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I wonder if he regrets selling those $1.6 million of shares then, considering that they probably at least 100 times more valuable now?

He sells MSFT shares in blocks of 5,000,000 (~$125 million) regularly... including 4 times this month (~$500 million).

I very much doubt he regrets selling those shares.

you seriously think bill gates has any concern about his personal fortune at all now?

Enough so to go from robber baron to philanthropist.