Travel Hacks, Profitable Side Hustles, and Storytelling with Chris Guillebeau


It’s not everyday you meet someone who’s travelled to every single country in the world.

After four years of living in West Africa as a volunteer executive, Chris Guillebeau (@193countries)  went on a lifetime quest to design a life of non-conformity.

He visited every single country in the world. But that was just the beginning.

Chris’s next goal was to inspire the world to live a life of non-conformity (Art of Non-Conformity), pursue lifestyle entrepreneurship ($100 Startup – 500K copies sold), happiness (The Happiness Pursuit), and now… help you earn more money on the side.

As a fan of traveling, entrepreneurship, and mission-driven projects, I’ve naturally been drawn to Chris’s work for years. I’ve previously interviewed Chris for Rype, so I wanted to try something unique with this interview by getting the audience involved.

In this (solo) episode, Chris answers questions I’ve curated from our own audience and myself. He drops bombs on topics around travel hacks, creating successful side hustles, public speaking tips, and much more.

Hope you enjoy! x

Questions Chris answers in the episode


  • What’s one (or two) game-changing travel hack(s) that very few people seem to know about?
  • If someone was planning a trip a few months out, what would be your recommended strategy to get the best deal possible? (i.e. airline name, aggregator website, day of the week, how many days/months in advance, etc.)
  • What’s a travel product that’s a must-have for you every time you travel (that few people know about)


Side Hustle/Success Principles

  • If you didn’t have your audience, personal brand, or connections, and you only had $5,000 to your name — what would your side hustle be and why?
  • What’s your advice for validating your side hustle idea for less than $100?
  • How do you know when to go all in (from side hustle to full-time hustle) or whether you should keep it as a side hustle?
  • On the other end, how do you know when to quit and move on to another idea?
  • What’s your process of setting effective and actionable goals ? (i.e. daily, weekly, monthly, yearly — physical journal, evernote, app, etc. — # of goals). Could you walk us through in detail on how you go about it?


Audience questions

  • What’s a piece of storytelling advice that you often come back to? -Josh Levitan
  • Is there a daily habit or routine that has had a big impact in your professional or personal life looking back?  -Bryan Wong
  • Best credit card for travelers and why? -Jackson Torres
  • As someone who’s as quest driven as you, there must be a deep underlying purpose that fuels it. The Japanese have a word called ‘Ikigai’ which means the reason you get up in the morning, what would your ‘ikigai’ be? -Anisia Zara
  • You’ve met and heard thousands of public speakers throughout your career. What do you think makes the difference between a good and an exceptional presenter? -Jesse A.


Show Notes


Order a copy of the book here.



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