Always an Athlete Podcast

Jonathan Osborne

Welcome to the Always an Athlete Podcast with Jonathan K. Osborne, a conversation on competition in sports, business, law, and leadership. The show features interviews with coaches, athletes, and leaders across the spectrum who know that, at your best, you are ALWAYS an ATHLETE. Also available on YouTube: https://www.youtube.com/@alwaysanathletepodcast About the Host: Jonathan is a Florida business lawyer and trial athlete, representing people and businesses facing complex challenges and threats to their livelihood and freedom.

Episodes

  1. 11/21/2025

    University of Florida Head of NIL (Name, Image and Likeness) - Ben Chase on the evolution of sports, business, and NIL

    In this episode of the Always an Athlete podcast, Ben Chase, the Director of NIL Strategy at the University of Florida, discusses his role and the evolving landscape of college athletics. He shares insights on the recent partnership with Chipotle, his daily responsibilities, and the challenges and opportunities presented by NIL legislation. Ben reflects on his unconventional journey to his current position, the implications of ongoing NIL litigation, and the financial dynamics shaping the future of college sports. He emphasizes the importance of competition, overcoming adversity, and the legacy he hopes to leave at UF. The conversation concludes with a call for community support for UF athletics. Ben Chase is the Director of NIL Strategy at UF.The Chipotle partnership provides significant benefits to UF athletes.NIL has changed the landscape of college sports dramatically.Ben's journey to his current role was unconventional and inspiring.NIL litigation is ongoing and has many implications for athletes.Financial dynamics in college sports are shifting due to NIL.Competition drives personal growth and development.Adversity can lead to greater resilience and success.Legacy is about giving your all and supporting others.Community support is crucial for the success of UF athletics. About the Podcast Welcome to the Always an Athlete Podcast with Jonathan K. Osborne, a conversation on competition in sports, business, law, and leadership. The show features interviews with coaches, athletes, and leaders across the spectrum who know that, at your best, you are ALWAYS an ATHLETE.

    33 min
  2. 11/21/2025

    Val Ackerman, Commissioner of the Big East Conference and Founding President of the WNBA on her legendary sports journey, the Dream Team, WNBA and the Big EAST

    In this episode of Always an Athlete, host Jonathan Osborne interviews Val Ackerman, the fifth commissioner of the Big East Conference and the founding president of the WNBA. Val shares her journey from being a young athlete in the 60s and 70s to becoming a prominent figure in sports management. She discusses her experiences with the Dream Team, the challenges and triumphs of launching the WNBA, and her leadership style. Val also reflects on her role in the Big East Conference, the importance of supporting women's athletics, and offers valuable advice for young professionals looking to make their mark in the sports industry. Val Ackerman's journey in sports began with a supportive family.The Dream Team experience was a pivotal moment in her career.Launching the WNBA was a significant achievement for women's sports.Leadership in sports requires adaptability and strong communication skills.The Big East Conference has evolved significantly under her leadership.Val emphasizes the importance of education and hard work for young professionals.Building relationships is crucial in the sports industry.Val's leadership style is influenced by her mentors, including David Stern.The future of college athletics is uncertain, but the Big East is well-positioned.Supporting women's athletics is essential for the growth of the sport.About the Podcast Welcome to the Always an Athlete Podcast with Jonathan K. Osborne, a conversation on competition in sports, business, law, and leadership. The show features interviews with coaches, athletes, and leaders across the spectrum who know that, at your best, you are ALWAYS an ATHLETE.

    51 min
  3. 11/21/2025

    Luke Kurtz, Micah Kurtz, and Brian Meagher from Oak Hill Academy's Leadership Team discuss their vision for Oak Hill, the evolution of college basketball, and Oak Hill's legacy

    In the inaugural episode of the Always an Athlete podcast, host Jonathan engages with guests Luke, Micah, and Brian from Oak Hill Academy. The conversation explores their competitive upbringing in Buffalo, the importance of mentorship and leadership in sports, and how they prepare young athletes for future success. They discuss the impact of adversity, the significance of being coachable, and the legacy of notable athletes like Carmelo Anthony. The episode also highlights the new partnership with Paris Saint-Germain, expanding opportunities for student-athletes. Throughout, the guests emphasize the importance of dreaming big and surrounding oneself with supportive individuals. The competitive spirit from childhood shapes professional life.Mentorship is crucial in sports and personal development.Adversity can drive individuals to achieve greatness.Being coachable is essential for success in sports and life.Surrounding yourself with supportive people is key to growth.The importance of creating a positive culture in schools.Athletics can teach valuable life lessons beyond the field.Dreaming big can lead to unexpected opportunities.The role of coaches in shaping young athletes' futures is vital.Building a legacy involves impacting others positivelyAbout the Podcast Welcome to the Always an Athlete Podcast with Jonathan K. Osborne, a conversation on competition in sports, business, law, and leadership. The show features interviews with coaches, athletes, and leaders across the spectrum who know that, at your best, you are ALWAYS an ATHLETE.

    1h 15m

About

Welcome to the Always an Athlete Podcast with Jonathan K. Osborne, a conversation on competition in sports, business, law, and leadership. The show features interviews with coaches, athletes, and leaders across the spectrum who know that, at your best, you are ALWAYS an ATHLETE. Also available on YouTube: https://www.youtube.com/@alwaysanathletepodcast About the Host: Jonathan is a Florida business lawyer and trial athlete, representing people and businesses facing complex challenges and threats to their livelihood and freedom.