The Pathless Path with Paul Millerd

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:

Boundless / Reimagine Work:


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What is The Pathless Path with Paul Millerd?

The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.