Tag: Cross-Border Tax

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What Canadian Businesses Get Wrong When Expanding to the U.S. with David Downie (Ep. 33)

What Canadian Businesses Get Wrong When Expanding to the U.S. with David Downie (Ep. 33)

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Expanding into the United States sounds exciting… until the tax rules hit you.

In this episode, Frankie and Sarah sit down with cross-border tax specialist David Downie to unravel the real considerations Canadian business owners face when they decide to move south, scale into new markets, or invest across the border.

What starts as a simple question, “Should I set up a U.S. company?” quickly turns into a maze of entity choices, integration breakdowns, foreign affiliate rules, and unexpected tax traps. David brings clarity to everything from LLC pitfalls to how “mind and management” can trip up Canadian entrepreneurs without them realizing it.

You’ll hear about:

  • When a U.S. subsidiary actually makes sense
  • Why LLCs, while popular in the U.S., are often disastrous for Canadians
  • The surprising “services business” trap that catches companies off guard
  • How cross-border loans between family members can trigger withholding taxes
  • The real meaning of “it depends” in cross-border tax planning
  • And more!

Connect with Frankie Loreto and Sarah Netley: 

Connect with David Downie:

About our Guest: 

David leads Baker Tilly Nova Scotia’s International Tax practice. He is a seasoned cross-border and financial services tax specialist with over 28 years of Canadian and international tax experience, with recognized expertise in cross-border structuring, loan and with repatriation planning. David was a Senior Tax partner at KPMG Canada for 10 years and has also worked at OMERS, one of Canada’s largest pension funds, leading their Enterprise Tax function. 

In addition to serving a broad range of clients with domestic and international issues, David is a frequent lecturer and author with organizations such as the Tax Executive Institute (Canada and the US) and the Canadian Tax Foundation. He was also a Program Designer, Lecturer, and Tutor for the In-Depth Tax Program taught to new Canadian tax professionals for many years. 

David has a Bachelor of Commerce degree from the University of Guelph.

Something of an amateur chef, David also enjoys cycling, skiing, and spending time with his family in Collingwood, Ontario.

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Essential Tax Advice for Canadians with U.S. Ties with Kevin Tippett (Ep. 24)

Essential Tax Advice for Canadians with U.S. Ties with Kevin Tippett (Ep. 24)

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What does spending your winter in the U.S. mean for your taxes?

Join Frankie Loreto and Sarah Netley as they chat with Kevin Tippet about the ins and outs of Canadian snowbirds managing their tax responsibilities when living or owning property in the United States. Whether it’s the intricacies of the 183-day rule, buying vacation homes, renting them out, or selling them, they break down everything you need to know to avoid unexpected tax obligations.

Kevin shares insights on:

  • Navigating the 183-day residency test for Snowbirds [02:01]
  • Tax filing requirements for renting U.S. properties [05:51]
  • Implications of selling a U.S. vacation property [10:00]
  • How gambling wins (and losses) factor in across the border [13:47]
  • Working remotely in Canada for a U.S. employer and tax pitfalls to avoid [18:39]

Resources:

  • Understanding US Tax Obligations for Canadians with Kevin Tippett (Ep. 23)

Connect with Frankie Loreto and Sarah Netley: 

Connect with Kevin Tippett:

About Our Guest: 

A proud Maritimer originally from Moncton, New Brunswick, Kevin graduated from Mount Allison University with a Bachelor of Commerce, majoring in Accounting. In 2009, he earned his U.S. CPA designation and has built over 20 years of experience specializing in personal cross-border tax, with a focus on Canada and the United States.

After relocating from Moncton to Ottawa, Kevin began his career at a Big Four accounting firm, spending eight years developing expertise in cross-border tax matters, particularly advising employees on temporary assignments between Canada and the United States. Named partner in 2025, Kevin assists with the oversight of the cross-border tax practice, specializing in personal, cross-border income tax compliance, and advisory services.

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