Moving from Canada to the U.S? Avoid These Costly Tax Mistakes

Moving between Canada and the U.S.? Cross-border tax mistakes could cost you more than you think. In Episode 19 of The Up Side, Eli sits down with Nicole Madaisky, a cross-border CPA specializing in Canadian and U.S. taxation, to unpack the tax complexities of living, working, investing, and doing business across the border. From understanding tax residency and double taxation to navigating TFSAs, Canadian corporations, and tax treaties, Nicole explains why assumptions about cross-border taxes can lead to unexpected tax bills, complicated reporting requirements, and costly penalties. In this episode, we cover: How Canadian and U.S. tax residency rules affect your obligations Common tax mistakes Canadians make when moving abroad Why tax treaties don't automatically eliminate your tax liabilities Tax considerations for U.S. citizens living in Canada How TFSAs and Canadian corporations can create unexpected U.S. tax consequences Cross-border considerations when selling a business Why proactive tax planning matters before making a move When to seek advice from a cross-border tax professional Whether you're a Canadian planning a move to the U.S., an American living in Canada, or a business owner with ties to both countries, this conversation highlights what you should understand before making major financial decisions. *** Connect with Eli & Up Financial: Book a call: https://upfinancial.ca/book/ Email: up@upfinancial.ca Instagram:   / elithemoneyguy   Tik Tok:   / elithemoneyguy    **** Connect with Nicole Madaisky: Instagram:   / nicolethecpa   TikTok:   / nicolethecpa   Subscribe to The Up Side for conversations on building long-term wealth. Disclaimer: This episode is for educational and informational purposes only and does not constitute personalized tax, legal, or financial advice. Consult qualified professionals regarding your individual circumstances. ____ 00:00 Introduction: Cross-Border Tax Planning with Nicole Madaisky 00:45 Nicole's Background in International Tax 03:00 Moving to Dubai: Is It Really Tax-Free? 04:08 Tax Planning for Professional Athletes & Entrepreneurs 07:22 Why Cross-Border Taxes Are So Complicated 09:13 Common Tax Mistakes & Canadian Tax Residency 10:23 TFSA & Canadian Real Estate Tax Mistakes 11:28 U.S. Citizens Living in Canada: Double Taxation 13:24 IRS Reporting Requirements & Penalties 15:30 Salary vs. Dividends for Dual Citizens 18:00 Cross-Border Tax Planning for Canadian Corporations 21:41 Unexpected U.S. Tax Filing Obligations 23:32 Selling a Business: Cross-Border Capital Gains Tax 25:25 When to Hire a Cross-Border Tax Advisor 28:16 PFIC Rules & Foreign Investment Taxation 31:05 Why Tax Treaties Don't Eliminate Every Tax 32:19 The Most Expensive Cross-Border Tax Mistakes 34:15 Why You Should Plan Before Moving Abroad 34:45 How to Work with Nicole Madaisky