Shred America: 950 Miles from Chicago to NYC by Skateboard with Mike Kosciesza
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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Watch Shred America
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900 Miles Biking (With No Clothes, Money or Bike!)
Cross Country Canoeing: 7,500 Miles Into the Soul of America + an Unconventional Life of Travel With Neal Moore
Walking the World with Alexander Campbell and Tom Turcich
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52:05
Brilliant Baltimore: Top 7 Hidden Gems (Why You Need to Visit This City) with Brian Oliver
What makes Baltimore, Maryland, one of the best US cities to visit?
Brian Oliver is the founder of BMore See More, a nonprofit organization empowering minority male students in Baltimore City to become local and global leaders through education, mentorship, and travel. A seasoned traveler who’s visited over 60 countries, Brian always finds himself returning to Baltimore and has become a voice for reframing how people see his home city by highlighting the stories, neighborhoods, and experiences that show its full heart and charm.
In this episode, Brian shares his list of seven hidden gems in Baltimore and gives us a local’s perspective on what makes the city so magnetic.
If Baltimore isn’t already on your travel radar, this conversation may change that. Brian gives us a tour of the city’s most vibrant spots, from the best place to watch fireworks to where you can get lost in local food culture. He talks about how neighborhoods shape identity, why steamed crabs are more than a meal, and how seeing the world has deepened his love for home. You’ll leave this episode with a fresh sense of what makes a city truly worth exploring and how travel can spark both global and local change.
What’s one city that surprised you in the best possible way, and what made it so memorable? I’d love to hear about it, and I hope you’ll share by sending me an audio message.
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Tune In To Learn:
How a childhood of road trips sparked his lifelong love of travel
What makes Baltimore’s people so memorable to visitors
Why the neighborhoods are the heart of the city, and how to explore them
Advice to get the most out of your first crab feast (and why it’s more than just a meal)
Why Camden Yards changed the game for stadiums across the U.S.
The local museum that tells 400 years of African American history in Maryland
How to use the water taxi like a local and why everything is better from the water
Where to find authentic food, murals, music, and community in Charm City
How travel inspired Brian to launch BMore See More for youth empowerment
And so much more
Resources:
Join Zero To Travel Premium Passport
Sign up for our FREE newsletter
Plan your trip to Baltimore
Visit Brian’s website
Learn about BMore See More
Follow Brian on Instagram
Want More?
Only in Wisconsin
5 Reasons To Visit The Florida Keys
9 Best United States Museums and Advice for Fostering Your Creativity with Bob Eckstein
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No Fixed Address - Listen to No Fixed Address, a travel podcast that’s your backstage pass to the world's hidden gems.
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1:03:56
Hiking the West Highland Way in Scotland with Lynne Nieman
What adventures have you been dreaming up but haven't done yet?
Lynne Nieman is the founder of Wander Your Way, a podcast and website dedicated to helping you explore off-the-beaten-path destinations throughout Europe. As a professional travel planner, Lynne combines her passion for Europe and off-the-beaten-path exploration with her expertise in creating personalized travel experiences.
In this episode, Lynne shares her experience hiking the West Highland Way in Scotland - what the trail is like, how to prepare for it, and why this iconic hike is well worth adding to your travel list.
She walks us through the mental and physical challenges of solo hiking, the beauty of trail life, and how she handled the unexpected. We talk about the deeper lessons that emerged from letting go of perfection to embracing a slower, more personal pace. You'll also hear about Lynne's plans for making a living with travel, how a trip to Europe changed both of our lives, and more.
What is in your travel box? What does the experience look like? 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 giving yourself permission is half the battle to pursuing your passions and creating your future
What made Lynne fall in love with Europe and what makes walking one of the best travel experiences
Logistics for hiking the West Highland Way, including when to go, how to prepare, and costs
Why it's important to tailor the hike to your needs
How this experience reshaped her relationship with travel and self-trust
Her favorite stories from the trail
How creating a "box" for your trip can be a fun and rewarding way to design your travels
And so much more
Resources:
Join Zero To Travel Premium Passport
Sign up for our FREE newsletter
Find Lynne on her website
Listen to Wander Your Way
Follow Lynne on Facebook, Instagram
Walker Ways
West Highland Way website
Want More?
You're Coming Hitchhiking Around Scotland With Me
Hitchhiking Stories From Scotland
Ireland: Travel, Music, and History w/ Garvan Rushe
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Visit Baltimore - Start planning your visit to Charm City today!
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No Fixed Address - Listen to No Fixed Address, a travel podcast that’s your backstage pass to the world's hidden gems.
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1:04:39
Lifestyle Design 2.0: What it Means in 2025 with Travis Sherry
Almost two decades after The 4-Hour Workweek was published, what does lifestyle design look like now, and where is it headed next?
Travis Sherry is a longtime traveler and entrepreneur who’s spent over a decade building a life centered around freedom, travel, and location independence while helping thousands of others do the same. He’s the founder of the Extra Pack of Peanuts blog and podcast, co-founder of the Location Indie community, and co-creator of Camp Indie, an adult summer camp for digital nomads, entrepreneurs, and adventure-seekers.
In this episode, Travis and I explore the concept of lifestyle design and how it’s evolved since the early days of digital nomadism.
You’ll hear what lifestyle design really looks like in today’s world of remote work, shifting values, and growing responsibilities, and how our own definitions of freedom have changed over the years as dads, business owners, and travelers. We reflect on what still holds true, what no longer fits, and what it takes to stay aligned with what matters most as you design your own version of your “best” life.
How has your definition of freedom or success evolved over the years and what does your ideal lifestyle look like now? I'd love to hear about it, and I hope you’ll share by sending me an audio message.
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Tune In To Learn:
Why “lifestyle design” in 2025 is more about values than travel hacks or passive income
The surprising things we both no longer prioritize when it comes to freedom and success
What we’ve learned about redefining productivity, especially after becoming parents
What to consider if you’re feeling burnt out, uninspired, or out of sync with your goals
Why slow travel still wins out and how technology is sabotaging our freedom
How we both think lifestyle design will evolve in the next 5–10 years and where we see the movement going
The trade-offs to consider when designing a non-traditional lifestyle
Advice for anyone feeling stuck or questioning their current path
And so much more
Resources:
Join Zero To Travel Premium Passport
Sign up for our FREE newsletter
Visit Travis’ website, Extra Pack of Peanuts
Check out Location Indie
Come to Camp Indie
Tim Ferriss’ Ideal Lifestyle Costing
Want More?
Jason’s Travel Wish List (Come Along and Dream with Me) with Special Guest Host Travis Sherry from Extra Pack of Peanuts
How to Leverage Real Estate to Fuel Your Ideal Travel Lifestyle (5 Expert Strategies) With Travis Sherry
From Expat to Digital Nomad: Finding Your Travel Rhythm, Balancing Burnout, and the Digital Nomad Lifestyle with Kristin Wilson
Thanks To Our Sponsors
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Harvest Hosts - Use code TRAVEL20 for 20% off your Harvest Hosts membership.
No Fixed Address - Listen to No Fixed Address, a travel podcast that’s your backstage pass to the world's hidden gems.
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1:19:40
The Power of Death in Life with Gentle Rebel Bronnie Ware
What can thinking about death teach us about living life?
Bronnie Ware is an author, songwriter, speaker, and free spirit devoted to helping others find the courage to embrace life on their own terms and live without regrets. Her international bestselling memoir, The Top Five Regrets of the Dying, has been translated into 32 languages and has a movie in the pipeline. Bronnie spent much of her life traveling nomadically and now has a home base in rural Australia.
In this episode, we talk about what those final life lessons can teach us about living more freely, creatively, and intentionally, especially when it comes to crafting a life filled with meaningful travel.
This conversation is a reflection on what it really means to live life on your own terms. Bronnie shares how she embraced her creative self later in life, the lessons she’s learned from the dying, and the surprising relationship between death and joy. If you’ve ever struggled with self-doubt, felt stuck in the “wrong box,” or wondered how to start living more authentically, Bronnie offers wisdom that might just change the way you think. We also talk travel, belonging, and why courage is always rewarded, even when the outcome looks different than you expected.
What’s one truth you’ve learned through travel that continues to shape how you live today? 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:
How Bronnie went from banking to bestselling author and the process she followed to commit to writing a book
What a “gentle rebel” really is, and why it fits Bronnie so well
Why growing up on a farm led to her propensity for travel
How she launched on a creative journey and embraced her new identity later in life
How self-doubt shows up and what to do when it tries to stop you
How she reframes challenges through a soul-level lens
Why travel will help you get to know yourself in a different way and uncover what really makes you feel at home
How courage, even when it’s quiet or imperfect, always pays off
And so much more
Resources:
Join Zero To Travel Premium Passport
Sign up for our FREE newsletter
Visit Bronnie’s website
Get your copy of The Top Five Regrets of the Dying
Listen to Bronnie’s albums Songs For The Soul and Sun Showers
Want More?
What Happens When You Die? (Part One): A Journey to the Other Side with Peter Panagore
Lessons From Caring for the Dying and Bike Packing 18 Countries With Jerry Kopack
What Is “Happiness”? Discovering Meaning On The Silk Road w/ Will Rickard
Thanks To Our Sponsors
Unbound Merino - Use code ‘TRAVEL10’ to get 10% off your Unbound Merino order.
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✈️ The Zero To Travel Podcast has been downloaded 12+ million times and named a "Best Travel Podcast" by The Washington Post, Travel + Leisure, The Telegraph, and Forbes.
Packed with life-changing perspectives, inspiration, and practical advice for everyone from travel newbies to nomads, this podcast will give you everything you need to travel the world on your terms, regardless of your situation or experience. Welcome to our amazing global listening community!
Since 2013, "Travel Ambassador" Jason Moore from zerototravel.com has been picking the brains of adventurous people living an unconventional life on the road so you can discover new ways to travel endlessly.
Along the way, you'll get actionable advice and key resources that will improve your life AND help you travel more as we get down and dirty on topics like; starting and running an online business from anywhere, the best off-the-beaten-path destinations to visit, travel and work opportunities, gutsy budget travel strategies, surprising ways to earn free travel, the digital nomad life, unconventional travel based lifestyles, fun travel jobs, how to plan epic adventures, backpacking, remote work, how to take a gap year or a career break, 4-hour work week inspired topics, ex-pat life, slow travel, travel hacking, sustainable travel, human-powered adventures, trips worth planning, and everything in between.
Host Bio: Jason wandered the planet as a nomad for over a decade and spent 15+ years on the road as a tour manager in events/music, a seasonal adventure travel tour guide, and a digital nomad. Originally from the USA, he is now a dual citizen (Norway/USA) based in Oslo. He is obsessed with helping YOU explore our planet on your terms.
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