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If I understand the question correctly, and it's about what to do when leaving the company, 83(b) is unnecessary. An 83(b) election says that you are choosing to recognize paper gains today that the IRS would normally require you to recognize when they are no longer subject to a substantial risk of forfeiture. If he's leaving, he must be exercising vested options, so there is no risk of forfeiture, so no need for 83(b).

An 83(b) election is critical for unvested stock, i.e. "early exercise".

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