Welcome to Offshore Living Letter, Your #1 Resource for Offshore Diversification

Author: Lief Simon

23 Sep
Casco Viejo aerial view

The Dangers Buying Leveraged And Pre-Construction Property

Win Huge Or Lose It All—Using Leverage When Investing In Property Overseas At a conference 20 years ago, an elderly gentleman came up to me after I’d presented a real estate investment opportunity to say he didn’t invest in real estate anymore. I figured it was because, at his age, he probably wasn’t buying any [...]
16 Sep
A man filing taxes

The Challenges Of Tax Filing While Being Abroad

Oct. 15 Looms—Here's What You Need To Know To Stay Compliant That is, any American who filed for an extension is now buckling down to prepare his 2018 tax return... myself included. One related topic that has been generating lots of questions for me, both during last week's Retire Overseas Conference in Houston and in my inbox [...]
09 Sep
View of tropical beach in Nicaragua

Our Official List Of The World’s Easiest Residency Programs

5 Best Places To Establish Backup Residency Right Now This is primarily a lifestyle event; the focus is on where and how to live or retire overseas. However, the number of people at this year’s event asking questions about opportunities for backup residencies and second citizenships is significant… many more than at any other Retire [...]
12 Aug
Kuba island in Nicaragua

Why International Real Estate Investing Isn’t For Everybody

Cherif Vs. Lief—Reasons To Avoid An Overseas Real Estate Investment A reader got in touch recently to say: "Lief, I have seen a posting online from Cherif Medawar on international real estate investing. It appears to contradict your group's continued advice on international investments. I'm forwarding it to you for a response because it shows [...]
01 Aug
A big house with a swimming pool

Why My Property Portfolio Is Doubled Down On Diversification

Making Money (And Finding Love) Overseas As longtime readers know, 99% of my investment portfolio is in real estate. Yet my overriding mantra is: Diversification, diversification, diversification. It is the key to success both with your investments and your lifestyle. That's why my real estate portfolio is very diversified. It includes agricultural land, raw land, [...]
29 Jul
Dollar bills and arrow going down

U.S. Dollar’s Bull Run Will End This Month—Here’s How You Can Profit From The Decline

End Of The Dollar's Bull Run? Do you travel to other countries? Canada, the United Kingdom, Portugal, China... Well, I do... a lot. And in recent years I've been enjoying how valuable the U.S. dollar has become against most world currencies. Hotels, restaurants, taxis... it's all become remarkably cheap. The Greenback has been on a [...]
25 Jul
The American flag

How I Found The American Dream Extends Beyond Borders

Lief Simon’s Single Secret To Success I grew up as the only child of a single mother. From a sociologist’s perspective, we probably would have been classified as lower-middle class. That’s using the nine-class category system that my college sociology professor taught—lower, middle, and upper, each having lower, middle, and upper subsets. I remember feeling [...]
18 Jul
Man working out investment returns

Factoring Investment In Colombia: I Was Sold Immediately

A Unique Low-Risk, High-Yield Opportunity In My Favorite Market One of the presenters at our Live and Invest in Colombia Conference taking place in Medellín this week is a colleague in this city who has put together a factoring investment opportunity that has its basis in the struggles this country has faced over the past few decades. [...]