Millennial Travel Podcast

Make Side Money and Travel the World with Chris Guillebeau

Matt Wilson
January 16, 2024

The Guest

Get prepared to meet New York Times’ Bestselling Author Chris Guillebeau and learn strategies to start your Side Hustle and learn how you can make money on the side and travel.

Chris is a writer, traveler, entrepreneur, and the author of the new book Side Hustle: From Idea to Income in 27 Days.

Five years ago, I remember staying in a hostel on the beach in Nicaragua for $7/night reading Chris’ original book The Art of Non-ConformityThis is a book that made dramatic impact on my life and inspired me to build Under30Experiences into what it is today. If you haven’t heard about Chris’ World Domination Summit, it’s a community I highly recommend getting involved with.  

The Episode

Do you know anyone who’s traveled to every country in the world?

Chris and I talk about what it’s like to see every country in the world and how creating such a massive quest for himself allowed him to get to know himself better, which almost always leads to greater confidence and levels of success.

I have the opportunity to ask Chris how he began to find his voice, especially as an introvert, and what other shy people can do to get out of their comfort zones.  

If you are wondering what’s next in your life or how you can start to earn money on the side, I highly suggest listening in to Chris’ advice. I truly enjoyed this conversation and knowing that not everyone has to take the same path to success and starting a side business should be easy and fun.

Listen until the end to find out Chris’ favorite book, country, meal, and worst side hustle he ever started himself.

Topics Covered

  • Success stories from the Chris’ Side Hustle School podcast
  • Chris’ side hustle that allowed him to see every country in the world
  • How to stay focused while balancing many projects
  • How to get to know yourself better
  • Lessons from seeing every country in the world
  • The Side Hustle framework
  • How to decide what your first side hustle should be
  • The formula to develop and cultivate a community
  • How to get started developing your voice

Quotes from the Episode

“My goal is not to serve entrepreneurs but to serve employees.”
“Ultimately I’m not going to be satisfied if I just focus on one thing.”
“I like the creative act of making things.”
“The greatest productivity hack is finding work that you look forward too.”
“You don’t have to live your life in the way that people expect.”
“At some point you just have to start and start sharing and trust the process.”


Side Hustle: From Idea to Income in 27 Days.

Side Hustle Book Tour

Side Hustle School Podcast

The Art of Non-Conformity  

World Domination Summit

Born For This: How to Find the Work You Were Meant To Do

Live Different Episode #40 Quit Your Job + Build a Successful Business with Sean Ogle

Captivate: The Science of Succeeding with People

Listen in Now, and start your side hustle!

You can get this episode directly to your iPhone on iTunes, your Android on Stitcher, or on Soundcloud.

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


last minute deals


As Seen In...