- 7 weeks ago
Issa Rae truly does it all. Not only is she a multifaceted entertainment powerhouse, but she also runs businesses in various industries—from prosecco to food to haircare. Today on the show, the former Marie Claire cover star joins us to talk about money, power, and style, including how she crowdfunded her early projects like Awkward Black Girl, how she overcame "grateful to be here" energy after partnering with HBO, and what it means to be boldly elegant in her style. She also tells us about her newest projects: her book I Should Be Smarter by Now and her two-part docuseries Seen and Heard. Plus, Rae shares why creativity is not the most important trait to be successful in the entertainment industry.
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00:00He was like, African-American studies, you might as well have majored in flowers.
00:03He was so bad.
00:06Flowers is crazy.
00:12Issa Rae, former Marie Claire cover star.
00:15Hello.
00:15Welcome to Nice Talk.
00:16Thank you so much for having me.
00:18I'm so thrilled to have you on.
00:19Let's take it back for a second.
00:21When you were growing up, what was your understanding of what I like to call the big three, which is
00:26money, style and power?
00:27Zero.
00:28It was something that I had to learn over time.
00:30I recognized some dynamics at play with my parents.
00:35My mom was always stylish, but I remember feeling like you have to earn a lot of these things.
00:42My dad was very much dismissive of social status, of all these things.
00:48He was just like, we're noble people and you can't get wrapped up in the power and money dynamics.
00:55You just have to work hard and you earn what you get and stay humble.
00:59And then on the style side, I felt like my mother was the epitome of style and it was just
01:05something that I couldn't keep up with.
01:06And she was always frustrated with me.
01:08She wanted me to be...
01:09I was the first girl, third of five children.
01:11And she was so excited to have a girl to like making her image and dress up and do all
01:16these things and put on dresses.
01:17And I was just, I was just not a girly girl.
01:19Like I did not want that.
01:21And it wasn't until my little sister came along where she was like, okay, finally, I have my girl.
01:24Great.
01:25You can do your thing.
01:26What was it about your mom's style?
01:28What was it like?
01:29She was just black mom, different hairstyles every week.
01:33She was just, she always loved to color her hair and experiment.
01:37She loved clothes.
01:38She was always well put together.
01:40She spent time in France in her college years.
01:44And then when she went to Senegal, she loved the patterns there and got into like Senegalese clothing and just
01:51always just had a love of fashion.
01:54And I didn't recognize that that wasn't everybody's journey.
01:57It felt like a standard.
01:58And I took it for granted until I looked back and I was like, my mom was really out here
02:01with five kids just still killing it and looking great.
02:05I love that.
02:06So you grew up in LA and Maryland and Senegal.
02:09And I'm curious how those places informed your sense of self and identity when you were growing up.
02:16Moving around a lot just automatically makes you kind of insecure in some ways.
02:20But it was also an opportunity to reinvent myself.
02:23And I think that was the first form of acting and writing that I did of just like, oh, I
02:29get to be this person to these people and carry that and then start over again at the next spot.
02:35Like, who am I going to be here?
02:36Being in Senegal for sure shaped me.
02:39And then like, obviously around Black people everywhere and then moving to Maryland where it was just not that, where
02:47I was like the only one in spaces definitely shifted.
02:50Like, I mean, that formed my kind of outsider perspective and a lot of that.
02:56And then even coming back to LA from Maryland, a lot of my awkward stories, a lot of my outsider
03:04out of placeness came from that era.
03:07I'm curious when you were growing up, you know, your father is Senegalese, your mom is from Louisiana, is it?
03:13Yeah. So you grew up in like a part immigrant household.
03:16When I have people on the show who have that sort of similar background to me, I'm curious, like, did
03:21you feel the pressure to choose a quote unquote practical career, doctor, lawyer, banker, or were your parents open to
03:27the less conventional path?
03:29No, my dad was very, you know, he was a doctor.
03:31He had a clinic in Inglewood.
03:33He was, you know, I got to see his effect on community and he wanted one of us at least
03:39to be a doctor.
03:40And I went to a high school, King Drew, in Compton slash Watts that was like geared towards helping black
03:49kids, black and brown kids become doctors.
03:51And it was dope.
03:52We had a hospital program and he was just like, oh, this is great.
03:54I'm going to have a daughter that's going to go into medicine.
03:57And I was that was when I discovered my love of writing.
03:59But I was like, oh, maybe I could do both.
04:01Maybe I could be a doctor who writes.
04:03And then I discovered in high school that I just did not like to see people in pain.
04:06I mean, we I was in labor and delivery and it was the first time I got to see after
04:11birth.
04:11And I was like, what is it?
04:14Nobody tells you about this part.
04:17This is disgusting.
04:18No.
04:19And so when I told him I didn't want to be a doctor anymore, he was like, oh, that's OK.
04:21You can be a lawyer.
04:22You can be a business person.
04:24Like, there's other tracks for you.
04:27And Ryder was not one of those tracks.
04:29No, he was just like, that's that could be your plan B.
04:33Up until I got insecure, he was like, you can still go to grad school.
04:36And he jokes about it now.
04:38But yeah, he holds on to it.
04:39He's proud and all that.
04:40But he's just like, you need to have that higher education because you just never know.
04:46I always say the same thing.
04:47My parents were very much so like, so when are you going to grad school?
04:50And I'm like, I am a senior style editor at Glamour.
04:54There is no grad school.
04:55This is my grad school.
04:56We're done.
04:56But what I do think is interesting is that you attended Stanford and you studied African and African-American studies
05:01with a minor in poli sci.
05:03So, I mean, that feels pretty major to me.
05:05Sure.
05:05I mean, he was so pissed.
05:07He was he thought I majored in poli sci because I was taking all the classes and I was just
05:11like, I didn't literally it was like, why do you want to major in poli sci?
05:14And all I could think of was because my dad wanted me to.
05:17Yeah.
05:17I was like, I'm taking both African and African-American studies.
05:20I can do writing.
05:21I can do, you know, drama, all these other things.
05:24And he didn't find out that I didn't major until he came to the graduation.
05:28He was like, African-American studies, you might as well have majored in flowers.
05:32He was so bad.
05:33Flowers is crazy.
05:36Yeah.
05:37That is so funny.
05:38But, you know, after graduating, Awkward Black Girl went incredibly viral, which is huge.
05:43I'm curious that what was sort of like, because our parents want us to go into these careers because of
05:49financial safety.
05:50Right.
05:50You had Awkward Black Girl.
05:52Overall, it was huge.
05:54But like, what was your financial situation then?
05:56Like, how were you funding your creative projects at the time?
06:01Man, through favors.
06:03Asking for help is really, really hard.
06:05And I got really lucky because when I put out the first episode, people came to me and they were
06:11just like, you know, it seems like you need lighting up.
06:14I had a friend from college who watched the first episode.
06:16She was like, this is good, girl.
06:18Like, let me help you bring on a crew.
06:19Let me let me produce it with you.
06:21And so that helped.
06:22But then after a while, after a couple episodes in, I was like, I got to pay these people.
06:26Like, they're giving their time.
06:28And Kickstarter really helped.
06:30And that helped.
06:31We were able to raise money there.
06:32We went on like a college tour.
06:35And, but I was never secure financially until probably we did the second season of Awkward Black Girl.
06:41And that's when, no, I still wasn't secure.
06:44I don't think I was financially secure until, until insecure.
06:48Because that was like a consistent paycheck, I'd say.
06:51And everything else was kind of just like scrounging.
06:53But my, I, I got blessed with an angel during Awkward Black Girl.
06:58Someone who worked at Vibe.
06:59I wish I could remember his name.
07:00I don't know what, what, what finesse it was.
07:02But he was like, I can get ad clicks on Awkward Black Girl through this website.
07:07And that was like supporting us for a while.
07:09And then he just disappeared off the face of the earth.
07:11But I got like a fact check.
07:13A true angel.
07:14True angel.
07:15I don't know who it was, but whoever you are, thank you, you helped float me for like six months.
07:20So you mentioned Insecure.
07:21In 2016, it premiered on HBO.
07:24How did it feel going from, you know, being your own boss on Awkward Black Girl to answering to a
07:29network?
07:30It was frustrating initially.
07:32I mean, obviously the first, initially was exciting.
07:34Because that was my dream network to be on.
07:36But then during the two to three year development process after a while.
07:41And watching other people who had projects alongside me not get their stuff made or get dropped.
07:46I was just like, what am I?
07:48Like, I could have been made this show online.
07:50What is going on?
07:51What is this process?
07:52And then, and then the notes process, like I love feedback and stuff.
07:55But it was just, it felt like I wasn't getting what they wanted until they finally kind of made it
08:00plain of just what they were looking for.
08:02Or we were like, they were like, we want this, this show that can kind of be a black version
08:07of, yeah, shows past, like a coming of age black story.
08:10And so it wasn't that initially.
08:12It was more of a workplace comedy.
08:14And so once we.
08:15Oh, I didn't know that.
08:16Yeah, it was more set in the nonprofit world initially in my picks.
08:21And Molly was more of a side character.
08:25And they, and she was based on my friend, like she is now.
08:27But, and they really liked that character.
08:29And they were like, well, what if it were more of a two-hander?
08:31And so I was like, oh, okay.
08:33And Lawrence didn't exist in that version.
08:35It was just Daniel.
08:37And that, but they were all playing kind of the background to this workplace element.
08:41The development team was instrumental in making Insecure what it was and being like, let's just, let's do your life.
08:47I didn't realize that at all.
08:48I wonder what that kind of show would have been.
08:51Do you ever think about like what would have happened if you had just kept the show as is?
08:55Yes.
08:55I think it would have just been a black The Office kind of.
08:58Or like a, it would have been completely different.
09:01I still think it would have been funny.
09:03But it just, it wouldn't have, I don't think, resonated in the same way with people who were in their
09:0920s, 30s.
09:10And I'm glad.
09:11I'm grateful for that.
09:12And that's, that was good development.
09:14Yeah.
09:14I was going to ask, you know, because we talk about power.
09:17You handed over a bit of your power when you like go into an HBO sort of situation.
09:21Did you feel that shift?
09:24Like what was that shift like for you?
09:25I don't know that I felt it.
09:26I felt supported because you're, you're grinding super hard.
09:31When you're making stuff online, you're, you're, it's, it's all on you.
09:35It's all on your shoulders.
09:35And for someone to take the brunt of like, this is a, now I'm in a structured process.
09:40And now there are steps.
09:41And these steps are frustrating because someone has the power to tell me whether or not they want to make
09:46my show.
09:47Whether or not my stuff gets to air.
09:49And so in that way, I was beholden to them.
09:51But I was so grateful for the relief of like, I get paid for every step as opposed to bare
09:58knuckling and white knuckling it and just being like, I just need to get here and maybe we'll figure out
10:03the money later.
10:04And so to have like a process and to not have to do everything and to have also to be
10:10able to hire help that wanted to be there and that was being paid to be there, it just changed
10:17the entire dynamic.
10:18And even now when I think about how people are heralding online creators and saying that Hollywood is done, it
10:25is hard to create online.
10:26I know that every online creator, no matter how much money they're making, they're going to want help.
10:31They're going to be like, you know, I would actually rather not do this on my own.
10:35I would rather, that's the luxury, like to be able to be comfortable while making stuff that you love.
10:40Yeah.
10:40I think, I mean, I think it's similar the way we look at print media, publishing media versus a sub
10:45stack or something of that sort.
10:46But just having like that, that sort of structure there is helpful.
10:49So, you know, after Insecure, you've gone on to work on a bunch of projects as an actor, Barbie, American
10:56Fiction, which meant you were a bit of a smaller part of the creative process.
11:02How do you feel?
11:03How did it feel going to someone else's set after running so many of your own?
11:07It's so exciting.
11:08It was cool to like not have all the pressure beyond me, be able to observe other people that I
11:13love and respect and admire, how they run sets, how they talk to actors, how efficient they are, what their
11:20strengths are, and be able to take some of that onto my next projects for a while.
11:25And even now, I'm like, I wanted to be part of more ensemble projects.
11:28That was a goal of mine, just because I kind of just went into it.
11:32You know, I'd never had a TV show before.
11:33And then, you know, I was running one and, or co-running one, I should say, because of, I was
11:38working with Prentice, but it was still like a lot of the decisions were mine.
11:42And I had never been on a professional TV set.
11:44I had never been in a real writer's room before.
11:46Like, to be able to step into that, I think, is incredible.
11:50We talk about imposter syndrome a lot on this podcast.
11:54Lena Waithe said she does not have it.
11:56That doesn't surprise me.
11:58It does not surprise me at all, but it was a moment when I talked to her where I was
12:03like, you know what?
12:04Yeah, hell yeah.
12:06I'm curious for you, when you walked into those rooms, when you walked onto your set, did you experience imposter
12:10syndrome?
12:11I didn't because it was my story.
12:12Once I turned the script into, after so many years of development, that last draft was like, well, fuck it,
12:18I'm going to just write my life.
12:19Like, I'm going to write what I'm going through.
12:21But I had an expertise in what I was writing.
12:23So once they were like, we're making this pilot, I felt like it's only mine to lose.
12:29And even if they don't pick it up, I know that I put everything in it.
12:33And then the other part was like having Prentice, who was a, who had been in several writer's rooms for
12:39a long time.
12:39And he was a first time showrunner and he was so ready.
12:43He was ready to prove himself.
12:45And Melina was the first time TV director and she was ready to prove herself.
12:49So we were all in these positions of like, this got to work for us.
12:52And it was exciting to just be able to create something together.
12:55And though we may have like had creative differences in certain ways, like because we were united in a common
13:01goal of this has to be great.
13:02No, but we didn't have time to think about being like, like, do we belong here?
13:06It was like, we got to, we got to make it so that this exists.
13:08Totally. That's how I felt. I'd never worked at, you know, this is my first time being an editor in
13:13chief.
13:13I've never worked. I've never run a team in this way.
13:16I've never created a print magazine, but I was like, I know what I know and I know what I
13:19like.
13:19So we just got to make the thing and the people will come.
13:22Yeah. I didn't know what a showrunner was until I saw Shonda Rhimes and I was like, oh, a black
13:28woman does this?
13:29Like this is a job and it is a boss.
13:32And that was not something I aspired to.
13:33I was just like, I want to be a writer and I love TV and I want to tell stories
13:37and I want to figure out what that looks like.
13:39I didn't imagine that I would be starring in my own show.
13:41I didn't imagine any of those things until they kind of happen.
13:44And then you're kind of just like, oh, yeah, of course, I'm stepping into this.
13:47So in 2020, you launched your own production company.
13:50Hooray. I'm curious, as a producer, how do you think about the financial versus the creative aspect of a pitch?
13:58I try not to think about the finances I do for a while because I was creating for the Internet.
14:03That was it confined me where I was just like, I got to write this to shoot in my apartment
14:08or I got to write this to shoot in locations that I can get for free.
14:12Now, I think outside of specific genres and like my imagination has kind of been able to breathe because I'm
14:19like, why should I don't have to think about money?
14:21I'm not I'm not making this myself.
14:22So and then when it's picked up, then I'm more cost conscious and I'm like, OK, we're working towards a
14:28goal.
14:29One of the hard lessons I learned initially was through Insecure because I was like, I didn't know again what
14:33a showrunner, what we were responsible for.
14:36We were like over budget for the last couple of seasons and like got pulled into the principal's office and
14:43they were like, yo, what are y'all doing?
14:44And I was like, I don't know.
14:47I don't look at the thing and they were like, no, you actually you guys are over budget.
14:51We got to get it. We got to get it right in tight.
14:53And that was like, well, OK, well, he had told us like we would have we would have worked to
14:58that.
14:58That was also a hard lesson I had to learn on on rap shit of just like because the industry
15:04changed during our production of that show.
15:08They ultimately like if we have been able to produce that for cheaper, we found out on the later end,
15:13then maybe it could have continued.
15:15But like I didn't know that it was expensive.
15:17You know, I didn't know that it was an expensive show to make.
15:20And and so now I'm in that mindset of what can I create to be sustainable?
15:28How can I also work to self-fund it or offset costs in different ways just to make it easier
15:34to produce?
15:35Because every part of Hollywood is cost conscious right now.
15:38I'm curious if somebody was pitching to Hooray, what advice would you give them?
15:43This is twofold. It depends on what medium for TV.
15:45It is just like, how is this the holy unique idea?
15:48And what are you bringing to the table?
15:50And on the film side, what makes something theatrical?
15:53Like what is going to get people to say, I need to go to the movies and go see this,
15:58whether it's with me, whether it's with my girls or my friend group, whether it's with my significant other.
16:04Like what idea do you have that you feel you feel like people are going to be drawn to the
16:08theater?
16:08Because those are the only ways that something will get bought or picked up.
16:11Yeah, that makes sense. I want to talk about your book, your new book.
16:15Yes.
16:15I Should Be Smarter By Now came out just a few weeks ago.
16:18You said I should. Tell us about it.
16:20I wrote my first book like 10 years ago and I was in my early 20s while I was writing
16:25that book.
16:25And every time I see people tag me in it, I'm like, oh, God, that's not me anymore.
16:31And I've been dying to, you know, I was, that was before I was in the industry.
16:35It was post-Awkward Black Girl and I was navigating that.
16:37I think I was at the time got the opportunity to write a comedy for Shonda Rhimes.
16:42So I was working on that pilot.
16:44And since then, obviously, so much has happened and I wanted to have a follow-up.
16:49And in addition to that, I get asked a lot about my journey and from aspiring creatives and entrepreneurs.
16:56And I felt like it was an opportunity to tell the stories of what went wrong, to help other people.
17:03This is a, this is kind of written for people, whereas my first book was written for me and about
17:10me.
17:10So you mentioned in the book that when you started doing comedy tours in college, you were only charging $100.
17:17So this was, for Awkward Black Girl, you asked me how we were making money.
17:21My brilliant producer was like, we should go on a college tour.
17:25We should get, because we had so many audience, I mean, we had so many comments that would be like,
17:29come to our, come to, come to our school, come to Howard.
17:31Come to, and I'm like, what, why would we, how, how are we going to come to Howard?
17:35And she was like, we should do a college tour to promote the show and we can, we can have
17:41them pay for a room and, like, our room and board.
17:44And we'll only, to make it enticing for them, we'll charge them $100.
17:48And I was like, oh, that's great.
17:49That's a great idea.
17:50And it wasn't, everybody booked us.
17:53We booked us.
17:53We booked us $100.
17:55And it was a great way to promote the show.
17:57And it wasn't until, like, Spirit Airlines flight number 35 and staying in the college dorm room of someone where
18:05we were just like, what the fuck is, what have we done?
18:08And then someone pulled us aside of the school and was like, sisters, please.
18:11You didn't hear it from me.
18:13Please.
18:13But y'all got to raise your prices.
18:15And we're like, we just brought a poet out here and we paid them $5,000.
18:18We were like, people are getting paid $5,000 to just speak.
18:22And so.
18:23How'd you choose the number from there?
18:25Like, how'd you learn to set your wages?
18:27And then how has that influenced how you move now?
18:30Once I recognized the toll that it took, like, I was getting sick, the toll that it takes on your
18:34body, the traveling.
18:35We weren't, like, smart about scheduling.
18:38Like, we would be, like, in Dallas one day and then go back to San Francisco and then go to
18:43New York.
18:43And it was just incredibly taxing.
18:46But that conversation really put to mind, like, worth.
18:50And, you know, having grateful to be here energy is something that I have for a very, very long time
18:56where I'm just, like, I'm just happy to be in the room.
18:59I'm happy to be here.
19:00I'm happy people like it.
19:01And.
19:02I want to talk about that for a second.
19:03Yeah.
19:03Because I think that is something that plagues women, that plagues a lot of women of color.
19:09We are told we should just be happy to be in the room.
19:11We put it upon ourselves to just be happy to be in the room.
19:15Of course, I'm happy to be in the room.
19:16Duh, I'm here.
19:17But how did you move past that?
19:20Once I recognize the value where it's like, oh, you're happy for me to be in this room, too.
19:24And I'm adding value.
19:26And you're, in some cases, making money off of me being in this room.
19:31So where's my cut at?
19:32Once I recognize, again, the work that I was putting in.
19:36Now, putting a number to it, that's still something I struggle with.
19:39Having a team has been helpful to set that price because they're, and I talk about this in the book,
19:45there's like a price point for even the HBO deal that I got where I was just like, I would
19:50have never aimed for that.
19:51And that was like, you know, that was a black lawyer who was just like, nah, this is a price
19:56point that I'm setting for you and the standard.
19:59And that was incredibly eye-opening for me.
20:02But it also makes you have to live up to that.
20:04Yeah, I was going to ask about that.
20:06When the number is set, are you nervous when that email goes through and you're like, oh, okay, now what?
20:13Yeah, but I'm also just like, how bad do I want it?
20:17You know, it is hard work.
20:18Yeah.
20:19It is work.
20:20And so if you're saying no to that price point and it's a negotiation from there, then I have to
20:24ask myself, like, how badly do I want this?
20:27How badly do I want to work for this?
20:28And what does that look like for this price point?
20:32It's a constant conversation.
20:33It's definitely something I think a lot of people need to hear.
20:36You've spoken about how you have a good work ethic, which I appreciate as a fellow Capricorn.
20:40You've also said that success in creative industry takes more than just hard work, though.
20:46What advice would you give to somebody trying to make it in a creative industry today?
20:50Trying to make it in a creative industry today.
20:52I mean, I always talk about, again, what you're bringing to the table, standing firm in that.
20:57And that is, like, what your unique perspective is that is elevating any project you take on and being consistent.
21:05Someone that people can rely on is a game changer.
21:09And that's afforded me so many opportunities.
21:12When people know that you're going to show up on time, you're going to do the work, you're going to
21:16be last to stay with them.
21:18Once people recognize that, that goes a long way.
21:21Your reputation is everything, especially in this industry.
21:25And I'm sure you know that.
21:26And people are excited to recommend you when they like, you know, when they like working with you.
21:31So make sure that you're showing up in a way where people will say nice things about you when you're
21:36not here, when you're not in the room.
21:38Because creativity is only one part of it.
21:41There's so many people that I've thought were incredibly creative, incredibly funny, incredibly just dope.
21:48And then met them and was like, oh, I don't want to be around them, though.
21:52They suck.
21:53Like, I'm such a fan of yours, but you suck as a person.
21:58So do I want to be in a writer's room with you?
22:00Do I want to be on set with you for 15 hours?
22:03And so much of being in this industry is just being cool to be around and passing a vibe check.
22:10So just be cool is also what I'd say.
22:13Yeah.
22:13One line that I love from your book was there's so much creativity and brokenness.
22:18What do you mean by that?
22:19Being broke, and this was speaking to it earlier, will make you, will force you to be creative.
22:25Will force you to figure out what you have to make this project or whatever you're working on possible.
22:31Figuring out how to make something for no money.
22:33Like, that is, that's the most creative you're going to get because you don't have resources.
22:37You have to figure out, like, okay, I need this to take place in a space shuttle, but I won't
22:44be able to access one.
22:45So how can I make it look like one?
22:47How can I figure that out?
22:49To make something out of nothing, that is the best feeling in the world.
22:53Yeah.
22:53And you're actually able to succeed and do it, and it works your mind in different ways.
22:57I really love the essay about owning your particular POV.
23:00Can you talk a little bit about that?
23:02Yeah.
23:02It comes down to, like, no one sees the world the way you do.
23:06No one has your eyes, your experiences, and leaning on that is so essential.
23:12But also, that essay came because I was called particular by a colleague.
23:17He was like, you know, we're figuring it out because, you know, you're real particular.
23:21And I was like, what?
23:23What does that mean?
23:23I didn't say it in the moment, but I sat with it, and I was like, what is he talking
23:26about?
23:26Particular.
23:27It felt like such a negative conversation.
23:32And then I, you know, sat with it and was like, yeah, I am particular.
23:36And that means I have a point of view, and I have a vision.
23:38I want things a certain way, and that is kind of my aesthetic.
23:41That is what I bring to the table, and that is my style.
23:44And so, in some ways, that is a compliment.
23:46All the people that I mess with have a particular way of seeing the world.
23:51They have a particular style, and it is uniquely them.
23:55And I wanted to, yeah, own that and stand in it.
23:58I want to talk about the two-part documentary that you have executive produced on HBO called
24:04Seen and Heard.
24:05Yes.
24:05Can you tell us a little bit about it?
24:07Yeah.
24:07Seen and Heard is the most comprehensive history of Black television you will ever see.
24:12It came from, you know, we started this in 2019, and that was like such a boom.
24:17The before times.
24:18The before times.
24:19It really does.
24:21When I saw that, I was like, 2019?
24:23Yeah.
24:23Whoa.
24:24Yeah.
24:25And that was when it felt like we were in this renaissance of Black TV, of art, all these
24:30other things.
24:31And we didn't know it at the time.
24:33Obviously, the pandemic hit, and then all of that went away.
24:36But I wanted to explore the different periods of Black television that have influenced today,
24:42that led to this point.
24:43It's part history, part inspiration.
24:46It's just dope as hell.
24:48How has the representation of Black people evolved in media over the years?
24:53Like, where do you think we were?
24:54And where do you think we are right now?
24:57I think it's circuitous.
24:58I think that we've gone in these cycles.
25:00But when I think about our history, sometimes we've gone from, like, props to the beacon.
25:07And I think the next step is ownership.
25:11Because when we talk about these waves of Black influence, like, there's no doubt that
25:18we create culture, and that we set a standard, and we set a bar.
25:22And then that's almost taken from us.
25:24We were just talking about how, like, a lot of these networks started with trying to attract
25:29a Black audience because we are the most loyal at the end of the day.
25:33And we watch everything.
25:34We watch stuff that doesn't feature us.
25:36We watch stuff that features us loyally and fiercely.
25:39And we have a lot of spending power.
25:43Like, we're ideal customers.
25:44And so, so many networks like Fox and UPN slash WB, they've all built their audiences on
25:51Black viewers.
25:51And then once they were successful, moved to broaden the audience.
25:57Now that Hollywood is kind of trying to understand its place and work within, like, these YouTube
26:04creators and that model and compete there, they're open to different formats.
26:10And so this is a time to kind of plant our flag and just be like, this is the move
26:15towards
26:16ownership moving forward.
26:18I was watching, I believe, CBS Morning, and you said that you're confident that we can get
26:23through this time of a lack of representation in media.
26:27How?
26:28These kind of times when it's trying, it breeds innovation.
26:31Like, this is the time when we're, again, the most creative, when our backs are against
26:34the wall, when everybody's struggling at the same time, when there is no norm, when the
26:38rug has been pulled, when there's no foundation, it's just like, oh, now this is the time to
26:43create foundations.
26:44And we're all in the same boat.
26:45Everybody is struggling out here and trying to figure it out.
26:49So it's new to us because nobody knows what, like, AI, where AI is going to lead us.
26:54And I don't know that in America, we've also ever had billionaires literally dictating and
27:00running our culture that we could just plainly name.
27:03What we create, where we create, like, they're dictating so much of our lives.
27:07That's not being offset in any way.
27:09And that only means that some sort of rebellion is coming, but I don't know to what level.
27:14But yeah.
27:15Yeah, like, I'm not on the front lines planning it or anything, but like, I would assume.
27:20I would assume somebody out there doing something.
27:23But that's a good point, too, because I feel like we talk about a lack of leaders and I always
27:27talk about, like, we know who all the supervillains are, but who are, where are the superheroes
27:31at?
27:32Yeah, who are, we're, please, fly in.
27:35Please.
27:36Something I really like that you said in the doc was we need our own shit.
27:40Like, we really, really need our own shit.
27:42First of all, I like that you said it so plainly.
27:44Second of all, it is incredibly true.
27:46For those who are listening, though, that are like, yes, we do.
27:50Now, how do I do that?
27:51One of the things that was essential for me was, like, understanding what the tradeoff
27:57was, you know?
27:58I didn't want Awkward Black Girl to go to TV.
28:00There were offers to make that possible, but I knew what I would be giving up in return.
28:06And so you have to be comfortable being uncomfortable for a very long time and having the faith to
28:13just be like, I know that I can hold out because, like, I own that shit at the end of
28:19the day.
28:20I own, you know, Awkward Black Girl at the end of the day because I held out.
28:24But I don't own Insecure.
28:25I don't own these other things.
28:27And, but now that is a goal for me.
28:30And so the advice is literally just trying to find the group of people that I can build
28:34it with.
28:35It's, it's so hard.
28:36It's also easier said than done.
28:38It's something I recognize because you have to have your kind of eye on the prize.
28:41What I really loved about your career path, though, is that in addition to the many, many
28:46things that you do in entertainment, you are the founder of Radio, a music company,
28:51Via Ray, a wine company, Sienna Naturals, a hair company.
28:55You've opened two restaurants, right?
28:57Somerville, Downtown Doe.
28:59We have Hilltop as well.
29:01Hilltop, a coffee shop.
29:02That is so many things.
29:04It's like what I was, like, the list is so impressive.
29:08I really want to talk to you about balance.
29:10What is work-life balance?
29:12What does that look like for you?
29:13Or is it like work-life seesaw, as one of my friends put it, and you just try not to
29:17fall off the seesaw at any given time.
29:20You know, you list all that and I have partners in all of those things.
29:23And a lot of, a lot of what I do involves collaboration.
29:27And I've had to learn delegation.
29:30I love to work, but I love to rest.
29:32Like, don't get it twisted.
29:32I love to play.
29:33I love to do all those things.
29:34But working is my personality, unfortunately.
29:38And I feel like a lot of my self-worth comes from it.
29:41And I don't feel worthy unless I'm productive.
29:43And that is a very sad thing.
29:46But I don't mind.
29:47Is that something you're trying to change?
29:48Or are you cool with that?
29:49I don't want to do it forever.
29:50And when I finally took a break, I took a month-long break after Insecure.
29:55And that was hard.
29:56I had to tell other people that I was going to do it.
29:59Because they also assumed, like, you always say you're going to do something.
30:02But you don't.
30:03Like, I just got married.
30:05I had ended the show.
30:07We had just finished the first season of Rap Shit.
30:10And I was like, I was done.
30:12And I had to convince myself to take that time off.
30:16And when I did, I was like, why don't I do this?
30:19I felt so much better on the other side of it.
30:21And then I felt ready to go.
30:22I was just burning out for, like, you know, 10 to 15 years without really taking any time.
30:27And that is unhealthy.
30:28And so I recognize what rest does for me.
30:32But I also recognize that I haven't, because I don't have kids yet, I haven't had a reason to stop.
30:38That's another part of life that I'm more interested in now.
30:41And I'm like, okay, maybe that's what will slow me down and cause me to rest.
30:46But otherwise, I'm going to keep going, because I get to be very selfish during this time.
30:50I want to wrap up our conversation here by talking about style, another big sort of tentpole here.
30:55You know, you were about to hit the road for a multi-stop book tour.
30:59When you're approaching getting dressed for that, what does that look like?
31:01Because this is a book tour, and it's so much about me, I just want to feel my best self.
31:06And I found myself, especially, like, in this new age, in this new decade, I'm one of those people that
31:13I always feel like I have to save my fits for my best, my time.
31:18And I'm just like, why am I doing this?
31:20Like, not to be morbid, but I'm like, time is running out, so I got to get these off.
31:26And so part of it is, like, I want to show up as my best self.
31:29I want to be, like, in my fine 40s there.
31:32So comfortably chic is my approach on this tour.
31:36Yeah.
31:36Are there any brands that you're loving these days?
31:38No, I'm not, like, a big brand girl.
31:41I'm just, like, a what looks great on me, what fits me.
31:44What's your approach for red carpet dressing?
31:46Because that feels, like, markedly different from what you would do on a book tour.
31:51Yeah.
31:51I mean, I work with an incredible stylist, Worry, and...
31:55Worry Vice.
31:56Worry Vice, yes.
31:56Oh, I love Worry.
31:57Yeah, he is the best.
31:59And we go back and forth.
32:00Like, how, yeah, how I want to show up.
32:02If I feel, if I feel like I am, like, that I feel like a knight should be about me,
32:09then
32:09I want to show up and have, you know, more statement pieces.
32:13But if I want to just kind of show up and be elegant, it's all mood-based for me.
32:19I have periods where I just know that I want to be, I want to look back and feel like
32:24I
32:25was showing up as my full confidence of, like, in any room I want to walk in, I want to
32:29feel
32:29like I'm boldly elegant and confident and fun.
32:34And that's kind of what I am for.
32:35I think elegant is one of the best compliments you could give.
32:38Yes.
32:38People always say that about my mom, and I think that's hilarious.
32:42They always think that she's, like, refined and elegant.
32:44And she is the goofiest person on earth.
32:46Like, I have to argue with someone and be like, no, my mom is actually goofy.
32:49And they're like, no, there's no way.
32:50And I think there's a way that you can, like, deceive people.
32:53As someone who's always felt awkward and uncomfortable, you can present so much differently with style.
32:58And I lean on that.
32:59Let's talk about hair and beauty for a second.
33:02Your hair is incredible today.
33:04What's your approach when it comes to your hair on the red carpet or on book tours or that
33:08sort of thing?
33:09Same.
33:09Like, again, I work with an incredible team.
33:11And there, like, I tend to just be a canvas in some ways.
33:16I know what I like.
33:18And I know what I feel like looks good on me.
33:21And I'm vocal.
33:22But I generally, like, it goes down to collaboration where I'm like, okay, if I'm a canvas, what
33:28y'all got?
33:28What y'all creating?
33:29There have been moments where, you know, we call them glam slams.
33:33And then there are moments where it's like, were y'all talking today?
33:35What happened?
33:36You just wanted to do your thing.
33:38Oh, okay, cool.
33:38Got it.
33:39Okay.
33:39But I'd be remiss if I didn't ask about the skincare routine.
33:42You have some of the best skin in Hollywood.
33:45Please tell me.
33:45I feel like I just mastered my skincare routine.
33:49But I swear by Deutopia.
33:51It's like a nighttime acid.
33:52And it's like, it's like an exfoliation of the face.
33:56You know, when I think about just being raw and barefaced and then coming back home, there's
34:01nothing better than just the cleaning of skin.
34:05And that helps me to feel like I wake up with exfoliated skin in the morning.
34:09So before I let you go, we always like to end this podcast with three questions about
34:14money, style, and power.
34:16Rapid fire questions.
34:18Number one, first question is, what's one thing money can't buy?
34:22Money can't buy respect.
34:24Lame is lame.
34:26Ah, screaming.
34:27And very true.
34:28Please.
34:29Extremely true.
34:30If you could trade closets with anyone, who would it be and why?
34:34Tracey Ellis Ross.
34:35I just feel like she's so fun.
34:38And she has vintage pieces.
34:41And she just loves that.
34:42When I think about someone who has so much fun with fashion, it's her.
34:46Lastly, what's your go-to song when you want to feel powerful?
34:50Right now, it is, I'm that girl.
34:52Anytime I hear Beyonce, which, well, please motherfuckers ain't stopping me.
34:56Anytime I hear that, I get amped.
34:59Yeah.
35:00Well, Issa Rae, thank you so much for joining us on Nice Talks.
35:04I had to pee this whole time.
35:05Oh, my gosh.
35:05I'm so sorry.
35:07I'm so sorry.
35:08I'm so sorry.
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