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Cannot you receive stock and sell it on the next day?

No, the stock cannot be sold until stripe has an IPO. This is the bind employees are in.

Together they have a 3.5 billion tax bill, but don't have the cash to pay it and cant sell the stock.

It is like if I gave you a magic bean worth 1 billion this year, but the only magic bean buyer will come to town next year (hopefully). how will you pay your taxes.

Not entirely true. There's a grey area where you can sell futures of your own stock on the secondary market that can avoid requiring board approval.

perhaps technically (I'm not very familiar with private futures), but now we have a large number of employees looking for niche buyers to acquire $3.5 billion of stripe futures, which doesn't seem very realistic.

I get why a buyback makes more sense here.

What I don't understand is why they didn't just let the current options expire and issue new ones with a fresh 10 year expiry, an IPO vesting trigger, and no employment contingency.

If you received stripe shares today how would you sell then tomorrow?

Essentially the company is going to intermediate that sale by selling shares to external investors and buying shares from you.

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