My All-Athlete Investment Team: The Top Tier

Darren Douglas
4 min readOct 24, 2021
Cline-Thomas (left) and Iguodala PHOTOGRAPHER: MICHAEL FRIBERG FOR BLOOMBERG BUSINESSWEEK

From playing basketball to developing software to operating a startup, the winding road that is my young career has led me to the exclusive industry of Venture Capital. I started in the startup ecosystem of in Philadelphia, then New York, and now currently in Los Angeles. Despite the many differences between these cities, one thing they all share is a passion for sports — with all four major sports represented (Basketball, Football, Baseball, and Hockey).

Since reading Mark Cuban’s “How to Win at the Sport of Business”, I haven’t been able to ignore the parallels between the two fields. Cuban highlights in the first chapter how important it is to be a dreamer. The best athletes have to have almost irrational confidence in themselves to believe he or she will be the one in a million to make it to the big leagues. Similarly, the best entrepreneurs must have unwavering faith in their abilities to believe their company can outpace the competition and become a unicorn.

I’m a dreamer too. While VC has traditionally been a tough industry to break into, people like Rashaun Williams of Manhattan Venture Partners are leading the charge in exposing athletes to startup investing. That said, he shouldn’t have to do it alone. When it comes to improving diversity in Venture, athletes need to be included in the conversation. They already have the capital, but they need to access and education. With quality deal flow and industry knowledge, they can best leverage their platform.

It’s frequently discussed how many athletes squander their fortunes after their playing careers, so I wanted to highlight a different theme. Decades ago, athletes focused their investments on car dealerships, franchising, and real estate, but now they are finally getting outside of that scope. As such, I want to highlight the best athletes turned startup investors.

To determine who makes the cut, my 3 key factors were:

  • Total capital deployed
  • Number of exits
  • Market Cap of Portfolio Companies

With that, I present you the Top Tier.

Andre Iguodala

Of all active pro athletes, one could claim that Andre Iguodala has the most formal business résumé of anyone. He’s been in the pitch room at Andreessen Horowitz, served on numerous boards, and advocated for athletes to take on riskier and more lucrative investments. Along with his investment partner, Rudy Cline-Thomas, he focuses his investments in the direct-to-consumer space. A few highlights in his portfolio include Dapper Labs, Casper, Allbirds, and Walker and Company Brands.

Serena Williams

Founded in 2014, Serena Ventures invests in companies that embrace diverse leadership, individual empowerment, creativity, and opportunity. Not only does she benefit from being recognized as the best athlete of all time, but she also benefits from being married to one of the best internet entrepreneurs in Alexis Ohanian. The combination of her personal brand, valuable network, and investment thesis has led her portfolio companies to have a market cap of over $33B. A few standouts are Daily Harvest, Impossible Foods, Masterclass, and Andela.

Joe Montana

Joe Montana is the Founder and Managing Partner of Liquid 2 Ventures (L2V), a seed-stage firm based in the San Francisco Bay Area. They’ve invested in over 10 unicorns including companies such as Gitlab, Rappi, Anduril, Retool, and many others all from the earliest stages.

Kevin Durant

Known for being the most unguardable basketball player of all time, Kevin Durant has been making moves off the court as well. Durant is co-founder and partner of Thirty Five Ventures with an investment portfolio that spans more than 75+ companies across a variety of verticals and growth markets, including fintech, cryptocurrency, health and wellness, media, & more. With deep relationships in venture capital and private equity, his team works strategically with a subset of partners on strategy, content and marketing initiatives. Some of their most successful portfolio companies include Postmates, Overtime, Coinbase, and Acorns.

Thaddeus Young

Drafted by the Philadelphia 76ers in 2007 and still active, Thaddeus Young has had an NBA Career longer than most. And while he isn’t as well known as the rest of the athletes on the list, his investment track record is too good to ignore. He founded Reform Ventures, a private investment fund that evaluates and provides value-added investment in early, growth, and late-stage companies. A few highlights in his firm’s portfolio include Airbnb, Pinterest, Epic Games, Lyft, and Tonal.

I believe these athletes are the trailblazers. They are the ones setting the foundation for the next wave of athletes turned investors.

I also understand this is not an exhaustive list, so who did I miss?

My VC Journey is far from over, and I’ll continue to share my learnings. If you want to stay in the loop, follow here in Medium and on Twitter @darrensvision

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