In this episode, I share a pivotal moment from 2011 that changed the course of my career. At 29 years old, still finding my footing as an entrepreneur, I was balancing a motorcycle parts business with my growing aspirations in the entertainment industry. Little did I know, the chance to connect the dots between motorsports and showbiz would come during Monterey Car Week—and it would come in the form of a legendary encounter with Jay Leno.

As I attended the prestigious Concorso Italiano unveiling, the buzz was all about Jay’s arrival. This wasn’t just any celebrity encounter for me; my uncle, Nick Sanborn, had been a beloved figure in the racing world, and Jay had once mentioned him on his talk show. I knew this could be my moment, and when I approached Jay, I never expected what would happen next. After a brief conversation about my uncle, Jay invited me to join him on set for an interview at Jay's Garage.

What followed was an unforgettable experience. I got to witness the magic of Jay's show firsthand, standing just inches away as he filmed a segment on a 1967 Lamborghini. It was a lesson in humility, passion, and what it means to be grounded in success. Years later, I even found myself as the subject of one of Jay's jokes at his comedy show—a humbling reminder of how far I’d come.

This encounter with Jay Leno taught me that opportunities often come when you least expect them. It wasn’t about forcing my way into the entertainment world—it was about being genuine, ready, and open to learning from those who have walked the path before you.

Listen now to hear the story of how a single, unexpected encounter with Jay Leno shaped my journey, and how you can apply the same lessons of humility, timing, and seizing opportunities in your own path—whether in entertainment, business, or life.