The Key To A Secure Retirement

According to recent findings from the National Institute on Retirement Security, 68% of Americans aren’t sure they’ll ever be able to retire.

Meanwhile 79% of Americans polled for Intuit’s Prosperity Index for 2025 say the country is facing a retirement crisis.

Self-help guru Tony Robbins has warned U.S. retirees that relying on Social Security in retirement is “a recipe for disaster” and over on yahoo!finance “Rich Dad, Poor Dad” author Robert Kiyosaki’s case for choosing real estate trumping a 401k (appreciation, control, tax advantages…) is laid out.

For a lot of people in the U.S. today, the retirement landscape feels shaky and from a lot of people you’ll hear real estate investment put forward as a solution.

I say, welcome to the party, guys.

Admittedly, 30 years ago when I bought a three-flat building in Chicago, I wasn’t thinking about retirement and didn’t know quite where life was going to take me… but what I did know was numbers.

The property was a good prospect. So, at 27 years of age, with a $5,000 downpayment and a loan to value mortgage for the remaining 98%, I was in the real estate business.

I sold the building less than three years later for a leveraged return of 3,000%, turning my $5,000 down payment into $150,000 in profit after closing costs and commissions.

From there, I turned my attention overseas, applying the same principles from that first investment time and again.

I study the market… I run the numbers… and if the numbers stack up, I buy.

It’s a strategy that made me a millionaire by the age of 35.

Sure, like all investors I took some hits along the way, but for the most part, it’s been a winning strategy.

Three decades on, having bought real estate in 24 countries including rental properties, significant land holdings, and 7 personal residences, it’s fair to say I’m well-versed and well-connected in this world.

I’m also an addict. Hunting for low-hassle, sound investments that provide solid returns is something I’ve never been able to quit. On vacation, I linger at real estate agency windows the same way other people do on restaurant terraces. There’s always connections to be made, deals to be done, and money to be made if you know what to look for…

All that said, it won’t surprise you to know my annual International Property Summit is one of my favorite events in the calendar and this year’s IPS, taking place next week in Panama City, Panama, is shaping up to be a classic. My team of insiders, agents, developers, and experts are flying in from Mexico, Belize, Argentina, the U.K., and beyond.

We’ll have property insights from markets in Panama, Portugal, Greece, Ireland, and more. And we’ll cover everything from structures, taxes, and carrying costs to property perks, pitfalls, and how and where to keep your rental income offshore. Plus, you’ll get the inside track on deals including a $102k hotel opportunity, a brand-name buy in Belize, and a 5-star investment in “The New Aspen”.

If you can’t join us in the room you can still connect online with a Virtual Pass. Get yours here and I’ll talk to you next week.

Stay diversified,

Lief Simon
Editor, Offshore Living Letter