On Adventure Podcast with Josh Self

A podcast of conversations with the Everyday Explorer. Why do we pursue adventure and what do we find when we push past our limits? Buckle up and enjoy the ride as we go On Adventure.

Episode 81: Why We Need the Wilderness - Identity, Purpose & Soul Rest with Todd Pinkston 10/02/2026

Episode 81: Why We Need the Wilderness - Identity, Purpose & Soul Rest with Todd Pinkston Most of us are constantly adding something to our lives - a better routine, another goal, a new piece of technology, one more strategy for getting everything under control. Todd Pinkston has built an entire organization around doing the opposite. As co-founder of Wayforward Adventures, Todd takes adults into the Southern Colorado backcountry for four- and five-day backpacking trips where the phones and watches stay behind, the distractions disappear, and participants aren't even told what time it is. The idea isn't to conquer the biggest mountain or push people to their physical limits. It's to remove enough noise that they can finally pay attention to what's happening beneath the surface. In this episode of On Adventure, Todd shares how a single question on a backpacking trip - “If money wasn't an issue and you could do anything to make a difference in the world, what would you do?” - helped launch Wayforward Adventures. Todd and Josh explore the fear underneath entrepreneurship, why high performers can struggle to surrender control, and the surprising reason people return from the trail physically exhausted yet deeply rested. They also dig into one of Todd's most important ideas: the difference between living for your identity and living from it. Along the way, they talk about leadership, faith, family, discomfort, purpose, and Todd's newest adventure - training for his first 100K ultramarathon. In This Episode Todd and Josh explore: Why Wayforward is built around subtraction, not addition The question that changed the trajectory of Todd's life Wrestling with “Do I have what it takes?” Entrepreneurship, anxiety, and learning to lead from a healthier place Why surrendering your phone, watch, and schedule can be harder than carrying a backpack The difference between physical rest and “soul rest” How the wilderness strips away the personas we maintain at home Why intentionally choosing discomfort can prepare us for everyday life The role of vulnerability and community in lasting change Living from your identity instead of for it Why Todd sees purpose as a daily practice Training for his first 100K ultramarathon Episode Chapters 00:00 — Meet Todd Pinkston Wayforward Adventures and the idea of using the backcountry to reset priorities. 02:00 — Football, identity & the outdoors Todd's early search for identity and the mentor who introduced him to backpacking. 04:00 — Ministry through subtraction Why removing distractions can sometimes accomplish more than adding another program. 05:00 — The question that changed everything “If money wasn't an issue, what would you do?” 07:00 — Do I have what it takes? Fear, entrepreneurship, and launching Wayforward Adventures. 11:00 — When grinding stops working COVID, leadership stress, and Todd's realization that deeper internal work was needed. 16:00 — Why the wilderness works Discomfort, authenticity, and what happens when the facade starts to disappear. 19:00 — The idea of “soul rest” Why people can finish a backpacking trip physically exhausted but deeply rested. 22:00 — Giving up control No phones. No watches. No schedule. No need to know what's next. 27:00 — Why adults need adventure How life experience changes what people bring into—and take away from—the wilderness. 30:00 — Managing risk in the mountains Altitude, acclimation, guide training, and knowing when to turn around. 33:00 — Why community matters Going below the surface and building relationships that continue after the trail. 35:00 — Choosing the hard thing How voluntary discomfort can reshape our relationship with adversity. 38:00 — Todd's first 100K Why he signed up for an ultramarathon despite the fear of failing. 40:00 — Running without distractions Long, slow miles as a space for solitude, prayer, and reflection. 43:00 — When suffering has a purpose Knowing the difference between productive challenge and simply pushing too far. 46:00 — Young guides leading accomplished adults What 21- and 22-year-old guides learn about trust, judgment, and leadership. 49:00 — It's all about perspective Why the exact same trail can feel completely different to two people. 50:00 — The cost of entrepreneurship Todd opens up about stress, marriage, family, and the harder years of building Wayforward. 55:00 — Living FROM your identity The difference between doing meaningful work and needing your work to prove who you are. 58:00 — Unstuck and Alive Recognizing and unlearning the stories that drive our internal dialogue. 1:00:00 — Purpose is a practice Why purpose isn't something we discover once—it's something we continually live. 1:03:00 — Where to find Todd & Wayforward Memorable Moments “We don't give ourselves what we actually need. We give ourselves the comfort that we think we want.” Todd describes one of the biggest surprises of Wayforward: people return from several days of hiking and sleeping on the ground physically exhausted, yet they repeatedly say they feel rested. His explanation is that sometimes we need less physical rest and more soul rest—time when nobody needs anything from us and the phone isn't demanding our attention. Another question captures much of Todd's personal journey: “Am I living from my identity or am I living for my identity?” Living for identity means accomplishments continually have to prove something about us. Living from identity allows us to work hard without making the outcome responsible for telling us who we are. About Todd Pinkston Todd Pinkston is the co-founder of Wayforward Adventures, a Southern Colorado backpacking organization that takes adults into the backcountry for multi-day experiences centered on challenge, community, faith, and reflection. Todd's journey into the wilderness began in high school and continued through guiding backpacking trips in Southern Colorado. He launched Wayforward in 2014 after seeing firsthand how powerfully the backcountry experience could impact adults. What began with roughly 25 people on trail during the first summer has grown to hundreds of participants each year. Resources Mentioned — Multi-day guided backpacking experiences in Southern Colorado. — Todd Pinkston and Steven Neuner's book exploring identity, purpose, and the stories that shape our lives. Unstuck and Alive Podcast — Conversations centered on many of the same themes. Also mentioned: Arthur Brooks, David Brooks' The Second Mountain, and the Bear Chase 100K. Connect with Todd Wayforward Adventures: wayforwardadventures.com Email: The Takeaway Sometimes the next step isn't adding something. It's removing enough noise to hear what's already there. Todd's story is a reminder that adventure doesn't have to be about conquering the biggest mountain or proving how much discomfort we can endure. The wilderness can simply give us enough distance from everyday life to examine what is driving us, reconnect with who we are, and return home with a clearer sense of how we want to live. If you enjoyed this conversation, subscribe to On Adventure, share the episode with someone who could use a little less noise and a little more adventure, and join us for the next episode. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/43129203

Episode 80: Living Your Great Life Right Now with Monica 'Moss' Aguilar 09/18/2026

Episode 80: Living Your Great Life Right Now with Monica 'Moss' Aguilar What happens when you build your life around the things that make you come alive - not someday, but right now? Monica Aguilar, known on trail as “Moss,” is an artist, long-distance hiker, and everyday explorer who has intentionally built a flexible life around creativity and adventure. After graduating from UMass Amherst, she spent a season working in Alaska before thru-hiking the Appalachian Trail in 2018. Since then, she’s continued exploring on foot and by bike, including the Pacific Crest Trail and more than 3,000 miles on the Continental Divide Trail. In this conversation, Monica and I talk about what keeps drawing her back to long trails - the community, the challenge, the highest highs and lowest lows, and the chance to experience a place slowly rather than simply passing through it. We also get into fear and risk, including difficult snow travel on the PCT and the decision to change course in Colorado’s San Juans when challenge began moving beyond her comfort zone. But Monica’s story is also about designing a life around what matters. She’s built enough flexibility into her work, spending, and art business to disappear onto a trail for months at a time while still saving for what she calls “future Moss.” That philosophy overlaps beautifully with something I talk about often: living your great life right now without ignoring the future. We also explore the connection between adventure and Monica’s art. Through Chasing Trails Art, she creates murals, window paintings, and nature-inspired work influenced by the places she encounters along the way. Even there, she finds another version of doing hard things - the uncertainty and struggle of creating something that didn’t exist before. Episode Highlights 00:00 — Meet Monica Aguilar: artist, thru-hiker, and unconventional career builder 08:30 — Working in Alaska and discovering space for creativity 14:00 — Taking on the Appalachian Trail as a relatively new backpacker 15:00 — Trail community, rainy days, and learning to embrace uncomfortable conditions 18:00 — Solo female hiking, trusting your instincts, and uncomfortable encounters 24:00 — Why Monica keeps choosing long-distance trails and hard things 25:30 — How “Moss” became her trail name—and why you should apparently pet the moss 29:00 — The PCT, CDT, and squeezing every last drop out of an adventure 33:00 — Snow travel, fear, and knowing the difference between growth and too much risk 39:00 — How Monica financially makes months-long adventures possible 42:00 — Saving for “future Moss” while still living for “now Moss” 44:00 — Turning nature and travel into Chasing Trails Art 50:00 — Why making art can sometimes feel harder than hiking thousands of miles 58:00 — Dreaming about a traveling mural tour and combining work with adventure 59:00 — Living your great life right now About Monica Aguilar Monica Aguilar is a Massachusetts-based artist, thru-hiker, and adventurer whose travels inspire much of her creative work. She has thru-hiked the Appalachian Trail and Pacific Crest Trail and completed more than 3,000 miles on the Continental Divide Trail. Through Chasing Trails Art, Monica creates murals, seasonal window paintings, and nature-inspired artwork drawn from the landscapes and experiences she encounters along the way. Connect with Monica Aguilar Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms. Follow along on Instagram and Facebook for clips and behind-the-scenes content, connect on Facebook at On Adventure Podcast with Josh Self, and find Josh on LinkedIn. If this episode resonated with you, leave a review and share it with someone who might need the reminder that you can prepare for the future while still living your great life right now. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/42934187

Episode 79: Why Altitude Humbles Even Experienced Climbers with Karl Frank 09/04/2026

Episode 79: Why Altitude Humbles Even Experienced Climbers with Karl Frank What do you find out about yourself when the mountain sends you back down? In this episode of On Adventure Podcast, Josh talks with Karl Frank, a Colorado native, mountaineer, and President of A&I Wealth Management in Denver. Karl grew up hiking out the back door of his family's home at 7,000 feet, and he is now working his way through the Seven Summits. They discuss two very different trips up Kilimanjaro, a December summit of Aconcagua that most of the group did not finish, and a winter ascent of Mount Whitney where a single misstep by a teammate would have taken everyone off the wall. Underneath the stories is a running theme: the mistakes Karl remembers most are the ones that came from being sure of himself. In This Episode Growing up in the Colorado foothills and hiking alone as a kid Why he keeps looking for a personal limit he has not found yet Turning back at 16,000 feet on Kilimanjaro, and the trail that opened up because of it Altitude, arrogance, and the medical help he did not ask for Summiting Aconcagua in a bad weather year Frostbite, impaired judgment, and gear left in the pack Training on stairs and the Manitou Incline The Seven Summits plan, and why Denali is the hard one Faith, quiet, and the spiritual pull of high places Being genuinely afraid of heights and climbing anyway Episode Chapters 00:00 – The question behind every conversation Josh explains what he is really after: not the summit list, but the reward that keeps people going back. 01:00 – Growing up in the Colorado foothills Karl describes a childhood spent hiking alone at 7,000 feet, thirty years of marriage, and how easily you can lose yourself inside what you build. 02:30 – Two very different trips up Kilimanjaro A chest cold on a dry, dusty Lemosho Route turns into a turnaround at Barranco Wall, and a rare descent down the Umbwe Route. 05:00 – A Land Cruiser ambulance and a one room clinic The evacuation, the doctor who was unimpressed with his symptoms, and an antibiotic that is not sold for humans in the United States. 07:30 – When the detour becomes the trip Josh draws the parallel to planning. The contingency you never wrote down is sometimes the part you remember. 10:30 – Aconcagua in December Mendoza, a guide who has done the mountain sixty times, camps at 14,000 through 19,600 feet, and a summit on day twelve of a nineteen day window. 14:45 – A leveled camp and how you respond A climber walks into camp smiling after a night of 100 mile per hour winds, a collapsed tent, and altitude sickness. Karl's takeaway is about not judging what you can see. 16:00 – Turning around, frostbite, and judgment at altitude How Karl decides to push on or stop, the heavy gloves he carried and did not wear, and why you spot impairment in your partners long before yourself. 21:00 – Stairs, the Manitou Incline, and the Seven Summits His training approach, plus what is next: Carstensz Pyramid, then Denali, and why Denali is considered the hardest of the seven. 30:30 – Why he keeps going back Karl says he feels most alive when he is a little bit in danger, and explains the spiritual weight the mountains carry for him. 31:45 – The most dangerous moment: Mount Whitney in winter A traverse across concrete snow, a fifty meter runout, and a stretch where the outcome was entirely out of his hands. 38:30 – Calm, faith, and a droplet of water What he has learned about himself, and a Buddhist image about how briefly any of us are here. 43:45 – Facing a little fear, often Karl is afraid of heights. He explains how repeated small exposure lets him stay steady when the stakes are real. 46:30 – Skiing kids, football, and building A&I Raising three mogul skiers, a college football injury that changed his direction, three master's degrees, and how A&I Wealth Management got its name. Memorable Quotes "What's my personal limit? I haven't found it yet, so I keep pushing to find it." "You miss out on who you are if you just think about what you build." "It's how you respond to what the world lays out on you." "I feel most alive when I'm a little bit in danger." "We're here for just a little bit." Key Takeaways Turning around is not the same as failing. The Kilimanjaro attempt Karl did not finish sent him down a trail few climbers are permitted to use, and he counts it among the best hikes of his life. Arrogance is the real altitude risk. Two physicians in his group were carrying a full medical kit. He never asked, because he was the guy from the big mountains. Carrying the right gear is only half of it. He had his heaviest gloves in his pack on Aconcagua and skipped them to move fast. He lost the skin on the tips of all ten fingers and toes. Getting up is optional. Getting down is not. The summit is the halfway point, and most of the trouble starts after it. Face a little fear on purpose. Small, repeated exposure is what builds the calm you need when a situation turns serious. Nobody goes couch to Aconcagua. Capability gets layered in over years, and that is true well outside the mountains. Resources Mentioned A&I Wealth Management, The Money Trail Guide, our free resource on planning for any adventure, minimizing trail waste along the way, and moving toward what matters most. Grab your copy at About Karl Frank Karl Frank, CFP®, MSF, MBA, MA, is the President of A&I Wealth Management, a second generation Colorado firm founded in 1986. He holds a Master of Arts in English from CU Boulder and a Master of Science in Finance and an MBA from the University of Denver. A Colorado native, former college football player, and lifelong skier, Karl has climbed many of Colorado's fourteeners along with Kilimanjaro and Aconcagua. He and his wife Stacy have three grown children. Keep Exploring Subscribe to On Adventure in your podcast app and on YouTube for more conversations with everyday explorers finding the edge of possible. Share this episode with someone who needs permission to turn around. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/42614805

Episode 78: Adventure Has No Expiration Date with Beverly MacDowell 08/28/2026

Episode 78: Adventure Has No Expiration Date with Beverly MacDowell Adventure Has No Expiration Date with Beverly McDowell What if some of your greatest adventures are still ahead of you? In this episode of On Adventure, Josh sits down with Beverly MacDowell, a retired educator, hiking guide, trail maintainer, and lifelong learner based in Asheville, North Carolina. She’s also the sister of actress Andie MacDowell - but Beverly has carved out an adventurous story entirely her own, much of it after age 50. Beverly shares how hiking became a source of joy, confidence, community, and purpose, from introducing women over 60 to backpacking to maintaining sections of the Appalachian Trail. Along the way, she and Josh explore the beauty of Western North Carolina, the recovery following Hurricane Helene, the remarkable restoration of Max Patch, and why continuing to challenge ourselves physically and mentally becomes even more important as we age. At the heart of the conversation is a simple reminder: you don't have to take on crazy risks to become an adventurer. And you certainly don't have to stop because you're getting older. 🥾 In This Episode 00:00 — Beverly's unexpected second career as a hiking guide 03:00 — Guiding visitors through Asheville and the Blue Ridge Mountains 05:00 — George Vanderbilt's lasting impact on Western North Carolina 09:00 — Helping women over 60 experience backpacking 13:00 — What first-time backpackers discover about themselves 14:00 — Favorite destinations: the Smokies, Mount Mitchell, and 6,000-foot peaks 17:00 — Hiking and tourism in Asheville after Hurricane Helene 19:00 — How Max Patch recovered from being “over-loved” 24:00 — Beverly's favorite places to take first-time visitors 30:00 — Why the mountains keep calling her back 33:00 — Discovering camping at 36—and raising outdoor kids 34:00 — Why it's never too late to start hiking 36:00 — Movement, balance, aging, and becoming more “antifragile” 39:00 — Finding your own challenge and growth zone 41:00 — Nature as meditation and an antidote to distraction 44:00 — What outdoor experiences teach the next generation 49:00 — Beverly's search-and-rescue training and continuing desire to learn 53:00 — The enduring lesson: adventure can begin at any age 54:00 — How to connect with Beverly and hike with her 🌲 Key Takeaways It's not too late. Beverly didn't begin camping until her 30s, joined the Carolina Mountain Club in her 50s, began maintaining the Appalachian Trail at 59, and started search-and-rescue training at 65. A little challenge is good for us. Hiking asks the body and brain to constantly adapt—from navigating rocks and roots to maintaining balance—and Beverly believes those challenges become especially valuable as we age. Guidance can turn intimidation into independence. By providing equipment, knowledge, safety, and community, Beverly has helped women over 60 discover that backpacking isn't beyond their reach. Nature restores more than the body. For Beverly, being outside is simultaneously exercise, meditation, education, and connection. As she puts it, getting outdoors is simply “a balm.” Protecting wild places matters. From her trail-maintenance work at Max Patch to her love for Pisgah National Forest, Beverly's story is also a reminder that the places that give us so much need something from us in return. 💬 Memorable Moments “The majority of everything I did was post-50.” “It's a balm to get outside, to get your feet on the earth and walk.” “A little challenge is good.” “It makes you a completely badass grandmama.” Connect with Beverly Follow for Western North Carolina hiking, wildflowers, mushrooms, and outdoor adventures. You can also find Beverly and request a guided half-day, full-day, or backpacking experience through Whether your next adventure is a multi-day backpacking trip or simply walking a trail you've never explored before, Beverly's message is worth carrying with you: Start where you are. Keep moving. And don't assume your best adventures are behind you. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/42593145

Episode 77: The John Muir Trail, Leadership, and Running Toward Adventure with Alex Potts 08/07/2026

Episode 77: The John Muir Trail, Leadership, and Running Toward Adventure with Alex Potts What happens when you stop running away from the pressures of life and start running toward the life you actually want? Alex Potts grew up in Sunnyvale, California, riding BMX bikes through the apricot orchards that would eventually become the heart of Silicon Valley. Raised by a single mom who taught elementary school and worked hard to keep their family afloat, Alex learned early lessons about money, service, resilience, and taking care of other people. Those lessons followed him into a remarkable career. Alex spent more than three decades helping build what became Loring Ward, a firm that helped pioneer the fee-based model used by independent financial advisors today. Along the way, he discovered that the most meaningful work wasn't simply about accumulating assets. It was about helping people solve problems that actually mattered. Then, while still in his 50s, Alex stepped away from the top job. And that's where another chapter of his story really began. In this episode of On Adventure, Alex and I talk about business, family, friendship, endurance, and the pull of wild places. We explore why running became an outlet during one of the most stressful periods of his life, how the John Muir Trail helped reshape his relationship with adventure, and why some of his strongest friendships have been forged while doing difficult things outdoors. We also get into a frightening day in the Grand Canyon when Alex—despite being in some of the best shape of his life—learned just how quickly an adventure can turn dangerous. A mile and a half from the top, in extreme heat, his body started shutting down. What helped turn things around? A total stranger and a bag of beef jerky. This conversation is ultimately about much more than hiking or business. It's about service, wisdom, community, and getting busy living while you still have the opportunity. In This Episode We talk about: From Silicon Valley to financial industry leadership — Alex's upbringing in Sunnyvale, the influence of his parents, and his three-decade journey helping build Loring Ward. Building a life around service — Why Alex believes great businesses, advisors, and leaders put helping people ahead of products, assets, or “wallet share.” Running away vs. running toward — How running initially became an escape from the pressures of work and family before adventure evolved into something Alex intentionally pursued. Adventure, friendship, and community — From the John Muir Trail and Mount Whitney to the Excellent Adventure group, Alex explains why difficult experiences shared with others create unusually strong friendships. Knowing your limits—and having each other's backs — What a dangerous Grand Canyon rim-to-rim hike taught Alex about preparation, humility, listening to his body, and the unexpected kindness of strangers. Episode Timestamps Episode Timestamps 00:00 – From Silicon Valley Roots to Loring Ward Alex's childhood in Sunnyvale, being raised by a single mom, and the unlikely path that led him into financial services and eventually to building Loring Ward. 08:00 – Building a Business Around Service, Not Sales Why Alex rejected the traditional asset-gathering mentality and built a culture centered on genuinely helping advisors and their clients solve meaningful problems. 18:00 – Where the Drive to Help Others Comes From Alex reflects on his mother, his father's recovery from addiction, and how both shaped his belief in service, compassion, and taking care of people. 21:00 – The Day Running Changed His Life Overwhelmed by a demanding career, young children, and little sleep, Alex started running—and discovered the value of exercise, solitude, and uninterrupted thinking. 24:00 – The John Muir Trail and Finding Sanctuary Outdoors Backpacking through Yosemite and the Sierra Nevada, encountering ancient forests, and discovering the peace and perspective that come from extended time in wild places. 31:00 – Running Away vs. Running Toward Adventure How Alex's relationship with the outdoors evolved from a coping mechanism and escape into an intentional pursuit of adventure, challenge, and joy. 33:00 – Why the Best Adventures Are Shared From Mount Whitney to the Excellent Adventure group, Alex and Josh explore friendship, companionship, and why doing hard things together creates such powerful bonds. 41:00 – Knowing When to Push—and When to Stop Why fitness isn't enough in the backcountry, how experience builds wisdom, and the importance of checking your ego when conditions or your body tell you something isn't right. 43:00 – Grand Canyon Survival, Beef Jerky & Trail Magic A rim-to-rim Grand Canyon hike in 110-degree heat goes sideways, a stranger's bag of beef jerky helps Alex recover, and the experience becomes a powerful lesson in humility and having each other's backs. A Few Takeaways Adventure can change from escape to pursuit. At one point, running and the outdoors gave Alex a way to cope with stress. Eventually, something shifted. Instead of running away from something, he began running toward experiences he genuinely wanted. Fitness and wisdom aren't the same thing. Being capable of pushing harder doesn't always mean you should. Experience teaches us to recognize the signals our bodies—and sometimes our lives—are sending. The best adventures are often about the people beside you. The summit matters. The trail matters. But years later, it's often the people who struggled, laughed, helped, and celebrated alongside us that we remember most. Service is a way of being. Whether you're helping a client navigate a family crisis, staying at the back of a hiking group to make sure everyone gets home, or opening a door for someone at the grocery store, the principle is the same: I've got your back. Resources & References Mentioned John Muir Trail — The roughly 200+ mile Sierra Nevada trail Alex has backpacked in sections Yosemite National Park — One of Alex's favorite places on the planet Pacific Crest Trail (PCT) — Alex discusses encountering thru-hikers while on the JMT Henry Cowell Redwoods State Park — Near Alex's home in the Santa Cruz Mountains and home to magnificent old-growth redwoods Undaunted Courage by Stephen E. Ambrose — Alex's recommended account of the Lewis and Clark expedition Arthur Brooks — Referenced during the discussion of “deal friends” versus “real friends” Dimensional Fund Advisors — An important part of Alex's professional story and later his son's career Final Thought One of the most memorable ideas in this conversation is also one of the simplest. When you're on a trail and someone is struggling, you help. You don't ask whether they're part of your group. You don't calculate what's in it for you. You recognize that today it's them—and tomorrow it could be you. Alex has carried that philosophy from his childhood into business, from business onto the trail, and from the trail back into everyday life. Maybe that's part of what adventure is here to teach us. Take care of the people around you. Know when to push and when to turn around. Find places where the voices go quiet. And don't spend your whole life running away from something. Find something worth running toward. Keep the Adventure Going If this conversation resonated with you, share it with someone you'd want beside you on the trail. Subscribe to On Adventure wherever you listen to podcasts, and check out The Money Trail Guide for practical ideas to help you plan for adventure, minimize “trail waste” along the way, and use your resources to move toward the life that matters most to you. Because someday isn't the goal. The adventure is happening now. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/42358570

Episode 76: Summit Fever and Close Calls - Knowing When to Turn Back in the Mountains with Stefan Gruber 07/24/2026

Episode 76: Summit Fever and Close Calls - Knowing When to Turn Back in the Mountains with Stefan Gruber What happens when you build your work around the life you want to live? In this episode of On Adventure, Josh talks with Stefan Gruber, a climber, photographer, traveler, and customer success professional at Levitate. Stefan shares how remote work and his wife Sarah’s career as a travel nurse have helped them create a life centered on movement, creativity, and outdoor adventure. They discuss climbing, film photography, international travel, dangerous moments in the mountains, and the judgment required to turn around when conditions are not right. At the heart of the conversation is a simple message: meaningful experiences should not always be postponed. In This Episode Building a mobile life around remote work and travel nursing Why climbing creates focus, presence, and flow Traveling through the American West, Poland, and Nepal The appeal of film photography and printed images Balancing documentation with being present Avalanche terrain, exposed climbing, and failed summit attempts Summit fever, risk assessment, and the limits of luck Future goals, including the Grand Teton and Colorado fourteeners Why Stefan believes in doing things while you still can Episode Chapters 00:00 – Colorado Springs and life on the move Josh and Stefan discuss Colorado Springs, choosing temporary homes, and the possibility of eventually buying land in Colorado or Montana. 11:00 – Stefan’s career and lifestyle Stefan explains how he moved from a long corporate commute into remote work and began traveling with Sarah during her nursing assignments. 17:30 – Climbing, travel, and flow Stefan reflects on his Polish heritage, his early interest in travel, and the sense of complete focus he finds while climbing. 20:00 – Designing work around life The conversation explores the freedom and tradeoffs of building a career that supports travel, adventure, and flexibility. 24:00 – Poland and international travel Stefan describes Poland’s cities, mountains, coastline, affordability, and cultural growth, along with other memorable travel experiences. 36:30 – Photography and creative ambitions Stefan explains how photography connects his travels and outdoor life. He also shares ideas for creating a travel channel with Sarah. 41:00 – Film, digital photography, and presence They discuss the visual character of film, the value of printed photographs, and the tension between capturing an experience and fully living it. 51:00 – Risk, fear, and turning around Stefan recounts dangerous moments involving avalanche terrain, exposed climbing, wildfire smoke, and two unsuccessful attempts on the Grand Teton. 57:00 – Summit fever and the limits of luck The conversation turns to humility, decision-making, and why surviving a poor choice does not make it a good one. 1:04:00 – Survival psychology and photography advice Stefan recommends Deep Survival by Laurence Gonzales and encourages new photographers to begin with whatever camera they can access. 1:11:00 – Favorite mountains and future goals Stefan talks about the Tetons, Annapurna Base Camp, Denali, Everest, and his goals for the rest of 2026. 1:18:00 – Do it while you can Stefan closes with his belief that health, time, and opportunity are uncertain, so meaningful goals should not always be saved for later. Memorable Quotes “Sometimes those limits find you.” “There’s a certain store of luck, and it will run out eventually.” “If it doesn’t happen today, it can happen another day.” “Do it while you can.” Key Takeaways Build work around what matters. Flexible work can create more room for travel, relationships, creativity, and meaningful experiences. Turning around is not failure. Good judgment sometimes means abandoning a climb or summit and returning under better conditions. Luck is not a strategy. A successful outcome does not automatically mean the decision behind it was wise. Give photographs a life beyond the screen. Printing images or shooting film can make photography feel more intentional and lasting. Do not save everything for someday. Adventure can be a major expedition or a small personal goal. The important step is beginning while the opportunity still exists. Resources Mentioned Deep Survival: Who Lives, Who Dies, and Why by Laurence Gonzales Stefan's page About Stefan Gruber Stefan Gruber is a climber, traveler, and photographer who works remotely for Levitate. He and his wife Sarah travel throughout the United States for her nursing assignments while pursuing hiking, climbing, skiing, photography, and international travel. Keep Exploring Subscribe to On Adventure in your podcast app and on YouTube for more conversations with people building meaningful lives through exploration, challenge, and curiosity. Share this episode with someone who has been saving an important goal for “someday.” /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/42194195

Episode 75: Hard Things Are Worth Doing with Justin Smith 07/10/2026

Episode 75: Hard Things Are Worth Doing with Justin Smith Episode Description What happens in the dark hours before sunrise on day two, when your body starts asking what exactly you are doing out here? Justin Smith teaches high school in Santa Cruz, California, where his classroom is a working bike shop. By day he runs a Career Tech Ed program through Project Bike Tech, teaching teenagers to fix bikes, build resumes, and solve real problems with their own hands. On his own time, he is an ultra-endurance athlete who has finished the 2,700-mile Tour Divide from Banff, Canada to the Mexico border in 16 days straight, raced the Fiji Eco-Challenge with Team Curl, competed at the Ironman World Championships in Kona, and returned three times to a 60-hour swimrun across the Swedish archipelago. In this conversation, Justin takes Josh inside the pain cave and the mental game of multi-day racing: the dark hours before sunrise on day two, the difference between the front country and the back country, and why the body only truly comes alive on the second night. He explains how a psychology degree and Outward Bound canoe trips led to a life built around adventure, why he and his wife once lived in a tiny house they built on television, and how putting himself in hard situations makes him a better dad, husband, and teacher. They also talk about the people. From trail angels on the Pacific Crest Trail to a septic-truck driver in Southern California, Justin keeps returning to the connections that outlast the miles. Most of all, this is a story about a simple idea he repeats to his students and his daughter: a ship is safe in its harbor, but that is not what ships were built for, and the more you do hard things, the more you realize hard things are worth doing. Episode Highlights • 00:00 Meet Justin Smith: high school teacher by day, ultra-endurance adventurer on his own time • 02:00 The bike shop classroom and the Project Bike Tech program in Santa Cruz • 08:00 Building a tiny house on the TV show Tiny House Nation • 14:00 The permission slip to not conform, and choosing the hard path on purpose • 16:00 Comfort is what gets sold to us, but hard things are what move the needle • 19:00 Meeting Roy Malone at the 2019 Fiji Eco-Challenge with Team Curl • 20:00 The One Water swimrun across the Swedish archipelago, attempted three times • 26:00 The Stagecoach 400 and sleeping on McDonald’s cardboard with no sleeping bag • 31:00 Courtney Dauwalter’s pain cave, and learning to redecorate it instead of fighting it • 38:00 Finishing the 2,700-mile Tour Divide in 16 days, from Banff to the Mexico border • 43:00 The Pacific Crest Trail, meeting his wife, and hiking through grief in 2009 • 55:00 Orienteering, gut instinct, and trusting intuition when the map runs out • 01:04:00 A ship is safe in its harbor, but that is not what ships are built for • 01:12:00 The mantra: if you can’t get out of it, get into it, and find a way About Justin Smith Justin Smith is a high school Career Tech Ed teacher in Santa Cruz, California, where he leads a bike shop program through Project Bike Tech, and a lifelong endurance athlete and adventurer. A former NCAA swimmer, he has finished the Tour Divide, raced the Fiji Eco-Challenge and multiple expedition-style adventure races, competed at the Ironman World Championships in Kona, and thru-hiked the Pacific Crest Trail. He lives in Santa Cruz with his wife and daughter, with whom he shares most of his adventures. Connect with Justin Smith • Facebook: www.facebook.com/smilingjustin • Inspire Out: Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. • Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms • Follow on Instagram for short-form clips and behind-the-scenes content • Connect on Facebook: On Adventure Podcast with Josh Self • Connect on LinkedIn: Josh Self • If this episode resonated with you, leave a review and share it with someone who needs to hear it. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/42024480

Episode 74: Carrying a Language Home with Gil Jackson 06/26/2026

Episode 74: Carrying a Language Home with Gil Jackson Episode 74: Carrying a Language Home with Gil Jackson Episode Description What does it mean to be so connected to a place that even your name carries it? Gil Jackson, known by the Cherokee name Dohi, meaning outside or outdoors, was born in Robbinsville, North Carolina in 1951 and today lives on 30 acres just 200 yards from the spot where he came into the world. He is a fluent Cherokee speaker, one of roughly 130 left, an elder of the Snowbird community, and an educator who has taught at Stanford, UNC Asheville, and Duke. In 2014, he thru-hiked all 2,200 miles of the Appalachian Trail, walking in part to honor his ancestors on the Trail of Tears. In this conversation, Gil takes Josh inside a tight-knit upbringing built on Gadugi, the Cherokee construct of community, where neighbors came together to cut wood, harvest crops, and care for anyone in need. He explains why family kept him rooted in Western North Carolina even when opportunity called him elsewhere, how a community school preserved the language while the wider world pushed assimilation, and why Cherokee is considered one of the ten hardest languages in the world. They also talk about why Gil keeps walking. From a 48-mile day in the Great Smoky Mountains to the ladder-strewn West Coast Trail on Vancouver Island, his adventures are less about conquering anything and more about seeing the creator's creation. Most of all, this is a story about a race against time: preserving a language, the knowledge of medicinal plants, and the sacred sites that risk being lost before the next generation can carry them forward. Episode Highlights • 00:00 A name that means outdoors, and a home built 200 yards from where he was born • 02:00 The Cherokee tradition of burying the umbilical cord to connect a child to the land • 05:00 Why family kept him rooted in Western North Carolina despite chances to leave • 06:00 Growing up in 1950s Snowbird: one gravel road, one light bulb per room, no TV • 08:00 Gadugi explained: the community coming together to help in times of need • 13:00 An aunt's middle-class home, new clothes, and the family that raised him • 21:00 Selling moss for 25 cents a pound to buy a guitar he still owns • 22:00 A community school that taught English while protecting the Cherokee language • 24:00 Only about 130 fluent speakers left, and losing two and a half each month • 27:00 What makes Cherokee one of the ten hardest languages in the world • 29:00 Degrees in education, administration, and planning, and leading a language immersion school • 33:00 How Cherokee end-of-life traditions have changed over a lifetime • 35:00 Finding the therapeutic in streams, trees, and birdsong • 39:00 Why he thru-hiked the Appalachian Trail in 2014 to honor the Trail of Tears • 43:00 The brutal West Coast Trail on Vancouver Island, with 100 ladders and 10 hours for six miles • 45:00 A tense night cooking near foraging bears in Virginia • 46:00 A trail family of five speaking four languages, all wanting to learn Cherokee • 53:00 Losing the knowledge of edible and medicinal plants, and the sacred sites that hold the stories • 57:00 Rapid-fire: Gvgeyu (I love you), favorite sunrises, beloved teachers, and the White Mountains About Gil Jackson Gil Jackson (Dohi) is a fluent Cherokee speaker, elder of the Snowbird community in Robbinsville, North Carolina, and a lifelong educator who has taught at Stanford, UNC Asheville, and Duke and served as principal of a Cherokee language immersion school. He remains committed to preserving the Cherokee language, traditional plant knowledge, and the region's sacred sites, and is an avid long-distance hiker who thru-hiked the Appalachian Trail in 2014. Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. • Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms • Follow on Instagram for short-form clips and behind-the-scenes content • Connect on Facebook: On Adventure Podcast with Josh Self • Connect on LinkedIn: Josh Self • If this episode resonated with you, leave a review and share it with someone who needs to hear it /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/41806875

Episode 73: Running is Life with Aaron Saft 06/12/2026

Episode 73: Running is Life with Aaron Saft ON ADVENTURE PODCAST | EPISODE 73 Episode 73: Running is Life with Aaron Saft As a species, we only do things if there is truly a reward on the other side. So when the reward is pain, struggle, suffering, and danger, what exactly keeps driving us back out the door? Aaron Saft has spent his life chasing that answer. A five-time ACC champion at NC State whose teams finished third at the NCAA Cross Country Championships, he traded the track for the trail, ran his first 100-miler in 2016, and has since become one of the most experienced ultrarunners in the Southeast. Today he coaches roughly 75 athletes full-time through his Running Is Life platform and podcast, a business he deliberately renamed from "MR Running Pains" because he believes running, done right, should bring as much joy as it does suffering. His résumé reads like a bucket list for the sport: the Grand Slam of Ultrarunning, the Bigfoot 200, Hardrock, Leadville, UTMB, and the Tor des Géants in the Italian Alps, where a fall, a head injury, and a watchful medic ended his race. He has finished a 100-miler while spiking a 100-degree fever, outrun a mother grizzly and her cubs in Canada, and learned the hard way when to push and when to stop. But ask Aaron why he does it and he won't point to a trophy. He'll point to the upside-down photo of his family pinned to his quad, the one he looks down at in the darkest miles to remember who he is suffering for. In this conversation, Josh and Aaron trace the many forms the "why" can take. They dig into presence, learning to run a hundred miles one mile at a time, and the moment an empty drop bag at Leadville taught Aaron everything he needed to know about the generosity of the trail community. They talk about the one question you never ask an ultrarunner, the evolution from chasing a place to simply chasing the finish line, why legacy is something children catch rather than something we teach, and how an abundance mindset shaped the coaching practice he built from the ground up. It is a conversation for every everyday explorer about doing the hard things that make life fuller, right now, not someday. Episode Highlights • 06:00 The Terry Foxworth connection and the heart of On Adventure: the reward beneath the suffering • 15:00 Running Is Life: why words matter and reframing the sport away from pain • 19:00 From reluctant soccer goalie to cross country, and the high school coach who changed his life • 24:00 The NC State years: five ACC titles, redshirting, and racing the steeplechase • 28:00 Virginia, mentor Ben Thomas, the run shop, and the move into trail running • 33:00 First 50K to first 100: the long adventure runs that planted the seed • 37:00 What 100 and 200 miles teach you that a marathon never will: presence, mile by mile • 38:00 Finishing the Grand Slam and the Wasatch 100 with a 100-degree fever • 44:00 When to keep going and when to stop: the Tor des Géants head injury and a fevered DNF on Mount Mitchell • 52:00 Intrinsic motivation, the family photo on the quad, and the “debt” a race director taught him about • 55:00 The empty drop bag at Leadville and the generosity of the trail community • 59:00 “What do you need?” The only question you ask an ultrarunner • 01:01:00 Adventure versus performance, “level 49,” and racing for the finish line instead of the place • 01:08:00 Legacy as something caught, not taught, and raising two runners of his own • 01:13:00 From brick-and-mortar to online coaching: 75 athletes, an abundance mindset, and a teaching heart • 01:25:00 Rapid fire: the grizzly bear, the Altra Lone Peak 9+, best and worst races, and five 100-milers in one summer Resources and Mentions from This Episode Here are the people, places, and resources Aaron mentioned in this episode: • , Aaron’s coaching practice and podcast • Training for the Uphill Athlete, the team’s recent book study and a foundational training manual • Races referenced: Grindstone 100, Mountain Masochist 50, Hellgate 100K, Western States, Leadville 100, Wasatch 100, Hardrock 100, UTMB, the Bigfoot 200, the Tor des Géants, the Cocodona 250, and the Ouray 100 • Gear note: the Altra Lone Peak 9+ with the Vibram outsole Free for Listeners: The Money Trail Guide Josh’s free resource for everyday explorers is packed with practical insights on planning for any adventure, big or small, minimizing trail waste along the way (yes, that means taxes), and living with confidence toward whatever is most meaningful to you. It also includes key takeaways from recent On Adventure guests to help inspire your next steps. Grab your copy at . Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. • Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms • Follow on Instagram for short-form clips and behind-the-scenes content • Connect on Facebook: On Adventure Podcast with Josh Self • Connect on LinkedIn: Josh Self • If this episode resonated with you, leave a review and share it with someone who needs to hear it /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/41628830

Episode 72: Risk in Every Form with Greg Winchester 05/29/2026

Episode 72: Risk in Every Form with Greg Winchester ON ADVENTURE PODCAST | EPISODE 72 Episode 72: Risk in Every Form with Greg Winchester Episode Description What does it take to keep saying yes to risk, in the boardroom, on the trail, and across all seven continents, for forty years and counting? Greg Winchester calls himself an armchair explorer, but the title sells him short. Over a 40-plus-year career in commercial real estate, he has worked through the savings and loan crisis, the 2008 financial crisis, and COVID, first as a banker, then as a co-owner, and today as an investor through his family office, Summit Investors. In 2003, he and two partners bought their company from its founders in a management buyout, personally guaranteeing the entire debt with 300 employees and no safety net. As Greg puts it, it was like walking to the end of the diving board and jumping, hoping there was water below. A lifelong Boy Scout who fell in love with the outdoors in the Roan Highlands of North Carolina, Greg went on to serve on the board of the Appalachian Trail Conservancy and to build a life of generosity that reaches all seven continents, inspired by the book Seven Summits. From an orphanage in Bolivia to a pastors' training center in Uganda, a nearly thousand-year-old cathedral in Winchester, England, and Sir Ernest Shackleton's grave on South Georgia Island near Antarctica, he and his wife set out to support smaller, lesser-known nonprofits and build real relationships, not just write checks. In this conversation, Josh and Greg trace the many forms risk can take. They dig into why leverage is a two-edged sword, how diversification and dry powder let you run into the fire when others are running out, why your gut becomes a kind of superpower after twenty years in any arena, and how setting goals every year since his twenties shaped a life of purpose. Greg also shares the two questions a pair of mentors asked him in his mid-fifties, what is a noble cause you can get involved with, and what do you actually want to do, and why finishing well may be the greatest adventure of all. Episode Highlights 00:00 An armchair explorer who spent forty years navigating real estate's biggest crises 03:00 Stumbling into commercial real estate from a bank management trainee program 06:00 The 2003 management buyout: 300 employees and everything personally guaranteed 12:00 Jumping off the high dive and hoping there is water below 14:00 A lucky break, a termination fee, and the real mix of hard work and luck 17:00 Three things that get people in trouble: cycles, capital structure, and diversification 20:00 Running into the fire in 2008 and why leverage is a two-edged sword 23:00 The gut instinct you earn after twenty years in any arena 25:00 Seven Summits and a vision to serve nonprofits on all seven continents 29:00 Winchester Cathedral, a 950-year-old Bible, and Shackleton's grave near Antarctica 38:00 What rises to the top: relationships, faith, family, and friends 40:00 A Boy Scout in the Roan Highlands and a lifelong love of the trail 46:00 Moving toward something, not away, and setting goals every year since his twenties 50:00 Finishing well and the two questions that reshaped Greg's second act Causes and Organizations Greg Supports Here are the people and organizations Greg mentioned in this episode: • Summit Investors, his family office investing in real estate across the Sun Belt • Auburn University Master of Real Estate Development program, where he serves as an adjunct and industry connector • The Appalachian Trail Conservancy, where he served on the board • The South Georgia Heritage Trust, stewards of the historic church and museum on South Georgia Island • The National Christian Foundation, which helped guide his international giving Free for Listeners: The Money Trail Guide Josh's free resource for everyday explorers is packed with practical insights on planning for any adventure, big or small, minimizing trail waste along the way (yes, that means taxes), and living with confidence toward whatever is most meaningful to you. It also includes key takeaways from recent On Adventure guests to help inspire your next steps. Grab your copy at . Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. • Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms • Follow on Instagram for short-form clips and behind-the-scenes content • Connect on Facebook: On Adventure Podcast with Josh Self • Connect on LinkedIn: Josh Self • If this episode resonated with you, leave a review and share it with someone who needs to hear it /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/41445025

Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black 05/15/2026

Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black ON ADVENTURE PODCAST | EPISODE 71 Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black Episode Description What does it actually take to step on a plane alone, head somewhere most people would call risky, and come home a different woman? Amanda Black is the founder of the Solo Female Traveler Network, a community of more than half a million women that started as a small Facebook group during her expat years in Australia. Ten years and roughly thirty tours a year later, she leads women into places the average traveler tends to avoid: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan, and beyond. Bali was the first trip. Seventeen women signed up. Nine of them ended up with the company logo tattooed by the end of it. We talk about why she leans into destinations perceived as less safe, what real risk actually looks like versus the version we imagine, and why she pushes back on the idea that travel is simply safe or unsafe. Risk, she argues, is a spectrum and a muscle, and most women have a lot more capacity to build it than they have been told. We also get into the quieter side of all this. The cobblestone cafe in Sighișoara, Romania, where women who had known each other only a few days started telling the truth about how lonely life back home really feels. The Golden Eagle Festival in Mongolia, where she felt like she had walked into a movie set with no electricity. The unexpected pattern she keeps noticing across every trip, every country, every group: people are not really upset about the hotel room. They want to belong. Amanda also shares why she launched Kindred Community, a smaller, slower offering built around connection retreats in Southern California, and what almost a decade of leading women into the wild has taught her about courage, capability, and the kind of friendships that get a logo tattooed on someone's wrist. Episode Highlights 00:00 Welcoming Amanda Black, founder of the Solo Female Traveler Network 01:00 Building a community of 500,000+ women and running tours in 25 countries 03:00 Why she leans into destinations perceived as less safe: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan 05:00 How strangers become a travel family inside the first 48 hours of a trip 08:00 From a Facebook group in Australia to a first Bali trip where 9 of 17 women got the company logo tattooed 12:00 Talking honestly with women about safety, fear, and the gray areas of real risk 15:00 Risk on a spectrum: why "safe or unsafe" is the wrong question, and how to build the muscle over time 17:00 Mongolia and the Golden Eagle Festival: stepping into a place that felt like going back in time 20:00 What solo travel reveals about how strong and capable women really are 22:00 The hidden business lesson behind a decade of tours: everybody just wants to belong 24:00 A cobblestone cafe in Sighișoara, Romania, and the loneliness that surfaces when women finally feel safe to share 27:00 Kindred Community and the next chapter: building belonging closer to home Connect with Amanda Black Bonus for Listeners (Free Travel Quiz): The Solo Female Traveler Network Website: Instagram: TikTok: YouTube: Amanda's TEDx Talk Shared Firsts: Redesigning how we find belonging Amanda's Website Kindred Community Website: Instagram: Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms Follow on Instagram for short-form clips and behind-the-scenes content Connect on Facebook: On Adventure Podcast with Josh Self Connect on LinkedIn: Josh Self If this episode resonated with you, leave a review and share it with someone who needs to hear it. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/41294770

Episode 70: Saying Yes to the Right Invitations with Colin Stroud 05/01/2026

Episode 70: Saying Yes to the Right Invitations with Colin Stroud ON ADVENTURE PODCAST | EPISODE 70 Episode 70: Saying Yes to the Right Invitations with Colin Stroud Episode Description What if your next great adventure is not a destination at all, but a willingness to say yes to the breadcrumbs life keeps dropping in front of you? Colin Stroud is a 26-year-old credit card rewards consultant, founder of Go Somewhere, and one of the fastest growing voices on LinkedIn in the points and miles space. He grew up in Fort Wayne, Indiana, the son of an OB/GYN and a nurse midwife who met delivering a baby together, and he was on track for a more traditional path until a six-week Spanish immersion trip to Oviedo at 16 cracked the world wide open. From there it was Italy on a $380 flight, a Catholic mission to Poland, an unlikely run at Ave Maria University in south Florida, an early marriage and a baby on the way before he had even graduated, and a first job in life insurance case design that he knew almost immediately was not it. What followed is a story about paying attention. A coworker mentioned the Chase Trifecta. A LinkedIn post about points went viral and got picked up by The Washington Post. A side hustle turned into consulting calls, then into a community for business owners, then into a full-time business helping families and entrepreneurs unlock travel they thought they could not afford. We talk about why early travel rewires you, what it actually takes to leave a steady paycheck, the difference between dopamine and meaning, why family life and entrepreneurship feel like the truest adventures of his life right now, and the surprising decision he and his wife made after almost moving to Hawaii. Colin makes a strong case that the go somewhere life is not always about getting on a plane, and that learning to be rooted where your feet are can be its own kind of expedition. Episode Highlights 00:00 From cheap flights as a teenager to a full-time business helping people unlock travel 06:00 World Youth Day in Poland, six weeks of Spanish immersion in Oviedo, and catching the travel bug 14:00 Marriage, a baby on the way, and a first job in life insurance that did not fit 18:00 Discovering the Chase Trifecta and stepping into the points world 23:00 The first viral LinkedIn post and a Washington Post quote that changed everything 25:00 Quitting in November 2024 and going full-time on Go Somewhere 30:00 Almost moving to Hawaii, pumping the brakes, and rethinking what travel does for young kids 34:00 Why family life and entrepreneurship are the truest adventures of his life right now 39:00 Measuring yourself: finally finding feedback after years of feeling stuck 47:00 The two ingredients behind a viable internet business: clear writing and consistent humility 55:00 What adventure means now and where to find Colin online Connect with Colin Stroud LinkedIn: linkedin.com/in/colinstroud Website: gosomewhere.world Newsletter: The Go Somewhere Newsletter at gosomewhere.world Email: colin@gosomewhere.world Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. Subscribe on , , , and all major streaming platforms Follow on for short-form clips and behind-the-scenes content Connect on : On Adventure Podcast with Josh Self Connect on : Josh Self Subscribe to the for more content! If this episode resonated with you, leave a review and share it with someone who needs to hear it /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/41063340

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden 04/17/2026

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden ON ADVENTURE PODCAST | EPISODE 69 Episode 69: No One Was Waiting at the Finish Line with Madison Blagden Episode Description What would it take to walk 10,000 miles in a single calendar year? Not across a lifetime. Not spread over a decade. One year. Madison Blagden is a long-distance hiker and content creator from Massachusetts who went from a pre-med student with zero backpacking experience to one of the most prolific endurance hikers in the country. After completing the full PCT (2022), the Eastern Continental Trail from Key West to Newfoundland (2023), and the Continental Divide Trail (2024), she did all three Triple Crown trails back to back in 2025, border to border, logging over 10,000 miles in a single calendar year. She documented every step herself through daily YouTube videos, Instagram shorts, and blog posts, all edited on the road. Starting in the Florida Keys in January, she pushed through Hurricane Helene damage on the AT, Sierra snowpack, desert heat, a debilitating hip injury in the White Mountains, and a flash flood that hit her tent in the middle of the night in the desert. The miles are extraordinary. But this conversation goes deeper than the miles. We talk about what happens between the ears when the body wants to quit, the difference between healthy internal ambition and ego-driven achievement, how the most meaningful finish lines are the ones where nobody is waiting for you, what a flash flood teaches you about calm under pressure, the spiritual dimension of pushing past absolute exhaustion, and why you will never be 100 percent ready, and that is not a reason to wait. Episode Highlights • 00:00 Introduction: Walking 10,000 miles in one calendar year • 02:00 Madison's background: pre-med to PCT with no backpacking experience • 04:00 Van life, COVID, and two years of traveling in a 19-foot RV • 09:00 Comparing the AT, PCT, and CDT: terrain, culture, and difficulty • 14:00 Hurricane Helene's impact on the Appalachian Trail and trail recovery • 19:00 Planning a 10,000-mile year: budget, timing, and keeping it flexible • 24:00 How a 5,600-mile year sparked the idea to go even further • 31:00 Funding the hike through daily content creation on the road • 34:00 Healthy ambition vs. ego-driven achievement • 39:00 Internal motivation: the David Goggins voice and the gentle encouragement • 42:00 37 miles a day for nine weeks: the math behind finishing the CDT before snow • 48:00 Hip injury in the White Mountains and the lesson in letting go • 51:00 Flash flood survival and what it reveals about fight-or-flight • 57:00 Nervous system training and calm under pressure • 01:02:00 Surrendering control: giving it up to the trail and the universe • 01:05:00 Spiritual experiences that emerge only at the edge of physical exhaustion • 01:10:00 Coming off trail softer: how big accomplishments quiet the ego • 01:15:00 Closing encouragement: you will never be 100 percent ready, so go • 01:20:00 The expanding ceiling of human limits and what comes next for Madison Connect with Madison Blagden Instagram & YouTube: Website: Substack: The Trek: Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. • Subscribe on , , , and all major streaming platforms • Follow on for short-form clips and behind-the-scenes content • Connect on Facebook: • Connect on LinkedIn: • If this episode resonated with you, leave a review and share it with someone who needs to hear it /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/40887410

Episode 68: Who You Become When There's No Way Out with Robbie Lenfestey 04/03/2026

Episode 68: Who You Become When There's No Way Out with Robbie Lenfestey Season 4 kicks off with a return visit from Robbie Lenfestey, who you may remember from episode 21. Robbie lives on Mandala Springs, a 67-acre retreat center in the mountains outside Asheville, North Carolina, and he was right in the middle of Hurricane Helene. What followed was months of disaster relief, community leadership, and eventually a very long-overdue exhale. In this conversation we get into what it actually looks like to be the calm person in a room full of panic, how a lifetime of pushing physical and mental limits builds a nervous system that can handle almost anything, and what Robbie means when he talks about the real frontier of human experience. We also talk breathwork, Internal Family Systems, flow state, a cryptid spotted multiple times on his property, and a Costa Rica trip that simply could not have been planned. This one goes deep. Episode Timeline [2:43] Hurricane Helene hits Mandala Springs and what the property looked like after [5:00] The Cherokee sweat lodge log jam that accidentally redirected the flood and saved the structures [10:03] On a tractor all night while landslides crashed down the mountain [13:41] Taking charge the morning after and what it means to be the regulated nervous system in the room [24:09] What flow state actually is and how a lifetime of edge experiences builds access to it [27:29] Internal Family Systems - separating from an emotion long enough to actually work through it [35:56] Breathwork, the Wim Hof Method, and the ancient Tibetan roots behind it [41:22] Six months of nonstop disaster relief and the bonfire moment when the grief finally released [47:17] What higher power means to Robbie and why embodied spirituality matters more than head knowledge [54:55] The Wampus cat at Mandala Springs, seen by multiple witnesses Links and Resources - Robbie's YouTube channel with breathwork videos and Wim Hof Method content - mandalaSprings.com - mandalanaturals.com - one-on-one lifestyle mentorship - Robbie's music page - Robbie's first appearance on the show - Robbie's personal Instagram page - Robbie's personal Facebook page If you enjoyed this episode, I'd really appreciate it if you'd rate, review, follow, and share the podcast. And don't forget to subscribe to our social channels, including our YouTube channel and our Instagram, Facebook and LinkedIn pages. It's one of the best ways to support the show and stay connected. Until next time, stay safe and stay On Adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/40698500

Episode 67: How to find God in Solitude, Silence and Wilderness with Bishop Mark Beckman 01/23/2026

Episode 67: How to find God in Solitude, Silence and Wilderness with Bishop Mark Beckman In this final installment of our series on spirituality and adventure, I sit down with Bishop Mark Beckman, the 4th Bishop of the Diocese of Knoxville, to explore what happens when faith is formed not just in quiet rooms, but in wild places. From hiking solo through old-growth forests to walking hundreds of miles on pilgrimage, Bishop Beckman shares how discomfort, silence, and physical effort can open us to something deeper than words. We talk about the moments that push us to the edge of our capacity—storms in the backcountry, long days of walking, fear at high elevations—and how those experiences can shape trust, humility, and presence. This conversation is a reminder that adventure doesn’t only take us outward into the world, but inward toward meaning, mystery, and a deeper awareness of God. Episode Timeline [2:22] – Bishop Mark Beckman’s calling to ministry and how the outdoors shaped his faith from an early age [6:45] – Discovering God’s presence through solitude, silence, and hiking alone in the woods [10:48] – Forming a men’s backpacking group and finding unexpected community on the trail [16:05] – Walking the Camino de Santiago and learning trust one step at a time [22:40] – Pushing through fear and physical limits on a 14,000-foot peak in Colorado [30:12] – Retreat, silence, and wilderness as pathways to deeper spiritual awareness [38:05] – Suffering, endurance, and how hardship can deepen us instead of hardening us Links & Resources If you enjoyed this episode, I’d really appreciate it if you’d rate, review, follow, and share the podcast. And don’t forget to subscribe to our for full episodes and additional content — it’s one of the best ways to support the show and stay connected. Until next time, stay safe and stay on adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/39818450

Episode 66: The Adventure Within - Finding Strength, Meaning, and Hope through Adversity with Hilal Kanaan 01/09/2026

Episode 66: The Adventure Within - Finding Strength, Meaning, and Hope through Adversity with Hilal Kanaan In today’s episode, I sit down with Dr. Hilal Kanaan - neurosurgeon, son of Palestinian immigrants, and someone whose daily work places him in the quiet but profound landscapes of human suffering, endurance, and compassion. While he isn’t chasing adventure in the traditional sense, Hilal spends his days navigating a different kind of wilderness: the emotional and spiritual terrain of walking with people through their hardest moments. We explore the kind of toughness that’s forged not on trails or mountaintops, but in operating rooms, hospital corridors, and the inner worlds shaped by personal history, faith, and humility. Hilal shares what it was like growing up between cultures, how his parents’ story of resilience shaped him, and what strength has come to mean inside a profession where asking for help can be the bravest move of all. This conversation broadened my understanding of what “adventure” can truly mean - and I think it’ll do the same for you. ⏱️ Episode Timeline Highlights [00:00] Opening the conversation with Dr. Kanaan and framing a different kind of adventure. [02:00] Growing up in Kalamazoo as the son of Palestinian immigrants. [04:00] The mix of chaos, tragedy, resilience, and optimism woven into Palestinian identity. [07:00] Balancing two cultures and the intentional ways his parents raised their family in America. [11:00] The parental tension between comfort and necessary challenge. [15:00] Identifying “the ghosts in the nursery” - what we inherit, keep, and let go of. [17:00] The book Hilal created for his kids to help them understand God, compassion, and curiosity. [24:00] Faith as a language for gratitude rather than certainty. [29:00] What it feels like to accompany patients through their darkest moments - and how their faith shapes him. [35:00] The humbling lesson of asking for help when a case goes sideways. [44:00] Hilal’s message to anyone facing hardship: your feelings are valid…and this is not the rest of your life. 🔗 Links & Resources by Harold Kushner (book referenced) 🙏 Closing Thoughts If this episode resonated with you, it would mean so much if you’d rate, follow, and review the podcast — it truly helps others discover these conversations. And don’t forget: we’re building more content on including full episodes, clips, and behind-the-scenes insights. 👉 Find and subscribe to our YouTube channel to stay connected. Until next time — stay safe, and stay On Adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/39668845

Episode 65: Why Suffering Becomes a Spiritual Awakening with Scott Sauls 12/31/2025

Episode 65: Why Suffering Becomes a Spiritual Awakening with Scott Sauls David Brooks describes life as a journey up two mountains. The first mountain is about achievement—building a career, proving yourself, chasing success. The second mountain begins when the first no longer satisfies, and you’re called into a deeper life of meaning, surrender, and service. This episode lives squarely on that second mountain. This conversation is the second installment in our series exploring where spirituality and adventure overlap, and it’s an honest look at what happens when ambition gives way to awakening. I sat down with Scott Sauls to talk about burnout, identity, and the courage it takes to walk away from what once defined you. We explore why suffering often becomes the doorway to spiritual depth, how achievement can quietly turn into addiction, and why community—not independence—is the missing ingredient in most meaningful adventures. If you’ve ever felt successful on paper but empty underneath—or sensed a pull toward something more without knowing how to answer it—this conversation will meet you right where you are. Timeline Highlights [2:45] – Why this conversation fits into the spirituality-and-adventure series [7:30] – Scott’s leadership journey and the hidden cost of achievement [14:10] – When productivity becomes identity—and why it eventually breaks us [22:40] – Why suffering often precedes clarity, healing, and spiritual growth [31:55] – Redefining adventure beyond the outdoors [41:20] – The role of community in recovery and transformation [52:10] – Curiosity, humility, and letting go of control Key Themes & Topics Midlife transition Spirituality and adventure Burnout, recovery, and identity Faith, suffering, and meaning Leadership and emotional health Community vs isolation Risk, uncertainty, and growth Links & Resources – leadership coaching and writing by David Brooks by Arthur Brooks Closing If this episode resonated with you, please follow the podcast, leave a rating or review, and share it with someone who might need this conversation. These stories grow through community—and I’m grateful you’re part of it. Thanks for listening. I’ll see you on the adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/39569735

Episode 64: Adventure, Spirituality, and the Search for Something Bigger with Reed Dunn 12/15/2025

Episode 64: Adventure, Spirituality, and the Search for Something Bigger with Reed Dunn In today’s episode—the first in a brand-new series exploring the deeper meaning behind our outdoor experiences—I sit down with my longtime friend, pastor, everyday explorer, and deep thinker, Reed Dunn, for one of the most meaningful conversations I’ve had on this podcast. This first installment leans less on adrenaline and more on the why—why we’re drawn to the outdoors, why hardship shapes us, and why so many of us pursue experiences that push us into awe, wonder, and transcendence. Reed and I dig into the spiritual side of adventure—what it means to connect with something beyond ourselves, whether you call that God or a higher power. We unpack the way wilderness confronts our limits, how beauty can shake us awake, and why disciplines of “no” might be more important today than ever. And of course, we talk about Reed’s years of backpacking, his favorite place in the world, and the moments that have stayed with him long after the trip ended. ⏱️ Timeline Summary Here are the top moments from the episode: [00:16:00] – Kicking off the conversation: why I wanted Reed on the show and how his story fits into “the meaning side” of adventure. [00:26:00] – Reed’s early backpacking years—Colorado, Arkansas, the Buffalo River Trail, and how those experiences shaped him. [00:35:00] – The memory of his favorite place on earth: a glacial lake, seven waterfalls, and the power of remembering without a camera. [00:36:00] – A deep dive into spirituality: what it means to connect with transcendence, how nature becomes a pathway, and why anyone—regardless of belief—can access it. [00:46:00] – Religion vs. spirituality: Reed breaks down the difference between learning about God and meeting God—and why both matter. [01:13:00] – Exploring hardship, asceticism, and the spiritual importance of limitation. Why “telling yourself no” opens doors to meaning. [01:22:00] – The connection between ancient spiritual practices, desert monks, and modern adventurers who push themselves to the edge in search of something more. 🔗 Links & Resources Reed’s book, — available wherever you buy books Reed Dunn on social media: Locations discussed: Colorado trail systems, Buffalo River Trail (AR), Wind River Range (WY), Appalachian Trail (ME/NH section) Find us on our new where you can see the full interviews. Also give us a like and a review while you're at it! 🙌 Closing Remark If this conversation stirred something in you, inspired you, or made you think differently about why we chase adventure in the first place, I’d love for you to rate, follow, share, and review the podcast. It helps more everyday explorers find these stories—and it keeps great conversations like this one coming. Thanks for listening, and keep living your adventure on purpose. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/39416805

Episode 63: Walking Into a New Life - How a 100+ Pound Transformation Led to Ultra Endurance Success with Lisa Decker 11/28/2025

Episode 63: Walking Into a New Life - How a 100+ Pound Transformation Led to Ultra Endurance Success with Lisa Decker In this episode of the On Adventure Podcast, I sit down with ultra-endurance athlete Lisa Decker, whose story is a powerful blend of resilience, transformation, and the relentless pursuit of hard things. Lisa didn’t come from a traditional running background—yet she discovered the world of ultra running through community, curiosity, and a willingness to push herself beyond her comfort zone. What followed is a decade-long journey that includes a 120-pound weight-loss transformation, countless ultras, and the life-changing experience of completing the legendary Vol State 500K across Tennessee. We dive deep into what motivates someone to walk 314 miles in the July heat, how finding the right community can unlock new levels of confidence, and why endurance challenges often lead to profound personal growth. This episode is packed with insight about mental toughness, identity shifts, overcoming self-doubt, and discovering what you’re really capable of when you take that first step—literally. If you’re searching for inspiration, endurance storytelling, personal transformation, or insights about long-distance running and mindset, this episode delivers. ⏱️ Timeline Highlights [2:15] – Lisa’s early life in California, her outdoors-focused upbringing, and how nature shaped her love of adventure. [6:40] – Discovering the trail and ultra running community through Team RWB and why it instantly felt like “home.” [14:30] – How she balances 10-hour pharmacy shifts with ultra training, and why walking ultras became her key to success. [17:45] – The unexpected moment on the Vol State ferry that led to forming a five-person pack and transforming the entire race experience. [23:10] – Kind strangers, roadside hospitality, skunk encounters, and what surprised her most during the 500K journey run. [28:40] – Doing ultras while overweight, finishing last, and why showing up anyway built the foundation for her transformation. [36:50] – The mental battle of “head trash,” the power of community support, and why being honest about struggles matters. [49:00] – Future adventure goals, including walking the Caminos in Europe and exploring the world on foot. [58:30] – How endurance sports shifted her personal identity, career goals, and even her vision for where she wants to live next. 🔗 Links & Resources Featured Organizations & Topics – Veterans & civilians building connection through fitness – Search “Vol State 500K” on UltraSignup – Pediatric cancer support & scholarships 💬 Final Thoughts If this conversation inspired you or helped you rethink what’s possible for your own life, please rate, follow, share, and review the podcast. Every bit of support helps new listeners discover these stories—and it keeps the adventure going. And don’t forget: 👉 Subscribe on for full video episodes /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/39200690

Episode 62: From Ultras to FKT's to Ocean Crossings: You Won’t Believe What Mike Wardian’s Doing Next! 11/14/2025

Episode 62: From Ultras to FKT's to Ocean Crossings: You Won’t Believe What Mike Wardian’s Doing Next! What happens when you stop waiting for permission and start chasing wild, audacious goals? That’s exactly what we unpack in this powerhouse episode with Mike Wardian—elite endurance athlete, record-setting runner, and all-around inspiration. From running across the United States to setting a fastest known time (FKT) on the Appalachian Trail for his age group, Mike shares the mindset behind tackling the unimaginable. But this conversation goes beyond races and records. Mike opens up about what fuels his drive, how he builds resilience through repetition, and how he balances his career, family, and love for adventure. Whether you're prepping for your first 10K or dreaming of rowing solo across the Atlantic (yep, that's on his calendar too), there’s something here for everyone chasing big goals. 🔥 What You’ll Learn How Mike plans his insane endurance calendar using a Post-it Note system The real story behind his Appalachian Trail record attempt — injuries, storms, and mental toughness Why he’s trading trails for water in 2027: rowing across the Atlantic solo How to push through when motivation runs dry — the power of micro-goals Mike’s approach to family, business, and adventure life balance What he’s learned about humanity and resilience from running thousands of miles 🏆 Featured Moments [1:04] – Mike’s “goal list” strategy for setting and sticking to ambitious challenges [4:58] – What is the Taco Bell 50K and the Full Ham Triathlon? (Hint: They’re tougher than they sound) [6:55] – Why Mike’s next adventure is rowing solo across the Atlantic Ocean [9:02] – The difference between saying yes to challenges and actively seeking them out [15:45] – Why the Appalachian Trail holds a special place in Mike’s heart [23:10] – Trail injuries, vegan nutrition, and how Mike fueled himself with 10,000 calories a day [32:45] – How Mike balances a full-time career and family life while pursuing ultra-endurance feats [39:01] – The truth about running across America—traffic, kindness, loneliness, and everything in between [45:40] – Why 100 burpees a day became a key part of Mike’s training routine 🧠 Listener Takeaways Your biggest goals are within reach if you break them into daily reps You don’t need to quit your job to live an adventurous life Embrace the beginner’s mindset — it’s where the magic starts There’s no substitute for consistency and curiosity “Run toward the thing you’re afraid of — it’s probably where the growth is.” 📌 Links & Resources Follow Mike Wardian on Instagram: Learn more about Mike’s gear and sponsors: , Check out upcoming grassroots races like the Taco Bell 50K via Mike’s socials 👏 Connect with Us Be sure to subscribe to our YouTube channel for full episodes, behind-the-scenes content, and more conversations just like this. You can find us on YouTube by searching On Adventure Podcast with Josh Self — and don’t forget to hit the bell so you never miss a new drop. If this episode inspired you, please follow, rate, and review the podcast on your favorite platform. It helps us grow and reach more everyday adventurers like you. And hey—share it with a friend who’s chasing their own wild goals. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/39007390

Episode 61: Why Adventurers Quit - 3 Mental Traps and How to Beat Them with Vol State 500K Finisher MAJ (Ret.) Vincent Antunez 11/02/2025

Episode 61: Why Adventurers Quit - 3 Mental Traps and How to Beat Them with Vol State 500K Finisher MAJ (Ret.) Vincent Antunez Enduring the Impossible with Vincent Antunez This episode is a deep dive into the mind and mission of Vincent Antunez, DSc, PA-C - a retired U.S. Army Major, ultra endurance athlete, and founder of Trail Toes. From grueling military deployments to multi-day ultramarathons across the globe, Vincent shares how pain, persistence, and preparation have shaped every step of his journey. We talk about what it takes to push beyond the limits of your body - and more importantly, your mind. Vincent shares raw, powerful stories of suffering and success on the course, the lessons that endurance sports teach about humility and resilience, and the gear and mindset strategies that keep him (and his feet) moving forward. This one is packed with wisdom from the front lines - of both battlefields and ultramarathons. 🎧 Don’t forget - we’re now on YouTube! Be sure to and hit that bell so you never miss an episode. And of course, follow the show wherever you get your podcasts. ⏱️ Episode Timeline: [1:12] - How Vincent met ultrarunning legend Lisa Smith-Batchen — and helped her complete her historic Badwater Quad [3:44] - A military career across decades and continents [6:57] - How a post-midnight beer run in Germany accidentally became his first marathon [11:42] - Why he keeps showing up, even without formal training [13:58] - The 3 reasons people drop out of ultras (and how to beat them) [20:31] - Innovative tips for staying cool and blister-free on brutal courses [24:49] - Trail Toes and how Vincent created it in Afghanistan [38:11] - The psychology of endurance: crews, quitting, and the right kind of pressure [52:05] - Why Vincent keeps coming back to these events — and what they continue to teach him 🔗 Links & Resources: – a trail running camp for veterans and first responders If you enjoyed this episode, please take a moment to rate, follow, and review the podcast — and share it with a friend who’s always pushing their limits. Every download helps more everyday explorers find their way forward. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/38882355

Episode 60: Inside the Mind of Speed Records, Failure, and Firearms with Tom Kubiniec 10/17/2025

Episode 60: Inside the Mind of Speed Records, Failure, and Firearms with Tom Kubiniec How do you embrace fear and failure to build a multi million dollar business, shred heavy metal guitar solos and break land speed records in a custom built car? In this episode of the On Adventure Podcast, I sit down with Tom Kubiniec—entrepreneur, former heavy metal guitarist, and the so-called "gun storage guru." From his days tearing up the music scene to building a global business in military weapon storage, Tom's journey is one wild ride. We dive deep into what it means to stake a claim in life before you've "earned it," why failure should be embraced (and quickly), and how creativity fuels not just business, but bold living. A killer insight from Tom: "You don't know where you're going to land until you jump. As you're falling, you will find a place to land. If you're not happy with that one, jump again." We also explore his adrenaline-pumping pursuits: restoring rare cars, racing across the Utah salt flats, and finding peace in silence while bow hunting. This episode is about pushing limits, whether in the boardroom, behind a guitar, or out in the wild. If you're looking for inspiration to go all-in on your ideas or just want a reminder of how short life is, this one hits home. Episode Highlights: [1:12] - Tom's journey from unknown rock guitarist to global leader in military gun storage [6:05] - The pivotal moment of "claiming" expertise before it was proven—and why it worked [13:25] - How public speaking and guitar technique both benefit from slow, intentional practice [17:00] - Fail fast: Why Tom says failure is not the enemy but the pathway to innovation [25:55] - The birth of a game-changing locking system after a live simulation revealed a major flaw [33:02] - Creating personas in business and why it's not about being fake—it's about solving problems [39:45] - Breaking a land speed record with a 750cc custom car: the build, the danger, the payoff [44:00] - Why silence in the woods and watching a forest wake up is Tom's ultimate reset [54:10] - Final reflections on living fully, embracing fear, and making the most of the one life we get Links & Resources: (Layla in DADGAD) Closing Remarks: If this conversation with Tom fired you up to take bold steps in your own adventure, make sure to follow the podcast so you never miss an episode. And if you enjoyed this one, rate, review, and share it with a friend who's ready to make their move. Also, don’t forget to check out the full video episode and more on our and hit that Subscribe button. Thanks for tuning in! /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/38612220

Episode 59: What Does it Take to Be Great with Lisa Smith-Batchen 10/03/2025

Episode 59: What Does it Take to Be Great with Lisa Smith-Batchen What does greatness look like? Is it talent, time, or something deeper? In this episode, I sit down with endurance legend and master coach Lisa Smith-Batchen to explore what greatness really means - and how it evolves as we do. With over four decades of coaching and ultra-running behind her, Lisa shares a wisdom-packed perspective on pushing limits, aging with intention, and chasing big dreams, no matter where you're starting. Lisa is the first American to win the grueling Marathon des Sables and the first woman to have completed the Badwater Quad - covering 584 miles across Death Valley! She’s run across multiple states for charity, completed a 50-mile ultra in every state, and raised over $1 million for orphanages and clean water projects. But what’s just as remarkable is how grounded, present, and purpose-driven she remains through it all. We dig into the transformative power of endurance sports—not just physically, but mentally and spiritually. Lisa opens up about what keeps her coming back to extreme challenges, the emotional shifts that come with aging as an athlete, and how learning to put yourself first might just be the most radical move of all. Whether you're training for your first 5K or simply trying to show up fully in life, this one’s for you. 🕓 Timeline Highlights [3:55] – Lisa's 20-year coaching journey with Bob Becker and the bond beyond the miles [6:45] – Getting cut from the team—and how it shaped her coaching philosophy [9:25] – Breaking records and barriers: Badwater Quad, 50 ultras in 50 states, and running for causes [12:15] – The path from average to good to great: Lisa’s simple but powerful growth model [17:49] – Embracing evolution: letting go of who you were to step into who you're becoming [29:01] – A moment at mile 132 that changed Bob Becker’s mindset—and maybe yours too [34:00] – Why making time for yourself isn’t selfish—it’s essential [41:15] – What keeps Lisa coming back to the edge of endurance: joy, clarity, and spiritual connection [57:22] – Guiding a blind and deaf athlete through 140 miles—Lisa’s next adventure 🔗 Links & Resources – Lisa’s personalized coaching platform – The 140-mile race Lisa will be guiding in November – The world's toughest foot race 💬 Final Words This episode offers far more than endurance talk—it's a blueprint for living with purpose, courage, and connection. If it struck a chord with you, be sure to subscribe and leave a review wherever you listen. And don’t forget - head to our to subscribe and watch the full conversation. We’ve got more powerful stories coming your way, so stay tuned and stay on adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/38441010

Episode 58: How to run through Death Valley in July at age 80 with Bob Becker 09/19/2025

Episode 58: How to run through Death Valley in July at age 80 with Bob Becker In this captivating episode of On Adventure, I sit down with the legendary Bob Becker - ultramarathoner, race director, and age-defying adventurer - to unpack his incredible journey from late-blooming runner to becoming the oldest finisher of the Badwater 135, one of the world’s toughest ultramarathons. At 80 years old, Bob proves that it's never too late to rewrite your story, conquer deserts, and inspire generations. Whether you're an aspiring endurance athlete, race organizer, or simply someone looking for motivation to stay active, this episode delivers. 🕓 Timestamps & Topics Covered [00:04:00] Introduction – Welcoming Bob Becker and setting the stage. [00:06:00] Late Bloomer in Running – Bob started serious running at 57! [00:07:30] First Ultra: Marathon des Sables – 150-mile Sahara race to celebrate turning 60. [00:09:00] Why Ultras? – The deep camaraderie and the life-changing community. [00:13:00] Training Without Mountains – How Bob trains for elevation in flat Florida. [00:18:30] From Running to Race Directing – Launching the iconic Keys 100 and Daytona 100 races. [00:23:00] Life After Real Estate – How Bob turned adversity during the financial crisis into purpose. [00:27:00] Jungle Racing in the Everglades – Creating and running a now-legendary trail race. [00:34:00] Enduring Support – His wife’s unique but wholehearted support. [00:38:00] Intergenerational Adventure – Racing with his granddaughter. [00:39:30] Movement as Medicine – Encouraging older adults to “just start moving.” [00:40:00] Nutrition & Heat Strategy – Vegan lifestyle and fueling for the long haul. [00:47:00] Inside Badwater 135 – The heat, the altitude, the brutal beauty. [00:54:00] History in the Making – Becoming the oldest finisher in Badwater history. [01:00:00] Mental Grit – Mantras, bear crawls, and mindset hacks. [01:05:00] Lessons from the Trail – What Bob's learned from every finish line. 🏆 Key Takeaways 🧠 Age is not a limitation – Bob didn’t start running seriously until his late 50s. 🌱 Vegan athlete – Nutrition was key to training, racing, and recovery. 🥵 Badwater veteran – 6x Badwater runner; oldest finisher at age 80. 🛠️ Creative training methods – Pulling tires across bridges to simulate hills. 💪 Mental strength over miles – Bear crawled the last mile of Badwater in 2022. 🧡 Inspiring generations – Encourages others, especially seniors, to stay active. ✨ Notable Quotes “If someone else can do it, why can’t I?” – Bob Becker “The finish line is glorious. It’s a bragging right you carry forever.” “You’re never too old to start moving. Start walking, gardening - just move.” 🔗 Connect with Bob Becker 🎧 Enjoyed this episode? Don’t miss out on more inspiring conversations with adventurers, endurance athletes, and game-changers just like Bob Becker. 👉 Subscribe to the On Adventure Podcast on your favorite platform to stay updated with every new episode. 📺 Want to see the stories come to life? Head over to our for full interviews, behind-the-scenes clips, and bonus content you won’t hear on the audio feed. 🔥 Hit that subscribe button, leave us a review, and join our growing community of adventurers! /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/38271945

Episode 57: Barefoot Running, the Badwater Double FKT, and Chasing the Grid with Ken Posner 09/05/2025

Episode 57: Barefoot Running, the Badwater Double FKT, and Chasing the Grid with Ken Posner In this episode of the On Adventure Podcast, I sit down with Ken Posner—ultrarunner, author, former Army Ranger, and corporate financial analyst—to explore the transformative power of pushing physical and mental boundaries. Ken shares stories from his extraordinary journey completing the "grid": summiting all 35 high peaks of New York's Catskills in every month of the year. Along the way, he stripped away technology, embraced barefoot running, and found a deeper connection with nature and himself. This episode isn't just about extreme endurance. It's about rediscovering who we are when the noise of the modern world fades away. We unpack how doing hard things in nature can bring clarity, strength, and a more balanced life. Whether you're curious about barefoot hiking, intrigued by minimalist living, or seeking inspiration to shake up your own routine, Ken's story will move you. Timeline Summary: [2:22] - Ken's shift from corporate life to ultra endurance running in his late 30s [4:00] - Why he started running barefoot and what kept him going [7:45] - The joy, mindfulness, and sensation of barefoot movement [10:10] - Balancing high-tech corporate work with minimalist, analog outdoor living [19:00] - The metaphor of "signal vs. noise" and how nature helps us tune in [28:30] - Pain vs. suffering: building resilience through chosen challenges [35:00] - The Badwater Double: a 292-mile journey through Death Valley and back [47:30] - How the mountains called him at age 50 and led to chasing the grid [54:00] - The spiritual and transformative lessons learned through mountain pilgrimages Links & Resources: Ken's website: Ken Posner's book: Chasing the Grid (available Sept 23 on ) by Christopher McDougall by Nassim Taleb by Edward Abbey by Julian Jaynes Closing Remark: Please check out Ken's website and support him by purchasing his new book! If this episode sparked something in you, share it with a friend who could use a little adventure in their life. Be sure to follow, rate, and leave a review of the podcast and well as our new YouTube channel—it helps us reach more everyday explorers just like you. Thanks for tuning in! /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/38093235

Episode 56: How Great Athletes Are Made with Dr. Charles Infurna 08/22/2025

Episode 56: How Great Athletes Are Made with Dr. Charles Infurna In today’s episode, I’m joined by Dr. Charles Infurna—a coach, academic, and athlete—who shares a powerful story about unlocking human potential. From the legacy of his immigrant family to his own journey through athletics and coaching, Charles brings a deep, authentic perspective on what it really takes to push past limits and perform at the highest level. We talk about the importance of belief, the trust that fuels great coach-athlete relationships, and how to balance ambition with healthy detachment. Whether you're chasing Olympic dreams, striving for personal growth, or trying to show up better for your kids, Charles’ reflections offer real wisdom for anyone walking their own adventure. Timeline Summary [1:22] - The immigrant roots that shaped Charles’ drive and work ethic [5:00] - Early lessons from watching his parents work tirelessly for the American dream [7:50] - The college years: How track and field became the anchor that kept him moving forward [10:12] - Stepping into coaching: From reluctant start to life-changing purpose [16:00] - Navigating identity, ego, and love for the sport in his first years as a coach [19:45] - Parenting and coaching: What he's learned about motivation, belief, and letting go [22:55] - The most important thing a coach can do: Be a “light giver” and guide belief [27:10] - Stories of grit, growth, and belief from standout athlete Lewis and others [35:00] - Research insights: What Olympic coaches do differently to create trust and performance [45:00] - Inside “The Throwing Circle”: Charles’ upcoming book and how it blends story with science Links & Resources Follow Dr. Charles Infurna Instagram & Twitter: LinkedIn: Dr. Infurna’s Upcoming Book: The Throwing Circle Launching Summer 2025 – Available soon on Amazon, Barnes & Noble, Target, and Costco. Josh's Financial Planning Resources Website: Newsletter: The Money Trail Guide – Sign up on the site! Enjoyed This Episode? If you found this conversation valuable, don’t forget to rate, follow, share, and review the podcast! Your support helps us keep bringing inspiring stories and hard-won insights from everyday explorers, adventurers, and achievers. 👉 Also, be sure to find and follow our brand-new YouTube channel where you can watch full episodes and more from the On Adventure Podcast. Stay safe. Stay curious. Stay on the adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/37906280

Episode 55: From Conservation to Kilimanjaro - A Life of Meaningful Struggle with Tom Hicks 08/08/2025

Episode 55: From Conservation to Kilimanjaro - A Life of Meaningful Struggle with Tom Hicks What does it really mean to suffer with purpose? In this episode of On Adventure, I sit down with conservationist and ultra-endurance athlete Tom Hicks – a man whose journey is as layered as the landscapes he climbs. From leading anti-poaching efforts across Africa and Asia with the David Shepherd Wildlife Foundation to tackling brutal challenges like Ironman races and high-altitude expeditions, Tom’s life is defined by intentional hardship, deep introspection, and relentless forward motion. We dive into the heart of resilience, why discomfort can be transformative, and how a former rugby coach found meaning in the mountains. Tom also shares his connection with previous On Adventure guest Holly Budge and his plans to lead a new team to the summit of Kilimanjaro. Whether you're an aspiring adventurer, a mindset junkie, or someone wrestling with self-doubt, this episode delivers a powerful reminder: growth is never linear, and purpose is often found in the pain. Episode Highlights: [3:00] – Fighting global wildlife crime: Tom’s work with the David Shepherd Wildlife Foundation [8:00] – The brutal truth about poaching, organized crime, and the risks of field conservation [12:00] – From being told he’d never succeed to becoming a conservation leader [18:00] – Mentoring the next generation: the importance of presence and vulnerability [24:00] – The “circuit breaker” mindset tool to quiet negative inner voices [29:00] – What drives us to endure suffering in pursuit of meaning [38:00] – A life-or-death lesson on Lenin Peak – and why good decision-making matters [45:00] – Remembering Dixie Dansercoer and how it reshaped Tom’s risk tolerance [54:00] – Emotional regulation in chaos: the power of calm leadership [59:00] – Balancing ambition, burnout, and building a team for Kilimanjaro Links & Resources: Holly Budge’s Connect with Tom: Have questions about conservation, endurance training, or joining the upcoming Kilimanjaro team? Reach out to Tom directly on or – he’s always happy to connect with fellow adventurers and curious minds. Enjoyed this episode? If Tom’s story sparked something in you, take a second to rate, follow, and review On Adventure. And be sure to follow us on Instagram, Facebook, and LinkedIn for behind-the-scenes content, updates, and inspiration from the trail. Plus – don’t miss new episode drops and bonus video content on our brand-new YouTube channel. Hit subscribe and join us for the next great adventure. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/37730045

Episode 54: Suffer in Comfort and Other Lessons from Elite Mountain Guide Brian Warren 07/25/2025

Episode 54: Suffer in Comfort and Other Lessons from Elite Mountain Guide Brian Warren In this episode of the On Adventure Podcast, I sit down with Brian Warren—an elite mountain guide whose life has been defined by risk, reinvention, and a deep connection to the mountains. From thru-hiking the Appalachian Trail just days after high school to guiding in the Tetons, Himalaya, and beyond, Brian’s journey is a masterclass in resilience, leadership, and embracing the unknown. We explore how Brian transitioned from living out of a backpack to leading high-stakes expeditions around the globe—and eventually, to navigating a whole new adventure: fatherhood and a career pivot into financial services. This conversation dives deep into themes of identity, confidence vs. competence, imposter syndrome, and the unique lessons that come from suffering in comfort. If you’ve ever wondered what it’s like to reinvent yourself while carrying forward everything hard-earned from past chapters, this episode is for you. Timeline of Highlights [2:22] – Launching into adventure: Brian’s decision to thru-hike the Appalachian Trail at 18. [10:45] – Discovering leadership on the trail and earning the nickname “Merlin.” [18:20] – Transitioning from Knowles courses to guiding in Jackson Hole and the Tetons. [27:05] – Learning to ski on “toy skis” and the path to heli-ski guiding. [37:50] – Companionship as the secret ingredient to adventure: why relationships matter in the mountains. [44:00] – “Suffer in comfort”: Brian’s mantra for staying calm in high-stakes situations. [1:04:15] – Stories from the edge: avalanches, crevasse falls, and helicopter crashes. [1:10:30] – Reinventing life beyond the mountains: from guiding to financial planning. Links & Resources Sign up for newsletter for insights on funding your own adventures. Closing If this episode inspired you, please rate, review, and share the podcast. You can also find our new YouTube page! It’s the best way to help more adventurers like you find these conversations. And don’t forget to follow so you don’t miss the next episode. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/37551240

Episode 53: How a Near-Death Experience and 2,200 Miles on Foot Led to True Purpose with Tanner Critz 07/11/2025

Episode 53: How a Near-Death Experience and 2,200 Miles on Foot Led to True Purpose with Tanner Critz What drives someone to leave behind comfort and pursue something deeply meaningful? In this episode of On Adventure, I sit down with Tanner Critz - a martial artist, Appalachian Trail thru-hiker, and founder of Unity Martial Arts in Little Rock. This conversation isn’t just about hiking 2,200 miles or building a successful dojo. It’s about identity, purpose, and the courage it takes to follow your own path - especially when it’s steep and uncertain. Tanner opens up about his pivotal adventures: hiking the AT alone with a hidden bleeding ulcer, turning a quiet martial arts passion into a thriving community, and facing a near-death COVID experience that shook his world. We explore what it means to live with intention, take risks that matter, and find a sense of home in both place and people. Arthur Brooks says that to live a happy, meaningful life, we all have to answer two questions...Why am I here, and What am I willing to die for? If you’ve ever asked yourself either of these questions - this episode is for you. 🕒 Episode Timeline [3:42] - How a year of reflection led Tanner to hike the Appalachian Trail [8:15] - Experiencing deep physical pain—and choosing not to quit [14:29] - The unexpected transition from graphic design to martial arts [20:51] - Starting Unity Martial Arts and building community through connection [31:03] - The philosophy of self-defense and teaching through empathy [39:30] - Surviving COVID: A near-death experience and its lasting impact [46:10] - Finding peace, purpose, and the value of rest [52:58] - Advice for anyone standing at the edge of a big life decision 🔗 Links & Resources Books Mentioned: by Tanner Critz by Chögyam Trungpa If this episode resonated with you, take a moment to follow, rate, and review the podcast. Also check out our new YouTube page and be sure to subcribe there. And don’t forget to share it with someone who might be standing at the edge of their own next big step. See you next time, adventurers. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/37380935

Episode 52: Skydiving Everest, High Mountain Summits and Empowering Female Rangers with Holly Budge 06/27/2025

Episode 52: Skydiving Everest, High Mountain Summits and Empowering Female Rangers with Holly Budge In this special episode of the On Adventure Podcast, I sit down with the unstoppable Holly Budge—an adventurer, conservationist, and the first woman to skydive over Mount Everest. With World Female Ranger Week in full swing, this conversation couldn’t be more timely. You can find out more about what these incredibly brave female rangers do and why they are being celebrated this week. Holly opens up about transforming fear into fuel, climbing the world’s highest peak solo, and how her bold expeditions became a platform for championing female wildlife rangers. We explore her work with and the founding of World Female Ranger Week, diving into the challenges and triumphs of the women on the front lines of conservation. Whether you’re an adventure junkie, a purpose-driven leader, or someone looking for that next spark of inspiration, this episode delivers the goods. Timeline Summary: [2:15] - How a single conversation launched Holly’s journey to skydive Everest [6:47] - What it’s like to freefall at 29,500 feet over the Himalayas [12:22] - Training your mindset for mental toughness and high-altitude endurance [17:31] - The origin story of How Many Elephants and connecting passion with purpose [21:18] - Launching World Female Ranger Week and elevating unheard voices [27:05] - Grit, resilience, and the power of women protecting the wild [35:40] - What Holly’s adventures have taught her about life and leadership Links & Resources: Holly Budge: World Female Ranger Week: How Many Elephants: Follow Holly on Instagram: 🎧 Don’t Miss a Beat! If you loved this episode, make sure to follow the show on your favorite podcast app so you never miss an adventure. And we’ve just launched our brand new YouTube channel where you can catch full episodes and exclusive behind-the-scenes content—subscribe now and join us visually! 🎙️ Follow | ❤️ Rate | 💬 Review | 📤 Share — your support means the world. /episode/index/show/2d4c93f2-3b12-4fea-9aea-ce68f89a0bec/id/37154835

On Adventure Podcast with Josh Self

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