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Loophole

§1244 Small Business Stock

Ordinary loss (not capital loss) on failed small biz — up to $100K.

Overview

Qualifying stock in a domestic small corp (≤$1M paid-in capital at issuance) that LOSES money gets ordinary-loss treatment up to $50K single / $100K joint per year — offsetting W-2 income at ordinary rates instead of being capped at $3K/yr as a capital loss.

Best fit
Angel investorsFounder-operatorsSmall biz backers
Estimated impact
Convert $3K/yr cap loss cap into $100K/yr ordinary write-off

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