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by dublinclontarf 3312 days ago
An alternative is to convert the equity to a debt that must be paid over the next 2 years or something.

Investors won't like this as debt has a higher priority in getting paid than they will.

A settlement agreement whereby the employee (you) gets a severance payment, which may (depending on your tax jurisdiction) be paid in installments over a period of time (years even).

Separate to the settlement agreement you sign over all(most?) your shares, and make it "clear" that the shares being handed over have nothing to do with the settlement agreement (of course they ARE related, but legally they must not be, talk to a lawyer about this).

A severance payment spread over years is much more attractive to investors as it means they take higher priority in the event of liquidation of the company.