This is the immovable object/irresistible force question. Under the constraints of the system, it's impossible for Gates and Buffet to get the current market value of their stock for every share. If they went for fair market value at the time, FMV would trend to 0 as the market was flooded.
For the sake of the argument we can assume some random corporation with cash on hand is willing to buy out their stakes in their respective companies. Heck, we could probably claim Berkshire and Microsoft as corporations would be willing to buy back the stake they own in them. Or run the experiment without full value, if you felt like it. They could still get a huge chunk of it cashed out
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