If you join a startup and it does well and the valuation increases, there are multiple avenues to monetize shares without liquidating them.

Care to elaborate? Because this is not conventionally possible. Even if it were possible, it’s an awful idea. In year 1 my startup goes from 0 to $10MM in valuation, let’s say wealth tax is 10%. So I (somehow) obtain $1MM in cash, maybe I borrow against it somehow, who knows since you haven’t made it clear how this would work. Anyway, I pay the $1MM in taxes. Now, in year 2, we go out of business, valuation back to $0. Now I’m left with $1MM in debt and I’m financially ruined, but hey, at least I can write off $3,000 from my taxes this year.