Millennial Travel Podcast

The Story of with Founder Casey Fenton

Matt Wilson
December 9, 2020

Casey Fenton is the founder of Couchsurfing, a global travel community, especially great for solo travelers. Casey helped to spearhead the sharing economy & grow the platform to over 20 million users worldwide.  I consider the platform to be one of the best domestic and international travel hacks and for solo travel on a budget.   Casey is also co-founder of Upstock, a cloud-based platform to give employee equity in the company they work for.

If you don’t know the meaning of “couch surfing” it’s basically where you stay on someone’s couch when traveling, or at least that’d be my definition of couchsurfing.  The platform Couchsurfing however doesn’t mean you have to sleep on someone’s couch… The point of Couchsurfing is  to “share authentic travel experiences” and your host will put you up in their home absolutely free. 

In this episode of The Millennial Travel Podcast I discuss with Casey Fenton, Founder of Couchsurfing: 

  • His story of traveling to Iceland
  • How a trip to Iceland was an impetuous for him starting Couchsurfing and us starting Under30Experiences. 
  • The story of how Couchsurfing started
  • How Casey flew to Iceland as a solo traveler and decided to find a couch to sleep on with locals
  • Why Casey loves Iceland and has traveled their five times
  • The quick story how Under30Experiences started.
  • Why Casey Fenton is starting his new company in Iceland and is mentoring Iceland Startups
  • How they picked the name “couchsurfing”.
  • How Casey Fenton got the “travel bug” and considered himself an explorer. 
  • How he got over a break up by traveling and buying plane tickets to random places. 
  • Casey Fenton’s formula for intensity, diversity, and frequency of experience, and how he got out of his comfort zone. 
  • His idea for “hacking destiny”. 
  • What Casey Fenton learned about himself traveling? 
  • He learned to be less shy, and improved himself. 
  • Some examples of how Casey traveled to different places and how Couchsurfing was a great travel hack for saving money
  • Casey Fenton’s idea of “ego hacking”.
  • The book that opened up Casey’s eyes that we are all sleep.
  • How a silly fight with his best friend opened his eyes to a lot of things about life.
  • Casey’s idea of a “feedback ratio”. 
  • Why it’s important to have ego and how we can use it as a tool. 
  • How we can avoid suffering through non-attachment
  • How to learn to trust yourself more and let others trust you. 
  • Casey finishes talking about his startup Upstock and how you can incentivize employees with equity to anyone in your company with his tool. 

Resources from Casey Fenton:

Listen to the full episode on Apple Podcasts, Stitcher, Soundcloud, Spotify, or YouTube.

You can find all the links and past show notes on

Direct support for The Millennial Travel Podcast comes from The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life.

Looking for more great content? Check out The Ultimate Guide to Solo Travel.

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...