I can't upvote this enough. If the IRS is ascribing value X to stock options I can't liquidate, I should be able to pay my tax in the form of those options at

I can't upvote this enough. If the IRS is ascribing value X to stock options I can't liquidate, I should be able to pay my tax in the form of those options at whatever value I am being taxed on them. Of course, the devil's in the details as you probably don't want the government having voting shares in a bunch of private companies either... Maybe they just get a blanket clause to automatically exercise and sell as part of any IPO offering or something? This could have a double-down effect too as the government owns more illiquid stock and feels firsthand the pain of regulations (SarbOx anyone??) that result in fewer IPOs / longer time horizons to liquidity. Oh your revenue is going down because you've regulated companies out of the IPO market? Great, looks like time to get off your ass and actually FIX THE PROBLEM. C'mon guys.