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How do RSUs mostly screw holders compared to options? I don't have a lot of experience with options, but they generally seemed riskier.

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With RSUs, if you are taxed on receiving them in any way and yet they are not liquid or you decide not to liquidate them, then the RSU price could go to zero and you’ve lost more than everything because you can’t necessarily recoup the taxes.

That said ISOs have similar risk but additionally you could lose whatever you paid to exercise and also you could incur AMT which complicates your tax return quite a bit.

That’s not how it _should_ work. RSU grants are normal income. Taxes should be withheld as such by the granter. Which is the assumed reason Stripe is raising money. Because they are on the hook for withholding and must pay that bill in cash.

Now, like all income if you set your withholding incorrectly you can owe at the end of the year.

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