In this episode, we dive into the remarkable journey of Samyr Laine, an investor, Olympian, and brand-builder who’s mastered the art of navigating both the sports and entertainment industries. Currently the Managing Partner and GP of Freedom Trail Capital, Samyr has held key leadership roles such as the SVP of Operations & Strategy at Westbrook Entertainment and Senior Director of Operations at Roc Nation. He’s worked on major celebrity-backed ventures, collaborating with industry giants like Will & Jada Pinkett Smith and Jay-Z, shaping the future of iconic brands while overseeing deal flow and driving portfolio growth. 

Prior to his entertainment career, Samyr gained invaluable experience in sports with Major League Soccer and Monumental Sports & Entertainment, and even represented Haiti in the 2012 London Olympics, finishing 10th in the triple jump. With degrees from Georgetown Law, The University of Texas, and Harvard University (where he was roommates with Mark Zuckerberg), Samyr’s brand-building journey stands as a powerful testament to passion, perseverance, and seizing the opportunities that come your way.

What You’ll Learn in This Episode

• (2:55) Lawyer Turned Operator Turned Investor: Samyr shares his unique career evolution, starting from law school and transitioning into operations and venture capital.
• (8:45) Bold Moves: From Law to Leadership: Reflections on how his legal background at Georgetown Law equipped him with the skills to navigate the worlds of entertainment and venture capital.
• (11:15) Olympic Athlete: Insights into his journey representing Haiti in the 2012 London Olympics and how sports taught him resilience and discipline.
• (15:00) Early Days at Harvard University w/ Zuck: A look at his time at Harvard, including his experience rooming with Mark Zuckerberg and how it shaped his entrepreneurial mindset.
• (17:52) Elevating Entertainment Brands at Roc Nation: Behind the scenes of leading operations for JAY-Z’s entertainment empire and the impact of his work on their publishing blueprint.
• (25:47) Collaborating with Will & Jada Pinkett Smith at Westbrook Entertainment: How Samyr’s role in celebrity ventures expanded his expertise in entertainment branding, including managing the entire consumer goods IP of Westbrook.
• (28:24) Building Celebrity-Backed Brands: Using the power of celebrity influence to propel brands to new heights and what it’s like to manage celebrity relationships.
• (39:00) What Inspires His Investment Choices: Learn how Samyr invests in and advises ventures like Issa Rae’s Sienna Naturals and Ciara’s Ten to One Rum.
• (52:07) What It Means to be a Brand Builder: A look at his core philosophy behind building and scaling impactful brands.
• (56:57) Top 3-5 tips to build a better brand?: Samyr’s actionable insights on what it takes to create a successful, enduring brand.

Connect with Samyr Laine on Instagram and LinkedIn here. 

Samyr's investment firm, Freedom Trail Capital: https://www.freedomtrail.capital/

Connect with Tony Triumph: @tonytriumphofficial (IG), Tonytriumph10 (Twitter), LinkedIn