How Issa Rae Builds Businesses That Convert Customers Into Community

Issa Rae–actor, writer, producer, and small-business owner–is a multi-hyphenate to a T. But she likes to think of herself as a builder.

And what she’s most interested in building is a community–through a wide range of vehicles, including her many businesses. In Rae’s appearance in American Express’s Business Class video series, which spotlights entrepreneurs and their operational insights, she shares the strategies that helped her grow Hilltop Coffee + Kitchen, the Inglewood, California, coffee shop that she owns with co-founders Yonnie Hagos and Ajay Relan, as well as her hair care brand Sienna Naturals, her record label Radio, and her production company Hooray Media. As varied as her companies may be, they’re each built with the same underlying principles.

In a conversation with Inc., Rae expanded on her advice and shared her best practices for fostering community and building businesses that thrive.

Seek advice; get organized

Rae briefly worked in the corporate and nonprofit worlds before the 2016 debut of her HBO show Insecure, but she acknowledges that building and owning a company is much different from working at one. So she overcame some initial, well, insecurity and sought mentorship to help her navigate the business world. “I do have a complex around asking for help,” she says. “I don’t think it had occurred to me that I could turn to friends and resources to ask for advice.”

But by turning to business owner friends, she says she’s learned about the importance of good organizational infrastructure–especially as it pertains to hiring and job development. “I’ve asked how people approach their hires–what it took to hire people to solve certain problems,” she says. While different businesses may have different infrastructures–a coffee business will inevitably look different from a production company–Rae says that friends and mentors have helped her figure out the key staffing needs that make her businesses successful. 

Start two-way conversations

Hiring, as all entrepreneurs know, is just one part of the talent equation: Retention is just as–if not more–important. That’s why, when hiring, Rae likes to get an idea of a candidate’s career goals. “I am really looking to grow with people and help them reach their long-term goals,” she says. “But even if the company is just a stepping stone, that’s helpful to know in advance.”

Rae fosters a sense of community at her production company with activities like “Come Through Fridays,” where invited guests talk to and meet employees, and large brainstorming sessions that allow everyone at the company to be heard. “That’s been extremely powerful, to hear from literally everyone and take action steps toward making those particular ideas a reality,” says Rae.

Community building is just as important when it comes to customers, she adds, and it involves having two-way conversations. “There’s definitely a difference between audience and community,” Rae says. “Community is more concerned with repeat investment on both sides. Input from the community is essential. Community helps make businesses and brands long term, it helps establish a legacy.”

Think big picture

How do you build a veritable media empire that lands you a $40 million deal with Warner Media? It’s all about laying the right foundation. “What’s crucial to building something is vision,” Rae says. “I loved Lego sets when I was younger. But there was a difference in how I played with Legos when I was really young, versus when I was a slightly older kid. Initially, I was just putting blocks together and seeing what shape I could make. Later, it came down to, ‘Oh, I’m making a house’ — and then it got more intricate the more thought I put into it.”