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  • Lyndsey D’Arcangelo on Walking Away, Starting Over and the Game Within

    Lyndsey D’Arcangelo on Walking Away, Starting Over and the Game Within
    Oct 10 2026
    Why walk away from a successful sportswriting career just as women’s sports are experiencing unprecedented growth? On this episode of Skin In The Game, John Cimperman and Tim O’Shei welcome longtime sportswriter and author Lyndsey D’Arcangelo, who built a career telling the human stories behind athletes and helping launch The Athletic’s WNBA coverage. D’Arcangelo explains why she stepped away from sports journalism, including an industry increasingly driven by clicks, outrage and social media engagement instead of the kind of storytelling that first drew her to the profession. She also reflects on the remarkable growth of women’s sports and why she believes the audience was there all along. Today, D’Arcangelo is taking the skills she developed interviewing some of the biggest names in sports and applying them in a new way as a life coach working primarily with women athletes. She helps athletes navigate performance pressure, major transitions and a question that can become especially difficult when sports have defined so much of their lives: Who am I beyond the athlete? The conversation also explores the pressures surrounding youth sports, the role parents play, what D’Arcangelo learned from elite athletes about mindset, and why she has returned to writing through her newsletter, The Game Within.
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    47 Min.
  • Why Being a Sports Fan Gets So Emotional

    Why Being a Sports Fan Gets So Emotional
    Sep 19 2026
    On this episode of Skin In The Game, John Cimperman and Tim O’Shei welcome psychologist and lifelong Philadelphia Eagles fan Dr. Patrick McElwaine to explore the psychology behind sports fandom and why our favorite teams can become such an important part of our identity.
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    54 Min.
  • Why She’s Betting on Women’s Sports

    Why She’s Betting on Women’s Sports
    Aug 29 2026
    Women’s sports are booming. But when investors look beyond the headlines, where are the real opportunities? On this episode of Skin In The Game, John Cimperman and Tim O’Shei welcome entrepreneur, investor, and author Chantell Preston, one of the owners and founders of the League One Volleyball San Francisco Signal, to talk about why she believes professional volleyball could be one of the next big growth stories in sports. Preston spent years evaluating emerging sports leagues before deciding where to put her own money. She explains why volleyball stood out, what she looks for before investing in a team or league, and why the sport’s enormous participation base and growing professional infrastructure caught her attention. The conversation also explores the broader surge in women’s sports, the importance of investing in female athletes and businesses, the opportunities — and risks — surrounding emerging leagues, and what athletes can bring from the court into the boardroom. Preston also shares lessons from her book, The Success Lie, including why she stopped defining success by money and titles, how sports helped shape her approach to leadership and resilience, and why success may have more to do with the journey than the outcome. It’s a conversation about money, opportunity, leadership, and what happens when you’re willing to bet on something before everyone else sees its potential.
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    47 Min.
  • Are We Ruining Youth Sports?

    Are We Ruining Youth Sports?
    Aug 22 2026
    Kids say they play sports for two main reasons: to have fun and to be with their friends. So why have youth sports become increasingly expensive, competitive, and difficult for many families to navigate? This week on Skin In The Game, John Cimperman and Tim O’Shei sit down with Jon Solomon, Research Director for the Aspen Institute’s Project Play initiative, to examine what the research tells us about the state of youth sports in America. Participation is rebounding after the pandemic, but Solomon says a troubling divide is growing. Children from the highest-income households are about twice as likely to play organized sports as those from the lowest-income households, while the average amount parents spent on a child’s primary sport increased 46% over five years. The conversation explores the commercialization and privatization of youth sports, the growing role of private equity, and why parents can feel pressured to spend thousands of dollars on travel teams, specialized coaching, and year-round competition just to give their children a chance to make a high school team. It’s a conversation about money, access, and whether youth sports are still serving the kids who play them.
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    47 Min.
  • Who Really Has the Power in Sports?

    Who Really Has the Power in Sports?
    Aug 15 2026
    College sports are changing at a dizzying pace. Athletes are getting paid, players are moving from school to school, and the possibility of college athletes collectively bargaining may be closer than many fans realize. This week on Skin In The Game, John Cimperman and Tim O’Shei sit down with sports and labor attorney Michael Elkins, founder of MLE Law, to examine the rapidly changing relationship between athletes, teams, schools, and leagues. Elkins, who represents college and professional athletes, makes a provocative case that despite all the criticism surrounding NIL and the transfer portal, college sports have never been better. He argues that athletes should have the same freedom to pursue better opportunities that coaches and other professionals have enjoyed for years. The conversation also moves into professional sports, including why the NFL Players Association faces a fundamental challenge that other sports unions do not: Most NFL players have short careers, and many never reach a second contract, making a prolonged work stoppage difficult for players to withstand. And Elkins explains why sports fans should be watching Major League Baseball, where another labor battle could threaten a sport he believes finally has momentum again. It’s a conversation about money, leverage, and the people fighting for their share of an increasingly lucrative sports industry.
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    54 Min.
  • The $2+ Billion Deal Behind the Bills' New Stadium

    The $2+ Billion Deal Behind the Bills' New Stadium
    Aug 8 2026
    The Buffalo Bills are about to open a state-of-the-art stadium in Orchard Park, ushering in a new era for one of the NFL's most passionate fan bases. But how did the deal come together, and what does it mean for the future of Buffalo? This week on Skin In The Game, John Cimperman and Tim O'Shei sit down with business leaders Bill Maggio and Jordan Levy, two trusted advisors who worked behind the scenes during negotiations for the Bills' new stadium. They discuss the relationships that helped move negotiations forward, the roles played by Governor Kathy Hochul, NFL Commissioner Roger Goodell, Terry Pegula, and Erie County, and the difficult decisions that ultimately kept the Bills in Western New York. The conversation also explores one of the biggest questions surrounding the project: Should the stadium have been built in downtown Buffalo instead of Orchard Park? Looking back, both guests share their perspectives on that debate and explain why they now believe Buffalo's next major investment should focus on the Cobblestone District and revitalizing the area around KeyBank Center. It's an honest conversation about leadership, negotiation, public investment, and what Buffalo got right, what it may have missed, and what comes next.
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    54 Min.
  • Did the World Cup Deliver? The Real Business Impact of FIFA 2026

    Did the World Cup Deliver? The Real Business Impact of FIFA 2026
    Aug 1 2026
    Millions of fans filled stadiums across North America during the 2026 FIFA World Cup, but did host cities actually win? This week on Skin In The Game, John Cimperman and Tim O’Shei look at the impact of the world’s biggest sporting event from two very different perspectives. First, Columbia Business School professor Angela Lee shares what it was like to live in the midst of the tournament in New York City and New Jersey, and how mega-events drive innovation, strengthen infrastructure, reshape global perceptions, and even influence how athletes invest in their futures. Then, Toronto Star business reporter Josh Rubin digs into the numbers behind Toronto’s investment, questioning whether the economic benefits came close to the hundreds of millions of public dollars spent to host a mere six games. From civic pride and travel and tourism to venture capital and the challenge of measuring return on investment, this episode asks a question any host city should consider before bidding on the next global sporting event. Is it worth it?
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    54 Min.
  • What Have We Lost? David Macfarlane on the Business of Modern Sports

    What Have We Lost? David Macfarlane on the Business of Modern Sports
    Jul 25 2026
    Sports have never been bigger—or more profitable. But has something been lost along the way? This week on Skin In The Game, John Cimperman and Tim O'Shei welcome acclaimed Canadian author David Macfarlane to discuss his latest book, On Sports. From the overnight explosion of sports gambling and billion-dollar revenues to a growing emphasis on entertainment over athletic excellence, Macfarlane claims that today’s sports have fundamentally changed fan experience. The conversation explores why sports continue to unite communities, the tension between tradition and commercialization, the role athletes play in today's culture, and whether it's still possible to preserve the authenticity that made people fall in love with sports in the first place. Part memoir, part cultural commentary, and part sports business discussion, this episode asks a timely question: Can sports continue to grow without losing their soul?
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    48 Min.