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In this deeply personal episode, John opens up about the two most influential money legacies in his life: his father, a relentless hustling businessman, and his mother, a disciplined hourly worker who quietly built lasting wealth.

Through their contrasting approaches—one fueled by entrepreneurship and hustle, the other by financial literacy, credit, and steady investing—John explores powerful lessons about success, failure, and the true keys to generational wealth.

From stories of family businesses, lost fortunes, and hard-won financial wisdom, John challenges listeners to rethink what it really takes to build stability and prosperity. Hustle may open the door, but strategy, stewardship, and smart money habits are what keep you in the room.

If you’ve ever wondered whether it’s better to grind as an entrepreneur or build steadily as an employee, this episode will change the way you look at money, wealth, and legacy.

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In this episode, John sits down with Tim Crockett — Chief Risk and Security Officer at Operation HOPE and former British Special Forces operator. From rowing 2,400 miles across the Pacific with his son, to recovering Osama bin Laden’s video library in Afghanistan, Tim’s life is a masterclass in resilience, risk management, and quiet strength. Together, they explore how protecting what you build — whether wealth, reputation, or family — is just as important as creating it. Discover the deep connections between security, mental health, financial stability, and the discipline required to not only survive, but thrive.

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