The outside of the Sheraton Delfina Hotel in Santa Monica was bustling with activity. A thick Autumn mist obscured the sea and the sky was grey, but the mood was warm. People milled outside the hotel lobby on their cell phones, tweeting and texting their excitement, sharing it with their invisible digital friends. Myself and my friend Chie approached a concierge, unsure of where in the hotel our conference was taking place. “Oh, you must be here for the Awkward Black Girl workshop?” We probably looked the part. Two young black people in a ritzy hotel, me in a strawberry print peak cap and Ghanaian Kente cloth sneakers. “Yep, that’s the one,” we answered.

The event we were attending was called New Media: The Next Generation – How to Create, Distribute and Market Your Digital Footprint. While there was an impressive list of new media experts, internet celebrities and Vine stars (the Twitter-owned video app) the real draw card was Issa Rae, the creator and star of the wildly popular web series The Misadventures of Awkward Black Girl. Rae and her team from Issa Rae Productions were also the hosts of the event. She walked coolly through the lobby and brushed past a few of the workshop participants with an unassuming elegance. With cropped natural hair and hipster glasses, she seems a little taller in real life than on YouTube (television and film usually has the opposite effect). After a series of talks of how to create, launch, and monetize web content, including a talk by Rae herself, the participants were invited to meet and greet the speakers. I stood in a line waiting to talk to Rae, the nerves of a fan overpowering my journalistic cool. As the woman in front of me got to the front of the line she gushed, “I don’t really have a question for you. I just wanted to meet you, and to say thank so much you for what you’re doing.” Rae graciously thanked the woman for her support, shook hands, and then I was next up. I managed to keep my cool, but barely.

A few months later, I met with Rae at an apartment complex in downtown Los Angeles for a video interview. She came down to greet us in the plush marble floor lobby. I joked that the intense security and faux-Tuscan architecture was very Johannesburg. We shared a laugh about this, and later found out that this is where she is now living. She wore a self-aware sweater with ‘hash-tags’ printed around the arms and a frontal print declaring “Internet Celebrity.” Rae has a natural ease, a sense of quiet confidence very unlike her character Jae in her hit web series. “You know, now I meet people and they’re like “Oh, you’re not that awkward!” And I’m like, ‘Fooled you!’”

The Misadventures of Awkward Black Girl centers on Rae’s lead character J, a twenty-something black woman in a dead-end office job for a weight loss company called Gut Busters. Rae sums the show up as “a web series about a girl who uncomfortably navigates life, love and her job. It’s about the mundane social experiences we all have.” Her character not only has to navigate every day trivial office life (and her ingratiating co- workers) but also the modern African American female experience. One of the reasons Rae started the show was because she felt she didn’t see herself or the people she knew reflected on film and television. “Real Housewives of Atlanta and Flavor of Love… I didn’t see myself represented in those shows, I was always a spectator. So the media’s definition of black excluded me, and that’s awkward. I was awkward based on that. What they portrayed a black woman to be.”

She started a film blog where she often expressed her disappointment in the lack of relatable African American characters on screen: “The same types of black movies were coming out with the same type of humor and I was voicing that on my blog. I remember one comment was like, ‘you complain so much, why don’t you make something.’ And I was like ‘Oh… OK…’” One day Rae was watching a talk show where someone asked the question “Where is the black Liz Lemon [Tina Fey’s 30 Rock character]?”It was as if her mind had been read. Her thoughts and ideas now expressed on national television via someone else, she knew she had to act quickly. “The ‘Awkward Black Girl’ character had been swimming around in my head for two years,” says Rae. “I knew in my mind that if I didn’t shoot the first episode at that very moment, I never would.”

She called up one of her best friends from high school, Devin Walker, to do the filming, and her dancer/choreographer friend Allan James to play her office fling. Neither had any film experience. By episode four, she brought on her ex-classmate Tracy Oliver to produce the series and improve the production values of the show. By then, the series had been passed around and shared on social media, and was creating a buzz online. Through the crowdfunding website Kickstarter they were able to raise over $56,000 in donations from nearly 2000 people. And that was just the beginning. By the end of season one, hip hop star, producer and pop icon Pharell Williams (N.E.R.D.) contacted Rae and spoke to her about a new YouTube channel he was starting called I am Other. He told her he was a fan of the show, and offered to put up the money for the second season and to host it on his new channel. From there on, the show took a trajectory of its own, and was seen by an even wider audience, becoming the most successful black web series ever. “Now, it’s beyond me,” Rae tells me in near disbelief. “ There aren’t even new episodes out, but people are still talking about it and claiming it as their identity. And I love that.”

While it may seem that her star has risen overnight, finding success has been anything but a smooth journey for Rae. She recalls a day where she and producer Tracy Oliver were sitting down to figure out their Kickstarter campaign, and in order to break away from the mundanity of budget planning, she headed out for a coffee break. “I was already in the red with my bank account. I decided to go get a cup of coffee. I had $1,27 and I thought that would be enough.” When Rae wanted to pay, she was told that the coffee cost $1,37, and the cashier refused to ignore the ten cents difference. This embarrassing moment was a tough wake up call for Rae. “I just thought, ‘Oh my God, what am I doing, did I make the right decision, quitting my job, this is a web series, what did I think was gonna happen?’” However, she got back to work with Oliver and they figured out their Kickstarter strategy. “I’m prideful at the end of the day and I think that it’s weird for people to just offer you money. I think it’s nice, but I don’t have anything to show for it, in my mind.” Issa Rae’s fans felt otherwise, and with their donations, made sure that the show lived beyond a handful of episodes.

Rae rewarded her audience by constantly engaging them online, responding to tweets, sending merchandise to loyal viewers, and even going so far as to read all the YouTube comments (something which you should never normally do). In season one, Rae and her team steered the episodes towards the constructive feedback she would get in the comments, and she paid close attention to what people liked. When they introduced a once-off character called White Jay, her audience responded so strongly that they made him J’s love interest, and the entire second season followed their interracial relationship as a narrative arc.

Today Rae finds herself somewhere between ‘internet celebrity’ status and mainstream success. Through the success of Awkward Black Girl she has not only cultivated a large niche audience but also gained attention from the industry establishment. She received a development deal with ABC to produce a pilot with Shonda Rhimes of Grey’s Anatomy, which sadly wasn’t picked up. She has continued to release web content on her own YouTube channel and has directed and produced a provocative faith-based series called The Choir for award-winning producer Tracey Edmonds’ Alright TV channel. She’s currently working on a pilot for HBO with Larry Wilmore of The Daily Show with Jon Stewart, and writing a book of personal essays and reflections. “A stupid book that’s the bane of my existence,” she says. “I like what I’m writing so far and I’m finding my groove, but it’s really hard.”

The daughter of a Senegalese father and an African American mother, Rae grew up both in Senegal and Maryland. In Maryland in particular, she found herself at the center of a diverse group of friends “from every race and ethnicity.” In this multi-cultural setting she felt that her difference was celebrated, and that she never had to explain herself. She was just allowed to be. When she reached the 6th grade, her family moved to Los Angeles, where she attended a predominantly black school. “Those kids hated me because I was different. I mean, I spoke white, my hair was nappy and not straight like everybody else, my clothes were terrible because they weren’t name brand. It was just like I didn’t fit into this definition of what they thought was black.” The young Rae felt like she had to compensate for not being black enough, going as far as speaking differently and writing essays in ebonics. “I always say with Awkward Black Girl, most of those experiences are based off of sixth grade. Like feeling out of place then.” At times this is evident in the show, such as the high school flashback scene where Rae’s character J enters a rap ‘cypher’ on the school playground to profess her love for one of her male schoolmates. His response? “Nah, I’m good.” One of the funniest and most quoted lines from the first season of the series came from J’s boss at Gut Busters, an oblivious, middle-aged white woman known only as Boss Lady. After seeing J’s new close-cropped haircut she asks: “Is that how your ancestors wore it?” Rae says this interaction was taken directly from an experience she had with a teacher at school.

Even though Issa Rae hasn’t slowed down since the creation of Awkward Black Girl, working on other projects and constantly releasing content on her YouTube channel (my personal favorite being Ratchetpiece Theater, a tongue in cheek review of trashy rap songs) her fans are still hungry for more ABG and regularly ask her about whether there will be a third season. I can tell that this irks her somewhat. She jokes that even when she shares pictures on Instagram, people write to her saying, “this picture of this shirt is great but when is the next episode of Awkward Black Girl coming out?” So at the end of the interview, I joke with a repeat of that question which she hears all too often. She gives a loud, sincere laugh and says coolly: “I don’t know. But maybe a movie. If everything else collapses, I’ll do an Awkward Black Girl movie.” She gives it a couple more seconds of thought, shrugs and says, “We finished the story.” While this news may be a bitter pill for her fans to swallow, the significance of the show is not lost on Rae. “The show helped me come out of the awkward closet and it helped other people come out of the closet as well. They were like ‘Oh is that what I was? I’m awkward? Phew!’ It’s comforting that there’s a diagnosis, small as it is, for what we’re all thinking, or what we all go through.” Whether there will be an Awkward Black Girl movie or not, Issa Rae has impacted black television without ever being on television. Her next moves will be very interesting to watch. Let’s hope HBO doesn’t pass on her pilot.