Holdings sold within one year are taxed at your ordinary income rate (up to 37%). Holdings sold after one year qualify for long-term capital gains rates (0%, 15%, or 20%). This distinction matters for insider-signal strategies where holding periods vary based on the trade thesis.
If you sell a security at a loss and repurchase a substantially identical security within 30 days before or after the sale, the IRS disallows the loss deduction. This rule can trip up active traders following insider signals in the same companies.
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