Tom Henske is a former collegiate goalkeeper and three-time national champion at the University of Virginia whose path after soccer unfolded very differently than he expected. After recurring shoulder injuries brought his playing career to an end, Tom found himself facing the uncertainty of life beyond sport — eventually beginning a career in financial planning that would span more than three decades.

In this episode, Tom reflects on the lessons goalkeeping taught him about resilience, recovering from mistakes, and putting in the work when no one is watching. He shares how returning to soccer as a high school goalkeeper coach gave him an opportunity to mentor the next generation, and how those experiences ultimately sparked a deeper interest in helping young people understand money and prepare for life beyond athletics.

Now a professor of personal finance working with students and student-athletes at UVA, Tom has brought his career full circle. He helps athletes build the financial confidence and habits they can carry long after their playing days are over. Tom discusses financial literacy in the age of NIL, the importance of starting early, and why confidence with money can create greater freedom to pursue purpose and eventually, pay it forward.

Tom is also continuing to bring these ideas to a wider audience. His recently released TEDx Talk was selected as an Editor’s Choice by TED, furthering the conversation around financial literacy and empowering the next generation to build confidence with money.

Watch Tom’s TEDx Talk: https://www.youtube.com/watch?v=4GpcY-mAIRc

Connect with Tom: https://www.totalcents.com/about

This conversation is about navigating unexpected transitions, trusting the skills sport gives you, playing the long game, and finding meaningful ways to use what you've learned to help the people coming after you.

Shahar Biran is a former collegiate tennis player competing at Old Dominion University for undergrad, and then completing her MBA while finishing her final year of eligibility at the University of South Carolina. Like many international athletes, her transition to college athletics required adjusting not only to a new country, but also to a completely different style of competition — trading the independence of individual tennis for the dynamics of being part of a team.

After graduation, Shahar found herself navigating the uncertainty that often follows an athletic career. Inspired by her own experience of navigating the college recruiting process without much guidance, she now works with Momentum NYC, a recruiting agency that helps international junior tennis players pursue opportunities to compete and study in the U.S. Through her work, she now supports athletes through every step of the journey, from recruitment and academics to visas and settling into college life.

In this episode, Shahar reflects on the challenges of leaving competitive tennis behind, the unexpected feeling of missing the pressure and adrenaline of competition more than the sport itself, and how she has found a new outlet for that competitive energy by helping the next generation of athletes. She also shares her perspective on navigating cultural transitions, embracing life beyond sport, and learning to let go of the "all or nothing" mindset that once defined her athletic career.

Brett Stern is a former collegiate tennis player whose life revolved around pursuing excellence on the court from a young age. After training at one of the country's most elite tennis academies and competing at both UC Irvine and the University of Florida, Brett faced a reality many athletes encounter: letting go of the dream that had defined so much of his identity.

In this episode, Brett reflects on the difficult transition away from competitive sport, the loss of structure and purpose that followed, and the challenge of building a new life beyond athletics. He shares how the mindset that fueled his tennis career — resilience, problem-solving, discipline, and persistence — became the foundation for his success in business, where he has spent the last three decades working alongside his father in the family business.

Brett also discusses the importance of finding fulfillment in new pursuits, and learning that purpose can evolve over time. Through honest reflection and hard-earned perspective, he offers reassurance to athletes navigating uncertainty and reminds us that growth often happens long after the final match is played.