Live Anywhere for Free: The Secrets of a Real Estate Investor

The first few years of my life were spent in the tiny frontier town of Gillam in Manitoba, Canada. It’s 600 miles from everywhere, where winters can get as cold as minus 50 F, and your body would become hypothermic and frostbitten if you were caught outside unprepared for even five minutes.

As one TripAdvisor reviewer put it: “If there is a hell in Canada, then Gillam is it.”

You could say that my years there were formative. Born in hell, my mission since has been to spend as much time as possible in paradise.

I spent decades figuring out how to do that. But the secret I discovered turned out to be far simpler than I would ever have imagined.

Today, I live exactly how I desire—in perfect weather all year-round, which for me means no need for air con, no need for heating. I live so close to the ocean that I can watch whales breaching from my terrace and I can fall asleep to the sound of waves crashing on the shore.

And world-class golf is always close by. In fact, where I’m writing to you from in Praia D’El Rey on Portugal’s Silver Coast, I’m just a minutes’ walk from the links. My “local course” has been named the 13th best in Europe, and it’s certainly one of the finest in Portugal, starting out in pine forest before bringing you to the edge of the Atlantic, with views of the Berlenga Islands.

This is a region of Portugal that I love. The beaches are pristine, there’s a treasury of stunning historic towns and fishing villages to explore, I’m spoiled for great seafood… accessible golf… entertainment. And the people are friendly and easy going.

And when I’m not in Portugal, I’m staying at one of my condos in Cabo or the Riviera Maya in Mexico. Or renting a vacation home in Ireland…

My friends and family joke that my life is a permanent vacation. I don’t deny it. I love how and where I live. But when I tell them that it doesn’t cost me a dime, they understandably don’t believe me.

The thing is, my lifestyle isn’t the byproduct of the wealth I’ve built through real estate investing. My lifestyle is the very means by which I’ve built my wealth. And almost anyone can follow the same system, if they choose to.

Here’s the simple truth: My condo in Portugal costs me zilch thanks to the rental income it generates when I’m not using it. Indeed, from the profit I make from 10 weeks of summer rentals (when I don’t want to be there anyway), I literally own my beachfront condo for nothing. The rent more than covers the cost of the mortgage, HOA fees, taxes, my golf club dues, insurance, gas for the car, and even some pocket money.

And I’ve repeated this model elsewhere. Like I say, I don’t do cold. So, each winter I spend some time in another condo of mine in Cabo San Lucas on Mexico’s Pacific Coast.

I bought there in the Copala community in the five-star Quivira Resort as part of a Real Estate Trend Alert deal in 2015. The RETA members-only price at the time was $336,156. Today, these condos are in such high demand that I’m getting emails from brokers asking if I’ll sell. In August 2022 a local broker contacted me to see if I wanted to sell my condo for around $600,000. Then last November, an identical condo two floors above me listed for $725,000.

But I have no intention of selling. I love having the ability to stay in Cabo whenever I want. The laidback seaside vibe… the natural beauty of the desert and mountains meeting the sea in dramatic fashion… the perpetually sunny and warm weather… the golden-sand beaches where I can take long walks in the mornings…

It’s a marine paradise, a beach-lovers dream. I can snorkel, paddleboard, fish, or just sip a virgin piña colada on Medano Beach and watch the whales frolic yards from shore.

I love the golf in Cabo too. It’s world class and a reason why I spend time there in the winter. I relish having golf courses designed by the likes of Jack Nicklaus, Arnold Palmer, Greg Norman, and Tiger Woods close at hand. But it’s also the weather… the perfect weather. Nothing is better for the health—body and soul—than to be bathed in the warmth of the sun. It energizes me.

And besides all that, the rental income my Cabo condo can generate when I’m not using it is way too attractive to give up.

Indeed, before I left Cabo following a stay there earlier this year, I advertised my condo for rent through an agent who suggest I ask $3,500 a month for a long-term let. A couple of days later, I accepted an offer of $3,000 a month. It was lower than I could have gotten, but it was from a very low-maintenance renter who could work around my departure and return dates. I was happy to accept slightly below market for convenience and ease. (If I had wanted to, I could have rented it out short-term for as much as $350 a night—but that would have required more management.)

Just like in Portugal, my Cabo condo is more than a vacation home. It’s a vital component of the life I have built. It’s doing double duty as a place where I can spend time and a place that generates profit for me. And by owning a number of such money-making properties around the world, I can build my wealth while living and spending time in some of the most beautiful places entirely cost free.

It’s a strategy so simple and accessible that I’m shocked that so few people do it, especially in an era when working remotely has become the norm and there are so many residency options available.

The truth is almost anyone can own a profitable home overseas. With the right real estate plays and a lot less money than you might think, you could actually own several… travel between them, rent them for a good income when you’re not there, and when you want to sell, you could lock in a meaty profit. Buy right and your overseas real estate can pay for itself (including the mortgage) just by renting it out for eight to 10 weeks of peak summer season when you probably don’t want to be there anyway.

My criteria is deep value at purchase, strong income potential, perfect weather just before and after high season, proximity to an airport, a nice town or village, and golf. But you’ll have your own personal preferences. Broadly speaking, if you buy a place that strongly appeals to you, there will be a whole market of renters who are interested in the same kind of property and who will happily pay you to stay there when you’re not using it—especially if that coincides with the high tourist season.

But regardless of whether you want a house in the French countryside or a condo by the beach in Mexico, the first step to locking in a strong yield is to seek deep value at purchase. This might mean finding something overlooked and unloved that requires refurbishment work, finding a motivated seller, or striking at moments of crisis. However, in the Era of Scarcity, with desirable real estate in short supply due to rising costs and soaring demand, finding this kind of deep value on income-earning real estate is getting harder.

That’s where members of my Real Estate Trend Alert group have an advantage. Thanks to our group buying power and the value we bring to developers, we can negotiate discounts on best-in-class real estate. That means we can lock in deep value from the get-go, maximizing our yields.

Like I’ve said, this is how I secured my condo in Cabo—which now generates gross yields of nearly 10% renting long-term. I’ve bought in on six more RETA deals in Cabo, along with multiple deals in the Rivera Maya and elsewhere. Some have become places where I’ll spend personal time, others are pure investments that I’ll rent out full-time or sell for strong profits.

I could easily retire and live well off the passive income I’m already generating, but don’t think I will never finish my search for international real estate. I enjoy looking too much. I enjoy having a new part of the world where I can rest my head for free. And, when the moment’s right, I enjoy selling for a profit.