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A drone is a pretty extreme measure. A mistress is a very long term plan with long term ROI if not discovered and comes with the ability to influence decisions. It is far more valuable than being able to murder random people.
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Agreed. The drone comment as an aside just to head-off people saying "Well actually people aren't so physically secure anymore..."

The point I'm trying to make is that people at this level can and often do have absolute physical security but have almost comical[0] lapses in psychological/mental security that lead to the kinds of things that you're describing.

The severity of this issue makes me wonder why it seemingly isn't accounted for appropriately in security threat modelling. You'd think that that the handlers for a dweeb like Huang or Gates would take the appropriate steps to mitigate the threat, if only by adopting harm-reduction principles and getting their CEO an in-house honey pot to proactively fend off external threats.

[0] https://www.youtube.com/watch?v=cP4d74Qk3ac

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I agree, but I wonder what is the threat model for the CEO saying, “shut up, I’m your employer. Let this person through.”

I’m not sure somebody with an infatuation and ultimate authority over you is something a security person can work into the threat model.

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Maybe. Or maybe the point of acquiring outsize money and power to many people is to unshackle their experience of the world, and to impose their philosophy on it. Physical security is one thing; I reckon most aren't signing up to be brainwashed for the good of the company (beyond WUSA or whatever).
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