Episode 72: Risk in Every Form with Greg Winchester
On Adventure Podcast with Josh Self
Release Date: 05/29/2026
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...
info_outline
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...
info_outline
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,...
info_outline
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...
info_outline
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_outline
Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black
On Adventure Podcast with Josh Self
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...
info_outline
Episode 70: Saying Yes to the Right Invitations with Colin Stroud
On Adventure Podcast with Josh Self
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...
info_outline
Episode 69: No One Was Waiting at the Finish Line with Madison Blagden
On Adventure Podcast with Josh Self
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...
info_outline
Episode 68: Who You Become When There's No Way Out with Robbie Lenfestey
On Adventure Podcast with Josh Self
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...
info_outline
Episode 67: How to find God in Solitude, Silence and Wilderness with Bishop Mark Beckman
On Adventure Podcast with Josh Self
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...
info_outlineON 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