How I Built This with Guy Raz - HOORAE: Issa Rae

Episode Date: September 26, 2022

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 launching September 20thSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Airbnb.ca.ca. slash host. Hey, it's Guy here with a very exciting announcement. I have a brand new podcast. It's called The Great Creators and the launches on September 20th. 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. 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. 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. How's it going? Yeah, how's it going? How's it going? How's it? How's it?

And it's just like, oh, yeah, just a different direction. You know, I'm 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 different. devastating, and I thought it was over for me.

I thought nobody's going to want to work with the failure who couldn't make a show with Shonda Arimes, who couldn't, like, make the layup. Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz, and on the show today, how Issa Ray refused to wait for permission to make TV and made her own, and how she turned her YouTube content into a brand to his hit TV shows and eventually a Hollywood production company. 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, 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 Calajoni's sandbox was throwing any fruit he could find into his batch of homemade beer.

He'd invite friends over and let him 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 Ray, 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 Ray was writing scripts. She even submitted some unsolicited scripts to sitcom producers in LA in the 1990s. 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 a 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. 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 Farrell and Shonda Rimes. 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. 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 L.A. was born in L.A. 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 U.S. 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. Yeah, I remember him, you know, he opened this practice in Englewood. And I remember visiting it. He had maybe like a launch party.

That's not what you call it. But it was something. The medical practice lunch party. Yeah, it was 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 from the ground up.

This is, that stood out to me as, you know, something that was distinctly his. special. He's a pediatric specialist, right? Is that right? Yeah, he's like a family practitioner, but yes, he's a pediatrician. Which is always really helpful to have in the family. Oh, 100%. But also, he's the most dismissive of any ailments we may have, because he's just like, he's seen it all. He's seen it all. But it is really helpful. Like, even just the other day, I was like, ah, I have this thing, but if it doesn't go out 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. That's actually, when you say dismissive, actually, that's a

probably surprisingly comforting. Yes. Oh, yes. A hundred percent. Just go to work. Exactly that. If he's concerned, then I'm concerned. All right. So the whole family moves out to L.A. and you start middle school there, a magnet school that was a sort of a science-focused, magnet school. Were you a science-focused kid? 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 going to be me then. Of course I'm going to make him proud. I want to be a doctor too, just like him.

And of course, even seeing his practice, seeing his name. Yeah. On the clinic was special, going to school, going to middle school and being like, oh, your last name is mispronounced. Diop, jope. Jope. your, 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 stoke my interest in science and medicine. Yeah. And I guess I should mention Ray is your middle name. Your last name. Ray is my middle name. Yes. Tell me about sort of home life, like cultural life. Was Senegalese culture a big part of your upbringing, the food you ate or?

celebrations or even communities that your family spent time with? Yeah, definitely. 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 L.A., 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 that. They're in.

Yeah, they're in. So we had a lot of studying of Lee's relatives staying with us over the years. How did you become interested in acting? Did that start in high school? 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. And did you, I mean, when you were on stage, what was it about? I mean, because it's scary to get on stage as a kid and as an adult, right? Was it, did you feel comfortable in front of people performing? I did. I didn't feel that fear as a kid.

Like, I definitely feel that fear as an adult more than anything. Yeah, because we're more, we're more, for example. of being judged. 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, 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. Yeah. What, did you do any? plays in high school? 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. And when you were in high school, did you already start to think about maybe that could be a profession? Yeah, when I was in middle school and I moved to L.A., I was already writing. I was writing a lot. What were you writing? 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 half an hour. But I was still sneaking. and that means that I was catching up on weekends. And I just wanted, as soon as I found out we were moving to L.A., I was like, oh, my gosh. L.A. 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 Moisha, a taping of Moesha, and to sit in that live studio audience changed my life. And I got, I want to teleplay. I wanted to teleplay of that episode.

You want, right, this is, Moisha was on UPN, I think, in the 90s. Yeah. And you went to go see a live taping of it. Yep. And they would just give away like the paper script every up, like, somebody in the studio audience. Yes. And I got one and in my hands was the blueprint of how to write as it come.

And I studied that front and back. Yeah. I mean, that must have been amazing. This is pre-internet. Like it was the ability. to just get that kind of information wasn't it wasn't available. Absolutely not. 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. This is how it's done right in front of me and I got to see it play out and I remember the movements and the episode's going to air when it airs and then I'll be able to like follow along and it really was like I started writing right away. So you would look at this so you could see the script because I know you've written a 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 um and then you had this template to kind of plug in your story using this as you write the blueprint right and what were you tell me like what you started to write what are the stories that you were starting to write well I did one original So stupid

One original sitcom called Ronnie about a middle school boy Living in L.A. Trying to avoid gang violence Because I had seen South Central A short-lived sitcom That one of my heroes

Gina Prince Bidwood wrote for She also did Love in Basketball, I think. 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 got to be commercial. Like, you know, I can't just go out the gate with an original. You know, 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. And I think your episode was called Tong Ring. Is that right?

Wow. Yes. Yes, it was. 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. And it was radical. Definitely very radical in the 90s. Yes, it was.

And you sent that to CBS, right? Yeah. And my grandmother taught me, because 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 the cover letter as well. Oh, wow. This is like before people, people had legal Zoom, 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? Oh, yeah, for sure. I got a 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 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. Who would you allow to read your stuff when you were in high school? I was always, I was definitely protective about letting people read my stuff. Because it's really personal. It is. And you don't want, and even now I feel that way. Like, 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 mess with it. I love it. Like for someone else to taint that, I was very aware of that and really insecure about that. And I remember I did 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, 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'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. So I know that after you finished high school, you went to Stanford for college. And how did you feel as a student at Stanford at that time?

Because I've seen you quoted kind of talking about it, how it just wasn't diverse, right? I mean, you get to this place. It's 2003. Of course, it's this world-class school with all these resources and computer labs and great professors and all this stuff. but it sounds like maybe at least initially you felt isolated there. Well, the opposite. I think I isolated myself in a bubble because I was used to and 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 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. Right. 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 hopper 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. I just made it less intimidating for me to feel like I could do it too. But it sounds like from what I've read, like that community of friends that you have had, that was kind of the beginning of grinding through ideas that would eventually, you'd 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 performance of school days. Like, you were, you put on a stage adaptation of, of that Spike Lee film. Yeah, that was my first production and the community behind that, like, some of the people, even just in that play that helped me produce it, that we're in it, are still heavily part of my community right now. But yeah, that started the run of four years of putting on productions, like terrible productions, but still productions. But still, yeah. Well, I mean, there's no way that you get to a place where with zero experience directing and producing and you're going to do it well. And that's the place

to do it, right? When you're 18, 19 years old, to try it out. And that's how you learn how to do it presumably. 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. Because their theater program is so elite, you know, and their film program and all that, you know, that people go there who are extremely. talented and killing 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 increase my confidence.

As you can imagine, I hope this isn't mortifying to hear. I've watched a lot of your videos from college. Oh my God. What? You know, they're available to see and they're fun. I mean, they're fun. You have to, as you say, like, I'm sure part. Part of you 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.

Yeah, because it just 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. And would you, would you like, is this pre- iPhones, too? Would you just film it on like a camcorder? 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 the firewall cable to put it on my laptop oh yeah the firewire firewire thank you Jesus it's so long ago right because it was like the I remember there's like the fastest way to get something from a camcorder to your Mac right yeah and it was just it was so arduous

but at the time you were just like I'm gonna make yeah I'm gonna make magic nobody else is doing this um and you I mean you were doing other things like like you started uh Machi Marie series called Dorm Diaries. I guess it was like kind of maybe partially inspired or similar like the real world on MTV. Oh yeah.

I guess that must have been where I got it from. So that the office wasn't I want to know. The office wasn't out by that time. Yeah, I think maybe the British version was out. Yeah. So I think it was definitely a combination

of the real world and the mockumentary style of the British office. You worked on this with your friend, Tracy Oliver. It was a college frattened who would go on to become well-known in her own right is a writer and a producer um 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 yeah so i wrote the script and just like cast my friends um one of the friends that i ultimately cast was tracy yeah then i 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. 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. Yeah, it started to spread to other college campuses that had, you know,

either black dorms or BSUs, were just like, this was, this is my college experience. And they felt, they felt seen. You said in an interview several years ago that that experience was a light bulb. It was your, you called it your epiphany moment. Why? 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. Yeah.

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, recorded myself, edited 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. 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. New York and I guess while you, why you sort of soon after you got there, 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. 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. It's a really tough time in life because you're like 22. It's, you broke as hell. Yeah. And it's really hard to get anybody to take you seriously in your New York and it's expensive. And it's

stressful. Do you remember feeling anxious about just life? 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. 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 L-Sat. And then ultimately the G-MAC just to be able to.

get a master's like he wanted me to do so badly. 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. 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 what she had not done before. He gave me all of his original taste. 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 I had my camera set up in my bedroom, it was on a tripod. And it was like pointed towards the bed. And somebody was like, they probably thought that was porn. Like they were stealing porn tapes. And I was like, damn, they're going to be so disappointed when it's just like a Jamaican movie.

So I felt really, really bad. for him and then of course hated that all of my everything was stolen. It's sexual violation and of course my roommate's stuff and you know we just felt so helpless. I read that you also describe yourself as an introvert

and 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. Exactly.

Yeah. To put yourself out there, which is like what everyone tells you. You just got to put yourself out there. Do you know how hard that is? So hard. 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. Would you write things down in a diary? All the time. The diary, the journal, because that's what makes sure people say. The journal was like my therapy. But people could also tell. You know, 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 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. I mean, what's amazing, and we're going to get to this, is anything 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 extroverts 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. But 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. I think once I realized 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 realize people. I realize 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. What did you, what did it, what did it mean for you to feel awkward and black? How did it, how did that, like, what were things that that made you feel that way? 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 fact that those two didn't necessarily intersect, often even publicly in images that I'd seen in media. And that was something that I wanted to explore. 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? Well, that's a thing. Like, a lot of times, 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 idea, I mean, which is a risk. I mean, putting yourself out there is kind of scary.

I just didn't, well, I wanted to know that I wasn't alone. And that was the first iteration of that idea after I wrote it down was like, ooh, I'm going to 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 it's a conversation starter. Or even if you don't start the conversation, it's a way to feel like, oh, 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. 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. What prompted you to leave New York and move back to L.A.?

My friends, and that was another revelation, visiting L.A. 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 L.A.? in New York, yeah. 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 L.A., everybody you know is here. You can save money. And I was just like, yeah, what 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, I had nothing's keeping me here.

I might as well go home and see what I can do. When we come back in just a moment, how Isa builds a giant fan base with awkward black girl, a show that gets boosted by a Kickstarter campaign and a phone call from Farrell. Stay with us. I'm Guy Raz, and you're listening to How I Built This. 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,

Isaree decides to move back to L.A. Where at first, she moves in with her mom. That was hard. Yeah. Ooh, that was hard. Because she just treated me like I had never left. Right. And you're like in your 20s.

You want to be independent. Yeah, I want to start your... Yep. Yeah. And she's waking me up in the middle of the night because I left dishes in the sink. And it's just like... First of all, yes, it's disrespectful for all 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, and you're paying your own bills. So it was really, really humbling and frustrating. Meantime, you were still experimenting with video.

Like, you were still, like, with all the 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, 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? Yeah, when I, I will credit New York for giving me that hustle mentality. I left New York and came to L.A., and L.A. felt so slow to me. Like, L.A. 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. And, like, they're just, they're ready. And so there was part of me that didn't want to be the flaky L.A. person. So I realize, 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. And so my brother had this music group. I asked if I can do his music video. And he was like, yeah, if you're going to 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. So, yeah, so you would work all day. And then you would spend your night's writing scripts for the F-word. Yeah, I wrote outlines to their credit.

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. All night. All night. And make sure that it come out at the same time every Monday morning, F-word Mondays. And you would film it and write it and edit.

and edit it and do everything yourself in your computer. Yep. It's a lot of work. It was, but it was so fulfilling because it was like mine. It was their talent, but my work. It was such a good boot camp for me. You know, I really, I really cherish that time. I mean, not to bring my story into it,

but 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 it was bad. But I had to write that stuff in order to be able to eventually make stuff that was good. And I mean, you did this for seven seasons. You made seven seasons of the show. 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 when you're like, okay, this is bad. This is not great. But you're still encouraged by the fact that you're doing it and you feel good about doing it. I'm not sitting back. And it's like, I know that I'm only going to continue to get better. And there's something satisfying. And then at one point, you sit back and you're like, I think this is good. Yeah.

Yeah. 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. 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 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 inner most thoughts?

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 going to 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 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? 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 going to 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. Which is what you did. In 2011, you put out your first episode of Awkward Black Girl. And I mean, by that point, I mean, you knew how to do it, right?

I mean, 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 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 character in the next car. You know, that first scene, it's like, did you, are you ever a situation where somebody driving the car?

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 a first one and and so you knew how to just create something even you know 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 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 yeah 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 was like, okay, I'm still going to 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 that came down to even casting myself because I wanted someone else to be to play Awkra Black Girl. The lead in Dorm Diaries is who I wanted to play awkward black girl. She was in D.C. 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. I was like, 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, getting the idea out there was more important to me than being scared of being judged on the internet. 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 J. And you were, it was the easiest solution was just to have you do it. It was. And I knew what the character was. That was it.

Like, I was like problem solved. Yeah. I mean, in those first certainly, like, and for people who haven't seen it, it's basically follows his character, Jay, who's a telemarketer and is, you know, awkward, has these awkward encounters in her life. And, and also there, you hear her inner dialogue or monologue, I should say, and, and that 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. I mean, 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? 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.

Captured. Okay, the mic from the camera. Okay. 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 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.

You presumably, I mean, you were finding this yourself, and 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. 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 and my friend at the time was telling me about Kickstarter and I dismissed it I was like, I'm not raising money online And that feels so desperate. And then our cinematographer, Shea, he brought it up and was like, I heard it, have you heard of this thing called Kickstarter? And that's when I took a series. 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 didn't give an ultimatum, but. before this episode that we knew would make an impression. We basically asked our audience, we told him, 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. Yeah. And by the way, at that point, those first sort of three, four episodes, how many people were you getting? Because this was still new. how many viewers were you getting per episode? I actually don't remember. I know that was above, it had to be between 30,000 and 50,000, maybe 100,000. Wow.

How are you getting so many viewers? That's amazing. We released it the first Thursday of every month. And that was like a release schedule I just came up with. When I released the first episode, I just, I was like, okay, I did it. got ahead of the idea, 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. 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 focusing on any of that? 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 spread the word. Wow. And yeah, you can amplify that. that, you can do things to amplify that, but if something is good to people, they're going to talk about it. And that's going to be the main source of your eyeballs, your support.

Yeah. I mean, you raised $50,000 in this Kickstarter campaign, and you started to get quite a bit of attention, including from Farrell Williams, who I guess reached out to you because he was interested in maybe collaborating. I mean, that must have been kind of mind-blowing to get an email from, or whatever, like a message from Farrell Williams saying, hey, can we talk? It was extremely mind-going. We had already gotten, like, you know, some great celebrity support. Gabrielle Jung, and 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 Farrell was the first person to, like, call me and be like, I want to, like, I want in. I want to figure this out. And he had this, you know, when Google did the 100 channels and gave, um, various creators, whether they were YouTube stars, established musicians, they gave channels, and they put funding behind those channels, trying to make the new TV on the internet. He had one of those channels and was able to fund our second season

via his I Am Other company. So what did that mean for the season two? Because you can see it. 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. 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, 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, okay, I'm being compensated properly for my work. Did you feel after that show started to get attention and you're collaborating with Farrell Williams that, okay, did it like sort of lessen your anxiety? Did you start to feel like, okay, 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? 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, Ferrell's messing with 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. Yeah.

This is all that's in me. And so even with awkward black girl being successful, I was like, 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, another work.

And it took a realization and even other people to just kind of make me focus. Like, there's something that you did, and you have to focus on that, and you have to embrace that. It's you. 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. 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. The most exciting thing that happened to me was being able to, Pitched for Shandana Rhymes to me. Huge inspiration.

Had gray's and scandal at the time. It's killing it just as a black woman showrunner and her. 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 going to 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, you know, I got the grand announcement that I was going to be doing, developing Shonda Rhyme's first comedy. And that was a big deal to me. I mean, this is like 2012. You launched your web show in 2011. I mean, that's amazing. Like, you were pitching Shonda Rimes. Like, how crazy was that to sit in a room with it?

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 Ryans. It's Shonda Ryms, and she's intimidating as hell. And she is, like, one of the most successful showrunners in history.

So you're there, like, a year after you launch us, maybe less than a year after you launch this thing, talking to her in a room, like, what do you remember about that? 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. 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 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, yes.

So I still have that picture. You still have it? Oh, wow. 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 going to let Shonda rhymes down. And this was a show called I Hate L.A. dudes.

And it was sold. the ABC one was basically about the concept. Yep. And so you start to work on a pilot. I started to work on a pilot, and that was my first real television pilot process. And how did it go? I mean, how are you,

was it just you in a room, or were you working with Tracy, or were you working with, yeah, how are you writing it? This was just me. This was me. By that time Tracy was writing 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. There are a lot of cooks in that kitchen. There are so many cooks. And they don't all agree.

To someone who just wants to please, it can be maddening. And for me, 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. And I just, I kind of just didn't know what I was doing. And I credit. at, you know, Shauna Land, 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. I mean, the show was called I Hate LA Dudes. It was about about a woman who was dating horrible, awful image. obsessed men in Hollywood. And I guess 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, 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.

Yeah. Yeah. And what's crazy is I 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. I didn't really know how to make a good network show yet. I was still in the internet mode. Tell me when they ultimately decided not to back up, make a pilot for that show. Was that devastating? Did you feel like, okay, well, I'll just move on and go to the next thing? Like, did you feel like it was a, yeah, I mean, it was like a gut punch?

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. How's it going? Yeah, how's it going? What?

It must be great. Kill it. And then it's just like, oh, yeah, just a different direction. You know, I'm 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 show work every day? No, do I ask you how your project's doing?

But no, like, it was just, it was really devastating. And I thought it was over for me. I thought nobody's going to work with the failure who couldn't make a show with Shonda. rhymes. It couldn't like make the layup. Were you writing that about that in your diary? Probably. I haven't. I have to check. I have to check. But I definitely remember I don't cry often, but I want to say I cried after that. It was either that or the next HBO failure.

Because you do, I mean, you do eventually pitch a show to 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, from what I understand, you started 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 in his shows. So how did that collaboration happen? How did How did that start? So after I sold my page to HBO, they bought this nonprofit idea.

Then my managers were like, you know, you're going to need a showrunner. You're going to 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.

just really intent on bringing out my voice. And so then, you know, he was attacked to the project and helped me to start to write the pilot. 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. So the way it works is, you know, obviously the deals take a long time.

And so to put employees. 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 the show,

what the pilot 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 that I'll never leave my mind but 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 nightly show opportunity and so that was like his dream job. And by that time, he was also helping with Blackish. I was like, damn, you got all this happening.

And we're still, I'm still working on this damn show. And I'm going to lose you. And I did. And when I lost him, I thought, that's it. That's it. Again, here I go again. They're not, 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. They were not happy with the pilot. They were not ready to green light it. They were not ready to green light what was then known as nonprofit with a pH. No. And meanwhile, I mean, you were also kind of on the line because I think around this time you had actually launched something completely different, a whole separate venture, which would be the beginnings of a management company, your own business. Yes. It was called Color Creative and 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 going to 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. So you had nothing left?

I had nothing left. But I was like counting on this coming through. This green light, yes. I was like, okay, well, there's going to 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 going to do. I 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. And I've, yeah, I've made a mistake. Like, I put all my eggs in this basket in these, well, two baskets.

So you were simultaneously financing pilots that you put all your money in and counting on this insecure deal to go through and still. And so, yeah, then they were like, well, well, we still want to. going 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. What was your version of like a Laverne and Shirley look like? They're talking about the character of Molly. 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 happens if I make it closer 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. It's amazing because, I mean, television 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 to people going to watch it? Yeah. I mean, the pilot process was the most rewarding part because because of that fear, 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. That show, of course, went through five seasons and finished the final season in, end of 2021. It was a critically acclaimed show, 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. 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 a material that went into the show. Yeah. 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. brought in some new writers and that meant new voices. 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. 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, this is a business too. I'm not just making art and content.

I have to say with the F word, the F word was the first time that I, one, named my production company. Yeah. You know, I was like, oh, I am making. And I didn't call it Eastray Productions because I was like, I'm just, creating internet content. So I called it Issa Rae Presentations. And I was just like, okay, I'm doing something. I'm making a product. I am definitely building something from scratch. I'm marketing it. I'm creating it. I'm funding it 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 yes because you're just you have to be by nature like it's not enough to just create and so to make it official for me was essential for me to continue to do it and then color creative was initially I guess as you described Like initially, it was designed to identify talent and then develop scripts. And sort of, that was originally kind of a production company, right? 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 do with awkward black girl in terms of creating a product, getting an 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, found ourselves really helping, helping them to find their next projects, whether it's recommending them to write a room or initiatives

or to write on certain films. And we also wanted to formalize that process. 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. All right.

So you have Hooray Media today. You've formally found 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 WarnerMedia to produce more content, more films for HBO, HBO Max, Warner Brothers, etc. You've got 25 plus employees, maybe more at this point.

Where is it going? What's it going to be in a year, five years, ten years from now? 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 show running 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 L.A. 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. 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. And, you know, on your shows, like, you're talking about sex in your sex life and things like that. And I, is it ever, I don't know, is it ever awkward to, like, watch it or, like, know that your parents watch it, too? 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 until I was 13, rated-d-ar movies until 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, when it watched us, 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. And what sucks is like, I watched her watch the first episode and like be into it laughing.

And then I felt her energy change when there was like kind of an explicit scene. And I was like, oh, 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's like, it's just not for her. And I realized, you know what?

I've never invited 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 in short, it's extremely awkward. And it does kind of suck. But it's her fault. She made me. And I guess your dad is happy even though you haven't become a doctor.

Yes, my dad is satisfied. He's experiencing the fruits of my and his labor. So he has no complaints. I mean, you have had an amazing career and it was hard won because it didn't happen overnight. Right. 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 15 years. 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 year difference between awkward black girl and that opportunity with Shondaland. Sometimes I need that perspective. Sometimes I forget. I've been going out of 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. Like I'm running out of time and that's a different feeling.

Wow. You're in your 30s. Your whole career out of you. I know, but I'm a woman in Hollywood. You know, there's just different. There's different standards. There's a different timeline. 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 a family looks like. Right. Because you got married last year. Congratulations. I did. I did. So there's just other facets that I have to consider that I was not thinking.

I was not thinking about in my 20s when I got started. When you think about 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? 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 tried not to spend too much time thinking about those moments. That's Issa Ray, writer, producer, actress, and founder of Hooray 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. Nottie pop with your man.

You can keep and do the nani pop on a handstand that you want to get down. Do the nani pop now. I'm going to do the nani pop and get down. 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 H-I-B-T at ID.wondry.com.

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.ros. This episode was produced by Liz Metzger with music composed by Ramtin Arableu. It was edited by Neva Grant. Our audio engineers were Patrick Murray and James Willits. Our production staff also includes J.C. Howard, Carrie Thompson, Alex Chung, Josh Lash, Sam Paulson, Catherine Seifer, Elaine Coates, John Isabella, Chris Messini, and Carla Estevez. I'm Guy Raz, and you've been listening to How I Built This.