Editor’s Note (2/3/2020): The below article was originally published on September 23, 2014.

Today is the launch of Issa Rae Productions’ ColorCreative.TV, a platform that will introduce three new half-hour television pilots by underrepresented talent into the TV landscape. Recently, Shadow And Act spent time with Issa Rae, her friends, family, and professional team for an in-depth look at how ColorCreative got started, as well as Issa’s life and career, and how she’s built “The Misadventures of Awkward Black Girl” into a full-fledged entertainment brand.

“Television today has a very limited scope and range in its depictions of people of color… We want to change that.”

So goes the tagline of the “Misadventures of Awkward Black Girl” Kickstarter campaign, which raised over $56,000 online and effectively launched the career of multi-hyphenate content creator Issa Rae back in 2011. Before then, she was producing and funding her web series out of pocket with a small group of collaborators and limited resources. But when Issa took to Kickstarter to request the funds to produce a second season, it was the audience – a large cross-section of many young, awkward, and black YouTube viewers who appreciated the diversity in the series and related to Issa Rae’s comedic voice – that turned out in massive numbers to support the project.

In the three years that followed, she was not only able to fund another season of “ABG” in partnership with Pharrell Williams’ iamOTHER multi-media collective, but the success of the series led to a number of other projects – currently, a TV show co-written with Larry Wilmore for HBO, a hosting gig on Aspire TV’s talk show “Exhale,” a Lorraine Hansberry biopic in which she’s set to play Nina Simone, a book of essays for Simon & Schuster that’s due out in February 2015, the launch of three television pilots with ColorCreative.TV, several web series on her thriving Youtube channel, and more.

“This could be complete bull, but I would say that 40% of my time is spent producing and working with other writers of color, and the other 60% is developing and working on my own stuff,” says Issa from her new offices in Inglewood. She and her staff have taken up residence there as the central headquarters for Issa Rae Productions. On the day of our visit, the space is a flurry of activity, filled mostly with young people and women of color of every shade, hue and background. A group of interns work on a live event in an outer office, while in an inner office, staff and cast members prepare for a table read.

Sitting at a desk across from producing partner Deniese Davis, Issa is a lot like her “ABG” persona – a layer of self-deprecating humor thinly veils a vibrant spirit, wittiness and genuine insight about society and the entertainment business. She alternately preps for the table read while firing off tasks on her laptop and in between, gives a status update on some of her upcoming projects. She and Larry Wilmore have turned in their final draft of “Non-Prophet,” their script for HBO. “I love it. It’s my voice, and he’s helped me to bring it out in a way that I couldn’t have done alone. It’s about a girl who doesn’t know who she is or where she’s going. It’s relatable and universally specific, which is what I aim for in my content.”

She explains how she’s reaped the benefits of working with an industry veteran like Larry Wilmore, who wrote on shows like “In Living Color” and “The Fresh Prince of Bel-Air” before creating “The PJs” and “The Bernie Mac Show.”

“He’s taught me a lot about standing your ground on your vision. He’s like ‘Fuck no, if this is what you want to do, then this is what it’s going to be. Any notes need to cater to your vision and you can’t waver.'” She also hopes to apply some of the lessons learned from her last TV experience with Shonda Rhimes and ABC on a project that ultimately didn’t work. “Since it was my first TV project, I was more malleable in a way and hesitantly so, but I felt like I wanted to get it made and I’d do what I had to do.”

Ultimately, she points to branding as the reason that the ABC project didn’t take off. “ABC has a core familial audience and a core set of values. In all of their shows it’s about family and how the group comes together at the end. I was trying to do something called ‘I Hate LA Dudes’ that was very antihero, even in the title itself. So it was like, ‘How can we come together with these men in the end and still be a family? Because that’s what ABC is.’ And I was like, ‘It’s called I Hate LA Dudes. I literally hate them. I’m not going to come together with them.’ And so in that way I still had to figure out how to wrap my creativity around this core theme. I tried, but it just wasn’t going to work.”

In preparation to write her book, she’s read other memoirs by women like Sloane Crosley, Mindy Kaling and Tina Fey, but was really inspired by Stephen King’s On Writing. “It actually made me feel like I could do this. Transferring mediums was hardest – going from screenwriting, where it’s really dialogue-heavy and descriptions are what you make of them, to prose and being descriptive and trying to have an elegant writing style at the same time.”

She also calls the book the most personal material she’s ever written. “I’m still going back and forth with that because it explores a lot of things I haven’t told friends or said out loud. Everything else has just been pieces of me and attempts to make people laugh. ‘Awkward Black Girl,’ that’s a part of me, but it wasn’t necessarily my story. And the project with Larry Wilmore, it’s my friendships, a lot of my insecurities and fears, and it’s still a lot closer to my life than ‘Awkward Black Girl’ was. But the book is the closest. It definitely takes the cake.”

The Lorraine Hansberry biopic project with Taye Hansberry and Numa Perrier is still in process, and the script is being researched and polished. She’s excited for the chance to play Nina Simone, whose music she discovered through a high school teacher. But she also feels that some of the attitudes surrounding her casting, especially in relation to Zoe Saldana in a previous biopic, are silly.

“There’s going to be pressure either way, internal pressure because I want to represent her appropriately. But people shouldn’t be any more relieved that I’m darker [than Saldana]. I haven’t proven anything yet, and I was still met with resistance that I can do it.”

“You’re Officially YouTube Famous”

“I thought I was going to be an actress in high school, but the younger me always wanted to be a writer. I loved technology and I was always on the computer, much to my mother’s dismay. And I always knew that I wanted to tell stories in some way.”

Like a lot of kids who eventually get into entertainment, Issa pursued conventional career paths like medicine and law before starting to create her own content. “There was always going to be an entertainment aspect,” she says. “I thought as an actress, I could write really compelling testimony as a lawyer. It was really stupid. Then I discovered that I loved behind the scenes work. I loved directing and writing for actors when I was in school plays.”

She spent her childhood in Senegal and Potomac, Maryland before settling in Los Angeles as a teen. In a large household of four other siblings, parents and occasional extended family (“In Senegalese tradition you can show up at the door like, ‘hey, I need some place to stay’ and they have to say yes”), they spoke a blend of Wolof, English and French.

The mix of cultures had an effect, especially in her sense of belonging. “We moved from Maryland at a young age, where it’s kind of suburban and slow, over to LA where it’s fast-paced and kids are mean,” recalls younger brother Lamine “enimaL” Diop. “So she grew up not really fitting into the norms of what cool was in LA and it was a tough transition.”

Even now, she struggles with how to include her Senegalese background in the content she’s creating. “It is something that I want to explore down the line, I just haven’t figured out a way to blend the two together where it wouldn’t ostracize one or the other, where it’s more inclusive,” she explains.

“It seems like there is such a separation between African culture and Black American culture, and there is a disconnect there. So ‘Awkward Black Girl’ feels very American because that is my American experience. But a lot of my feeling awkward early on was moving to Maryland, being African and being exposed to this perception of what Africans are supposed to be like.”

As for Issa’s humor, Lamine believes she gets a lot of it from their mom: “She’s just really ridiculous and does silly stuff. People don’t really see it because she has this kind of strict schoolteacher persona in her work life, but at home it’s a completely different story.”

Along with her younger siblings, whom they collectively referred to as the “bottom three,” Issa explored her creative side through games, homemade productions and original songs. Her current rap group, The Doublemints, is possibly inspired by Star 69, a group she formed with friends as a kid.

Entertainment didn’t seem to become a serious goal until after she attended Stanford and moved to New York, then again to LA. She started a web series with Lamine and his rap group The Fly Guys, called “The F Word,” before channeling her own experiences into “The Misadventures of Awkward Black Girl.”

When that first episode hit, it eclipsed all the views that we had on any of the videos we had done previously, in like a day and a half,” Lamine recalls. “When it got to a million views I was like, ‘Oh yeah, you’re officially YouTube famous.’

Lamine continues to work with Issa, most often scoring the music on other productions, and cites her success as an inspiration. “It’s just nudged me to push myself. Because I didn’t know that composing or scoring film was something that I could do. It seemed like such a huge undertaking to really get it going, but I realize that it’s not as complex as I was making it out to be and I learned that just from working with her. Seeing how it works really sculpted my belief in myself.”

What seems to define Issa from other content creators is the point at which “Awkward Black Girl” became a success. Rather than focus on a single project, she went on to produce additional series including “Roomieloverfriends” with Black&SexyTV, “The Choir” for Alright TV, and others. To help manage social media and new business opportunities, she brought on Benoni Tagoe, who encouraged getting other content creators involved. “There came a time when we had accomplished so much on YouTube that Issa started to get really busy with things off of YouTube,” Benoni says. “So the plan was to give her a chance to focus on other initiatives by using her channel as a distribution outlet. We know our audience very well, we know what they gravitate towards, so why not give other content creators a voice to showcase their talents on a platform that’s already built?”

So Issa started hosting projects from several new content creators on her YouTube Channel, including pop culture series “Let Leslie Tell It,” cooking show “Butter + Brown,” romantic drama “First,” and others, effectively becoming what some call the “Shonda Rhimes of the web.” Other content creators have been able to learn from her process of trial and error. Jahmela Biggs, who writes, produces and stars in “First” as Issa did with “ABG,” was able to lean on her experience. “I’ve done several projects, but never a series,” Jahmela explains on a day when she and Issa meet to download the end of the season. “I’ve been fortunate to have a team of producers who were there from the beginning, they believed in the material and have been instrumental in giving feedback.”

The financial end of the business continues to be a work in progress. “It is still incredibly hard to monetize content on the web,” Benoni says. “For us, it was all a matter of timing. We just so happened to have a hot, ‘urban’ web series at a time when Google launched their 100 Million initiative. So when channels were looking for that kind of content, we were always first in the door. We were able to sell a couple of shows and use that income to help generate more content.”

Recently the company also adopted the monthly funding platform Patreon to help bring in additional dollars. “That was in consideration of my creators who are lending content to my channel,” Issa says. “YouTube AdSense only gets you so far, especially when the viewership fluctuates. So this provides an opportunity to put money aside to help fund other projects and other seasons down the line.”

For ColorCreative, there’s an eye towards corporate sponsorship. “That’s just a field that I’m navigating, looking toward investors but not wanting to water down the material; and then being worried that while this is technically a start up, it’s still media, and I don’t always know where that fits where television is concerned. There’s a lot of confusion, but we’re figuring it out as we go.”

“Help us change the face of Hollywood.”

Last year, Issa met with producing partner Deniese Davis to discuss how to create a platform for underrepresented
talent in television. They came up with a plan to independently produce three half-hour comedy pilots, or stand-alone episodes used to sell a TV show to a network. They called it ColorCreative.

Each pilot would be produced for $50,000. They would select the scripts in winter, prep in the spring, shoot in the summer and release all three pilots in the fall with the intent to bring them all to series on television.

“I’m not a seasoned writer by any means, but I’ve been spoiled by the Internet and being able to have an idea, write it, produce it, and put it out there for an audience in a matter of a week or a month,” says Issa. “And then dealing with a very formulaic broadcast network – or even one that gives brilliant notes like HBO but has all the time in the world – it can be frustrating in that process, especially for new writers. I know that in my first experience, my voice was kind of lost in the notes and in the process.

“And so I want to give writers an opportunity – women and writers of color especially, because we’re the least represented and we’re the most likely to be told that our voice isn’t broad enough to reach an audience – an opportunity to say, ‘Hey I love your work as is. We want to produce it. We want to show a network that there’s an audience behind it and that people want to see it, and it’s great as is.’ And the YouTube experience has sort of informed that. You get instant feedback. People will tell you right away whether or not they love it.”

Deniese, an AFI graduate who worked on music videos, short films and other online media before joining Issa Rae Productions in 2012, helped streamline a production schedule of three six-day shoots that would take place within days of each other, each with a separate production team.

In addition to showing underrepresented talent on screen, they had targets for diversity behind the camera. They wanted at least two of the pilots to be written and created by women, and they searched for women and people of color to direct, shoot and edit the projects as well – a timely decision, considering the DGA’s recent diversity report and the abysmal numbers of women directors in television, or The Hollywood Reporter’s recent retrospective on the past 53 years of top TV showrunners.

“We’re still being boxed in,” says Victoria Mahoney, who directed the ColorCreative pilot “Bleach.”  “There are all these rules about who gets to play. So even if you’ve proven yourself in television, there’s still this big question about whether a woman can direct a TV show. So while everyone’s out arguing about whether or not women and people of color are capable, we’re just going to go ahead and create our own content and let them decide after we have the content out in the world.”

From a pile of more than 50 scripts they found by referral, Issa and Deniese narrowed it down to three projects they wanted to produce. All three happened to be written by relatively new writers: Brittani Nichols, whose “Words With Girls” pilot began as a web series; Shawn Boxe, whose script for “Bleach” was found on The Black List; and Syreeta Singleton, a recent college grad whose script “So Jaded” went through one of Issa’s workshops, and was her first piece of produced work.

“It’s kind of surreal,” Syreeta Singleton explains from the set of her pilot. “It’s incredible and it’s humbling because this is my first time writing comedy. It’s my first time writing anything that I felt should be on television. I was a full-time student and full-time nanny, but I was working on all of these stories. And now I see that it’s not as hard as I was trying to make it.”

Issa and Deniese agree that the writers and their position in the industry came secondary to the material. “I’m just looking for good stuff because I’m a fan first,” says Issa. “I just love good content and I know that it’s out there, by us. It’s just not getting acclaim or attention. And while my platform is still small, it’s more than they may have on their own.”

Victoria adds, “In traditional network television, there is so much time wasted on talking about the thing you want to do and begging and pleading and trying to prove yourself, when that precise fragment of time can be used creating. And for directors, our learning curve is directing. We have to continue to direct to grow and expand and learn and shapeshift. But there are so many incredible directors dying on the vine waiting for permission.

“What I love about this generation is that we are refusing to sit and wait for someone to anoint us. ColorCreative is finding a way to get talent – writers directors and stories that are disregarded, that are completely devalued in the marketplace – to an audience where they belong. And let the audience decide if they want it.”

The ultimate goal is for all three pilots to end up on television in some form, in which case Issa Rae Productions would stay attached to the shows as non-writing Executive Producers, helping to navigate the process of working with networks while keeping the original writers’ voices and visions intact. Barring a TV deal, there are other milestones to achieve as well: getting representation for the writers of the pilots, and getting them hired as staff writers on other shows. There’s also the possibility of keeping the ColorCreative shows on the web. With Youtube, Amazon, Netflix, Hulu and others in the rapidly-evolving online original content space, there are plenty of options.

Issa has her own longterm marks to hit as well, like owning her own studio. “Television is just one goal, but I love the digital world and I think it’s already blending. So a studio seems realistic, and it would allow me various avenues and mediums.”

In the meantime, ColorCreative.TV has been a huge undertaking, and one that she’s proud of. “I had to do it,” she offers. “If I didn’t do it then I would be kicking myself. It comes from being impulsive and it’s how ‘ABG’ started. It’s how my web videos started. It’s from a restlessness that I have and whether it’s successful or not I’ll feel content in doing it, so I can move on.”

When asked where that restlessness comes from, she says, “Time. Feeling like I’m running out of time, like someone else will step in. I don’t want that regret. Even with these 30 Under 30 awards, the 35 Under 35, it seems like your accomplishments have to be within a certain age range for you to be respected. It’s like, what about the people over 35? That’s in the back of my mind somewhere clearly, because I’m about to be 30.”

How she deals with the restlessness and dissatisfaction seems to be by creating more content, and being active where others tend to become stagnant. “We’ve all watched her do things that other people can’t or haven’t or are sitting around talking about, and Issa’s doing it,” explains Victoria. “She just keeps moving the needle in a way that’s so exciting. She could have taken this money and done something on her own, but she did one of my favorite things that Ava [DuVernay] does in film, which is she supported other talent in a massive way, through the writers, the directors and the actors. No one else has done that in TV in this way. No one, with outliers. So that is impossible to not want to be a part of.”

But for Issa, it all depends on how her efforts are received, and there’s a massive amount of pressure to achieve some sort of success. “I don’t like to show that I’m fighting for respect,” she says. “So for me it has to be very subtle. I like to just come out of the gate with something that I’m impressed with and happy with that’s well-received and say, ‘Ha, here it is.’ I don’t want to feel like I’m catering to someone or trying to please or impress them. Inside I might be looking for validation in some way, from certain parts of the industry, but I don’t want to feel like I am.”

And with what she’s achieved so far, has she gotten that validation?

“No, I feel like I’m still fighting. I don’t feel like I’m established or on stable ground. I feel I’m like a duck, pedaling and trying to stay afloat.”