I Built a Six Figure Online Business & Lost It: What’s Next?

A man walks past Durham Catherdal
Me leaving home over 10 years ago. One way ticket, £1000, terrified and no clue how to turn it around.

Originally published: August 3rd, 2015. (Edits at the end of article).

I wasn’t sure about writing this post and I’ve stalled on it for many months.

I’ve always been very open and candid about my financial situation, but then again – I’ve always been broke as a joke and it’s weirdly a lot more socially acceptable to talk about a struggle as opposed to openly celebrating economic success. It still feels surreal to say it out loud or via the written word; I built a six-figure online business in 1 year.

It feels terrifying to say that I lost a grip on it and it’s brought up some ghosts of the past that I thought I had put to bed.

For most of my life, I’ve been an embarrassing financial failure. I was raised by my mother with help from my grandmother and we, as the old English saying goes; “didn’t have two pennies to rub together.” I’ll spare you the; “we may not have had money, but we were always happy,” rhetoric because that would be a massive lie and I don’t want to give credence to that.

I used to buy ‘The World’s Richest’ updated list with my paper round money as a teenager. I know now that back then I fell into a trap that many do nowadays – thinking that simply reading books and learning inspiring quotes was enough to deserve wealth and a better life. I see it every day and I want to shake people because I know how much they are wasting their time reading and not actually doing anything.

Note: This is not to say I am bashing personal growth books, I am a fan of many. I am criticising reading them but not taking any action.

You reap what you sow and I chose to be a bum – bouncing from job to job without any direction, accruing huge credit card debt, perpetuating the vicious “get it on tick” cycle from the subculture I grew up in.

I Built a 6 Figure Online Business Way Ahead of Schedule

When I arrived in Chiang Mai, Thailand in 2011; things did not go according to plan. Bad health struck and a familiar tune was playing – I was down to my last $29 and I hadn’t made any money in weeks.

Also, I needed an operation for unexpected plastic surgery in Thailand, for which I didn’t have the money – I was forced into a fight or flight situation and it was the making of me as I cold-emailed quite literally every SEO agency on the planet (seriously if they were online, they got an email from me) with a proposal to advertise on my travel website, which was barely a year old.

I made a staggering $5000 that month (after never hitting $1,000 prior to that) and it gave me the confidence that I needed to go onwards and upwards. However, it really wouldn’t be fair to not give a shout-out to the legendary James Clark who helped me out with advice during a casual coffee in Chiang Mai’s Old Town that would change my life forever – for the best.

From that moment I turned into a raging workaholic. If I wasn’t chasing people for advertising contacts, hitting up advertisers, or writing SEO articles – I was trying out new ways to expand and make more money.

I was working like the hedge fund guys in American Psycho, sleeping 3-4 hours per day. I never turned down anything online which made me money. I must have personally written thousands of articles during this period. I have written for clients on a huge range of subjects; cities around the world, sex toys, interior design and I once wrote 7000 words on the menstrual cycle!

Predictably – I burnt myself out. But I just couldn’t stop because if I did I was leaving money on the table. A friend invited me to take a trip with him to Malaysian Borneo.

I love Malaysia, after all, it was here this crazy story began so it was a no-brainer and so off we went – grabbing our PADI Scuba Diving certificates in the process.

However, the trip turned out to be incredibly stressful as the more I rested – the more I left clients waiting and pissed off. When I got back I didn’t learn my lesson and I continued working myself down to the bone. Running on empty and constantly feeling like a zombie.

During this period I befriended Johnny Ward and he would constantly preach to me about working too much and how I should be treating myself for my hard work. I found it really annoying to be honest because you have to do what you have to do to grow.

With that being said, I was going hard and burning the candles at both ends.

What I Did as Soon as I Started Making Six-Figures Online

Roughly a year later I moved in with him and other online guys. Due to my newly handsome budget, the cost of living in Bangkok was never a burden but I started to feel terribly jaded with working so much; so I finally decided to do something about it.

I went back to basics and read ‘The 4-Hour Work Week’ and implemented some of the advice from there. I then started employing and outsourcing my work, hiring a lady from Manchester to as a sales role.

This was undoubtedly one of my greatest decisions and from this moment my life became nothing short of a dream – I was making a fully passive income. Meaning I was getting paid 6 figures annually (20-30,000 USD a month and my personal best was 42!) even if I spent the week scratching my balls watching The Sopranos.

I instantly upgraded my life to dizzy heights.

A man swims alongside a giant whale shark in Cebu, Philippines.
Swimming with whale sharks in Oslob, Philippines.
Cuscus papua new guinea
Holding a “Cuscus,” while staying with a tribe while backpacking Papua New Guinea.

As fun as that sounds – I actually started travelling to destinations way beyond my wildest dreams. I discovered the differences between Samoa and American Samoa. I even paid for private charter planes to take me to untouched islands within the country.

A beautiful sinkhole with a ladder leading to it in Samoa
The beautiful To Sua Ocean Trench in Samoa.

I stayed with a tribe in the jungles of Papua New Guinea – holding animals I didn’t even know existed. I schmoozed in the swankiest of hotels and rampaged through my Hong Kong bucket list for my 30th birthday – celebrating it by doing the world’s biggest bungee jump, Macau Tower. I got to tick Okinawa off my life-long bucket list and climbed Mount Fuji.

I’ve also been longing to own a quality and durable men’s wedding band, so I hopped on to tungstenrings.com and ordered a few tungsten men’s rings of different types and designs. The rings are so durable that I no longer have the fear of my ring scratching whenever I’m hiking, swimming, snorkelling, jumping off cliffs, or doing any rigorous exercise or activity during my travels. 

Each of those rings with different textures and patterns tells a story that reflects different sides of me. One tells a story about me being a driven entrepreneur, one about me being a loyal friend, and one about me being the dreamer who dared to leap. The rings were a reminder that the hustle had paid off.

I swam with whale sharks in the Philippines. I went to the World Cup in Brazil and partied in Lapa with one of my best mates from back home. I even fixed my ugly British teeth!

Tourists and locals at The Football World Cup in Brazil
Partying during the Football World Cup in Brazil with my best mate from back home.

These are only a few examples of the things I did and the most insane thing about it was that for the first year and a half – I would actually have more money in the bank at the end of the week after doing these things! I was experiencing the ultimate freedom – lots of money and time.

But even the once-mighty Roman Empire fell, right?

The industry started to weaken and my income became progressively lower every month – but I didn’t hold back like I should have done. I kept on living, employing and spending as frivolously as it gets.

The First of Many Bad Lifestyle & Financial Decisions

The crunch time came when I went to see about buying an apartment in one of the best neighbourhoods in Bangkok for expats – in cash for $60,000 USD. I had just about that much in the bank and I was strongly considering buying it. I love Thailand, Bangkok is crazy and fun but it’s not sustainable for someone with my Type A personality.

I loved Chiang Mai since the first second I landed there, but I clearly wasn’t ready to put my money where my mouth was.

I agonised for a week about this purchase. I thought about how amazing it would be – to fully own a mortgage-free apartment in the capital of a country that I adore at the tender age of 30! But for some reason, I decided not to buy it. I was due to visit home for the first time in three years since leaving my hometown and I didn’t want to make a brash decision when I had so much to think about.

If you think that I’m going to be all ‘no regrets’ about this then you’re very much mistaken. It was idiotic of me to not tie in this money and have a place to call my own. It kills me that I didn’t do this.

I made a lot of rookie mistakes during this financially handsome period of my life; I gave away money to people in my life when I wasn’t even safe myself. I continued to employ people when I should have just gone back to basics and work myself. I lost a lot on online business scams (ugh, stop believing hacks) and I never ever cared about the price of something that I paid for – I only cared about the value of the experience.

Pure hedonism in motion.

Tokyo vs Kyoto
I stayed with these beautiful people in Tokyo, free of charge after chatting on the plane to Okinawa. 🙂

I’m a gambler when it comes to business and the last time I gambled – it paid off tenfold. In the last half-year, I have spent around $25K on a project which is yet to bear any fruit. Maybe it will turn into another cash cow, or maybe it will die a painful death – that’s business. There are no certainties in this game.

Edit: This business plan failed miserably and I got into even more debt before dropping my ego and I cut it loose!

Nowadays, there are a lot of ways when you can earn money online, you may check online jobs abroad on Jooble while having a side gig for your future empire.

Right now I’m back in 100% project mode. I am currently doing the Mexico City Digital Nomad thing after leaving Santa Marta and although I’m working a lot – I remember my health this time around. I make an hour a day available to go for a long run and I am eating very healthily (when I was a workaholic in Thailand I would forget to eat quite often).

An important sidenote: I eluded to this utterly embarrassing confession in my things to do in La Paz Bolivia post; I struggled with a cocaine addiction while living in Colombia.

What a cliché; a working-class lad from the UK with a history of behavioural problems turns to blow after making lots of money. Considering my Instagram tagline is; ‘Former Loser Who Took a Risk,’ (a slogan that I am proud of) I have been furious with myself for allowing the dark side to drag me down when I have worked so hard to get out of the mire.

That is behind me now and I have to forgive myself as I can self-hate to an unprecedented level and I need to get back on course.

I could have omitted this sleazy fact about my chapter about losing a 6-figure online business that I built from scratch, but I want anyone out there who is suffering because of stupid mistakes to know that you are not alone, and you don’t have to throw in the towel or beat the shit out of yourself.

I’m juggling a lot of balls about business right now and I’m very much focused on maintaining this life, which I love. I can’t say that I totally regret my lavish life for the last three years which enabled me to visit almost 50 countries (I don’t think there are many better personal experiences to blow your money on than travel), but I do wish that I reigned my spending back a bit – and I do wish that I had bought that apartment in Bangkok.

I said to my housemate the other day that I am ‘transfinancial.’ I always felt like a rich person born in a broke person’s body.

I have made a lot of money from square one before and I will do it again.

Man stands on top of Mount Fuji
Feeling on top of the world, but actually only on top of Japan (at the summit of Mount Fuji).

For anyone who thinks that this post is meant to be conceited and ostentatious, or that I’m arrogant about the money that I made – I can assure you that this is not the case.

There were often times when I travelled alone and almost broke down with happy tears because I was so grateful for what I was experiencing before my very eyes. It gave me time to appreciate the sacrifices that my mother and grandmother made in their lives for me so that I could have more opportunities in mine.

Many days I wished that I could have called my Nana and told her how I’d turned my life around.

I also spent a lot of this time building beautiful friendships, maintaining those that I have already and I started to explore my connection and relationship with food – I’m healthier and happier now after going down this path. I have greater respect for money now and if I find myself in the same situation as before; I’m pretty sure I’ll go about things differently.

Back To The Old Drawing Board: Six-Figure Online Business Again?

I can’t believe that I’ve seen the things I’ve seen and done the things that I have done. I’m just a lad from Durham who had a dream and luckily that dream came true. I spent so much of my life feeling like a worthless piece of sh*t, and suddenly my life has meaning and purpose. My recent life has been a real-life dream and I don’t intend to stop any time soon.

The party has only just begun (only the next one won’t involve me looking like that Scarface meme).

One thing that I can’t bear is to see people not living up to their potential. It kills me. If you’re not happy where you are in life now, know that you are not powerless. Ditch those personal growth books (or at least cut down, and prioritise action over reading), stop spending your time sharing positive memes and buying inspirational fridge magnets and get busy.

You don’t have to be an expert – you always have to start somewhere. Get active and be relentless in your pursuit – just don’t lose yourself or your health in the process.

The next chapter beckons and I will make a 6-figure online business again! 🙂

2023 edit: I am now generating $5000-8000 a month and I plan to make that even higher to get back in those sweet 6 digits a year land! I still travel but after becoming aware of all the cons of long-term travel I decided to prioritise a more balanced life.

Feel free to sign up for my newsletter on my sidebar; I plan to write more about how I make money online to subscribers.

Song For The Moment: ‘Good Riddance,’ By Greenday

“So take the photographs, and still frames in your mind
Hang it on a shelf in good health and good time
Tattoos and memories and dead skin on trial
For what it’s worth – it was worth all the while
It’s something unpredictable, but in the end is right,
I hope you had the time of your life.”

‘Good Riddance,’ By Greenday

Anthony Middleton

A former loser who took a risk. I now live in Chiang Mai, Thailand after visiting over 100 countries. Stay tuned for the next challenge against that clock!
Ultra runner walking in desert

Hi, I'm Anthony!

In November of 2010, I took on a mammoth challenge against the clock in a quest to upgrade my miserable life. I went out of my comfort zone and turned it all around. Ten years later, I’m completely location independent…

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