In 2023, Samyr Laine and his wife, Ayanna Alexander-Laine, founded Freedom Trail Capital with the goal of reaching a $50 million fund, leveraging their experience as former Olympians in the triple jump for Haiti and Trinidad and Tobago, respectively, to support consumer brand founders.
Alexander-Laine expressed her passion for connecting with people and combining talent with business, highlighting the unique perspective athletes bring to the investment space. With third general partner Ivan Lopez, they have already invested in seven startups and have more in the pipeline.
Laine, a former track record-breaking Harvard athlete and roommate of Mark Zuckerberg, transitioned from elite athletics to a career in operations and strategy, ultimately leading to the inception of Freedom Trail Capital. His wife, Alexander-Laine, pursuing a doctorate, focuses on healthcare finance and equity. Laine’s journey involved overcoming failures and challenges to ultimately compete in the Olympics and inspire others to pursue their goals relentlessly.
To the Olympics and beyond
Their approach to investing in talent-led businesses stems from Laine’s experience in brand-building with Jay-Z and Will Smith. Freedom Trail Capital prioritizes partnerships where celebrities are actively involved, ensuring a strong connection between brand and influencer to drive success. Their stringent evaluation process aims to safeguard entrepreneurs and investors from potential pitfalls.
Working for Will Smith and Jay-Z
Laine’s transition from athletics to entrepreneurship gave him a unique perspective on investment decisions, allowing him to support portfolio companies effectively. Freedom Trail Capital’s dedication to partnering with committed celebrities and aligning brand values drives their success in the competitive investment landscape.
Their vision includes identifying products with strong market fit and celebrities willing to actively engage in promoting their brands. Laine emphasizes the importance of genuine involvement and dedication from influencers, highlighting the risks associated with passive endorsements.
