01: Common Cross-border Tax Issues / Mobility

Elena and Darren explain common Canada-US cross-border tax and investment issues that may arise when someone has money or family on both sides of the border or moving to live in another country.
In this episode, we introduce many common cross-border issues that may arise when someone has money, family on both sides of the border or changes their tax home.
These are:
  • Tax Residency – how this is defined differently in Canada and the U.S.
  • Tax Reporting – how this may arise unexpectedly when a U.S. person holds certain investments such as PFIC’s and CFC’s
  • How Canadian savings vehicles such as RESP’s, RRSP’s, and TFSA’s may be an issue for U.S. persons
  • The difference between a U.S. Person expatriating from the U.S. vs a Canadian becoming a Non-Resident of Canada
  • The importance of integrating financial, legal, and accounting cross-border services in proper investment and tax planning

02: Cross-border Complexity for Business Owners: The ties that bind you…to the IRS and CRA.


Elena and Darren talk about the many complexities that business owners and their employees face with movement from one side of the Canada / U.S. border to the other.

Full Show Notes

In episode 2, we carry on our discussion around crossborder mobility, this time from the perspective of the owner-manager.

  • Crossborder Employees – Temporary vs. permanent assignees.
  • Tax Residency – Obligations to host country and home country.
  • Retirement Plans – Protecting retirement accounts before making a cross-border move.
  • Shareholder / Business Owner – Complications with crossborder taxation of a corporation and the mismatch between Canada and U.S. tax provisions.
  • Passive Foreign Investment Corporations (PFICs) – Additional filing obligations and making certain timely elections.
  • Trump’s Transition Tax – Canadian businesses with a U.S. owner, beware.
  • Ostrich Syndrome – U.S. citizens living in Canada and ignoring tax obligations.
  • Next Episode – Snowbirds!

03: Crossborder Complexity for Snowbirds: Bring on the sunshine without the double taxation


Elena and Darren talk about the less than sunny side of being a Canadian who spends the winter months south of the border.

Full Show Notes

In episode 3, the cross-border discussion continues with a look at the many U.S. tax considerations for “snowbirds”, including health coverage, tracking days spent in the U.S., buying property, and crossborder banking and investment instructions. Listen to a candid discussion between Elena and Darren on the following topics.

  • The Substantial Presence Test and Closer Connection Exception – When does a snowbird become a U.S. resident for tax purposes?
  • The difference between worldwide taxation vs. worldwide reporting obligations.
  • Structuring U.S. real estate assets to avoid estate tax and double taxation.
  • Financing crossborder property purchases when you can’t get obtain a mortgage in the U.S.
  • The complexities of engaging with your Canadian financial institution(s) to make transactions while on U.S. soil.

04: COVID-19 and the New Economy: Keep planning for the future or embrace the apocalypse?

Elena and Darren discuss the fallout of COVID-19 from an economic and crossborder tax perspective. Tune in to find out how you should approach the current situation in terms of financial mindset and how you can plan for life after quarantine. Topics in episode 4 include:

  • Measures the Canadian and U.S. governments are taking to support families / workers and stimulate the economy during this unprecedented downturn
  • Differences between Canadian and U.S. stimulus packages and tax systems
  • Positive steps to take to mitigate financial hardship (hint: make sure you work with a knowledgeable advisor)
  • Capital losses / gains as a tax planning tool in times of economic uncertainty
  • How behaviourial changes resulting from the pandemic will shape the future economy (online shopping vs. malls, increased telecommuting, etc.)
  • A reminder to stay one hockey stick apart!