Inside Issa Rae’s Portfolio of Creative Ventures and Local Small Businesses

From Insecure on HBO to The Lovebirds on Netflix, Issa Rae has primarily been known as an actress, writer, producer, and comedian. The Emmy award–nominated A Black Lady Sketch Show, the docuseries Sweet Life, and the upcoming HBOMax series Rap Sh*t, are just some of the projects she's currently working on.

But somehow, the multi-hyphenate also fits serial entrepreneurship into the mix—with a focus on local small businesses. Rae backs or co-owns Hilltop Coffee + Kitchen, a hub for creatives with several locations in the Los Angeles area; Sienna Naturals, a vegan hair care line rooted in sustainability; and HOORAE, an umbrella media company that houses film, tv, digital, music, and management divisions.

And she intends to empower and gather other Black entrepreneurs along the way. Rae has teamed up with American Express to promote ByBlack, the first nationwide certification program for Black ownership. ByBlack was founded to help elevate Black businesses and create meaningful opportunities for the Black community,  including business certification, educational programs, grants and funding, and more.

“I registered my businesses with it," says Rae. "It’s an opportunity to have my businesses officially certified by an accredited organization.” She also stars in American Express Business Class, a free series of educational videos highlighting business concepts and common hurdles that rookie entrepreneurs often face.

While many celebrity entrepreneurs attach themselves to global corporations and venture-backed startups, Rae is proud to focus on small businesses. “I am very local. I love brick and mortars. I tend to focus on places I love to be at, or products that I use—it’s very self-centered in a way,” she says, laughing. “I think about the void I need to fill and tackle that. But it’s not about what’s sexy or popular, but a genuine need and an appreciation for a business.”

Hilltop was first founded by Ajay Relan and Yonnie Hagos in 2017. When they expanded to Inglewood—Rae's home neighborhood—in 2018, she got involved. Now, she's excited to bring Hilltop Coffee to Los Angeles International Airport. The cafe will be opening in the coming months in the United Airlines terminal. “It’s really hard to get businesses in LAX so to be able to have placement there alongside Randy's Donuts, which is so iconic for Inglewood, establishes us in a real way,” says Rae.

She also made sure Hoorae was headquartered near her hometown. “It was a big deal to purchase property in South L.A., and our ultimate goal is to have a studio and that is in the works.” Rae adds: “I have such a love for where I come from and my city, and I also just approach my business ventures with my lifestyle in mind.”

Building businesses that fit with her lifestyle is one of the reasons her portfolio includes clean beauty and wellness. This time, it’s a family business. In 2020, Rae teamed up with her sister-in-law Hannah Diop to launch Sienna Naturals. She credits Diop as the brains behind the original formulas, but she’s proud to have a hand in creating the next collection of products. “I had a very big part in influencing the general development and testing of it.”

And although Hoorae, her production house, is a multi-faceted company, Rae says she’s extremely strategic about the direction of the venture by staying lean and keeping an eye on all resources—especially human resources. “For so many companies, the first instinct is to go big and go on a rapid hiring spree," says Rae. “With Hoorae we’ve been really intentional about our growth. I, personally, have been very clear that I wear many hats and there’s always an opportunity for others to maximize their potential. It’s an environment where people can help us be cost efficient.”

“Growing and scaling your business can take on so many meanings and come with so much pressure to move fast," says Rae. "But it’s important to move at your own pace.” Sage advice from a local mogul.

Correction: A previous version of this article mistakenly said that Issa Rae created ByBlack.