Samyr Laine and his wife, Ayanna Alexander-Laine, started Freedom Trail Capital in 2023 and are working their way 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 grit and determination to work for founders wanting 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 found that athletes are good in these spaces. We also have the stamina to conquer other things and other entities outside of sports.”

They, along with third general partner, Ivan Lopez, have invested in seven startups so far with a small first fund close. These include a hair care company by 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 another seven investments in the pipeline as Freedom Trail Capital continues to raise capital, Laine told TechCrunch.

To the Olympics and beyond

Laine knows what it’s like to start and scale companies. He was previously working as senior vice president of operations and strategy at Westbrook, the venture 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 healthcare finance and healthcare inequities.

Laine also knows what it’s like to fail. He tried out for the track team in the seventh grade and ended up being cut the next year. It wasn’t until he was a junior in high school that he decided to try again with track, this time getting serious with the triple jump.

All was good, though. Laine ended up going to Harvard and setting some track records with the team. He also was roommates with Mark Zuckerberg. They had a four-person dorm room freshman year, and they even shared bunk beds. Laine ended up being maybe the 11th person to get on Facebook and test it out, he said. He also was a trivia question on the show “Cash Cab” about which Olympian was roommates with Zuckerberg, Laine said.

“Mark was always 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 track and field. Teammates there competed on a different level, as many had been world junior 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. 

He was balancing training and going to law school at Georgetown University when he tried out for the Olympics again in 2012 and qualified. A lot of people told him it was too much, but now when anyone asks him for advice, he tells them to “go do the thing you won’t be able to do.”

“I thought if I could go to law school and balance it, I could get there,” Laine said. “At that point, I was No. 7 in the world in the triple jump, and going to 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 professionals in track and field. Laine learned from his UT teammates how to make money doing that. He was also able to get sponsorships and monetary assistance from the international Olympic committee. 

Working for Will Smith and Jay-Z

After that, he had some additional careers in sports before he got into entertainment and brand-building at Roc Nation. Laine worked with Jay-Z to build and scale his brands that 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.

“I wasn’t necessarily allocating capital and investing, but I did have a front-row view into some of the investment decisions that Roc Nation’s fund made,” Laine said. “I am an operator at heart, so it gives me a unique perspective on how we do diligence on investment opportunities and can support our portfolio companies.”

Freedom Trail Capital’s thesis is to invest in talent-led businesses, and he really knows what he’s looking for. Laine has helped Smith and Jay-Z be successful with some of their brands, but has also seen some cases where talent-led brands didn’t go the way they were supposed to.

Now that he is on the other side as an investor, Laine said it is his job to protect and vouch for the entrepreneurs while also protecting his limited partners from what looks like a bad investment.

“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,” Laine said.

Not every product has what it takes, he said. Freedom Trail Capital is looking for products that have product market fit, of course. If there is a celebrity behind it, there has to be a good connection between the person and product, and the person has to want to roll up their sleeves and get to work. 

Laine said there were times when he dealt 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.”