you mentioned acting in theater, like you mounted a, a performance of School Days, like you were, you put on a stage adaptation of, of that Spike Lee film.

• 24:10Speaker 01

  Yeah, that was my first production and the community behind that, like so many people even just in that play that helped me produce it, that were in it are still heavily part of my community right now. But yeah, that started the, the run of four years of putting on productions, like terrible productions, but still productions.

• 24:30Guy Raz?

  Still, yeah. Well, yeah, I mean, there's no way that, that you get to a, a place where with zero experience directing and producing and you're gonna do it well, like, and that's the place to do it, right?

• 24:40Speaker 01

  Yeah.

• 24:41Guy Raz?

  When you're 18, 19 years old. To try it out, and that's how you learn how to do it presumably.

• 24:46Speaker 01

  Absolutely, and I really credit Stanford for being such a welcoming place to do that. And I think it was so welcoming because, you know, that wasn't the focus. 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.

• 25:07Guy Raz?

  Because their theater program is so...

• 25:10Speaker 01

  Elite, you know, and their film program and all of it, you know, that people go there who are extremely talented and kill it. And I feel like I might have been intimidated. But to do something like that at a school where that's not the focus made things, it increased my confidence.

• 25:30Guy Raz?

  As you can imagine, I hope this isn't mortifying to hear, I've watched a lot of your videos from college.

• 25:36Speaker 01

  Oh, my God. What, you know?

• 25:40Guy Raz?

  They're available to see, and they're, I mean, they're fun. You have to, as you say, like, I'm sure part of you is sort of embarrassed to see them. But like, you can also see the beginning of a performer and a writer developing. And you would do this, like, you would start to, you and friends would just kind of make videos of songs, and you would upload it to the internet.

• 26:02Speaker 01

  Yeah, because it just felt like such a, it felt like such a small community, you know, it felt like, nobody's thinking, nobody was thinking about the longevity of the internet in those days. You just weren't, when you're uploading a picture, when you're making a video called F U B, you know, like, you're not thinking about the fact that this will live on and that ultimately, which happened, a friend of mine was in that video and was like, girl, I'm trying to get jobs, can you please take this video down? Like, we're out of college, it's over.

• 26:34Guy Raz?

  And would you, would you, would you, like, because this is pre iPhones too, would you just film it on like a camcorder?

• 26:38Speaker 01

  Yeah, a camcorder that was readily available in our school's library. I constantly checked that camera out just to record and then, yeah, then use the firewall cable to put it on my laptop.

• 26:53Guy Raz?

  Oh, yeah, the firewire.

• 26:54Speaker 01

  Firewire, thank you, Jesus, it's so long ago.

• 26:57Guy Raz?

  Right, because it was like the, I remember there's like the fastest way to get something from a camcorder to your Mac, right?

• 27:02Speaker 01

  Yeah, and it was just, it was so arduous, but at the time, you were just like, I'm gonna make... I'm gonna make magic. Nobody else is doing this.

• 27:11Guy Raz?

  And you, I mean, you were doing other things, like you started a mockumentary series called Dorm Diaries. I guess it was like kind of maybe partially inspired or similar like The Real World on MTV.

• 27:22Speaker 01

  Oh, yeah. I guess that must have been where I got it from. So The Office wasn't, I wanna, no, The Office wasn't out by that time.

• 27:30Guy Raz?

  Yeah, I think maybe the British version was out.

• 27:32Speaker 01

  Yeah. So I think it was definitely a combination of The Real World and the mockumentary style of The British Office.

• 27:40Guy Raz?

  You worked on this with your friend Tracy Oliver. It was a college friend who had gone to become well-known in her own right. Is writer and a producer. And tell me what you would do. Like you would give scripts to like a bunch of different friends and you would shoot scenes around campus or in dorm rooms or just anywhere?

• 28:03Speaker 01

  Yeah, so I wrote the script and just gave, like, cast my friends. One of the friends that I ultimately cast was Tracy. Yeah, then I would just go and film it, take up like 30 minutes of their time, maybe max an hour, and then I would edit it in my spare time. And the response was amazing.

• 28:26Guy Raz?

  Yeah, you put it on Facebook and people, like, first it was presumably people you knew, but then soon people you didn't even know were commenting on it.

• 28:33Speaker 01

  Yeah, it started to spread to other college campuses that had, you know, either black dorms or BSUs. We're just like, this is my college experience. And they felt seen.

• 28:48Guy Raz?

  You said in an interview several years ago that that experience was a lightbulb. It was your, you called it your epiphany moment. Why?

• 28:58Speaker 01

  Because I had spent all this time trying to write and send my work to

• 29:08Speaker 01

  Either producers, executives, contests, whatever, in an attempt to get it made, to get it seen.

• 29:16Guy Raz?

  Yeah.

• 29:16Speaker 01

  And I was either told why there wouldn't be an audience for this particular work, or that, you know, they just didn't want to make it. And so to be able to just literally write something on the fly, cast my friends, record it myself, edit it myself, put it out there, and have an immediate audience that liked it, that wanted more of it, was just so validating in a way where I was like, I can keep doing this if I want to. Yes, it's a smaller scale. No, it's not television. But if I'm really serious about like, writing and getting my work seen, this is a viable way to do it.

• 29:57Guy Raz?

  All right, so you have this project that you do. And I know when you graduated, you went to New York, you got a fellowship at a place called The Public Theater in New York. And I guess while you, while you, sort of soon after you got there, you, one of the ideas you had was to maybe pitch Dorm Diaries and see if you could maybe MTV or BET or somebody would be interested in helping you turn it into like a professional show.

• 30:24Speaker 01

  Yeah, I wrote like the spec script of what the television show would be. And then my brother had a friend who worked at, I want to say VH1 at the time. And I was begging him like, give me a meeting with her, give me a meeting with her. So all those, I was just trying at the very same time while I was working at The Public Theater to get that off the ground.

• 30:46Guy Raz?

  It's a really tough time in life because you're like 22, it's, you-

• 30:51Speaker 01

  Broke as hell.

• 30:52Guy Raz?

  Yeah, and it's really hard to get anybody to take you seriously. And you're in New York and it's expensive. And it's stressful. Do you remember feeling anxious about just life?

• 31:03Speaker 01

  Oh, without a doubt. Anxious about life. I was living in the worst apartment. I was watching my friends on these very clear paths to me to do what they wanted to do. I would feel incredibly insecure just about where I was because I was essentially- You know, making videos, just trying to make ends meet, taking odd jobs. In the theater world still, but there was just like no progress to me. You can't really measure progress in the same way that you can measure like, oh, you're in your second year of law school, you're about to take the bar. Oh, you are now a diplomat. Oh, you're doing, and that was just like, damn, everybody's killing it. And maybe my dad was right, maybe I did.

• 31:48Speaker 01

  Maybe I should have had a backup plan. Maybe I should have taken college more seriously so I could have something to fall back on. And that began my process of studying for the LSAT. And then ultimately the GMAT, just to be able to get a master's like he wanted me to do so badly.

• 32:06Guy Raz?

  And I know that at one point you invested a little bit of money in some film and editing equipment, and then it was stolen, like your apartment got broken into.

• 32:14Speaker 01

  Yeah, my apartment got broken into the night before I was supposed to go pitch. And like my computer was stolen, everything, the film equipment. I was editing this guy's movie and he gave me, which he had not done before. He gave me all of his original tapes and they stole those tapes. And that was like his life's work. And I felt so bad about that. I was like, why would they steal tapes? And the way, the way I had my camera set up in my bedroom, it was on a tripod. And it was like pointed towards the bed and I, somebody was like, they probably thought I was porn, like they were stealing porn tapes. And I was like, damn, they're gonna be so disappointed when it's just like a Jamaican movie.

• 32:58Speaker 01

  So I felt really, really bad for him. And then of course hated that all of my, everything, everything was stolen. It's such a violation. And of course my roommate's stuff and you know, we just felt so helpless.

• 33:12Guy Raz?

  I, I read that you also describe yourself as an introvert. And I, I'm trying to like picture you 22, 23, trying to, you know, talk about the work you've done and to try to pitch it and to try to get meetings and, but also being an introvert, that's really hard.

• 33:29Speaker 01

  Extremely.

• 33:30Guy Raz?

  Yeah.

• 33:31Speaker 01

  To put yourself out there, which is like what everyone tells you. You just gotta put yourself out there. Do you know how hard that is?

• 33:36Guy Raz?

  So hard.

• 33:37Speaker 01

  Like especially when you feel like, you know, what are you putting yourself out there? How do you go up to someone and talk to them about what you do? I'm always. Deathly afraid of imposing on people, like taking up their time and asking people to watch something. So being vulnerable in that way, like I need you and I may potentially need something from you, but I don't know what I have to offer you.

• 34:03Guy Raz?

  Would you write things down in a diary?

• 34:06Speaker 01

  All the time. The diary, the journal, because that's what makes sure people say. The journal was like my, my therapy. But people could also tell, you know, I, I think part of being an introvert, part of being even insecure is you're constantly aware of the way that people view you. Even like questions that acquaintances might ask me about what I was doing, they just felt like, like I was being judged. And almost throwing my life away. And whether or not that was true, that's I guess how I felt inside. But I definitely wrote to cope.

• 34:44Guy Raz?

  I mean, what's amazing, and we're going to get to this, is I think anyone listening can kind of connect the dots, which is you were and are, both of us, we all, everyone listening, we live in an extrovert's world. It is a world, let's just acknowledge that. The world is dominated by extroverts and introverts have to figure their way, how to navigate that world. And, but you, you, you were writing and you were aware, you were self-aware. You knew that you were introverted. You felt awkward. You felt insecure. Those would be the themes of what, you would turn those into powers.

• 35:16Speaker 01

  I think once I realized, like, like, you're not the only one that's going through this. You're not the only one that feels this way. The more people, I, I realized people felt the same. And I was like, this is kind of an identity. And I'll never forget writing those words in my journal in New York. Just, I'm awkward and black. And I shared that as a Facebook status. My friend Tracy was like, ha, ha, ha, those are the two worst things anyone could be. And I just found that hilarious.

• 35:47Guy Raz?

  What did you, what did it, what did it mean for you to feel awkward and black? How did it, how did that, um, like, what were things that, that made you feel that way?

• 35:57Speaker 01

  Well, what we just discussed about feeling ridiculously uncomfortable to just even go out to someone and introduce myself, the small moments in life that either made me feel uncomfortable or irritated me, and just, you know, how many of those things also had to do with my blackness too. And that realization just kind of made me laugh. And the, the fact that those two didn't necessarily intersect, um, often even publicly in images that I'd seen in media. And that, that, that was something that I wanted to explore. I felt, I felt special for realizing that and felt special for having that identity and also wanted to find my tribe. Like who else, who else identifies the same way?

• 36:43Guy Raz?

  Well, that's the thing. Like, a lot of times, in, in that case, people would internalize feeling awkward, right? Like, you wouldn't express it, you wouldn't put it out there. But you did share that, that idea. I mean, which is a risk. I mean, putting yourself out there is, is kind of scary.

• 36:58Speaker 01

  I just didn't, well, I wanted to know that I wasn't alone. And I, and that was the first iteration of that idea after I wrote it down was like, oh, I'm gonna make T-shirts. And to me, even T-shirts are like, if people are out there wearing, then you can point out someone else who identifies that way and is the conversation starter. Or even, even, even if you don't start the conversation, it's a way to feel like, oh, I'm not, I'm not alone in this. That person over there is awkward too. So in a way, it's a defense mechanism to outwardly claim it before someone else claims it about you. Um, and also just be like, look, I know what it is, guys. Okay? Just bear with me. I've already said what it is. Like, we've gotten that out the way.

• 37:34Guy Raz?

  What, what prompted you to leave New York and move back to LA?

• 37:39Speaker 01

  My friends, and that was another revelation, visiting LA. I want to say I came maybe for a graduation or something and I caught up with Tracy and my other Asian friend, Ashley, and we went to the beach one day. And they were just like, girl, why are you still in LA?

• 37:54Guy Raz?

  In New York, yeah.

• 37:55Speaker 01

  Yeah, you know, I'm out here trying to become an agent. Tracy's out here, you know, in the producers program. And you're all the way in New York. We could be working together. Like, come to LA. Everybody you know is here. You can save money. And I was just like, yeah, why am I out here? I'm kind of wasting my time. It's not, I haven't failed if I come back home. And so that was like, yeah, I'm, nothing's keeping me here. I might as well go home and see what I can do.

• 38:29Guy Raz?

  When we come back in just a moment, how Issa built a giant fan base with Awkward Black Girl, a show that gets boosted by Kickstarter campaign and a phone call from Pharrell. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 39:00Guy Raz?

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• 39:42Guy Raz?

  The agents bring speed and scale, and people bring taste, judgment, and control. Learn how you can get more out of your site from a Framer specialist or get started building for free today at framer.com/built for 30% off a Framer Pro annual plan. That's framer.com/built. Rules and restrictions may apply.

• 40:06Guy Raz?

  AI isn't just opening new business opportunities, it's changing the way businesses get work done. The questions they ask, the decisions they make, the routine tasks they can hand off. That's the idea behind NetSuite Next, the next generation of NetSuite with AI woven into the tools your business already relies on. NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together, and that shift is already underway. That's why NetSuite wants to put a new,

• 40:51Guy Raz?

  expert-created business guide in your hands today. It's called "Aligning for the Agentic Era: How AI is Changing Everyday Work." And right now, it's yours, absolutely free. Inside, you'll discover how AI could reshape work across your entire organization, and how to position your business to prosper from it. If your revenues are at least in the seven figures, get NetSuite's free business guide, "Aligning for the Agentic Era: How AI is Changing Everyday Work", at netsuite.com/built. The guide is free to you at netsuite.com/built. netsuite.com/built. Stripe is built for whatever comes next because the pace of change

• 41:35Guy Raz?

  has never been faster than it is right now. New business models, new currencies, and new expectations for speed, reliability, and scale. Stripe builds financial infrastructure that helps businesses start, grow, and operate globally. From payments and billing to fraud protection and cross-border payouts, Stripe is built to support the new pace of commerce. They're trusted by the companies building at the frontier, from 86% of the Forbes AI 50 to global leaders like Salesforce and OpenAI. In fact, more than 1.6% of global GDP flows through Stripe, with Stripe's users

• 42:17Guy Raz?

  processing a combined $1.9 trillion last year. So if you're already thinking about what's next for your business, see what's possible at stripe.com.

• 42:37Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2009, and after trying to get her career off the ground in New York, Issa Rae decides to move back to LA, where at first, she moves in with her mom.

• 42:53Speaker 01

  That was hard.

• 42:55Guy Raz?

  Yeah.

• 42:55Speaker 01

  Oh, that was hard, because she just treated me like I had never left.

• 43:00Guy Raz?

  Right. And you're like, in your 20s.

• 43:03Speaker 01

  Yeah, I'm 24.

• 43:04Guy Raz?

  You want to start your-- yeah, yeah.

• 43:06Speaker 01

  And she's waking me up in the middle of the night because I had left dishes in the sink. And I was just like, first of all, yes, it's disrespectful on my end to like, come home and leave a mess. But come on, I'm not 16 anymore. Like, what lessons are you teaching me? I can get up in the morning and wash it. Like, treat me like the adult that I am. And in her mind, she's like, you're not the adult that you are until you're out my house, you know, and I'm not paying-- you're paying your own bills. So it was really, really humbling and frustrating.

• 43:36Guy Raz?

  Meantime, you were still experimenting with video. Like, you were still, like, with all this stress and all of the, kind of, that anxiety of feeling like you weren't going anywhere, you still had enough motivation to make little-- like, you started on a web show called The F Word, which was kind of a-- it was your brother was in it and his friends. And tell me about just making that. Was it kind of just a fun side project to do? Or did you think-- what were you thinking about that?

• 44:10Speaker 01

  Yeah, when I-- I will credit New York for giving me that hustle mentality. 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, it's coming. I got you, I got you. New York, I'm working on a script. Where is it at? It's right here. And I got this, and I got that, you know? And like, they're just, they're ready. And so there was part of me that didn't want to be the flaky LA person. So I realized, like, I have to show and prove. I have to get my hustle on. Like, I have to, I have to work, and I have to make these opportunities for myself. And I have to be ready at a moment's notice.

• 44:50Speaker 01

  And so my brother had this music group. I asked if I could do his music video. And he was like, yeah, if you're gonna do it for free, absolutely. And when I was on that music video set, they were so funny together. You know, I was just like, y'all are talented, but you're also funny. And you're funny together. I want to make like a show around you.

• 45:13Guy Raz?

  So, yeah, so you would work all day and then you would spend your nights writing scripts for the F word?

• 45:19Speaker 01

  Yeah, I wrote outlines to their credit, like, so I'd give them the story points, where to go. But I never told them what to say. They just got it and they would improv their way through those story points. And I'd edit it together and stay up, you know, editing it.

• 45:34Guy Raz?

  All night?

• 45:35Speaker 01

  All night and make sure, I'd make sure that it come out at the same time every Monday morning, F word Mondays.

• 45:43Guy Raz?

  And you would film it and write it and edit it and do everything yourself in your computer?

• 45:50Speaker 01

  Yep.

• 45:51Guy Raz?

  It's a lot of work.

• 45:52Speaker 01

  It was, but it was so fulfilling because it was like mine. It was their talent, but my work. It was, it was such a good boot camp for me. You know, I really, I really cherish that time.

• 46:04Guy Raz?

  I mean, not to, not to bring my story into it, but it just reminds me so much of when I started out as a writer 25 years ago and writing. And, you know, I couldn't get any of my work published, but I would just write and write and write and so much of it was bad. But, but I had to write that stuff in order to be able to eventually make stuff that was good. And, and I, I mean, you did this for seven seasons. You made seven seasons of the show.

• 46:28Speaker 01

  Yeah, seven seasons over, I want to say, three to four years. But like to go back to you, like, there's still a point where you're like, okay, this is bad. This is not great. But you're still encouraged by the fact that you're, you're doing it and you feel good about doing it. I'm not sitting back and it's like, I'm, I know that I'm only going to continue to get better. And there's something satisfying in that. And then at one point. You sit back and you're like, I think this is good.

• 46:54Guy Raz?

  Yeah.

• 46:54Speaker 01

  I think I did something. And the satisfaction of creating something from scratch, and even just having the idea and executing it, is like, is like no other to me.

• 47:07Guy Raz?

  All right, you had written in your diary, "I'm Awkward and Black." And did that idea just kind of go away for a couple of years? Or did it always kind of, I don't know, was there any connection to it becoming a show? Or was it just, it was just you expressing your innermost thoughts?

• 47:24Speaker 01

  Yeah, I mean, so as you know, sometimes you'll write something down and be like, oh, that's something, but I'm not ready for it yet. But it's something and I'm gonna come back to it. And it'll just stay in your head. It'll pop up occasionally when you're working on something else. And for me, I had a vision, like I told you, I had the initial idea to do T-shirts. And then ultimately, a couple of weeks later, it was like, maybe this is an animated series. And I was stuck on that. I was like, oh, I want to do an animated series for this. And oh, man, animation costs so much money. I'm not ready for it yet. And so, again, kept working, kept working. And then this article came out that was asking for my, the character that I imagined in my head, the Black Liz Lemon. They were like, where is the Black Liz Lemon?

• 48:09Speaker 01

  And where are these quirky black characters? And that lit a fire in my ass. Because I was like, I was like, if I'm reading this, someone else is gonna read this and do my idea before me. I can't wait for this to be done in the way that I think it's supposed to be done. Like, it can be a live-action series. And I can just make this for the internet and just get it out there for now.

• 48:33Guy Raz?

  Which is what you did. In 2011, you put out your first episode of Awkward Black Girl.

• 48:41Guy Raz?

  And I mean, by that point, I mean, you knew how to do it, right? I mean, I've, I've watched many, many episodes, including the very first one, which is remarkable because it's really funny. And it's the first one and the, the production quality changes so much very quickly, right? Like, the first ones are very much DIY. But, you know, like, you're in a car, like, you have somebody filming you. Then there's somebody filming the, the character in the next car. You know, that first scene, it's like, did you, are you ever in a situation where somebody's driving next to you and like, they know you and they're like, trying to talk to you and it's awkward and it's so funny? And like, that was the first one. And, and so you knew how to just create something, even, you know,

• 49:24Guy Raz?

  you know, even as sort of simple compared to what it is now or what you do now. But you knew how to do that by that point.

• 49:29Speaker 01

  I did. And that got rid of the excuses I kept coming up with. Because for me, this was like, this was my big idea.

• 49:38Guy Raz?

  Yeah.

• 49:39Speaker 01

  Now I just wanted to be out before I'm kicking myself because someone else didn't wait. And so, once I was like, this has to be out, then the notions of perfection went out the window. I still like, was like, okay, I'm still gonna make sure that it's funny and good to me before I put it out there, but I'm less precious about it being completely perfect. And, and that came down to even casting myself. Because I wanted someone else to be, to play Aqua Black Girl. The, the lead in Dorm Diaries is who I wanted to play Aqua Black Girl. She was in DC, she was in law school and she couldn't do it. And then I hadn't acted in so long, the fear of putting myself out there was holding me back again.

• 50:21Speaker 01

  I was like, ah, do I really want to be in this? Do I want to be at the mercy of the internet in the same way I've seen my little brother and his friends be at the mercy of the internet? Am I ready for that? Can I take that? And ultimately, like, the, getting the idea out there was more important to me than being scared of being geiged on the internet.

• 50:43Guy Raz?

  I mean, obviously, this is a business show, but this is such a business experience. Like, you have this problem, you need to cast somebody, you can't solve that problem, except you can. And you did by basically just saying, all right, I'll do it reluctantly, but you knew that you just had to solve a problem. You needed a human being to play Jay. And you were, it was, the easiest solution was just to have you do it.

• 51:08Speaker 01

  It was, and I knew what the character was. That was it. Like, I was like, problem solved.

• 51:14Guy Raz?

  Yeah, I mean, in those first, certainly, and for people who haven't seen it, it basically follows this character Jay, who's a telemarketer and is awkward, has these awkward encounters in her life. And also, you hear her inner dialogue, or monologue, I should say, and it's sort of interspersed and edited as you see these scenes. And how did you, I mean, you didn't have a lot of expensive equipment, and you were funding this yourself, so were you just like, kind of shooting in the daytime with handheld cameras and occasionally a tripod and maybe some like boom mics?

• 51:49Speaker 01

  Boom mics? No, I wish. I don't even know what we're doing for mics. Those first couple of episodes, it was just a camera and whatever sound the camera picked up.

• 51:59Guy Raz?

  Captured. OK, the mic for the camera, OK.

• 52:01Speaker 01

  Yeah, and editing it. And my little brother, I asked him to create the music for it because I wanted it to have score. I wanted it to feel like as real of a show. It could, but the specificity of like, this is for the internet was in my mind. I was like, I'm not going to try to make this a real TV show. I'm not going to, it's not going to be long, it's going to be short, it has to be short. But it was very produced for the internet in a way that my other projects weren't. I wasn't aware. Like, all the lessons that I had learned from making those other two web shows, I applied to this.

• 52:37Guy Raz?

  You presumably, I mean, you're funding this yourself, and it's, even though you were doing it on the cheap, like, you still had to cover costs, and so... You were running out of money pretty quick, I think, within like the first few episodes.

• 52:51Speaker 01

  Yeah, I mean, the first few episodes, I was, it was just friend favors, right? So those first three episodes. And by that time, I had cast my friend Tracy to play my nemesis. And she was in school for producing. So she was like, let me help you produce this. And let's bring on a real crew, write the scripts in real format. And so she got a crew via favors to start helping me and just elevated the look of the show. And that's what started getting expensive.

• 53:23Guy Raz?

  Yeah.

• 53:24Speaker 01

  And my friend at the time was telling me about Kickstarter. And I dismissed it. I was like, I'm not raising money online. That's, that feels so desperate. And then our cinematographer Shay, he brought it up and was like, I heard it. Have you heard of this thing called Kickstarter? And that's when I took it serious. So I was like, okay, more people are saying this. Maybe this is a viable way to try to raise money. And we asked for $30,000. And then over 30 days, you know, people almost helped us to raise almost 60. And that's when it felt like, wow, people care about this show. Like, you know, and we, we, we didn't give an ultimatum, but before this episode that we knew would make a, make an impression, we put like a, we basically asked our audience.

• 54:09Speaker 01

  We told them like, this has been for free. You've gotten seven episodes and we can't afford to make this any longer. So if you want to continue to see this show and you want to support us, please give us whatever you can.

• 54:21Guy Raz?

  Yeah. And by the way, at that point, those first sort of three, four episodes, how, how many people were you getting? Cause this was still new. How many viewers were you getting per episode?

• 54:33Speaker 01

  I actually don't remember. I know that was above, it was, it had to be between 30,000 and 50,000, maybe 100,000.

• 54:40Guy Raz?

  Wow. How were you getting so many viewers? That's amazing.

• 54:44Speaker 01

  We released it the first Thursday of every month. And that was like a release schedule I just came up with. I, when I was, when I released the first episode, I just. I was like, okay, I did it. Woo, got ahead of the idea.

• 55:00Guy Raz?

  Yeah.

• 55:01Speaker 01

  Got it out there. And then that episode got like 25,000 views in the first week, I want to say. And I remember the guys from the F word hitting me up like, what the hell? How is this getting more views in this show we've been doing for four seasons? Five seasons now? And I was like, I don't know. It's just, I guess people are really identifying with it. And now I have to do another one. And so it was just, yeah, it really spread by word of mouth in the best way.

• 55:29Guy Raz?

  Were you, were you focusing? Like, we've had people on the show who started, you know, who like really focus on like search optimization or like certain words or things like our titles in the YouTube video or descriptions. Were you, were you focusing on any of that?

• 55:44Speaker 01

  No, unfortunately, I was not. I wasn't aware of that. I released it on Facebook to my friends and I didn't, I didn't really try. And it was my friends and the network of friends who, who spread the word.

• 55:56Guy Raz?

  Wow.

• 55:56Speaker 01

  And, and yeah, you can amplify that. 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.

• 56:09Guy Raz?

  Yeah. I mean, you raised $50,000 in this Kickstarter campaign and you started to get quite a bit of attention, including from Pharrell Williams, who I guess reached out to you because he was interested in maybe collaborating. I mean, that must've been kind of mind blowing to get an email from, or whatever, like a message from Pharrell Williams saying, hey, can we talk?

• 56:30Speaker 01

  It was extremely mind blowing. We had already gotten like, you know, some great celebrity support. Gabrielle Union, I want to say, was one of the first people to like support it and spread the word about it. Ava was an early supporter. But Pharrell was the first person to like call me and be like, I wanna, like, I want, I want in. I want to figure this out. And he had this, you know, when Google did the 100 channels and gave various creators, whether they were YouTube stars, established musicians, they gave channels and they put funding behind those channels, trying to make like the new TV on the internet.

• 57:10Speaker 01

  He had one of those channels and was able to fund our second season via his I Am Other company.

• 57:19Guy Raz?

  So what did that mean for the season two? Like, because you can see it, like, it's so cool to see the evolution of that show from the first episode to the fifth and sixth. And then season two is like, I mean, it's a television quality show.

• 57:33Speaker 01

  Yeah, I mean, it meant we were funded. Yeah. It meant that we could properly pay people. It meant that we could budget. It became an actual production. You know, like, the second season, we were actually able to pay people like a legitimate rate. Like, it was a production. And they weren't, like, getting rich off of it, but it was like, OK, I'm being compensated properly for my work.

• 57:57Guy Raz?

  Did you feel after that show started to get attention and you're collaborating with Pharrell Williams, that, OK, did it, like, sort of lessen your anxiety? Did you start to feel like, OK, now I feel like there's direction, things are clicking? Or did it actually increase your anxiety because now you were on a bigger stage?

• 58:17Speaker 01

  It increased my anxiety for sure. I mean, as these things go, like, you're like, oh, now people have expectations. They're like, oh, you got money now? Oh, Pharrell's missed you? I know y'all better come hard. And I felt that in so many ways. I just started realizing this about myself, but sometimes when things are successful, I will minimize my part in that and attribute it to other things. Part of it is the imposter syndrome of it. Part of it is just the fear that you have one good idea and this is it.

• 58:59Guy Raz?

  Yeah.

• 58:59Speaker 01

  This is all that's in me. And so even with Awkward Black Girl being successful, I was like, this, this wasn't just me. And let's make sure that everything else is amplified, amplify other characters. And let's also make sure that, you know, this person is highlighted and taken care of. And like, let's increase all the other factors because it couldn't have been me. I don't know how to properly explain it, but that's something that I've realized I do even, you know, in other work. And it took a realization and even other people to just kind of make me focus, like, this is, there's something that you did and you have to focus on that and you have to embrace that. It's you.

• 59:43Guy Raz?

  When we come back in just a moment, how Issa eventually creates a hit series for HBO, but first discovers just how much it can suck to try to launch a show in Hollywood. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 1:00:17Speaker 02

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• 1:01:59Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2012, and the show Awkward Black Girl is getting a lot of attention, not just from fans, but from other creators and producers in Hollywood. And Issa gets invited to pitch some new ideas to some pretty powerful people.

• 1:02:18Speaker 01

  The most exciting thing that happened to me was being able to pitch for Shondalee. And Shonda Rhimes, to me, huge inspiration. Had Grey's and Scandal at the time, killing it just as a Black woman showrunner. And I got to pitch to her and Betsy. They bought a show idea that I had called I Hate L.A. Dudes. And that was an idea that I pitched on a whim in a general meeting with them that I had just-- that was gonna be my next web series. And they really responded to it. They laughed. And they were like, yeah, we want to develop that with you. And then I got the grand announcement that I was gonna be doing, developing Shonda Rhimes' first comedy.

• 1:03:02Speaker 01

  And that was a big deal to me.

• 1:03:04Guy Raz?

  I mean, this is like 2012. You launched your web show in 2011. I mean, that's amazing. Like, you were pitching Shonda Rhimes. Like, how crazy was that to sit in a room with her? I've met her before. She used to go to the TED Conference a lot. And I used to go because I did a show with them. And like, she's the nicest, just like, just very approachable person. But still, it's Shonda Rhimes.

• 1:03:28Speaker 01

  It's Shonda Rhimes, and she's intimidating as hell.

• 1:03:31Guy Raz?

  And she is like, one of the most successful showrunners in history. So you're there, like, a year after you launched this, maybe less than a year after you launched this thing, talking to her in a room. Like, what do you remember about that?

• 1:03:43Speaker 01

  You know, I didn't realize that it was a year. That is kind of crazy. But in some ways, it felt like, oh, my gosh, this is-- This is it. I'm finally here.

• 1:03:51Guy Raz?

  Mm hmm.

• 1:03:52Speaker 01

  And this is my opportunity, like, being in that meeting for the first time, I was nervous and, you know, like, they were just so, so warm and welcoming. Betsy Beers is one of the funniest people ever, and so they put me at ease with their jokes. And so, once they were like, oh, we want to do this with you. I was just, I was on cloud nine, and I worked up the courage to ask Shonda for a picture. And she was like, you want a picture with me? And I was like, uh, yes. So I still have that picture.

• 1:04:20Guy Raz?

  You still have it? Oh, wow.

• 1:04:21Speaker 01

  Of course, man. And so that was like, that was amazing to me. And then, you know, it's one thing to get the blessing to do the show, and it's another thing to make it. And that was terrifying, because then I was just like, oh, no, I'm gonna let Shonda Rhimes down.

• 1:04:41Guy Raz?

  And this was a show called I Hate L.A. Dudes, and it was sold, the ABC want was basically about the concept.

• 1:04:49Speaker 01

  Yep.

• 1:04:50Guy Raz?

  And so you start to work on a pilot.

• 1:04:53Speaker 01

  I started to work on a pilot, and that was my first real television pilot process.

• 1:05:00Guy Raz?

  And what, how'd it go? I mean, how were you, was it just you in a room, or were you working with Tracy, or were you working with? Yeah, how were you writing it?

• 1:05:09Speaker 01

  This was just me. This was me. By that time, Tracy was writing on a, on an ABC show. And so it was me working with one of their development executives at the time, and directly with Betsy Beers, because, you know, Shonda, she's the queen of drama, and Betsy was the head of comedy there. And I loved working with them. Their feedback was great. And then it was like, let's submit it to the studio and the network. And that was like a foreign concept to me. So I was like, okay. So the studio and the network are different. The studio gives me notes. I work on them. Give it back to the studio, then it goes to the network. They give me notes. Those notes could be conflicting.

• 1:05:51Guy Raz?

  There are a lot of cooks in that kitchen. Wow.

• 1:05:53Speaker 01

  There are so many cooks. And they don't all agree. And so to someone who just wants to please, it can be maddening. And for me, like, I don't think that I had a concrete vision enough. 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. And so I was just like, okay, they gave me this note. I'll make the note work. Okay, now the network's giving me this note that conflicts. I will make that work. And it just became a pile of mush. It became a pile of like, a show that didn't really have a real point of view. I wasn't represented in it.

• 1:06:39Speaker 01

  And I just, I kind of just didn't know what I was doing. And I credit, you know, Shauna Lan, they were just so positive about the experience and positive about working with me. And they saw something in me that I just really didn't see in myself. But ultimately, the network passed on the project. And I have not even gone back to revisit that script. I don't even know what it would be.

• 1:07:03Guy Raz?

  I mean, the show was called I Hate L.A. Dudes. It was about, about, about a woman who was dating horrible, awful image obsessed men in Hollywood. And I guess you, from what I understand, like, you had tried to kind of mold it in a way that you thought would be acceptable to a network, which was like, they're, you know, in the end, everyone gets to come together. And then you sort of, you kind of like the characters, but it's called I Hate L.A. Dudes.

• 1:07:35Speaker 01

  Yeah, yeah. And what's, what's crazy is I like was prepared to make that show for the internet. And if I had made that show for the internet, I know what it would have been. I know what I would have been able to do. It would have been a series of encounters and dates and sketches. But the way you write that is different than writing a network show, which needs to have a specific format and act breaks. And it needs to play out over seasons and it needs to have multi-character arcs. And that was something I didn't quite understand. In the same way at the time, like, I didn't really know how to make a good network show yet. I was still in internet mode.

• 1:08:16Guy Raz?

  Tell me, when they ultimately decided not to back up, make a pilot for that show, was that devastating? Did you feel like, OK, well, I'll just move on and go to the next thing? Like, did you feel like it was a, yeah, I mean, was like a gut punch?

• 1:08:33Speaker 01

  It was the most devastating. I blew it. I blew it. I blew my one shot. Shots like this don't happen. Often, the cards were set up for me to succeed. And I only failed myself. I can't blame anybody but me for this not happening. And it was such a public announcement. I think that's also the embarrassing part of working in Hollywood, is you get these announcements of things that are happening and the support. And then they just disappear. And while there's not an announcement that it's not going, you still get those questions.

• 1:09:11Guy Raz?

  How's it going?

• 1:09:12Speaker 01

  Yeah, how's it going? What? It must be great. Killing it. Ah, shawty. And then it's just like, oh, yeah, uh, just a different direction. You know, I was just working on a lot of things. So, you know, maybe just don't ask me. Maybe just don't. Do I ask you about your work every day? No. Do I ask you how your projects go? But no, like, it was just, it was, it was really devastating. And I thought it was over for me. I thought nobody's gonna want to work with the failure who couldn't make a show with Shonda Rhimes. Who couldn't, like, make the layup.

• 1:09:43Guy Raz?

  Were you writing that, about that, in your diary?

• 1:09:46Speaker 01

  Probably. I haven't, I have to check. I have to check. But I definitely remember, I, I, I'm, I don't cry often, but I want to say I cried after that. It was either that or the next HBO failure.

• 1:10:04Guy Raz?

  Because you do, I mean, you do eventually pitch a show to HBO, which was not yet insecure, by the way. It would eventually turn into insecure. Although, I think you already had the idea of basing it around a young black woman working at a nonprofit. And From what I understand, you initially started working on it with Larry Wilmore, the comedian who, of course, created the Bernie Mac shows, on The Daily Show for many years and had his own show. And lots of people know Larry Wilmore and his shows. So how did that collaboration happen? How did that start?

• 1:10:39Speaker 01

  So after I sold my pitch to HBO, they bought this nonprofit idea. Then my managers were like, you know, you're gonna need a showrunner. You're gonna need someone to help you run the show if it gets picked up. And I was like, oh, okay. And so they suggested that I meet with Larry Wilmore. And, you know, I was a fan of his work. And so we met and we really hit it off. I loved him. And he was just like a strong voice and was just really intent on bringing out my voice. And so then, you know, he was attached to the project and helped me to start to write the pilot.

• 1:11:16Guy Raz?

  How? I read that you wrote the pilot in like eight days and then you revised it over a period of weeks. But like, how did HBO respond to this pilot? I mean, that's fast. You have this pilot and you've got this concept and let's go. Let's make it.

• 1:11:31Speaker 01

  So the way it works is, you know, obviously, the deals take a long time. And so to put in place. So like Larry is an established writer, creator. And so working on his deal took some time. And so in that time, we were meeting up and just having conversations on his rooftop. What I didn't know was that was his process of kind of figuring out what I had to say, figuring out my point of view to lend to this main character. And so that was weeks of just kind of a writer's boot camp, a workshop of sorts, that we were able to, from those conversations, write that outline of what this show, what the pilot

• 1:12:11Speaker 01

  would be in like eight days. And they loved it. Initially, they were like, you guys are on the right track. This is dope. And gave us notes on that. But we went to script, which was like a big deal. And then even writing that script was really fast. And then that's when they were just like, this is good. But to them, it just wasn't an HBO show yet. One of the most common questions you get.

• 1:12:37Speaker 01

  That'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? And why are we following these characters on this specific day? What is our way in? And then, of course, where are we going? And I, you know, we were working on it for a couple of years and Larry got the Knightley Show opportunity. And so that was like his dream job. And by that time, he was also helping with Blackish. So I was like, damn, you got all this happening and we're still, I'm still working on this damn show. And I'm gonna lose you. And I did. And when I lost him, I thought.

• 1:13:17Guy Raz?

  That's it.

• 1:13:19Speaker 01

  That's it. Again, here I go again. They're not.

• 1:13:22Guy Raz?

  Yeah.

• 1:13:23Speaker 01

  They're not doing it. But we had, we turned in, this is when I cried. We had turned in the last version of the draft before he had to go. And so I got the call from my managers, like, this isn't, they're still not happy with the script and.

• 1:13:37Guy Raz?

  They were not happy with the pilot. They were not ready to greenlight it.

• 1:13:41Speaker 01

  They were not ready to greenlight what was then known as nonprofit with a P H. No.

• 1:13:46Guy Raz?

  And meanwhile, I mean, you were also kind of on the line because I think around, around this time, you had actually launched something completely different, a whole separate venture, which, which would be the beginnings of a management company, your own business.

• 1:14:01Speaker 01

  Yes. It was called Color Creative and it was, initially it was supposed to be a program for discovering writers. And because of this process, I had, I was like, I don't want writers to have to go through this. I've done the internet model where you can build an audience and you can make a proof of concept. So what if I do this with other writers and produce three pilots for $50,000 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 the time.

• 1:14:33Guy Raz?

  So you had nothing left.

• 1:14:34Speaker 01

  I had nothing left, but I was like, counting on.

• 1:14:38Guy Raz?

  This coming through.

• 1:14:40Speaker 01

  This green light, yes. I was like, okay, well, there's gonna be money coming in. And I was like on set for one of those pilots and I went and walked somewhere and just cried. I was like, I don't know what I'm gonna do. I don't, I've spent all the money I've ever made in my life on these pilots that don't have distribution. And I can't stop it because these writers are also counting on me and I have no next steps. I blew, I don't have a show. I don't have anything.

• 1:15:08Guy Raz?

  Oh, man.

• 1:15:09Speaker 01

  And I've, yeah, I've made a mistake. Like, I put all my eggs in this basket, in these, well, two baskets.

• 1:15:15Guy Raz?

  So you were simultaneously financing pilots that you put all your money in and counting on this, this insecure deal to go through and still.

• 1:15:28Speaker 01

  And so, yeah, then they, they were like, well, we still want to give you one more chance to write it. And they called me in for a meeting and Casey and Amy were just like, these are the parts that we really like. Like, what was your version of like a Laverne and Shirley look like?

• 1:15:45Guy Raz?

  They're talking about the character of Molly.

• 1:15:47Speaker 01

  They're just talking about the character of Molly, yes. It was based off of my real life best friend. And I was like, oh, that's interesting. And then what, what happens if I make it closer to, to my life at the time? And that's when I was like, I'm putting everything on the table. I'm putting everything that I'm going through, everything that I'm feeling in this draft in addition. And that's what they ultimately ended up picking up.

• 1:16:10Guy Raz?

  It's amazing because, and I mean, television's really takes a long time and it really is underscored by this timeline. Because like, you started talking to them in February 2013 to HBO and the pilot debuted in September of 2016. So that must have been just like a stressful three-year period of just like, is it happening? Is it not happening? Is it happening? Will people? And then you make the pilot and then it's like, are they going to renew it? Are they going, people going to watch it?

• 1:16:36Speaker 01

  Yeah. I mean, the, the pilot process was the most rewarding part because, because of that fear.

• 1:16:46Guy Raz?

  Yeah.

• 1:16:46Speaker 01

  It was like, when we finally got the opportunity to make it, like, this is our one chance to do it the way we want to do it. We have to set the tone and like, let's make the best pilot we can. And, you know, they picked that up in days. They picked it up really quickly once we finished it, once we edited it and we felt like really accomplished. And then after that, it was like, okay, now we just have to write a good season. And that was, you know, its own set of trials and figuring out what our voice would be, how it would be different from anything else on TV.

• 1:17:22Guy Raz?

  That show, of course, went through five seasons and finished the final season at the end of 2021. It was a critically acclaimed show, but which is not what I want to ask about. I want to ask about the process of making it week after week, year after year. It's got to be, I mean, I can't imagine how hard it is just to write a script that is, because you want to make something that people are going to love. And just every word, every scene, every moment, just to do that, to make it good, has got to be so hard.

• 1:17:57Speaker 01

  It is, but it comes in the curation of people. It's such a collaborative medium, which is what I love about television. And so in that way, like, that's what made it, to me, sustainable and still fun over the course of five years. It was still exhausting. And one of the things that we realized in the middle of the third season, like HBO, they supported us so much, they were just like, yeah, let's do it. You're renewed. And that meant like, we'd finish the season and go right back in without many breaks. And what was essential for our show is for me and the writers to live lives, because that was the material that went into the show.

• 1:18:33Guy Raz?

  Yeah.

• 1:18:34Speaker 01

  And the advantage of being on a cable network is not being beholden to a specific release schedule, you know, and being able to say, hey, we want to take some time off. And that time off also allowed some existing writers to explore other projects, which means that we brought in some new writers, and that meant new voices.

• 1:18:58Guy Raz?

  I mean, you were really creating a business all the way back when you were making, you know, the Dorm Diaries videos in college, not thinking, presumably not even knowing that or thinking about it, but every step of the way, like, you were building out what would become a business. So you've got a media company. But when did you first start? Because a lot of artists, you know, they make art, right? A lot of people in the creative space make their art and don't think about the business side, where it's really important, especially if you want to retain control over your process and your work. When did you start to think to yourself, I, this is a business too. I'm not just making, you know, art and content?

• 1:19:37Speaker 01

  I have to say with the F word. The F word was the first time that I One named my production company.

• 1:19:46Guy Raz?

  Yeah.

• 1:19:47Speaker 01

  You know, I was like, oh, I'm making, and I didn't call it Issa Rae Productions, because I was like, I'm just creating internet content. So I called it Issa Rae Presentations.

• 1:19:56Guy Raz?

  Mm hmm.

• 1:19:57Speaker 01

  And I was just like, OK, I'm, I'm doing something. I'm making a product. I am definitely building something from scratch. I'm marketing it. I'm creating it. Uh, I'm, I'm, uh, funding it in, in many ways. And this is, this is a product and I have to sell it. I have to sell it to people and make sure that I have a schedule and I'm abiding by a certain schedule. Like, this is my, this is my business and I want people to consume this particular product. So I have to have a structure around it. I say anyone creating for the internet is an entrepreneur.

• 1:20:32Guy Raz?

  Yes.

• 1:20:33Speaker 01

  Because you're just, you, you have to be by nature. Like, it's, it's not enough to just create. And so to make it official for me, um, was essential for me to continue to do it.

• 1:20:43Guy Raz?

  And then Color Creative was initially, I guess, a, as you described, like initially was designed to identify talent and then develop scripts and, and sort of, that was originally kind of a, a production company, right?

• 1:20:58Speaker 01

  Yeah, it was like a pipeline initially. It was meant to be a pipeline to bring in creators of color into the industry, using the model that I was able to, to do with Awkward Black Girl and in terms of creating a product, getting an audience, audience around it and getting the attention of executives to be like, hey, you know, you don't have these people in your writers' rooms, but, and you're saying that this content doesn't have an audience, but look, we're proving you wrong. And then, you know, some of the writers that came, all of the writers that came out of that have ended up in television in some way, but we, Denise Davis and I, who I co-founded it with, um, found ourselves really helping.

• 1:21:42Speaker 01

  Helping them to find their next projects, whether it's recommending them to Writers Room or initiatives or to write on certain films. And we also wanted to formalize that process. We were sending, we were finding them representation. And in some cases, they would come back to us and be like, the representation you found, thank you. It's been great, but not really because they don't really know what to do with me. So we decided to kind of formalize that and make it a management company.

• 1:22:10Guy Raz?

  All right, so you have Hooray Media today. You formally founded in 2020, but you had already had Color Creative. And now that's sort of under this kind of umbrella media company. You've got a radio division, R A E D I O, which I love. And then a TV and film division. So tell me a little bit about the vision. I mean, you had this incredibly successful show with HBO, and you've got a new show on HBO Max. And a big deal that you signed with Warner Media to produce more content, more films for HBO, HBO Max, Warner Brothers, et cetera.

• 1:22:50Guy Raz?

  You've got 25 plus employees, maybe more at this point. What do you, where is it going? What's it going to be in a year, five years, 10 years from now?

• 1:23:02Speaker 01

  Yeah, I mean, I want an ecosystem right now with the new show on HBO Max rap shit. That is sort of the prime example of what we're able to do. So on the writing team, you know, we have a color creative client who's showrunning it. And as we shot it, we had color creative directors, you know, come on and help direct some of the episodes. And just all parts of the company touch it. Radio is also doing the soundtrack. And we just want to be self-sustaining. And we want to compete with the best media companies out there. Down the line, I want to have a studio in South LA.

• 1:23:45Speaker 01

  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.

• 1:24:04Guy Raz?

  You know, I interviewed Nick Kroll for another show I do recently. And I was asking him about performing in front of his parents because a lot of his work is, you know, adult oriented humor.

• 1:24:18Speaker 01

  Yeah.

• 1:24:19Guy Raz?

  And, you know, on your shows, like, you're talking about sex and your sex life and things like that. And I, I mean, is it ever, I don't know, is it ever awkward to like, watch it or like, know that your parents watch it too?

• 1:24:34Speaker 01

  Oh, my God. When I tell you this show, we just had a premiere for Rap Shit and I was sitting next to my mom. Instant regret. Like, I was, I don't know who did the seating, but my mom is very, you know, we were growing up, I couldn't watch PG 13 movies till I was 13, rated R movies till I was 17. Like parental controls were like, you know, all around the house. And so the idea that I'm making the content that younger me wouldn't have watched, she shielded me from, she just can't handle. And there was this big sex scene at the end of the second episode during the premiere. And we're sitting in this theater.

• 1:25:16Speaker 01

  And what sucks is like, I watched her watch the first episode and like, be into it, laughing. And I felt her energy change when there was like, kind of an explicit scene. And I was like, oh, I'm feeling, I'm feeling the tension. And she was still trying to roll with it. By the time we got to that ending sex scene, I like fake covered her eyes. And she turned to me and she was like, you should have done that a long time ago. And I was like, geez. And even afterwards, she was like, she's, it's just not for her. And I realized, you know what? I'm never inviting her to a premiere again. Because, you know, I'm not really making content for her. When she can get behind it, she can get behind it. But it's, in short, it's extremely awkward and it does kind of suck, but.

• 1:26:03Speaker 01

  It's her fault. She made me.

• 1:26:05Guy Raz?

  And I guess your dad is happy even though you haven't become a doctor.

• 1:26:11Speaker 01

  Yes, my dad is satisfied. He's experiencing the fruits of my and his labor. So he has no complaints.

• 1:26:21Guy Raz?

  I mean, you have had an amazing career and it was hard won because it didn't happen overnight. And a lot of people probably, when they first heard about you, they're like, oh, here's this overnight success story. But in actual fact, like, it was an overnight success story that took 20, 15 years.

• 1:26:37Speaker 01

  Yeah. I don't fault people for not knowing. In some ways, you know, I'm just happy they're here. Like, it has been a journey. It has been a long time. Like, even you, again, saying like, the the year difference between Awkward Black Girl and that opportunity with Shonda Land. Sometimes I need that perspective. Sometimes I forget. I've been going at it a long time. But it also feels like I'm just getting started and that is what I choose to focus on, like, the potential. In some ways, now I feel like I'm running out of time and that's a different feeling.

• 1:27:12Guy Raz?

  Wow, you're in your 30s. You threw your whole career out of you.

• 1:27:16Speaker 01

  I know, but I'm a woman in Hollywood. You know, there's just different, there's different standards.

• 1:27:21Guy Raz?

  There's a different timeline.

• 1:27:22Speaker 01

  My god, yes, there is. And then you think about, you know, the personal life of, like, what kids will do to that and what, you know, expanding and starting a family looks like.

• 1:27:31Guy Raz?

  Right, because you got married last year. Congratulations.

• 1:27:34Speaker 01

  I did. So there's just, there's just other facets that I have to consider that I was not thinking about in my 20s when I got started.

• 1:27:42Guy Raz?

  When you think about this, your story and this trajectory and all that it took to get to where you are, how much of it do you attribute to just the grind and the hard work you put in? And how much do you think has to do with luck?

• 1:27:54Speaker 01

  Oh, man. I mean, I know I worked hard as hell. I still do. I work hard as hell. But I can't deny that things had to align for this to work out. Like, there's just so many... I say it's 70% work, 30% luck in some ways. And that scares me sometimes because I'm like, oh, my God, all these things had to go right for me to be here. And I'm so happy I'm here. But like, I can identify those fork in the road moments where if I had just made a different decision, maybe I wouldn't be talking to you. And I'm very, very fascinated by that. But I also try not to spend too much time thinking about those moments.

• 1:28:35Guy Raz?

  That's Issa Rae, writer, producer, actress, and founder of Who Rae Media. By the way, if you do some internet sleuthing, you can find a few of Issa's early YouTube videos, including this freestyle rap she made with friends her senior year of college.

• 1:28:53Speaker 01

  Nani pop with a friend, nani pop with your man. You can keep and do the nani pop on a handstand. If you want to get down, do the nani pop now. I'mma do the nani pop and get down, do the nani pop.

• 1:29:06Guy Raz?

  Hey, thanks so much for listening to the show this week. If you enjoyed it, please do spread the word. Tell someone about How I Built This or post about it on social media. And thanks. If you want to contact the team, our email address is [email protected]. If you want to follow us on Twitter, our account is at How I Built This and mine is at Guy Raz. On Instagram, we're at How I Built This and I'm at Guy dot Raz. This episode was produced by Liz Metzger with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Patrick Murray and James Willetts. Our production staff also includes J.C. Howard,

• 1:29:49Guy Raz?

  Kerry Thompson, Alex Chung, Josh Lash, Sam Paulson, Katherine Seifer, Elaine Coats, John Isabella, Chris Messini, and Carla Estevez. I'm Guy Raz, and you've been listening to How I Built This.