Episode 32: Epic Adventures and Life Lessons with Skip Schweiss
On Adventure Podcast with Josh Self
Release Date: 09/20/2024
Episode 46: The Great Nearby - Chasing Wild in North Carolina with John Norwood
On Adventure Podcast with Josh Self
In this fun episode, Josh sits down with John Norwood, a commercial banker from Raleigh, North Carolina, whose second identity is that of a passionate adventurer. While John’s day job revolves around numbers and negotiations, his soul is stirred by trails, waterfalls, and sunfish sails. Rather than jetting off to exotic lands, John finds endless wonder in his own backyard—the mountains, lakes, and coastlines of North Carolina. Together, they explore John’s lifelong connection with the outdoors, how he blends adventure with a full-time career, and how he’s cultivated a community of...
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Episode 45: What's worthy of your finitude with Patrick Moody
On Adventure Podcast with Josh Self
I love these conversations, but this one was fun. We hit on the depths of the human condition to drive each of us on to our own adventures. So what happens when a dedicated trial attorney makes adventure a non-negotiable part of his life? In this episode, I sit down with Patrick Moody, a prosecutor for the state of Montana who refuses to let a demanding career keep him from chasing adventure. From trail running right out his back door to tackling high-altitude mountaineering, Patrick has found a way to integrate the wilderness into his daily routine. We dive into his experiences...
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Episode 44: From high heels and fashion to hiking boots and fly fishing with Kimberly Brookshire
On Adventure Podcast with Josh Self
What would you do if failure was a real possibility? If suffering was inevitable, but you had the option to walk away? Would you still go for it? My guest today, Kimberly Brookshire, knows this challenge well. She’s a long-distance hiker, a women’s adventure guide, and a passionate fly fisher—always choosing the hard path, the uncertain path, because that’s where she finds the most growth. In this episode, Kimberly shares her journey from fashion and city life to hiking thousands of miles on some of the toughest trails in the U.S. and beyond. She opens up about why she keeps pushing...
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Episode 43: Beyond the Pavement with Frank Trotter
On Adventure Podcast with Josh Self
What do banking and backcountry exploration have in common? More than you’d think! In this episode of the On Adventure, I sit down with Frank Trotter—banking pioneer, entrepreneur, and avid adventurer. From his early days racing cars in Europe to co-founding EverBank and now launching Battle Bank, Frank shares how his career has been driven by innovation and a passion for pushing boundaries. But it's not all business—Frank also dives into his love for outdoor exploration, from summiting 14ers in Colorado to backcountry treks in Argentina. We talk about the lessons learned from extreme...
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Episode 42: Endurance, Exploration, and the Art of Adventure with Roy Malone
On Adventure Podcast with Josh Self
What does it take to push your body and mind to the limit for days on end—while relying entirely on a team? The answer is epic! In this episode, I sit down with seasoned adventure racer Roy Malone, who has spent the past 24 years competing in some of the toughest endurance races in the world. From trekking through the jungles of Fiji to navigating the badlands of North Dakota, Roy shares the highs, the lows, and the life lessons that come from competing in these multi-day, non-stop races. We dive deep into the mental and physical grit required to finish these extreme challenges, the...
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Episode 41: A Journey of Resilience and Rediscovery with Jenna Carroll
On Adventure Podcast with Josh Self
In this episode of The On Adventure Podcast, I sit down with Jenna Carroll, a hiking guide and endurance athlete who transformed her life by stepping off the corporate treadmill and onto the Appalachian Trail. Jenna shares her incredible journey, from her early days as a basketball star and management consultant to finding her passion for long-distance hiking and trail running. We delve into her 2021 northbound thru-hike of the Appalachian Trail, her life-changing decision to make the outdoors her career, and her remarkable return to the trail in 2023 to attempt a self-supported fastest known...
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Episode 40: Courage, Connection, and Living Fully on Adventure with Wells Jones
On Adventure Podcast with Josh Self
What does it mean to live a life of adventure, and how do the challenges we face shape our purpose? In this episode, we sit down with Wells Jones, author of the gripping novel A Line in the Sand and a man whose life has been anything but ordinary. Wells shares his journey from his days as a Navy Air Rescue team member to his experiences as a producer, actor, and adventurer. Our conversation touches on his transformative treks through the Middle East, retracing the steps of T.E. Lawrence (Lawrence of Arabia), and how those experiences inspired his new novel. Wells also opens up about the...
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Episode 39: 2024 Year in Review
On Adventure Podcast with Josh Self
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Episode 38: From the Wilderness to the Operating Room with Dr. Tommy Gavigan
On Adventure Podcast with Josh Self
In this episode of the On Adventure Podcast, I catch up with an old friend and fraternity brother, Dr. Tommy Gavigan. From our days at the University of North Carolina to his current life as a practicing surgeon in Charlotte, Tommy’s journey has been anything but conventional. After college, Tommy spent nearly a decade guiding teenagers into remote wilderness areas with Moondance Adventures—experiences that shaped not only his leadership but also his path into medicine. We explore the connection between pushing past your comfort zone in the backcountry and managing high-stakes...
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Episode 37: Paying off $225,000 of student loan debt to fuel big adventures with Matt Miner
On Adventure Podcast with Josh Self
In this episode of the On Adventure Podcast, I sit down with my friend and former colleague, Matt Miner, to talk about his unique take on adventure. From growing up in Seattle and Tucson to now running his own wealth management firm, Matt shares the pivotal moments that shaped his life and career. We explore what it means to embrace life’s challenges, how intentional planning creates opportunities, and why staying true to your values makes all the difference. Whether it’s his love for the outdoors, paying off substantial debt, or helping his kids prepare for adulthood, Matt’s story is...
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In this episode of the On Adventure podcast, I sit down with Skip Schweiss, a seasoned executive in the financial services industry and a passionate adventurer. Known for his years of leadership at TD Ameritrade, Skip has seamlessly woven his professional life with a personal quest to push physical and mental boundaries in the great outdoors. We dive into Skip's career journey, from his work in advisor advocacy to how he's now dedicating more time to his love of the wilderness.
But Skip isn’t just about hiking the occasional trail—he organizes an annual group hike called "Excellent Adventures," attracting dozens of people to tackle challenging hikes across some of the most beautiful landscapes in the U.S. From the majestic peaks of Colorado’s 14ers to this year’s adventure in Telluride, Skip shares his motivation for doing hard things, the camaraderie that comes from shared suffering, and why he believes that testing our limits makes us better.
Whether you're a seasoned adventurer or someone looking for inspiration to push past your comfort zone, Skip's stories will encourage you to set bigger goals, embrace the challenge, and find joy in the journey.
Episode Highlights:
[2:42] - Skip’s journey in the financial industry, his role at TD Ameritrade, and how his love for adventure began.
[7:00] - How the Rockies ignited Skip’s passion for hiking, leading him to complete all 54 of Colorado’s 14ers.
[12:15] - The origin of Skip’s “Excellent Adventures” group hikes, which have now grown to include 70 people, and the importance of camaraderie in adventure.
[29:00] - Handling adversity on the trail: The lessons Skip has learned about staying calm when things go wrong, and how to apply that mindset to life.
[40:30] - A recap of the most recent “Excellent Adventure” in Telluride, where Skip led a group on a brutal 26-mile hike with 8,000 feet of elevation gain.
[52:00] - What’s next for Skip and the group? A sneak peek into next year’s adventure to Zion National Park and some of the epic hikes planned.
Links & Resources:
- Learn more about “Excellent Adventures” and past trips on the Tiburon Advisors website: Skip & Chip's Excellent Adventures
- Book Recommendation: Deep Survival: Who Lives, Who Dies, and Why by Laurence Gonzales
If you enjoyed today’s episode, please take a moment to rate, review, and share the podcast! Don’t forget to follow us so you don’t miss out on upcoming episodes filled with more inspiring adventures.