• Corporate Life Insurance and Post-Mortem Pipelines: Optimizing the Sequence

    Corporate Life Insurance and Post-Mortem Pipelines: Optimizing the Sequence

    The Interaction Between Corporate Life Insurance and Post-Mortem Pipelines: Sequence Matters Post-mortem tax planning for Canadian business owners focuses heavily on mitigating double taxation. When a business owner passes away, their estate pays tax on the deemed disposition of their shares. Without proper planning, extracting the underlying corporate assets later can trigger a second layer…

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  • Holdco Investing: Unlocking the S&P 500 Without the Tax Drag

    Holdco Investing: Unlocking the S&P 500 Without the Tax Drag

    Why Warren Buffett’s Best Advice Can Be Inefficient for Canadian Holdcos (And How to Optimize It) In 2007, Warren Buffett made a highly publicized $1 million wager against the active wealth management industry. He bet that a basic, low-cost S&P 500 index fund would outperform a hand-picked portfolio of elite hedge funds over a decade.…

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  • Tax Considerations for Corporate Life Insurance & Estate Planning

    Tax Considerations for Corporate Life Insurance & Estate Planning

    Most corporate life insurance is sold on one headline: “tax-free death benefit.” For private corporation shareholders, that is only step one. The real outcome is net-to-estate—what the estate can actually receive after CDA limits, share-valuation tax, and post-mortem sequencing effects are accounted for. Below are three friction points that warrant serious consideration, as they can…

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  • Rethinking IFAs: What Accountants Should Consider After Bill C‑59

    Rethinking IFAs: What Accountants Should Consider After Bill C‑59

    Print Version The recent GAAR amendments enacted through Bill C-59 mark a turning point for Immediate Financing Arrangements (IFAs). While previously tolerated due to sequencing and legal form, these leveraged insurance strategies could now be exposed to reassessment on the basis of economic substance and purpose. For accountants advising clients with IFAs—or considering one—the deductibility…

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  • The End of an Era? Why GAAR Now Puts Premium Financing on Shaky Ground

    The End of an Era? Why GAAR Now Puts Premium Financing on Shaky Ground

    For years, Immediate Financing Arrangements (IFAs) have been promoted to high-net-worth Canadians as a tax-efficient way to fund permanent life insurance. The model relies on a simple premise: pay a large insurance premium out of pocket, then obtain a loan secured by the policy to “replenish” that capital. Rinse and repeat. The borrowed funds are…

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