Shouldn't going public on an unrealistic market cap would cause more issues than benefits? Sure, a healthy exit is ok but later pressure to recover the market cap in the short term can cause heavy structural damages inside any org.
I think that's a more complicated explanation than necessary. If their private valuation is higher than their public valuation it means they can raise money more cheaply while private.
The restriction of not being able to liquidate their shares on the public market because of Stripe staying private for an unusually long time (Block (formerly Square), the other double-digit billion-dollar Silicon Valley payments company founded in 2009, went public in 2015). I imagine most Stripe employees that joined in 2019 and earlier expected Stripe to have gone public by now.
That they continue working at Stripe, instead of pursuing other life goals.
Or to phrase parent's point differently: by not IPO'ing, Stripe forfeited the premium public markets would have been willing to pay Stripe employees for their stock.
I'm not too sure about this. Stripe has double trigger RSUs with a 6 or 7mo lock up.
Let's say they went public in '21 instead of raising money in June of that year. The market would've already turned by the end of the lockup period. By delaying the IPO there is still some chance that the shares can be sold on the public market for more than the grant price -- I would note that this really benefits Stripe hired post-2020 but at this point that's like 75% of the company.
I doubt that last year was a good time to go public. At the stock market, the shares would likely have fallen by more than 28%. Plus, you can't sell RSUs right away, and watching them sit there and lose value is a pretty frustrating experience too...
The market caps of other Silicon Valley payments companies like Block (formerly Square) and PayPal peaked in Q1-Q3 2021 before declining in Q4. So if Stripe went public before Q2 2021 (to account for 6 month lockup period), their stock-holding employees should have been able to enjoy the opportunity to profit very nicely on their RSUs.