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.
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.