Issa 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 last year’s biggest blockbuster, sit high on a shelf. There are purple roses, bottles of LeBron James’ Lobos 1707 tequila—a company Rae invests in—and custom pillows from Insecure, her hit HBO series that ran for five zeitgeist-capturing seasons.

But at the moment, the item that Rae is most excited about is her brand-new Moleskine notebook. Rae buys a new notebook every year and fills it with personal reflections, creative ideas, and tasks to complete for her many businesses. Last fall, her 2023 journal started getting so full, she wrote in smaller and smaller fonts to preserve space.

“I love Mondays, and the first of the year is like a super Monday for me,” she says. “To be able to open a new journal was very exciting in the nerdiest way possible.”

Rae, 39, is especially determined to turn the page because last year was “not fun at all,” she admits. In public, she was absolutely crushing it: She won a Peabody Trailblazer award, stole scenes in two of the year’s most hyped films, Barbie and American Fiction, and released the second season of her critically acclaimed Max show Rap Sh!t.

But as the tagline for season 3 of Insecure read, “glowing up ain’t easy.” And in her quest to become a media mogul on the level of Oprah or Debbie Allen, Rae has faced growing pains: she had to lay off eight employees during the WGA and SAG-AFTRA strikes; navigate a labyrinth of California business laws; and watch as her projects got sidelined or canceled. In January, Rap Sh!t was axed by Warner Bros. Discovery. Perhaps worst of all, Rae says she witnessed Hollywood backsliding on pledges to increase representation and diversity. “I’ve never seen Hollywood this scared and clueless, and at the mercy of Wall Street,” she says.

In the face of these roadblocks, Rae is hatching a slew of plans for a better 2024. She’s developing at least two new projects for HBO, including, she tells TIME exclusively, a project set in an “alternative present,” which will be the first show since Insecure that she will create, write, and star in; and a comedy set in corporate America, created in partnership with Diallo Riddle and Bashir Salahuddin, the creators of the shows South Side and Sherman’s Showcase. She’s also working to build a studio campus in South L.A.

Rae has long made it her priority to create pipelines for people of color, but as she scales upward, she’s learning more and more about how to balance her personal entrepreneurial priorities with a larger fight for equity. “I recognize that I have to do well economically to be able to make change,” she says. “That’s frustrating, that’s ugly. But I recognize that money moves things faster—and so much of what I do is with the intention to help make those moves.”

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, Dorm Diaries, with a camcorder borrowed from the Stanford library. She raised money for a subsequent web series, The Mis-Adventures of Awkward Black Girl, on Kickstarter, and praise for the show’s humor and relatability spread. A deal with HBO for Insecure, her show about Black millennials navigating life and love in L.A., followed.

Rae’s ambitions have always stretched beyond TV writing into entrepreneurship. As a child, she wore out her VHS tape of the film Twins, and was particularly absorbed by scenes in which Danny DeVito’s character stomps around with a briefcase concocting schemes. “It was nefarious, but there was something imprinted in my mind that I wanted that,” she says.

These days, Rae’s growing portfolio includes a production company (Hoorae), an indie music label (Raedio), a management company (Color Creative), a marketing agency (Fête), a prosecco line (Viarae), a hair-care brand (Sienna Naturals), and a stake in the U.S. SailGP Team. About a mile and a half from her Hoorae offices sits the Inglewood branch of Hilltop Coffee, a coffee shop that Rae co-owns; it’s about an eight-minute-drive from the house she grew up in.

Rae is certainly doing well for herself. In 2021, she signed a deal with WarnerMedia reported to be eight figures. But many of her enterprises are specifically geared toward creating opportunities for her community. Rae used Insecure as a breeding ground for Black talent, allowing writers, musicians, actors, producers, and others to cut their teeth on a prime-time HBO show. Her other businesses function similarly: she gives proteges titles and helps them grow into those roles. “If she can’t do stuff to bring other people with her, she’s not going to do it,” says Montrel McKay, Hoorae’s president for development and production.

Rae’s creative, entrepreneurial, and equity-driven goals coalesced with Rap Sh!t, her follow-up to Insecure. While Hollywood executives always prefer shows led by big names, Rae put her trust in a first-time showrunner (Syreeta Singleton), an early-stage TV director (Sadé Clacken Joseph) to helm the pilot, and two relatively non-famous leads (Aida Osman and KaMillion). She then set her many businesses to work on various aspects of the series. Hoorae developed the show; Raedio handled the music supervision; Fête cut deals for product placement. “That’s an ideal model, where we activate every single vertical,” she says.

But Rap Sh!t didn’t receive nearly the amount of online buzz that Insecure did—and in January, was canceled after two seasons by its parent company Warner Bros. Discovery, which, like many other media conglomerates, has been hell-bent on cutting costs. “The model used to be everyone chasing Netflix in buying as much as you can through programming,” says McKay. “And then when Netflix had that earnings report in early 2022 and didn’t show the same growth, everything kind of ground to a halt. We want to do opportunity creation for people. But we can’t do it the same way, because the money’s not flowing in the same way.”

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.

Hoorae is no longer involved with the adaptation of the New York Times podcast Nice White Parents, or of Brit Bennett’s best-selling novel The Vanishing Half. Hoorae developed Tre Cnt, a wrestling series with Dwayne “The Rock” Johnson, but HBO passed on it, McKay says. WarnerMedia also canceled Sweet Life: Los Angeles, a reality TV show Rae produced, after two seasons.

Rae believes there’s no way Rap Sh!t, 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. Its cancellation is just one example of what Rae sees as a larger withering of promises Hollywood executives made in 2020 toward increasing diversity and representation, both on- and off-screen. “There is a bitterness of just like, who suffers from you guys pulling back? People of color always do,” she says.

A UCLA diversity report found that in 2022, racial, ethnic, and gender diversity among movie actors, directors, and writers for theatrical releases slid back to 2019 levels after trending upwards for the three years. People of color accounted for only 22% of lead actors, 17% of directors, and 12% of writers. A report from USC Annenberg’s Inclusion Initiative in January called the entertainment industry’s previous pledges to support inclusion “performative.”

Rae does not mince words when it comes to the current leaders of Hollywood. “I’m sorry, but there aren’t a lot of smart executives anymore,” she says. “And a lot of them have aged out and are holding on to their positions and refusing to let young blood get in.”

In prior eras, Rae says, the money-making suits mostly stayed away from creative choices. “Now these conglomerate leaders are also making the decisions about Hollywood. Y’all aren’t creative people. Stick to the money,” she says. “The people that are taking chances are on platforms like TikTok: that’s what’s getting the eyeballs of the youth. So you’re killing your own industry.”

In an email to TIME, HBO executives signaled their ongoing support of Rae. “We’ve established a creative shorthand over the years and with every new project, we pick up right where we left off. There’s a flow to it that inspires me,” wrote Amy Gravitt, executive vice president for HBO Programming. “We look forward to what genres Issa and Hoorae will take on next,” added Casey Bloys, chairman and CEO of HBO and Max Content.

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. But if that doesn’t align with who’s paying me to make stuff, then that’s complex. We are malleable, but only to an extent.”

In the new movie American Fiction—which received five Oscar nominations, including Best Picture—Rae plays Sintara Golden, a commercially successful author who the film’s protagonist, Monk, believes to be a hack pandering to white audiences. In a confrontation between them, Golden tells Monk she’s simply being pragmatic about her creative and professional choices: “I’m OK with giving the market what it wants,” she says.

Rae’s own attitude is more nuanced. She understands the reach that movies like Barbie and Spider-Man: Across the Spider-Verse have, and the impact that she herself can have by appearing in them. On the Golden Globes red carpet, a moment in which two young Black girls excitedly recognized her as President Barbie went viral. “It took me a while to understand that when they see me, they see this version of Barbie that they aspire to be,” Rae says when I meet her a few days later. She’s still wearing the friendship bracelet they gave her.

But Rae has no aspirations of helming her own blockbuster franchise. “I’m just excited to create and see what I can do in this space where everything is asking for those big, IP-driven things,” she says. And while she’s operating in a tough environment, she’s used to navigating around rejection and discouragement. When she was pitching early in her career, executives told her there wouldn’t be an audience for a show about awkward Black women. One even advised her against centering a character with darker skin. “I know what drives me and I know what brought me in—and I remember when they were telling me that they didn’t want to make my types of stories,” she says. “So I’m still optimistic in that way.”

As Rae fights for representation on a national level, she is pouring resources into the betterment of her own neighborhood. She has invested heavily in the development of South L.A., which has been harmed by discriminatory policies like redlining and underfunding. When Rae featured local businesses on Insecure, they saw a jump in customers, which was soon known as “The Issa Effect.” In 2019, Rae chose to house Hoorae’s office just outside of Inglewood. A sparkling depiction of Nipsey Hussle, the rapper who was a local hero and was killed that year, hangs downstairs as a constant reminder of the company’s mission to uplift the surrounding community.

This year, Rae hopes to compound those efforts by building an entire campus for both local filmmakers and major studios. While South L.A. is a cultural mecca—think gangsta rap, the Black Arts Movement, Boyz n the Hood, Love & Basketball—it lacks film and TV infrastructure. Rae believes a production studio could serve as an economic engine for the neighborhood, providing union jobs while also sparking the interest of tourists. At the same time, Rae is all too cognizant of her role in the neighborhood’s gentrification, and is working through how to improve the lives of people in the neighborhood without displacing its residents.

Malick Diop, Hoorae’s chief financial officer (and Rae’s older brother), says an early bid for a piece of city-owned land for the studio was unsuccessful. But Rae is adamant that an acquisition will happen soon. “We have the investors; it’s just about locking in on that land,” Rae says. “When I tell you we’re ready, we’re ready.” She’s come this far—in developing the studio, but also in building her empire—and she’s not about to back down now.

“I have my little stake in this limited plot of land, and I’m gonna make sure that I bring in as many people to live on it as possible,” she says. “So until we run out of opportunities, they’ll be good.”