Webinar Replay: 2025 Cross-Border Conference: Strategies for U.S. Expansion

Tax Considerations for South-Bound Business Expansion

Jonah Spiegelman | Principal Cross-Border Tax and Estate Planning Lawyer, Polaris Tax

Jonah Spiegelman unpacked the often-overlooked nuances of international taxation for Canadian businesses entering the U.S. market. His session offered clarity on compliance, structuring, and risk management.

Key Takeaways:

  • Know your U.S. presence—selling remotely, establishing a branch, or forming a subsidiary each triggers different obligations.
  • Avoid double taxation through careful planning and U.S.-Canada treaty leverage.
  • Plan for migration and departure taxes when relocating founders or restructuring ownership.

Download Slide Deck (PDF)
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