Episode 162: Adventure on a Need-to-Know Basis with Craig O’Boyle

“The nature of not having a huge plan was enticing to all three of us.”

— Craig O'Boyle

This week on the podcast, we’re thrilled to welcome Craig O’Boyle! Craig, a real estate entrepreneur from Colorado Springs, Colorado, lives by the mantra "work hard, play hard." Each year, he organizes a unique adventure for his close-knit group of friends, the self-dubbed “Outdoorsy Guys” (OGs). The twist? Craig is the only one who knows the destination. The rest of the crew shows up at the airport, ready to embrace the unknown.

In this episode, we dive into their unconventional approach to travel, the bonds forged through shared adventure, and the magic of stepping out of your comfort zone. It's a conversation about trust, spontaneity, and the joy of the journey.

Craig also discusses:

1:50 – The OG Trips: An introduction to the unique tradition of the “Outdoorsy Guys” and their annual adventures.
4:40 – The First Trip: How it all began and the story behind their inaugural journey.
8:50 – The Need-to-Know Basis: Exploring the dynamics of trips where only one person knows the destination.
12:30 – Pushback or Trust?: Did other members ever challenge Craig’s approach to planning?
14:15 – Guiding Principles: The values and rules that shape these unforgettable adventures.
16:00 – Surprises Over the Years: Reflecting on the memorable surprises that have kept the trips exciting.
26:10 – Skydiving Adventure: A look back at their most recent adrenaline-filled experience.
28:00 – Personalities at Play: How the group’s diverse personalities contribute to the success of these trips.
32:30 – Trust and Comfort Zones: The role of trust and stepping out of comfort zones in creating lasting memories.
38:00 – The Organizer’s Perspective: Craig shares what it feels like to earn such a high level of trust.
39:50 – Transformations Through Travel: How these trips have impacted the group’s lives and relationships.
42:00 – Why These Trips Matter: Craig reflects on the importance of these experiences in today’s world.
43:30 – DIY Adventure Tips: Advice for anyone looking to create their own trust-based, surprise-filled trips.
46:30 - Hollywood Dreams: If his life were a movie, who would Craig cast to play himself?