Comment by xienze

For the general case: Redeem all stock collected as tax for ETF shares that track broad-market indices. ETFs almost always yield dividends. Toss whatever remains into a black box that no one is allowed to look at. When the government needs some revenue, pick something at random and sell it. It can also sell some ETF shares.

The best part is this works for private companies too. If you work at a startup and get options, now you don't have to pay taxes (as cash) for options you exercise which later turn out to be worthless. You can just hand the government some of your shares. Later down the line, the government either shares in your windfall or misses out along with you. Very fair.