Kai Cunningham of Limited Ventures: Bridging the Gap Between VC and Pro Athletes + Entertainers
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In today’s episode, I sit down with the awesome Kai Cunningham, General Partner at Limited Ventures. Kai has a fascinating story, coming from humble beginnings in the DMV to “scrapping it” on midnight busses, friend’s couches, and more to hustle into an internship at Goldman Sachs. He was networking his tail off to break his way into finance, pitching folks in Wall Street elevators and more.
After a stint in NYC and LA, Kai helped found Limited Ventures to connect two quite different worlds of wealth: The old guard (The Rockefeller, Forbes, & Costa Families) with the New Guard — Pro Athletes, Entertainers, Artists, and Influencers.
Limited Ventures is a fund created alongside the Forbes, Rockefeller, & Costa families, and counts numerous athletes and entertainers as LPs (as well as traditional LPs).
Kai serves two critical roles:
- Helping family foundations + institutions satisfy their Diversity and Inclusion mandates without sacrificing returns
- Bridging the gap between athletes/entertainers and the billionaire families of the world
He has helped over 100 athletes and entertainers participate in deals like Airbnb, SpaceX, Lime, Coinbase, Pinterest, Lyft, DapperLabs, Zilch, Kraken, and many more.
Some highlights below:
Kai’s Journey from Baltimore to Wall Street
“I always tell people, the best thing that happened to me was realizing that I wasn’t going to be a professional athlete…I had a large number of friends that were starting to play professionally at the same time that I went to Wall Street.
So leading up to Wall Street…it was always in the back of my mind, how am I going to merge the two?”
“I started building my own process. Because for me, it was always about how do I differentiate myself from the kids at Harvard and Wharton and Yale with 4.0’s. I was just building relationships with people…I had collected a database and had notes from every conversation, and ended up connecting with 65+ people who all vouched for me, and that was just to get the internship.”
Limited Ventures
“We decided to build a fund around this concept of bridging the gap between athletes/entertainers and the billionaire families of the world, specifically how they invest. So at the core of the fund, even though we have athletes, most of the capital does come from more traditional LPs. But what we like to do is integrate the athletes and entertainers into our investment process, educate them along the way, and then help provide additional value.”
“Unfortunately for the culture, but fortunately for me, there are very few people who can sit in between both of those two parties [old-money billionaires + modern athletes] and essentially serve as a cultural translator.”
The Untapped Opportunity in Athlete Investors
“Where we look is the bottom 99% of the NBA, NFL MLB, NHL, even golf. Those guys, particularly in the NBA, are going to make $10 to $20 million as the eighth or ninth man on the team. So it’s about providing access to that guy, because he may be LeBron James in his hometown to all the kids that look up to him.”
Athletes, Investing, And Setting a New Culture
“Now, I not only see LeBron James as a basketball player, but I see him as a venture capitalist, a film producer, an entrepreneur, a real estate investor. We can change the narrative of not just the top 1% of athletes and entertainers, but the entirety of the league. That’s going to trickle down to the kid growing up in the inner city of Baltimore, to where he doesn’t only see the options as playing basketball or making music. Now he sees an entrepreneur a business owner, a real estate investor, or a professor like Brandon*.”
*Brandon Copeland is a Penn Professor, serial investor, real estate developer, and current Atlanta Falcon! Brandon came on Wharton Fintech earlier this year for an incredible episode about financial literacy and the modern athlete.
What Fintechs (and all companies) Need to Know When Partnering with the Modern Athlete
“You said the word a number of times, “partner.” You need to have a true partnership. And I think the only way to do that is to be completely aligned, which is through equity. If I’m an owner, I’m incentivized to be a little bit more proactive. The days of, not even just for FinTech, but just for companies working with athletes: Cash deals are over! It’s about, how do I become an owner?”
Kai’s Take on The New Wave of Corporate Investment in DE&I
“There’s been over $35 billion committed or earmarked to diversity and inclusion, while less than 2% of that has actually been deployed…it’s about being able to execute these mandates for diversity and inclusion without having to sacrifice returns.”
“I want to be the diversity and inclusion investment for these institutions, family foundations, endowments, etc. I can go execute my thesis as is, and then donate a percentage of the carry and a percentage of the profits to nonprofit organizations or other institutions. I feel like most of the industry is trying to tackle this problem by just throwing capital at Black founders or female founders…How do we empower the entire ecosystem? How do we put capital with women or Latin or Black fund managers who inherently have these deeper and more direct connections to the next big company from their community?”
We cover a lot more in this episode including his investment in UK BNPL Zilch, the Limited Ventures thesis, fintech trends he’s following, a fun rapid-fire round, and much more!
Some quotes have been lightly edited for clarity.
Listen on Apple | Spotify | Soundcloud
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Previous Episodes You May Enjoy:
Y Combinator’s Michael Seibel & Dalton Caldwell — Lessons from 5000 Entrepreneurs
Jarrid Tingle, Managing Partner of Harlem Capital — Transforming the Face of Entrepreneurship
NFL Star & Penn Professor Brandon Copeland — Tackling Financial Education Through “Life 101”
Former Vanguard CEO & Chairman Bill McNabb: The Future of Finance, Leading in Crisis, & ESG
Jeff Immelt, Former GE CEO — Globalization, Crisis Leadership, & 16 Years at The Top
Mayor Francis Suarez — Bringing Silicon Valley to Miami!
Republic Founder Kendrick Nguyen: Empowering 1 Million People with Private Investing!
Billionaire Investor, Activist, & Educator Tim Draper — China, Bitcoin, and Free Societies
Michael Sidgmore, Partner at Broadhaven Ventures: Why Alts Are Going Mainstream!
Empowering Black Millenials with Ras Asan, Co-Founder of BREAUX Capital
Brianne Kimmel, Founder of Worklife Ventures — 6 Unicorns, Solo Capitalists, & the Future of Work!
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Ryan Zauk
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Ryan Zauk is a recent MBA graduate of The Wharton School, where he led the Wharton FinTech Podcast. He currently works with the US International Development Finance Corp looking at technology impact investments in developing markets. He will be joining Morgan Stanley’s Fintech & Technology team in Menlo Park after graduation. He has a passion for music, media, and all things FinTech.
You can reach him at rzauk@wharton.upenn.edu or on Twitter.
