Issa Rae's success playbook: authenticity, outsourcing, and watching out for this red flag

I had never been to Inglewood, but it felt familiar. After watching the sun-drenched city, nestled on the southwestern side of Los Angeles, on five seasons of Issa Rae's award-winning series, "Insecure," I came to know a few landmarks around town.

The show itself had created one in The Dunes, a two-story apartment complex where Rae's eponymous character, Issa Dee, navigated life and love. It's now the backdrop to countless photos on Instagram, the platform of choice for the show's target audience — millennials.

I stepped out of my Uber Comfort in front of Hilltop Coffee and Kitchen, a Black-owned restaurant co-owned by Rae that was also featured in season four, episode two of "Insecure," a series documenting Dee's awkward experiences as a twentysomething woman trying to find her footing. Inside, the smell of freshly brewed espresso-based drinks wafted in the air as I tried to decide what I'd eat for lunch. As I looked up at the menu, my eyes caught these words painted on the walls: "We're all in this together," a nod to the communal seating that ran down the length of the bar.

Hilltop is just one of the many businesses that Rae has authentically branded in recent years. Rae said coffee shops are where she's most innovative.

"I'm a coffee shop girl," the LA native told Business Insider in September during New York Fashion Week. "I love to people-watch."

The multihyphenate was promoting another business, her new collaboration with Cast Jewelry, when I sat down with her inside the swanky 11 Howard Hotel. We discussed why she's getting into fine jewelry on a picturesque rooftop terrace in SoHo — far away from where her career started on the left coast, in Los Angeles.

Rae came of age online, YouTube specifically, during its gold rush era. Back around the 2010s, it seemed that anyone could turn on a camera and become a star. Justin Bieber did it. Chloe and Halle did it. Issa Rae did it.

So we rooted for them in a way that "Star Search" could never enable that level of intimacy. We thought Rae was a friend in our group chats, and in some cases, she was. Before baby boomers took over Facebook, Rae friended many of us, appearing on our timelines as just one of our friends, populating her feed with her own life updates, just like the kid in science class we rarely spoke to IRL.

"The Misadventures of Awkward Black Girl," her award-winning YouTube series launched in 2011, eventually led Rae to create and star in "Insecure," which followed four besties as they came of age in Los Angeles, and later a few roles in box office-busting films such as "The Hate U Give," "American Fiction," and "Barbie."

Despite staying busy onscreen, behind the camera, Rae seemed even busier. She partnered with Atlanta Records to launch a record label, Raedio, in 2019 and created a production company, Hoorae, two years later, eventually expanding it into an entertainment company. In 2021, Rae inked a $40 million deal with WarnerMedia, ensuring Hoorae's content found a home on any of its properties — from New Line to Max. Her investment in Hilltop, helping the company expand to an Inglewood location, was made alongside a few others, including the prosecco brand Viarae, a partnership with California-based E. & J. Gallo Winery, and the hair care company Sienna Naturals, which she founded with her sister-in-law Hannah Diop.

Rae tells BI that her foray into fine jewelry was, in part, due to her desire to embrace her femininity as she's a "very casual girly."

"As my career started to evolve, jewelry was a symbol of showing up," she said.

"It became my armor in a way. I'm braving myself for the day," Rae continued. "Even though I don't feel luxurious, even though I don't feel like I'm worthy to show up here, what I'm wearing makes it seem like I am."

Rae said the Braeve Collection, her collaboration with Cast, a San Francisco-based jewelry company, had to be approachable for it to make sense. The 22-piece collection, ranging in price from $250 to $5,900, features a variety of geometric hoops, cuffs, rings, necklaces, and pendants in finishes ranging from sterling silver to 14K gold.

The actor said she hoped the price range "was right in the middle for the girl who's just like, 'I deserve. I wanna treat myself. I'm ready to level up,' and that's — across the board — the girl I want to approach, the girl that I'm talking to in my work."

For an entrepreneur with her hand in many pots, I wanted to understand the mindset that propels Rae in business — to what she credits her success, the red flags she looks out for in entrepreneurship, and how she can create so effectively. Here's what she said.

Rae credits this one skill to her success

The 39-year-old writer said waking up at 4 a.m. is her cheat code.

"I started by saying I'm gonna get up at 7 today; I'm going to get up at 6, and then it became 4 — and 4 has been a game changer, honestly. Nobody else is up," she continued. "So much of the pressure is I'm always behind, and it was the first time I felt like I'm not behind anymore, and I get my own self-care time in."

Rae also noted that she didn't have any other time that was her own, "so now it's become the only part of my day that I could fully control."

She uses it to work out, which she considers her own form of active meditation, in her garage gym. She then journals.

"I'm waking up for me and not for other people."

The actor says a creative's first hire should be a TV producer

When you look at a successful actor, there are so many people standing behind, beside, and in front of them who make their achievements possible. Rae said when building her team, her first hire was her most essential.

"When I first met Deniese, that's all she wanted to do was produce. That changed the game for me because that's a person who's just interested in executing and making things happen, pulling the people together to make your ideas happen," she explained, referring to producer Deniese Davis.

Davis produced Rae's hit shows, "Awkward Black Girl" and "Insecure." She's also the cofounder of the management company ColorCreative, which she created with Rae and producer Talitha Watkins in 2014 to support women and minority writers.

"I say, 'I wanna do this project, and she's like, 'Cool. This is how we make this happen' because I can't do it myself — the 'how' person, the 'these-are-the-steps' person. To someone else outside the entertainment industry, maybe that's a project manager."

Rae's biggest red flag when it comes to participating in collaborations is based on honesty

Even though Rae has signed onto many collaborations and partnerships, she's also learned when to say no.

"When they're just solely driven by money, and if I feel like I can't be fully honest in the criticism aspect, and they can't be honest with me, I'm like, 'Oh, this won't work,'" she detailed.

"I need to know you think my ideas suck, and I need to be able to tell you your ideas suck, and we need to be able to not feel a way about that to make it the best it can be," Rae explained.

"A red flag is just the sensitivity; you can always tell when people aren't being honest with you."

The actor broke down her formula for peak creativity

Having created so many shows that have gained cult-like audiences, from "Insecure" to "The Sweet Life," a reality show following Gen Z creatives in LA, to "Rap Sh!t," a series about two rappers trying to make it big in Miami, Rae seems to know what audiences want to see on the small screen.

Although she's been pretty tight-lipped on the plot details, Time reports Rae is now working on two new shows as part of her WarnerMedia partnership.

She told Business Insider that to write and craft TV shows that speak authentically to her audiences, she has to leave the confines of her home for at least 72 hours.

"I can't fully dream in my home. I always have to leave, and sometimes I will…it really is just a logistical thing," she began. "I need three days in a row to be able to start to be creative. I've discovered that's my formula."

"The first day will always be spent procrastinating or finding things wrong and reasons I can't start, and I need to allow for that day," Rae added. "The second day, I feel bad for the first day."

She said she isn't concerned about her first two days because "in procrastination, you're still thinking; it's still in the back of your mind."

"Ideas are still gestating, so by that second day, you're ready, and by the third day, it's like, 'This is all I have, so I have to get it down,'" she continued. "So, I recognize the perfect amount of time is three days, and by that third day, I'm off."