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He does, but the writeoff can't be bigger than what he invested.

Except when it can. It's often possible to do several investments at roughly the same time (within a few years of each other), lose massively on one and write off more than you invested on that one as long as you make a profit on the others and the profit is larger than what you want to write off.

I think it’s that you can negate capital gains with capital losses. Even if, he’s losing money. His tax rate is not 100%.

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