From Broke Backpacker to Serial Entrepreneur

Reinventing Myself on the Road

The reason why I became The Broke Backpacker may not be what you expect.

Following a life-changing leg injury in the Costa Rican jungle, my aspirations of joining the Royal Marines were dashed and I was left struggling with physical and emotional injuries that refused to budge.

I found myself stuck in a downward spiral of depression, I was drinking too much and going out on the town with the express aim of getting into a fight. I hated my circumstances and I hated my body for letting me down.

My girlfriend left me and, like the loss of all first loves, I took it hard. My leg was swollen, angry and painful. Even today, it has not healed. I kept thinking about killing myself.

After nearly a year of psychological mayhem, I packed my bag, emptied my bank account into my shoe, and hit the road.

I stuck out my thumb, and my journey began. I hitchhiked across Europe and found myself in India. I spent nearly two years living and travelling around India on a budget of $10 a day. During that time, I challenged myself to rebuild my confidence.

Every day, I would make myself talk to one more person than the day before. Slowly but surely, I became more confident, more assertive and more capable. I developed better social skills. I learned to adapt, I learned to problem solve, I changed my outlook on many things.

I slept in train stations, I rode trains for thirty hours at a time in steerage with cows and chickens and masses and masses of people, I survived on fried bananas and bread, I hitchhiked, I Couchsurfed, I frequently would wander into Sikh temples for a free meal, a chat, a place to take a nap (The Sikhs are an amazing people, very hospitable).

I pushed further and further away from my shyness, my awkwardness, my lack of self-belief. I became more capable. I had no money, but I had dreams and I was collecting experiences, skills and confidence.

I fell in love with backpacking because, for me, it represented the opportunity to be truly free and to work on becoming the best version of myself.

I came to terms with the changes in my life, and I discovered my passion was to travel. I made a new life plan…

Getting Out of My Comfort Zone

My plan was pretty simple. I wanted to continue to challenge myself, I wanted to continue to learn new skills, I wanted to continue travelling.

I had a burning desire to see and experience everything. I wanted to climb peaks, conquer jungles, navigate deserts, traverse rivers and truly step into different cultures. I wanted to be a real explorer.

I became more and more fascinated with truly off-the-beaten-path destinations – Nepal, Myanmar, Bhutan, Venezuela, Iran, Pakistan, North Korea, Papua New Guinea, The Congo – these were the places I longed to see.

I expected to die gloriously upon the road. This was something that I held onto for years; I would die doing what I loved, I would die on one of my adventures. I never expected to make it to my thirties.

I know that sounds really weird, but it was really quite liberating, it made me live for the moment and not worry about the future.

Becoming a Master Traveler

I became a master at travelling on a budget of almost nothing. I was often uncomfortable, sleeping rough or standing by the road for hours waiting for a lift but it didn’t matter – the discomfort was nothing compared to the incredible freedom that I was experiencing every day and the opportunities for personal growth that were always waiting for me at the edge of my comfort zone.

I got good at spotting opportunities to make money, I bought scarves and leather satchels in India and brought them back to the UK to sell at festivals. Whenever I did return to the UK, I always packed my bag with as much hippy shit as possible because I knew I could make 1000% selling it on eBay.

I picked up work along the way, I worked one hundred crappy and crazy jobs all around the world; herding goats in the Holy Lands, selling weed in Goa, handing out flyers in Vietnam, renting inflatable tubes in Laos and unloading trucks for ten hours at a time into a walk-in freezer (worst job ever).

I have always had a passion for writing, which is kind of ironic as I am dyslexic (my primary school told my parents I was retarded, it was a different time) and I couldn’t read at all until I was about ten. My handwriting, to this day, is pretty illegible and I still can barely tie my shoelaces (I use velcro, don’t tell anyone).

Whilst in India, I made a point of getting off the beaten track and heading to places where I could find hardly any information in my battered Lonely Planet or the couple of existing travel blogs online.

I was especially fascinated with crumbling fortresses and isolated mountain communities. I started hand-writing notes on how to get to these places, where to stay, what to see, how to travel cheap and handing these out to other intrepid broke backpackers I met upon the road.

Eventually, I started a newsletter and sent my dispatches, journalist style, to about forty people. These were well received and a couple of nice folks encouraged me to take the next step. I entered an online travel writing competition and won $100, I was elated. I used the money to register a domain name and to begin my journey as a travel blogger.

Starting My Travel Blog

I wrote my first blog post on January 30th, 2013. It took me two years to make my first hundred bucks online when an Indian hotel company offered me a payment to be included in a post I had written. Making money from my travel blog?

This was possible? This was news to me… I didn’t know what SEO was, I didn’t own a laptop or a camera, I had never heard of affiliate links, I had below average technical know-how and I couldn’t touch type (I still can’t, I use two fingers rapid-fire, my friend Art says it’s as if I am trying to massacre swarms of ants storming my keyboard, but, I digress).

I had however been making notes and writing stories, mostly for myself, for years and had a large library of content to build on. I had been honing my honest, excitable, style for a while and on the rare occasions when others did read it, it was popular.

Starting a travel blog was a life-changing moment for me, it was my first proper foray into making money online and it changed my life forever.

Once I realised I could make money online, I totally lost interest in picking up work on the road; I wanted to work exclusively for myself – even if I didn’t make much money. I traveled to places where I could stretch that money as far as possible…

Very early on, I could see that the only thing that was really stopping me from making serious money online was myself. I believed that if I was willing to put in the hours, to grind it out, that I could build something truly massive.

The thing was, I was perfectly happy gallivanting around the world and earning enough money from my blog to be able to afford beer! Things changed when I went to Venezuela… this was a country which had hardly any online coverage and was viewed to be extremely dangerous.

I freaking loved backpacking Venezuela, it was raw, wild, and beautiful. I climbed the highest tabletop mountain in the world, Mt Roraima, whilst I was there, stepping into Arthur Conan Doyle’s ‘Lost World’. Venezuela was crazy cheap on account of the insane inflation, it was a change in pace for a broke backpacker as I could afford to not sleep rough! I uploaded this photo whilst I was in Venezuela…

Overnight, it went viral. I suddenly had a small audience of about 10,000 people who actually seemed interested in what I was doing, it was time to up my game…

My Most Ambitious Adventure

I wanted to do something that was totally game-changing. Something that would push me further than I had ever gone before. I had ended up back in England after nearly four years of non-stop travel. Looking at a map on my wall, I chose one of the furthest countries from the UK. I chose Papua New Guinea.

My plan was to travel overland from the UK to PNG without catching a single flight. I aimed to hitchhike most of the way and to build a boat to tackle the ocean from Vietnam to PNG via Indonesia. This was my plan, and I thought nothing would stop me.

But plans on the road have a tendency to change and sometimes life intervenes to put you on another path.

Meeting My Wife (for a While) in Iran

Over several months, I hitched across Europe, up through Turkey (camping in the incredible caves of Cappadocia along the way) and into Iran where everything was to change.

I met Nina, a Persian dentist, and we fell in love – I converted to Islam (I am in no freaking way religious and this has not changed that) and we got a temporary marriage so that the police would leave us alone and we could travel together.

We hitchhiked all over Iran and I then left her to travel onwards to Pakistan. A couple of months later, we reunited in India where I had the brilliant idea of driving a multicoloured rickshaw all over the country. This was by far one of the most exhausting and challenging things I have ever done as the bloody thing could only be push-started, it cut out if you stopped moving, and it had a max speed of thirty five kilometers an hour.

We continued to adventure together in India, Nepal and Pakistan. Eventually, we returned to Iran where we had a much larger, more official Persian wedding – and I got a funky new Persian name.

Meeting Nina totally changed everything. I had a new drive and a new purpose. I had somebody who believed in me, and I strongly felt I owed it to Nina to be successful and to earn enough money so that we were not always camping or stressed about having enough money for visas.

My Motivations Changed

At this point, my travel blog was making about $1000 a month. This had been more than enough money to sustain my own travels but was not enough to keep two people going, especially given Nina’s nationality meant visas are more expensive and harder to get than is either fair or normal.

Nina and I got some amazing travels in before we totally blew through our money, and then it was crunch time. My driving purpose had changed, I no longer expected to die on my travels, I wanted to build an online empire that could sustain a lifestyle of adventures.

I spent the rest of 2016 working on saving up money to expand my business. I wrote up to 50,000 words a week as a freelance copywriter (paid at 2 cents a word) for other, bigger, blogs and I sold advertising on my site. I wasn’t necessarily thrilled to do either, but I needed to save up cash.

Whilst travelling in Pakistan for the second time in 2016, I turned to my audience on Snapchat and asked if folks would be interested in seeing this amazing country with me as their guide.

I tentatively put up a PayPal link to secure deposits and… overnight it sold out. I suddenly have $6000 (12 x $500 deposits) in the bank. I then immediately spent this money on trying to grow The Broke Backpacker, reasoning that I had 6 months before I led my first tour to Pakistan and therefore time to make it back. It was a pretty big risk but…

I had a plan.

Investing in Online Ventures and Facing Bankruptcy

In 2017, I launched several new online ventures to test out different ways to make money online.

I started a backpacking gear company, Active Roots, which basically was a dropshipping venture, this crashed and burned hard during 2020.

I also started an SEO agency with a business partner, this also crashed and burned hard in 2020 but I made about $30k out of it before it did, so I count that one as a success.

I also bought an already successful Amazon niche site, at a cost of nearly $6000, which I planned on flipping for $30,000 once I had made some changes to it… This ALSO crashed and burned hard in 2020, and ended up being a net loss of at least $10k.

Over 2017, I built three more niche sites from the ground up. One crashed and burned in 2020 (Are you sensing a pattern?). Two are still going, and still making a reliable $5000 a month between them, in 2023.

I also wrote my eBook – imparting much of my best tips and tricks for travelling broke – ‘How to Travel the World on $10 a Day‘ – you can grab a free copy by clicking the link.

Throughout 2017, I worked my ass off to learn as much as possible about SEO and how to drive traffic.

I began the process of expanding The Broke Backpacker team. I hired a crew of six writers and two editors to help me improve and expand the content on The Broke Backpacker. The thing is, expanding this rapidly is not without its challenges…

I had invested significantly more money than I had available and had drastically overstretched my means.

Oscar Wilde once said that “A man who lives within his means lacks imagination” and this is a quote that has always stuck with me.

We were extremely close to being bankrupt. I racked up a massive credit card debt, borrowed money from my parents and even from my younger brother – which, I have to say, did not feel good.

But I knew I would find a way to pay it back.

This is very much the abridged version of this chapter in the adventure and it’s impossible to sum up the frankly pretty dark and challenging months I had to push through. Nothing worthwhile is ever easy.

Being this close to bankruptcy was extremely stressful. If I failed, Nina would have to return to Iran since we would not be able to afford her expensive visas. I was passionately in love with her, and I needed to make it work.

In September 2017, I took eleven backpackers on an adventure into the Pakistani Himalayas as the first ever Broke Backpacker Adventure Tour and this gave me the capital I needed to keep building my online businesses.

2018 and 2019

At the end of 2018, I hired an additional staff member to help me with the tour company and foolishly gave them 50% rather than paying them just a wage, I wanted them to feel additionally incentivised through ownership, a concept I was passionate about at the time, but this was a significant error to impart 50% of a venture I had founded by myself and worked on solo for three years. It seemed a good idea at the time, but it wasn’t.

I returned to Pakistan six times, eventually helping my local friends open a small guesthouse in the mountains – it was a highlight of my life.

Two years after leaving the UK on my overland journey to Papua New Guinea, my adventure had turned out very different from what I expected.

Meeting Nina forced me to take a proper look at myself and figure out my priorities. It encouraged me to work my ass off and in the process, I discovered a burning passion for online entrepreneurship.

I fucking love this shit.

This is freedom. It is real and it is there for the taking.

I never had any problem with being The Broke Backpacker, it was an amazing learning curve and a very important part of my life which I will cherish forever. But the time had come to level up.

From a humble 22,000 monthly users in 2016, The Broke Backpacker’s readership grew to an INCREDIBLE high of nearly 1.2 million monthly unique visitors towards the end of 2019.

I felt on top of the freaking world! I was finally making good money and it was time to start the next step in my journey – building, from scratch, the ultimate co-working hostel for aspiring entrepreneurs and digital nomads to begin their online journeys…

In 2019, I co-founded Tribal Hostel with my good friend Mark, a global gallivanter who is, like me, passionate about the power of traveling to change one’s mindset and outlook. After much hunting for the perfect spot, we broke ground on our first co-working hostel in Bali, Indonesia. It was to be a long journey to get the hostel open, but we finally opened our doors in 18/09/2021.

Over 2019, my focus was on growing my tour company, hiring talented new writers for The Broke Backpacker and launching a passion project, a free resource on online entrepreneurship; Ditch Your Desk.

For a long time, I’ve been passionate about sharing tips, tricks and hacks with my audience so they can travel the world on the cheap, have raw and real experiences, and get out of their comfort zones. Over time, my passion shifted as I aimed to teach 1000 people how to ditch their desks, hit the road and create an online income online…

After all, anybody who is brave and willing to push through discomfort, to take risks, can follow in my footsteps. I am but a humble wordsmith, a broke backpacker with no online skills or background, and with no financial backing, and at the end of 2019 it appeared I had built an online empire.

And so, enthused to share what I had learnt, I launched Ditch Your Desk, the ultimate resource for aspiring digital nomads. Here, I focus my passion on teaching others how to ditch their desks, hit the road and live a life of adventure fuelled by an online income.

Little did I know, Covid was just around the freaking corner.

The Highs and Lows of 2020…

Covid hit fucking hard. It completely crushed traffic and revenue.

The Broke Backpacker went from bringing in six figures a month to a five-figure loss just to keep things afloat and my team employed.

During this time, I was funding my side of Tribal from what I expected to make from The Broke Backpacker over the year.

Suddenly, I was in a truly terrifying position and with no idea of when the travel market may bounce back.

Active Roots, my gear company, floundered and then failed as shipping costs rose by 400%. Various other small sites I had started died quickly and dramatically. My SEO agency imploded.

Worst of all, I couldn’t even travel. I felt like everything was going wrong. Luckily, during this time, I rescued a puppy I found on the beach – Chimmigi (Persian for “what are you saying”) – she was to become my best friend and emotional support doggo, moreover she was to bind my fate to beautiful Bali permanently.

As my businesses continued to flounder, I was truly struggling. My funds dwindled, my mood soured, I felt incredibly depressed, I began drinking heavily whilst feeling utterly overwhelmed juggling disaster after disaster. My relationship with Nina broke down and she moved out, we got divorced a few months later. I felt I was alone and at rock bottom, with no idea if things would improve. Traffic was down, my hard-earned savings from the last two years were dwindling, I had no partner, and for the first time in over seven years, I didn’t feel I had a purpose; how could I encourage folks to travel when Covid was making that impossible?

I decided to lose myself in my work and made the decision to double down and go all in, I hired more writers and invested what I had in more content. I focussed on getting sober, sorting out my mental health and building habit stacks to ensure my success in business, fitness and relationships.

I paid for the Pakistan tour company to keep going throughout 2020 on my own, despite having a 50:50 partner. Around this time, the individual I had hired began referring to themselves as the founder of the company.

I figured perhaps the understanding and nuance of the term was unknown to them and I didn’t want to burst the bubble of my friend. I was completely overwhelmed running 9 (seemingly failing) businesses and going through a divorce at the time and ultimately was taken advantage of.

The Hard Lessons of 2021

Struggling with the divorce and the huge pressure of juggling multiple staff members across multiple projects, I made a triggered and emotional decision and parted ways with the Pakistan tour company towards the end of 2021 as I needed to get a toxic relationship out of my life. Giving something away which I had founded solo and worked on for 6 years was, obviously, a huge mistake and lessons were learned.

I had bankrolled the tour company on my own from the start, and kept it financially afloat solo during Covid.

The one condition of my stepping away from that business was that my legacy of work within the company would be respected but unfortunately, it was not, to the point they essentially swapped their name for mine in my original bio copy, claiming they visited Pakistan in 2015 and leaving no trace of the company’s true history.

This was to teach me some of the most important lessons about trust, camaraderie and entrepreneurship and sadly it was to leave a sour taste in my mouth around a country I have so much love for. I will, however, no doubt return to Pakistan in the near future, it holds a very special place in my heart.

If you want to visit Pakistan on a tour, I recommend you check out our post on Pakistan Adventure Tours where I’ve summed up expeditions led by three close friends who I know personally.

Seeing Tribal Thrive

As Bali slowly crept out of Covid lockdown and opened its doors to travelers, we got Tribal open in a limited fashion. It had taken nearly three years to build and there had been many twists and turns. We ran out of money close to the end so we opened just the downstairs area; the restaurant, bar, co-working area and gigantic pool…

The rooms we had to open a couple at a time from June 2022 but we have now been FULLY open for nearly a year. I gotta say, Tribal is doing well. It’s really exciting to see the next generation of aspiring entrepreneurs, go-getting digital nomads and adventurous broke backpackers working hard, forging likeminded connections and having access to the kind of working environment that both myself and Mark had been dreaming of, but struggled to find, on our own adventures around the world.

We are super excited to expand Tribal to other destinations in Bali, and beyond… I really believe there is a big gap in the market for Tribal; there are many travellers now looking to build an online income, or working remote, to find a way to support themselves as they travel the world. This trend is only growing but there is very little in the way of dedicated co-working spaces that also allow you to have access to, and take part in, the backpacker lifestyle.

The thing is, it can be a LONELY journey as one steps out into the uncharted waters of building an online income, of forging their own career path. I struggled to connect with others on my own entrepreneurship journey but on the occasions I did, it was truly an amazing experience to be able to bounce ideas around with likeminded folks who were on similar journeys. Ultimately though, it can be really hard to find your tribe… And that, that is exactly what Tribal is for. The goal is to provide a meeting spot for digital nomads to connect, build a community, to inspire and be inspired, to have access to both the backpacker lifestyle and also to the facilities you need to buckle down and do some good quality work.

Tribal came from the realisation that, personally, I usually had to make a choice when travelling – if I wanted to work, I usually couldn’t stay in backpacker hostels because they were too distracting and they didn’t have the facilities (reliable WiFi, quiet spaces, standing desks, plentiful outlets, individual working booths) I needed to really get quality work done.

Sure, hostels are amazing, the backpacker lifestyle is amazing… but it’s not the best environment to work in. Here at Tribal, we’ve tried to create the perfect middle ground so that you can work, rest AND play.

In 2022, Tribal was finally fully operational and whilst we are still working on expanding and improving the project, we are beyond stoked that it is often fully booked. For aspiring entrepreneurs and digital nomads wanting to build their empires from paradise, in Bali no less, this is the place!

Recently, Tribal won the Hoscar award as the top digital nomad hostel in the world! We are beyond freaking stoked about this and now we are looking at opening a second Tribal, it’ll be bigger, better and even more awesome… so stay tuned 😉

Stay tuned for that and follow Tribal on Instagram to be kept in the loop.

New Horizons in 2023

In early 2023, I took some time out away from work and got back to my roots… traveling to New Zealand, I hired a car and explored, doing two five day hikes (Milford and Abel Tasman), camping, building fires, watching the stars and journalling up a storm.

I thought hard about what I want the legacy of The Broke Backpacker to be, and what my next steps should be… Fourteen years on the road, and ten years working on The Broke Backpacker, it has gone fast! I’ve had a wild ride with epic highs, epic lows, and so many interesting connections along the way.

I am still passionate about the power of broke backpacking for personal development, and the power of online entrepreneurship for building the life of your dreams.

As I sat in New Zealand, upon a rock, my journal in hand, thinking on the wins and losses from the last decade I reflected on that injury I suffered 15 years ago, and the challenges I have endured. These were all great gifts that gave me the opportunity to prove myself to myself. As somebody who has suffered from a lot of self-doubts, I have now learned that optimism is the key to almost every door and that if you work hard, focus on what needs to be done and push yourself, anything is possible.

I have proved to myself that I can travel the world with no money, I have proved to myself that I can conquer pretty much anything that is thrown at me with optimism, positivity and proactiveness.

Next up, I want to leverage my passion for serving the entrepreneurship crowd and to work on expanding Tribal… We plan to build twenty specially designed, custom-built, co-working hostels across the world – Bali, Thailand, Sri Lanka, Pakistan… We’re on the way.

Nine businesses, several failures, more than 40 million visitors to The Broke Backpacker over the last 10 years, lessons upon lesson upon lessons… And this is just the beginning.

Today, The Broke Backpacker is a shining beacon of useful tips, tricks and hacks on how to escape the mundane and travel the world in search of adventure… It’s true that the market changes. It’s possible that this travel blog will go the way of the dinosaurs… AI may change everything, and certainly HOW people are consuming content IS changing with the meteoric rise of Tik Tok and Youtube shorts.

In the background, I am running experiments to try and understand these phenomena and stay ahead of the curve and I’ll share some of these on Ditch Your Desk later in the year. But at my core, I don’t WANT to do social media – I found it terrible for my mental health.

I am a big believer in forging one’s own destiny. It is true that I have slipped and stumbled upon my journey many times. I’ve made mistakes. I’ve had some pretty serious problems with alcohol. My marriage failed and I absolutely lost confidence in myself, my destiny, and my luck along the way.

I have focussed hard over the last two years on my personal development – I passionately believe that once you’ve made enough money to live comfortably, it’s important to look within and to focus on bettering your mind, body and spirit.

In September this year, I am heading to Peru for a twelve-day Ayahuascua retreat with The Temple of the Way of Light. I expect this to be a challenging and rewarding experience. Ultimately, my goal is to continue to grow by stepping out of my comfort zone.

Over the last year, I’ve been exploring within the polyamory community and have learnt a lot about different styles of relationships, this has pushed me out of my comfort zone and fueled a new cycle of growth which I’ve found really exciting.

I’ve realised one can love more than one person, and receive more love in return, it’s pretty beautiful. I have a primary partner, but we both have other people in our lives. In the long run, I dream of running a self-reliant commune somewhere in New Zealand, built on principles of love, growth and sharing. Yep, I’m just a hopeful hippy at heart.

Moving Into the Future

Later in the year, I will be able to move into the house I’ve been building here in Bali. It has a dedicated writing studio where I am excited to finally work on my Sci-Fi and adventure novels. Once in this house, I want to have kids… six to be exact.

It seems like the next stage in my journey is shaping up, I am now 34 but I’m just as passionate about travel and entrepreneurship as ever, both have truly changed my life.

To my regular readers, thank you so much for taking the time to stay up to date with my adventures and your kind words of support. I appreciate the hell out of you 🙂

Whatever your passion, wherever you come from, get out there and crush it, friends. It’s there for the taking…

And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!