Keep Showing Up: Interview with Olympian Samyr Laine
I recently went one-on-one with Samyr Laine. Samyr Laine is the Managing Partner and GP of Freedom Trail Capital and competed for Haiti in the 2012 Summer Olympics.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Samyr: Thanks for having me! My journey really started in upstate New York. I was all about soccer as a kid, but after getting cut from the track team in seventh grade, I thought that might be the end of that chapter. It wasn’t until the end of my junior year (inspired by the Sydney Olympics) that I decided to give track another shot, focusing on the triple jump. As any student-athlete can attest, balancing sports with school isn’t easy, and for me, that balancing act was even tougher while in law school, especially as I was trying to qualify for the Olympics myself. Each setback taught me something valuable about resilience and hard work—those challenges and the patient, diligent climb from a barely recruited high school athlete, to top 10 in the world, are what really shaped me.
Adam: What is your most meaningful memory from your Olympic experience? And what is something that would surprise people about the life of an Olympian?
Samyr: Competing for Haiti in London 2012 is definitely a highlight for me. The energy of the Games was electrifying, and the pride of representing my country was indescribable and my most meaningful memory was being able to look up into the stands after qualifying for the finals, and seeing my entire family there cheering. One thing that might surprise people is how much goes into the behind-the-scenes of training, and more specifically, how much of one’s preparation is focused on rest and recovery for the next training session or competition. It’s a grueling process, filled with early mornings, long workouts, and sacrifices that most people don’t see, along with lots of time spent on massage, chiropractor and physio therapy tables. It’s not just about the moment of competition. I learned a lot about resilience and the importance of adaptability. Not winning a medal in London was tough, but it taught me that the journey is just as important as the destination. Plus, I realized how crucial teamwork is—my coaches and training partners were instrumental in pushing me to be my best.
Adam: What are the best lessons you learned from your Olympic experience?
Samyr: Competing at the Olympics taught me invaluable lessons that I carry into my work as an entrepreneur and investor to this day—I truly believe there is a lot of crossover between performing at a high level in athletics and business alike! One of the most important lessons I learned from my Olympic experience is the necessity of resilience. As an athlete, you're constantly facing setbacks—whether it's a loss, injury, or a bad day of training—and it's no different in business. You have to stay focused on the long-term goal and keep pushing forward, even when things don’t go your way.
Similar to resilience, another key lesson or skill that carries over is discipline. At the highest level of sport, success is about consistent effort over time, refining your craft, and maintaining a routine that prepares you for peak performance. In entrepreneurship and investing, it’s really no different. You need the discipline to keep learning, analyzing opportunities, and staying ahead of trends to succeed, and you have to keep showing up for your business every day no matter what setbacks you might have faced the day before. My process included setting and writing down, daily training objectives and revisiting them each evening, and then doing the same before and after competitions, to ensure that I was very clear about what I wanted to work on or achieve, whether or not I did so, and if not, what adjustments I needed to make.
Adam: What are your strongest memories and best lessons learned from your time spent with Mark Zuckerberg?
Samyr: Living with Mark Zuckerberg at Harvard, sharing a dorm room, bunk beds, and all, let me see firsthand how innovative and forward-thinking he was. Even back then, he was building things, like a predictive media playing program long before it became mainstream (and a good bit before iTunes). When he launched Facebook, I was one of the first users, and while I didn’t imagine it would become such a massive success, I recognized its potential to change how we connect. That experience really opened my eyes to the power of ideas and relationships. Mark’s drive and willingness to take a risk and go all in on scaling what he’d built pushed me to think bigger, which has helped shape my own transition from athletics to business and now into investing. Now, with Ayanna, I’m channeling those lessons into Freedom Trail Capital, where we invest in consumer tech brands that blend culture and lifestyle. It’s all about making meaningful connections, just like I learned from him.
Adam: What do you believe are the defining qualities of an effective leader?
Adam: What do you believe are the defining qualities of an effective leader?
Samyr: I think effective leaders need to be resilient, empathetic, and forward-thinking. They should understand their team and know how to motivate people. Being adaptable is also key; sometimes plans change, and a good leader can pivot when necessary.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Samyr: They should stay inquisitive, always seek feedback themselves, and be open to learning new things. Building strong relationships within their teams is essential, and setting clear goals can help everyone stay focused. Finding mentors and listening to diverse perspectives can really enhance one’s leadership abilities. Lastly, and this relates to all of the above, but do a whole lot of reading.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Samyr:
1. Embrace resilience. Setbacks are inevitable, but they’re also opportunities to grow. Learn from them and keep pushing forward.
2. Prioritize relationships. Networking isn’t just about business; it’s about building genuine connections that can support you along the way. Also, those relationships really should be more than merely transactional.
3. Stay true to your vision. Always keep your long-term goals in sight but be flexible in how you get there.
Adam: What is the single best piece of advice you have ever received?
Samyr: The best advice I’ve received, and this was instilled in me by my parents growing up, is that “if something were easy, everyone would be doing it.” Along those same lines, is that “nothing worth having comes easy.”
Adam: Is there anything else you would like to share?
Samyr: We started our venture fund, Freedom Trail Capital, and it’s been such an exciting business adventure. As Olympians, we’ve always pushed each other to reach new heights, and now we’re applying that same drive to our investments. We focus on the intersection of culture, lifestyle, and influence meeting. In today’s fast-moving world, understanding these elements is key to finding growth opportunities. We believe that investing at this intersection not only fuels innovation but also gives brands an edge in a crowded market. Working with Ayanna has been incredibly rewarding. We share a vision and passion for helping entrepreneurs succeed, and we’re really excited to make a positive impact by supporting brands that connect with people. It's all about creating something meaningful together.
Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.
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