Shred America: 950 Miles from Chicago to NYC by Skateboard with Mike Kosciesza

2025-05-15

Would you skateboard nearly 1,000 miles across the U.S. with no real plan, just to see what would happen? Mike Kosciesza did just that with three friends and a dream to make a documentary out of it. Back in 2008, these four 20-year-olds set off from Chicago with their skateboards pointed toward New York City. A decade later, that wild ride became Shred America, a raw, DIY travel film packed with lessons they never saw coming. We’re digging into Mike’s adventure, the long road to making Shred America, and what it takes to turn a crazy idea into somet...

Would you skateboard nearly 1,000 miles across the U.S. with no real plan, just to see what would happen?

Mike Kosciesza did just that with three friends and a dream to make a documentary out of it. Back in 2008, these four 20-year-olds set off from Chicago with their skateboards pointed toward New York City. A decade later, that wild ride became Shred America, a raw, DIY travel film packed with lessons they never saw coming.

We’re digging into Mike’s adventure, the long road to making Shred America, and what it takes to turn a crazy idea into something real, especially when you don’t feel fully prepared.

Mike’s story is a reminder that you don’t always need a perfect plan to start something meaningful. You’ll hear about what it takes to follow through on a wild vision, the lessons that come with looking back on your younger self, and why doing something imperfectly can lead to your most unforgettable adventures. We also get into the unexpected challenges of documenting a trip like this, what it’s like to finish a film a decade after shooting it, and why a little rebellion can take you a long way.

Would you ever go on a trip without much planning, just to see where it leads? Or have you done something similar before? I'd love to hear about it, and I hope you’ll share by sending me an audio message.

*This is a previously released episode from the archives! Zero To Travel interviews are timeless, offering valuable insight whenever you listen.

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Tune In To Learn:

Why Mike and his friends decided to skate from Chicago to NYC in the first place
How picking a departure date changed everything
What went wrong with their original film plan, and how they adapted
How the team pushed through injuries, burnout, and zero navigation skills
Why a random guy in a bathroom helped save their trip
What it’s like editing a film of your 20-year-old self, ten years later
Advice to anyone dreaming up a bold idea but unsure how to start
How filming organically added authenticity (and chaos) to the journey
Why they turned down film festivals and opted for DIY distribution
How rebellion and risk-taking shaped their travel and creative paths
And so much more

Resources:

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