Snowbirds US Expats Radio Podcast

Gerry Scott
  • 4.5 (6)
  • PLACES & TRAVEL
  • UPDATED BIWEEKLY

Whether you're a Canadian snowbird spending winters in the USA, or an American looking to move to Canada, the Snowbirds Expats Radio Podcast is loaded with useful information to guide you. Gerry Scott is the host of this podcast, Monday to Friday, Gerry works with Canadian and US clients as a cross border advisor with one of Canada’s largest and most respected wealth management firms.. The Snowbirds Expats Radio Podcast is brought to you by the Snowbirds US Day Tracker and the Canada Physical Presence Tracker apps. The Snowbirds US Day Tracker app helps you track the number of days you’re spending in the USA, which is essential to avoid being classified by the IRS as a US resident for tax purposes. The Canada Physical Presence Tracker is the easiest and most reliable way to track your physical permanent days for the purpose of renewing your permanent residence card (maple card). Simply enter the days into the calculator and track the progress as you get closer and closer to becoming a full time resident of Canada. Both apps offer a wide variety of services that include, USD exchange, tax and legal services, Real Estate, Medical Tourism, and more. Download them today on your iPhone or Android.

  1. Episode 86: What You Don't Know Will Hurt You - Gerry Scott's New Book for Canadian Snowbirds

    4D AGO

    Episode 86: What You Don't Know Will Hurt You - Gerry Scott's New Book for Canadian Snowbirds

    Guest Host: Laura Garfield | Co-Founder, Idea Decanter You’ve been heading south for years and doing everything the same way. So why does it feel like the rules keep changing? This episode is a little different. Gerry’s producer Laura Garfield flips the script and puts Gerry in the hot seat to celebrate the launch of his brand new book: Canadians Heading South for the Winters — What You Don’t Know Will Hurt You. After eight years of fielding the same snowbird questions week after week, Gerry sat down and wrote the guide he’d always wished existed. This episode is the story behind that book — what it covers, why he wrote it, and why he believes no snowbird should be without it. What You’ll Learn Why immigration and tax are two completely separate conversations — and why mixing them up is one of the most common and costly snowbird mistakes What “I’ve always done it this way” actually means at the border — and why it’s no longer a safe assumption How border agents use discretion, and why your travel pattern matters more than your intentions What happens when you’re denied entry — and why you can’t just drive to the next crossing and try again Why the book is designed as a reference guide, not a cover-to-cover read The growing trend of snowbirds selling their U.S. properties — and why it’s a taxable cross-border event most people aren’t prepared for Why Gerry split what started as one book into two — and what the second book, The Great Canadian Return, will cover Where to get your copy: http://snowbirdsheadingsouth.com/ About the Book Canadians Heading South for the Winters — What You Don’t Know Will Hurt You Gerry Scott’s debut book is a practical reference guide covering the 10 most important topics every Canadian snowbird needs to understand before heading south — immigration, tax, healthcare, residency rules, day tracking, border crossings, and more. At 180+ pages, it’s built to sit beside you, not just be read once. Available now at www.snowbirdsheadingsouth.com. Resources Get the book: http://snowbirdsheadingsouth.com/ Track your days: snowbirdsusdaytracker.com

    33 min
  2. Episode 85: What Happens When You Leave Canada for the U.S.?

    APR 22

    Episode 85: What Happens When You Leave Canada for the U.S.?

    What really happens to your money, your investments, and your tax obligations the moment you leave Canada for the United States? Gerry sits down with Kevin Heath of GTA Accounting to walk through what actually happens when Canadians exit Canada and become U.S. tax residents. From departure tax and deemed disposition to TFSA traps and state-level surprises, this is the conversation to have before your move becomes official on paper. • Why departure tax is triggered when you leave Canada and how deemed disposition forces you to report gains even if you have not sold anything• Which assets are included in departure tax calculations and why Canadian real estate and registered accounts are treated differently• How deferring departure tax works and when the CRA may require security before approving it• Why TFSAs lose their tax-free status in the U.S. and how mutual funds and ETFs inside them can create complex and costly reporting requirements• What PFIC rules are and why holding Canadian funds in the U.S. can trigger higher tax rates and steep penalties• How owning a Canadian corporation creates U.S. reporting obligations under Form 5471 and the penalties tied to getting it wrong• Why RRSPs are treated differently at the federal and state level and how states like California and Hawaii can tax growth inside the account• When it makes sense to liquidate investments before moving and start fresh in the U.S. with cash• How timing your move can impact whether your income or withdrawals are taxed in Canada, the U.S., or both• Why more Canadians are choosing to work in the U.S., from lower tax rates to currency advantages and broader career opportunities Resources and Links:GTA Accounting Snowbird US Day Tracker App: Available on the App Store and Google Play Coming Soon: The Snowbirds Expat Radio Book

    21 min
  3. Episode 84: Working in the Sun: What Canadian Digital Nomads Must Know About US Tax Rules

    APR 7

    Episode 84: Working in the Sun: What Canadian Digital Nomads Must Know About US Tax Rules

    Of all the conversations Gerry has about cross-border life, the ones involving Canadians who have quietly become US tax residents without realizing it are among the most urgent.  In this episode, Gerry sits down with Karlene Mulraine of Brij Professional Corporation to walk through what Canadian digital nomads actually need to understand about working in the United States. From the rolling three-year calculation that catches even financially savvy Canadians off guard, to the sticky-state problem that can make double taxation impossible to avoid, to the very real cost of trying to file a cross-border return on your own, this is the conversation to have before your wanderlust makes the decision for you. Why the 183-day rule is not the tax shield most Canadians believe it to be, and how the Substantial Presence Test actually works across three calendar years How Form 8840, the Closer Connection Exception Statement, can protect your Canadian tax status even after you have technically triggered US residency Why Canadian employers are almost never equipped to handle US payroll sourcing, and what that means for the employee working from Palm Springs What happens when you file both a 1040NR and a T1, and why the CRA's foreign tax credit review process is where most DIY cross-border returns fall apart Why New York, California, and Hawaii are sticky states, and why working in any of them may leave you exposed to true double taxation that no treaty can fix How treaty tiebreaker positions under Article 4 of the Canada-US Tax Treaty can be used as a planning tool, not just a last resort What a CRA reassessment looks like in practice when a $30,000 foreign tax credit claim gets reversed, and the interest and penalties that follow Why tracking your days across jurisdictions is the single most foundational habit any cross-border traveler or worker can build What You'll Learn in This EpisodeResources and Links Karlene Mulraine - Brij Professional Corporation: https://brij.tax/ Snowbird US Day Tracker App: Available on the App Store and Google Play Coming Soon: The Snowbirds Expat Radio Book

    21 min
  4. Episode 83: When Snowbirds Fall in Love: Cross-Border Tax Traps Canadians Moving to the U.S.

    MAR 25

    Episode 83: When Snowbirds Fall in Love: Cross-Border Tax Traps Canadians Moving to the U.S.

    What happens to your RRSP, your home, and your retirement savings the moment you follow your heart across the border? Of all the emails Gerry receives, the ones that concern him most come from snowbirds who've fallen in love with an American and are now making a permanent move south with their heart fully invested and their tax plan nowhere near ready. In this episode, Gerry sits down with Calgary-based US tax specialist Peter Blomfield to walk through the most common and costly mistakes Canadians make when transitioning from snowbird to U.S. resident. From departure tax to state-level RRSP exposure, from LLC pitfalls to the principal residence trap, this is the conversation to have before your heart makes the decision for you. What You'll Learn in This Episode Why the IRS's reporting requirements catch most Canadians completely off guard and what the penalties look like when you miss them The difference between immigration residency and tax residency, and why confusing the two can cost you How state tax rules vary dramatically and why Hawaii and California are two states where RRSP holders face a nasty surprise Why crystallizing gains inside your RRSP before you leave Canada may be one of the smartest moves you can make The Canadian principal residence exemption vs. the U.S. version and how a tax-free sale in Canada can become a taxable event the moment you cross the border The LLC warning every Canadian investor or entrepreneur needs to hear before setting up a U.S. business structure Why having a U.S. lawyer set up your investment structure without a cross-border accountant in the room is a recipe for penalties The foreign tax credit and how rental income from a Canadian property gets reported once you're a U.S. resident A real-world scenario: Bruce and Susan, $2M in assets, an RRSP, cash, and a principal residence. What does departure planning actually look like? Resources & LinksPeter Blomfield — Blomfield Tax: blomfieldtax.com Email Peter: peter.blomfield@blomfieldtax.com Coming Soon: The Snowbirds Expat Radio Book

    27 min
  5. Episode 82: Cross-Border Tax Traps for Canadians & Americans

    MAR 10

    Episode 82: Cross-Border Tax Traps for Canadians & Americans

    What happens to your U.S. investment accounts when you move to Canada or vice versa? In this episode, Gerry Scott sits down with returning guest Trent Robinson, a cross-border tax specialist at Buckberger & Partners in Saskatoon, to unpack the most common and costly mistakes people make when holding non-registered investment accounts across borders. From wrong tax slips to CRA audits arriving five years late, Trent breaks it all down in plain language. What You’ll Learn Why holding a U.S. non-registered account as a Canadian resident can trigger serious tax complications The key difference between a U.S. “qualified dividend” and a Canadian “eligible dividend” — and why mixing them up is costly What happens when your U.S. financial institution doesn’t know you’ve moved to Canada The difference between a 1099 and a 1042-S tax slip — and why getting the wrong one creates a mess How CRA and the IRS share information — and why the delay can make things worse The $2,500/year penalty for failing to disclose foreign investments over $100,000 Why some people don’t realize they’re U.S. citizens — and what that means for their tax obligations How much planning you should do before leaving the U.S. to return to Canada About the Guest Trent Robinson is a partner at Buckberger & Partners, a full-service accounting firm based in Saskatoon, Saskatchewan. Trent specializes in cross-border tax for individuals and businesses moving between Canada and the United States, including U.S. tax return filing for U.S. citizens living in Canada, property sales, and dual-country compliance. He has been working in this space since 2008. Website: www.bbllp.ca

    20 min
  6. Episode 81: Cross-Border Tax Strategies for Americans in Canada & Canadians Working for U.S. Employers

    FEB 25

    Episode 81: Cross-Border Tax Strategies for Americans in Canada & Canadians Working for U.S. Employers

    Host Gerry Scott sits down with Heather Sanders of Tax Junction, a cross-border personal tax specialist who helps U.S. citizens living in Canada and Canadians working for U.S. employers navigate the complexities of filing in two countries at once. With a practice built around real people in real cross-border situations, not corporations or trusts, Heather brings practical, ground-level insight into the mistakes that happen when employees move countries without thinking through the tax consequences first, and what it actually takes to get it right. Together, Gerry and Heather unpack some of the most misunderstood rules facing cross-border workers, including why "I just work from my home office" is never as simple as it sounds, and why the payroll question matters more than most people realize. In this conversation, they explore: Why the country where you physically work determines where your payroll must be registered, and the liability risk employers face when it isn't The Certificate of Coverage and when Canadians working for U.S. companies can still contribute to CPP How 401(k) contributions are treated in Canada and why aligning them with your RSP room is the key to avoiding a surprise tax bill Why RSP contributions aren't deductible on a U.S. return, and why that usually matters less than people fear The risks of large catch-up RSP contributions for U.S. citizens living in Canada How mid-year payroll switches between W-2 and T-4, especially when RSUs are involved, can create reporting nightmares Why selling U.S. real estate as a Canadian non-resident requires the right people in your corner from the start The foreign tax credit audit that CRA triggers more often than most people expect, and what happens when no one responds Why "my situation is pretty straightforward" is almost never true once a border is involved If you're living in Canada and working for a U.S. employer, considering a cross-border move, or simply trying to understand what compliance actually looks like for internationally mobile workers, this episode offers a frank and practical look at the planning that protects you and the mistakes that are far easier to avoid than to fix.Cross-border tax doesn't have to be overwhelming. Download the Snowbirds DayTracker app today to connect with specialists like Heather and access the tools and resources you need to navigate your international life with confidence.

    24 min
  7. Episode 80: Working for a U.S. Employer While Living in Canada Retirement Plans Taxes and Cross Border Pitfalls

    FEB 11

    Episode 80: Working for a U.S. Employer While Living in Canada Retirement Plans Taxes and Cross Border Pitfalls

    In this episode of the Snowbirds Expat Radio, host Gerry Scott welcomes back cross border tax specialist Sharon Conrod of Hanson Tax LLC for a timely conversation on one of the most misunderstood cross border situations today Canadians living in Canada while working for U.S. employers. As more professionals take U.S. roles while residing north of the border questions around 401k plans IRAs RRSP room and treaty relief are becoming increasingly common and increasingly complex. Sharon explains how U.S. retirement plans are treated in Canada when deductions are available why tracking basis matters and where many people unknowingly create future tax issues. The discussion also explores remote work considerations employer matching crystallization strategies state level tax risks and why there is truly no one size fits all solution when families live and work across borders. What You Will Learn How 401k and IRA contributions are treated when you live in Canada When U.S. retirement contributions may or may not be deductible in Canada Why RRSP room limits matter for cross border commuters The role of Form RC268 and why it is critical for Canadians with U.S. plans How employer matching works and when it still makes sense to participate Why tracking non deductible contributions over time is important How crystallizing RRSPs before moving to the U.S. can reduce future taxes Why certain U.S. states can complicate otherwise treaty protected plans Common mistakes remote workers and employers make Why residency and family dynamics matter in cross border planning Why This Episode MattersCross border work arrangements have grown significantly but the tax rules have not become any simpler. This episode highlights why working with experienced cross border professionals can help prevent costly mistakes both now and in the future.

    40 min
  8. Episode 79: Moving North: Why Canadians and Americans Are Heading Back to Canada

    JAN 27

    Episode 79: Moving North: Why Canadians and Americans Are Heading Back to Canada

    In this episode of the Snowbirds Expat Radio Podcast, host Gerry Scott welcomes back returning guest Aaron Dawes, a cross-border personal tax expert with Smythe. While previous conversations focused on Canadians heading south, this discussion flips the script. With shifting economic, political, and lifestyle factors, more Canadians—and Americans—are now moving north, returning to or relocating to Canada despite weather, cost, and lifestyle tradeoffs. Aaron explains what’s driving this trend and what individuals need to consider before making the move, especially when it comes to cross-border tax exposure. In this conversation, Gerry and Aaron discuss: Why more Canadians are returning home from the U.S. What’s motivating Americans to relocate to Canada How lifestyle, stability, and long-term planning factor into relocation decisions The tax implications of moving between the U.S. and Canada Why cross-border tax planning is critical before you move Common mistakes people make when changing tax residency How working with a specialist can prevent costly surprises With decades of experience handling U.S.–Canada personal tax matters, Aaron offers practical insights for snowbirds, expats, and globally mobile families navigating an increasingly complex cross-border landscape. If you’re considering a move—or a move back—this episode highlights why planning ahead matters more than ever. Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border. Connect with Aaron Dawes

    26 min
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Ratings & Reviews

4.5
out of 5
6 Ratings

About

Whether you're a Canadian snowbird spending winters in the USA, or an American looking to move to Canada, the Snowbirds Expats Radio Podcast is loaded with useful information to guide you. Gerry Scott is the host of this podcast, Monday to Friday, Gerry works with Canadian and US clients as a cross border advisor with one of Canada’s largest and most respected wealth management firms.. The Snowbirds Expats Radio Podcast is brought to you by the Snowbirds US Day Tracker and the Canada Physical Presence Tracker apps. The Snowbirds US Day Tracker app helps you track the number of days you’re spending in the USA, which is essential to avoid being classified by the IRS as a US resident for tax purposes. The Canada Physical Presence Tracker is the easiest and most reliable way to track your physical permanent days for the purpose of renewing your permanent residence card (maple card). Simply enter the days into the calculator and track the progress as you get closer and closer to becoming a full time resident of Canada. Both apps offer a wide variety of services that include, USD exchange, tax and legal services, Real Estate, Medical Tourism, and more. Download them today on your iPhone or Android.

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