[SirLJ]

The problem is there is no way to prove to the government how much they are worth, because as you said they are illiquid and there is no market... the best is to talk to a tax lawyer, because you can get into a lot of trouble for tax evasion...

[SharesToCharity]

Well as I mentioned the company is currently in the process of closing a 3rd investment round. Therefore investors that are much more sophisticated than me (in both the colloquial and regulatory sense), with access to better information (e.g. up to date financials, whereas I've been out of the loop) have decided that the company is worth $x per share. If the company follows best practices in assigning a 409(a) valuation for my shares based on this sale of preferred shares, that is as far as I can tell the gold standard for valuation. My concerns are simply a lack of faith in the management and product. I'm not sure how this is any different than me saying Disney is overvalued because I think Bob Iger is a bad manager and I didn't enjoy their latest films -- if I chose to offload some Disney stock the IRS will still use the market valuation. Well, the market value of illiquid common stock is the fair 409(a) valuation based on the latest sale of preferred shares.

I will take this to a tax lawyer before proceeding, but I was hoping to find some precedent (for or against) before doing so. Tax lawyers are not cheap, and I'm presently living month to month (paper valuations notwithstanding).