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Failed startup investment (Section 1244 stock)

Varies

Is a Failed Startup Investment (Section 1244 Stock) Tax Deductible?

Short answer: Often better than a normal capital loss: qualifying Section 1244 small business stock losses are ordinary losses up to $50,000 a year ($100,000 joint).

You must be the original buyer, the company must have raised $1 million or less, and it must have mostly operating (not investment) income. Larger losses are capital.

Records to keep: Keep the receipt or invoice and an estimate of business-use percentage.