Millennial Travel Podcast

Travel The World with Expert Digital Nomad & Travel Hacking Tips

Hannah Pinkerton
January 16, 2024

The Guests

  1. Chris Guillebeau is a New York Times Bestselling Author and he shares strategies to start your Side Hustle and ways to 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.
  2. Jordan Harbinger has always had an affinity for Social Influence, Interpersonal Dynamics and Social Engineering, helping private companies test the security of their communications systems and working with law enforcement agencies before he was even old enough to drive. Jordan has spent several years abroad in Europe and the developing world, including South America, Eastern Europe and the Middle East, and speaks several languages. He also hosts the Jordan Harbinger Show, one of the top personal development and business podcasts on the air today.
  3. Sarah Knight is the internationally bestselling author of “The Life-Changing Magic of Not Giving a F*ck,” which has been translated into eighteen languages and counting and has hit bestseller lists all over the world. She has also written “How to Get Your Shit Together” and her latest book “You Do You” was released in November 2017.
  4. Jodi Ettenberg founded Legal Nomads in April 2008 to document her long form travel writing and photography, after working as a lawyer for several years. In subsequent years, the site has won multiple awards and her business has expanded to include a book about food, celiac translation cards, public speaking, consulting work in social media and branding, and an eCommerce store featuring hand-drawn maps of food.
  5. Joe Di Stefano, CSCS, RKC – “Joe D.I.” as he is referred, is an international speaker, fitness expert, entrepreneur and coach. Joe is the Director of Sport at Spartan Race, the world’s leading obstacle racing organization. He is also the Founder of RUNGA, an off-the-grid experience designed to educate people on health and fitness, and connect them with their full potential.
  6. Matt Wilson is Adventurer and Co-founder of the travel company Under30Experiences. In just a few short years U30X has grown to 15+ countries worldwide and 30+ local communities throughout the USA and Canada. Matt is also the Co-Founder of Under30CEO (Acquired 2016) and the Host of the Live Different Podcast and has 40+ Five Star iTunes Ratings on Business, Travel, Health and Performance. He brings a unique, uncensored approach to his interviews and writing. His work is published on Forbes, Inc. Magazine, Huffington Post, Reuters, and is part of the invite-only Young Entrepreneurs' Council (YEC) comprised of the world's most successful entrepreneurs 40 and younger.

The Episode

Our episode today is all about travel... We are sharing some of our favorite clips from digital nomads, world travelers, and other travel experts on topics like how to avoid kidnapping, what it’s like to move from New York City to the Dominican Republic, and learning experiences from visiting every country in the world.

We went back into the archives and dug up a few excellent episodes that highlight some special travel stories and pieces of advice and we put them all together for you in today’s episode!

You will hear from authors, world travelers, bloggers, and more in this week’s episode of the Live Different podcast.

Topics Covered

  • How to overcome resistance to putting your creative work out in front of the world
  • What it means to be a digital nomad
  • Tim Ferris’ Four Hour Work Week and his phrase “lifestyle design”
  • Challenges faced living in the Dominican Republic versus New York City
  • How to not get kidnapped while traveling
  • What to do if you end up in jail abroad
  • Experiencing connections with other people when traveling
  • Implications of going off the beaten path when traveling
  • Tips on creating an environment of impossible failure
  • Lessons learned from traveling to every country in the world
  • Suggestions on working towards non-conformity on your own terms

Quotes from the Episode

“Lifestyle design is about designing your life and doing the things you want to do regardless of what society tells you. It’s all about trying to do the things that you want to do in life, rather than just work. That’s what digital nomads really believe in. (Matt Wilson)”

“The world is your oyster, you can move anywhere in the world. (Matt Wilson)”

“It’s about the connection to other people. If you truly stop and close your eyes and think about what is around you and open them wanting to connect in an authentic way, that’s far more important than that off the beaten path place that no one else has found. (Jodi Ettenberg)”

“Your attitude is way more important than where you go. (Jodi Ettenberg)”

“Let’s not add. Let’s take away. You can’t add a positive until you remove the negatives. If you want to really create change, the more of those things that you can remove from the equation that you don’t have to counter, the better. (Joe DiStefano)”

“The greatest learning [from visiting every country in the world] was much more about myself than it was about me gaining knowledge about every single culture or people group. (Chris Guillebeau

“You don’t have to live your life the way other people expect. As you go through life there is going to be all kind of people that have expectations for you. Ultimately you are choosing your life for yourself.”


The Life-Changing Magic of Not Giving a F*ck

The Jordan Harbinger Show

Legal Nomads Website

Legal Nomads eCommerce store


Side Hustle: From Idea to Income in 27 Days

Luz García Yoga

Say hi to Matt on Instagram

The 4-Hour Workweek by Tim Ferris

James Altucher

Forget Average: Be Your Sexy Self with the Blonde Gypsy

You do You by Sarah Knight

8 Things Nobody Tells You About Moving to the Caribbean

Becoming a Digital Nomad: How to Travel the World, Work Online, and Have a Life You Love

Be Who You Are And Use What You've Got with Sarah Knight

Be Over Prepared, Avoid Kidnapping, and Build Your Network with Jordan Harbinger

Travel the World, Find Your Niche, and Build Your Brand with Legal Nomad Jodi Ettenberg

Be Intentional and Breathe Your Way To Better Health

Make Side Money and Travel the World with Chris Guillebeau

Listen in Now, and build your vision for the future today!

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

Hannah Pinkerton
Hannah enjoys spreading love in the world through travel, blogging, and teaching Spanish. Her hobbies include exploring in nature, taking naps, and spoiling her two dogs. She is proud to use her organizational and list making skills as an Executive Assistant for U30X.


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