AFAIK most of the pressure is around RSU expiration, not options. So - no (Unless we're talking about Stripe changing this equity program even further)

But RSUs are shares and this don’t expire? ISOs and Non-quals expire after 10 years typically.

RSUs do expire if they do not have the qualifying events to convert to shares in time, with a window similar to option expiry.

It sounds like Stripe is going to declare a qualifying event which will convert outstanding RSUs into shares which will bring along with it a major tax implication for the RSU holders, who would be in a really tough spot if they got a windfall of totally illiquid Stripe equity. So Stripe is going to buy shares to facilitate tax withholding, for which they need the $$ they are raising.

Huh, did Stripe move to RSU-based packages earlier than typical? So they would have had to move from options to RSUs in, like, year 4 of the company? Didn't Facebook not do RSUs until year 6?

I think that’s right. If the RSUs had a 7 year window and they are expiring this year it means they started granting them in 2016.

Yes. Or if they permitted a legitimate secondary market.

RSUs are not eligible for an 83b election.

> RSUs are not eligible for an 83b election

I may have misread, but I think OP implied everyone would have been better off with options. There were a few years when RSUs were the craze, but they mostly screw holders.

The article is a bit of a mess as it says “exercise restricted stock units” which is not a thing.

Other reports have said that Stripe is raising to cover RSU tax bill that would come from letting them vest in order to prevent the RSU from expiring.

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

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.