Samyr Laine took a page from Roc Nation’s investment book and is now helping other startups.
Laine, a Harvard graduate who roomed with Facebook Founder Mark Zuckerberg, is behind Freedom Trail Capital, an investment firm backing “fully functioning, well operated, effectively managed and revenue generating businesses,” its website mentions. The firm was established in 2023 alongside his wife, Ayanna Alexander-Laine.
The couple-turned-founders also share history in the sports world as former track and field Olympians, with him representing Haiti and she, Trinidad and Tobago.
“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.”
Freedom Trail Capital, featuring Ivan Lopez as a third general partner, has funded seven startups, including Issa Rae’s Sienna Naturals and Ciara’s Ten to One Rum.
A part of the firm’s intuition has been guided by Laine’s prior experience. He was the 11th person to test out Facebook and recognized the app’s promise in its early days.
“Mark was always a builder, and we knew he was going to do something tremendous, of course,” Laine commented, according to TechCrunch.
After his Olympic glory days, Laine obtained jobs in sports and later pivoted to entertainment and brand-building at Jay-Z’s Roc Nation from June 2018 to September 2019, according to his LinkedIn. He was tasked with the responsibility of helping the brand grow across its sectors, which included music, apparel, spirits, cannabis, and book publishing.
After this post, he transitioned to Westbrook, a media company founded by powerhouse couple Will Smith and Jada Pinkett Smith. He served as their
“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 explained, per TechCrunch. “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.”
With experience assisting the Smiths and Jay-Z with their brands, Laine possesses deep insights into market success that is reflected through Freedom Trail Capital.
“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 expressed to TechCrunch. Products must be a strong fit in the market, and if celebrities are involved, he wants to see them “roll up their sleeves and get to work.”
Freedom Trail Capital is in the process of raising $50 million in new capital.
