[pslam]

If you cannot find a buyer who will take a cut of a $50MM valuation, then the company is in fact worthless. Liquidity is no barrier to this — there are plenty of financial instruments available to do this transaction, even if you can't actually transfer the asset itself. Taking on debt, for example.

Yes, it sucks, but forgive me if I don't shed a tear for someone who has to find a way to pay taxes on their $50M of assets. They absolutely do have options which aren't terrible.

If a "wealth tax" did pass, then expect countless startups who specialize in handling the arbitrage of this.