April, 2014. Drunk. Laptop balanced on the sofa.
I booked a one way flight to Phuket on ba.com, then went to Tiger Muay Thai and put down a deposit on three months of training at a gym I’d never been to. The confirmation emails landed about a minute apart.
The next morning I woke up to the most blinding hangover of my life. But the money was gone. The flight was for the 1st of September.
I had six months to sort the rest of my life out!
What follows is the story I told my mate Chris Reynolds in 2015 when he had me on the Entrepreneur House podcast. A 14 year arc from a broke kid at uni spamming pyramid scheme links to his mates, to living with type 2 diabetes in Ho Chi Minh with a remote team of a dozen people and his health under control for the first time in years. Mostly it’s a story about how I spent six years failing on my own in Portsmouth, before finally letting a flat full of strangers do the work that willpower never could.
I originally recorded this interview shortly after leaving the Entrepreneur House in Barcelona, a four month experiment in living and working alongside other entrepreneurs that probably changed my life more than I realised at the time.
If you’re curious, I wrote about that experience separately here:
Barcelona – The Entrepreneur House with Chris Reynolds
2002: Pyramid Schemes And A Nintendo DS
The very, very beginning was 2002. I was at uni and extremely poor with no money. Same as everyone else around me.
Then I discovered these pyramid scheme sites. If you completed an offer online, and got five friends to complete the same offer with your referral code, you got a free Amazon voucher. You could then buy yourself stuff. Really unnecessary things. Televisions. A Nintendo DS, in my favourite case!
I ran around spamming my referral link to all my mates at uni, exactly like you’ve probably seen loads of people do on Facebook since. They all said no!
Right, plan B! I built a website promoting the offers, ran Google pay per click against the keyword free, and turned the whole thing in to an Amazon voucher fountain. For every $10 I put in to keywords I printed myself roughly $100 in vouchers. Decent ROI for a skint student!
That was my very first introduction to internet marketing. Except I had absolutely no idea what internet marketing actually was! I just thought I’d found a clever loophole.
You can’t eat Amazon TVs to survive though, so through a mate I landed my first real PHP job - building out a website for a trucking company. Remote. From a terraced house in rainy Portsmouth, of all places.
The idea of being a “digital nomad” really wasn’t in my vocabulary in 2002. So rather than cutting code in Bali or Chiang Mai or sunny Phuket, I worked from Portsmouth in my dressing gown, 7 in the morning until 10 at night, for a remote client, with the roar of Fratton park in the background.
It was a brutal lesson in how to actually quote a job and estimate time properly. The hard way!
Six Years Of Ploughing In To Nothing
I kept seeing the marketing stories from people like The Rich Jerk, kept thinking “well how do I do that?”, but I never had enough money spare for any of the courses. So I just kept registering exact match domain websites in my evenings and weekends, around the 9 to 5 day job, in niches I had no real passion for.
If you’ve ever held a 9 to 5 whilst trying to build something on the side, you’ll know how hard it is to plough energy in to a side project you don’t actually care about. I was building keyword websites for products I’d never use, in spaces I knew nothing about, half asleep. I technically knew what I was supposed to be doing. I just didn’t believe in any of it.
So nothing happened.
For five or six years.
That’s not a satisfying montage! That’s just five or six years of weekends where I’d sit down with the laptop, half-build something, give up, and go to the pub.
Two Grand On A Credit Card
Eventually I cracked. I put a couple of grand on a credit card and hired a few VAs to bang out articles and build backlinks. Boring SEO stuff, but suddenly I wasn’t trying to hand-roll every word myself.
Wednesday evening. Half past seven. The dashboard pinged. My first ever affiliate commission. About $27 to me!
I sat there staring at the screen thinking, well, that wasn’t supposed to work..
Five or six years of trying to create something new in my spare time. Overnight changed when I just decided to put a couple of grand on a credit card and take a risk.
That was the very beginning of the actual serious internet marketing finally taking off.
Looking back, the lesson was painfully obvious. I’d been trying to do everything myself, badly, for years. The minute I delegated the boring bits to people who actually wanted to do that work, the whole thing started moving.
Falling forwards, I call it. You’re not always in control, it’s not always good, you’ve just got to keep picking yourself up, pivoting if necessary and carry on going.
2013: Real Job, Side Hustle, And A Slow Disaster
By 2013 the SEO stuff was working and I was reinvesting all the proceeds in to selling physical products on Amazon. I was also still doing my day job.
Three things at once. Lot to handle!
Then I started to feel ill. Strange, vague ill. Tired all the time. Hungry all the time. Sleepy. I’d set the alarm for 7 in the morning to make it in to the office and wake up at half ten, half eleven, panicking. Thankfully I had a really understanding boss.
I went to the doctors. They sent me for MRI scans. They sent me to specialists. Private clinics. Nobody had a clue what was wrong with me!
In about nine months I’d gone from 70kg to 90kg. I’d ballooned. I wasn’t functioning. I couldn’t actually do my job any more.
I’d been to the doctors. They couldn’t find anything wrong with me. I’d put on all this weight, I wasn’t functioning, I couldn’t actually do my job.
One evening in September 2013 I started googling fat camps. Tyre retreats. Anywhere you could pay to be forced in to a better lifestyle. I was looking for somewhere to outsource my own willpower.
“I was looking for somewhere to outsource my own willpower.”
I found Johnny FD’s book - 12 Weeks In Thailand: The Good Life On The Cheap.
I sat at my desk at work the next day and read the whole thing on Kindle in one go. Didn’t do any work. Just read!
And it sounded like a plan. Quit the job. Go to Tiger Muay Thai in Phuket. Train Muay Thai every day. Lose the weight. Then go home and get on with life again. A reset, with kickboxing!
That afternoon I handed in my notice.
The next morning I asked for it back.
I’d looked at my bank account overnight and worked out I could afford a year in Thailand, but only just, and there wasn’t much wiggle room for getting it wrong. I lost my nerve.
My boss gave me my job back, which was nice of him. To be fair, I had spent the previous couple of years delivering a platform that earned the company about half a million dollars in profit a day, so I think we were roughly even!
I went back to my desk. Carried on with the project. Carried on getting sicker.
Idiot.
April 2014: A Drunk Decision That Actually Stuck
Six months later I got absolutely smashed.
At 10:04pm I logged in to ba.com and booked the flight to Phuket. Then I logged in to tigermuaythai.com and put a deposit down on the first three months of training.
The hangover the next day was the worst of my life. But I’d spent real money on a real flight, and that was the entire point of doing it drunk. Sober me would have asked for the job back again.
For whatever reason I decided the 1st of September was going to be the day. So I had six months to sort everything out.
I carried on working. Carried on getting sicker. Carried on getting fatter. Actually started drinking quite a lot to deal with it all, because the doctors still didn’t know what was wrong with me and the private specialists kept finding nothing. I was downsizing in slow motion - donating books to charity, clothes to charity, getting rid of anything that wouldn’t fit in one bag.
In August I gave my boss another resignation letter. This time I added a bottle of whiskey to it, by way of apology!
On the 1st of September 2014 my parents drove me to Heathrow. One bag in the boot. No flat to come back to, no job to come back to, no plan beyond the gym address.
That was it!
Eight Months On “The Street”

I spent eight months training at Tiger Muay Thai, living on “the street” right outside it, working on my Amazon and SEO businesses in between training sessions. Because I wasn’t really working a job any more - no boss, no client meetings, just training - I had five or six hours a day to put in to building stuff.
I started writing software for myself. Personal graphing tools to look at my own Amazon data. The kind of analytics dashboards I’d built for previous employers, but this time for me, and only for me. The plan, if there even was one, was to use it as a case study for my next employer when I got back to the UK.
The tool ended up being Amazooka.
Then in April 2015 I got really, properly ill again. Hungry all the time but losing weight. Asleep most of the day. I couldn’t train.
I went to the international hospital in Phuket. They took a blood test. They had an answer in about twenty minutes.
Type 2 diabetes.
I’d had it for about two years, undiagnosed, through about a dozen UK and Thai doctors. Two years of “we can’t find anything wrong with you”. And here was a Phuket lab tech finding it with a finger prick and a glucometer..
That explained literally everything. The weight. The exhaustion. The brain fog. The 90kg.
It also meant I had a proper problem now, not a vague one.
The Decision That Mattered Most
This is the bit Chris and I spent the most time on, because looking back it might be the most important decision I’ve ever made.
The natural thing to do, when you’re alone in Asia and you’ve just been told you have a chronic disease, is to go home. Fly back to England. Sleep in your parents’ spare room. Go to the GP. Be looked after.
I didn’t want to do that.
I also didn’t want to fly to some random European city and white knuckle it on my own.
What I actually wanted was a second opinion from a Western doctor I could sit in a room with, in a city where I’d be surrounded by people on the same wavelength as me. Working on online businesses. Building stuff. Camaraderie, but not pity.
I went online and found Chris Reynolds’ Entrepreneur House in Barcelona.
I paid him a deposit from Phuket and flew out a few weeks later!
I wanted a safe space. A community where I could fit in and deal with it. Not too much support, but just people who I’d be around for a solid length of time.
Vic Dorfman and a few of the guys in Phuket had been amazing whilst I was being diagnosed - I should name check Vic here because he was there for me when it counted. But there’s only so much anyone else can do. I needed to be in a room full of people who were busy with their own thing, where I could quietly fix mine in parallel.
Barcelona: 30 Strangers, 4 Months, A Different Person
Barcelona was awesome!
I’d spent my entire career so far on IT projects with other IT people. Developers, sys admins, dbas. In four months at the Entrepreneur House I must have met 30 or 40 entrepreneurs running businesses that were the polar opposite of mine.
Freddie was doing absolutely amazing things selling digital chess products with iChess. Neha was mentoring American kids through college from a flat in Spain. There were e-learning photography schools, agency builders, ecommerce wizards. Justin was doing phenomenally with his projects. Everyone was doing something I’d never personally touched.
I had a serious case of imposter syndrome for the first week. I genuinely wasn’t sure if these people had clocked yet that I wasn’t quite on their level.
Then the masterminds kicked in and that nonsense fell away. People shared not just what their businesses did, but what was broken about them. That takes massive character, to walk in to a room and say something’s up and we don’t really know what it is! That’s the bit no networking event ever delivers.
Once the masterminds were running properly, everything moved. People hit goals. People landed clients. People scrapped ideas and pivoted in to better ones. My own stuff started compounding too.
I gave up a bunch of vices. I went completely keto. I came off my diabetes medication. I walked everywhere. I joined a gym, decided I hated it, ditched it and just walked some more. I haven’t had a drink since!
I’m one year, two months and 23 days sober. Whilst I haven’t necessarily called myself an alcoholic, that’s stuck. And all of the other changes have kind of stuck as well.
By the time I left Barcelona my hba1c was where it needed to be and so was my weight! My diabetes wasn’t gone - it’s not the kind of thing that goes away - but it was completely under control with diet and exercise, no meds. I still see a doctor every three months. The numbers still look good.
You can’t really put a price on that 😀
Barcelona ended up becoming one of the most important periods of my life. I wrote more about the experience of living in Chris Reynolds’ Entrepreneur House here.
Amazooka, Accidentally
Here’s the bit nobody planned.
The internal Amazon tooling I’d been writing in Phuket caught the attention of some VCs whilst I was at the Entrepreneur House. They got hold of me on Skype with a proposal. It was a very good one.
October 2015 took me to Bangkok for meetings. June 2016 took me to Shenzhen, China for three months of handover. Then I was in Ho Chi Minh, Vietnam, sat on a Skype call telling Chris about how a personal passion project had turned in to a SaaS with investment, a remote team of a dozen people, and a roadmap that was about to change a chunk of the Amazon seller landscape.
I’d built it as a case study to show my next employer when I got back to the UK. Now it’s got investment. I’m being paid to work on it. I’m managing a remote team of a dozen people.
Falling forwards!
I made plenty of business mistakes building Amazooka - I treated it like a passion project, not a product, for far too long. But I also did a lot right from a software engineering point of view, because that’s the bit I actually knew how to do. Almost everything I did wrong turned in to a useful story later. Everything I did right turned in to a moat!
The Two Mistakes I See Everywhere
Chris asked me what the most common mistakes I see in business are, and I gave him two.
The first is not testing the market before you build the product. People design the thing in their head, fall in love with the vision, ship six months of work, then start hunting for someone who wants to buy it. The order is exactly the wrong way round. Fail fast, then build the thing the market actually asked for.
The second is doing too much yourself, badly, because your time feels free. I’ve done it for years myself. My time is unbilled, something is better than nothing, yada yada yada.
If you really believe in it, you’ve just got to take that risk. Get someone to do it properly now, even though you can’t necessarily justify the price, rather than hoping to make some money you can reinvest.
If you’re building something you genuinely believe will be with you for the next three or four years, get the right person to do the part you can’t do, even when the price terrifies you. Cheap, badly built foundations cost more than expensive, properly built ones. Every single time!
What Actually Keeps Me Going
Two things really. Fear of failure, partly. But mostly something simpler.
I have a picture in my head of the kind of person I want to be. A person who trains. A person who reads. A person who builds. A person who looks after his health. A person his friends can lean on.
If I want to live up to that picture, I’ve got to start acting like that person. Now. Today. At the gym. At the keyboard.
That’s the entire motivator.
Who do I actually want to be as a person? Then go and do the things that person would do!
A Few Closing Notes For Whoever’s Reading This
There’s a quote that came up in Chris’s house more than once, and I’ll steal it for the closer.
You are the average of the five people you spend the most time with.
If you’re in a room full of people who don’t build things, you’ll find it really hard to build things. If you’re in a room full of people who train, you’ll find it really hard not to train. I’d spent six years failing forwards on my own in Portsmouth. Four months in a room with the right strangers in Barcelona did more for me than the six years before it.
If you’re at a desk right now feeling vaguely ill and quietly stuck on something you’ve half built and don’t quite believe in - book the flight. Pay the deposit. Hand the boss your notice in August. Bring a bottle of whiskey when you do.
Sometimes changing your life starts with discipline.
Sometimes it starts with a drunken 2am flight booking you can’t afford to cancel in the morning. 😀
Original Materials
This article was adapted and edited from a 2016 conversation with Chris Reynolds on the Entrepreneur House podcast - “Conquering Health and Business By Controlling Your Environment”.
