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I had traveled extensively throughout Canada, eastern and northern United States, but I’d never seen a palm tree.

Then, in 2006, I took my first trip to Cuba with my wife Jackie. I was a bit nervous going to a developing country – but that soon dissipated as we met the people and felt the warm ocean air. I was hooked on the Caribbean – and finally got to see those palm trees. 

After returning home, I couldn’t get the trip out of my mind. “How could I make money in the Caribbean?” I wondered.

My first idea was coffee. I could put a tiki hut in all the resorts around Cuba and sell Tim Horton’s or Dunkin’ Donuts coffee and cold coffee drinks (Tim Horton’s would be better, of course, because I’m Canadian, eh!)

I began researching the idea every spare minute I had, but it didn’t take long to figure out how crazy this idea was for a few reasons: Firstly, I couldn’t own a business or own property in Cuba. Even if it were possible, it would cost way more money than I had or would ever have.

I knew there had to be something I could do: I just had to figure out what it was. 

Over the next few years we traveled back to Cuba each year. Then, in 2009, we traveled to the Dominican Republic. I considered opening a business there: Unlike Cuba, I could own property and/or a business in the DR. 

Around that time I stumbled onto International Living magazine and its website. I read every article they put out. Through that publication, I was introduced to Great Escape Publishing… and most importantly a program on starting an online business. It was the moment I realized I didn’t need a brick-and-mortar business; I could start an online business and live and work from anywhere in the world with an internet connection and a minimal investment.

I have no real computer experience, but I figured that there are people doing this online thing and doing very well. Why couldn’t I?

After buying the program, I started working on building a website. With no web design experience and very little computer skills, I worked at it off and on for a couple years. 

Then I found Shopify and it put everything into high gear. I knew the niche I wanted was beachwear/swimsuits. 

At this point, I have a website “” I launched in September 2016 and had three sales my first day. 

In the winter of 2016, Jackie took leave from her job and I quit my sales rep job for a corporate company and we traveled around the Caribbean, exploring five countries in six months: The Dominican Republic; Panama; Honduras; Belize; and Mexico). We worked on building our website as we traveled and checked out the trends in swimwear. 

I’ve spent many hours checking suppliers for quality and good delivery times. I put a lot of time into customer service. I do have lots of competition in this market, so having great customer service wins every time.

Here are my tips if you’re looking at this market as a way to make an income overseas…

1. You probably need more than one “store.” These aren’t that hard to set up thanks to Shopify. But since I started with just bathing suits, I’m eight months in and realizing that we could have learned a lot faster if we had multiple stores. The second store took me only a few days to set up. Now that I’ve done one, it was easy the second time.

2. Show great photos of your products.  Since I didn’t want to carry any inventory or take my own photos, I had to figure out how to get these pictures right. Two good options for tailoring suppliers’ pictures can be PhotoShop or Gimp, if you’re willing to learn. But I found an app called Oberlo which has been a huge help. With this app, you can link your website directly to supplier Aliexpress and use its pictures, descriptions, etc. directly on your site.

3. You don’t need to be that internet savvy. I got frustrated at times but eventually I would figure it out. Don’t be afraid to ask questions of people in the industry and to use Google.

And check out Shopify: It was a game changer for me. They make it easy to set up a store and have great customer service that you can call with any problem.

I’m not making enough money yet to live abroad, but I realize it can take 12 to 18 months to get an online business into the $50,000 to $100,000 range. I’m also helping my wife launch another website that she can manage. 

With some good marketing, advertising, customer service, and patience, we’ll be back living on a beach – and surrounded by palm trees – soon. 

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