Issa Rae | Writer, Producer & Director

Just inside Issa Rae’s front door sit two full suitcases waiting to be unpacked. Having just flown in the night before, Issa seems as happy to be home as I am to finally meet her. Curled up on her green couch, with a bag of Oreos open between us, she shares how excited she is not to be traveling for the next couple months — a luxury she isn’t taking for granted. As a writer, producer and director of her own web series, Issa’s schedule gives her few chances to catch her breath before she is off to the next thing.

While still a student at Stanford University, Issa joined YouTube in 2007 because of her love of storytelling. Her YouTube career officially took off after her award-winning series “The Misadventures of Awkward Black Girl” was picked up by Pharrell William’s network I am Other. In her past six years on YouTube, Issa has created numerous web series including “The ‘F’ Word,” “Let Leslie Tell It,” “Roomieloverfriends,” “How Men Become Dogs” and “Ratchetpiece Theatre.” She is the CEO and owner of her own production company and remains passionate about creating content that breaks the stereotypes restricting the black community in traditional media.

And despite having a mantel place full of awards including Forbes 30 under 30 and Root’s 100 Most Influential People, Issa seems more comfortable talking about the internet’s latest meme of Miguel trampling a girl’s neck rather than bragging about her personal successes. Sitting down with NMR, Issa shared with us her approach to dealing with racist comments, what she would take with her if her house was on fire and why she is so passionate about making content for an audience of color.


For interview in video format, please go to last page.

When and why did you first start your production company?

Issa Rae: I initially wasn’t thinking long term at all. I knew that when I started making web series, and I wanted to– actually when I started making web series it started out of boredom and wanting to get by work out there. I was constantly on Facebook and addicted and felt like I should find a way to make it productive, and I came up with the idea to do a soap opera of what it’s like to be black at Stanford. It was like mockumentary style and it started spreading, and I was like, “Oh my gosh, this is a great medium, and maybe I could use this show and show the response to it and turn it into a television show,” and that didn’t work out, but for my second series I was like, “I’m going to make this like a TV show in that I’m going to put it out every week at the same time, and we’re going to promote the hell out of it week after week and then hopefully I’ll get television’s attention.” It was always with the goal of getting television’s attention, and it wasn’t until with “Awkward Black Girl” I was like, “Eff it. I know that no one is going to go with this idea. I’m just going to put it out for the web and have that audience and my friends and family appreciate it and see what happens,” and of course that is the one that really catapulted me in terms of digital success. Now I’m thinking long term where I want to produce content, more content, and I want to showcase more people of color in terms of stories and actors on the web, so that’s my goal now.

Has it always been a priority for you to portray people of color in your series?

Definitely, because we’re not really represented anywhere else, and I know that personally I like to see myself represented and I know a lot of my friends do as well, and I think that it’s not hard to do at all, so it’s like if we’re not having it on television and film then put it on the web. That’s always been important to me; that’s always going to be important to me until I see some sort of change.

When you originally began making your web series, you took time off from Stanford to go to film school. Why was that important for you to do?

I took time away from Stanford to go to film school because Stanford didn’t have a film program at the time, and I was encouraged by a friend of mine who was– we had the same interests; we both loved ‘90s movies, and we both loved writing. We were writing together, and she actually found the school and she was like, “Yo let’s do this. Let’s just stop out temporarily and learn.” And it was hard to convince my parents because they thought I was dropping out of school, and I wasn’t, but it was just the best experience ever ‘cause I wouldn’t have gotten that at all at Stanford. I felt like really constricted in a way, and this really opened my eyes to all the things I could do myself.


What did you study at Stanford?

I studied African American studies and political science at Stanford. Not doing any of that now [laughs].

Looking back at all of the series that you’ve written and produced, do you have one that is your favorite?

The series that I’ve done that is my favorite is definitely my second series, Fly Guys Present “The ‘F’ Word,” just because it was me following my brother and his friends, and they’re just so funny. And most of the content wasn’t scripted; it was just me editing into a story and me giving them scenarios in a storyline, and they would just act it out in a way that was just too funny, and I would be laughing behind the camera the entire time, so I’m actually working with my brother again to produce another series in that vein. And “Awkward Black Girl” is just me. It will always be … “Awkward Black Girl” is me, it will always be a part of me, it will always be my favorite in a different way, but as far as something I’ve creating personally, it’s definitely Fly Guys Present “The ‘F’ Word.”

Did you feel like for a lot of your characters that there were little pieces of yourself in each of them or are they all pretty different?

There is always part of me. I can’t help that honestly, because whether I’m editing something it’s going to be from my gaze, when I’m directing it’s from my point of view, so I don’t know if that’s problematic or not but it’s fact. Yeah, I can’t help it.

You seem to be constantly creating new series and also juggling a lot of projects on top of each other. What is your creative process like? Are you ever nervous two projects will be too similar?

I’m always nervous they are going to be similar, and I ascribe to make different choices, and I strive to create different kinds of characters, but I’m usually nervous for nothing because when I have an idea it’s already different from what I’m already doing. The only thing they have in common is that they’re coming from me, that it’s my voice. But it’s so exciting and so fun to try and create new things.


What is that creative process kind of like?

My creative process is — I don’t know — it is kind of non-existent. I usually go to the bathroom and come up with an idea there. While I’m in the shower I come up with the most ideas, and then I write them down and then I’ll develop them either a couple weeks later or years later, but a lot of the stuff I’m producing right now is stuff that I just wrote down in a notebook two years ago and was like, “Oh, now I have an opportunity to produce them, let me do them.” But I just constantly come up with ideas. Even reading articles sometimes, funny articles, they’ll inspire like movies or different storylines, but when I come up with an idea I just have to be in the right mindset to execute it.

How do you feel like your role has changed from writing your own content to now producing it?

Wow. I love writing and producing my own content because you get to see it from start to finish, you get to ensure that it’s properly told in your own voice, where I think before I was satisfied with writing and just giving it off to someone, but I don’t think I could ever do that now. Even with the project that I just wrote, I was like, “I’m just going to write all these episodes and then — whew — give it to somebody and I’ll be free.” But I can’t do that anymore! Especially having written something and executed it myself and knowing I have a particular vision that I can actually execute, like why not do it? It’s put me on some sort of power trip in a way. An unhealthy power trip.

You have to be involved in all of it?

I have to be involved in everything. It’s ridiculous. Maybe soon I’ll be able to take a step back and be like, “Here, you take it.” I’m kind of like that with certain directors that I trust but otherwise it’s hard.


Do you miss being as involved as an actress in your own series?

I definitely want to take a step back from being in my own stuff. I just really want to go back to take acting courses. I keep saying I’m going to do that but I just haven’t had the time, but I really love watching other people who are great at it do their stuff. There is nothing more satisfying than watching someone who is good at what they do bring your stuff to life.

Why do you think YouTube is such a good platform for your content?

YouTube is great because, one, I really, really love the instant feedback. Like you can know within seconds or minutes whether or not people are feeling your stuff, and I think that’s rewarding. It can be hurtful, like it can hurt your pride and your ego sometimes, but it’s just so great. I love that; it humbles you in a way. The idea that you can put out so much different stuff, like you can literally experiment as much as you want to and people will watch. I think having your own audience and being able to cater to a specific audience and try to expand the way that we tell stories, the way that we interact with a lot of the viewers is just amazing to me, and a lot of our viewers have had stake in sort of how storylines will develop, and I think that is really cool because you can’t do that in television, you can’t do that in film, it’s just final.

How do your viewers play a role in developing your storylines?

I used to read all the comments. I only recently stopped like three months ago, and like sometimes they’re really helpful. They’d be like, “Oh my gosh, I’m not feeling this character, he doesn’t seem like he’s developed,” or “Oh, I want to see more of this,” so in that way when I was shooting episodes monthly I was able to incorporate some of their feedback into what I was writing. But now I’m writing and shooting a lot of things in advance, so it’s just like, “Oh, if you don’t like it, sorry. I can’t help you there.” But it’s really, really just great to get the feedback, and our viewers actually fund a lot of content too. They donate, they spread the word, they’re the most precious part of this whole experience.


How did you know with those comments when to take comments seriously and when to just kind of move on from a comment?

It’s kind of easy to tell when something is constructive and when something is just stupid. So it’s kind of easy to filter out like, “Okay, this person is just saying, ‘You suck, go die and kill yourself,’ can’t really do anything,” but this person actually seems to be in tune with how stories work, how characters work, and I mean I want in a sense to cater to that audience, so I’ll listen. I don’t listen to everything. Sometimes people will make good suggestions about like how a story could go, but I’d be like, “No, I’m set in my ways. It is going to happen this way, so it just depends on what you want to listen to.”

Was it hard in the beginning when you were putting out something you were so passionate about if people were really critical about it or said mean comments that didn’t serve any purpose but to hurt you?

Yeah, when I put out “Awkward Black Girl,” because it was so close to me and it was the first time I was putting myself on the screen, I was bracing myself for all the negative comments, and it didn’t happen immediately. It didn’t happen until we put out the tenth episode, and up until then all the comments had been overwhelmingly positive, and then like a lot of people didn’t like our tenth episode so it hit me super hard like, “Oh my gosh, they don’t know. They don’t know what’s funny!” And I took it kind of personally, but then it just happens, so now I still read the comments from time to time and if people don’t like it then it just motivates me to do something better, or sometimes I just don’t acknowledge it at all. It doesn’t affect me as much anymore.

What projects are you currently working on?

I’m working on a couple of new web series. I’m working on a series called “The Choir” for Tracey Edmond’s premium channel Alright TV. I’m executive producing or distributing a show called “How Men Become Dogs” that is by two great writers and another series, “Roomieloverfriends.” I’m collaborating with Black & Sexy TV who I’m big fans of; they are really good about content, and then writing a couple more of my own and then working on television and film projects.


What opportunities has YouTube given you that you probably wouldn’t have gotten pursuing traditional media?

YouTube has given me everything. It’s allowed me to be independent and helped me to become an entrepreneur in a sense, and it’s just provided me so many opportunities that I wouldn’t be able to do 5 or 10 years ago. Just provided the platform and I’m indebted to YouTube. Not really though — I’m not going to pay them at all [laughs].

That’s okay, we will let them know. When you want to collaborate with others, what stands out to you about certain projects that makes you say, “I want to be involved in this”?

I really look for three things. One, if it is unique or told in a unique way. Two, if it makes me laugh or brings out some sort of emotion, and three, if it fits within what I think is my sort of brand of storytelling and comedy. Even if it is funny and amazing but it wouldn’t necessarily resonate with my audience, I wouldn’t go after that. I would support it but I wouldn’t distribute it.

How would you describe your brand and your audience to someone who hasn’t seen your work yet?

I would say that it’s universally-specific humor, and I try to cater to audiences of color in a way that everyone can appreciate it.


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What opportunities does YouTube have for creators of color?

I think that YouTube really just provides a unique platform for the underserved. Like earlier we’re not really represented in mainstream media in terms of film and television, and a lot of content creators can go online and say, “If I’m accepted here then I know that I can find an audience starving for content and starving to see a representation of themselves,” so YouTube has provided that opportunity. YouTube has provided that gateway.

Do you think as that community online continues to grow it will have an influence on traditional media?

I think that it will definitely start influencing traditional media, and I think it already has. I think a lot of people are scared of social media, and by people I mean a lot of studios and corporations are worried that they are going to become obsolete, and they might — who knows? I don’t know what’s going to happen, but I think that the best thing is to work towards really, really trying to fuse the two, but I think that networks, cable, they’re definitely paying attention and trying to incorporate social media especially into everything that they do because they see that there is a lot of power in that and that a lot of our generation doesn’t even have TVs anymore, so I think it’s really important to consider that.

Do you still consider YouTube a stepping stone moving you to television and film?

I’m interested in television, but it’s crazy that I’m more concerned about my online content just because I know that it’s there and I want to serve that audience, and I feel like in a sense it’s more appreciated there, but right now television and film are still held on a higher standard. I think people are starting to take YouTube and digital content more seriously but it hasn’t reached that level of respect and prestigious that television and film has.


What are your personal long term goals?

I mean I definitely want to be a producer of content. I want to produce content for people of color on all platforms. If it happens that all these platforms are obsolete, then one platform it doesn’t matter, but I just want to keep telling people’s stories and tell my own.

Who has been a big influence on your work?

Big inspiration for me: Tina Fey, Donald Glover, I love Larry David and Jerry Seinfeld, Chris Rock, Gina Prince-Bythewood on “Love and Basketball,” which is my favorite movie of all time. I find inspirations in all places, but those people have definitely been huge inspirations for me.

As a comedy writer yourself, are you ever nervous that a joke is super funny to you but not to anyone else?

Yeah, and it happens all the time! It just comes with the territory. If I think something is funny and somebody else doesn’t think it is funny, then oh well, but usually I hope there is like a balance where they think that more is funny than not funny.

Aside from all your creative work, what are your days normally filled with?

Lately it’s just been a lot of writing, non-stop writing and revising because I’m working for a couple of different channels. I do my own merchandising, so there is always shipping shirts and advertising them. Social media and tons and tons of meetings. I’m always meeting with people, trying to either collaborate or see what other opportunities there are, and lots of shooting. I shoot a lot, and I’m on set a lot.


How do you balance it all?

I don’t know. I don’t know how I balance any of it. It’s actually kind of hard. Sometimes I get overwhelmed but usually my to-do list and my calendar keep me sane, and I love crossing things off my to-do list, so that really keeps me motivated. Sometimes I add something just so I can cross it off.

I do that all the time.

It’s the best thing!

Like add something I’ve already done.

Its just fulfilling. Checked my emails, oh I did it. Listened to the news, oh I win.

What is something you can’t write without?

Something that I can’t write without is probably my phone as stupid as it is. I need to Google stuff and look words up and check the news sometimes that informs a lot of my writing, but it’s just a handy tool there that is everything that I need to know. I’ve almost used several words wrong, and I was like, “Whoops, I’m glad I looked that up,” so it’s helpful.

So knock on wood, but say your house was on fire. What are three things you would grab?

[laughs] First off, knock on wood somewhere. If I had to grab three — I’m just such a tech whore — I’d grab my computer, my notebook because I write everything in my notebook and my box of memories that I keep in the back. It has stuff from my life like letters and stuff from friends, and pictures, stuff that keeps me grounded. I’d be sad if I lost it.

Would you grab any of your trophies?

No they’re online. I know they exist.


What award has meant the most to you?

Definitely the Shorty Award. That one was great because we didn’t even campaign for it initially; people were just nominating us out of the blue, and then once we found out that we had a shot at being in the top five then we started really pushing it, and then we won and then it came accompanied with lots of racist comments. That process was really, really eye-opening in a way, but it just ended really great because a lot of the racists hadn’t even seen the show, and one of them that was like calling all kinds of horrible slurs the next day was like, “Oh I take it back. I watched your show, and it’s really funny.” So I was like, “Yes we appeal to racists too.”

How do you respond to racist comments?

I just retweet them or laugh. There’s not really much you can say. If someone hates you for the color of your skin then what can you really do?

Is racism still a prevalent thing on YouTube?

On YouTube oddly enough it is. I’ve never experienced– I can’t say I’ve never experienced racism in life ‘cause I’m sure I have. I just can’t remember it or I haven’t cared, but online it’s like a playground for people who don’t like other people to really share their sentiments. And I applaud them for that. If they can find other friends who hate people and be bonded in that then good.

What advice do you have for other women of color who want to break into the YouTube creator world?

For women of color, to just do it honestly and work with people who are equally as passionate as you are. I wouldn’t have been anywhere if I didn’t have great people who are thorough and who are smart and believe in what I’m doing, and I think that it’s important to have a really good team around you. You can’t do anything by yourself. You can try but no one does anything alone.

When you look back, what are the most prominent memories that stand out from your career so far?

I’m just always positively overwhelmed by the support of people. The people who come up and who tell me stories about how they can relate and tell me about how their parents put them onto the show or how it helped them get through things, like that’s just the best memory for me. I love meeting people who support me. I mean, who wouldn’t?

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Photography by Sean Willis


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