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.

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.

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.

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.

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?

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?

More than 400% growth in just five years. So how did a backyard game become one of the biggest business stories in sports?

This week on Skin In The Game, John Cimperman and Tim O'Shei welcome Rusty Howes, founder of Pickleball Channel, for an inside look at the explosive growth of America's fastest-growing sport.

From producing some of the sport’s earliest media coverage to documenting pickleball’s remarkable growth, Howes gives us the inside story of the game’s popularity and rapid expansion. They talk about private equity, media, professional tours, equipment manufacturers, and the role youth sports play in opening up new opportunities and growing pains for the sport.

The conversation wraps with a look at the future of pickleball and what comes next for an industry centered around a multigenerational model with building community as its north star.

What does it take to build one of the world's most recognizable sports brands?

This week on Skin In The Game, John Cimperman and Tim O'Shei welcome Bruce Popko, President of New Era Cap, the Buffalo-based company that has become a global leader in licensed sports headwear and apparel.

Popko discusses New Era's remarkable growth from a fourth-generation family business into a worldwide brand with operations spanning 16 countries and partnerships across every major professional sports league. He explains how the company's acquisition of ’47, an American lifestyle brand strengthened its position in the marketplace while allowing both brands to maintain distinct identities.

The conversation explores the intersection of sports, fashion and entertainment, including the evolution of licensed merchandise and celebrity collaborations, including the legendary story of Spike Lee asking for the creation of a red NY Yankees ballcap. They talk about product placement and how fans increasingly use apparel as a form of self-expression.

Popko also shares insights into emerging opportunities in college athletics, NIL, global expansion, golf, entertainment licensing and the future of sports merchandising as leagues, brands and media companies continue to collaborate in new ways.

What responsibility do athletes have beyond competition?

This week on Skin In The Game, John Cimperman and Tim O'Shei welcome Bruce Kidd, one of Canada's most celebrated distance runners, a former Olympian, scholar, author, and Officer of the Order of Canada.

Kidd reflects on his remarkable journey from a teenager discovering a talent for running in Toronto to representing Canada at the 1964 Tokyo Olympics. Along the way, he shares how sport became much more than competition, serving as a lens through which he explored politics, economics, culture, and social change. During his decades-long efforts to challenge racism, sexism, and inequality in sport, he experienced how athletes can use their platforms to create meaningful change and why sports remain one of society's most powerful mirrors.

Kidd also addresses two issues currently driving his advocacy work: the rapid expansion of sports betting and its impact on athletes and fans, and the ongoing debate surrounding sex testing and eligibility policies in international sport.

The episode concludes with a discussion of Kidd's memoir, A Runner's Journey, which chronicles his athletic career, academic work, and lifelong commitment to making sport more inclusive and equitable.

What does it take to turn a passion for sports into a career?

This week on Skin In The Game, John Cimperman and Tim O'Shei welcome Dr. Lynn Lashbrook, founder and president of Sports Management Worldwide, a global sports education company that has helped more than 30,000 graduates from 164 countries pursue careers throughout the sports industry.

Lashbrook shares his remarkable journey from athlete, coach, and university administrator to sports agent and entrepreneur, explaining how a chance encounter with the early internet and the release of Jerry Maguire helped inspire a business that has connected aspiring sports professionals with opportunities around the world.

Unlike traditional sports management programs, Sports Management Worldwide delivers its curriculum entirely online through courses taught by industry professionals in sports. Lashbrook explains how the organization's global classroom model connects students from around the world with executives, agents, scouts, broadcasters and analysts, creating opportunities that extend far beyond a traditional campus experience.

Lashbrook also offers an insider's perspective on Name, Image and Likeness (NIL), calling it one of the most significant transformations in modern sports. He discusses how NIL is creating new opportunities for athletes, families, advisors and aspiring sports professionals while reshaping college athletics.