Meet Mark Zuckerberg’s college roommate, an Olympian-turned-VC exec who invests in celeb businesses

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.”