Two Types of People with Pat Sitkins

Alex Boylan: The Miles That Made Him

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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.

    CHAPTERS

    • 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

      • QUOTABLE MOMENTS

      • “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. 


        Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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        Two Types of People with Pat SitkinsBy Pat Sitkins