What happens when a Hall of Fame left tackle takes everything he learned in the NFL and applies it to business, leadership, and life after football?

In this episode of The Dealmaker’s Lounge, Jeff Novak and Cody Davis sit down with Tony Boselli — Pro Football Hall of Famer, former All-Pro offensive tackle for the Jacksonville Jaguars, healthcare and real estate entrepreneur, and Executive Vice President of the Jaguars — to unpack what it really takes to win on and off the field.

Tony shares the real story behind the highlight reel: growing up in a big, tight-knit family, watching his dad grind from McDonald’s manager to owning 22 franchises, choosing USC for reasons that had nothing to do with football tradition, and eventually marrying Miss California. He opens up about bad investments, near-disaster financial moments, and the bathroom conversation with his wife that became a turning point in his life.

You’ll hear how he:

• Learned to bet on people first, not just ideas or deals

• Turned a failed venture into a launchpad for a healthcare and health-tech career

• Built a company that delivered flu vaccines to kids across multiple states

• Now helps engineer a “intangibly rich” roster and culture inside the Jacksonville Jaguars

• Uses adversity as fuel — welcoming it instead of fearing it, and leaning on faith, family, and work ethic to get through it

If you’re an operator, investor, founder, or leader trying to navigate risk, pick the right partners, and build teams that can take a punch and keep moving forward, this conversation is for you.

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