On Adventure: Lessons from the Edge

Two recent conversations from the On Adventure Podcast — and what they have to say about the lives the rest of us are building.

Every so often we like to step back from the episode list and look for the thread running through it. This time the thread found us. One guest has spent decades on the world’s high mountains and keeps discovering how little that protects him. The other didn’t start camping until her thirties and didn’t pick up a trail-maintenance section until she was fifty-nine. Different altitudes, opposite directions — and the same quiet conclusion. What you’ve already done is not the thing that carries you. Staying honest about where you actually are is.

Episode 79: Why Altitude Humbles Even Experienced Climbers

Karl Frank is a Colorado native, a mountaineer working his way through the Seven Summits, and the president of A&I Wealth Management in Denver — a man who grew up hiking out the back door of his family’s home at 7,000 feet and has been climbing ever since.

What stayed with us wasn’t the summit list. It was how candid Karl is about the mistakes that came from being sure of himself. On Kilimanjaro, a chest cold turned him around at the Barranco Wall — and the descent route that opened up as a result is one he counts among the best hikes of his life. Two physicians in his group were carrying a full medical kit and he never asked them for help, because he was the guy from the big mountains. On Aconcagua, in a bad weather year, his heaviest gloves stayed in his pack so he could move faster. He lost the skin on the tips of all ten fingers and all ten toes.

His line about impaired judgment is the one we keep repeating: you spot it in your climbing partners long before you spot it in yourself. He also says something quieter — that getting up is optional and getting down is not, and that most of the trouble starts after the summit. Anyone who has watched a family reach a long-planned financial milestone and then lose the plot afterward will recognize the shape of that.

Listen to Episode 79 →

Episode 78: Adventure Has No Expiration Date with Beverly MacDowell

Beverly MacDowell is a retired educator, hiking guide, trail maintainer, and search-and-rescue trainee based in Asheville, North Carolina — and the great majority of that list, as she puts it, happened after fifty.

She didn’t begin camping until her thirties. She joined the Carolina Mountain Club in her fifties, started maintaining a section of the Appalachian Trail at fifty-nine, and began search-and-rescue training at sixty-five. Along the way she has made a practice of taking women over sixty backpacking for the first time — supplying the equipment, the knowledge, and the company, so that something that looked impossible from a distance turns out to be a matter of one foot in front of the other.

What we keep coming back to is her insistence that a little challenge is good for us, and that it matters more, not less, with age. Hiking asks the body and the brain to keep adapting — rocks, roots, balance, weather — and that adaptation is the point. She and Josh also talked about Western North Carolina after Hurricane Helene, and about Max Patch recovering from being loved too hard, which is its own lesson about the places that give us a great deal and need something back.

Listen to Episode 78 →

What We Took From Both

Put the two conversations side by side and you get a useful pair of correctives.

Karl’s is a warning against confidence that has outrun the conditions. Experience is real, but it doesn’t transfer cleanly to a new mountain, a new market, or a new decade of life — and the person least likely to notice the drift is the one experiencing it. That’s most of the argument for a plan written in advance, and for having someone in the party who is allowed to say the uncomfortable thing.

Beverly’s is a warning against the opposite error — assuming the interesting part is behind you. A financial plan is not a monument to what you’ve already accumulated. It’s a set of decisions about what you still intend to do, and for most of the people we work with, the second half of that list is the better half: the trip, the gift, the business handed on well, the grandchildren taught by being taken along.

Neither one is really about mountains. Stay honest about where you are. Keep a little challenge in the plan. And don’t assume your best adventures are behind you.

Ridgeline Wealth Advisors

On Adventure: Lessons from the Edge

Recent conversations from the On Adventure Podcast – and what they have to say about the lives the rest of us are building.

Every so often we like to set the individual episodes down side by side and notice the thread running between them. This time the thread is service – the quiet, unglamorous kind. Not the sort that gets announced, but the sort that shows up as staying at the back of the group so nobody walks out alone, or handing a stranger what he needs before you know his name.

It’s a financial idea as much as an adventuring one. Most of the people we admire in this work didn’t build their lives around what they could accumulate. They built them around who they could carry. Here’s what stayed with us.

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

Alex Potts grew up in Sunnyvale, California, riding BMX bikes through apricot orchards that would eventually become Silicon Valley, raised by a single mom who taught elementary school. He spent more than three decades helping build Loring Ward, one of the firms that helped pioneer the fee-based model independent advisors use today – and then, still in his fifties, he stepped away from the top job.

What we appreciated most was his refusal to make service sound noble. Alex talks about it as a habit, not a virtue: helping advisors and clients solve problems that actually mattered instead of chasing assets or wallet share. The same habit shows up on the trail. When someone is struggling, you help. You don’t ask whether they’re in your group, and you don’t run the math on what’s in it for you – because today it’s them, and tomorrow it’s you.

He’s also honest about the difference between fitness and wisdom. On a rim-to-rim hike through the Grand Canyon in 110-degree heat, in some of the best shape of his life, his body began shutting down a mile and a half from the top. What turned it around was a stranger and a bag of beef jerky. Being capable of pushing harder, it turns out, isn’t the same as knowing whether you should.

The line we keep coming back to is the frame he puts on his own story: for years, running was how he got away from the pressure of a demanding career and young kids. At some point it stopped being escape and became pursuit. Don’t spend a whole life running away from something. Find something worth running toward.

Listen to Episode 77 →

Episode 78: Adventure Has No Expiration Date with Beverly MacDowell

Most people know the MacDowell name from Beverly’s sister, actress Andie MacDowell. Beverly’s work happens far from any camera, and she likes it that way. A retired educator in Asheville, North Carolina, she went camping for the first time at 36, joined the Carolina Mountain Club in her fifties, started maintaining sections of the Appalachian Trail at 59, and began search-and-rescue training at 65. In her words: “The majority of everything I did was post-50.”

What we appreciated most is that nearly all of it is for someone else. She guides women over 60 on their first backpacking trips. She does the slow, physical work of keeping trails passable, including helping restore Max Patch after years of overuse, and she helped get people back into the Blue Ridge after Hurricane Helene. The only way you’d notice any of it is that the trail is still there, or that someone who thought they were too old to carry a pack made it to camp anyway.

She has a particular way of thinking about guiding. For Beverly, the goal isn’t to lead people forever. It’s to turn intimidation into confidence, so the people she guides can eventually go on their own. “A little challenge is good,” she says. She doesn’t take the hard part away. She makes sure nobody faces it unprepared.

It’s a useful way to look at retirement, too. Too often it gets planned as an ending – the day the paychecks stop and the drawing-down begins. Beverly’s story suggests it can be the start of your most useful years, if the plan leaves room for it. The money is there to buy the freedom to say yes: to the training course, the trail crew, the Tuesday morning with a group of nervous first-timers.

Time outside, she says, is “a balm” – and a few years of it “makes you a completely badass grandmama.” Adventure has no expiration date. Neither does the chance to show someone else the way.

Listen to Episode 78 →

What We Took From Both

Put these conversations side by side and the lesson from the edge is a simple one. The people who end up with lives worth describing are almost never the ones who optimized hardest for themselves. They’re the ones who kept showing up for the person next to them, and who learned – usually the hard way – when to push and when to turn around.

That’s close to how we think about planning. A good plan isn’t a number standing on its own. It’s the thing that lets you be useful to the people you love, take the risks worth taking, and step back from the ones that aren’t. We’re grateful to guides like Alex and Beverly for the reminder.

If this resonates, the full conversation is worth your time. And if you’d like to talk through what running toward something looks like in your own situation, we’re here and happy to help.

Ridgeline Wealth Advisors

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, 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.

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 McDowell, 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 McDowell 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.

Check out this episode!

On Adventure: Lessons from the Edge

Two recent conversations from the On Adventure Podcast – and what they have to say about the lives the rest of us are building.

Every so often we like to step back from the individual episodes and notice the thread running between them. The two most recent conversations on the On Adventure Podcast came from very different places – a bike-shop classroom on the California coast and a rotating string of mountain towns out West – and yet they landed in almost exactly the same spot. Both are about choosing the harder, fuller life on purpose, rather than drifting toward comfort or putting it off for some vague day down the road.

That turns out to be a financial question as much as an adventuring one. So here are the two, and a bit of what stayed with us.

Episode 75: Hard Things Are Worth Doing with Justin Smith

Justin Smith teaches high school in Santa Cruz, where his classroom is a working bike shop – teenagers learning to fix bikes, build résumés, and solve real problems with their own hands. On his own time, he’s an ultra-endurance athlete who has ridden the 2,700-mile Tour Divide from Banff to the Mexican border in sixteen straight days, raced the Fiji Eco-Challenge, and lined up at the Ironman World Championships in Kona.

What we appreciated most was how ordinary he made all of it sound. Justin talks about the “pain cave” – the dark hours before sunrise on day two of a race, when the body starts asking what exactly you’re doing out here – not as something to conquer but as a room you learn to redecorate and settle into. Comfort, he says, is what gets sold to us. Hard things are what actually move the needle. The line he repeats to his students and his daughter has stuck with us: a ship is safe in its harbor, but that is not what ships were built for.

Listen to Episode 75 →

Episode 76: Do It While You Can with Stefan Gruber

Stefan Gruber grew up in Raleigh, studied engineering at Western Carolina, and today works a remote job for a technology company he’s been with for about six years. But the more interesting thing about Stefan is what the remote job makes possible. Where a lot of us build our lives around our work, Stefan has quietly done the reverse – he’s built his work around the life he actually wants to live.

For the last couple of years, that life has been a moving target, in the best sense. When his wife Sarah began travel nursing, the two of them packed a car and a trailer and started following her contracts – Bozeman, where they later got married in Glacier; Idaho; and now Colorado Springs, in the shadow of the Garden of the Gods. Almost everywhere they land, there’s climbing within twenty minutes of the front door. Stefan describes climbing the way Josh describes the trail: one of the rare activities where you’re so locked into the next move that everything else – work, stress, the noise – simply melts away. He’s an unusually good photographer, too, a habit that started when he found an old camera lens in his parents’ attic and went looking for the camera to match it.

He was refreshingly honest about the cost. Living on the move means no steady circle of friends – the hardest part, he admitted, of the whole adventure. But when Josh asked him to boil it all down to one lesson, Stefan didn’t hesitate: get out and do these things while you can. We only live once, we’re a little older every day, and the experiences, he said, end up meaning more than any car or house ever could.

That’s a sentence we think about a lot on the financial side of the desk. The only real value of money is in its use – spending it on what’s genuinely of value to you, whatever your version of that is. It’s easy to spend a whole career building bigger buckets for a someday that keeps receding, only to arrive less healthy, less able, or not at all. Stefan’s life is a working argument for the alternative: decide what matters, and go live some of it now.

Listen to Episode 76 →

What We Took From Both

Put the two side by side and the lesson from the edge is really one lesson. The worthwhile life rarely happens by default. It gets chosen – on purpose, against the pull of comfort, and without waiting for permission or for the perfect moment that never quite arrives.

That’s the heart of how we think about planning, too. A good plan isn’t about the number for its own sake. It’s about being able to do the hard, meaningful things on purpose, to stay present through the long stretches, and to spend a life – not just save for one. We’re grateful to guides like Justin and Stefan for the reminder.

If either of these resonate, they’re worth a full listen. And if you’d like to talk through what you want your own version of “do it while you can” to look like, we’re here and happy to help.

Ridgeline Wealth Advisors

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 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

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.”

Check out this episode!

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: 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.

Check out this episode!

On Adventure: What We Carry

Lessons from Gil Jackson and Aaron Saft

Every long walk is an exercise in deciding what matters enough to carry. Ounces add up over thousands of miles, and eventually you strip down to what is essential. In our two most recent On Adventure episodes, I sat down with a Cherokee language educator and an ultrarunning coach whose lives revolve around a version of that same question: out of everything you could hold onto, what is worth the weight?

Gil: Walking Home

Gil Jackson grew up in the Snowbird community of western North Carolina in the 1950s – no television, no car, one light bulb per room, and a tight-knit Cherokee community where everyone showed up when a neighbor needed help. When he left for college in Georgia, his mother laughed and said, “You’ll be back.” He was gone almost 40 years, then built a house 200 yards upstream from where he was born and poured himself into the work that now defines his days: keeping the Cherokee language alive.

Only about 130 fluent speakers remain, and they are losing roughly two and a half a month. Gil calls it the eleventh hour. He thru-hiked the Appalachian Trail in 2014 to experience some portion of what his ancestors endured on the Trail of Tears, and conceded the biggest difference: he got to come home. But what moved me most is what Gil does off the trail. He spends his days locating sacred Cherokee sites in the mountains and taking younger people to them, so the stories and routes are not lost. The elders who know where these places are can no longer reach them. The young people who can make the climb do not know they exist. Gil is the bridge.

Aaron: What Do You Need?

Aaron Saft has finished Hardrock, UTMB, Leadville, Western States, and the Bigfoot 200. But the moment from our conversation that will stay with me had nothing to do with a finish line. It was his description of what happens when you come across another runner sitting on a rock in the middle of a 100-miler. You do not ask, “How are you?” You can see how they are. You ask, “What do you need?” And then you give whatever you have. Aaron said it is not a decision people make in the moment. It is who the sport turns you into.

He pins an upside-down photo of his family to his quad so that when he looks down at mile 80, he sees his wife and kids looking back at him. His son now runs for the University of Portland. His daughter, a high school freshman, just competed at the state championships. When other parents ask how he got his kids into running, his answer is simple: he did not. He just showed them what was possible. He even rebranded his coaching business – from “MR Running Pains” to “Running is Life” – because the words we wrap around our work shape the experience. Training is 99 percent process and 1 percent celebration. If you cannot find joy in the process, you are missing the whole thing.

The Same Trail

Gil is preserving a language and the sacred geography of his people. Aaron is building runners who understand not just what to do but why. Both told me the point was never the miles. The miles were just the means of discovering what mattered enough to hold onto. Not every adventure happens on a trail. Some happen when you ask someone what they need and mean it, or when you pass along something that would disappear if you kept it to yourself.

Stay safe and stay on adventure.

— Josh

You can listen to the full conversations with Gil Jackson and Aaron Saft on the On Adventure podcast, available wherever you get your podcasts.

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

Check out this episode!

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 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

Check out this episode!