Jonathan Yaffe: From Vagabond to AnyRoad Entrepreneur

Jonathan Yaffe on the Love Affair Travel podcast with Ian Robinson
Courtesy of Any Road

What if you wanted to start a school?

Not just any school, you wanted to teach the California school curriculum while teaching students about organic farming, yoga, robotics and more?

Would you do it if you lived in Japan? Would you do it if you didn’t have any money? Would you do it if you didn’t even speak Japanese?

Jonathan Yaffe started there. The success of the school was one of many enterprising stories he shares today on the podcast.

Along with founding schools, art galleries and co-working spaces, he’s now working on another fascinating project. As co-founder of AnyRoad, their goal is to empower tour guides around the world to come online and connect with adventurers.

In this podcast, Jonathan describes his origin story. He tells some wild stories that inspired his love of learning, ethical travel and his favorite addiction, sushi.

“He said, ‘You’re 23. You’re broke. You’ve never been a teacher before. You don’t speak Japanese. How are you going to do this?’… And I somehow got him to fund the school.” – Jonathan Yaffe on finding investors for the KAI School of Tokyo

Travel Topics:

  • Jonathan’s first big adventure to Manaus, Brazil [2:57]
  • On the mindset shift of traveling with a one-way ticket [6:20]
  • Tales from the gateway of the Amazon: Manaus, Brazil [7:40]
  • The Radiohead experiment along a jungle river gone wrong [9:47]
  • How to sneak out of Brazil when your visa expires [12:20]
  • How after 2 years of no work he finally ran out of money [15:55]
  • On being stranded in Japan with one pay check [17:50]
  • A dream school in Tokyo [19:53]
  • Finding a passion worth committing to for 2 years [23:30]
  • How to do what the California public school system does and more – Robotics, Organic Farming and Yoga [26:25]
  • His mission – To build a school where you know everyone [29:25]
  • What’s next? A Tokyo Gallery! [31:01]
  • How Tokyo’s trash turned out to be an amazing opportunity [32:38]
  • The secret to scaling your business…. is implicit trust [35:55]
  • The Kilimanjaro trek that changed everything [38:10]
  • Researching with guides from all around the world [41:20]
  • What happened when bringing 95% of local tour guides online [44:19]
  • How to see a hidden part of The Great Wall of China [46:40]

Jonathan Yaffe’s Talking Points:

      • AnyRoad – Jonathan’s most recent pursuit, is bringing tour guides all around the world online for better wages, better services, and a better price for adventurers. 
      • Jonathan found himself in Japan when he decided to teach abroad with the Japanese Exchange and Teaching program
      • At 23, Jonathan recognized a hole in the Tokyo private school market and started Kai School that is still growing to this day.
      • After becoming immersed in the Tokyo arts community, he opened galleries and work spaces throughout the city.  
      • Connect with Jonathan:

 Instagram | Facebook | Twitter

Music Credit:

Take Action:

Jonathan was a fearless traveler from a young age and continues to jump at the chance to travel more and start great companies. What can you create without fear?