Two Super Bowl championships. Nine seasons in the NFL. And a second career as one of ESPN's most recognizable football analysts.

Booger McFarland joins Jim Pyne on On the Line for a candid conversation about football, leadership, adversity, and life beyond the game.

Booger takes us inside the legendary Tampa Bay Buccaneers defense, shares what made Tony Dungy and Jon Gruden successful in very different ways, and explains what he learned playing alongside Peyton Manning in Indianapolis.

He also opens up about walking away from the NFL at age 30, finding his way into broadcasting, and the advice that has stayed with him since he was 15 years old.

Plus, Jim and Booger discuss the changing quarterback position, NIL, the transfer portal, and the future of college football.

In this episode:

• The Buccaneers' championship culture and Hardy Nickerson's mentorship
• Tony Dungy vs. Jon Gruden
• What made Peyton Manning special
• Reinventing yourself after football
• How the quarterback position is changing
• Life lessons, parenting, and leaving a legacy

Presented by PLS Aviation.

Learn more at www.plsaviation.com.

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

BREAKING NEWS: Brett Yormark Announces Big 12 Departure — An Exclusive Conversation Recorded Before the Announcement

On the same day Brett Yormark's departure from the Big 12 Conference was announced, On the Line with Jim Pynepresents a special episode featuring one of the most accomplished and innovative executives in sports.

This conversation was recorded before the October 30, 2026 announcement that Yormark will step down as Big 12 Commissioner.

In this candid, wide-ranging interview, Yormark joins former NFL player and sports business executive Jim Pyne to reflect on his remarkable career, from selling tickets for the New Jersey Nets to becoming one of the most influential leaders in professional and collegiate sports.

Yormark shares stories and lessons from his time at NASCAR, where he helped secure a landmark $750 million Nextel sponsorship agreement; his leadership of the Brooklyn Nets; his experience working alongside Jay-Z at Roc Nation; and his efforts to stabilize, rebuild, and grow the Big 12 Conference.

Highlights include:

• His Big 12 legacy: How he helped transform the conference following the departures of Texas and Oklahoma.
• Leadership and career transitions: The importance of self-awareness, resilience, relationships, and knowing how to apply your strengths to new opportunities.
• Jay-Z and Roc Nation: What he learned about culture, branding, and connecting with younger audiences.
• The future of college athletics: His views on NIL, revenue sharing, the transfer portal, and College Football Playoff expansion.
• Lessons from great leaders: Advice from influential executives and entrepreneurs throughout his career.
• Leaving a legacy: In a particularly timely moment, Yormark discusses his desire to leave every organization better than he found it and how he hopes to be remembered.

With today's announcement, this previously recorded conversation offers a unique perspective on Yormark's leadership philosophy, accomplishments, and reflections on his career at a pivotal moment.

🎙️ On the Line with Jim Pyne — Conversations with leaders, coaches, athletes, and executives about the experiences, decisions, and lessons that shape success.

#BrettYormark #Big12 #CollegeFootball #SportsBusiness #Leadership #OnTheLineWithJimPyne

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

Super Bowl champion, Tampa Bay Buccaneers Ring of Honor member, and one of football's most passionate personalities, Jon Gruden, joins Jim Pyne for an unforgettable episode of On the Line with Jim Pyne.

Jim spent two years coaching on Gruden's staff with the Tampa Bay Buccaneers, giving him a firsthand look at the intensity, preparation, leadership, and relentless work ethic that helped define Gruden's coaching career.

In this candid conversation, Gruden takes us inside his football journey, from growing up in a football family to learning from legendary coaches Mike Holmgren and Al Davis. He reflects on his remarkable coaching tree, including Sean McVay, Kyle Shanahan, Mike Tomlin, and Raheem Morris, and shares what made those young coaches special.

The two also dive deep into the state of football today. Are we losing the art of developing quarterbacks? Gruden shares his strong opinions on modern offenses, running quarterbacks, the decline of traditional offensive line play, and why the game needs to get back to teaching fundamentals.

Beyond football, Gruden opens up about overcoming adversity, reinventing yourself, loyalty, mental toughness, and the importance of surrounding yourself with the right people.

And in a special moment, Gruden shares his thoughts on Jim's son, quarterback Michael Pyne, and his future in football.

Football. Leadership. Adversity. Family. Life lessons.

It's vintage Jon Gruden — passionate, insightful, entertaining, and unfiltered.

Don't miss this episode of On the Line with Jim Pyne.

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

NFL Commissioner Roger Goodell joins former NFL player and Wheels Up co-founder Jim Pyne for a rare, in-depth conversation on On the Line with Jim Pyne.

From his early days working as a bartender and bouncer to leading the most powerful league in professional football, Goodell shares his perspective on determination, leadership, adversity, family, and the future of the NFL.

In this episode, Jim and Roger discuss:

• The lessons that shaped Roger's leadership journey
• His mother's influence and the importance of family
• Navigating adversity and making difficult decisions
• The NFL's international expansion
• The growing opportunities for women in football and flag football
• Artificial intelligence and how technology could reshape professional sports
• The determination required to lead through change

It's a conversation about much more than football. It's about people, relationships, responsibility, and the future of the game.

Subscribe to On the Line with Jim Pyne for conversations with the most influential leaders in sports, business, and beyond.

Listen on Apple Podcasts, Spotify, and all major podcast platforms.

https://onthelinewithjimpyne.buzzsprout.com/

#RogerGoodell #NFL #JimPyne #OnTheLineWithJimPyne #Football #Leadership

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

NFL legend and Pro Football Hall of Famer Bruce Smith joins former NFL offensive lineman Jim Pyne on On the Line with Jim Pyne for a powerful conversation about football, family, perseverance, business, and the legacy we leave behind.

With 200 career sacks, 19 NFL seasons, four Super Bowl appearances, and 12 surgeries, Bruce Smith built one of the most remarkable careers in football history. But behind the records is a story of hard work, discipline, faith, and the people who helped shape him.

Two proud Virginia Tech Hokies reconnect as Bruce reflects on his journey from Norfolk, Virginia, to becoming the No. 1 overall pick in the NFL Draft and one of the most dominant defensive players the game has ever seen.

In this episode:

• The secret to Bruce's remarkable 19-year NFL career and all-time sack record.
• How his parents, coaches, and Virginia Tech shaped his work ethic and character.
• His memories of Virginia Tech and thoughts on the future of Hokies football.
• How he transitioned from the NFL into successful real estate development, including a billion-dollar casino and entertainment project in Petersburg, Virginia.
• Why Bruce believes the NFL must do more to provide lifetime healthcare for former players.
• His approach to overcoming adversity, seeking wise counsel, and staying grounded in faith.
• The powerful advice he received at Virginia Tech: "You don't work, you don't eat."
• What Bruce hopes people will remember about him long after his football records are broken.

Bruce also shares why relationships matter, how decisions made early in life shape your future, and why family, faith, and community mean more than individual accomplishments.

From the gridiron to the boardroom, this is a conversation about much more than football.

🎙️ On the Line with Jim Pyne — Real conversations with the people who have lived it, led it, and learned from it.

Subscribe, follow, and share for more conversations with legendary coaches, athletes, and leaders.

#BruceSmith #JimPyne #OnTheLineWithJimPyne #NFL #ProFootballHallOfFame #VirginiaTech #BuffaloBills #Leadership #Football

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

Frank Beamer joins On the Line with Jim Pyne for a personal conversation about leadership, loyalty, adversity, and the remarkable rise of Virginia Tech football.

Coach Beamer looks back on his journey from growing up in Virginia and playing at Virginia Tech to returning as head coach and building the Hokies into a national powerhouse. He shares the principles that shaped his career: tell the truth, earn trust, hire good people, embrace hard work, and never back down from adversity. Pasted text

Jim and Coach Beamer also revisit their own history, including Beamer recruiting Jim out of Milford, Massachusetts, the difficult 1992 season, and the breakthrough 1993 team that went 9–3 and won the Independence Bowl. They discuss Mike Gentry, Bud Foster, the origins of Beamer Ball, Virginia Tech’s legendary emphasis on special teams, and the relationships that made the program special. Pasted text

Beamer also talks about his family, his pride in his son Shane, and why he believes relationships and trust remain at the heart of successful football programs—even as college football continues to change. Pasted text

It’s a conversation between a legendary coach and one of his former players about far more than football—leadership, character, relationships, resilience, and building something that lasts.

Subscribe to On the Line with Jim Pyne for more conversations with the biggest names in football, sports, leadership and business.

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

Duke head coach Manny Diaz joins Jim Pyne on On The Line for a wide-ranging conversation about leadership, culture, adversity and a life spent in college football.

Diaz shares lessons from his journey through some of the biggest programs in the country, what he learned from the highs and lows along the way, and how those experiences have shaped the way he leads Duke today.

Jim and Manny talk about building trust with players, establishing a winning culture, developing toughness, handling pressure and why relationships remain at the heart of successful football programs.

It’s an inside look at the experiences and philosophy behind one of college football’s most respected coaches — and the lessons in leadership that extend well beyond the field.

🎙️ On The Line with Jim Pyne

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!

UCLA head coach Bob Chesney joins Jim Pyne on On The Line to talk about the journey that took him from Division III football to leading one of college football’s most recognizable programs.

Chesney shares the lessons he learned growing up in a football family, working his way through the coaching ranks, and building winning programs at Salve Regina, Assumption, Holy Cross and JMU before taking over at UCLA.

They discuss his four pillars for success—attention to detail, positive attitude, urgency and relentlessness—along with building trust, creating competition, developing players and why he believes there is no job too small. Chesney also explains his philosophy that failure doesn’t define you, it refines you, and shares the simple advice from his mother that has stayed with him throughout his career: “Grow where you’re planted.”

A great conversation about leadership, relationships, preparation and the process behind building a winning culture.

🎙️ On The Line with Jim Pyne

Support the show

Connect with Jim Pyne

Thanks for listening to On the Line with Jim Pyne.

If you enjoyed this episode, please follow the show, leave a rating and review, and share it with a friend. Your support helps us bring you more conversations with the leaders, innovators, and game changers shaping sports, business, and entertainment.

Follow Jim on LinkedIn and social media for updates on future episodes, behind-the-scenes content, and exclusive clips.

New episodes released often!