Matthew Jolles - President & CEO, Gotham Sports & Entertainment Holdings

Lyle Adams – Founder & CEO, Spry

In this episode of Defining Moments, Dustin Heise sits down with Lyle Adams, Founder and CEO of Spry, a leading collegiate athletics management platform helping athletic departments streamline operations and better support coaches, administrators, and student-athletes. A former professional soccer player turned sports technology entrepreneur, Lyle shares how lessons from elite sport shaped his approach to leadership, resilience, and building a high-growth company. He reflects on the challenges of entrepreneurship, the importance of learning from failure, and why growth is rarely linear. The conversation explores the future of collegiate athletics, the increasing complexity facing athletes and administrators, and how technology can create more time for coaches to focus on what matters most: developing people. Lyle also offers thoughtful insights on athlete specialization, NIL, the transfer portal, and the evolving landscape of sport. This episode is packed with practical leadership lessons on perseverance, innovation, culture, and solving the right problems. What You'll Learn: *  Why failure is one of the greatest tools for growth  *  How elite athletes develop transferable leadership skills  *  The importance of building feedback-driven cultures  *  Why solving problems matters more than building features  *  The future of college athletics and sports technology  *  How leaders can create more impact by focusing on efficiency and people

Matthew Jolles - President & CEO, Gotham Sports & Entertainment Holdings

In this episode of Defining Moments, Dustin Heise sits down with Matthew Jolles, President & CEO of Gotham Sports & Entertainment Holdings, to explore how sport can become more than competition. Matthew shares how his time with ESPN and X Games shaped his belief in sport as a platform for culture, inclusion, and opportunity. He also unpacks his mission to make youth sports more transformational, affordable, and athlete-focused. From servant leadership to building organizations where players feel known by name, this conversation is about creating lasting impact in sport, business, and community.

Brett M. Johnson – CEO, Benevolent Capital | Chairman of Rhode Island FC & Centreville Bank Stadium

In this episode of Defining Moments, Dustin Heise sits down with Brett M. Johnson, CEO of Benevolent Capital and one of the most influential voices in the business of sport today. Brett shares the journey behind building Rhode Island FC, helping lead the resurgence of Ipswich Town FC, and why he believes sport is one of the most powerful tools for community connection and long-term economic impact. The conversation dives into sports ownership, entrepreneurship, leadership, stadium development, and the lessons Brett has learned while building organizations that extend far beyond the game itself. From taking risks and surviving adversity to creating values-driven cultures and investing in people first, Brett offers a candid look into what it really takes to build something meaningful in sport and business. This episode is a masterclass in vision, resilience, and the future of sports as an asset class.

Andrew Baker – Chief External Affairs Officer, Canadian Olympic Committee

On this episode of Defining Moments, Dustin Heise sits down with Andrew Baker to explore the power of sport far beyond the podium. From being inspired by the 1996 Olympics as a young athlete to helping shape the future of Canadian sport at the Canadian Olympic Committee, Andrew shares the defining moments that shaped his leadership journey. The conversation dives into the future of sport in Canada, the impact of the recent historic investment into the national sport system, and why modernizing sport means creating stronger connections between grassroots participation and high-performance success. Andrew also shares insights on Olympic hosting, global leadership, and how Canada can continue to inspire the next generation through sport. This episode is a powerful conversation about leadership, legacy, innovation, and the role sport can play in building stronger communities across Canada and around the world.

Kevin Blue - CEO & General Secretary, Canada Soccer

What does it take to lead a national sport through pressure, change, and a global spotlight? In this episode of Defining Moments, Dustin Heise sits down with Kevin Blue, CEO & General Secretary of Canada Soccer, to unpack the mindset behind high-stakes leadership. From his early days as a competitive golfer to leading major sports organizations across North America, Kevin shares how the mental game shapes decision-making at the highest level. He breaks down how he approached stepping into Canada Soccer without a traditional soccer background, why humility can build credibility, and how leaders earn trust in complex, multi-stakeholder environments. They also dive into the future of sport in Canada, including the role of philanthropy in funding, the challenge of aligning organizations around a shared vision, and the massive opportunity ahead with the 2026 FIFA World Cup.  This is a conversation about staying grounded under pressure, leading through uncertainty, and building something bigger than yourself.