Episode 70: Take Your Money and… Come Home? Leaving Canada, Living Abroad, and Coming Back Again

What does it mean to be a snowbird versus an expat? And in today’s uncertain cross-border environment, is Canada becoming the safer destination to return to?

In this episode, Gerry Scott sits down with Alexander Doulis, author of the 1990s bestseller Take Your Money and Run, to revisit his bold ideas about leaving Canada, living abroad, and protecting wealth offshore. Together they explore how those strategies stack up in today’s climate of economic uncertainty, political change, and shifting real estate markets.

Alex explains why he originally left Canada for Ireland and spent 15 years sailing around the world, why many snowbirds are now selling their U.S. properties, and why annuities and offshore trusts continue to play a role in retirement and asset protection. The conversation also touches on private healthcare, cross-border tax strategies such as Roth IRAs, and the enduring popularity of his books My Blue Haven, The Bonds Revenge, Decommissioned, and Tackling the Taxman.

It’s a provocative, entertaining, and sometimes controversial discussion about wealth, residency, and the timeless search for certainty.

Key Takeaways

• The difference between snowbirds and expats—and why that distinction matters for taxes.

• Why uncertainty is the greatest risk for investors and retirees on both sides of the border.

• Real estate pressures leading Canadians to sell U.S. properties and repatriate wealth.

• The case for annuities and offshore trusts as income and asset-protection tools.

• How private healthcare could ease strain on Canada’s system.

• Cross-border opportunities with U.S. Roth IRAs.

• Why, despite global options, Canada still offers some of the best places to live.

Resources Mentioned

• Take Your Money and Run by Alexander Christ Doulis

• My Blue Haven

• The Bonds Revenge

• Decommissioned

• Tackling the Taxman