Issa Rae reveals the skills that have made her profitable, red flags in business

I had never been to Inglewood, but it looked familiar. After following the sunny city set in southwest Los Angeles for five seasons of Issa Rae’s award-winning series Insecure, I’ve come to know some of the city’s landmarks.

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

I stepped out of Uber Comfort in front of Hilltop Coffee and Kitchen, a black-owned restaurant co-owned by Rae, who was also featured in season four, episode two of “Insecure,” a series documenting Dee’s uncomfortable experiences as woman in her twenties. trying to find his place. Inside, the smell of freshly brewed espresso drinks wafted through the air as I tried to decide what to 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 the length of the bar.

Hilltop is just one of the many businesses that Rae has authentically made her mark in recent years. Rae said coffee shops are where he is most innovative.

“I’m a cafe girl,” the LA native told Business Insider in September during New York Fashion Week. “I like to people watch.”

Multicrava was promoting another venture, her new collaboration with Cast Jewelry, when I sat down with her at the elegant Howard 11 Hotel. We discussed her take on fine jewelry on a picturesque rooftop terrace in SoHo—far from where her Left Coast career began in Los Angeles.

Rae came of age online, particularly YouTube, during the Gold Rush. Around the 2010s, it seemed like 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 them in a way that “Star Search” could never allow for that level of intimacy. I thought Rae was a friend in our group discussions, and in some cases she was. Before the baby boomers took over Facebook, Rae befriended many of us, appearing on our timelines just as one of our friends, populating her feed with her own life updates, just like the kid in science class we’re talking to rarely with 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 several roles in films such as “The Hate U Give”, “American Fiction” and “Barbie”.

Despite staying busy on screen, behind the camera Rae looked 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 struck a $40 million deal with WarnerMedia, ensuring that 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 several others, including prosecco brand Viarae, a partnership with California-based E. & J. Gallo Winery and 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 girl.”

“As my career began to evolve, jewelry was a symbol of emergence,” she said.

“It’s become my armor in a way. I’m facing that day,” Rae continued. “Even if I don’t feel luxurious, even if I don’t feel worthy to appear here, what I’m wearing makes me look like I am.”

I need three days in a row to be able to… be creative. I found this to be my formula.

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

The actor said he hopes the price range “is right in the middle for the girl who says, ‘Mrit. I want to treat myself. I’m ready to level up’ and that’s – generally – the girl I want. to get closer to the girl I’m talking to in my work.”

For a multi-tasking entrepreneur, I wanted to understand the mindset that drives Rae in business—what she attributes her success to, the red flags she looks for in entrepreneurship, and how she can create so effectively. Here’s what she said.

Rae credits this ability with her success

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

“I started by saying I’m going to get up at 7 today; I’m going to get up at 6, then it became 4 – and 4 was a game-changer, honestly. Nobody else gets up,” she continued. “So much of the pressure is that I’m always behind and it was the first time I felt like I wasn’t behind and I was making my own care time.”

Rae also noted that she didn’t have any other time that was hers, “so now it became the only part of the day that I could fully control.”

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

“I wake up for myself and not for other people.”

The actor says a creative’s first job 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 that make their achievements possible. Rae said that when building her team, her first hire was the most pivotal.

“When I first met Denise, all she wanted to do was produce. That was a game changer for me because this is a person who is just interested in executing and making things happen, bringing people together to make your ideas happen,” she explained. referring to producer Denise Davis.

Davis produced Rae’s hit series Awkward Black Girl and Insecure. She is also the co-founder of management company ColorCreative, which she co-founded with Rae and producer Talitha Watkins in 2014 to support women and minority writers.

“I say, ‘I want to do this project,’ and she says, ‘Okay. This is how we make it happen’, because I can’t do it – the ‘how’, ‘these-are-the-steps’ person. To someone else outside of the entertainment industry, maybe it’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 many collaborations and partnerships, she has also learned when to say no.

“When they’re just driven by money and if I feel like I can’t be completely honest about the criticism and I can’t be honest with myself, I’m like, ‘Oh, that’s not going to happen. of work'”, she detailed.

“I need to know that you think my ideas are shit, and I need to be able to tell you your ideas are shit, and we need to be able to not feel any of that to make it the best it can be,” Rae explained. .

“A red flag is just sensitivity; you can always tell when people are not being honest with you.”

The actor broke down his formula for peak creativity

Having created so many shows that have gained cult followings, from ‘Insecure’ to ‘The Sweet Life’, a reality TV show following Gen Z commercials 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.

While she’s been tight-lipped about plot details, Time reports that Rae is now working on two new shows as part of her partnership with WarnerMedia.

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

“I can’t fully dream in my house. I always have to leave, and sometimes I will… it’s really just a logistical thing,” she began. “I need three days in a row before I can start being creative. I’ve found that’s my formula.”

“The first day will always be spent procrastinating or finding things wrong and reasons why I can’t start, and I have to allow for that day,” Rae added. “The next day, I feel bad for the first day.”

She said she’s not worried about the first two days because “in procrastination, you’re still thinking; it’s still on your mind.”

“The ideas are still in gestation, so by day two, you’re done, and by day three, it’s like, ‘This is all I’ve got, so I’ve got to get it down,'” she continued. “So I recognize that the perfect amount of time is three days, and by the third day, I’m gone.”