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!

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 73: Running is Life with Aaron Saft


ON ADVENTURE PODCAST |  EPISODE 73

Episode 73: Running is Life with Aaron Saft

As a species, we only do things if there is truly a reward on the other side. So when the reward is pain, struggle, suffering, and danger, what exactly keeps driving us back out the door?

Aaron Saft has spent his life chasing that answer. A five-time ACC champion at NC State whose teams finished third at the NCAA Cross Country Championships, he traded the track for the trail, ran his first 100-miler in 2016, and has since become one of the most experienced ultrarunners in the Southeast. Today he coaches roughly 75 athletes full-time through his Running Is Life platform and podcast, a business he deliberately renamed from “MR Running Pains” because he believes running, done right, should bring as much joy as it does suffering.

His résumé reads like a bucket list for the sport: the Grand Slam of Ultrarunning, the Bigfoot 200, Hardrock, Leadville, UTMB, and the Tor des Géants in the Italian Alps, where a fall, a head injury, and a watchful medic ended his race. He has finished a 100-miler while spiking a 100-degree fever, outrun a mother grizzly and her cubs in Canada, and learned the hard way when to push and when to stop. But ask Aaron why he does it and he won’t point to a trophy. He’ll point to the upside-down photo of his family pinned to his quad, the one he looks down at in the darkest miles to remember who he is suffering for.

In this conversation, Josh and Aaron trace the many forms the “why” can take. They dig into presence, learning to run a hundred miles one mile at a time, and the moment an empty drop bag at Leadville taught Aaron everything he needed to know about the generosity of the trail community. They talk about the one question you never ask an ultrarunner, the evolution from chasing a place to simply chasing the finish line, why legacy is something children catch rather than something we teach, and how an abundance mindset shaped the coaching practice he built from the ground up. It is a conversation for every everyday explorer about doing the hard things that make life fuller, right now, not someday.

Episode Highlights

•     06:00  The Terry Foxworth connection and the heart of On Adventure: the reward beneath the suffering

•     15:00  Running Is Life: why words matter and reframing the sport away from pain

•     19:00  From reluctant soccer goalie to cross country, and the high school coach who changed his life

•     24:00  The NC State years: five ACC titles, redshirting, and racing the steeplechase

•     28:00  Virginia, mentor Ben Thomas, the run shop, and the move into trail running

•     33:00  First 50K to first 100: the long adventure runs that planted the seed

•     37:00  What 100 and 200 miles teach you that a marathon never will: presence, mile by mile

•     38:00  Finishing the Grand Slam and the Wasatch 100 with a 100-degree fever

•     44:00  When to keep going and when to stop: the Tor des Géants head injury and a fevered DNF on Mount Mitchell

•     52:00  Intrinsic motivation, the family photo on the quad, and the “debt” a race director taught him about

•     55:00  The empty drop bag at Leadville and the generosity of the trail community

•     59:00  “What do you need?” The only question you ask an ultrarunner

•     01:01:00  Adventure versus performance, “level 49,” and racing for the finish line instead of the place

•     01:08:00  Legacy as something caught, not taught, and raising two runners of his own

•     01:13:00  From brick-and-mortar to online coaching: 75 athletes, an abundance mindset, and a teaching heart

•     01:25:00  Rapid fire: the grizzly bear, the Altra Lone Peak 9+, best and worst races, and five 100-milers in one summer

Resources and Mentions from This Episode

Here are the people, places, and resources Aaron mentioned in this episode:

•     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

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!

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


ON ADVENTURE PODCAST | EPISODE 71

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

          

Episode Description

What does it actually take to step on a plane alone, head somewhere most people would call risky, and come home a different woman?

Amanda Black is the founder of the Solo Female Traveler Network, a community of more than half a million women that started as a small Facebook group during her expat years in Australia. Ten years and roughly thirty tours a year later, she leads women into places the average traveler tends to avoid: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan, and beyond. Bali was the first trip. Seventeen women signed up. Nine of them ended up with the company logo tattooed by the end of it.

We talk about why she leans into destinations perceived as less safe, what real risk actually looks like versus the version we imagine, and why she pushes back on the idea that travel is simply safe or unsafe. Risk, she argues, is a spectrum and a muscle, and most women have a lot more capacity to build it than they have been told.

We also get into the quieter side of all this. The cobblestone cafe in Sighișoara, Romania, where women who had known each other only a few days started telling the truth about how lonely life back home really feels. The Golden Eagle Festival in Mongolia, where she felt like she had walked into a movie set with no electricity. The unexpected pattern she keeps noticing across every trip, every country, every group: people are not really upset about the hotel room. They want to belong.

Amanda also shares why she launched Kindred Community, a smaller, slower offering built around connection retreats in Southern California, and what almost a decade of leading women into the wild has taught her about courage, capability, and the kind of friendships that get a logo tattooed on someone’s wrist.

Episode Highlights

00:00  Welcoming Amanda Black, founder of the Solo Female Traveler Network

01:00  Building a community of 500,000+ women and running tours in 25 countries

03:00  Why she leans into destinations perceived as less safe: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan

05:00  How strangers become a travel family inside the first 48 hours of a trip

08:00  From a Facebook group in Australia to a first Bali trip where 9 of 17 women got the company logo tattooed

12:00  Talking honestly with women about safety, fear, and the gray areas of real risk

15:00  Risk on a spectrum: why “safe or unsafe” is the wrong question, and how to build the muscle over time

17:00  Mongolia and the Golden Eagle Festival: stepping into a place that felt like going back in time

20:00  What solo travel reveals about how strong and capable women really are

22:00  The hidden business lesson behind a decade of tours: everybody just wants to belong

24:00  A cobblestone cafe in Sighișoara, Romania, and the loneliness that surfaces when women finally feel safe to share

27:00  Kindred Community and the next chapter: building belonging closer to home

Connect with Amanda Black

Bonus for Listeners (Free Travel Quiz):

https://thesolofemaletravelernetwork.com/where-should-i-travel-next-quiz/

The Solo Female Traveler Network

Website: thesolofemaletravelernetwork.com

Instagram: @solofemaletravel

TikTok: @sofetravel

YouTube: @sofetravel

Amanda’s TEDx Talk

Shared Firsts: Redesigning how we find belonging

youtube.com/watch?v=xSaVJH2b5H0

Amanda’s Website

meetamandablack.com

Kindred Community

Website: kindredcommunity.co

Instagram: @kindred.sd

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 70: Saying Yes to the Right Invitations with Colin Stroud


ON ADVENTURE PODCAST  |  EPISODE 70

Episode 70: Saying Yes to the Right Invitations with Colin Stroud

                              

Episode Description

What if your next great adventure is not a destination at all, but a willingness to say yes to the breadcrumbs life keeps dropping in front of you?

Colin Stroud is a 26-year-old credit card rewards consultant, founder of Go Somewhere, and one of the fastest growing voices on LinkedIn in the points and miles space. He grew up in Fort Wayne, Indiana, the son of an OB/GYN and a nurse midwife who met delivering a baby together, and he was on track for a more traditional path until a six-week Spanish immersion trip to Oviedo at 16 cracked the world wide open. From there it was Italy on a $380 flight, a Catholic mission to Poland, an unlikely run at Ave Maria University in south Florida, an early marriage and a baby on the way before he had even graduated, and a first job in life insurance case design that he knew almost immediately was not it.

What followed is a story about paying attention. A coworker mentioned the Chase Trifecta. A LinkedIn post about points went viral and got picked up by The Washington Post. A side hustle turned into consulting calls, then into a community for business owners, then into a full-time business helping families and entrepreneurs unlock travel they thought they could not afford.

We talk about why early travel rewires you, what it actually takes to leave a steady paycheck, the difference between dopamine and meaning, why family life and entrepreneurship feel like the truest adventures of his life right now, and the surprising decision he and his wife made after almost moving to Hawaii. Colin makes a strong case that the go somewhere life is not always about getting on a plane, and that learning to be rooted where your feet are can be its own kind of expedition.

 

Episode Highlights

00:00  From cheap flights as a teenager to a full-time business helping people unlock travel

06:00  World Youth Day in Poland, six weeks of Spanish immersion in Oviedo, and catching the travel bug

14:00  Marriage, a baby on the way, and a first job in life insurance that did not fit

18:00  Discovering the Chase Trifecta and stepping into the points world

23:00  The first viral LinkedIn post and a Washington Post quote that changed everything

25:00  Quitting in November 2024 and going full-time on Go Somewhere

30:00  Almost moving to Hawaii, pumping the brakes, and rethinking what travel does for young kids

34:00  Why family life and entrepreneurship are the truest adventures of his life right now

39:00  Measuring yourself: finally finding feedback after years of feeling stuck

47:00  The two ingredients behind a viable internet business: clear writing and consistent humility

55:00 What adventure means now and where to find Colin online

 

Connect with Colin Stroud

LinkedIn: linkedin.com/in/colinstroud

Website: gosomewhere.world

Newsletter: The Go Somewhere Newsletter at gosomewhere.world

Email:

 

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

Subscribe to the Patreon for more content!

If this episode resonated with you, leave a review and share it with someone who needs to hear it

Check out this episode!

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden


ON ADVENTURE PODCAST  |  EPISODE 69

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden

 

   

   

Episode Description

What would it take to walk 10,000 miles in a single calendar year? Not across a lifetime. Not spread over a decade. One year.

Madison Blagden is a long-distance hiker and content creator from Massachusetts who went from a pre-med student with zero backpacking experience to one of the most prolific endurance hikers in the country. After completing the full PCT (2022), the Eastern Continental Trail from Key West to Newfoundland (2023), and the Continental Divide Trail (2024), she did all three Triple Crown trails back to back in 2025, border to border, logging over 10,000 miles in a single calendar year. She documented every step herself through daily YouTube videos, Instagram shorts, and blog posts, all edited on the road.

Starting in the Florida Keys in January, she pushed through Hurricane Helene damage on the AT, Sierra snowpack, desert heat, a debilitating hip injury in the White Mountains, and a flash flood that hit her tent in the middle of the night in the desert. The miles are extraordinary. But this conversation goes deeper than the miles.

We talk about what happens between the ears when the body wants to quit, the difference between healthy internal ambition and ego-driven achievement, how the most meaningful finish lines are the ones where nobody is waiting for you, what a flash flood teaches you about calm under pressure, the spiritual dimension of pushing past absolute exhaustion, and why you will never be 100 percent ready, and that is not a reason to wait.

 

Episode Highlights

•       00:00  Introduction: Walking 10,000 miles in one calendar year

•       02:00  Madison’s background: pre-med to PCT with no backpacking experience

•       04:00  Van life, COVID, and two years of traveling in a 19-foot RV

•       09:00  Comparing the AT, PCT, and CDT: terrain, culture, and difficulty

•       14:00  Hurricane Helene’s impact on the Appalachian Trail and trail recovery

•       19:00  Planning a 10,000-mile year: budget, timing, and keeping it flexible

•       24:00  How a 5,600-mile year sparked the idea to go even further

•       31:00  Funding the hike through daily content creation on the road

•       34:00  Healthy ambition vs. ego-driven achievement

•       39:00  Internal motivation: the David Goggins voice and the gentle encouragement

•       42:00  37 miles a day for nine weeks: the math behind finishing the CDT before snow

•       48:00  Hip injury in the White Mountains and the lesson in letting go

•       51:00  Flash flood survival and what it reveals about fight-or-flight

•       57:00  Nervous system training and calm under pressure

•       01:02:00  Surrendering control: giving it up to the trail and the universe

•       01:05:00  Spiritual experiences that emerge only at the edge of physical exhaustion

•       01:10:00  Coming off trail softer: how big accomplishments quiet the ego

•       01:15:00  Closing encouragement: you will never be 100 percent ready, so go

•       01:20:00  The expanding ceiling of human limits and what comes next for Madison

 

Connect with Madison Blagden

Instagram & YouTube: @madisonblagden

Website: madisonblagden.com

Substack: substack.com/@madisonblagden

The Trek: thetrek.co/author/madison-blagden

 

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 68: Who You Become When There’s No Way Out with Robbie Lenfestey


            
Season 4 kicks off with a return visit from Robbie Lenfestey, who you may remember from episode 21. Robbie lives on Mandala Springs, a 67-acre retreat center in the mountains outside Asheville, North Carolina, and he was right in the middle of Hurricane Helene. What followed was months of disaster relief, community leadership, and eventually a very long-overdue exhale. In this conversation we get into what it actually looks like to be the calm person in a room full of panic, how a lifetime of pushing physical and mental limits builds a nervous system that can handle almost anything, and what Robbie means when he talks about the real frontier of human experience. We also talk breathwork, Internal Family Systems, flow state, a cryptid spotted multiple times on his property, and a Costa Rica trip that simply could not have been planned. This one goes deep.

Episode Timeline

  • [2:43] Hurricane Helene hits Mandala Springs and what the property looked like after
  • [5:00] The Cherokee sweat lodge log jam that accidentally redirected the flood and saved the structures
  • [10:03] On a tractor all night while landslides crashed down the mountain
  • [13:41] Taking charge the morning after and what it means to be the regulated nervous system in the room
  • [24:09] What flow state actually is and how a lifetime of edge experiences builds access to it
  • [27:29] Internal Family Systems – separating from an emotion long enough to actually work through it
  • [35:56] Breathwork, the Wim Hof Method, and the ancient Tibetan roots behind it
  • [41:22] Six months of nonstop disaster relief and the bonfire moment when the grief finally released
  • [47:17] What higher power means to Robbie and why embodied spirituality matters more than head knowledge
  • [54:55] The Wampus cat at Mandala Springs, seen by multiple witnesses

Links and Resources

If you enjoyed this episode, I’d really appreciate it if you’d rate, review, follow, and share the podcast. And don’t forget to subscribe to our social channels, including our YouTube channel and our Instagram, Facebook and LinkedIn pages. It’s one of the best ways to support the show and stay connected. Until next time, stay safe and stay On Adventure.

Check out this episode!

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


In this final installment of our series on spirituality and adventure, I sit down with Bishop Mark Beckman, the 4th Bishop of the Diocese of Knoxville, to explore what happens when faith is formed not just in quiet rooms, but in wild places. From hiking solo through old-growth forests to walking hundreds of miles on pilgrimage, Bishop Beckman shares how discomfort, silence, and physical effort can open us to something deeper than words.

We talk about the moments that push us to the edge of our capacity—storms in the backcountry, long days of walking, fear at high elevations—and how those experiences can shape trust, humility, and presence. This conversation is a reminder that adventure doesn’t only take us outward into the world, but inward toward meaning, mystery, and a deeper awareness of God.

Episode Timeline

  • [2:22] – Bishop Mark Beckman’s calling to ministry and how the outdoors shaped his faith from an early age

  • [6:45] – Discovering God’s presence through solitude, silence, and hiking alone in the woods

  • [10:48] – Forming a men’s backpacking group and finding unexpected community on the trail

  • [16:05] – Walking the Camino de Santiago and learning trust one step at a time

  • [22:40] – Pushing through fear and physical limits on a 14,000-foot peak in Colorado

  • [30:12] – Retreat, silence, and wilderness as pathways to deeper spiritual awareness

  • [38:05] – Suffering, endurance, and how hardship can deepen us instead of hardening us

Links & Resources

If you enjoyed this episode, I’d really appreciate it if you’d rate, review, follow, and share the podcast. And don’t forget to subscribe to our YouTube channel for full episodes and additional content — it’s one of the best ways to support the show and stay connected. Until next time, stay safe and stay on adventure.

Check out this episode!