Recorded live at Holiday Valley Ski Resort in Ellicottville, New York, this Olympic Special of Skin In The Game explores what it truly takes to compete at the highest level in sport.

Hosts John Cimperman and Tim O’Shei sit down with three-time Paralympic gold medalist Adam Page, training center director Miguel Azcarate, and sports performance coach Dr. Jason Rich for a powerful conversation about sacrifice, deliberate practice, pressure, and mental resilience.

Airing during the Olympic Closing Ceremonies and just days before the Paralympics begin, this episode bridges both worlds and reminds us how greatness is built and the price it takes for a chance at the podium.

Entrepreneur and sports memorabilia pioneer Brandon Steiner joins Skin In The Game for a conversation about building businesses, preserving sports history and turning passion into purpose.

Steiner shares the entrepreneurial mindset that fueled his rise from a childhood spent working in a bagel factory to creating one of the most influential memorabilia businesses in sports. He reflects on decades of working with elite athletes, navigating fame and fortune and learning that success isn’t about chasing money—but about chasing the things that make the money.

The conversation centers on Steiner’s latest work transforming iconic stadiums into tangible memories for fans, including his ambitious project at Highmark Stadium in Buffalo, New York. From salvaging turf, signage, and locker-room artifacts to understanding what Bills fans truly value, Steiner explains the responsibility that comes with preserving a place so deeply tied to community identity.

Along the way, Steiner talks about leadership, mentorship, generational differences in the workplace, and why empathy, curiosity, and growth are essential to long-term success. This conversation will resonate with anyone who understands that sports live far beyond the scoreboard, and that the places where they’re played hold real meaning.

Former NFL Players Association Executive Director DeMaurice Smith joins Skin In The Game for a candid, wide-ranging conversation with hosts John Cimperman and Tim O’Shei about power, labor, and the true business of professional football.

Drawing from his new book Turf Wars: The Fight for the Soul of America’s Game, Smith takes listeners inside nearly 15 years of battles with the NFL — from collective bargaining and player safety to race, money, media, and the hidden forces that shape the league fans love. His unfiltered view explains why he never saw himself as a “football fan,” how that perspective shaped his leadership and why protecting players often meant challenging the very game itself.

Smith reflects on concussion protocols, workers’ compensation, union leadership, and the uneasy relationship between sports entertainment and journalism. Along the way, he makes the case that the NFL is not just a sports league — it’s a mirror of American labor, politics, and accountability.

This episode asks hard questions: Who really benefits from the football business and who pays the price?

What happens after you achieve the dream?

In this episode of Skin In The Game, hosts John Cimperman and Tim O’Shei sit down with Steve Mesler, Olympic bobsled gold medalist and founder of Mesler Performance Group, for a deeply honest conversation about success, identity, and life after elite competition.

Mesler reflects on his journey from Western New York to Olympic gold in 2010, the pressure and danger of competing at the highest level, and the unexpected emotional challenges that followed the peak of his athletic career. He is candid about his struggle with depression years after retiring from competition and the moment he realized that achievement alone was no longer enough. Now an executive performance coach and nonprofit founder, Mesler shares how those experiences shaped his approach to leadership, fulfillment, and sustainable performance.

This conversation extends far beyond sports. Whether you’re an athlete, a business leader, or someone navigating a major life transition, Mesler offers powerful insight into what it really means to perform, and live, at your best.

The following program contains mature content, including conversations about suicide, self-harm and mental health challenges.If you or someone you know is experiencing suicidal thoughts or a crisis, please reach out immediately to the Suicide Prevention Lifeline at 800-273-8255 or text HOME to the Crisis Text Line at 741741. In Canada, call or text 988, the Suicide Crisis Helpline.

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.

In this episode of Skin in the Game, award-winning investigative journalist Rick Westhead joins John and Tim for a powerful and deeply reported conversation about his book “We Breed Lions” and the culture of junior hockey in Canada.

In this episode of Skin in the Game, John and Tim dive into the psychology, history, and surprising power of trash talk with journalist and author Rafi Kohan, whose latest book explores how a few well-timed words can shape competition, performance, and culture. From Larry Bird and Michael Jordan to Tiger Woods and modern-day MMA, Kohan explains how trash talk isn’t just bravado — it’s a deeply human form of communication rooted in psychology, identity, and strategy. They explore why trash talk surged in the 1990s, how it intersects with race and cultural perception, why it can sharpen elite performance, or unravel it, and how the same lessons apply beyond sports to parenting, leadership, and everyday life. Along the way, Kohan shares stories from locker rooms, comedy stages, military training grounds, and global arenas, revealing why this “risky pleasure” remains one of the most fascinating elements of competition.

This episode of Skin In The Game explores the influence and leadership that impacts the future of sports.

In the first half of the episode, hosts John Cimperman and Tim O’Shei are joined by Josh Barnett of Sports Business Journal, the premier business-to-business publication in the sports industry. Barnett walks through SBJ’s Influence 125, a look at the most influential people in sports over the past 25 years. He explains how the list was created, why it isn’t ranked, and how influence shows up across ownership, media, technology, marketing, and league leadership. The conversation examines iconic figures like Roger Goodell, Jerry Jones, Robert Kraft, and Gary Bettman, while also considering the impact of on-air talent, global audiences, and emerging influence in women’s sports.

Then the episode features an encore presentation of a standout conversation with Troy Vincent, Executive Vice President of Football Operations for the NFL. Vincent shares how the league’s investment in flag football is expanding access, affordability, and opportunity — especially for girls and young women. He discusses the growth of sanctioned varsity high-school programs, college scholarships, and the road to flag football’s Olympic debut at LA28. Vincent also reflects on mentorship, leadership, and the responsibility athletes and leagues have to use their platforms for social impact, including his work addressing gender-based violence through the Vincent Commission.

Lake Placid has long been synonymous with Olympic history, but today it’s also a case study in how sport, tourism, and economic development work hand in hand. In this episode, John Cimperman sits down with Darcy Norfolk Rowe, Director of Communications for the Olympic Regional Development Authority (ORDA), to explore the business and impact of winter sports in New York State.

Golf is more than a game. It’s an economic engine, a job creator, a tourism magnet, and a powerful steward of green space. In this episode, John and Tim unpack the findings of New York State’s new Golf Impact Study with guests Gina Rizzi and Tom Kaplan, revealing a side of the sport most people never think about.

The conversation begins with the dollars-and-cents impact: how golf supports local economies, drives tourism in both Western New York and Southern Ontario, and sustains thousands of jobs across public and private courses. But the discussion quickly turns to a surprising and important theme, legislation. Gina and Tom break down how regulation, environmental policy, and rising operational costs are reshaping the golf industry, and why having a “seat at the table” in Albany is critical to protecting both courses and the golfers who rely on them.

Golf may look simply like a walk in the grass with a bag of clubs. But as this conversation shows, its impact runs far deeper.