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Chris Kirkland is a bootstrapped entrepreneur who has been living nomadically since 2006 and is the founder of several web businesses including artweb.com and tokyocheapo.com.

We talk about how he has experimented with money, creativity, health and his lifestyle over the past 13 years. His nomadic journey started when he took a trip to Japan and after two days decided “fuck it,” I’m going to stay a bit longer.

We talk about his journey, entrepreneurship and his life experiments

  • Why entrepreneurs are really risk averse
  • His learnings from living nomadically and stoic exercises of living minimally
  • Prioritizing time over money as a bootstrapper
  • How running an online business was different in 2006 and why he “felt like he was cheating”
  • His experiments with becoming a “breatharian” and trying polyphasic sleep (do not try these at home)
  • How he thinks about running an online media business in 2019
  • His recommendations for cheap eats in Tokyo

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