Mr Kirkland

Serial entrepreneur, building since 2005.

© 2026 Mr Kirkland

Hello, I’m Mr Kirkland.

Since 2006 I’ve been a serial entrepreneur, having lived in Tokyo, Berlin, London and a few spots in South East Asia. These days I run a travel media company and I’m rebuilding it to run on AI agents.

About

I’m a fan of bullet points, I’m sure you are too, so:

  • Founder of Tokyo Cheapo and Fast Train Media — one of the largest English-language Japan travel audiences. Bootstrapped, and now in three cities: Tokyo, London and Hong Kong.
  • Currently transforming the company to run on AI agent pipelines — content, social, ad-ops and reporting.
  • Founded and sold artweb.com, a hosting platform and gallery for over 20,000 artists (acquired 2022).
  • 25 years of full-stack web, most of it while moving.
  • LP and mentor at Earnest Capital and Shizen Capital; advisor to Delphi Network and KYC-Chain.
  • Previously podcast co-host and writer at HoboCEO.com.
  • Occasional speaker. Retired headstander — the back catalogue lives at hbm.jp.
  • 300KTokyo Cheapo Instagram followers, up from under 10,000 in 2023
  • 4.5MYouTube views a year
  • 25,000articles published across the network

Press and speaking

I enjoy occasional public speaking, and have organised local travel industry events in Tokyo and Hong Kong.

Chris Kirkland speaking with a microphone at Travel Massive Tokyo, in front of a slide reading Always Travelling: The Location Independent Lifestyle
Speaking at Travel Massive Tokyo, March 2018.
Chris Kirkland interviewed in Fortune magazine
Interviewed in Fortune, August 2018.

Podcast appearances

The story so far

  1. Learnt to program BASIC on a ZX81 and a few other 8-bit machines.
  2. Decided to become a musician; joined a jazz group and a reggae band.
  3. Joint-organised the 300-strong Sussex University Amnesty International group.
  4. Spoke at a student conference in front of 1,000+ people. Organised a series of sell-out fundraiser concerts for Amnesty.
  5. The high point of a fairly small music career: played to around 1,000 people in the supporting band for Misty in Roots.
  6. Started learning HTML, JavaScript and PHP.
  7. Lost my first $50,000 to a failed business partnership.
  8. Released my first album, Magic Baby.
  9. Founded ArtWeb.
  10. Went to Tokyo on holiday, decided to skip my return flight and stay.
    Chris Kirkland doing a headstand on a street in Shibuya, Tokyo
    Shibuya, shortly after deciding to stay. More at hbm.jp.
  11. Started living between London, Berlin, Tokyo and South East Asia.
  12. Started Tokyo Cheapo and Hobo CEO.
  13. Japan Cheapo launched.
  14. London Cheapo launched.
  15. Network exceeds 1M uniques a month; Hong Kong Cheapo launched.
  16. Invested in Earnest Capital and Shizen Capital as an LP and start-up mentor.
  17. Exited ArtWeb.
  18. Cheapo network exceeds 1.5M uniques a month.
  19. Started growing the Tokyo Cheapo social media channels.
  20. Tokyo Cheapo YouTube exceeds 100,000 subscribers and Instagram exceeds 250,000. Monthly social media reach overtakes website reach.
  21. Instagram passes 300,000 followers. Marketing automation and agentic workflows running across sales, accounts and content.