[mahyarm]

If it's a profitable company that you've been at almost 10 years, that you want to stay at, can't you ask them for a raise, and ask them for help with the stock option problem? They probably would want to work with you if you've been there that long.

[iykwimthrowaway]

Raises have of course been requested and granted. My salary isn't really what's at stake here and any raise I could ask for is dwarfed by the potential value of shares sitting on the table that I simply don't know how to get money out of. What are you imagining I'd ask for when you say "help with the stock option problem?" Ask them to buy me out?

[mahyarm]

Well for example, a very low interest loan secured by the stock from the company to help you buy it out / deal with AMT tax credits being distributed over the years. Or a bonus to help you buy out your long vested stock and the AMT tax difference you will have, etc.

With the bonus, the stock shenanigans that they can perform will be relatively minor as far as additional expenses would go. If they IPO 4 years later and you get a windfall, good. If they liquidate and you get nothing, oh well.

You could also sell the shares to interested people on something like Equidate. Then you don't have to cash in your options until you have an interested buyer. If you get right of first refusal issues, then the company would be buying out your stock directly in that case.

I've never used something like Equidate, so your milage will definitely vary.