Lessons from 13 years of entrepreneurship & living nomadically (Chris Kirkland)
04/03/19 • 52 min
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:
- Support the podcast on Patreon
- Subscribe to the free weekly newsletter on our modern conception of work
📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
- Twitter: @p_millerd
- Instagram: @pathlesspaul
- Paul’s Newsletter: Subscribe to Pathless (23k+ People)
- Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
- Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
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:
- Support the podcast on Patreon
- Subscribe to the free weekly newsletter on our modern conception of work
📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
- Twitter: @p_millerd
- Instagram: @pathlesspaul
- Paul’s Newsletter: Subscribe to Pathless (23k+ People)
- Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
- Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
Previous Episode
Creating Art Filled With Magic (Martha Balaile)
Martha Balaile is a fantasy illustrator living in Cape Town, South Africa originally from Tanzania. Her mission is to figure out how magic, mythology and fantasy can have an impact on real life. She’s also the wonderful creator of the new cover art for this podcast.
Martha aspired to create “art that is filled with subtle lessons on living a magical and adventurous life.” Two of the lessons she has found:
- Go with the flow
- Be aware of fear
We explore these a bit and she shares some examples from fantasy that have inspired her. Check out the show!
We talk about:
- What drove her to pursue an art career after growing up in Tanzania
- What she wishes she learned in art school
- What she looked from working with clients
- How she switched from magic “standard” art to art she cared about
- How she decided to take the leap to freelancing “early” in her career.
- How she structures her day around her work
Her Top 3 Magic Podcasts:
Mythology Studios: Work With Martha
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Boundless / Reimagine Work:
- Support the podcast on Patreon
- Subscribe to the free weekly newsletter on our modern conception of work
📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
- Twitter: @p_millerd
- Instagram: @pathlesspaul
- Paul’s Newsletter: Subscribe to Pathless (23k+ People)
- Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
- Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
Next Episode
Beyond Average: Co-Creating A Life & Company (Tanya Zhang & Wesley Kang, NimbleMade.com)
Wesley Kang and Tanya Zhang are the co-founders of Nimble Made, an e-commerce clothing brand that makes “actually slim” dress shirts.
Before taking the leap to work full-time on their business, they worked in the corporate world in New York City. As first generation Asian-Americans, they had achieved “success” - good jobs, good salary. They were on their way. However, deep down both wanted something a little more. Some of Tanya’s challenges working as a freelance graphic designer on the side convinced them they should try to think a little deeper about building a brand and a business, instead of just helping other people.
As they found themselves thinking about the business all day at their full-time jobs and coming home ready to work on it, they realized they finally had to go all-in. Over the past year they have worked on the business and are starting to find some traction. As they’ve dealt with the challenges of running a business, they have also had to constantly reflect on how to manage a relationship both as committed partners and co-founders.
Check Out Nimble Made (unsponsored):
- Interested in their shirts? Check out more at Nimble Made.
- For their past reflections check out Wesley's guest post on entrepreneurship and Tanya's post on how her father inspired her to start the company.
Boundless / Reimagine Work:
- Support the podcast on Patreon
- Subscribe to the free weekly newsletter on our modern conception of work
📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community
📲Connect + Follow Paul
- Twitter: @p_millerd
- Instagram: @pathlesspaul
- Paul’s Newsletter: Subscribe to Pathless (23k+ People)
- Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
- Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
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