[seibelj]

If some random person on the internet wants to help me out. If I exercised my options, and the company was purchased later the same year and my common shares were purchased for $0 (preferred shares took all the money, leaving common with zero), how do I file this loss?

[laxatives]

I'm by no means an expert, but I believe you should ask for a 1099B with proceeds at $0 and cost-basis at either $0 and marked as not reported, or with cost-basis equal to your expense. If the former is the case (not reported), you report the cost-basis yourself.

[seibelj]

Thanks for the info!