Female Owner Of Start Up Coffee Shop Or Restaurant Turning Round Open Sign On Doorgetty
When Keith Lee reviews a restaurant, lines wrap around the block, and sales soar—yet that kind of overnight success can come with a hidden cost: burnout. Mental health issues are common among entrepreneurs and can lend to a fear of growth. A July 2025 Founders Reports survey found that 87.7% of entrepreneurs struggle with at least one mental health issue. For many Black millennial entrepreneurs, that tension between scaling and burning out is especially acute.

The data underscores how precarious growth can feel. Roughly 20 percent of new U.S. businesses fail in their first year, and nearly half close within five years. By the 10-year mark, about two-thirds have shuttered, leaving only a third that survive the decade. For restaurants, the picture is slightly better than the myth suggests: contrary to the belief that 90 percent close in year one, research shows only about 17 percent fail in their first year, a rate lower than many service industries. These realities explain why rapid success can feel as frightening as it is rewarding.

As the Harvard Business Review (HBR) explains, learning is a remedy for the fear of failure. According to the outlet’s research findings, uncertainty and ambiguity are hallmarks of entrepreneurship.

The Keith Lee Effect…And Its Challenges

As a food critic and creator, Lee has built a reputation for transforming small restaurants into local landmarks with a single viral TikTok. But he’s also deeply aware of the burden success can place on founders. “It could be scary,” Lee told me. “You don’t know what you don’t know. Especially as an entrepreneur, you don’t really get a lot of grace—particularly as a Black entrepreneur. People don’t always look at the people behind the food, just the food and the service.”
That’s one of the reasons Lee partnered with Microsoft on The Reheat, a multi-platform video series now in its second season. This year’s focus goes beyond visibility. It’s about giving entrepreneurs practical tools to manage their success and their lives. Microsoft’s AI assistant, Copilot, helps owners streamline scheduling, reporting, and even market research, freeing up their most valuable resource: time. “Season 2 is about showing that success doesn’t have to mean sacrificing what matters most,” Lee said.

From Overwhelmed to Empowered
Few understand this balance better than Kristen Harper, owner of Cleo’s Southern Cuisine in Chicago. After Lee’s first visit in 2023, Cleo’s saw its sales triple in a single month. The rush was exhilarating—but daunting.Keith Lee, Kristen HarperKeith Lee, Kristen Harper

“As entrepreneurs, especially being a Black woman, you have a vision in your mind on where you want your business to be, which is great,” Harper told me. “But when those things actually start happening, it is scary. I was just jotting things down on my vision board, and now I’m having conversations with huge companies.”
For Harper, AI tools became a quiet but powerful ally. She leaned on them, not only to manage logistics across her growing three-location enterprise but also to build confidence in her leadership. “Sometimes, as the business owner, you don’t have the confidence you want because you don’t have all the experience. Now, instead of always trying to find a mentor, I can use AI tools. I can ask them questions in real time and make decisions faster,” she said.
Much like Harper, Jameel Rainey was cognizant of what it would take to scale his event production company, Meel Ticket Entertainment, if he wasn’t ready. Despite only being a few years old, it’s already amassed a solid following and has serviced high-profile clients. When planning for the years ahead, Rainey said he couldn’t envision beyond what was in front of him.
“We want to expand, but I want to make sure I have the proper resources and reserves to support the growth. I don’t want my unique event ideas stolen by hurriedly hiring the wrong people to help bear the workload, for instance.” To quell these fears, he leans into AI-powered tools like the ticketing platform Eventnoire to optimize demographic analysis and use predictive data plan things like event times and locations.
Much like Rainey, Harper ensured she took practical steps to scale without compromising her family recipes or her peace of mind. She partnered with a co-packer to produce Cleo’s signature blends—chicken fry, seafood fry, and even mac and cheese—in bulk. “You become afraid to share those recipes with your team, especially when you’re growing,” she explained. “But co-packing eliminates that fear, ensures consistency, and frees me to focus on building my team and expanding strategically.”
A New Model of Success
Lee echoes that sentiment. His mission has never been about celebrity—it’s about amplifying everyday entrepreneurs. “I always consider myself a vessel. The platform has never been about me. It’s always been about businesses, people, and community,” he said.
For millennial founders of color, the statistics on business failure are sobering. But Harper’s story and Lee’s mission show that growth doesn’t have to be a source of fear. With new tools, intentional planning, and community-centered partnerships, scaling can be redefined—not as a burden, but as a sustainable path to legacy.




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