Alex Boylan has spent most of his life saying “yes” before he felt fully ready.
From moving to Brazil alone at 15 years old… to winning The Amazing Race 2… to building a career producing travel television and creating The College Tour, Alex has consistently leaned into discomfort, curiosity, and opportunity.
But this conversation goes way beyond television.
Alex and Pat Sitkins discuss:
becoming comfortable being uncomfortable
taking the first rep before you feel ready
keeping your “backpack” light
perspective, travel, and gratitude
a look at Alex’s book The Miles That Make You: How to Make Life an Epic Journey
aging parents and becoming a father
why most people stop themselves too early
and how staying curious can completely change the trajectory of your life.One of the most thoughtful, grounded, personal, and hopeful episodes of Two Types of People so far.
00:00 — Welcome Alex Boylan
02:15 — Comfortable vs Comfortable Being Uncomfortable
05:40 — Why the First Rep Matters
09:20 — Get Off Your Cell Phone and Look Up
10:00 — Moving to Brazil at 15 Years Old
12:00 — The Amazing Race Changed Everything
15:15 — Why Some People Stay Stuck in One Era
21:30 — Perspective, Aging Parents & Fatherhood
24:00 — Keep Your Backpack Light
28:00 — Rock Bottom, St. John & Starting Over
31:00 — Building The College Tour
“Those who are comfortable… and those who are comfortable being uncomfortable.”
“Get off your cell phone and look up.”
“You’re gonna suck at first.”
“Most of the rest of it is all in your own head.”
“Life’s amazing. This planet’s amazing.”
“Keep your backpack light.”About the Show
Two Types of People is a bi-weekly podcast hosted by Bestselling Author, Agency CEO, and Executive Producer Pat Sitkins - exploring the patterns, decisions, and mindsets that shape high performers across business, sports, and culture.
The show features conversations with contributors to the book Two Types of People: Insights from Top Performers to Help You Make Decisions, Act, and Grow and other leaders whose experiences bring the framework to life. The book is currently available for pre-order at all major retailers.
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