I sit down with Ferrari GT3 driver Custodio Toledo, whose journey into professional racing started not on the track but in business — after building and selling a software company, a spontaneous Ferrari purchase ultimately led him to compete in legendary endurance races like Le Mans and Daytona. We talk about the physical and mental demands of motorsport, how his business background shaped his approach to racing, and his perspective on luck, discipline, and surrounding yourself with the right people. We also dive into family, faith, purpose, and what it means to reinvent yourself later in life — a conversation about chasing goals, staying curious, and proving it’s never too late to pursue what once felt out of reach.

Follow Custodio’s IG: https://www.instagram.com/custatoledo/

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In this episode, I sit down with world-tour cycling photographer Harry Talbot to talk about life behind the lens — from shooting races like the Tour de France and living out of suitcases to chasing creative excellence without losing yourself in the process. Harry shares what it’s really like working inside professional cycling, the chaos most people never see, and what it takes to consistently create photos that make people stop and look twice. We get into identity, ambition, travel, nature, self-doubt, and the tension between wanting more while still trying to stay grounded. Harry opens up about the constant push to improve, the fear of losing that drive, and how creativity, career, and personal fulfillment all intertwine. This one’s about purpose, perspective, and figuring out what it actually means to love what you do while still becoming who you’re meant to be.

Follow Harry’s IG: https://www.instagram.com/visualsofharry/

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Robbie Deckard is a professional triathlete, coach, and someone I’ve gotten to know well over the last few years through shared training blocks, Tucson winters, and long conversations about sport and life. In this episode, we talk about everything from mustaches and dogs to Olympic dreams, burnout, self-coaching, and the quiet identity shifts that happen when you realize a decade has passed faster than you expected.

We dig into what it’s like to dedicate your life to endurance sport without the financial security people assume comes with being “pro,” how curiosity can both elevate and derail performance, and why so many athletes struggle when it’s time to let a version of themselves go. Robbie opens up about aging, purpose, family, writing a book, and what it means to build a life around being outside rather than chasing a single result.
Robbie’s SubStack: https://substack.com/@robbiedeckard?r=2d6gzd&utm_medium=ios&utm_source=profile&shareImageVariant=light

Robbie’s IG: https://www.instagram.com/robbie_deckard/

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