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Ex-Olympian Couple Leap Into VC: 7 Celebrity Brands Already Backed, Including Issa Rae’s Haircare Line

Former Olympians Samyr Laine and Ayanna Alexander-Laine launched Freedom Trail Capital in 2023, and now they’re aiming for a $50 million fund to invest in consumer brands. The couple, who competed in the triple jump for Haiti and Trinidad and Tobago, respectively, revealed in an interview with TechCrunch on Tuesday that they have already invested in seven startups with its initial fund.

Notable investments include Sienna Naturals, a hair care company by Issa Rae; Oh Norman!, a pet product company started by Kaley Cuoco; Ciara’s Ten to One Rum; and Kudos, a diaper company backed by Mark Cuban and Gwyneth Paltrow. Laine reports that seven more investments are in the pipeline as they continue to raise capital.

Laine brings experience from his roles as SVP of Operations and Strategy at Westbrook, the venture firm founded by Will Smith and Jada Pinkett Smith, and Director of Operations at Roc Nation, working with Jay-Z. Alexander-Laine is pursuing a doctorate in business administration, focusing on healthcare finance and inequities.

Freedom Trail Capital’s investment thesis centers on talent-led businesses. In the interview, Laine emphasized the importance of product-market fit and a strong connection between the celebrity and the product, noting that successful celebrity-backed brands require more than endorsements. “We’re talking about you owning a significant part of this company,” he told TechCrunch.

The firm’s approach to due diligence and portfolio support stems from Laine’s operational background. “Having been at a place where I know what it takes for these brands to win, we’re looking at our portfolio very differently than most people,” he said in the interview.

Laine was Mark Zuckerberg’s college roommate at Harvard and competed in the 2012 London Olympics. He advises aspiring entrepreneurs to “go do the thing you won’t be able to do,” drawing from his own experience of balancing law school with Olympic training.

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David Adler is an entrepreneur and freelance blog post writer who enjoys writing about business, entrepreneurship, travel and the influencer marketing space.

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