When Samyr Lainé walked into his freshman dorm room at Harvard University in 2002, he found his new roommate tucked away in the corner of their room, typing away on his computer.
A year and a half later, that roommate sent him a project he was working on called TheFacebook.
“You could tell where his skill set was as a coder and as a thinker, and he was just supremely advanced,” Lainé said of Meta CEO Mark Zuckerberg. “He was taking senior-level courses as a freshman and showing up to a three-hour final exam, two hours late, and getting the highest grade in class.”
While living in that dorm room, Lainé began to hone his skills as a triple jumper on Harvard’s track and field team. After college, he competed as a graduate student at the University of Texas at Austin. He then went on to study law at Georgetown, graduating in 2010.
A decade after sharing a bunk bed with Zuckerberg, Lainé represented Haiti in the triple jump at the 2012 Olympic Games in London. Ten years after that, he co-founded Freedom Trail Capital, a venture capitalist firm that invests in celebrity brands like Issa Rae’s haircare line Sienna Naturals, Kaley Cuoco’s dog supplement company Oh Norman!, and Ten to One Rum, co-owned by the singer Ciara.
From his time as an Olympian, Lainé understands what it is like to be the talent fronting a product. After his athletic career ended, he went on to work with Jay-Z at Roc Nation and with Will and Jada Pinkett Smith on their media company, Westbrook. Those experiences were pivotal in teaching Laine how to make a celebrity brand successful.
From the Olympics to Roc Nation
After placing tenth in the triple jump at the London Olympics, Lainé continued to work in sport, first as a lawyer at Monumental Sports, which owns several Washington, D.C. sports teams including the Capitals, Wizards and Mystics, and later directing player relations at Major League Soccer.
He joined Jay-Z’s entertainment company Roc Nation in 2018 as senior director of operations, using both his legal background and operations skills to manage artists like Alicia Keys, Meek Mill, Lil Uzi Vert. He also worked on Jay-Z’s alcohol brands, music streaming platform Tidal, and launched projects like the company’s book publishing division, Roc Lit 101.
“My role at Roc Nation is really what laid the foundation for what I’m doing today,” he said. “For me, [it] was just having a front row seat and understanding how Jay leverages his cultural cachet to build some really valuable, really tremendous businesses,” he said.
Lainé left Roc Nation in 2019 to then join the Smiths at their media and production company, Westbrook, as vice president of operations. He was then promoted to senior vice president, working with the entire Smith family to launch apparel, personal care, and coffee brands.
“I came on as a very early employee, maybe employee number six or seven. We built that to almost 200 employees across six different verticals,” he said. “A lot of [the job] was taking what I learned—a baptism by fire Roc Nation—translating that to Westbrook.”
The Friday before the 2022 Oscars (the one when Smith slapped comedian Chris Rock), Lainé left Westbrook to consult for brands and address what he saw as a gap in the market between celebrity-led brands and venture capital.
A year later, he co-founded Freedom Trail Capital with his wife and fellow triple jump Olympian Ayanna Alexander-Lainé. Together, the two have amassed a portfolio of celebrity-led brands trusted by consumers and celebrities alike.
Investing in authentic brands
What will make or break a celebrity brand is authenticity, not just a famous name attached to a company, Lainé said, before pointing to the many mediocre celebrity tequila brands out there as an example. Sometimes, Lainé warned the product doesn’t even match the name behind it.
Take for example Jay-Z’s successful cognac and champagne brands—most people don’t remember his vodka venture Armadale.
“Vodka was probably the wrong category for the wrong demographic that Jay-Z appeals to,” Lainé explained. “What doesn’t work, and people know this, is inauthentic pairings between talent and business.”
Companies fail when they don’t need to think critically about their product and how it will serve customers, he said. Freedom Trail takes a different approach.
“We look for businesses that either have or can benefit from having a person of influence involved. Person of influence, we say deliberately, because we’re not exclusively looking for celebrities, but we’re looking for folks who have a platform and an audience where they can add their audience to authentically supercharge an already great business,” Lainé explained.
Lainé’s goal is that a company survives with or without a big name’s backing. But when an influential person becomes involved, they tend to bring their audience with them.
He points to his client and Harry Potter actress Emma Watson. Her family’s gin brand, Renais, is the quintessential example of an influential person backing a brand. The gin comes from recycled grape skins from Watson’s family’s vineyard in Burgundy, France, where her father has been growing grapes for more than three decades. Her brother, Alex, is the company’s CEO, and Watson designed the product’s bottle and packaging, Lainé said. And that authenticity translates to other well-known and beloved brands.
“The reason that Nike is a talent-led brand, and Revlon and Gatorade [is that] they all leverage talent successfully, Lainé said. “The right person with the right audience and the right messaging through the right medium speaking to the direct demographic at the right time can supercharge a business. That business that it’s supercharging has to be a great product that’s innovative and a quality business and a strong brand.”
In 2002, Samyr Lainé arrived at Harvard University and met his roommate, Mark Zuckerberg, who was already showing exceptional coding skills. A year and a half later, Zuckerberg introduced Lainé to a project he was working on called TheFacebook. Lainé recognized Zuckerberg’s exceptional talent, noting that he was taking senior-level courses as a freshman and achieving top grades, even after arriving late for exams.
While at Harvard, Lainé excelled as a triple jumper and later competed at the University of Texas at Austin. He graduated from Georgetown Law School in 2010 and went on to represent Haiti in the triple jump at the London Olympics in 2012. A decade later, he co-founded Freedom Trail Capital, a venture capital firm investing in celebrity brands, including Issa Rae’s Sienna Naturals and Kaley Cuoco’s Oh Norman! dog supplements.
Lainé’s journey from Olympic athlete to venture capitalist involved significant experiences in sports law and entertainment. After the Olympics, he worked as a lawyer for Monumental Sports, which owns various Washington, D.C. teams, and later directed player relations at Major League Soccer. He joined Jay-Z’s Roc Nation in 2018 as senior director of operations, where he managed high-profile artists and contributed to various projects, including Jay-Z’s alcohol brands and the book publishing division Roc Lit 101.
Lainé credits his time at Roc Nation as foundational for his current endeavors. Observing how Jay-Z leveraged his cultural influence to build successful businesses provided Lainé with invaluable insights. In 2019, he transitioned to Westbrook, the media company owned by Will and Jada Pinkett Smith, where he played a crucial role in expanding the company and launching various celebrity-led brands.
Before the 2022 Oscars, Lainé left Westbrook to explore the market gap between celebrity brands and venture capital. This led to the founding of Freedom Trail Capital with his wife, Ayanna Alexander-Lainé, also a former Olympian. The firm focuses on investing in authentic brands that resonate with both consumers and celebrities.
Lainé emphasizes that the success of a celebrity brand hinges on authenticity rather than mere celebrity endorsement. He points out the pitfalls of inauthentic pairings, like Jay-Z’s vodka venture, which failed to connect with his demographic. In contrast, successful brands like Jay-Z’s cognac and champagne exemplify how authenticity can drive brand success.
Freedom Trail Capital seeks to identify businesses that can benefit from influencer involvement. Lainé defines « person of influence » broadly, not limited to celebrities but including anyone who can authentically amplify a brand. He highlights Emma Watson’s family gin brand, Renais, as a prime example, showcasing the importance of genuine connections between the influencer and the product.
Lainé asserts that a successful partnership between talent and business requires the right person, audience, and messaging. He cites Nike and Gatorade as brands that effectively leverage talent to enhance their market presence. Ultimately, Lainé aims for the companies he invests in to thrive independently, while also benefiting from the backing of influential figures who can attract their audiences.
