But if the market recovers and they want to do an IPO then, wouldn’t they be in the same position if they IPOd now, and then growth of the market would cause their stock to grow as well?
Secondly, yes their stock could grow after the IPO, however the stock would be publicly owned at that point so the profit would go to the public shareholders instead of the current holders of the stock (founders, investors, employees).
I still think (and I might be wrong) Stripe put themselves in a corner position, and raising 6.5 billion USD after 13 years of operating to cover this cost seems like something that could definitely have been avoided.
Stripe can wait, that isn't the problem for them and is what they're doing. The board can also waive these fees, but that shifts liability from Stripe to each individual employee in question and that's the last thing they want, to piss off early employees.
If they then wait for the same time until they will wait until Stripe IPOs, the stock would grow to the same level.
There are lots of other considerations that come along with an IPO and Stripe is addressing the core problem (early employee liquidity) with a targeted solution.
(And yes -- they would've been better off doing two years ago. But timing is hard, and that's not really relevant to their decision now, which is the best at the current time given the past.)
But, they were put into this position for waiting for too long and not going public earlier. I have a feeling that Stripe is doing a classic 'emotional investor' mistake. They are considering their valuation to be 90b+, and see this as 'just 50, it will bounce back', not considering that company went from 0 to 50b. There is no guarantee that it will go above the current valuation, and anything below that is going to be harmful, even for current employees who were saved by this move.
What happens then?