The Human Adventure

#185 - Before longboards hit storefronts and GoPros hit helmets, Jack Smith and two friends pointed a 1969 Firebird toward the horizon and skated into history. Jack Smith talks about how a simple leapfrog relay turned a wild idea into the first recorded skateboard crossing of the United States—and how that journey shaped everything that came after.

We trace the arc from clay “crumble” wheels to first‑gen urethane and on to the big trucks and 70mm wheels that made 1980s distance skating faster and safer. Jack breaks down the daily cadence—early pushes, midday pool stops, evening miles—and the small-town moments that still stick: a Minnesota marquee that read “Welcome skateboarders,” a West Virginia diner that wasn’t sure what to make of three long‑haired kids, and strangers in Ohio who handed over house keys and dinner plates without hesitation. He tells the story that stays with him most: a rain delay at Yellowstone, a missed geyser, and a roadside rescue that, decades later, circled back through a single email to confirm a life saved.

We also explore how purpose and technology reshaped the ride. Jack’s 2003 crossing raised awareness for Lowe syndrome after the loss of his son; his 2018 electric skateboard traverse with his wife leading a camper van turned battery swaps into a moving pit crew. Along the way, he argues for the slower road—South Dakota’s rolling Highway 212, atlas pages over pure GPS—and why the “real America” lives beyond freeway exits. Jack shares updates on his feature screenplay and novel, plans for a 50‑year retrace in an electric VW, and a shout‑out to the new generation of cross‑country pushers proving that momentum beats perfection.

Hit play to learn how to design a relay that works, dial your long‑distance skate setup, and rethink what’s possible when you stop waiting for perfect conditions. If this conversation moves you, follow the show, share it with a friend, and leave a review to help more curious listeners find the road. Which back road would you choose next?

To learn more about Jack give him a follow on Instagram @jack_smith_morro_bay. 

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#184 - What does it take to conquer the American Ninja Warrior course? For Colton Skuster, the journey began as a 10-year-old jumping over exercise balls in his basement, dreaming of someday tackling those iconic obstacles himself.

At just 20 years old, Colton has already competed in three seasons of American Ninja Warrior, reaching the National Finals in Las Vegas and proving himself against competitors twice his age. His path wasn't straightforward – from training in a monkey costume to building his own backyard obstacle course during COVID lockdowns, Colton's determination never wavered.

During our conversation, Colton pulls back the curtain on what really happens behind the scenes at ANW. We discuss the intense application process where personality matters as much as athletic ability, the nerve-wracking experience of stepping onto the starting platform surrounded by cameras and crowds, and the surreal moment when producers reveal obstacle courses competitors have never seen before. You'll discover how competitors train for challenges they can't predict and the split-second decisions that determine success or failure on national television.

Beyond the competition itself, Colton shares profound insights about finding purpose after achieving a lifelong goal. "You reach one goal, you're satisfied, it's amazing, you celebrate," he explains, "and then you think – how can I take this further?" This wisdom has led him to mentor younger athletes, speak at high schools, and even caddy at Pebble Beach alongside celebrities like Michael Phelps.

Whether you're a fan of American Ninja Warrior or simply someone searching for motivation to pursue your own challenges, Colton's story demonstrates how passion, friendship, and resilience can transform dreams into reality at any age. Listen now, and discover how the journey matters more than the destination.

Be sure and give Colton a follow on Instagram @cwskuster.

Subscribe, leave a review, and follow @journeywithjakepodcast on Instagram to join our community of adventure seekers finding inspiration in extraordinary stories.

 Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#183 - Jamie Edwards returns to Journey with Jake with tales from the top of the world, having ventured to the Arctic with her 21-year-old daughter and 82-year-old stepfather. Their expedition through the Norwegian archipelago of Svalbard reveals a landscape where polar bears roam distant shores and massive glaciers calve with thunderous crashes that signal our changing climate.

Jamie vividly describes the unique challenges and thrills of Arctic exploration aboard the purpose-built Ultramarine ship. Unlike Antarctica (which Jamie visited previously), the Arctic's main attraction—and danger—is the magnificent polar bear. These apex predators can smell prey from up to 20 miles away and swim for days without stopping, facts that add a layer of respectful caution to every shore excursion. The expedition team constantly scans shorelines through powerful scopes before allowing passengers to disembark, ensuring both human safety and wildlife protection.

What makes this journey particularly special is the three-generation dynamic. For Jamie's environmentally-conscious daughter, seeing climate change impacts firsthand provided powerful context to her studies. For her adventurous 82-year-old stepfather, it was an opportunity he'd never have experienced otherwise. And for Jamie—someone who typically dislikes cold weather but couldn't resist the Arctic's allure—the expedition became another transformative travel experience, even culminating in the traditional "polar plunge" into frigid waters.

Beyond her Arctic adventures, Jamie shares updates on her expanding writing career, including contributions to National Geographic's upcoming "Traveler's Atlas" and her travel coaching services. Her website IamLostandFound.com continues to serve as both personal travel journal and professional portfolio, connecting her with opportunities to share her passion for thoughtful, transformative travel experiences.

Whether you're planning your own polar expedition or simply enjoy armchair adventures, this conversation offers both practical insights and philosophical reflections on how travel changes us—"you go into it one way, you come out of it another."

Be sure and check out Jamie's work on her website www.iamlostandfound.com. 

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#182 - Two simple questions changed everything for Bernard "Chalky" White. Growing up under the shadow of an abusive father who regularly beat both him and his mother, Chalky developed a survival mechanism that unfortunately led him to abandon his education completely by age 13. With zero qualifications at 16, he joined the police cadets and eventually became a London "Bobby," though his heart was never truly in law enforcement.

During his nine-year police career, Chalky witnessed unspeakable horrors, including a gruesome murder of a child and two near-death experiences where fellow officers failed to intervene. But fate intervened in late 1973 when a friend casually invited him skiing. Watching instructors and seasonal workers enjoying mountain life in Andora sparked something profound within him.

That's when Chalky stumbled upon two transformative questions that would guide his decisions forevermore: "What if I don't?" followed by "What if I do?" The emotional shift between considering negative consequences and positive possibilities gave him the courage to resign from the police force and pursue a completely different life.

The path wasn't straightforward. Chalky faced brutal rejection, including being told he would "never be a ski instructor" and later that his "wrong body shape" (bowed legs) made certification impossible. To fund his dreams, he sold encyclopedias door-to-door in Germany, managed a discotheque in Morocco, and took whatever jobs kept his skiing ambitions alive.

His persistence paid off. After failing multiple British certification attempts, he traveled to New Zealand where an instructor showed him how to adapt his technique to his physique. He passed on his first try and has spent decades teaching skiing, authoring the successful "Seven Secrets of Skiing" and recently publishing his memoir "Keep Chewing the Granite: How Two Questions Can Change Your Life."

Chalky's story demonstrates how asking yourself the right questions can completely transform your perspective and ultimately your life. What decisions might change for you if you asked yourself "What if I don't?" followed by "What if I do?" Try this simple but powerful technique today and see where it leads you.

To get a copy of Chalky's book check out Amazon! 

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#181 - Christian Ray Flores' life reads like an epic novel - a childhood marked by upheaval across continents, an improbable rise to pop stardom in Russia, and a profound transformation into a purposeful coach helping others discover their untapped potential.

Growing up amid political chaos, Christian experienced firsthand what most of us only read about in history books. By age seven, he had lived through a military coup in Chile that landed his father in a concentration camp, experienced refugee life under UN protection, and witnessed civil war in Mozambique. The constant relocations forced him to absorb four languages by age nine, unwittingly preparing him for a life bridging different worlds and perspectives.

When the Soviet Union collapsed around him just as he completed his economics degree, Christian made the unconventional choice to pursue music instead of academia. His gamble paid off spectacularly. Within years, he was performing in sports arenas across 15 countries, selling millions of albums, and even creating the campaign anthem for Boris Yeltsin's pivotal election against communist forces. Yet at the pinnacle of success, he found himself clinically depressed - a paradox that would later inform his coaching philosophy.

The turning point came through spiritual transformation and marriage to an American woman who saw past his celebrity to the person beneath. After transitioning to life in America, Christian discovered his calling as a coach for high-achievers who, like his former self, might appear successful on paper while feeling incomplete or imbalanced within.

His unique approach helps clients recognize when they're "fighting with one hand tied behind their back" - achieving impressive results while leaving their most powerful gifts dormant. Through his Exponential Life coaching program, he helps entrepreneurs, executives, and creatives untie that second hand and experience breakthrough performance aligned with their deepest purpose.

What makes Christian's perspective so valuable is that he's lived at both extremes - from refugee facilities to celebrity mansions, from communist oppression to American opportunity. This journey fueled his book "Little Book of Big Reasons to Love America," which offers a refreshing immigrant perspective on American possibility in an age of cynicism.

Want to discover what might be dormant in your own life? Connect with Christian's coaching programs and begin your own journey toward exponential growth and authentic purpose.

To learn more about Christian's coaching programs and his book check out his website xponential.life. You can also follow him on Instagram @christianrayflores.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#180 - Have you ever wondered what happens when a deep love for Ireland, masterful storytelling, and biblical foundations merge? That's exactly what unfolds in this captivating conversation with John Leonard, the creative mind behind the Wayfinder series – a fantasy adventure saga that bridges ancient myths with biblical narratives.

Growing up in rural Colorado as the eldest of four siblings, John shares how his close relationship with his brother shaped his early years through sports and friendly competition. His journey took a fascinating turn in college when he discovered rugby, serving as team captain for four years at Colorado Mesa University. This passion later connected him deeply to Irish culture when he seized an opportunity to study abroad in Belfast.

John's eight-mile walk from Dublin to the Neolithic site of Newgrange became a transformative experience, allowing him to absorb Ireland's countryside in a way impossible from behind a car window. "Walking that road was just something else," he recalls, describing how the sideways rain, winding paths, and ancient hamlets with thatched roofs transported him through time. His vivid descriptions of Irish pub culture – where storytellers gather, musicians spontaneously form bands, and strangers share life stories over shared drinks – reveal how deeply Ireland's storytelling tradition influenced his own writing.

The heart of our conversation explores John's Wayfinder series, particularly his first book "Dawn of Destiny." This unique fantasy saga fills the narrative gap between the Tower of Babel and Abraham's story in Genesis, weaving together Mesopotamian, Akkadian, Egyptian, and other Bronze Age cultural myths into a cohesive narrative that respects biblical accounts. Using the rabbinical teaching method of Pardes, John creates stories with multiple levels of meaning – from surface-level adventure to deeper theological symbolism.

Whether you're fascinated by ancient mythology, interested in creative approaches to biblical narratives, or simply love a good conversation about the writing journey, John's story will inspire you to see adventure as more than just reaching a destination. As he beautifully puts it: "The adventure is the journey in between...the relationships, the foundational aspects that form who you are along that journey." Subscribe now and join us for more inspiring conversations about overcoming life's challenges through adventure!

To learn more about John give him a follow on Instagram @thewayfinderseries and get a copy of his book on Amazon.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#179 - Lesa Burgess never imagined that falling in love with a basketball player would lead her across nine countries over eleven years, building a family of seven while navigating cultural labyrinths few Americans ever experience. Her memoir "Behind the Bench" pulls back the curtain on what looks like a glamorous life to reveal something far more compelling—a story of resilience, adaptation, and finding yourself when everything familiar has been left behind.

From giving birth in Turkey with no pain medication (total hospital bill: $275) to teaching her 6'11" husband how to drive a stick shift in Ukraine while pregnant, Lisa's adventures defy conventional understanding. "People are kind of like, 'Oh, this sounds so glamorous and amazing,'" she explains, "and you're just like, 'You have no idea what this is.'" Her stories traverse the spectrum from terrifying (being locked out of her apartment with no way to communicate) to triumphant (surprising her husband at championship games despite seemingly impossible logistics).

What resonates most powerfully is Lesa's journey from college soccer player with a clear identity to finding purpose in a supporting role that often left her feeling invisible. "It was hard for me to feel seen when people were constantly asking me about Chris and his career," she admits. The transformation wasn't immediate—it took years of introspection to recognize the vital importance of her contributions. "I started feeling like his successes were also mine," she shares, a perspective that became crucial to navigating their unconventional life together.

Throughout these challenges, faith served as Lisa's anchor, especially during the many times Chris was traveling while she managed their growing family alone in foreign countries where she couldn't speak the language. Her experience offers wisdom for anyone facing unexpected turns: "You are strong enough... It's going to be messy, it's not going to look like the path that you see in your head, and that's okay."

Ready to experience this extraordinary journey for yourself? Grab Lesa's memoir "Behind the Bench" on Amazon or at BehindTheBenchBookstore.com and discover how adventure, when embraced with courage and faith, transforms challenges into the most meaningful chapters of our lives.

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#178 - The road to redemption isn't always straight, and nobody knows this better than Garr Russell. From sitting in a jail cell in fifth grade to building a nationwide RV rental franchise with 70 locations, Garr's journey proves that our darkest chapters can become the foundation for something beautiful.

After his parents' divorce set him on a troubled path, Garr spiraled through expulsion, dropping out, and eventually dealing drugs. Rock bottom came with multiple arrests, but transformation arrived in an unexpected form – a coworker who simply asked him to read the Bible aloud during their shifts. This small invitation sparked a profound spiritual awakening that completely redirected Garr's life.

Years later, when an anniversary gift of an RV for his pregnant wife didn't quite land as expected (she left the campground early!), Garr's entrepreneurial mind saw opportunity. Fireside RV Rental was born, built not by purchasing a fleet of vehicles but by managing other people's assets – a brilliant model that allowed rapid growth without massive debt.

The RV lifestyle eventually became more than business for the Russell family. Following a challenging situation with one of their children, they hit the road full-time for five years, homeschooling their four kids along the way. Their adventures created lasting memories, but Garr's favorite wasn't at some grand national park – it was sitting beside a small river, making stick boats with his children, completely disconnected from life's pressures.

Garr has documented his journey in two books and continues to expand his entrepreneurial vision, recently purchasing a historic diner in his Florida town. Through it all, he maintains that "life happens for you, not to you," turning painful experiences into purpose. His mission now? Serving Christian entrepreneurs and supporting his family in fulfilling their unique callings.

Whether you're facing your own crossroads or simply love stories of radical transformation, Gar's journey reminds us that our past doesn't dictate our future – and sometimes the most meaningful adventures happen when we're brave enough to change direction.

To learn more about Garr, his books and Fireside RV Rental check out www.firesidervrental.com and www.myhisstory.com.

 Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#177 - What happens when childhood play transforms into serious sport? In this eye-opening conversation, we saddle up with Kht Shetty, a 20-year-old Polish hobby horse competitor and coach who's redefining what it means to "horse around."

Hobby horsing—a sport where participants jump obstacles up to 1.3 meters high while carrying handcrafted stick horses—combines athletic prowess, creative craftsmanship, and equestrian rules into something truly unique. Shetty walks us through this fascinating world, from its Scandinavian origins to the international competitions she now hosts. With remarkable maturity, she explains how the sport mirrors traditional equestrian events like show jumping and dressage, requiring serious training and physical preparation.

What's particularly striking about Shetty's journey is her resilience in the face of online criticism. Despite facing cruel comments and even death threats simply for participating in this harmless activity, she remains focused on nurturing the community, especially younger hobbyists who look up to her. The moment she realized her impact—when children lined up for her autograph at a Czech Republic event—stands as a powerful testament to how seemingly niche pursuits can create meaningful connections.

Beyond the jumps and competitions, hobby horsing has provided Shetty with entrepreneurial opportunities, leadership skills, and a global community. Her story challenges our assumptions about play and sport while demonstrating how passion, when pursued authentically, can transform both individual lives and communities. Whether you're an equestrian enthusiast or simply curious about unconventional paths, this conversation will have you reconsidering the power of play in our lives.

Ready to see hobby horsing in action? Follow Shetty on Instagram @kht_shetty and discover this remarkable sport for yourself!

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure. 

#176 - What does it take to sail around the world? For Alison Gieschen, it's required facing her worst fears while clinging to a dream she's had since childhood. From the moment she and her husband Dan met at a sailboat race and discovered their shared ambition to circumnavigate the globe, their path was set – though hardly smooth sailing.

Alison's journey began far from any ocean, on a 100-acre farm in upstate New York where she developed her first great passion: horses. Rising to elite competitive levels and eventually building her own equestrian vaulting program that became the largest on the East Coast, she never imagined trading stable ground for the unpredictable waves. Yet when she met Dan, something clicked. After just one weekend together, they recognized in each other the perfect sailing partner, and soon after, life partner.

Now seven years into their global circumnavigation, Alison shares harrowing tales that would make most people head straight for land – surviving "The Perfect Storm" with 20-foot waves that ripped equipment from their boat, enduring five catastrophic failures during a Pacific crossing, and facing a tsunami just days after reaching French Polynesia. Through it all, she's maintained her creative spirit, writing prolifically across genres from sailing memoirs to horse novels to children's books about mermaids.

What makes Alison's story particularly compelling is her honesty about fear. Despite visiting nearly 50 countries by sea, she calls herself "the bravest chicken on the planet." This paradox captures something essential about courage – it's not fearlessness but perseverance despite terror. When their first ocean crossing went terribly wrong, a chance encounter with her sailing mentor provided the perspective she needed: surviving your worst fears is actually a gift that proves you can handle anything.

Whether you're dreaming of distant horizons or simply looking for inspiration to face your own challenges, Alison's adventures remind us that, as she puts it, "Life is what you make of it, and if you have a dream, you need to go for it, because life's too short not to."

To learn more about Alison and get her books check out www.alisongieschen.com.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake 

Discover the journeys that do more than take you somewhere new—they change the way you see yourself and the world. Wayfinder Life-Changing Travel explores unforgettable adventures, hidden places, and the transformative power of stepping beyond the familiar.

Check out Wayfinder Life-Changing Travel and listen wherever you get your podcasts.

Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure.