Episode 75: Hard Things Are Worth Doing with Justin Smith
On Adventure Podcast with Josh Self
Release Date: 07/10/2026
Episode 81: Why We Need the Wilderness - Identity, Purpose & Soul Rest with Todd Pinkston
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...
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Episode 80: Living Your Great Life Right Now with Monica 'Moss' Aguilar
On Adventure Podcast with Josh Self
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...
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Episode 79: Why Altitude Humbles Even Experienced Climbers with Karl Frank
On Adventure Podcast with Josh Self
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...
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Episode 78: Adventure Has No Expiration Date with Beverly MacDowell
On Adventure Podcast with Josh Self
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...
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Episode 77: The John Muir Trail, Leadership, and Running Toward Adventure with Alex Potts
On Adventure Podcast with Josh Self
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...
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Episode 76: Summit Fever and Close Calls - Knowing When to Turn Back in the Mountains with Stefan Gruber
On Adventure Podcast with Josh Self
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...
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Episode 75: Hard Things Are Worth Doing with Justin Smith
On Adventure Podcast with Josh Self
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...
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Episode 74: Carrying a Language Home with Gil Jackson
On Adventure Podcast with Josh Self
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,...
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Episode 73: Running is Life with Aaron Saft
On Adventure Podcast with Josh Self
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...
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Episode 72: Risk in Every Form with Greg Winchester
On Adventure Podcast with Josh Self
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...
info_outlineWhat happens in the dark hours before sunrise on day two, when your body starts asking
what exactly you are doing out here?
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.
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.
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.
• 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
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/
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Hosted by Josh Self, financial advisor and everyday explorer.
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