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Issa Rae is an actress and creator who is best known for her work on “Insecure” which has been running for five seasons on HBO. In this episode, Issa shares her journey with Warner and the importance of ‘ownership’ in the industry, which has been a growing topic especially for a lot of black creators like herself. She also talks about the final week of “Insecure” and her plans moving forward.
Listen and be inspired by Issa’s story, achieving something that is often deemed unattainable: living your passion, creating engaging content, and being financially successful.
[02:56] What to expect from the final week of “Insecure”
[07:26] How the value of ‘ownership’ play a factor in the decisions in her content
[11:01] Why her experience with Warner, specifically, HBO is the best decision
[14:13] On working on the digital side to expand her business
[19:41] What was her take on Quibi
[22:39] On which of the multiple hats would Isaa want to have more focused on moving forward
[29:12] Big announcement on things to keep a lookout for in 2022
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Host: Dan Runcie, @RuncieDan, trapital.co
Guest: Issa Rae, @IssaRae, issarae.com
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Dan: Hey, welcome to the Trapital Podcast. I’m your host and the founder of Trapital, Dan Runcie. This podcast is your place for conversations with execs in music and media, hip hop’s heavy hitters, and the leaders that are taking this culture to the next level.
On today’s pod, we’re joined by the one and only Issa Rae. She came through at a great time because Insecure is closing its doors. The show has been running for five seasons on HBO so we talked a lot about what it means to Issa, how she feels about it, and most importantly, what’s next for her moving forward.
One of the things that Issa’s talked about in past interviews that always stuck out to me is her perspective on ownership. It’s clearly been a growing topic and importance, especially for a lot of black creators, and Issa’s talked about the fact that she doesn’t own Insecure, HBO does, so we talked about some of the trade-offs with that, how she looks at her career, and how the deal that she signed with Warner Media intersects with that, because I think that’s a trade-off that a lot of creators often look at at many levels.
And then we also talked about the synergy map. For those folks that have been reading and listening to Trapital for a while, you’re likely familiar with the Issa Rae essay that I wrote in 2020. If you’re not, there’s a link to it in the show notes for you to check it out.
And there is a synergy map that was my vision of how I saw each of the businesses intersecting with what Issa is doing and what she’s building towards so it was great to talk to her about that, get her perspective on it, and ultimately where it’s going, because one of the things that it focuses on that I think is so relevant to a number of creators out there is that many of us are multi-hyphenate,
but, at a particular point, there’s likely a preference of which of those hyphenates we wanna spend a bit more time on. Do you wanna be more of the creator? Or do you wanna be more of the CEO? And if you’re focusing on those areas, who are the people you partner with and how do you help maximize those things that reflect your personal preferences but also getting the business to the highest levels that it can potentially go to?
This is why I think it’s so dope to talk to someone like Issa. Her journey, even though she’s doing it at reaching that mogul level, it is very relevant to a lot of the people that are thinking about so many of these trade-offs and so many of the same decisions that are much earlier in their stages of being a creator in this space.
So, I hope you enjoy this conversation. It’s really great to have these full circle ones where it’s people that have been broken down and discussed and been popular topics in Trapital that you actually get to talk shop with for a bit of time, so I hope you enjoyed this conversation. I really did too. Here’s my chat with Issa Rae.
Dan: All right, today on the Trapital Podcast, we got Issa Rae who is here with us. Issa, first off, welcome to the podcast. It’s great to have you.
Issa: Thank you for having me.
Dan: Yeah, thank you. I’m glad you can make it happen. And I gotta ask, we’re at the final week now for Insecure, everything is closing up, tying up all the loose ends. How does it feel? I feel like this is a big step in your career just with everything that you’ve been building up for well over the past decade now.
Issa: Yeah, I mean, it’s a lot of pressure. I’m feeling it. A lot of people have opinions in my mentions, a lot of threats, which I think is interesting. But I’m just proud of being able to end a story that we’ve been working on for, you know, six years now, that I’ve been working on for eight, and I have loved every moment of this experience, creating this show, to have such a rabid fan base of viewers is a dream come true. So I’m just gonna relish that until the finale airs and I’ll disappear.
Dan: Talk to me about these threats though. I mean, are these just like crazy fans getting wild about stuff? Like what’s going on there?
Issa: The threats about like how the ending should be, how long the final episodes should be, what Issa should and should not do. It’s a lot of choices. You know, people have a lot of opinions about the season, but they’ve always had opinions about the show so it’s kinda just par for the course at this point.
Dan: Yeah, I can imagine that. And I’m curious with the show that clearly I think taps into so much discussion from Twitter and places like that, especially some of the themes you cover, do you feel like you have this balance of what you want yourselves and showrunners to stick to as what you want the outcome to be versus what you think the audience may react to or prefer in one particular way or the other?
Issa: Yeah, I mean, I think for – since jump, I’ve always had to say that this is a very specific story and, you know, this story can’t encapsulate the entire black experience. Nothing can. It can’t encapsulate the entire black female experience. This is literally, you know, a story about me and my friends and some of my experiences and it’s taken – these experiences are taken from the writers in the room as well.
And I’ve seen over time, people have kind of projected what they want the show to be or what they think the show should be, despite, you know, that declaration. They’ve made it a show about for black women, which it’s not. They’ve made it a show about gender wars, which it’s not. They call it arguing time.
And, you know, we’ve just always stuck to the idea that this is a show about, one, a girl who’s trying to figure out who she is and where she’s going and the friendship between these two women and I think when you look at the series from that lens, that’s the story we’ve continued to tell over the course of five seasons.
Dan: Right. I think that’s a good point that I think people forget, because, at least from the conversations I’ve had, people often try to almost pigeonhole the show in terms of what they may expect, right?
They may compare it to some other type of show, be like, well, it’s like X but for this, and it’s like, “No, I think this is a new type of story she’s trying to tell. This is why they have it,” but whether they wanna say, “Oh, it’s like Girlfriends but for this,” or, “It’s like Sex and the City or Girls for this,” and it’s like, no, I think this is something different.
Issa: Yeah. And I think the sooner that you kind of resign to the story that we are telling, I think you almost appreciate it more. But I think part of the fun for people of watching the series is the discussions around it and, you know, the passionate opinions. So I’m not trying to rob anybody from that experience. Far be it from me to tell you what the show is about.
Dan: Right. And I could tell based on the show itself there’s clearly things that are tying into themes that people have been arguing about for a while, but some stuff even surprises be, like there is the episode earlier this season when Amanda Seales’s character was wearing the sorority letters and then everyone went wild and it was just like, how do people not separate that stuff? That that’s wild to me.
Issa: Yeah, that was super unexpected for us. We did not put that on bingo card of things to argue with people, for people to argue about. But, you know, they got over that the next week. We overcame, I guess.
Dan: No, definitely, definitely. And now that this is wrapping up for you, I’m sure you’re already looking, you already have things play a next and one of the things that you had said in an interview that always stuck out to me, you talked a lot about ownership and I feel like that’s been a common theme in following you and your business was seeing you talk about how you don’t own Insecure, HBO does.
And I’m curious how ownership may play a factor in the future decisions that you make and the content that you may put out moving forward?
Issa: I think that’s a great question and something that, you know, I’m grappling with, just because of the way that the industry is set up. Like that’s not necessarily set up for me to do at this point but I’m seeing, you know, moves being made and, you know, equity stakes in certain companies and, you know, I’m a proud owner of my production company and my media company, and that comes with its own face, the creative properties that I create, I think that is the next step.
But it’s also like you’re trading in at this point, you know, I have a deal with Warner and that means that they pay you a particular amount to be able to have access to the things that you create. So right now it’s a trade-off, do I wanna make, you know, a certain amount of money and, you know, give my ideas to this company at this time with the distribution – with the guarantee of distribution on a platform that I very much respect? Yeah, I don’t mind that.
But in the future, do I wanna be able to own the distribution platform? Do I wanna be able to have control that? Maybe. I think about the Oprah model a lot and I think that’s so powerful and that’s aspirational, but that’s also a lot of work.
And over the last couple of weeks, I’ve been asking myself, like, “Oh, what am I building towards? What do I want? Do I want that? Do I wanna grow at that rate?” And I do look at Oprah as a model and I see like, okay, she’s chilling in her garden, she seems like she gets some off time. Like she’s over there, you know, spending quality time with Stedman, it seems like she has achieved some sort of balance, but I can’t imagine that in my life right now. I’m hungry for it but I don’t know how hungry I am.
Dan: Yeah, that trade-off is real because, I mean, it’s the same thing you hear in music, it’s the same thing here and other forms of entertainment. And, yeah, I feel like that back and forth is legit, because I feel like Oprah herself has clearly accomplished so much but when you think about, okay, what she had to either sacrifice or what trade-offs that she made to get there and then what does the alternative path look like, right?
Because there are options now available to you, for instance, that weren’t necessarily available to someone like Oprah when she was at your stage in her career, right? So there’s never like a right or wrong answer. So much of it really comes down to your personal preference.
Issa: That’s entirely true. And, you know, we do different things. You know, Oprah was a gifted interviewer and, you know, personality. And, you know, I am a creator, at the end of the day, and I think, right now, it is, at this very moment, really valuable to have a network and a studio paying for my ideas directly. I think that that’s valuable for me right now.
Dan: Definitely. And just given the trajectory of everything that you have going on, that seems like it’s the right move for you and I imagine that a lot of that was part of the decision before you had made that deal with Warner Media, right? Like you saw where the future was but, at that point, I’m sure that it was either, okay, I could go on this path and continue, but even at that point, was there any consideration about what another option could have looked like before you had taken that deal?
Issa: Yeah, I mean, there’s always the option to obviously see what other places are offering, but I’ve loved my experience, particularly with HBO, so, so much, that, you know, that was an option that I didn’t necessarily wanna consider so I’m glad that they stepped up to the plate.
And, of course, there are options to just be completely independent and, you know, go play by play – I mean, yeah, on a play-by-play basis. And that just felt like also a lot of work and it could have been, you know, profitable at the end of the day, but I liked having a home.
And then also just given the work that we were doing with so many other creators and giving them opportunities to showcase their work and having sort of a quick pipeline that allows us to do that. And, obviously, we’re restricted from going to different places with this deal but, for the most part, like that’s just been incredible, even for the prestige of creators that we wanna work with.
So, we entertain other decisions but I stand by the fact that this was the best decision for us.
Dan: Yeah. And I think one thing that you’re highlighting the fact that things were going well, you wanted to continue with HBO and that family. I think sometimes the relationship piece can be ignored from the outside, because I remember Roy Wood Jr. was talking about this once and he was saying how, when there were other opportunities to go outside of the Comedy Central umbrella, he’s like, hey, sometimes for us, you may not always have the opportunities elsewhere and you don’t know what it’s like if you just go for the bag and then this employer isn’t quite lined up with you, and –
Issa: Oh, my God.
Dan: — you never know what could have happened and having that support system in place, especially when you hear these deals of like what Shonda Rhimes had went through at ABC or some of these other places, you wanna be with people that have your back and trusted. You can’t necessarily always put a dollar on that element.
Issa: Extremely well said, and, yes, I stand by that 100 percent. I think it’s so rewarding, especially as a creative that values constructive feedback to be able to trust partners to give you just that, and that’s rare. I love that, you know, within the Max and HBO family, like I work with executives whose feedback and critique that I trust and I think that that’s invaluable. To go for the bigger bag at a place where that is up in the air and you kinda rebuild those relationships and kinda reintroduce myself is also a cost. So, completely agree.
Dan: Yeah, one of the things, and you talked about this a little bit earlier, one of the things that I always liked about your model is that even though you may have the bigger opportunities as one of the primary things you’re doing, you still have the other things that you’re working on, whether it’s, (a), the platform you’re providing to other creators through radio or through other opportunities you’re doing,
but then also what you’re still doing on the digital side or what you’re still doing through other channels. So, yeah, this is the piece that I own. This is the stuff that I’m still doing it and you haven’t stopped that even though I think it could be very easy for someone to see why you would shift your priorities but, no, like you’ve kept that,
whether it’s the family or the connections in the community you’ve made on those platforms where you have a bit more control and that’s something I liked, because I think that shows the flexibility and I think that stems back to who you were even when you, you know, started on YouTube and building in places like that.
Issa: Yeah, thank you for that. Some may think that it’s exhausting. (A), it is, but I can’t, for some reason, stop, and I think, even to what you said, the different divisions also have taken that on, so even Benoni making the most of the label deal and expanding that to, you know, music supervision and publishing and all these other components that obviously advance and color creative in addition to being a talent management company striving to build talent businesses,
and of course, our digital side is expanding to so many other divisions that I can’t fully talk about just yet but like we – that that is the model within the company and with all the department leaders.
Dan: Yeah, no, that makes sense. And that actually reminds me – hearing you break it down that way reminds me of the synergy map. And the essay that I had written a year ago about you and your business and everything you’re doing.
And I remember when I had talked Benoni about it and he was like, you know, I think, generally, you know, you got a lot of the pieces there. There are a few things that are, you know, a little different but I think generally you’re there. I’m curious, what was your take? What was your thought when you had checked that out?
Issa: I thought it was really cool. He’s the one who sent it to me and was like, look, this is dope, someone sees what we’re doing and what we’re attempting to do. And I was like, oh, amazing, and I think had the same reactions of just like, okay, so we also need to be clear like intercompany wise of just like what our missions are for each division. But it was just – it was really, really validating to see that, you know, you saw the vision.
Dan: Yeah. And I saw too when you all had put out that video announcing or reintroducing the rebrand is HOORAE and this is where everything is, it was like, okay, it was cool to see how you all had pointed the arrows too between color creatives, radio, and each piece of everything you were doing and how that serves up to it as well.
So, yeah, I think that, especially now, just given the way media is, a lot of those intersections are attainable in a way where, yeah, you know, in the 50s, a company like Disney clearly had an advantage that a lot of others didn’t. But even at a more personal scale or even at a more rising scale, a lot of this is achievable if you’re building and thinking about it the right way.
Issa: Yeah, absolutely, and I think there’s just – the promise of sustainability and, you know, self-sustainability, rather, and the synergy between these companies, and even intercompany wise, I’m finding like there’s the opportunity to collaborate and also just build off of each other so I think while self-sustainability is important, also finding the pieces where we can connect and help each other grow is great. Otherwise, we’re kinda siphoning ourselves off to just these very specific audiences. I don’t think anybody wants that.
But it is interesting to see how the industry has allowed for the, in some ways, by also eating itself. And I find it so – I don’t know if it’s troubling just yet but the idea that these streaming models are becoming like, you know, the big five networks that existed back in the day. I do give a lot of props to what I see are emerging platforms that are competing on an independent level and I’m really curious to see what happens there.
Dan: Do you see yourself maybe more likely to try to do a deal on one of those independent or rising ones to be like, okay, there could be an early mover advantage here or you never know what could happen with one of these opportunities?
Issa: I don’t know. I mean, it depends on what the offer looks like and what – like at this point, you have to have a lot of eyeballs, you know? And you’re competing with a lot of eyeballs. So I think some of these independent platforms that are sprouting up really have to tempt with content.
I don’t think it’s enough anymore to be like, “Oh, I have a vault of your favorite shows,” because now you have the existing studios that can do that on their own with their own platform. So kind of what are you offering? What show could be compelling enough, for lack of a better example, like what’s your House of Cards that’s gonna draw me to your platform? And is that enough? So, I don’t know just yet. There’s a lot of work that needs to be done.
Dan: Yeah, no, that’s real. I’m curious, what was your take on Quibi from last year? I mean, I could only imagine – I didn’t think that you had anything on deck with them but I imagined that they could have easily reached out and been like, “Oh, hey, do you want to have something with us as we get this big thing out here?”
Issa: Yeah, Quibi was one of those things where I was like, what the fuck? Are they serious with this shit? But I wasn’t also gonna turn down a bag. And I will add mine because I did, but that was just like there wasn’t much – it didn’t excite me and it’s hard for me to create for something that doesn’t necessarily excite me. Also something that I wouldn’t use myself.
And I think the model – and it’s easy to sit on something when it’s done, and I don’t wanna do that, but, for me, honestly, it was like, no, I don’t wanna watch something for seven minutes while I’m standing in line, like that’s what you’re basing it off of, I love to live in a world, like it’s the same reason I don’t love to watch movies as much anymore, because I wanna live in the world of television shows.
I wanna watch six hours of content. So to, you know, relegate something to even a shorter form just didn’t really excite me as much, but they were paying bank and I definitely alley-oop’d some people to some Quibi deals but I had no interest myself.
Dan: Nice. Yeah, I could see that. And it’s, like you said, it’s easy to shit on a company like that after the fact, right? And, clearly, there was a lot of interest from a lot of people. But, yeah, it’s this thing where, in the moment, it can be so hard to judge these things but I think you need a balance of, obviously, some big name talent, which I think Quibi did have,
but you also need some, at least one type of anchor show that brings everyone in, whether that is, yeah, what House of Cards did in 2012 when everyone was watching that. And then maybe even a mix of some evergreen content that people are gonna wanna go back to, that they’re already familiar with, whether it’s your Friends or The Office or like one of those types of shows.
And I think now it’s just tough to maybe get all of those things. And now just with so many streaming services, you really need to have something that is a big hit in order to cross through. It’s like it’s not good enough just to be like an okay show, like you need to have something that people are talking about everywhere.
Issa: Yeah, it’s so competitive. But even thinking about Apple, how hard it initially was, and they had, you know, Morning Show out the gate with this A-list talent. They had like star-studded shows and it still took a minute. And, obviously, Apple’s easier because so many of us have iPhones and they made it compelling. But if it’s hard for a company like Apple, it’s gonna be hard for an independent to come in out the gates swinging.
Dan: Right, like that’s proving that money alone doesn’t solve this, like you clearly need a bit more than just the bag to bring eyeballs to whatever your content is.
Issa: Oh, yeah.
Dan: Yeah. I’m curious for you, because when I think about you and the businesses you’re building, you’ve always been creator first and then you have all the other things that you do, whether it is acting, producing, writing, etc., and being an executive in music as well.
And part of this, I think, is a bit related to you, as you mentioned earlier, looking at someone like an Oprah and maybe what you wanna build towards but do you see the – I guess the balance that you have right now in terms of those different hats you wear versus what you may want it to be ten years from now or what you may want it to be in the future?
Like which of the multiple hats you wear, the multi-hyphenates, like which of those would you want to have more focus on moving forward?
Issa: Oh, yeah, I mean, it’s something that I mentioned I’ve been thinking a lot about. And kind of deciding. I definitely don’t want the same bandwidth ten years from now and, you know, for the next couple of years, I know I’m gonna go hard. I just – I know that. I think this year will be – this is the first time that I’m not like in anything and that frees up so much of my time.
Insecure took up nine months out of every year for the last six years and so to be able to not have that and focus on growing the business and focus on my creative endeavors really, really excites me and I wanna see what I do this year, what I’m able to do, and then go from there.
So this is almost like a restart for me in a really exciting way. But do I wanna be juggling and managing people and be a CEO in that sense? No, I really love the creative part a lot more than I do the business side. The business side has just kind of accompanied being able to create at this level, but I’ve been able to meet so many capable leaders and entrusting them has just been better for me and I hope to continue to do that.
Dan: Yeah, I think that that distinction, you know, being the person leading the business versus being the lead creator yourself, that’s something that everyone is deciding and I think for people to hear that you yourself still go back and forth, not necessarily with which one you prefer but in the roles you’ve had throughout your career, that’s real, because I think that anyone starting out, especially once you get to a certain level, you need to have a balance in terms of, okay, how are you looking at where your skill set are and what you’re most interested in.
And I think with that, that just allows everything else to grow because if I think about someone like you, you’re definitely in the position where you can continue to have, not just as you already do, the entire team that’s around you supporting everything that you do, but if that’s maximized to the highest potential that it is moving forward, then it really could be completely up to you on what you choose to spend your time because anything else can be done through partnership with someone else.
I mean, I think that’s the conversations that a lot of other folks that I know, whether it’s folks that are doing more things on the writing side or things in content production, but sometimes I think it’s reassuring for people to hear, “Oh, she’s thinking through things the same way that we are,” right? Especially in your role.
Issa: Without a doubt. And, you know, what you just described is I think more of a dream for me to just kind of lean on that side of it more, and sometimes it doesn’t feel within reach the more I continue down this path, but, you know, you might talk to me after this year and I might be like, you know what, I fuck with the business side and this creative shit I can lead to these other people that I’m fans of.
So, who knows, but I really do think this year is a determining factor for me.
Dan: I feel like investing is one of those things that I’m gonna hear you have some big announcement about, like use your platform, be like, oh, Issa Rae just opened up a fund, she’s gonna invest in these types of businesses, X, Y, and Z. I can like feel that coming.
Issa: You’re speaking Benoni’s language right now. You know, that’s another thing that I love about having capable leaders is, you know, they’re always pushing ideas my way that I may not have otherwise considered.
Dan: Yeah, because I – and I think with that, too, like whether it’s things like the coffee shop, for instance, there was definitely some leading towards that where people were like, okay, you can see the opportunity there.
But, yeah, I mean, it’s such a fascinating time. One, it’s almost impossible to keep up with all of the new changes that are happening but when you are in the position you’re in, it’s literally like you could do whatever, right? And it’s truly a bit more like, Okay, what am I a bit more interested in –
Issa: Exactly that, like I don’t let him to just do whatever and I’ve said that. There’s something that’s coming out soon next year that I’m really excited about, that is a venture in that way, where I’m kind of like, this is kind of the last thing that I wanna put my weight behind in a way that I really believe it.
I don’t wanna, you know, I do get opportunities to obviously sell certain things and put my name on certain things, but I only wanna do things that, you know, that I believe in and that I want for myself and that’s been my model, even for the things that I make and the content that I create, like what do I really wanna watch? What do I miss?
And the businesses that I ultimately invest in, what do I actually need and what do I want to have control over in some way? So, beyond this, I’m not sure that – I also don’t wanna be the person who just sells everything like the Chucks, I wear Chucks all the time, I wanted my own shoe, did that.
The coffee shop, obviously, like that has been a life — that’s been a dream of mine. Lifelong is too long but, you know, since college, and have been able to do that and make sense. Hair is such a big part of my journey and hair care and I just – I only wanna continue to do things that get me as excited as those things.
Dan: Definitely, yeah, that and it ties back to your brand, right? You have a very identifiable persona of like people can be like, Oh, I could see Issa doing this, I could not see Issa doing that and –
Dan: — I think that, you know, as long as people aren’t as – going as wild as they may be about Insecure plot developments as they do about that, I think you’ll be in good shape there.
Dan: Yeah. All right, well, we’re getting to the tail end here but before we let you go, you already announced a few things and I know you can’t announce a bunch of stuff, things are under wraps, but what are some things that we should keep a lookout for in 2022?
Issa: Oh, you can look out for Rap Sh*t which we just finished a couple of weeks ago, and that is airing in 2022. We’re really excited about Project Greenlight that’s underway. We’re trying to narrow down these directors and also, excuse me, I’m trying to figure out the judging panel and the people who will be kind of shaping the series and mentors alongside.
And then really just like trying to lock down the feature film side and what I want my next written project to be. A couple of things – I’m so sorry – are in the works but I just really wanna be precious about what HOORAE’s film debut is gonna be.
And so I’m hopefully figuring that out over the break. But most exciting, I’m taking like all of January off and I’m just hyped to be gone and be with myself.
Dan: Nice. I hear that. Are you going anywhere or you’re just chilling in – or you’re just chilling for the month of January?
Issa: All of the above.
Dan: Good stuff. Good stuff. Well, Issa, excited for next year, excited for Rap Sh*t and everything else you got on deck and appreciate you making time for this. It’s always great, especially to talk to the people that have been a focus in terms of not just what Trapital is building but in terms of the and so relatable to everything. So, thank you for that. Appreciate it.
Issa: Thank you for following the journey and showcasing it and thank you for all you do and the highlighting. You know, creatives and business throughout. You’re doing spectacular work so pleasure to talk to you.
Dan: Thank you. Likewise. Appreciate that.
Issa: Have a good one.
Dan: You too.