Before Issa Rae was starring in and showrunning her own TV series or playing President Barbie, her journey started on YouTube.
The multi-hyphenate worked on two web series before starring in her own, making her uniquely qualified to speak to the moment Hollywood finds itself in as the creator economy booms and disruption is rampant — topics she discussed at length at TheWrap’s Creators x Hollywood Summit on Wednesday in Los Angeles, in partnership with Whalar and The Lighthouse.
Rae knew that mainstream Hollywood in 2011 would never pick up a show like hers, so she decided to commit fully to building her own digital audience with “Misadventures of an Awkward Black Girl.” This strategy paid off when the show gained popularity organically, reaching its target demo and later receiving additional promotion from YouTube itself.
“I started ‘Awkward Black Girl’ because there was a dearth of representation in the industry, and it felt like this was my opportunity to put an archetype into the space that didn’t exist at the time,” the producer told TheWrap’s Raquel Calhoun, who moderated the “Paving the Way: Creators in Hollywood” panel Wednesday.
“And now, even after so much progress, we’re kind of back to limited representation and having to stake claim of our stories,” Rae added. “We’re back where we started, in a way, but wiser.”
The Hoorae Media founder reflected that years after her HBO series “Insecure”’s success, the entertainment industry seems to be taking significant steps back from telling diverse stories.
Creators and executives are “tiptoeing” around it, she said. The producer specifically noted that even some executives of color have told her that they “can’t cosign you” for fear of losing their own jobs.
“I’m seeing it. Just blatantly. People aren’t investing like they were before,” she said. “[DEI] has changed meanings and has become a bad word.”
The producer clarified, though, that her production company Hoorae’s mission to tell inclusive stories has not changed – “and it never will,” she added.
“You have to be smarter about how you package and market [projects]. You tell them, ‘It’s not a show about a Black woman, it’s a show about class,’” she explained. “As icky as that might feel, it gets the show sold.”
The writer-producer turned her successful YouTube series into a traditional Hollywood career. Rae revealed that she was approached to adapt “Awkward Black Girl” into a television series, but she turned it down.
“They talked about recasting everyone, including me, with celebrities, so that was an easy no thank you,” she joked.
Rae explained that Hollywood executives did not understand what she wanted to create and that an adaptation would have done a disservice to her vision and her already dedicated audience.
The producer eventually got a meeting with HBO, which had a collaborative approach to producing her first linear project “Insecure.” Reflecting on those early days, the producer said she learned in the transition from YouTube to Hollywood that she approached executives with the wrong attitude.
“That – ‘What can I do for you?’ – was the wrong mindset to adopt,” she said. “I should have been like, ‘I have these things for you that I specifically want to do, and I know what I want to say.’ It took me a while to get there.”
When it came to creators entering the business today, Rae was candid that Hollywood has gotten lazy. A proof of concept, whether that be a short film or a digital series, can turn heads with executives that no longer want to read to discover talent, she said.
“I feel like Hollywood is in an identity crisis right now, and so they’ve turned to creators and social media in an attempt to try to bring them into the system,” she said. “I don’t think that that’s the right model.”
The creative executive herself advised creators to keep their heads down and engage with their audiences on the platform directly, honing their storytelling voice. She said that the biggest asset Hollywood can provide that creators can’t do on their own is marketing on a mass scale.
“Hollywood has gotten a bit lazier in their discovery, whereas they’re not reading as much,” she said. “It’s been disheartening to see Hollywood not make the extra effort to discover other voices outside of what’s already been risen to the top as popular.”
Rae also announced that her production company Hoorae has partnered with TikTok on for its first microdrama series “Screen Time.” Together, TikTok and Hoorae will co-develop a slate of additional micro-series that will air exclusively on TikTok and its new microdrama app, PineDrama. “Screen Time” will land on the platforms later this month.
“I want people to feel like Hoorae is a part of their daily routines and part of their lives,” Rae said. “And this feels like an accessible point.”
TheWrap’s Creators x Hollywood Summit is an invite-only gathering of the top creators, entertainment leaders and brand partners who are shaping the future of storytelling and the new entertainment economy.
TheWrap’s Creators x Hollywood is presented in partnership with global creator agency Whalar and The Lighthouse, both part of the Whalar Group. It is sponsored by City National Bank, Fox Entertainment, Lionsgate, Loeb & Loeb LLP and WEBTOON.
