Legendary investor and traveler Jim Rogers joins the show to share wisdom from his two epic global journeys, one by motorcycle and one by car, that set world records. Jim discusses how he retired early from Wall Street to see the world, sharing insights on how on-the-ground travel informs his investment strategy and why he chose to drive a bright yellow Mercedes through 116 countries. From being held "hostage" by a police chief in the Congo to his philosophy on exploring the unknown, Jim encourages listeners to embrace the uncomfortable and go where they haven't been before.

Guest:

• Legendary investor and traveler who retired early from Wall Street to hit the open road.
• World record holder for land travel, having driven over 100,000 km across six continents on a motorcycle and over 245,000 km in a car.
• Author of Investment Biker and Adventure Capitalist

Chapters:

1. From smalltown Alabama to retiring early from Wall Street
2. Seeing the world through an investor's lens
3. Being held hostage by a police chief in the Congo
4. Using a yellow Mercedes convertible as a safety precaution
5. Navigating border crossings and curiosity versus greed
6. Economic models: Seeing countries change for the better
7. Why Chad is next on the travel list
8. Jim’s advice: Go somewhere, especially if it is not comfortable

Resources and Links:

• Jim Rogers Website

Call to Action:

Check out our website at oneofftravelstories.com. If you enjoyed this episode, please subscribe, rate, and review the podcast.

When a last-minute invitation took Matt Wilson to Iceland to document climate change and adventure tourism, it started out as a typical outdoor adventure. He met a backcountry guide, rode “super jeeps” across rivers, and climbed a glacier at midnight. However, while sitting with new friends above the clouds admiring volcano peaks in the distance he also hatched the idea that became his future business.

Guest: Matt Wilson

• Co-founder & CEO, Under30Experiences
• Author of The Millennial Travel Guidebook
• Longtime digital nomad; based in Puerto Rico

Topics Covered:

1. New York grind to unexpected Iceland invite
2. Meeting Siggi and exploring Iceland’s backcountry
3. Super jeeps, river crossings, and glacier sunsets
4. Seeing climate change at the glacier’s edge
5. The mountaintop brainstorm that sparked Under30Experiences
6. Startup Iceland, the U.S. Embassy, and the President’s house
7. From one retreat to a global travel community
8. What’s next: new trips and building impact through travel

Resources and Links:

• Under30Experiences: under30experiences.com

Call to Action:

• Check out our website at oneofftravelstories.com
• If you enjoyed this episode, please subscribe, rate, and review the podcast.
• Share your favorite travel stories with us on social media using #OneOffTravelStories.

In this episode, Andrew sits down with Anne Marie Wells to hear about her solo hitchhiking trip across Iceland, where she spent weeks asking strangers one question: “What is your happiest memory?”. From there, she would venture out to visit the scene of the memory. Anne Marie shares the emotional highs and quiet moments that defined her trip and how curiosity and courage opened doors she never expected.

Guest: Anne Marie Wells

• Poet, playwright, and author
• Creator of the books Write Some Cool Sh!t and Mommy, Why am I a Bird?
• Upcoming memoir Happy Iceland
• Website: annemariewellswriter.com

Topics Covered:

1. Why Anne Marie chose to spend her 30th birthday in Iceland
2. The origin of her “happiest memory” question
3. Conversations with strangers across Iceland’s landscapes
4. Unplanned encounters and the kindness of locals
5. The emotional impact of traveling solo with purpose
6. How the experiment became a forthcoming book
7. Lessons on spontaneity, reflection, and joyful connection

Resources and Links:

• Anne Marie’s website: annemariewellswriter.com

Call to Action:

• Check out our website at oneofftravelstories.com
• If you enjoyed this episode, please subscribe, rate, and review the podcast.
• Share your favorite travel stories with us on social media using #OneOffTravelStories.