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I've always been curious, what happens if they just let these shares just expire? It wouldn't look great for Stripe, but presumably they would just get back for free (modulo taxes) any shares employees could not afford to exercise. The value of those shares alone could be pretty enticing to the people in charge.

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Good luck hiring or retaining anyone after that while Stripe is still private.

I think the point the previous commentator was trying to make was, why can't they let them expire and issue new options/RSUs of equivalent value to the same people.

My understanding is that the delta between their strike price and the current valuation would be seen as capital gain and taxed accordingly.

Thats a lot of money they don't need to pay that could be used to hire and retain people.

Stripe's compensation is notoriously option heavy, almost like it were a public company https://www.levels.fyi/companies/stripe/salaries/software-en...

I'm guessing this would affect older/first employees the most. These likely have more political weight around the company.

In a pragmatic world, they'd just let them expire.

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