There's some interesting exceptions, like how Musk has managed to sell Tesla shares totalling more or less as much as the business itself has made in total lifetime revenue; but even then, Musk's theoretical net worth is very different from how much he could get if he was forced to sell all his shares suddenly.
Owner-CEOs like Musk and Zuckerberg get all the effects of such randomness, but the only examples I can think of such people getting into billion-dollar legal troubles tend to be examples which go on to sink their companies completely, so I'm not sure what impact a fine of "merely" 10% of cash reserves would do to investor confidence as expressed in share price. And this is not the only legal case Meta's facing right now.
MacKenzie Scott (Jeff Bezos' ex wife) show it can be turned into real money. As of December 2025 She had given away $7.1 billion in 2025 charitable donations, and $26.3 billion since 2019.
In reality there is the ability to execute on the shares to turn them into real money.
Jeff Bezos holds less than 10% of Amazon stock himself. Which is a huge amount of money, and a not insignificant amount of which can be turned into "real" money and even with some decline is still a phenomenal amount.
In that same time period the stock valuation has more than doubled.
You have a house? You can sell it next month for a certain price, sell it tomorrow for a bit less.
You own every house in your town? You can still sell a few for “full price” but liquidation of all of them is going to be a shock to the market.