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.
The opportunity cost of this restriction on their lives is huge.
Had they gone public two years ago, employees would have benefitted from a market of a lifetime, with equity in one of the best tickets in town.
A lot of life changing early retirements and "Fat FIRE".
What restriction, exactly?
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.