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Depends on the crash and if employees are underwater or not.

In this case Stripe cut their validation by 28% and may give more stock based on that price. Assuming they do, will employees come out ahead when compared to if they had been able to lock in 5yrs of equity up front at whatever the price was when they started?

You can always negotiate for more if your locked equity becomes worth a lot less, it's a stronger position to be in as an employee. The equity is a bet on capturing value of large upside imo, their structure limits that.