Great "engineer-brain" analysis, risk mitigation is just good science. There are always unknown unknowns. Weigh up the potential real cost of an inadequate contingency plan versus the insignificant real cost of diminished return as a % of a bonanza return, so he'll only potentially end up with let's say $40m rather than $44m by selling most of his recently converted options but he's paid taxes and got $150k "wages" right now. This further shores up the company treasury to strengthen its negotiating position.
Btw if someone is buying a company with a big kitty apart having less leverage closing the deal than they would if that Co was broke, wouldn't cash pool be priced into the valuation, in which case despite the immediate downward selling pressure on the SP share holders will ultimately get some benefit
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Great "engineer-brain" analysis, risk mitigation is just good...
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