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this post was submitted on 10 Jul 2024
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They're not in Canada, I'm pretty sure. Which is messed up.
Is there something I can read on leveraging stocks as a loophole? I've never heard of it. Every financial advisor will tell you to avoid long-term debt if at all possible.
Here's something talking about the loophole: https://equitablegrowth.org/closing-the-billionaire-borrowing-loophole-would-strengthen-the-progressivity-of-the-u-s-tax-code/
And some talking about some ways in which it can be leveraged: https://www.healio.com/news/hematology-oncology/20220928/avoid-capital-gains-taxes-like-a-billionaire-using-buy-borrow-die-strategy
In short, by borrowing, the tax code assumes that long term the proceeds of the loan will be disposed of in an appropriate tax way. However there are so many ways to be slippery about repayment that it's hardly a guarantee. So it may be wise to shift to pessimistically assuming long term shenanigans at borrowing time and taxing the proceeds as income, with tax breaks around "sane" repayment to handle the intended "avoid double taxation" behavior.
Fascinating. Old paintings as a way of hiding wealth make sense - that is subjective value - but you can look up stock prices in near-real time. Uncle Sam just has a really weird way of defining a transaction, probably do to something in deep US history.
If we're rearranging the whole tax code in this hypothetical, I'd just write it in such a way the IRS is allowed to tax gains even if there's no "realization", or at least taxes heirs just like the deceased. If not, I guess it's a matter of what you can get legislative support for, and what the article suggests would be a reasonable kludge.
Problem with taxing unrealized gains is that there's a fair argument that unrealized gains are, largely, fictitious. For example if Musk said, today, "I am selling all my stock, give me 250 billion now", he would not get 250 billion dollars, because there isn't 250 billion dollars of money actually primed to buy Musk's stock.
Analagous, if your house went up by $150k, then they said "oh, you 'earned' $150k, you owe $80k", your only way to cover that would be to sell the house, which isn't fair because you were living in it, not using it as a financial instrument. However, if you borrowed $150k and used it to buy a couple of corvettes based on that equity increase, well that's weird but maybe ok depending on how you ultimately pay back that $150k you borrowed, but at least in the short term, you made $150k appear out of thin air, which might be janked in the long term...
Yeah, there'd need to be a bit more flexibility about payment schedules, I think. If your stuff appreciates you're definitely richer, it's not just theoretical before selling in today's complex financialised market. It would have to be legal to owe more than you pay for a long period if there's a good reason like "my house isn't subdividable and I am house poor". Taxing something hard to value would be a stickier wicket, but you could just leave the amount owed for your now legendary sports card undefined until it is defined (realised, basically, but without needing to pin it down in the legislation).
And capital gains tax should have to be settled up before your estate closes.
Primary residences are often exempted from financial requirements for that reason.