The year was 2012. Tim Ferriss’ best-selling book, The 4-Hour Workweek, had peaked on the NYT bestseller list for 5 years running. Everyone in my immediate social network and on Twitter was raving about it – this was the path to building a six figure plus ‘passive’ income… focused on outsourcing most, if not all, of the operations of a company to third parties around the world for dirt cheap prices.

The goal? Work from anywhere, anytime, with nothing more than a laptop and internet connection to gain freedom from the 9-5. How? By systematizing your company – having other people complete all the minutiae of the day-to-day operations – you are free to pursue other projects of your choosing. Or not, and just live on a beach in Mexico forever while your machine made money for you.

I, like many others, was shocked that this could even be a possibility let alone reality.

The wild west of internet businesses

Coming from outside the tech sector I hadn’t thought about the ways the internet and smartphones were fundamentally changing the way businesses could be built and scaled. In far less time and with far fewer resources than any other time in history you were able to find a target market, validate that people would buy your product, and find someone who could make (and ship!) the product for you.

And perhaps most importantly, as Ferriss suggested, you didn’t need to hire anyone to help you run the company… finance, customer support, social media management, etc. could all be outsourced to countries like the Philippines for pennies on the dollar where a young woman named “Lisa” would do all the grunt work for you.

The spark - a van full of military dudes

I wanted a piece of the action. At the time I lived in Rio de Janeiro, Brazil and worked for a small Brazilian food company as a manufacturing and quality engineer. My apartment was about a 10-minute walk from the neighborhood of Ipanema as well as the famous Leblon beach. As a 23-year-old single guy I couldn’t fathom ever leaving. And I felt the 4-hour workweek was my ticket to secure a future full of caipirinhas and foot volleyball all day, every day, for the rest of my life.

The only problem was I had no idea what type of internet company I wanted to start. Ferriss suggested e-commerce companies as a great way to get your feet wet but that seemed like too much work. My day job in food manufacturing taught me enough to know I had no interest in making or selling physical products. Any other brilliant ideas I thought I had were instantly shot down by friends.

But just before moving to Brazil I had spent about a month in between jobs hiking across the southeastern United States. A friend of mine was a big backpacker in college and we had a blast touring four states and a portion of the Appalachian trail with just our backpacks and a rough outline of the places we wanted to visit.

We ended up meeting a group of army soldiers during one of the hikes. One of the conversations that left a lasting impression was how many of them had wives and girlfriends they had left behind while deployed. We spent quite a bit of time talking about their deployments - nearly all of them had a family they missed and they mentioned that as being one of the worst parts of being overseas.

As I reflected on my conversations with those soldiers I started wondering if there was a way to help them and their families by building a 4-hour workweek type business. If I could start some kind of gifting service or company that would remind those soldiers just how much their families missed them and cared about them, maybe I could make some money while doing good in the world.

Selling beer belts, boots, and barbecue

That was the catalyst for “AmericanManGifts.com” – an online gift catalog geared towards products for the stereotypical beer drinking, gun loving, U.S. flag waving, bearded and burly American man. The plan was to curate a list of unique, patriotic, useful, and sometimes tacky gifts for American men that could be sent by wives and girlfriends to those they loved. Where I could, I would take a cut of the profits to someone’s business I referred people to from my site. I would also generate advertising revenue.

But the big plan to make money with my site was utilizing affiliate links from Amazon. Many people still don’t know this, but Amazon has an Affiliate Marketing Program that is quick and easy to sign up for. By inserting your own referral link from Amazon into the URL of a product you’re showcasing to people, Amazon will pay you a small commission on the total selling price for that item if the person clicks your link and shops with Amazon. Not only that, but they’ll also pay you a commission on any other product the person buys while shopping on Amazon after clicking your link – even if it wasn’t the product you referred them in the first place.

I bought the domain through GoDaddy for $10/yr. and hosted it on a SquareSpace site themed for endless scrolling for something like $10/month. I researched the basics of PHP, SQL, and JavaScript for any custom coding I wanted to do. I set up Google Analytics and primed the page for SEO through meta tags, backlinking, and social media. And I spent hours and hours scouring the web for products I could feature on my site.

$0.67 had me on top of the world

Within about 2 months I had a front page listing on Google for the term ‘gifts for men’. About three months in I made my revenue – a $0.67 commission from Amazon for a ceramic bladed tomahawk purchased by some guy in Canada.

That first commission e-mail from Amazon for $0.67 felt like winning the lottery! There I was, with nothing more than a laptop, internet, and time… actually making money! I was blown away. I had actually started to achieve the dream that the 4-Hour Workweek had described. It was real, and I was on top of the world.

I poured more energy into the website. Every day when I got home from work I’d find another two or three products to post. My site views steadily started increasing… and so did my commission checks. With just an hour or two a day, I knew roughly how much money I could expect to make based on the type of product I featured. I started optimizing for the time of day I’d post, types of products I’d feature based on current events, and even countries I wanted to target based on the keywords that drove them to my site.

All was going to plan. Until it wasn’t.

As it turns out, details matter

About 6 months after starting the 4-hour journey I woke up on a weekend morning to login and post a few new products. I was unable to access my site. I reset my password and tried again. Still no luck.

Perplexed, I checked my inbox to see if there was any sign as to why I was unable to access my site. Sure enough, the evening before, SquareSpace had sent an email that my site would be shut down in a matter of days and I would be unable to access my account. The email itself didn’t provide enough information for me to understand why, but it had something to do with the Terms and Conditions of using their service to host my website.

I knew they had made a mistake. I wasn’t selling anything illegal. I wasn’t using profane language or racy graphics. I was a genuine guy who ran a niche gifting website, simple as that.

I immediately fired off an email to their support team asking what had happened and when I would be able to log back in to my website. After multiple rounds of emailing back and forth, it was determined there was no way I was going to get my website back and that my only option was to transfer the domain and the data to another host.

I was forced to wake up from my dream

I was crushed. The ‘baby’ I had been working on for almost six months was dead in the water and there was nothing I could do about it. The late nights, the custom code, the hours and hours of scouring of the internet… all for nothing. My 4-hour workweek was no more.

A few months later in a fit of frustration and acceptance I finally decided to read through the Terms and Conditions originally set forth as part of the agreement I made with SquareSpace. There it was, in black and white: “Affiliate Linking is Not Allowed Under Any Circumstances.”

I later tried to transfer the site over to a different host… but the effort was fruitless. It just wasn’t the same. I decided to throw in the towel and wrap up that chapter of my life, thankful for the lessons learned but still upset it had been taken away from me.

Everything comes full circle

As luck would have it, I’m now married to a talented woman who is an e-commerce guru. She’s spent the majority of her professional life building e-commerce teams and her own online businesses. She shares stories about many of the same things I dealt with almost ten years ago - advertising and adwords, SEO optimization, product placement, and even basic coding skills.

Despite my failed attempt at the 4-hour workweek I am amazed at how many of the skills and lessons I learned about building an online business are still relevant. Outsourcing labor to freelancers, boosting your website’s Google ranking, working with Amazon sellers accounts, and consistently making or sourcing quality products are all still key aspects of many internet businesses.

Interestingly, The 4-Hour Workweek continues to see a high level of search volume almost 15 years after its initial launch. The dream of escaping the rat race is alive and well. Would I recommend trying your hand at your own 4-Hour workweek attempt? Yes. Building a business from scratch, even if you fail, is a better learning lesson than any school can teach you. Taking an idea from concept to reality teaches you lessons in marketing, finance, web development, copywriting, and many others… FAST.

And while the promised land of a 4-Hour workweek will likely never come to fruition, you just might learn to appreciate the finer things in life… like the fine print in one of your contracts.