Snowbirds US Expats Radio Podcast

When professional athletes sign big contracts or executives relocate across borders, the tax implications can be as complex as the game itself. In this episode, Gerry Scott talks with David Silber, Partner at Crowe Soberman LLP, about how athletes and high-income earners structure their finances when moving between Canada and the United States.

David leads the firm’s Sports and Entertainment Division, advising athletes in hockey, ba...

Can your U.S. vacation home qualify as your principal residence in Canada?

Buying, selling, or co-owning a home across the U.S.–Canada border can create a web of unexpected tax implications — especially when both countries have their own rules about what qualifies as a principal residence.

In this episode, Gerry Scott sits down with Karlene Mulraine, a cross-border tax specialist and founder of Brij Professional Corporation, to unpac...

What happens when an American moves to Canada?

Dual filing is one of the most complex (and misunderstood) parts of cross-border life. To help unpack it, this episode of Snowbirds Expat Radio welcomes Robin Veenendaal, an independent CPA and member of SME, a professional network that connects and empowers accountants and lawyers across North America.

With nearly two decades of experience supporting cross-border taxpayers, Robin explai...

Should an American living in Canada hold a TFSA—or avoid it? Ask 10 accountants and you might get 15 different answers. That’s why this episode of Snowbirds Expat Radio brings in cross-border tax expert Christa Walkden from 49th Parallel Tax.

With nearly 30 years of experience in U.S. and Canadian taxation, Christa breaks down the complexities around Tax-Free Savings Accounts (TFSAs) for U.S. citizens in Canada. She explains the spe...

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 cl...

What does it really take for a Canadian to live full-time in the United States? 

Can citizenship be passed down through a parent or even a grandparent? And what happens to your taxes if you suddenly discover you’ve been a U.S. citizen all along?

In this episode, Gerry Scott welcomes back Robert Clegg, cross-border immigration and tax lawyer, to unravel the rules around U.S. citizenship and residency. Robert explains how derivative ci...

We’re revisiting one of our most popular and practical episodes on Snowbirds Expat Radio—and if you’re a Canadian with ties to both CPP and U.S. Social Security, this one’s for you.

Host Gerry Scott sits down with Sharon Conrod, CPA of Hanson Cross-Border Tax Professional Corporation, to break down the Windfall Elimination Provision (WEP)—what it is, why it exists, and how recent changes may affect Canadians planning for (or already...

Thinking of giving up your U.S. citizenship? You're not alone—and it's not as simple as it sounds. In this in-depth and timely conversation, Robert Clegg, Cross-Border Tax & Immigration Specialist from Clegg Law Group returns to the Snowbirds Expat Radio podcast to break down the emotional, financial, and legal factors behind renunciation, especially for Canadians who’ve lived in the U.S. or Americans now living abroad.

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Can living abroad come with unexpected tax consequences? Absolutely—and we’re bringing back one of our most informative conversations to prove it.

In this replay episode of Snowbirds Expat Radio, host Gerry Scott sits down with Mike Wallace from Greenback Tax to unpack the complexities of U.S. expat taxes. Whether you're a seasoned snowbird, a new digital nomad, or simply living abroad part-time, this episode is a must-listen.

Mi...

Are Canadian Snowbirds at risk of breaking U.S. law? With new enforcement of a decades-old rule, Canadians staying more than 30 days in the U.S. are now being told to “register”—but what does that really mean?

In this episode of the Snowbirds Expat Radio Podcast, Gerry Scott welcomes immigration lawyer Julia Herzog, of Herzog Legal, who breaks down the recent U.S. executive order and Canada’s updated travel advisory. They explore wh...

What happens if you're a Canadian and get into a car accident in the U.S.? This episode is a must-listen for snowbirds, part-time residents, and anyone who drives across the border. Gerry Scott is joined again by personal injury lawyer Andrew Iacobelli, whose cross-border legal expertise helps Canadians navigate the often-confusing world of U.S. auto accidents, insurance claims, and litigation.

From the importance of underinsure...

If you’re a U.S. citizen living in Canada—or a Canadian with U.S. ties—are you clear on your tax obligations? The answer could be more complicated than you think.

Gerry Scott sits down with cross-border tax attorney Alexey Manasuev from U.S. Tax IQ, to unpack what you really need to know about U.S. and Canadian tax obligations. From foreign retirement accounts to FBAR requirements and residency status, this conversation is packed wi...

What really happens when a Canadian sells property in the U.S.—and how do you avoid unexpected tax surprises?

In this episode of Snowbirds Expat Radio, host Gerry Scott welcomes cross-border tax professional Steven Flynn to discuss the growing trend of Canadians selling real estate in the U.S., particularly in sunny destinations like Florida and Arizona.

They break down the key tax implications, from federal withholding rules to stat...

How do rising tariffs between the U.S. and Canada really impact your wallet—and your winter lifestyle?

In this episode, host Gerry Scott welcomes international trade and tax professional, Dan Kiselbach of Miller Thomson to break down what snowbirds and Canadian retirees need to know about the shifting trade landscape. From the price of beer to cross-border legal protections, this conversation unpacks the real-life implications of ta...

How does the Windfall Elimination Provision affect Canadians collecting both CPP and U.S. Social Security—and what’s changing?

In this episode of Snowbirds Expat Radio, host Gerry Scott is joined by guest Sharon Conrod, CPA of Hanson Cross-border Tax Professional Corporation for an in-depth conversation about the Windfall Elimination Provision (WEP) and its implications for cross-border retirees. Together, they explore the history o...

In this episode, host Gerry Scott is joined once again by Aaron Dawes, a cross-border tax specialist with Smythe LLP, for Part 2 of their discussion on estate planning across the U.S.-Canada border.

This conversation dives into the complexities that arise when Canadian children inherit assets from American parents—a growing issue in cross-border wealth management. Aaron breaks down the tax implications, planning considerations, and ...

Ever wondered what really happens when a U.S. citizen inherits assets from their Canadian parents?

Spoiler: it's not as simple as you’d think.

In today’s episode, host Gerry Scott sits down with Aaron Dawes, cross-border tax expert from Smythe LLP, to unpack the increasingly common—but often misunderstood—scenario of U.S. individuals inheriting Canadian assets. With more families living cross-border lifestyles and adult children ...

What happens to your estate and taxes if you’re a Canadian living in the U.S.? 🤔 Many people assume their Canadian will and financial plans will carry over—but cross-border estate and tax laws are far more complicated than they seem.

In this episode, Gerry Scott sits down with Carol Sadler, a cross-border tax professional from Achen Henderson, to break down the biggest financial, legal, and tax mistakes Canadians make when moving t...