Could you structure a contract where you buy it for $1 and sell it back the next day for $1?
replyI could be misunderstanding, but this sounds like it would be a wash sale, which would prevent the seller from claiming the loss on their taxes.
replyOh yeah! Get a lawyer. But then that's expensive. Might as well just leave it be and hold the shares.
replyI would simply hold it until the value goes to zero. In the event enterprise value doesn’t go to zero, I would gift any gains back to OP after taxes (because I’m trying to do them a favor, not make an investment).
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