> you will find many people willing to take yours off your hands at pennies on the dollar once that becomes feasible for your company If this were true options

> you will find many people willing to take yours off your hands at pennies on the dollar once that becomes feasible for your company If this were true options would be a lot more valuable. But it turns out by the time a company gets to the point where there is any liquidity for their options, that company has probably passed the inflection point where you are past your 90% mark and it is obvious that it is so. Due to the way option agreements are structured (right of first refusal, exercise time limits, etc) its virtually impossible to sell non-public options for employees who do not wait out a liquidity event (which is another downside to options that companies seem to discount too much).