In seventh grade, Kai Cunningham stepped onto those sprawling estates of his private school classmates and realized he was playing an entirely different game. Well actually, he wasn’t really even in the game at all.
His Baltimore neighborhood was a stark contrast to his classmates’ multimillion-dollar homes, altering his entire perception of what “making it” it looked like. So he got curious. While their fathers ran private equity firms and hospitals, Cunningham began asking the questions that would shape his future: “What do your parents do? What does it mean to own a building or a company?”
Fast forward to today, at just 30, and Cunningham’s curiosity has paid off. Those early observations (and of course his intellect and charm — which I experienced firsthand in just a 40 minute Zoom conversation) have now morphed into Limited Ventures, an investment firm he co-founded with members of the Rockefeller and Costa families. From that unlikely starting point, he’s now deployed over $100 million into startups spanning fintech, food tech, and immersive sports experiences, with a strategic focus on Black entrepreneurs reshaping the cultural economy.
For Cunningham, his investment thesis is a combination of “proximity, purpose, and power,” which essentially just means building connections across historically separate worlds, with capital serving as the bridge.
“I sit at the nexus between billionaire families who’ve passed wealth down for generations and Black athletes and entertainers who’ve gone from zero to a hundred,” he tells ESSENCE. “And when you put those two groups in the same room with a shared investment opportunity, that’s when one plus one equals fifty.”
But let’s rewind a bit. It took a whole lot of grit and hustle to get to where Cunningham is today. Sprinkle that in with a little bit of lucky boy syndrome, and you’ve got the holy trifecta. Take for a example, a chance connection at Villanova (School of Business) — his alma mater — with Jim Davis, co-founder and chairman of Allegis Group, an international talent management firm, who later funded his education and opened doors to corporate opportunities, like his first internship. Then later at Goldman Sachs, Cunningham helped manage a $2 billion division, where he quickly recognized that barriers weren’t about talent, but about translation.
“My counterparts had parents who ran divisions at the firm. They’d been speaking this language since birth,” he explained. “For people like me, it’s like learning a new language as an adult. And on top of that, I was being asked to bring my relationships—my friends, who are athletes and entertainers—to the table without being compensated because I wasn’t ‘senior enough.’ That didn’t sit right with me.”
Eventually, Cunningham left Wall Street to build something uniquely his own—a platform aligning cultural influence with long-term financial strategy. Limited Ventures is actively redefining what a Black family office can become.
“We live in the gray,” he says. “We’re not agents. We’re not business managers. We’re not financial advisors. But we provide pieces of all those services in a way that keeps everyone accountable and aligned.”
Today, his network includes nearly 100 professional athletes and entertainers who co-invest alongside him, including Lil Wayne, Breanna Stewart, Marcedes Lewis, and Danny Green. They’ve backed companies like Eastside Golf – a streetwear-meets-golf lifestyle brand founded by two Morehouse grads that has partnered with Jordan Brand and Mercedes-Benz; StatusPRO – a VR sports tech company using athlete data to create immersive gaming experiences where Cunningham serves on the board; and BAGS – a fintech startup founded by Daniel Taylor that helps emerging consumer brands with capital access, accounting tools, and debt strategy.
“These aren’t just great businesses with Black founders,” Cunningham says. “They’re great businesses—period. And through Limited Ventures, I’ve been able to align athletes and tastemakers with these founders in a way that’s natural, strategic, and built to last. Culture isn’t just the backdrop—it’s the engine.”
That principle stems from a fundamental mindset shift: helping athletes and entertainers recognize that they already possess the discipline to succeed in investing, but they just need the language, tools, and trust. “If you’re in the top 1% of your sport, you already know how to commit to a process. Investing is no different—it’s just a different playbook.”
Yet the stakes continue to rise. “There used to be one guy on a roster making $15 million. Now there are bench players making $25 million a year,” he noted. “The problem isn’t going broke—it’s going broke after making $70 million. That headline hits different. The internal family structure has to be ready.”
That’s why Cunningham focuses on systems, not soundbites. And he rejects a charity approach to investing in Black founders. “They’re not ‘diversity plays.’ They’re world-class businesses led by visionary founders who’ve scaled during one of the toughest venture markets in recent history. My role is to help sharpen that edge—and expand what’s possible.”
He remains clear-eyed about the gaps in venture capital and where structural changes must occur. “We saw a lot of commitments in 2020 and 2021,” he said. “But there hasn’t been a scaled approach to making sure those dollars consistently reach underrepresented founders.”
His solution? Relationship capital. “For entrepreneurs who don’t have access to these rooms, my advice isn’t ‘start investing’—it’s start leveraging your relationships. Your network is more valuable than money, especially when you’re trying to get in the room.”
Cunningham lives this philosophy. His journey from taking $4 Megabus rides to Wall Street meetings in New York to co-owning a horse racing team—the Maryland Colts—with NFL MVP Lamar Jackson exemplifies his approach. “I didn’t have a trust fund. But I had friends in the NBA. We pooled resources. We moved as a unit.”
Yet wealth isn’t his ultimate goal. Impact is. Increasingly, he’s focused on bridging the gap between culture and government, which is territory he sees as ripe for innovation. Recent conversations with Maryland Governor Wes Moore, who grew up in the same community, have opened new possibilities for political partnerships centered on Black families and founders.
“We’ve never had access to wealth creation through government relationships at scale,” he said. “But that’s how a lot of the legacy wealth was built—someone stamps your idea, you get a contract, and now you’re part of a multi-million-dollar deal flow.”
When asked about legacy, Cunningham answers without hesitation. “I want to dismantle the belief that you need to go outside your community to raise capital. I want to build infrastructure that lets us invest in each other, at scale.”
He credits his daughter, now 7, as the driving force behind his clarity. “I lost my father when I was two,” he says. “So when I became a dad at 24, I knew I had to create the life I never had. That’s my North Star.”
And on the difficult days? “Walk by faith and not fear,” he says simply. “I have no fear of failure. Even if something doesn’t work, it was supposed to happen. It’s part of the process.”