288: Across America with Chad Caruso
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288: Across America with Chad Caruso
Episode 288: Show Notes
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.
Key Points From This Episode:
From Rock Bottom to Redemption: Chad shares how a second DWI charge became the wake-up call that led to his sobriety.
Finding Purpose After Hitting Reset: How paying off $10,000 in legal fees and leasing an iPhone kickstarted Chad’s YouTube journey.
Raised Around Eastern Wisdom: Growing up with parents influenced by Buddhism and Eastern philosophy helped shape Chad’s resilience.
Dropping Out but Finding His Path: Chad talks about leaving school at 16 and how skateboarding became his chosen form of self-education.
Sobriety Without a Program: Why Chad chose to get sober without AA, and how full accountability became his guiding principle.
Building a YouTube Channel From Scratch: How Chad grew his YouTube by offering in-depth, no-fluff skateboarding tutorials that filled a gap online.
Discovering His True Audience: Why Chad’s content ended up resonating more with older skateboarders rekindling their passion.
50 Tricks in 50 States Challenge: How a daily vlog series across all 50 states helped build Chad’s community and sharpened his storytelling.
Skating Across America: The Ultimate Test: Chad details what it took mentally, physically, and spiritually to skateboard over 3,000 miles solo.
The Pain and the Process: From plantar fasciitis to worn-down wheels, Chad talks about the brutal toll the journey took on his body.
Silence as a Teacher: Why skating for hours alone in silence became one of the most powerful aspects of Chad’s transformation.
Unexpected Connections on the Road: How strangers, sobriety veterans, and fellow skaters made the journey across America more meaningful.
Quotes:
"Every choice I made led me exactly to where I was—nobody else was responsible but me." — Chad Caruso
"The lessons you learn from mastering one thing can be applied to anything in life." — Chad Caruso
"Silence strips away the distractions and shows you what you really need to face." — Chad Caruso
"I didn't want to just take from skateboarding anymore—I wanted to give back." — Chad Caruso
"Sometimes you don’t know if something will work out—you just have to trust that it will." — Chad Caruso
"I wasn’t skating across America to prove anything. I was doing it because I said I would." — Chad Caruso
Links Mentioned in Today’s Episode:
Website: ChadCaruso.com