I hate this shit because you are inevitably in the worst possible position in terms of not only power, but information. But ultimately your shares are not wort

I hate this shit because you are inevitably in the worst possible position in terms of not only power, but information. But ultimately your shares are not worthless, so this must be a positive thing, and I keep a small portfolio of worthless company shares on the wall to remind me. 1. Unfortunately yes I have heard of this. It sucks and if they don't allow you to sell to cover you should be able to find a lender - I would start by going to a brokerage and talking to your broker. I would imagine if you purchased a short position (a PUT option to sell the same number of shares you will be owning) then you can convince them with enough documentation and maybe some kind of escrow or custodial account to effect it. 2. Then you need a lawyer and a brokerage. 3. An accountant, lawyer and brokerage. Again, this is the good scenario (shares are not worthless) 4. Since you said it was public, try your brokerage first. There are options for private companies in this space as well. There are definitely lenders who will help you out here. If you just wanted to get the whole thing over with I would find someone willing to lend the money against the shares, again if this is a publicly listed security and you can purchase the PUTs then your brokerage should be able to loan against the shares to pay the taxes, you escrow the shares and they loan the money and then shares go into escrow and you have the PUT options so you can treat those shares as cash with your brokerage.