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biznisss t1_jaehlsa wrote

This is all true and insider trading law always feels to me like it's being strung together in real time any time the boundaries are tested.

In practice, many executives of companies with a significant portion of their wealth tied up in stock will not sell as a tax mitigation measure, and instead borrow using their holdings as collateral to service their cash needs, so the question comes up less often than perhaps it otherwise would.

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Slypenslyde t1_jaek9rr wrote

Yeah, the thing I mentioned about "selling in patterns" is based on something I vaguely remember a while back regarding Zuckerberg. He did a big selloff right before Facebook/Meta announced some big embarrassment and people were certain he'd face insider trading, but "this fits a pattern of seasonal sales" was the excuse I saw some people throw around and I never heard anything about it again.

Personally at that level I think it'd be cheaper to hire a US Senator to do the buying/selling for you, they're immune to insider trading and they can count their cut as campaign money.

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