Samyr Laine and his wife, Ayanna Alexander-Laine, started Freedom Trail Capital in 2023 and are working toward a $50 million fund.
Both are former Olympians who competed for Haiti and Trinidad and Tobago, respectively, in the triple jump. Now they put their passion and determination to work for founders who want to launch and scale consumer brands.
“I love people and connecting with people,” Alexander-Laine told TechCrunch. “We know how to merge talent and business and we’ve found that athletes are good in those spaces. We also have the stamina to conquer other things and entities outside of sports.”
Along with a third general partner, Ivan Lopez, they have invested in seven startups so far with a small seed fund closed. These include a hair care company from Issa Rae called Sienna Naturals. a pet product company started by Kaley Cuoco called Oh Norman! Ciara’s Ten to One Rum? and Kudos, a diaper company backed by Mark Cuban and Gwyneth Paltrow.
There are seven more investments in the pipeline as Freedom Trail Capital continues to raise capital, Laine told TechCrunch.
Towards the Olympics and beyond
Laine knows what it’s like to start and scale companies. He previously served as senior vice president of operations and strategy at Westbrook, the venture capital firm founded by Will Smith and Jada Pinkett Smith. He also spent time as director of operations at Roc Nation, working with Jay-Z. Meanwhile, Alexander-Laine is getting her doctorate in business administration and will focus on health care financing and health care disparities.
Laine also knows what it’s like to fail. He tried out for the track team in seventh grade and ended up getting cut the following year. It wasn’t until he was in high school that he decided to try track again, this time getting serious about the triple jump.
Everything was fine though. Laine ended up at Harvard and set some records with the team. She was also roommates with Mark Zuckerberg. They had a four-person freshman dorm, and they even shared bunk beds. Laine ended up being maybe the 11th person to log onto Facebook and try it, he said. It was also a trivia question on the “Cash Cab” show about which Olympian was Zuckerberg’s roommate, Laine said.
“Mark has always been a builder, and we knew he was going to do something tremendous, of course,” Laine said.
When Laine transferred to the University of Texas, he was exposed to a new world of athletics. The teammates there competed at a different level, as many were junior world champions. Laine competed in his first Pan American Games in 2007. He also tried out for the Olympics in 2008 and missed competing in the triple jump by a few centimeters.
She was balancing training and going to law school at Georgetown University when she tried again for the Olympics in 2012 and qualified. Many told him it was too much, but now, when someone asks him for advice, he tells them “go do what you won’t be able to do.”
“I thought if I could go to law school and balance that, I could get there,” Laine said. “At that point, I was No. 7 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 didn’t end up getting a medal.”
For 10 years, Laine and Alexander-Laine competed around the world as track and field professionals. Laine learned from his UT teammates how to make money doing this. He was also able to receive sponsorships and financial assistance from the International Olympic Committee.
Working for Will Smith and Jay-Z
After that, he had some additional 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, cannabis and a book publishing division. He even managed some platinum recording artists. From there, he went to Westbrook to do similar things for Smith and Pinkett Smith. He was there for four years before starting Freedom Trail Capital.
“They didn’t necessarily have capital and investment, but I had a first look at some of the investment decisions that Roc Nation’s fund made,” Laine said. “I’m an operator at heart, so it gives me a unique perspective on how we do due diligence on investment opportunities and can support our portfolio companies.”
Freedom Trail Capital’s thesis is to invest in talent-driven businesses and it really knows what it’s looking for. Laine has helped Smith and Jay-Z be successful with some of their brands, but she’s also seen some cases where brands with talent didn’t go their way.
Now that he’s on the other side as an investor, Laine said it’s his job to protect and underwrite entrepreneurs while protecting his limited partners from what looks like a bad investment.
“Having been in a place where I know what it takes for these brands to win, we look at our portfolio very differently than most people,” Laine said.
Not every product has what it takes, he said. Freedom Trail Capital looks for products that are a natural product-market fit. If there’s a celebrity behind it, there has to be a good connection between the person and the product, and the person has to want to roll up their sleeves and get to work.
Laine said there were times when he was dealing with a celebrity who wasn’t willing to do a photo shoot or go to Target to promote the product.
“We’re not just talking about endorsements anymore,” Laine said. “We’re talking about you owning a significant part of this company. I’ve seen things fall by the wayside, and really promising brands and companies fail as a result.”
