Before Chad Caruso set a Guinness World Record for skateboarding over 3,000 miles across America, before the viral YouTube channel and the documentary, there was a broken-down car at 4 a.m., a failed breathalyzer, and a man staring down the barrel of a second DWI charge and possible jail time. That was Chad’s rock bottom—a wake-up call that pushed him to turn his life around.
In this episode of The Light Watkins Show, Chad shares the raw, unfiltered journey of how that moment sparked his sobriety, how paying off $10,000 in legal fees with a minimum wage job set him on a path of accountability, and how leasing an iPhone kickstarted his YouTube career teaching skateboarding. But this isn’t just a story about skate tricks and social media growth—it’s about discovering purpose, self-mastery, and the power of committing fully to something you love.
Chad opens up about what it really took to skateboard coast-to-coast without a support vehicle—just him, his board, and the open road. From averaging 55 miles a day to icing his battered feet in hotel sinks, to facing his fears of wild animals, silence, and exhaustion, Chad talks about the mental, physical, and spiritual grind of chasing a big, audacious goal.
You’ll hear how his upbringing around Eastern philosophy and Buddhism quietly shaped his resilience, how sobriety unlocked new levels of self-awareness, and how the road tested him in unexpected ways. Chad also shares why community became a surprising highlight of the journey, with strangers showing up to support him in meaningful ways.
Whether you’re in recovery, chasing a big dream, or just curious what it takes to do something extraordinary, this conversation is an inspiring reminder that you’re more capable than you think.
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