Apple Google Overcast

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

More about Chris:


Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here



    Want To Join 5300+ People For A Weekly Reflection On Work, Life & Philosophy?