shibuya headstand

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The Beginning

It all started in 2005, during a bad patch. I’d just been wiped out by an unexpectedly large tax bill and simultaneously dropped my two biggest clients, so I was feeling rather poor. I realised being a freelance web developer wasn’t the smartest business model.

I thought to myself “I’ve been building software that makes other people money, so why can’t I build something that’ll do the same for me?”

So I put pen to paper, code to server and came up with a couple of ideas for an internet based business. I pushed out a prototype of a artist’s gallery website builder after barely a couple of weeks work and emailed spammed a few local artists with the idea. About a week later I received a cheque in the post – money in the bank already, a good omen.

So I sent out more emails and started calling people too and over a month or so few more cheques trickled in. I had only a little business training so I sought advice from a friend who had already built a successful business. He did more than give me advice, in early 2006 we set up a limited company and we became partners. Phill pledged to work part-time on the marketing side of the business and provide a few thousand pounds for the business to expand.

We rented some proper servers, sponsored an art festival and had a stall at a couple of artist centric events. I continued to work on the code, design, features and marketing. Over the next few months more cheques started to come in, my phone was ringing more, and the business was growing.

Promotional Flyer

The Far East

At the same time as starting this new business I had a nagging desire to travel and live in some different countries, Japan was high on my list. I already knew that this business had potential to travel with me. Not long after I’d built and launched the prototype I went for a couple of weeks in Goa (India) and was able to keep an eye on things from internet cafes. So I had a goal of relocating to Japan at some point in the next year or so.

So in December 2006, about 9 months after the business officially launched I decided to fly to Tokyo for 5 week reconnaissance trip over the Christmas holidays. My plan was to check the place out and and make some connections for when I came back to live later on. I took my laptop, forwarded my phone number to Skype and hoped that I could work as normal between in between karaoke and scoffing sushi.

After two weeks, I’d all but stopped answering the phone, was much less distracted, more productive and the money kept coming in – I was having a ball and it was business as usual. I didn’t bother to get on my return flight home.

And I never went back ‘home’.

The Next 5 Years

Since then, I’ve carried on running the business as usual, spent most my time in Tokyo but with a few spells in some other countries (UK, Germany, Hawaii, Romania). The business has grown over 10 times in size, 5 people run the show from 5 different countries, and I’ve accrued a bucket load of unconventional work, lifestyle and travel experience.

And in this time I’ve experimented with long work hours, short work hours, taking advantage of time zone differences, co-working environments, working from cafes, on beaches and in between kite surfing. I’ve hired people to work with me on site, remotely and at great distance, good friends and complete strangers. I’ve mostly stopped doing meetings, answering phone calls, deadlines, calendars and schedules. Plus I’ve had a lot of time and freedom to experiment socially, physically, mentally and think outside the box.

So stay tuned! Next I’ll start going into specifics and share with you the results of my experiments as a ‘hobo CEO’. I’ll write my thoughts and experiences as honestly as I can, in the hope they’ll prove useful and give some inspiration to thinking outside the box.

Cheers for now!

shibuya headstand

Visiting Shibuya in Dec 2006


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