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He can give the shares away directly. Start a charitable foundation, give the shares to the foundation, and then the foundation can liquidate slowly (over decades if need be) to access capital.

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Wouldn't the effect be basically the same, except the ownership changes? I can't imagine he'd have no involvement in such a foundation.

But the charity doesn’t need to liquidate as quickly as he does if he intends to give it away by the end of his life.

One imagines that the endgame for him is probably some sort of charity to hand off to anyway.

Oh that’s an interesting idea.

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