HOORAE: Issa Rae

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 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 the great creators. It's available wherever you find your podcasts, and please do subscribe so you won't miss any of the episodes. In our first episode Is with Steven 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. Oh.

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 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? Ah shut it. And then it's just like oh Yeah.

Yeah, uh just different direction. You know, I'm just working on a lot of things, so You know. Um 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 do it? But no, like it was just it was it was really devastating and I 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 Shawn O'Rhimes, 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 Rae refused to wait for permission to make TV. Made her own. And how she turned her YouTube content into a brand Two 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 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.

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 E Saree? 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.

In college, she'd recruit friends to act out her ideas and video them with a campcorder 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 twenty two, 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 Pharrell and Shonda Rimes. That low-budget web series would lead to a deal with HBO, an 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. Isera 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. Yeah, I remember him

You know, you're up in this practice in Englewood. And I remember visiting it. He had maybe like a A launch party. That's not what you call it. But it was something the medical practice lunch party. 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, it was in this neighborhood that was he was servicing predominantly black and brown Patience and it was just like, Oh, my dad built something. Yeah. From the ground up. This is that stood out to me, um as, you know, something that was distinctly his and 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, a hundred percent. 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 He's seen it all. But it's it is really helpful. Like t 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 he 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 like oh yeah something deep. A hundred percent. Just g go go to work. Exactly that. If if he's concerned then I'm concerned. Um, all right. So the f whole family moves out to LA and you start middle school there, um a magnet school. That was a sort of a science. Focus, Magnus School. Were you a science focused kid?

No, but my dad Again, you know, he was a doctor and so Uh 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'm gonna 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 Mispronounce. Dia. Jope. Jope. But you're Is your dad.

Thank Is your dad my doctor? And that was special to me, so For me that was The vanity of it might have kinda stuck my interest in science and medicine.

Yeah, and I guess I should mention Ray is your middle name, your last name. Um Tell me about um sort of home life, like the 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 s your family spent time with? Yeah, definitely. It was it was I would say Perfectly. balance 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. Yeah, they're in. So a lot we had a lot of Senegalese relatives staying with us over over the years.

Wha w 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 kinda cool and when I'm on stage

People are laughing. In the 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 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 feel that fear as an adult. more because we're more we're more afraid of being judged. Absolutely. And kids you're just like oh our 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. 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 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 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 LA, I was already writing. I was writing a lot. Wh where w 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 T V on weeknights and then it became a half an hour, but I was still Sneaking and that means that I was catching up on weekends. Uh, and I just wanted and w as soon as I found out we were moving to LA, I was like, Oh my gosh. LA is where

Hollywood is and where T V is Maybe this is my chance to be able to write. And Uh my childhood friend had tickets to Moesha, a taping of Moesha and to sit in that live studio audience.

changed my life and I got um I want a teleplay. I want to teleplay of that episode. You want right, you y this is Moisha was on UPN, I think, in the nineties. Yeah. And and you went to go see a live taping of it. Yeah. they would just give away like the the the paper script every up like to the somebody somebody in the studio audience. Yes. And I got one and

in my hands was the blueprint of how to To write us to come. And I studied that. Front and back. Yeah, I mean that must have been amazing. This is pre internet. Like it was the the ability to just get that kind of information wasn't

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 got to I remember the movements and the episode's gonna air when it air 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,'cause I I know you've written a a you've talked a little bit about this in your book that came out in twenty fifteen about how like nineties television really just I mean it was it was the right time and place'cause 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 This as you write the blueprint, right? And what were you

Tell me like what you started to write. What is what were the stories that you were starting to write? Well, I did one original stupid One original sitcom um called Ronnie about a middle school boy living in LA trying to avoid gang violence'cause I had seen South Central. A short lived sitcom that one of my heroes, Gina Prince Bidewood, wrote wrote for She also did love and 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 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. And I wrote an episode of that. And I think your episode is called Tongue ring, is that right?

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. And it was radical. Definitely very radical in the nineties. Yes, it was. Um and did you and you sent that to CBS, right? Yeah, and then 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 d diligence and then sang it out with the cover letter as well. Oh wow. This is like before people we people had legal zoom, right? Like now people That's so smart. So you email it to yourself. Then you could prove that it's your IP and then you send it and and did you ever hear back from them? Oh yeah, for sure. I got uh 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 twelve. Eleven twelve. So I I'm not there yet and I kinda just gave up on it. Who would you 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.'Cause it's really personal. It is. And you don't yeah, and even now I feel that way. Like I don't want it I don't want any negative energy. I don't want anybody to tell me it's not good or that it doesn't resonate with them. It's always better when you feel good about it. Like that 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 meet 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, 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. Hm. So I I know I know that that after you finish high school you went um you went to Stanford for college. And how did you feel as a student at Stanford at the time?'Cause I've I've seen you quoted, you know, kind of

uh talking about it uh uh how it it just wasn't diverse, right? I mean you get to this place, it's two thousand three Um, it's of course it's this world class school with all these resources and computer labs and great professors and all this stuff, but Um but But It sounds like maybe at at least initially you felt

Isolated there. I well the opposite. I think I I isolated myself in 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 colour. Yeah. Drama teacher was and so Like even the productions they 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 likely a girl was had started like this, um theater company just to put on her own play and She

put on a hip hopper and cast me Um as one of the leads in That experience was incredible just to watch her pull the resources together to make it happen. And

also seen that she was an amateur in the space. I mean it just made it like less intimidating for me to feel like I could do it too. 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'd have to go through that to get to what you would eventually get to. Like you really started to

You mentioned acting in theater like you mounted a uh performance of school days. Like you were you put on a 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 help me produce it, that were in it.

are still heavily part of my community right now. Um, but yeah, that started the the run of Four years of Putting on protections. Like terrible productions, but still productions. But still, yeah. Well you ha I mean, there's no way that w that you get to a 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? When you're eighteen, nineteen years old.

to try it out and that's how you learn how to do it, presumably. Absolutely, and I and I'm I really credit Stanford for being such a welcoming place to do that. And I think it was so welcoming because No, that wasn't the 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 uh intimidated, but to

Do something like that at a school where that's not the focus. uh made things Increase my confidence. Um As you can imagine, I hope this isn't mortifying to hear, I've watched a lot of your videos from college.

Oh my What the No Um they're available to see, and and they're f I mean, they're fun. You have to as you say, like, I'm sure part of you's sort of embarrassed t to see them, but but like you can also see the beginning of of a performer and and a writer developing Um, and you would do this, like you would start to you and friends would just kind of make videos of songs and

You'd upload it. to the internet. Yeah,'cause it just felt like such a s It felt like such a small community. Uh, 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 you be you know like you're not thinking about the fact that this will live on and then 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.

Um, and would you would you would you like'cause this is pre iPhones too, would you just film it on like a camcorder? Yeah, a cam recorder that was readily available in our school's library. I Constantly check that camera out. Just to record and then Yeah, then use the

The firewall cable. To put it on my laptop. Oh yeah, the fire wire. Fire wire, thank you. Jesus. It's so long ago. Right,'cause 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. Nobody else is doing this. Um and you I mean, you were doing other things like like you started a mock memory series called Dorm Diaries. I guess it was like kind of inspir.

s maybe part partially inspired or similar like like the real world on M T V Oh yeah Uh I guess that that must have been where I got it from. So the the office wasn't I wanna No, the office wasn't out by that time. Yeah, I think maybe the British version was out. Yeah. So I think it was a it was definitely a combination of the real world and the mockumentary style of

The British office. You um worked on this with your friend Tracy Oliver was a was a c college friend who would go on to become Well known in her her in her own right. Yeah. producer. Um and w tell me what you would do. Like you would give scripts to like a

st a bunch of different friends and you would shoot scenes uh around campus or In dorm rooms or just anywhere? Yeah, so I wrote the script. And just

Yeah. Gay like cast my friends. Mm-hmm. Um, one of the friends that I ultimately cast was Tracy. Yeah, then I would just go and film it. take up like thirty 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 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. We're just like this was this is my college experience and They felt They felt seen.

Um you said Several years ago that that experience was a light bulb. It was your you called it your epiphany moment. Um wh why? Because

I had spent all this time trying to Right and Send my work. To

Іде продус, езекутив. contest, whatever, in an attempt So 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, th 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. All right, so you have this project that you do and I know when you when you graduated you went to New York, you got a fellowship um 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 Helping you turn it into uh like a professional show. Yeah, I wrote like the the spec script uh of

What the television show would be and then my brother had A friend who worked at I wanna say VH One at the time and I was begging him like give me a meeting with her, give me a meeting with her. Um so all those I w 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'cause you're like twenty two it's you Broke his hair. Yeah, and it's really hard to get anybody to take you seriously. in in you're New York and it's expensive.

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 want it to do. Mm. 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. I 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 and that was just like damn everybody's killing it. Yeah, 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 Elsa and then ultimately the G Mac just to be able to get a master's like he wanted me to do so badly. I I know that at one point um you you invested a little bit of money in some film and editing equipment and then it was s it was stolen, like your apartment got broken into. Yeah, my apartment got broken into the night before I was supposed to go pig. Um 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 um 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. So I felt Really, really bad. Um

For him and then of course. hated that all of my everything everything was stoned as such a violation. And of course my roommate's death and you know we just felt so helpless. I I read that you also describe yourself as an introvert and I I'm trying to like picture you twenty two, twenty three, 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. Excellent. Yeah. To put yourself out there? Which is like what everyone tells you to do you just gotta 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

Mm. posing 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 pay 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. Um because that's what make 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 insecurities 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 Um, like I was being judged. Hm. 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 hope. I mean, what's amazing and we're gonna get to this is anything anyone listening can kinda 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

uh acknowledge that the world is dominated by extroverts and introverts have to figure their way. how to navigate that world. And But you Do 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 th you would turn those into powers. 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 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, uh Just I'm awkward and black.

And I shared that as a Facebook status. And my friend Tracy was like, Ha ha ha, those are the two worst things anyone can beat. And I just found that hilarious. What did you what did it

What did it mean for you to feel awkward in a black? How did it how did that Um 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, s how many of those things also had to do with My blackness. Two and

That realization just kinda made me laugh. Uh and the the fact that those two didn't necessarily intersect. Um, often even publicly in images that I had 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?

Well that's a 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 a is kind of scary.

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 it's a 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 to 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 what what prompted you to leave New York and move back to LA? My friends and that was another revelation, um, visiting LA I wanna say I I came maybe for a graduation or something and I caught up with Tracy and my my other Asian friend Ashley went to the beach one day.

And they were just like, Girl, why are you still in LA? In New York, yeah. Yeah, you know, I'm out here uh trying to become an agent. Tracy's out here, you know, in the producer's 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 kinda wasting my time. It it's not I I haven't failed if I come back home. And so that was like yeah, I'm I'm I 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 Issa builds a giant fan base with awkward black girl. A show that gets boosted by a Kickstarter campaign. And a phone. From Pharrell.

Stay with us, I'm Guy Raz, and you're listening. 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. Isare decides to move back to LA. Where at first

She moves in with her mom. That was hard. Yeah. Because She just treated me like I had never left. Right. And you you're you're like in your in your twenties, independent. You want to start your

Yeah. And she's waking me up in the middle of the night because I had left dishes in the sink. And it's just like First of all, yes, it's disrespectful on my end to like come home and Leave him asked. But come on. I'm not sixteen anymore. Like what 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 of 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 felt like you started on on a a web show called the F Word. Um, which was a kind of a it was your brother was in it and his friends and And tell me about

just making that. Just a fun side project to to do or did you think Wh what were you thinking about that? Yeah, when I well 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 then like 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 they 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. 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 Yeah. And when I was on that music video set.

They were so funny together. You know, I was just like y'all are Yeah, the talented but you're also funny. And you're funny together. I wanna make like a show around you. So y

Yeah, so you would work all day and then you would spend your nights writing scripts. For the F word. Yeah, I wrote outlines to g to their credit. Like so I give them the story points, where to go, and but I never told them what to say. They just got it and they would improv their way through those story points and I've edited together. And stay up.

You know, editing it and make All night. And make sure it I'd make sure that it come out. At the same time every Monday morning, F word Mondays. And you would film it in

Write it and edit it and Do everything yourself. In your computer. Yep. Still a lot of work. It was, but it was so fulfilling'cause 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. I mean Not to not to bring my story into it, but just reminds me so much of when I started out as a writer twenty five 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 to in order to be able to eventually make stuff that was good and and I mean you did this for seven seasons. You made seven seasons of the show. Yeah, seven seasons over I wanna 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 gonna continue to get better. And there's something satisfying in that I mean at one point You sit back and you're like I I think this is good.

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 It's like no other to me.

Alright, you had written in your diary I'm awkward in black. Did that idea just kinda go away for a couple of years or did it always kinda 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 gonna come back to it and it'll just

Staying your head. It'll pop up occasionally when you're working on something else. And for me I had a vision like it's like 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 wanna 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 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 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 in 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. Um in twenty eleven, you put out your first episode of Awkward black girl.

And I mean at the by that point, I mean you knew how to do it, right? I mean I I've I've watched many, many episodes, including the very first one, which is remarkable'cause 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 and the next car um you know, that first scene, it's like did you are you ever situation where you've somebody 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 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 that 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 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. 'Cause I wanted someone else to be to play Aqua Black Girl. The the m the lead in Dorham Diaries is who I wanted to play Awkward Black Girl because 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, uh Do I really want to be In this, do I wanna 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 jugged on the internet. I mean

Uh, obviously this is a business show and but this is such a business um 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 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 and for people who haven't seen it, it it's ba it basically follows his character Jay, who's a telemarketer and and and is you know awkward has these awkward encounters in her life and um And also there you you hear her inner dialogue or monologue, I should say. And um 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 ex expensive equipment. I mean, you were funding this yourself, so were you just like kinda shooting in the daytime with h handheld cameras and occasionally a tripod and and and maybe some like boom mics? The 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 camera. Okay. Yeah. Yeah and editing it and my my little brother I asked him to create the music for it because I wanted it to have score. I want it to feel like It's real of a show. It could but the

The specificity of like this is for the internet was in my mind. I was like I'm not gonna try to make this a real T V show. I'm not gonna it's not gonna be long, it's gonna 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're finding this yourself, and it's even though you were doing it on the cheap, like, you still had to cover cost 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. Um, via favors to start helping me.

And just elevated the look of the show. And that's what started getting expensive. Yeah. And uh 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 have you heard of this thing called Kickstarter? And that's when I took it seriously. I was like, Okay, more people are saying this, maybe this is A viable way to try to raise money. Um and we Asked for thirty thousand dollars and then over thirty days, you know, people almost helped us helped us to raise almost sixty.

And that's when I felt like wow, people care about this show. Like, you know, and we 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. 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 wanna continue to see this show and you want to support us. Please give us whatever you can. Yeah. And by the way uh

At that point in this 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? I actually don't remember. I know there was above it was it had to be between thirty thousand and fifty thousand, maybe a hundred thousand. Wow How are you getting so many viewers?

That's amazing. We released it. The first Thursday of every month. Uh and that was like

a release schedule I just came up with. I 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. Got it out there. And then Matt episode got like twenty five thousand views in the first Weak I wanna say. And I remember the the guys from the F word hitting me up like what

The hell? How is this getting more views than the show we've been doing for Four seasons. Five seasons now. And I was like, I don't know, it's just I 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 were you focusing like we've had

people on on the show who started, you know, who like really focus on like search optimization or like certain words or things like or titles in the YouTube video or descriptions Were you 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 who spread the word 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. Yeah.

You raised fifty thousand dollars from this Kickstarter campaign and You start to get quite a bit of attention, including from Pharrell Williams. who I guess reach out to you because he was interested in maybe collaborating. I mean That must have been kinda mind blowing to get an email from

It was extremely mind blowing. You know, some great celebrity p support. Gabriel Yungen, I wanna say was one of the first people to like support it and spread the word about it. Ava was an early supporter. Uh but Farrell was the first person I like Call me and be like, I wanna

Like I want I want in. I wanna figure this out. And he had this You know, when Google did the hundred channels and gave Um

But 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 T V on the internet. Uh he had one of those channels and

was able to fund our second season via his uh I am other uh company. So what did that mean for the season two, like Um'cause you can see it. Like it's so cool to see the evolution of that show from the first episode to the s 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, like the second season we were actually able to pay people like a legitimate rate. Like it was

a production and it w 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 after that show started attention and and you're collaboring with Pharrell Williams that um okay And did it 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 are on a bigger stage. It increased my anxiety for sure. I mean, as these things go, like you're like, Oh, now people have expectation. They're like, Oh you got money now? Oh, for real mess makes 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. Hm. 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 This wasn't just me and let's make sure that U 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'cause it couldn't have been me. I don't I don't I don't know how to properly explain it, but that's something that I

I've realized I do even, you know. In other words, and and it it took A realization and even other people to just kinda m make me focus like this is there 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.

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. Pretty powerful people. The most exciting thing that happened to me was being able to

Page for Shawn. Shawn rhymes to me. Huge inspiration. Had Grays and scandal at the time. Killing it just as a black woman. Showrunner and

her and I got to picture her and Betsy, they bought A show idea that I had called I Hate LA 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 You know, I got the grand announcement that I was gonna be doing Developing Shana Rhyme's first comedy, and that was a big deal to me. I mean this is like twenty twelve. You launched Your sh your web show in twenty eleven. I mean that's

Amazing. Like you were pitching Sean to R like How crazy was that to sit in a room with I I've met her before at con at she she used to go to the Ted Conference, um a lot and I used to go'cause I I did a show with them and Like she's The nicest just like Just r very approachable person, but still it's Shana Rhymes. So

You're there like a year after you launch a 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's that is kinda crazy. But in some ways it felt like, Oh my gosh, this is

This is it, I'm finally here. Mm-hmm 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 Bears is one of the funniest people, uh, ever, and so they put me at ease with Their jokes and so once they were like, Oh, we wanna 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 and you still have it? Oh wow. Of course, man Uh 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'cause then it was just like, Oh no.

I'm gonna let Shonda rhyme down. And this was a show called I Hate LA Dudes and it was sold Uh the the A B C want was basically s 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 what w how did 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 are you writing it? This was just me. This was me by that time Tracy was writing on a on a ABC show. And so it was me working with one of their development executives at the time and directly with Betsy Bears because

You know, Shonda She's a queen of drama and Betsy was uh 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. Wow. There are so many cookies. Oh my gosh. And they don't all agree. And so To someone who just wants to please.

It can be maddening and and for me, like I don't think that I had a concrete vision enough. I was just like, I just wanna make a show. I just wanna work with these people and I don't really What I'm making I just wanna make with them.

That is not That's not those aren't the right ingredients to to make a good show. And so I was just like, Okay, they gave me this note, I'll make the note work. Okay, then 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.

Um, and I just I kinda just didn't know what I was doing. And I credit You know, Son of Lancaster. 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 s about about a a a woman who was dating horrible, awful image f uh obsessed men in Hollywood. And I guess you from what I understand, like you had tried to kind of

mold it in in in a way that you thought would be acceptable to a network. Um which was like Th they're you know, in the end everyone gets to come together and and the and and then you you you sort of you kind of like The the characters but it's called I Hate LA Dudes. Like, yeah.

And What's in 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 of encounters and dates and sketches, but the way you write that is different than writing uh a network show when need 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. Uh, 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. Tell me when when they ultimately decide 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 It was a Yeah, I mean 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 card were set up for me to succeed. And I 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 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? Well, Shonda. Ah

And then it's just like oh Yeah, uh different direction. You know, I'm just working on a lot of things, so You know. Um, 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 do it?

But no, like it was just it was it was really devastating and I I thought it was over for me at that. Mm. Nobody's gonna wanna work with the failure who couldn't make a show with Shauna Rhymes, who 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 to check, but I definitely remember I I I I I'm I I don't cry often. But I wanna say I cried after that. It was either that or the 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. Although I think you already had the idea of basing it around a young black woman uh 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 and had his own show and

Lots of people know Larry Willmort's shows. Um so how did that c collaboration happen? How did you how did that start? So after I sold my pics to HBO, they they bought This nonprofit idea. Um, then my managers were like, you know, you're 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, um 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 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. How I I read that you wrote the pilot in like eight days and then you revised it over s over a period of weeks, but like How did HBO respond to this pilot? I mean, that's 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 to 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 kinda 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 Uh kind of a writer's boot camp, uh 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

Mm. To them it just wasn't an HBO show yet. One of the most common questions you get. that I'll n 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? Mm. And I you know, we we were working on it for a couple of years and Larry got the nightly show opportunity.

And so that was like a 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

That's it. That's it. Again, here I go again. They're not. They're not doing it but we had we've 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 manager's like this isn't they're still not happy with the script and 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 non profit with a PH. No. And meanwhile, I mean you were also kind of

uh on the line because I think around around this time you had actually launched something Completely different. A a whole separate venture which w which would be the beginnings of a management company, your own business. Yes. It was called Color Creative and it was initially it was supposed to be a program for discovering writers.

And uh 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 fifty thousand dollars each and I thought I was gonna have money coming in. I was supposed to have money 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 to but I was like counting on This coming through.

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. Um and I've yeah, I've made a mistake.

Like I put all my eggs in this basket in these well, two baskets. So m you are simultaneously financing pilots. That you put all your money in and Counting on this

This insecure. deal to go through and still. 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 would your version of like a Laverne and Shirley look like? They're talking about the character of Molly. They're 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 and that's what they ultimately Ended up picking it.

It's amazing because and I mean television's really takes a long time and it really is underscored by this timeline'cause like You started talking to them in February of twenty thirteen to HBO and the pilot debut in September of twenty sixteen. 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? Well people and then you make the pilot and then it's like Are they gonna renew it? Are they gonna people gonna watch it?

Yeah. I mean the The pilot process Was the most rewarding hard because because of that fear

Yeah. 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 Nino, they picked that up In days. They picked it up really quickly, 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 and Um figuring out what our voice would be, how it would be different from anything else on T V. That show of course went through five seasons and and and um finished the final season in at the end of twenty twenty one. It was

A critically acclaimed show. But w which is 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 gotta be I mean, I can't imagine how hard it is just to write a script that is because you you wanna make something that people are gonna love and just every word, every scene, every moment

J to do that to make it good has gotta 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 Um, 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 s essential for our show is for Me and the writers to live lives'cause that was the material that went into the show. Yeah. And the advantage of being on a cable network Is

Not being behold into a specific release schedule. Um, you know, and being able to say hey We wanna 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. 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 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 'Cause a lot of artists, you know, they make art, right? a lot of people in in the creative space make their art and don't think about the business side, but it's really important, especially if you want to r retain control over your process and your your work. When did you start to to think to yourself, I This is a business too. I'm not just making

You know Art and content. I have to Say with the F word. The effort 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 Easter A productions. Because I I was like, Well I'm just creating internet content. So I call it Israe Presentations. Mm-hmm.

And I was just like okay, I'm I'm doing something. I'm making a product. I 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. Yes. Um 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. And then Color Creative was

Initially I guess. as you described like initially was designed to identify talent and then develop scripts. And and sort of uh that was originally kind of a a production company, right? Yeah, it was like a pipeline initially. It was meant to be a pipeline to Mm.

Bring in Creators of colour. into the industry. using the model that I was able to to do with Awkward Black Girl in in terms of creating a product, getting an audio 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. You know, some of the writers that came.

All of the writers that came out of that I 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

Helping them to find their next projects, whether it's recommending them to writers room or initiatives or to write on certain films and Uh 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

Um a management company. Alright, so you have Hooray Media today, you fo formally found in twenty twenty, but but you had already had Color Creative and now that sort of Under This. kind of umbrella media company. You've got a radio division R A E.

D. Which I love, and then um a T V and film division. So Tell me a little bit about the vision. Um I mean You had this

incredibly successful show with HBO and you've got a new show on HBO Max and I uh uh uh big deal that you signed with Warner Media. um to produce more more content, more films for HPO, HBO Max, Warner Brothers, et cetera. You've got

Twive plus employees maybe more at this point. Um What do you w where's it going? Wh what's it gonna be in A year, five years, ten years from now. Yeah, I mean I'm on a an ecosystem w right now

with the new Sean HBO Max, uh Rap. Shut? 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 uh as We shot it, we had color creative directors. You know, come on and and help. Direct some of the episodes and

Just all parts of the company touch it. Um, radio's also doing the soundtrack. And we just want to be self sustaining and We wanna compete? with the best media companies out there down the line I wanna have a studio in South LA. I wanna 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 I interviewed Nick Krull

for another show I do um recently and I was Ask him about performing in front of his parents'cause a lot of his work is um you know adult oriented humor. And and um you know, on your shows like you're talking about sex in your sex life and things like that and I

Um is it ever I don't know, is it ever w awkward to like watch it or or like n know that your parents watch it too? Oh my god. When I tell you this show I we just had a premiere for Rhapsit 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 thirteen movies till I was thirteen, rated our movies till I was seventeen. 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 she shielded me from she just can't handle and There's a Big sex scene.

At the end of the second episode during the premiere, we're sitting in this theater. And What sex is like I watched her watch the first episode. And like beat into it and 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 I'm feeling the tension.

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, Jeez And even afterwards she was just like She's it's just not for her. And I realized, you know what? I'm never inviting her to a premiere again.

Be 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 it does kinda suck, but It's her fault she made me. And um I guess your dad is is Happy even though you haven't become a doctor. Yes, my dad is satisfied.

He's experiencing the 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 were like, Oh, here's his overnight success story.

But in actual fact, like it was a An overnight success story that took twenty fifteen years. Yeah. I d I don't fault people for not knowing in some ways, you know, I'm just happy they're here. Uh 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 Shawn. Sometimes I 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 in 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 that's a different feeling. Uh Wow. You're you're in your thirties. 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 w what kids will do to that and what you know expanding a fan and starting a family looks like.'Cause you got married last year, congratulations. I d I did. So there's just

There's just other facets that I have to consider that I I was not thinking about in my twenties when I got started. When you think about this s your story and this trajectory and all that 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 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 Th I I say it's seventy percent work. thirty percent luck in some ways. And that 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 those moments. That's E Saree.

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. I'ma do the naughty pop and get damn naughty nap. 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 hibt at id.wondery.com.

If you want to follow us on Twitter, our account is atHowIBiltThis and mine is at guyRoz. On Instagram, we're at howIBilt This and I'm at guy.Roz. This episode was produced by Liz Metzger with music composed by Ramteen Eriblui. It was edited by Neva Grant. Our audio engineers were Patrick Murray and James Willits. My production staff also includes JC Howard, Carrie Thompson, Alex Chung, Josh Lash, Sam Paulsen, Catherine Cypher, Elaine Coates, John Isabella,

Chris Massini and Carla Estevez. I'm Guy Raz, and you've been listening. to how I built this.

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