5 Businesses We’ve Tried & Failed in the Past 3 Years

We were recently featured on The Professional Hobo’s Financial Case Study series, where for the first time we revealed our online income, and we were met with a lot of reactions. Many were very positive, others more in disbelief that it is possible to earn such a substantial income from affiliate websites, and we also received quite a few emails from people with questions wanting to know how they can do it too. In fact, we are often met with that question from people we meet throughout our travels, and even from our own friends and family members. In fact, the most common questions I get in my email inbox are “how do you afford to travel so much?” and “how can I do it too?”. I know all travel bloggers reading this right now are probably nodding their heads.

The truth is, the options to making money online are endless. Go ahead and Google “how to make money online” and you’ll find countless articles and lists from fellow bloggers with ways in which you can make money while traveling the world. The key here is that doesn’t mean all of these are going to work for everyone and you aren’t necessarily going to make gobs of money, especially in the beginning. But if you stay focused, keep educating yourself, learning from your mistakes, tweaking your business model when its not working, and keep pushing through, it will payoff.

I got to thinking recently about what it took for us to get to where we are now. We didn’t just wake up one day and decide to build some websites, throw in some affiliate links and start collecting a paycheck. It started with two people reading other peoples’ travel blogs, wanting to travel the world, and wondering how in the hell they were making money to do it. From there it took A LOT of research. It took A LOT of time. And it took A LOT of money down the drain. It took 5 failed business ventures before we ever started earning a sustainable income.

A Restaurant in Thailand

Working hard or hardly working?

A photo posted by TheTradingTravelers (@tradingtravelers) on


This was alllll Charlie. Yep, I’m going to go ahead and put the blame on him for this one. Many don’t know, but he actually had part ownership in a restaurant in Thailand. He was kind of the “silent partner” and did more of the behind the scenes and web work. But he actually got into this partnership before we ever made the move to Thailand. This was what we always considered our “ticket to Thailand”. It’s what got us there. It was what we needed to finally get the courage to pack up and move our lives across the world. Unfortunately, no money actually came out of that initial investment. It was a lot of money lost and a lot of lessons learned. But guess what? We know we wouldn’t be where we are today had we never made that move to Thailand.

The Trading Travelers – Travel Blog

Like so many other people, we believed that all of these travel bloggers we were following were actually getting paid to travel the world and write articles on their blog. And WE WANTED TO DO IT TOO!! I mean…how cool would that be?! We quickly learned it doesn’t exactly work like that. In fact, very few travel bloggers actually get paid for their writing. Most bloggers make money from their blog through paid advertising, sponsored posts or links, affiliate links and other less glamorous-sounding methods. And it takes a lot of work to make a sustainable income. A lot of hustling. And a lot of website traffic. We realized this wasn’t exactly the picture we had painted in our heads so we never took our blog to that level. We have the blog because its more of a hobby, a way to share our adventures, and allows us to connect with other wanderlusters, digital nomads and you! It does get us some perks every now and then, but we make very little money from it.

Affiliate Websites – Round 1

When we first broke into the world of affiliate websites, we got off to a pretty good start. You may recall if you’ve read our Dumb Enough to Keep Going Success StoryWe started off with just a couple of websites and we were ranking for our keywords in the top 3 spots on Google within just two months. We couldn’t believe that it was actually working and we were already seeing the money come in. Until one day we woke up and one of our websites was completely de-indexed by Google. Essentially, our website was penalized. No traffic = no money. And then a few days later, the same happened to our other website. And then, we were completely blindsided when a few days later our travel blog was penalized as well! Every website we owned was penalized. It was then that we almost gave up on everything and went back to 9 to 5 jobs. Fortunately, we kept going. We learned from our mistakes – and there were A LOT of them – but we picked up, started all over and gave it another go.

Teespring Bandwagon

If you haven’t heard of Teespring, it is essentially a crowd funding for custom t-shirts. You design a shirt, you set your price and goal of how many you need to sell, and then you advertise the hell out of it. If you meet your goal, then it will be fulfilled. So really, your only investment is in the design of the shirt (if you’re not a designer) and advertising. There was one point when we were in Chiang Mai where literally EVERYONE was doing Teespring. So of course we jumped on the bandwagon. And we failed. We tried a few things, put money into a design and advertising on Facebook, but never had an order fulfilled. Fortunately, it wasn’t too costly of an investment and it was kind of fun. But it was also just another distraction taking our focus from what was actually making us money. It seems like there are always these trendy bandwagon schemes popping up, and not to say that they don’t work because I’m sure they do, but its also very easy to let yourself get distracted and keep from following through with one idea.

FBA – Fulfillment by Amazon


Fulfillment by Amazon is where you sell items on Amazon but you store them at Amazon’s warehouse and they handle the packing, shipping and customer service. This is another “trendy” business model and one we really wanted to get involved in. We spent a lot of time educating ourselves about it, taking courses, listening to podcasts, talking to other people in the business and researching products. We spent over a year investing time into this and even ordered some product samples, yet we never pulled the trigger. I think we were just looking for that “perfect” product and nothing ever seemed right. Nonetheless, it was a lot of time and energy invested into a business that never even got off the ground and time is money, right??

So what is the point of all of this? Am I saying not to try any of these business models? ABSOLUTELY NOT! What I am saying is that it took us 3 years and a lot of mistake and failures to get to where we are now, and I expect to have many more in the future. Don’t be discouraged when you hear of other people’s successes because you feel that you should be doing better, or the same thing didn’t work for you. Maybe it just needs tweaking or maybe you just need to give it a little more time. These are all profitable business models. I know this because I know people that are making money in all of the above ways. But don’t spread yourself too thin. Focus on what you’re good at. Don’t let yourself get distracted. Take more courses, invest in the proper tools, and take advantage of the wealth of free information online to keep educating yourself and growing your skills. But most importantly, do something. And don’t give up. Keep pushing through. I promise…ITS WORTH IT.

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  1. Very inspirational, Britt! It can be overwhelming to try to understand all the different online opportunities and how to go about pursuing them! I’m glad you guys have it figured out!

    • Charlie and Brittany July 22, 2016 at 1:19 pm · · Reply

      Thanks Em! It can definitely be overwhelming and its always changing! We are still learning more and more every day.

  2. Awesome! I’m glad your interview on my site sparked some conversation, and ultimately this post. 🙂

  3. Thank you for this nice jolt of motivation. Am currently on a similar path and trying to juggle four relatively unsuccessful ventures, so it’s definitely motivating to read these struggles which ultimately led to a lucrative and successful income stream. Cheers!

    • Charlie and Brittany July 23, 2016 at 1:27 pm · · Reply

      Hey John, thanks for the comment! I’m glad it struck something with you and I understand how these struggles can be discouraging. But just remember that no entrepreneur rises straight to the top! These struggles and obstacles are part of the path…just keep pushing through! Good luck!!

  4. Justin Bennett July 23, 2016 at 4:49 am · · Reply

    The path to success isn’t just straight up. It includes a lot of short falls but you learn, much like y’all did and do better the next time. You both are where you want to be now though!

    • Charlie and Brittany July 23, 2016 at 1:29 pm · · Reply

      Exactly! You live, you learn and you keep pushing through. Giving up won’t get you anywhere. Thanks, Justin!

  5. Great post, you two. We see so much in the blogging world that focuses on the success stories, it’s nice to have a healthy dose of reality sometimes. I’ve come across most of these myself and try to maintain a very realistic approach. Thanks for sharing your experiences!

  6. Great post guys. As Cameron said, its nice to have some reality and honesty. There are so many blogs simply stating “here’s how I made lots of money online” but they never show the losses and mistakes that it took to get them there. Thanks! Love C and D x

  7. The business literature nowadays talks a lot about the need for failure in the pursuit of excellence. Do you accept that?

  8. Yeah, I’ve seen the travel blogs a dime a dozen. I am happy yours is a success or that you are somehow making money whilst traveling.

    I travel the world the hard way: it’s my job. I have worked in the travel industry for many years, and have seen many countries. I a not a travel agent, though. The funny part is, now I just wish I could stay home.

    It’s nice to dream about a vagabond life, just churning out a blog or have some internet gig going so you can just interact with the natives all day, but in reality it’s hard to do, as you point out.

    For those who want to see a bit of the world I might suggest working your way into the travel/hospitality industry. True, you can’t always wake up and follow where your muse leads you, but it will give you a good understanding about moving about the globe and to understand how a global industry works. Believe me, it’s a lot like making sausage. If you knew the truth about the fragility of the whole system you probably would not want to take a trip — ever. But…you do learn how to get around, make contacts and then maybe you can launch a hobo career.

    Good luck to all those out there trying to do this, but an education on how the “system” of travel works can go a long way towards making your dream come true.

  9. Wow! It almost feels like I’m reading a mirror of our own travels and adventures. You guys have set out to do the same things that we tried and have found the same results. (I’m envisioning a really animated conversation in a coffee shop should we all get together some day.) The blogging aspect has been reduced to a hobby. If we get anything out of it, it’s enough to cover the costs of hosting the site and any additional promotions that we run. Basically self sustaining. It’s strange how we carry on with the blogging. We must see some great reward for putting in the effort but I’ve always visualized it as a live journal that we can reference back to if our memories start to get fuzzy.
    You guys win for being most adventurous. I always thought it would be cool to start a restaurant but the daunting task of putting something like that together seems way too over whelming.
    Enjoy the ride and keep the good times rolling,
    Nick

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