Kai Cunningham ’16 VSB finds professional success combining Venture Capital, sports and the Villanova network

Kai Cunningham ’16 VSB found a top ranked undergraduate business program, mentorship, and a deep love of sports at Villanova. Less than five years later, he is using his Villanova experiences to help carve his own professional path as a co-founder and general partner at Limited Ventures, an invite-only $150 million venture firm dedicated to bridging the gap between affluent families and individuals to professional athletes and entertainers looking to learn about and invest in private tech companies.

As Cunningham began his career on the trading floor at Goldman Sachs in New York City, he saw his childhood and college friends signing professional sports contracts. In his free time, he found himself providing guidance on the financial world to his friends and peers. He eventually transitioned across the country to Goldman Sachs’ Private Wealth Management division in Los Angeles.

What originally started as helpful advice to friends, turned into opportunities to assist athletes and entertainers into monetizing their influence and likeness beyond the basketball court, football field or stage. Cunningham recognized the demand and started looking at Venture Capital deals with the same group of athletes that originally reached out for financial literacy.

“Venture Capital is a unique asset class that most are still learning about,” he said. “Along the way, we educate both sides (family offices/high net worth individuals and athletes/entertainers) on how to integrate the culture into investing through workshops and our venture curriculum as we build relationships with the founding teams of companies we invest in.”

Cunningham and his partners have guided over 200 athletes and entertainers in early, growth, and late-stage investments. They work to directly integrate and educate an athlete or entertainers’ ecosystem of financial advisors, agents, business managers and family members into their investment process by getting the influencers marketing deals in the form of equity and cash as well as carving out special allocations to help them co-invest in deals.

“The Forbes family and Rockefeller family, who are the epitome of generational wealth, are my partners in the fund,” Cunningham said. “We bring that level of access and expertise to our investor base of CEOs, high net worth individuals, family offices, artists, athletes, entertainers and influencers.”

Cunningham’s love of the sports world runs deep as he played on teams with dozens of future pro-athletes.

“I knew that education was my ticket,” Cunningham said. “I was actually accepted into a program called the Wharton Sports Business Initiative the summer before my senior year in high school. From that experience, I knew that I wanted to go to a school with great academics and great athletics.”

His acceptance into the Villanova School of Business helped blossom ideas, mentors, and relationships that would spark a professional career in wealth management and venture capital.

While in school, he landed his first internship with James C. Davis ’81 VSB, co-founder and chairman of Allegis Group, an international talent management firm. Cunningham also developed connections with members of Villanova’s 2016 national championship men’s basketball team. His close friend Daniel Ochefu ’16 CLAS, a member of the national championship team, set up a meeting between Cunningham and Jay Wright, William B. Finneran Endowed Head Coach of the Men’s Basketball team. After Cunningham shared his experiences and aspirations, Coach Wright wanted to help in any way that he could.

“During one of my shadow days at Goldman Sachs, I randomly received an email that included Coach Wright, James C. Davis and Justin Gmelich ‘90 VSB, one of the top partners at the firm, and the rest is history,” Cunningham said. “I still rely on their guidance and mentorship to this day.”

Cunningham discovered that the interactions between students-athletes and the alumni base at Villanova reflected how he wanted to build and foster meaningful relationships between his clients and the families that invest in his fund.

“If you meet another Wildcat, you are automatically treated like family,” Cunningham said. “My goal is to help other members of the Villanova community, past and present, understand and invest in venture capital.”