Cross-section topics

tax planning

Everything we've published on tax planning 3 articles.

What to know

  • Stripe Atlas offers a low-cost ($500) entry into the US market, but doesn't solve Canadian tax residency issues.
  • Delaware C-Corps are preferred by US investors but can lead to double taxation if 'mind and management' remains in Canada.
  • Canadian founders may lose the $1M+ Lifetime Capital Gains Exemption if they incorporate directly in the US instead of using a Canadian HoldCo.
  • Filing an 83(b) election within 30 days is mandatory for founders to avoid IRS tax on unvested equity.
  • A 'Can-Am Flip' (Canadian parent with US subsidiary) is often the optimal structure for scaling while remaining in Canada.
  • Always distinguish the 'Assignment Rate' from 'Gross Taxable Pay' to avoid unexpected income drops.

Questions readers ask

Can a Canadian citizen own a Delaware C-Corp?
Yes, Canadian citizens can own and operate a Delaware C-Corp. However, they must report the foreign corporation to the CRA using Form T1134 and may be subject to FAPI rules if the company earns passive income.
What is the main advantage of Stripe Atlas for Canadians?
The main advantage is speed and access to the US banking and payment ecosystem (like Mercury and Stripe) without needing a US Social Security Number or physical presence.
Do I need a US physical address for a Delaware C-Corp?
You do not need a physical office in Delaware, but you are required to have a Registered Agent in the state to receive legal documents, which Stripe Atlas and other services provide for a small annual fee.
What is the main benefit of using an umbrella company for IR35?
The primary benefit is total tax compliance; the umbrella handles all PAYE and National Insurance deductions, removing the risk of HMRC fines for the contractor.
How does salary sacrifice help contractors under IR35?
It allows contractors to divert gross income into a pension before it is taxed, lowering their overall tax bracket and preserving their Personal Allowance.
Are umbrella company fees tax-deductible?
The umbrella's margin is deducted from the assignment rate before your gross salary is calculated, effectively making it a tax-deductible business cost.
What is the best country for tax-free passive income in 2027?
The UAE remains the leader for absolute tax neutrality, while Cyprus offers the best balance for Europeans with 0% tax on dividends for non-domiciled residents.
How does territorial taxation work for HNWIs?
Territorial taxation ensures you are only taxed on income earned within a specific country's borders, allowing foreign passive income to remain tax-free if managed correctly.

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