Moldowan v. The Queen Canadian Cross-Border Tax Planning · 3:59 A landmark 1977 Canadian tax case comes to life, breaking down the chief source of income test and how the courts classify farmers into three distinct categories to determine the deductibility of farming losses.
1 Worldwide Income Reporting Canadian Cross-Border Tax Planning · 3:43 Returning to Canada triggers a major shift in how your income is taxed, as Canadian residents must report earnings from every source around the globe — including both Canadian and foreign investments and corporations.
4 CPP and EI Canadian Cross-Border Tax Planning · 3:14 Dive into the essentials of Canadian payroll obligations, covering how CPP and EI contributions work for both employees and self-employed individuals earning income in Canada.
5 GST/HST Canadian Cross-Border Tax Planning · 2:54 A deep dive into Canada's GST/HST registration requirements, breaking down the $30,000 threshold that triggers mandatory registration and how the rules apply equally to sole proprietors and corporations across various business types.
3 Payroll Obligations Canadian Cross-Border Tax Planning · 3:29 Covering the essential payroll obligations for Canadian business owners who pay themselves a salary through their corporation, this chapter walks listeners through the critical steps of registering with the CRA and setting up a payroll account to stay compliant with tax authorities.
3 The Treaty Problem — "Fiscally Transparent" Entities Canadian Cross-Border Tax Planning · 3:54 Diving into one of cross-border tax planning's trickiest concepts, 3 The Treaty Problem — "Fiscally Transparent" Entities unpacks how Article 4(7) of the Canada-US Tax Treaty determines whether income from entities like LLCs actually qualifies for treaty benefits based on how each country classifies them for tax purposes.
4 Surplus Calculations Canadian Cross-Border Tax Planning · 5:04 Navigating the complex world of surplus calculations for Canadian-controlled foreign corporations, this chapter breaks down the three critical surplus pools—exempt, taxable, and pre-acquisition—that determine how dividends from a C-corp are taxed under CRA rules.
3 Double Taxation Risk — The C-Corp Sandwich Canadian Cross-Border Tax Planning · 2:52 Uncover the hidden tax trap of using a U.S. C-corporation as a Canadian investor, as the C-Corp Sandwich breaks down how corporate profits can be taxed at three separate levels before they ever reach your pocket.
Learning Objectives Canadian Cross-Border Tax Planning · 3:00 A deep dive into the cross-border tax challenges facing Canadian investors, uncovering how dividends flowing from U.S. corporations can trigger three separate layers of taxation before reaching your hands.
2 Business Profits (Article VII) Canadian Cross-Border Tax Planning · 3:51 Dive into Article VII of the Canada-US Tax Treaty and discover how business profits are taxed when companies operate across the border, with a focus on the critical role of permanent establishment in determining where your income gets taxed.
2 Common Intercompany Transactions to Document Canadian Cross-Border Tax Planning · 3:07 Covering two of the most frequently encountered intercompany transactions in cross-border structures, this chapter breaks down how to properly document management fees and software service arrangements flowing between Canadian and US entities.
Learning Objectives Canadian Cross-Border Tax Planning · 4:39 Diving into the foundational goals of cross-border tax planning, listeners will discover how Canadian shareholders owning U.S. corporations can reduce withholding taxes on dividends from 30% down to as low as 5% through strategic use of the Canada-U.S. tax treaty.
5 Form 5472 Interaction Canadian Cross-Border Tax Planning · 2:44 Covering the critical reporting requirements for cross-border transactions between related Canadian and US entities, this chapter walks listeners through Form 5472 and why proper transfer pricing documentation is essential for corporate compliance.
1 Form T1134 — Foreign Affiliate Information Return Canadian Cross-Border Tax Planning · 2:59 Covering the essential T1134 Foreign Affiliate Information Return, this chapter walks Canadian taxpayers through the reporting requirements for foreign affiliates, including how to properly document financial details, income, expenses, and surplus balances to maintain compliance.
Learning Objectives Canadian Cross-Border Tax Planning · 3:55 A foundational overview of cross-border tax planning between Canada and the US, this chapter introduces key concepts like transfer pricing rules, arm's length pricing, and the documentation requirements that govern transactions between related entities under common control.
4 Practical Structuring Considerations Canadian Cross-Border Tax Planning · 4:02 A practical guide to structuring cross-border business entities between Canada and the US, showing you how to establish a clean, defensible arrangement where your Canadian corporation acts as the employer and invoices the American side for services rendered.
4 The 2025 Tax Year — First Full Year Canadian Cross-Border Tax Planning · 3:35 A deep dive into what it means to navigate your first complete year as a Canadian resident, where worldwide income reporting becomes your new reality and every dollar earned—whether in Canada or abroad—counts toward your tax obligations.
2 Key Questions for Your Cross-Border CPA Canadian Cross-Border Tax Planning · 3:02 Navigating cross-border tax obligations starts with knowing the right questions to ask your CPA. Canadian residents with foreign business interests will learn the two critical questions they need answered before filing their T1 return, including how fair market value and deemed acquisition rules apply to their foreign entities.
4 What to Expect After Filing Canadian Cross-Border Tax Planning · 3:21 Demystifying the post-filing process, this chapter walks listeners through what happens after submitting a cross-border tax case to the CRA, including how cases are assigned and reviewed, and what realistic timelines to expect.
2 Revenue-Generating Atlas Corp, Founder Takes No Salary Canadian Cross-Border Tax Planning · 3:19 Dive into the tax realities of a thriving US corporation generating $100K daily, as we explore what happens when a foreign-based founder takes no salary and how corporate tax obligations like Form 1120 and the 21% corporate tax rate come into play.