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Yes, Bill Gates could sell all his stock at once if he was of a mind to.

That said, he almost certainly would not do that. If he put all his shares on the market at once the price/share of the stock would plummet (for several reasons) and he would lose out on a lot of money.

More likely, if Gates was of a mind to completely cash out, would be he'd initiate a block trade. Essentially he would quietly find an investor (or several) to buy all his shares in one go. Block trades privately like this are permissible away from an exchange when at least 10,000 shares are being sold.

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Q: Could bill gates legally sell all of his stock in Microsoft?
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