[cowmoo728]

I think you're confusing RSUs (Restricted Stock Units) and ISOs (Incentive Stock Options). Stripe employees were given ISOs. ISOs expire worthless if not exercised. And if Stripe employees chose to exercise their options, they were not allowed to sell the shares they received. So they would get a large tax bill on a paper gain, but not receive any cash to pay the IRS.

[mparkms]

Stripe started issuing RSUs ~7 years ago and the first of those are set to expire next year without a liquidity event, which is why they're doing this.

[hgsgm]

You are under-informed.

RSUs also expire worthless if not vested, and furthermore privately held RSUs are very hard to sell to cover taxes.

https://www.goodwinlaw.com/en/insights/publications/2023/02/...