Jeff Bezos espousing tax myths hurts people's understanding of the rules CRA applies
Jeff Bezos espousing tax myths hurts people's understanding of the rules CRA applies

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I’ve never been to Portugal, but I’ve heard good things: the culture, towns, history, food and wine. My wife and I are planning a trip later this year.
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A common reply to that goal is, “Make sure you do a bit of work while you’re there so you can write the trip off.” I laugh along. But I’m also cataloguing in my head yet another instance of a tax myth so embedded in Canadian conversation that otherwise sensible people repeat it without a second thought.
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The myth is that if you do a sliver of work on an otherwise personal trip, you can deduct it against your business income. But you cannot deduct personal expenditures against business income. An attempt to do so can earn you a reassessment, interest, possible penalties and — if the Canada Revenue Agency (CRA) concludes the line was deliberately crossed — a possible referral to its criminal investigations program.
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I’ve spent decades listening to tax mythology from people at cocktail parties to clients whose brother had a clever idea, but a remarkable new contributor was added this past week: Jeff Bezos, Amazon.com Inc.’s founder. In a recent television interview, the world’s fourth-richest person made two confident claims about tax that, taken together, would not survive a first-year tax course.
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Myth one: “There’s no truth to this buy, borrow, die thing.”
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The strategy is straightforward. You buy an appreciating asset and hold it because selling triggers capital gains tax. You borrow against the asset and live on the loan proceeds because loans are not income. You die, and in the United States, your heirs inherit the asset at fair market value on the date of death — the so-called step-up in basis rule for U.S. tax purposes.
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This strategy is routinely taught in American tax and estate planning circles. Bezos’s rebuttal — “I sell Amazon stock routinely” — is technically true, but misses the point. Yes, he sells some stock and pays tax on those sales, but the vast majority of his appreciation has never been realized, and the unrealized portion held at death gets washed clean by the step-up with no income tax.
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The U.S. does impose an estate tax on death, but the planning industry around minimizing it — through trusts, life insurance, lifetime gifting, charitable structures and valuation strategies — is mature, sophisticated and well within reach for anyone with Bezos’s resources.
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Canada is a different jurisdiction. We have neither a step-up in basis rule nor an estate tax. Instead, we have a deemed disposition at death: the CRA treats a deceased taxpayer as having sold all capital property at fair market value the moment before death, and the accrued gains are taxed on the terminal return. The third step of buy-borrow-die does not exist here.
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Myth two: “The bottom half of earners should pay zero income tax.”