Ep 33: How to live a Hobo-entrepreneur lifestyle – with Chris Kirkland

chris kirklandSome people dream to make enough savings during their work life so that they can finally travel to paradise destinations. Some others don’t wait to be old to live this freedom lifestyle. That’s the spirit of a nomad entrepreneur, or a Hobo-entrepreneur as my guest Chris Kirkland like to call himself. (Their is no fundamental differences between the two, apart from the second wearing shabby pants and being more self deprecating.)

Chris embraced a hobo-entrepreneur lifestyle since 2006 and has lived in several places including the Chiang mai, Saigon, London, and Tokyo. He explains how he first started to live according to his own terms and shares with us the ups and downs of living a nomadic lifestyle.

We discuss the various ways people can start living and traveling at the same time. As Chris explains, age shouldn’t be a limit for people. But he also admits that living such a life involves dealing with lots of uncertainties. So we go over a few techniques that can help people dealing with their fears.

Living a hobo-entrepreneur life involves creating money supplies, so Chris talks about his latest venture called Tokyo Cheapo. It is a website targeting foreigners traveling or living in Japan whose mission is to dispel the myth of Tokyo being an expensive city. This online guide help visitors find lots of places and tips to live and travel cheaply in Japan. With over 150,000 monthly readers, Chris explains how he manages his business while having a completely remote team.

Questions: If you had a money supply, would you adopt a hobo-entrepreneur lifestyle? What are your main concerns with this freedom lifestyle? (reply in the comments)

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  • (3:26) Introduction of Chris, a hobo-entrepreneur
  • (7:58) Ups and downs of a nomadic life
  • (14:55) How to manage your fears
  • (21:32) Is there a best age to start a hobo life?
  • (24:48) How to start a hobo lifestyle?
  • (26:32) Hobo communities
  • (28:05) Tokyo Cheapo
  • (33:18) How to manage a business remotely
  • (36:52) How to get traction
  • (39:12) Business model, advertising and ebook
  • (42:46) Quick-fire questions

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