Interview with HoboCEO Chris Kirkland of Artweb

We are in the midst of a digital nomad revolution. The opportunity to live in low-cost foreign locales, while building businesses that reach the world has never been easier. There are already thousands of location independent startups roaming the globe, but this is only the beginning. Massively reduced living and business costs combined with endless opportunities to connect with like-minded entrepreneurs are a strategic advantage that traditional startups can no longer afford to ignore. No one epitomizes the new jetset citizen lifestyle better than HoboCEO, Chris Kirkland of I had the great fortune to meet up with Chris in Thailand and Japan recently. He shares his story in this interview.

Chris Kirkland HoboCEO of

 Please tell us about yourself?

Born in the UK, moved city three times before I was even 18, so perhaps a little bit of the hobo in me from an early age. I left home at 17 and have been pretty much financially independent ever since. I studied Mathematics at university, however study is perhaps the wrong verb since I spent most of the 3 years with my face cello-taped to a bong, in band rehearsals and whilst (relatively) sober organising the Uni Amnesty International group.

Skipping on the graduation ceremony (or even collecting my degree cert) I dived straight into self employment hippie naturalist oblivion. This took the form of a disastrous attempt at running a music/video/anything creative studio smothered with adjectives like universe, community and chi that eventually lost me about 50K EUR. The massive debts quite neatly catapulted me into a more sober and financially viable career as a freelance web developer and I was pretty much back in the black a year later.

Still naive and rather unbusinesslike I quickly ended up with a series of non paying clients and a “surprise” tax bill which once again led my financial health gauge to hovering around the zero mark.

The inability to pay one’s rent always being a good focusing technique led me to conceive the business that is now After only about 10 paying subscribers and a few years before the 4 Hour Work Week was even published, I was already plotting how I’d spend my days working from the beach in Goa whilst my bank account slowly filled up with wheelbarrows of cash.

Then quite randomly in late 2005 an old school friend suggested we all move to Japan. I thought that was an excellent idea, so I learnt Japanese booked a flight and almost eight years later am still waiting for my school friends to join me.

Now a days I’m running a couple of businesses (ArtWeb and Tokyo Cheapo) whilst simultaneously galavanting across the world and the internetz having assumed the identify of Hobo CEO.

Shibuya Headstand

Please tell us about your travels?

Before I arrived in Japan, I’d already seen some of Europe, a couple of trips to the states and a brief reconnaissance of working remotely in Goa.

But my hobo CEO adventure kicked off properly when I first ventured over to the Far East. I’ll save the Tokyo details for the question below, but after 5 years I decided to take off again and give Europe a go.

First stop was London, but after a few months my optimism and high hopes were dashed. Although I made a few friends, there were virtually no like minded traveling entrepreneur types – the London four hour work week meetup wasn’t exactly over subscribed. I quickly realised there was absolutely no need for me to stay in such an expensive, competitive and somewhat dangerous city, so I booked a flight to Berlin packed my single cabin luggage suitcase and was gone just like that.

Berlin is/was awesome. I’ve been visiting regularly for over 10 years in fact, so it’s almost a second home for me. Any day in Berlin typically includes, continental breakfast al fresco and random conversation with the people at the next table, shopping for organic sauerkraut at one of the ubiquitous organic supermarkets, kebab for lunch for less than 3 EURs, laptop session, meetup or meeting in one of Berlins many coworking spaces, Vietnamese Pho for dinner 5EUR, then rolling around on the floor with strangers at a contact improvisation ‘Jam’, and bonus points for getting an early night so you can get up at 6am and start clubbing (night clubs typically don’t get going till about 3am and stay open most of the weekend). Add to all this the still remarkably low rental prices, Berlin is a hopspot for hobo CEOs.

Apart from a few months in London and Berlin, I’ve been back and forth between Europe and Asia, other highlights include Cluj (Romania), Hawaii, Chiang Mai (Thailand), Ho Chi Minh City (Vietnam), Penang (Malyasia), Hokkaido (North Japan) and recently Tokyo again.

Generally I’m not traveling because I’m on holiday, I’m more focused on work, so I tend to favour tech/hobo CEO hotspots and places with plenty of internet connected cafes.

How does Vietnam compare to Thailand or Chiang Mai specifically?

I’m pretty new to Ho Chi Minh City but so far I’d say it is the big city antidote to Chiang Mai. Both are great value in terms of standard of living, plenty to do and good to stay for a few months of focus. Definitely more foreigners in Chiang Mai, but there seems to be a higher density of entrepreneur types in HCMC, far fewer travelers and if you’re looking to hire people locally for business (like developers, PM, designers etc) HCMC has much more on offer.

If I were Knit picking I’d say Chiang Mai has more healthy eating options and outside the rice field burn season (March/April), the air quality is much better. The internet in HCMC was definitely a grade above most of my Thailand experience though we still had a couple of power outages (during which I carried on work via tethering my phone).

Please tell us about your time in Japan?

Tokyo was my first real expat experience and it proved to be an addictive one.

“Welcome to Japan – it’s like Disney Land crossed with Blade Runner”, I recall someone saying when I first arrived, and indeed it was as exciting and bizarre as being cast as the replicant character played by Rutger Hauer in Disney remake of Blade Runner.

It wasn’t all Disney animated roses though. Whilst Tokyo is perhaps the safest city in the world, as a foreigner (and perhaps also native resident) you’ll find high barriers to entry all over the place, high prices, langauge, cultural differences and incredibly complex social rules perhaps being the tallest. But on the flipside this filters out a lot of people so Tokyo has a high density of really smart, motivated and hard working people. Like some of my some super successful friends – Rob Laing and Matt Romaine founders of or Mike Sheetal co-founder of And of course my partner in crime for Greg Lane.

Whilst the first few Tokyo years were a ball, my luck changed with the financial crisis. With the income from ArtWeb almost entirely in GBP and sterling sinking against the yen like a unicorn strapped to a cannon, I soon found myself back to student level finances in what was now the world’s most expensive city.

And so the halving in value of my pounds slowly ushered me out of the country, and for the last two years I’ve pretty much been on the road, with just shorter spells in Tokyo.

How did you get your visa to stay in the country.

I arrived on a tourist visa. I extended it to 6 months whilst I figured out how to apply for a work visa. I hired an scrivener (kind of lawyer) who sorted everything out for me for about 400GBP.

Since I have a UK limited company it was possible for me to get a work visa for running a “representative office” in Tokyo, the main problem was that I had to actually rent an office space (which I’d never go to). I wrote all the full details in a blog post here:

The last two years I’ve just entered on a tourist visa since I’m only there a few months of the year.

How do you make money? is my income source, we help artists market and sell their artwork through building and managing their web presence – basically a niche for artists. It’s a subscription business model and we have a few thousand happy users. It’s a great business, we’re providing real value in helping non techie types leverage the internet to promote and sell their artwork, plus it’s rewarding from a geeky perspective in that I get to play around with load balancing, cloud computing and all kinds of nerdy optimization 🙂

Recently I’ve launched which is a content site and to be the first of a series of living/travel guides for expensive cities round the world. It’s already generating 50K page views a month and some revenue, but I’m investing in it for now, so it’s not a source of income yet.

How long have you been doing Artweb?

I started Artweb on my own about 7 years ago and it wasn’t until about 5 years ago until I started hiring anyone. Now we’re a team of 6, everyone is essentially location independent and we’re seldom in the same timezone, let alone same city.

When you first started, how did you get your initial customers?

I started with some direct mail, emails and cold calls. My first direct mail blast (about 30 people) landed me my first customer, so straight out the gate I felt like I was on to something. Quite early on I offered a large artist organisation my tech skills in exchange for endorsement/sponsorship and that was great source of new customers in the beginning since it gave the service exposure to almost 1000 artists. Apart from that a little bit of “white hat” SEO plus our organic growth (word of mouth and other referrals) has always been a good draw of customers.

Please tell us about

Tokyo Cheapo is a Cheapo’s guide to living in or visiting Tokyo. We cover everything from sumo to sushi, plus accommodation, romantic cheapo date ideas and we often photoshop dogs and kittens into the photos on the site. It seems like we’ve hit a winning formula with useful information, not taking ourselves too seriously and unashamed cheapness.

For me this is epitomized by the numerous likes and funny comments on a recent facebook status on our fan page:

“just botched an upgrade on our server, obviously being cheapos we’re doing it ourselves rather than hiring a professional.”

(We’d never get away with this on ArtWeb!)

Does that site make much money for you yet?

So far it makes a pittance ($100/month) from google adsense, but we’re not trying too hard to monitise at the moment, more focusing on building the audience.

Long term advertising will be the key revenue source, plus we’ll release some some mobile apps when we have a number of cities and can leverage our data onto mobile devices. I also envision a series of T shirts and merchandise with slogans such as “Cheapo and Proud… Cheapo Planet” etc.

What do you think a Cheapo living and traveling budget is for Tokyo per month?

Cheapo residents in Tokyo are going to struggle to get by on less than $2000 per month – I survived on about $2500 per month living in a fairly hip central neighbourhood, though if you’ll willing to live in a less central area you can rent places super cheap and could conceivably bring this down to $1500 or even less.

For travelers check out our 3 days in Tokyo on $120 article – if you don’t mind sleeping in a reclinable chair for a few nights this is totally doable. Apart from that, whilst you can see lots of sights for free and food can be quite cheap, accommodation is always going to be the big expense for budget travelers. Hostels start around $20 per night – see our accommodation section for our cheapo recommendations.

Please tell us about your membership in the Dynamite Circle.

I joined the DC almost by accident. A friend of a friend recommend I and my partner in crime Nico Appel attend the Bangkok conference. I’d never heard of the DC before but within 20 minutes we’d booked and paid for the conference and 3 months of membership – it didn’t seem like a lot of money and we’d been planning on a trip to SEA about that time anyway, so we thought worst case scenario it was just a reason to write down our flights as a business expense.

The conference itself blew us away. Up to that point my hobo existence had been quite a lonely and I had only have a handful of true location independent friends. Being in a room of 70 other hobos was without doubt the high point of last year for me. Having such affirmation of my hobo lifestyle (as opposed to the oh so common lack of understanding or plain simple resistance from most people) made something in me click into place and ever since I’ve plunged into any opportunity to reach out and connect with fellow hobo’s and DCers.

Aside from all the awesome business advice, the social effect alone makes DC membership worthwhile for me. Being able to turn up to a new city, have multiple friends on the ground ready to meet me with all the good cafe working spots already mapped out is gold.

What’s next for you?

Businesswise I’ve just started out on a new podcast for hobo CEO – we’ll be covering the more ‘meta’ side of location independence – mindset, minimalist lifestyle and futurist philosophical banter. To me location independent lifestyle is the current frontier of human existence and it seems inevitable that it’ll become more and more mainstream. However I think the main things holding it back are not logistical concerns (like how will I earn money) but more cultural inertia and mindset.

Location wise, I’m currently in Tokyo and off to Berlin in a few weeks for the summer.


Personal sites:

Business sites:

Twitter: @mrkirkland

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My name is John Bardos. My wife and I gave up our business, house and possessions in Japan to search for more meaning and fulfillment in our lives. We've discovered that a satisfying life is about rich experiences, quality relationships and meaningful contribution, NOT consumption.

3 Responses to Interview with HoboCEO Chris Kirkland of Artweb

  1. Great interview, John. Filled with a lot of useful links. Tokyo Cheapo is sweet, I definitely put similar tactics to use visiting Peru.

    • John says:

      Thanks Tony,

      I appreciate you taking the time to comment. How was Peru? We’re hoping to make it to South America this winter as well.


  2. John & Chris,

    Hot stuff guys. It’s great to hear the nitty gritty, elbow grease and all side of being a digital nomad. You’re obviously a very focused chap Chris. Kudos for all the success and savvy strategies. I’m very new to the world of online business, having just started blogging 3 months ago. I relish hearing tales of those who’ve made their dream of a location independent lifestyle a success.

    All the best for the future.

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