For people with expiring RSUs, is the choice then to take this deal (@ at 50 billion valuation) or get nothing?
People have RSUs. Those RSUs vest at some point. When they vest, they have to pay taxes on them, at whatever value they have at that moment. This raise allows Stripe's employees to pay those taxes, and gives them a chance to sell if they want to. If they don't sell, they'll have to wait for future liquidity events, like private raises, buybacks from Stripe, or IPO.
The down round is appealing if you're intending to hold the shares until later, because you pay employee taxes at a low valuation, and then capital gains on the difference between that low valuation and your eventual sale price.
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/...
The down round is only appealing if you specifically have <1m in shares, have the cash to take a lower withholding rate, and value Stripe exposure so highly that it overcomes both the double-taxing and the opportunity cost of using cash for taxes. That trifecta is a nearly non-existent minority of former employees.
I don't think using cash to pay the taxes is even an option.
> If/When they choose to sell their shares later on they must then pay a capital gains tax on the difference between the vest and sell price, effectively double-taxing them on the difference.
Why are they "double-taxed"? After the withholding, you get shares with a cost basis of X (the price of the share at the liquidity event). Any future capital gain/loss is based on that cost basis. Where is the double taxation coming from?