Episode 72: Risk in Every Form with Greg Winchester
On Adventure Podcast with Josh Self
Release Date: 05/29/2026
Episode 73: Running is Life with Aaron Saft
On Adventure Podcast with Josh Self
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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...
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Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black
On Adventure Podcast with Josh Self
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Episode 70: Saying Yes to the Right Invitations with Colin Stroud
On Adventure Podcast with Josh Self
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On Adventure Podcast with Josh Self
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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...
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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...
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Episode 66: The Adventure Within - Finding Strength, Meaning, and Hope through Adversity with Hilal Kanaan
On Adventure Podcast with Josh Self
In today’s episode, I sit down with Dr. Hilal Kanaan - neurosurgeon, son of Palestinian immigrants, and someone whose daily work places him in the quiet but profound landscapes of human suffering, endurance, and compassion. While he isn’t chasing adventure in the traditional sense, Hilal spends his days navigating a different kind of wilderness: the emotional and spiritual terrain of walking with people through their hardest moments. We explore the kind of toughness that’s forged not on trails or mountaintops, but in operating rooms, hospital corridors, and the inner worlds shaped by...
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Episode 65: Why Suffering Becomes a Spiritual Awakening with Scott Sauls
On Adventure Podcast with Josh Self
David Brooks describes life as a journey up two mountains. The first mountain is about achievement—building a career, proving yourself, chasing success. The second mountain begins when the first no longer satisfies, and you’re called into a deeper life of meaning, surrender, and service. This episode lives squarely on that second mountain. This conversation is the second installment in our series exploring where spirituality and adventure overlap, and it’s an honest look at what happens when ambition gives way to awakening. I sat down with Scott Sauls to talk about burnout, identity, and...
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Episode 64: Adventure, Spirituality, and the Search for Something Bigger with Reed Dunn
On Adventure Podcast with Josh Self
In today’s episode—the first in a brand-new series exploring the deeper meaning behind our outdoor experiences—I sit down with my longtime friend, pastor, everyday explorer, and deep thinker, Reed Dunn, for one of the most meaningful conversations I’ve had on this podcast. This first installment leans less on adrenaline and more on the why—why we’re drawn to the outdoors, why hardship shapes us, and why so many of us pursue experiences that push us into awe, wonder, and transcendence. Reed and I dig into the spiritual side of adventure—what it means to connect with something...
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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.
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Hosted by Josh Self, financial advisor and everyday explorer.
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