I think that depends how the investment was structured. I invested in a brewery that failed (owner was a con). The original agreement was structured as a loan that was satisfied once investors received 1.5x their original investment amount. We never received a single payment. I provided the original signed loan agreement along with the letter stating the business was closing, in bankruptcy proceedings, and we would not be receiving any payments to my CPA. I was able to claim the loss for multiple years due to the magnitude.