Inside Issa Rae’s quest to become a media mogul, improve living conditions in South L.A., and make more great TV
ssa Rae’s office in South Los Angeles overflows with trinkets from her many successes. Awards perch on virtually every surface. Three boxes of President Barbie dolls, her character from, sit high on a shelf. There are purple roses, bottles of LeBron James’ Lobos 1707 tequila—a company Rae invests in—and custom pillows fromBut at the moment, the item that Rae is most excited about is her brand-new Moleskine notebook.
Issa Rae’s rise is held up as one of the prime DIY success stories of the digital era. In college, Rae began making a YouTube web series,, her show about Black millennials navigating life and love in L.A., followed. A historic double-strike sent the industry into further disarray. In the end, Rae was grateful for the victories the guilds secured. “But there was the frustration of, ‘Oh, my gosh, this project that I’ve been working on for five years just disappeared,’” she says., with its culturally specific lens, local bent, and unabashed raunchiness, would have been greenlit by WarnerMedia today, as all executives seem to want, she says, is safe, “universal” stories.
Rae says she feels “secure” in her relationship with HBO at the moment. Nevertheless, she says industry changes have forced her to reevaluate the feasibility of “smaller, quieter projects.” “When you have all of these streaming services that are competing with each other, it means they’re also moving the goalposts of what success looks like and what their brand is. It’s all mush,” she says. “I know what my brand identity is and what I want to make.
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