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"..why shouldn’t the startup go to an investor, sell their options for what they claim their options to be worth, and then pay me in cash?"

Because an option held by an employee has more value because it functions as an incentive.



The incentive effect is therefore entirely dependent on the employee's degree of ignorance! Experience has shown me that "options are worthless" is a pretty good rule of thumb, and I simply ignore everything but the so-called "base" salary when I evaluate a job offer.




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