How Winning Teams Are Built: Craig Custance on Leadership, Culture, and Power in Sports

What does it really take to build a winning sports organization? In this episode of Skin In The Game, hosts John Cimperman and Tim O’Shei sit down with Craig Custance, author of The Franchise: The Business of Building Winning Teams and Head of Creative Development at The Athletic, for a deep dive into leadership behind the scenes of professional hockey. Custance draws on years of reporting and unprecedented access to NHL general managers, owners, and executives to explore how championship teams are actually built, far beyond what fans see on the ice. The conversation spans front-office decision-making, ownership dynamics, organizational culture, and the personal toll of leadership at the highest level of sport. While rooted in hockey, this conversation resonates far beyond sports. Custance shows how the principles that drive winning teams — trust, clarity, accountability, and long-term thinking — apply just as directly to business, media, and organizational leadership. Whether you’re a sports executive, a business leader, or simply fascinated by how high-performing teams operate, this episode offers rare insight into what happens where championships are truly won.