Samyr Laine and his wife Ayanna Alexander-Laine founded Freedom Trail Capital in 2023 and are working to raise $50 million.
Both are former Olympians who competed for Haiti and Trinidad and Tobago in the triple jump, respectively. They now use their determination and perseverance to help founders who want to launch and scale consumer brands.
“I love people and connecting with them,” Alexander-Laine told TechCrunch. “We know how to connect talent and business, and we’ve found that athletes are good at those things. We also have the stamina to pursue other things and other entities outside of sports.”
They, along with third general partner Ivan Lopez, have invested in seven startups to date, closing a small first fund. They include Issa Rae’s hair care company Sienna Naturals; a pet products company founded by Kaley Cuoco called Oh Norman!; Ciara’s Ten to One Rum; and Kudos, a diaper company backed by Mark Cuban and Gwyneth Paltrow.
Freedom Trail Capital is still raising capital and has seven more investments planned, Laine told TechCrunch.
To the Olympic Games and beyond
Laine knows what it’s like to start and scale corporations. He previously served as senior vice chairman of operations and strategy at Westbrook, the enterprise capital firm founded by Will Smith and Jada Pinkett Smith. He also hung out as chief operating officer at Roc Nation, working with Jay-Z. In the meantime, Alexander-Laine is pursuing a doctorate in business administration and will focus on healthcare finance and healthcare disparities.
Laine also knows what it’s like to fail. He tried out for the track team in seventh grade but got kicked out the next yr. It wasn’t until his sophomore yr of highschool that he decided to try track again, this time taking the triple jump seriously.
But it was all good. Laine eventually went to Harvard and set several records with the team. He was also Mark Zuckerberg’s roommate. They had a four-person dorm room his freshman yr and even shared bunk beds. Laine ended up being probably the eleventh person to go on Facebook and test it, he said. He was also a quiz query on “Cash Cab” about which Olympian was Zuckerberg’s roommate, Laine said.
“Mark has always been a builder, and we knew he would do something great,” Laine said.
When Laine transferred to the University of Texas, he was introduced to a new world of track and field. His teammates competed at a different level, as many of them were junior world champions. Laine competed in his first Pan American Games in 2007. He also tried out for the Olympics in 2008 and fell a few inches wanting competing in the triple jump.
He was combining training and studying law at Georgetown University when he tried again to make it to the Olympics in 2012 and qualified. Many people told him it was too much, but now when people ask him for advice, he tells them to “do what you can’t do.”
“I thought if I went to law school and balanced that, I could get there,” Laine said. “At that point, I was the seventh-ranked athlete in the world in the triple jump, and going into the London Games, my goal was to win Haiti’s first medal since 1928. I qualified for the finals, but I didn’t end up winning a medal.”
For 10 years, Laine and Alexander-Laine competed around the world as professionals in track and field. Laine learned from his UT teammates how to make money doing it. He also managed to get sponsorships and financial help from the International Olympic Committee.
Work for Will Smith and Jay-Z
He then had a few more careers in sports before moving into entertainment and branding at Roc Nation. Laine worked with Jay-Z to build and scale his brands, which include spirits, apparel, marijuana and book publishing, and even managed several platinum-selling artists. From there, he moved to Westbrook to do similar work for Smith and Pinkett Smith. He was there for 4 years before founding Freedom Trail Capital.
“I didn’t necessarily allocate capital and invest, but I did have some insight into some of the investment decisions that Roc Nation made,” Laine said. “I’m an operator at heart, so that gives me a unique perspective on how we conduct due diligence on investment opportunities and can support our portfolio companies.”
Freedom Trail Capital’s thesis is to invest in talent-based businesses, and he really knows what he’s looking for. Laine has helped Smith and Jay-Z succeed with some of their brands, but he’s also seen cases where talent-based brands didn’t quite work out.
Laine, an investor himself, said his job was to protect and vouch for entrepreneurs, in addition to protect his partners from what looked like a bad investment.
“I’ve been in a place where I know what it takes for these brands to win, so we look at our portfolio very differently than most people do,” Laine said.
Not every product has what it takes, he said. Freedom Trail Capital looks for products that have market fit, after all. If a celebrity is behind it, there has to be a good connection between the person and the product, and the person has to be willing to roll up their sleeves and get to work.
Laine recalled that he has had to deal with celebrities who refused to do a photo shoot or go to Target to promote their product.
“We’re not just talking about endorsements anymore,” Laine said. “We’re talking about owning a significant portion of the company. I’ve seen a lot of things fail, and really promising brands and companies fail as a result.”