Snowbirds US Expats Radio Podcast

Gerry Scott
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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 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
  2. 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
  3. 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
  4. 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
  5. Episode 78: Leaving Canada: What 106,000 Departures Reveal About Tax, Residency & Exit Planning

    JAN 13

    Episode 78: Leaving Canada: What 106,000 Departures Reveal About Tax, Residency & Exit Planning

    What does it really mean to leave Canada — and how do you know when you’ve crossed the line from spending time abroad to officially exiting? Host Gerry Scott sits down with Jennifer Reid CPA, CGA, TEP and Frank Casciaro of RSM, two cross-border tax specialists who advise Canadians navigating complex international lives — from snowbirds and dual citizens to executives, business owners, and globally mobile families. With deep experience in international tax and firsthand insight from working with clients before, during, and after a Canadian exit, Jen and Frank break down why leaving Canada is not just a lifestyle decision — it determines how your assets are taxed, what reporting obligations follow you, and where costly compliance mistakes often happen. Together, Gerry, Jen, and Frank unpack the realities behind some of the most misunderstood rules in Canadian departure planning, including why residency is rarely as simple as counting days or keeping a Canadian mailing address. In this conversation, they explore: Why more than 106,000 Canadians left the country in 2025 — and what’s driving the trend The difference between being a factual resident and a non-resident of Canada Why spending a few months abroad doesn’t automatically mean you’ve exited What departure tax and “deemed disposition” really mean in practice Which assets are subject to departure tax — including worldwide holdings, not just Canadian ones When deferring departure tax may be possible, and why it’s becoming harder to do How the Canada–U.S. tax treaty can help prevent double taxation — and where it falls short Why health care eligibility (including OHIP) is not tied to your tax return The compliance risks of keeping Canadian bank accounts, investments, or a family address after leaving TFSA, RRSP, and withholding tax issues that frequently catch departing Canadians off guard Why planning before you leave is far less expensive than fixing mistakes afterward If you’re living, working, retiring, or investing outside Canada — or considering a permanent move — this episode offers a clear, practical look at what truly defines a Canadian exit and the planning steps that can save you from expensive surprises down the road.

    26 min
  6. Ep. 77 Tax Residency Between Canada and the U.S. : What Really Determines Where You’re Taxed

    12/30/2025

    Ep. 77 Tax Residency Between Canada and the U.S. : What Really Determines Where You’re Taxed

    What does it really mean to be a tax resident — and why do so many people accidentally get it wrong when moving between Canada and the United States? Host Gerry Scott sits down with Nicole Madaisky, a dual-licensed Canadian and U.S. CPA who specializes in complex cross-border lives — from snowbirds and dual citizens to professional athletes and globally mobile families. With deep experience in international tax and firsthand insight from working with clients on both sides of the border, Nicole breaks down why tax residency is not just a formality — it determines who gets to tax you, how much you owe, and where costly mistakes often happen. Together, Gerry and Nicole unpack the realities behind some of the most misunderstood rules in cross-border tax planning, including why residency is rarely as simple as counting days or holding a passport. In this conversation, they explore: Why tax residency — not citizenship — often determines which country can tax your worldwide income How Canada’s primary and secondary residential ties actually work in practice Why the 183-day rule is frequently misunderstood and rarely tells the whole story The common ways Americans and Canadians unintentionally trigger tax residency without realizing it What snowbirds need to understand about time tracking, treaty rules, and U.S. exposure Why buying property in Canada too early can create long-term tax and compliance issues How Canadian mutual funds can become a serious problem for U.S. taxpayers The foreign reporting requirements that carry steep penalties when overlooked Why cross-border planning works best when accountants, advisors, and immigration professionals work as a coordinated team If you’re living, working, retiring, or even just spending extended time between Canada and the U.S., this episode offers a clear, practical look at the rules that matter most — and the planning steps that can save you from expensive surprises down the road. Get In touch with Nicole: https://www.nicolemadaiskycpa.com/ 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.

    32 min
  7. Episode 76: Exploring Maui Off the Beaten Path: A Private E-Mountain Bike Adventure

    12/06/2025

    Episode 76: Exploring Maui Off the Beaten Path: A Private E-Mountain Bike Adventure

    In this episode of Snowbirds US Expats Radio Podcast, Gerry Scott speaks with Donnie Arnoult, an avid cyclist, local business owner, and passionate advocate for Maui’s natural beauty. Donnie is the founder of Maui Cyclery, a well-known bike shop in the town of Pāʻia, and a trusted name in Maui’s cycling community. With decades of experience riding on and off-road across the island, Donnie always dreamed of creating something more immersive — a way to share the untamed beauty of Maui with both visitors and locals in a sustainable, approachable way. That dream became reality with Emountain Bike Tour Maui: a guided e-bike experience that allows riders of all levels to explore hidden trails, soak in stunning ocean and volcano views, and encounter local wildlife — all while treading lightly on the land. Donnie’s deep love for Maui and cycling shines through in every tour. His mission is simple: to connect people with the land through the joy of riding. 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.

    25 min
  8. Episode 75: How prepared are you to move between Canada and the U.S. without running into immigration trouble?

    12/02/2025

    Episode 75: How prepared are you to move between Canada and the U.S. without running into immigration trouble?

    What actually happens when you try to move between Canada and the United States without a solid immigration plan — and why are so many families getting stuck, delayed, or denied? In this episode, Gerry Scott sits down with Evelyn Ackah, Founder of Ackah Business Immigration Law, to unpack why pre-immigration planning has become essential for Snowbirds, cross-border families, and professionals navigating life on both sides of the border. With more than 25 years of experience — and her own personal journey immigrating to Canada — Evelyn brings both expertise and heart to the conversation. She explains how immigration, tax, real estate, and family planning all intersect long before an application is ever filed. Gerry and Evelyn break down: What pre-immigration planning really looks like (and why it saves money, time, and stress) How relocating affects tax residency, investments, real estate, and corporate structure What Canada’s reduced immigration targets mean for workers, families, and retirees The most common mistakes people make when they DIY their immigration using Google or ChatGPT Why border officials are showing increased scrutiny, from secondary screenings to Nexus revocations New U.S. rules requiring registration for anyone staying 30+ days, including teenagers How to navigate life when one spouse is Canadian and the other is American Why parents should register their children for Canadian citizenship early to avoid future complications What options exist when a spousal PR application is refused — and why reapplying properly often wins How business owners and professionals use intercompany transfers to relocate to Canada Real-world stories showing how one old border conversation or missed detail can derail an application Evelyn’s insights make one thing clear: pre-planning isn’t optional anymore — it’s the key to keeping families together, avoiding financial surprises, and crossing borders with confidence. Connect with Evelyn Ackah:👉 Ackah Business Immigration Law https://www.ackahlaw.com/ 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.

    43 min
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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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