Skateboarding Across America with Chad Caruso

Wild Ideas Worth Living

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4.7 • 1.3K Ratings

🗓️ 11 November 2025

⏱️ 30 minutes

🔗️ Recording | iTunes | RSS

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Summary

Chad Caruso kicked off his wild idea in Venice Beach, California, with a skateboard and a goal: to cross the country on four wheels. Over 57 days, he pushed through deserts, mountain ranges, and extreme weather, ultimately landing in Virginia Beach, Virginia and setting a Guinness World Record for the fastest coast-to-coast skateboarding journey.

Transcript

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0:00.0	On March 23, 2023, Chad Caruso hopped on a skateboard in Venice Beach, California, and started riding.
0:12.4	His goal was to skate all the way across the country.
0:16.6	Along the way, Chad skated through the desert, over mountain ranges, and across the Great Plains.
0:22.2	He pushed through rain, extreme heat, and strong headwinds.
0:26.0	After 57 days, Chad arrived in Virginia Beach, Virginia, and set a Guinness World Record
0:31.8	for the fastest crossing of America on a skateboard.
0:35.9	It was kind of hard not to cry, like skating up to the finish line.
0:39.4	25 years of just all the falling and pain and everyone telling me to quit skateboarding,
0:46.0	and I dropped out of high school and not having a job.
0:49.0	It felt like all of that, like, culminating.
0:53.9	Chad grew up on Long Island and has been skateboarding since he was 14 years old.
0:58.5	He stuck with the sport through some major setbacks, including injury and addiction.
1:03.4	It took blood, sweat, and tears for Chad to overcome these challenges and to get to the
1:07.4	point where he could ride across the country.
1:09.8	But it ended up being the most fulfilling adventure of his life.
1:13.8	I'm Shelby Stanger, and this is Wild Ideas Worth Living,
1:17.6	an REI Co-op Studios production presented by Capital One and the REI Co-op MasterCard.
1:27.4	Chad Caruso, welcome to Wild Ideas Worth Living. I'm so excited to talk to a
1:32.2	skateboarder. Thanks for having me on. A Guinness record-breaking skateboarder. So how did you
1:38.6	get into skateboarding? And when you say, okay, so there's lots of different types of skateboarding.
1:43.5	What skateboarding do you prefer?
1:45.7	Like street skating, going to park, skating is a way of transport.
	...

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