Underneath the actress’ insecure comic persona lies the fearless heart of a serial entrepreneur. She has parlayed a film and television career into a jewelry collection, a haircare company, a Prosecco brand—and counting. A portrait of a modern renaissance woman.
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LifestyleTranscript
00:00Issa Rae, thank you so much for coming to the Forbes Power Women Summit.
00:03My pleasure.
00:04Thanks for having me.
00:05It's especially an honor because 10 years ago, in 2014, you were on our 30 Under 30
00:12list.
00:13And in those 10 years, a lot has happened.
00:14A quick summary.
00:16You became a best-selling author, you founded your own production company, you are a Peabody
00:21Trailblazer Award winner, and this fall you are launching a new jewelry line, a lot of
00:28which you are wearing right now.
00:30Indeed.
00:31That's a lot of titles, and I left a few off.
00:33Do you have a favorite role that you play or hat that you wear?
00:37Oh, I mean, hands down, being a producer, a writer-producer.
00:41Like I love being able to, I put that combo together because I love being able to like
00:45pin something and then make it.
00:49And that's, like nothing's more satisfying than that.
00:52You're a big handwritten note.
00:54I'm a handwritten girl.
00:55Like, I see your notebook in hand, like I need a notebook.
00:59And if I have an idea at night, I will reluctantly write it on my phone because, you know, it's
01:06hard to like be in the dark and try to write something down, but that's like the only time
01:10if my notebook's not handy.
01:12You say writer and producer, I would say storyteller.
01:16That's a better way to put it.
01:17But the storyteller still omits the making of it part.
01:23It's almost a little bit like storytelling is just a part of it, but like to actually
01:28physically produce something feels like, I don't know, powerful.
01:34Let's talk about making things and also how it's changed because you really got your start
01:39with a YouTube channel and now you have your own production company.
01:43You've produced for HBO.
01:45How do you feel like the industry and the business of storytelling has changed?
01:50It's just become, I mean, it's become more democratized.
01:53There's so many more ways to tell stories.
01:55There's so many different platforms.
01:57There are like even where length is concerned, like that was a big thing when I was coming
02:02up.
02:03It was just, I thought that people would only take shows or stories seriously if it fit
02:12within this specific model of like 30 minutes for a show, hour for a drama, an hour 30 for
02:19a movie.
02:20So it's just kind of time constraints.
02:24And in producing what I hoped for the web, people would receive as a TV show, I thought,
02:31you know, the longer the better.
02:33But initially at that time, it was about just more short form content and getting people's
02:37attention.
02:38And over time, people craved, you know, longer work for me, but it's so important now.
02:44Obviously there are things like, I mean, Vine has been gone for a long time and now there's
02:48TikTok and people will just, people will watch anything as long as it entertains them.
02:54And they will continuously watch it if it feels tailored to them.
02:57And so, so much of what I feel like the industry at large is going after is kind of chasing
03:05people's, what people think they want to see on television or film.
03:12Chasing what people think they want to see.
03:14Chasing what people think they want to see, yes.
03:16And I say that in the sense that I think on the negative side, it's, it avoids risk because
03:24you're kind of tapping into people's comfort zones is what I'm getting at.
03:28Like whether it's nostalgia, whether it's sequels, whether it's whatever it is, like
03:33this is what we think people think they want to see as opposed to this is what, this is
03:41what we want to see.
03:42And this is what, we're going to set this trend and we're going to, we're going to ensure
03:48that we're giving this particular filmmaker a chance, this particular writer a chance
03:55because they're visionary.
03:57And when I think about a movie like Beetlejuice, like the sequel just came out, but the original
04:01is so weird.
04:03It's Tim Burton.
04:05It's kooky.
04:06And a movie like that came out in the 80s and made a huge impression because it was
04:11unique.
04:12There weren't any other stories like that.
04:14And I don't know that there are a lot of films like that that are possible today because
04:22the fear of taking risks and really being a little too tuned into what, what audiences
04:29may want.
04:31Do you feel like your production company allows you to take risks and was that part of the
04:35thesis in starting it?
04:36Yeah, absolutely.
04:38We, one, want to prioritize like black audiences and storytellers.
04:43And those stories in particular are what, are the reason why I'm here and just seeing
04:48that it was possible.
04:50And we're also in a business.
04:54So we also have to think smart and think about, you know, obviously what will, what will make
04:58money, what will draw audiences to our work, but we are very much like what is missing
05:04first?
05:05What voids can we fill?
05:09On the story side, on the brand side, whatever, it's like, that's the central question is
05:13just like, what's not out there yet?
05:14What hasn't been told?
05:15What's new?
05:17What is not out there?
05:18And how are you bringing it forward?
05:19Because you also have a marketing arm.
05:21You have a lot of different lines of business that all kind of coalesce in helping get these
05:26stories to the public.
05:27Yeah, there's a, I mean, the flywheel effect that for me, it's, it is about an ecosystem
05:32and that's also how I decide what I want to take on next.
05:36Is it feeding the next thing?
05:38Does it make sense?
05:39Without giving away state secrets or things that are under NDA, when you're sourcing stories
05:44or when you're looking for new storytellers, who is not getting attention that you think
05:47you're finding?
05:48Oh, well now I've just seen a pivot away where, where initially I would say in like the, around
06:002016.
06:02You know, there was an, and even in 2020, post 2020, there was more of an effort to
06:06like find diverse voices of color and give people chances.
06:15And that's not a priority anymore, but it still is for us.
06:19So we are just mining, in addition to like new voices, we're mining people who have gotten
06:27a shot in the past and maybe didn't do well theatrically or didn't get the ratings television
06:33wise that like Hollywood has kind of discarded to just say, Hey, do you want another chance
06:38with us?
06:39And I guess that's the most specific I can get without naming names.
06:43That's fair.
06:44I know, I know you made some comments earlier this year to Time Magazine about, I've never
06:49seen Hollywood this scared and clueless and at the mercy of Wall Street.
06:54You've gotten a lot of attention for these comments.
06:56What does that mean?
06:57And were you surprised at the reaction you received?
07:01I wasn't surprised at the reaction.
07:03I think I would have, no, I still stand by like the idea of, the idea of Hollywood being
07:11scared.
07:12Absolutely.
07:13Cause there's just, the market has changed so much and they're at the mercy of the market.
07:19And it just really meant like there's, it's hard to have original ideas.
07:24Like a study just came out that only like 10% of movies are original at this time.
07:30And that's, that's crazy for a business that's like built on creativity.
07:34That's a scary thing.
07:36If you know you're prioritizing IP or prioritizing these sequel moments, like that's, that's
07:43great.
07:44That's a great side of the business, but the originality is what got people excited to
07:48be in the business in the first place.
07:51It's amazing that the money, that the pocketbooks forget that, because I think about the stories
07:55that I've been attracted to and eventually when there are so many sequels, even for a
07:58franchise I love, I tune out and it feels penny-wise and pound-foolish perhaps?
08:06Yeah, I guess that's why these other platforms are taking off the way that they are.
08:12You know, that's why YouTube is the most watched platform, you know, here.
08:19That's why TikTok is having the, the, the craze that it is now, just because these are,
08:27they're free for the most part.
08:29And this next generation is dictating kind of what they want to see in their preferences.
08:34And in that way, like I always lament that there's not a monoculture in the same way
08:39and that, that I do miss.
08:42And I wish that there was a way to, outside of film and these tentpole moments, to bring that back.
08:52I think we're missing that.
08:53We see that with the Olympics and some of what's happened this year with sports.
08:55The Olympics were so refreshing to just be able to, to, one, of course, the Olympics
09:00themselves, like to watch people be the best, but then to like have the unity around rooting
09:06for people, the objective truth of just athleticism.
09:10Like we were all on the same page of just like, you can't deny that someone got first place.
09:15We're just all on the same page there.
09:17And we don't have that, yeah, outside of these sporting moments.
09:22Now, you got your start with YouTube.
09:24I'm wondering, what have you observed about the cycle of YouTube?
09:27Because it was this vehicle of opportunity in 2010, 2011 for you.
09:32You get on the 30 Under 30 2014, and then it's now the most watched platform.
09:38How does that journey feel to you as a creative?
09:41Do you wish you had done more with YouTube in the interim?
09:44It feels about right.
09:45Like I definitely saw that YouTube was going to be the platform where people were going to watch things.
09:49I think where things changed was the monetization of it.
09:53And I was never, I was never like a YouTuber.
09:56I still think I was a storyteller.
09:58I wanted to tell stories in a very specific way.
10:00And my gateway or my pipeline was like television and film.
10:06Like that's where I ultimately wanted to be.
10:09But the monetization aspect changed it in a way that, you know, you could have these
10:14popular vloggers, you could have more attention seeking content.
10:20And like it became more about views.
10:22And we were never like, we weren't the most viewed web series ever.
10:27And I think that's not necessarily my, my forte of just garnering views at all costs
10:33or being a personality in a way.
10:36But where like, I do feel like I missed out is making kids content.
10:39Like that is, when I think about all these kids are watching YouTube, that's what they're
10:44begging their parents to watch.
10:46And then what I used to watch as a child, that is like a missed opportunity for me.
10:51So I have slight regrets.
10:54If you were starting now, with the YouTube landscape being what it is, do you think you
10:58would have been as successful as you were back then?
11:01Ooh, no, I think I would have been too intimidated.
11:03And because I wasn't, at that time, I was like, nobody's doing this, nobody, especially
11:08not for us.
11:09No one is telling short stories or making series online in this way on YouTube.
11:15And I felt like the story was, you know, wholeheartedly unique in so many ways.
11:21So I think if, yeah, if I were dropping in now, I don't know that YouTube would be my
11:25platform.
11:26I feel like it would be a TikTok.
11:27Interesting.
11:28I know.
11:29I know.
11:30Well, it's launched a lot, so I understand where you're coming from.
11:34But to that point, the platforms are both an opportunity, but do you see them as a challenge?
11:38Because I've heard investors say, if you pull a room of 200 people, everyone's watching
11:4310 shows, and there might be overlap of maybe 10%.
11:45To your point, there's no monoculture anymore.
11:48So is the proliferation of shows and platform more of a challenge for someone like you,
11:53or is it an opportunity?
11:55It's a challenge at this very moment, only because there is so much.
12:03I will say, no, and I actually take that back.
12:05It was a challenge pre-Strike.
12:08And now that studios have pulled back, I think the only, I guess, benefit is that they're
12:15producing less shows, and inevitably, if there's half less of what there was, then
12:23there is an opportunity to have overlap in terms of what we're watching.
12:28And there's a lot of merging and consolidation happening, and so you're not going to have
12:33that many platforms, and that's not great for writers, showrunners, because it means
12:38there are less places to pitch.
12:40But as far as the culture is concerned, it's like when there were only five TV networks
12:46at a time.
12:48So I'm very curious to see how that does bring monoculture back in some way.
12:54You mentioned the Strike, and it was around this time last year that writers and actors
12:58were still on Strike.
13:00Are you feeling the effects of the aftermath today, September 2024?
13:05Yeah, absolutely.
13:06Just living in L.A. and seeing that there are not a lot of productions there.
13:11We just shot a movie, and it was rare.
13:13We got to shoot in L.A.
13:14We got to shoot in our neighborhood, but when we were on stages, there weren't any other
13:20shows or movies shooting alongside us, and I've never seen that before.
13:25It's always such a battle to get stages, and yeah, I've seen emails from people reaching
13:35out to see if there are opportunities.
13:39It's kind of dark out here.
13:41People are moving back to where they may have grown up or their hometowns because there
13:46just aren't many opportunities and not a lot of shows shooting, and then everything's mostly
13:51shooting overseas, so it's pretty dark right now.
13:55Interesting.
13:56I was going to ask, is it the dampening effect of not having activity during the Strike,
14:01or is it something in the contract that's dampening the interest and ability for productions
14:07to move forward?
14:09Things are more costly, obviously.
14:11Writers, actors, and crews negotiated for more money than they deserve, frankly, and
14:18so studios are like, okay, we'll bet.
14:20We can't produce as much as we could because everything's more expensive, and it's more
14:23costly to shoot in the States, so we can kind of get around some of these contracts overseas.
14:30But it sounds like Hooray, your production company, you said you were just filming, so
14:34you're finding the opportunity in this market.
14:36Yeah, but honestly, that was a movie that was like seven years in the making, which
14:41we are so excited to be able to shoot.
14:42It was with the Sony program, and it went to TriStar, and I think everyone on board
14:48is just like, whew, can't believe we're here, and that was very much the energy on set,
14:53just feeling grateful that we were able to make this happen.
14:57I'm a new director, a first-time feature writer.
15:01We were able to make that happen, but that won't happen again unless it's successful.
15:07So right now, we're very much in a place where we have to make sure that it's successful
15:13or else we won't get those same opportunities again.
15:16You talk about the flywheel, the businesses that you have.
15:19If you look back to when you were starting, did you imagine having an entrepreneurial
15:23empire with, there's indie music in there, I think I mentioned marketing, and feel free
15:27to fill in the gaps, but was that always the goal, or did that kind of happen organically?
15:32It happened organically, and it happened because these were things that we were already doing,
15:38and so for me, it was just about formalizing it and building intention around it, building
15:44people who were professionals around it.
15:46Those things came my way, like when I think about Insecure, I was heavily involved in
15:50the music supervision, and with some of the other shows that we were producing, the same
15:55thing, and so formalizing and having a music supervision company within this label that
16:03we've created, Radio, felt like an organic move, and that's kind of how I approach everything.
16:09With our marketing arm, people would come to me for brand campaigns and the like, and
16:15they would heavily tap into me and who I was and my way of telling stories, so I'm
16:21like, well, why is this agency, like what are they doing then, you know, and so it was
16:27more of, again, formalizing that and putting the team members in place to make it so that
16:32we can do that on our own.
16:34Formalizing it, and you've also done something interesting with the naming of a lot of these
16:37companies.
16:38Can you explain how you've named some of these entities?
16:42Sure, I mean, I'm named after my mom's sister, Rae, and I've just made sure to include that
16:53in everything.
16:54Hooray was actually her, she spelled it differently, but she was a visual artist, and she started
17:01a non-profit organization highlighting other black visual artists in the Bay Area, and
17:05so she used to call it Hooray for the Arts, and as a young girl, I was like, that's so
17:10funny because that's her name, and so I think I've taken that on, she loved to be corny
17:17about puns with her name, so I took that on, and there's Radio, there's Hooray, there's
17:22V-Ray, which is Prosecco, but I think, and then there's Brave, which is the Brave collection
17:30on the jewelry line, but I think that's it, I'm not doing it again.
17:33I was going to say, it's good branding, and it perhaps conveys ownership in some ways.
17:38Sure, yeah, but in so many ways, I do want my brands to live outside of me, and initially
17:44my production company was called Issa Rae Productions, and for me, that does feel limiting,
17:49it feels like people are going to expect either me, or whether it's my sense of humor, or
17:57my particular taste, and if I want this to live beyond me, I think people, Hooray is
18:02just a celebration, and while it has my name in punny form, it could still live beyond
18:07me without just being tied and limited to me.
18:11How do you split your time among all these businesses, and ensure each is getting appropriate
18:17time, attention, and strategy when you have so much going on?
18:20Honestly, it's a lot of conversations, a lot of meetings, and I don't claim to do that
18:27well or effectively as much as I want to, and so it's constant, managing my time, checking
18:32in, especially as the company is growing, corporate consulting help, because this is
18:38a world also that I didn't get to live or work in for a long time, I worked in non-profit
18:44environments and corporate environments, but to run a company is entirely different, and
18:49it feels like I've been, to your point, all these things have happened organically, the
18:54door has been opened, but maintaining it is a whole different story, so it's something
18:58I'm continuously learning.
19:00So let's talk about Brave, spelled B-R-A-E-V-E, just for folks at home who don't have the
19:05subtitles on, how did you come to start your own jewelry collection?
19:10You know, I didn't know that it was possible.
19:13For me, it was about, as I shop, I love statement pieces, I love to create, I'm sorry, I love
19:24to wear pieces that reflect me that I also don't have to take off, and when I look back
19:31at even my own foray into this industry, there was a part of me that didn't feel like I was
19:42glamorous enough or belonged because I was very simplistic, and to invest in jewelry
19:48is such a, that's such a milestone, that's such a marker, it's a status symbol in so
19:53many ways, at least in my mind, you know?
19:58And so, in showing up in these rooms, if it wasn't going to be my clothes, it was going
20:03to be my jewelry that made me stand out, that made me feel like, oh, I belong in these rooms,
20:07I belong in these spaces, and also being an introvert, there's not, you're constantly
20:15drained and questioning your place in these rooms, and for me, jewelry felt like kind
20:22of my armor in terms of belonging there, like, oh, I put these earrings on, I'm rocking
20:28these rings, I have my necklace, I feel like this is me, glamorously belonging here, at
20:33least, and representing on the outside how I don't necessarily feel on the inside.
20:38And sometimes the outside can lead to the inside catching up, but.
20:42Absolutely.
20:43Talk to me about what you're wearing right now, because you have a few, I'm looking at
20:46your hands, I'm looking at your wrists, you have a few pieces from the collection, and
20:50can you talk about how you partnered, not just partnered, but invested in the company
20:54that's bringing this collection to life?
20:56Yeah, so it's a collaboration with Cass Jewelry, and I'm wearing a couple of the pieces now,
21:00the bracelets, and my favorite, the flip pendant necklace, which is, you know, as a creative,
21:07and I always fidget with my jewelry anyway, and this allows you to actually flip to the
21:13other side, and I use it as a mood ring, as you know.
21:19And if it's on black, it's like, don't mess with me, I don't want to be talked to, but
21:23it was on gold, as you pointed out, which is why we're talking right now.
21:26I'll be free to put it back.
21:28Is it on gold again?
21:30Great.
21:31We're good.
21:32Yes.
21:33We're good.
21:34We can keep going.
21:35But yeah, the collaboration was really seamless, I wore Cass Jewelry in the past at award shows,
21:43and when I met with the company, that's when I was really impressed, because Rachel has
21:47such a clear vision about the storytelling behind the jewelry for her, where it is traditionally,
21:56like the way that jewelry has been advertised is just as kind of women waiting for men to
22:01gift them these pieces.
22:05And for her, it was about like, no, we love to buy jewelry for ourselves, it might represent
22:12a milestone, it might represent a level up, but that I hadn't heard of jewelry being spoken
22:21about in that way.
22:22And so as a storyteller myself, I thought about my own moments and my own relationship
22:27with jewelry, and it felt so aligned, and to be actively involved in the process of
22:32creating jewelry and learning so much more about it, in addition to working with a company
22:37that's sustainable, woman-led, and our aesthetics match, it was just, you know, it was a perfect match.
22:44Have you learned anything about storytelling by delving into the artistry of jewelry?
22:48It's obviously very different than the other mediums that you've worked in, but in terms
22:51of either reaching audiences, or the way you shape a story?
22:54We'll find out, honestly, because we're just kind of approaching it from the way that I
22:59would want to be, I guess, marketed to, the way that I would want, like what my relationship
23:04with jewelry is, and whether that is effective or not, we'll see.
23:09I bring humor to almost everything that I do, and most jewelry advertisements don't,
23:16it's very sexy, it's very, I was going to say demure, I hate that word, but it's very,
23:24you know, it's elegant, and we have all those things as well, but there's also just the
23:29human element of just kind of investing in who you want to be.
23:34We've talked about a lot of your business activity, what's next?
23:38And if you say a break, I think I'd understand.
23:40I just took a break, I just had a wonderful vacation, but what's next, we have, I mentioned
23:48this movie that I'm really excited about, starring SZA and Keke Palmer, that hopefully
23:54will be coming out next year, and then, be it rain, my Prosecco has a rose, a Prosecco
24:01Rose, coming out that I'm super excited about, and yeah, about, there's a couple television
24:09projects that I'm working on that hopefully I'll be able to talk about soon, but I'm very,
24:16very excited about returning to that medium.
24:19And another business is a haircare line, tell us about that.
24:22Yeah, Sienna Naturals, we just got on Sephora.com, so you can find our products there, and we're
24:29hoping to be in Sephora stores next year.
24:32What specifically are the products, is it shampoo, is it conditioner?
24:36It's everything, it's haircare, it's scalp care, we're not in the styling product space
24:41just yet, but that's another ambition for next year too, but shampoo, conditioner, scalp
24:47oil, a curl cream, you know, I kind of invented, but yeah, there's anything that takes care
24:52of your hair and your scalp, we make.
24:55You kind of invented, so hold on, I feel like there's a story there, how many chemists
24:59did you talk to, or what was that process?
25:01It's still directly through Hannah, who's my co-founder, and she, I just essentially
25:09begged her, I was like, can we make a curl cream, because there's a specific type for
25:13my hair that I need, and it's not, I can't find the right product, especially any that
25:19are actually clean, and healthy for my hair, and so she was like, say less, and so I tested,
25:28I kid you not, about 12 different formulas, she would always send them, like the chemist
25:33did this, what more, and I was like, can you make it thicker, this one feels a little bit,
25:39it's not really defining my curls, so I felt like I had a hand in it, did I mix it myself,
25:44no, shout out to the chemist, but I made it.
25:48I like that.
25:49I also have another question, to your comment about Hollywood being at the mercy of Wall
25:54Street, you're speaking at the Forbes Power Women's Summit today, there are people who
25:57work on Wall Street who are either investors in entertainment, or aspiring investors, what's
26:02your message to them, what do you want them to do?
26:05That's so interesting, I don't know what I could say to, you know, it is so industry
26:14focused, my message is really only to executives, honestly, not even executives, but like, yeah,
26:22the C-suite, because they're the ones prioritizing that, and there has to be a recognition that
26:26at some point that's going to harm the creativity.
26:29If they're not investing in the diverse stories that need to be told, or at least in your
26:33view need to be told, you know, what do they need to hear in order to get there?
26:38I think creating mandates, but again, it's so complicated when there's, you know, art
26:44has typically been so subjective, and it's an art form, and now, because these studios
26:50are so closely tied, just by nature of mergers, and consolidation to the expectations of Wall
26:58Street, like, we're at this kind of impasse of just, it has to reach the most people possible
27:05and be extremely successful so that we can get our money back, but at the same time,
27:12there's so much joy and risk, and I think investors, so much of the thrill is like,
27:16I want to invest in something that will, you know, change the world, or obviously make
27:22a huge return on my investment, but there has to be a consideration that art, art has
27:28the power to do that when it has room to breathe, but again, it's so complicated when, I guess
27:35capitalism or making money is the priority.
27:39One or two more questions. We have a lot of aspiring entrepreneurs, aspiring filmmakers
27:43who watch these videos and read Forbes. If you were to go back and give your under-30
27:49self some advice, what would you tell younger Issa?
27:54Ooh, stop comparing your journey to others. I used to read Forbes and other magazines
28:01all the time, and the Forbes 30 under 30 list changed so much for me because it was
28:09such a validation, and I didn't think I deserved it. I was like, I only have this one thing,
28:15and it was just like, I was comparing myself to other people my age who were doing so much
28:20more, even, I mean, through the pages, like, dang, they're on the list too, and so why
28:24am I on here? Like, the imposter syndrome of it, but to stop comparing my journey to
28:28others and just focus on what you're doing and continue to do it well.
28:34Continue to do it well. That's great advice. Issa Rae, thank you so much for being here.
28:36We so appreciate your time.
28:37Thank you. Thanks for having me.