What does a 500-mile trek through Spain, a rain-soaked trail in Scotland, and a solo summit in Colorado have to do with building a meaningful life or business?
In this episode, we share the unexpected lessons learned from long-distance hikes, Ironman races, and conversations on the trail — and how they mirror the journey of entrepreneurship, leadership, and self-discovery.
From the spiritual silence of the Camino de Santiago to the muddy mess of the West Highland Way, this isn’t just a story about hiking — it’s about purpose, progress, and the people who walk beside us (or don’t).
If you’ve ever felt like the finish line didn’t fulfill you… this one’s for you.
KEY TOPICS
“Hike your own hike”: What this means for life, business, and ignoring the noise
Why the journey is the reward — not the goal or the finish line
What hiking in the rain teaches us about embracing discomfort
The real reason entrepreneurs hesitate to sell their businesses
How solitude reveals what you’re actually chasing
The power of walking with the right people, not just anyone
The Camino de Santiago’s secret economy, sacred history, and soul-deep meaning
How to follow the right signs — and know when someone else’s path isn’t yours
CHAPTERS
00:00 Introduction
00:51 Hiking in Scotland: The West Highland Way
02:18 Hiking Etiquette and Annoyances
03:28 Conquering Colorado's Fourteeners
07:51 The Spiritual Journey of the Camino de Santiago
14:44 The History and Experience of the West Highland Way
16:54 Group Hiking Dynamics
20:35 The Pressure to Grow in Business
21:07 Redefining Success: Progress Over Growth
21:50 A Lesson from the Parish Priest
22:56 Zappos' Unique Hiring Practice
23:59 The Importance of Human Connection
27:17 The Journey is the Reward
33:53 Lessons from Hiking
38:31 Embracing Hardship
41:21 Final Thoughts on Hiking and Life
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