On Adventure Podcast with Josh Self

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

Wayforward Adventures — Multi-day guided backpacking experiences in Southern Colorado.

Unstuck and Alive — 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: [email protected]

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.

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

• Chasing Trails Art

• Instagram

• Facebook

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.

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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, assetsandincome.com
• 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 ridgelinewealthadvisors.com

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.

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 Bev MacDowell on Facebook 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 Blue Ridge Hiking Company.

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.

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.

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 Instagram 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

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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: www.instagram.com/inspireout/ 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 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

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:

• Running Is Life, 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 ridgelinewealthadvisors.com.

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

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 ridgelinewealthadvisors.com.

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