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Tax liabilities on (optional) employee secondary stock sales is most certainly not a normal business operation.

If your SOP is handing out options, yes it is. I’d also say GAAP likely requires building a cash reserve to cover such liabilities. I’m not an accountant but I’m pretty sure they have to be ready to cover the difference between the option and strike price until the expiry of the option. One would imagine that is less than tax when the option remains unexercised.

It's not a Stripe liability, so no.

GAAP is a set of accounting standards - it doesn't require taking actions, it's about how to record things if you want to meet those standards. So no, there is no GAAP requirement to build a cash reserve. For what it's worth, Stripe isn't even obliged to follow GAAP for their accounting (it is likely they signed a contract somewhere which calls for a set of financials meeting GAAP to be furnished periodically, but again GAAP doesn't require actions, it stipulates accounting entries).

That is absolutely not how options work; the options entitle you to shares, not cash, so all they have to do is put aside a part of the share pool.

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