About four years I started a company with three other people. The company (OldCorp) did R&D, got some federal funding but never made a profit so we'd like to sell it. We found a potential acquirer who is interested in buying our company as part of a rollup that they are doing in this space (NewCorp) but we'd only be paid in restricted stock of the new combined venture (likely with a six month holding period).
Personally I don't have any confidence that OldCorp will ever make any money so I am happy to sell it for a price greater than $0. My question is whether there any way this deal could end up being worth less than $0?
October 1st of 2022, the NewCorp acquires all units of my existing company (OldCorp) in exchange for stock in the new company at some price.
Presumably the I owe either income or capital gains tax on the difference between the value of the stock I am receiving and my cost basis in OldCorp at this point.
April 1st of 2023, my holding period expires and I sell my NewCorp stock.
If the value of NewCorp's stock has dropped to less than the value of the taxes I paid last October (or to zero) is there any way to offset that against my previous year's tax liability from when OldCorp was acquired? Or am I just out the money, at least until I've generated enough future capital gains to offset the big capital loss of NewCorp's stock dramatically declining?