Why I Treat Talent Like A Dynamic Asset, Not A Fixed Resource

When I cofounded Freedom Trail Capital, I made a bet that most investors were thinking about talent all wrong. They were treating it like a commodity—something you buy, plug in and hope performs. My experience as an Olympian taught me something different: Talent isn’t fixed. It’s dynamic, shaped by opportunity, leadership and environment. You don’t just find great teams, you build them.

This philosophy shapes everything we do at Freedom Trail, from the founders we back to how we advise our portfolio companies on building their organizations. After working with dozens of startups and their leadership teams, I’ve learned that the companies that scale successfully aren’t necessarily the ones that start with the most impressive, traditional resumés. They’re the ones that understand how to develop culturally relevant talent and partnerships with these individuals.

Hire for energy and adaptability, not just experience.

Some early-stage startups can’t afford to hire Fortune 500 companies. The best early-stage teams look for people who can wear multiple hats and figure things out as they go. Training happens through mentorship and real-time problem solving, not lengthy onboarding programs.

This creates something larger companies struggle to replicate: a strong sense of ownership across the team. When everyone is learning on the fly and contributing value regardless of job title, culture gets built through shared moments rather than HR policies. People stay not because of the perks, but because they feel like they’re building something of their own.

Remember, leadership is built on trust.

One mistake some founders make is believing their company can’t run without them in the room. If that’s true, your company isn’t ready to grow. Because succession planning isn’t about stepping aside; it’s about building a team and culture that can stand on its own.

My experience in entertainment and brand-building at Roc Nation and Westbrook gave me a front-row view of how successful leaders scale their influence through others. The founders who get this right see leadership as something earned through trust rather than granted through titles. They document how they think, share leadership early, and let others take the spotlight when it serves the business.

I look for this mindset in the founders we back at Freedom Trail. The best ones understand that a founder’s mindset is about being resourceful, coachable and focused on building something bigger than yourself.

Cultural icons need to bring more than visibility.

We invest in companies led or powered by cultural figures, but visibility alone doesn’t create value. I learned this firsthand during my time working with Jay-Z at Roc Nation, and later, with Will and Jada Pinkett Smith at Westbrook. The cultural icons who really move the needle are those who understand their audience and are genuinely part of the culture themselves.

Take our portfolio companies: Issa Rae’s Sienna Naturals hair care line, Kaley Cuoco’s Oh Norman! pet products, or Ciara’s Ten to One Rum. In each case, the founder’s influence aligns authentically with the mission and they’re truly involved in building the business. They can shape how people feel about a brand in ways that go far beyond exposure because they’re not just endorsing, but rather creating from personal experience and passion.

Purpose isn’t a buzzword—it’s the strategic backbone of resilient companies.

Purpose is what keeps teams grounded when things get intense. When people really believe in what they’re doing, they’re more resilient and more connected. It helps cut through the noise and reminds everyone why the hard work matters.

I pay attention to how founders treat their people when no one’s watching. How do they handle setbacks? How do they celebrate wins? Culture shows up in those everyday choices: how safe people feel speaking up, how decisions get made, whether values are lived or just written down. When culture is real, it attracts the right people and keeps them.

AI changes the game, but humans still win it.

The smartest teams I’m seeing use AI to take repetitive work off their plates so they can focus on creativity and strategy. Roles are becoming more fluid, and people are being asked to think across functions. It’s less about fitting into a job description and more about contributing where you’re strongest.

As AI handles more routine tasks, the human elements of work become more valuable: judgment, storytelling, empathy. Companies that understand this are designing roles differently. They’re focusing on what humans do best while letting technology handle the rest.

Consistency is just as important as intensity.

Training for the Olympics taught me that consistency is just as much of a priority as intensity every time. You have to show up every day, even when it’s hard. That mindset translates directly to entrepreneurship and team building. You won’t always feel motivated, but discipline carries you through.

I also learned how important recovery is. Rest, reflection and support systems are just as crucial as effort. And maybe most importantly, I learned that great performance is a team effort, even in individual sports. You need people around you who believe in your vision and help you keep going when things get tough.

The best founders I work with understand this. They’re driven but grounded. They’re curious, clear about their purpose, and not afraid to get their hands dirty. Early on, I look for how someone responds under pressure, how they take feedback and whether they see leadership as something earned through trust.

Small moments matter most.

People don’t leave jobs—they leave managers and cultures. The most overlooked retention strategies I see working are the simplest ones: involving mid-level leaders in real decision making, small moments of recognition, clear growth paths, and honest communication.

One strategy that consistently works is giving people real ownership over problems and trusting them to solve them. When team members feel challenged and trusted, they stick around. It’s not always about flashy benefits—it’s about showing people they matter.

The companies that will win the talent war aren’t the ones with the biggest budgets or the flashiest perks. They’re the ones that understand talent is something you develop—and they invest in creating environments where people can grow, contribute meaningfully and build something they’re proud of. That is ultimately the foundation of sustainable competitive advantage.