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Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by runako on Wednesday March 08, 2023 @09:40PM (#35077753)
In this market, the X% might well need to be so near to 100% as to make the transaction not worth doing.

For ex: Stripe has marked itself down ~50% over the last year. Suppose you think the haircut should be more like the 70% comps like SQ and PYPL have taken, and build that into the X%. Then on top of that loss buffer, you prudently demand an illiquidity premium and a profit margin. That arithmetic doesn't leave much room for the employee to retain any stock.

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