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Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by choppaface on Wednesday March 08, 2023 @08:42PM (#35077361)
At Uber, employees got loans to cover exercise. Is that not happening here?
Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by nrmitchi on Wednesday March 08, 2023 @08:48PM (#35077401)
Taking out 7-8 figure loans to exercise start-up options in a private company in a time of decreasing valuations and market uncertainty sounds like a pretty poor idea.
Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by akavi on Wednesday March 08, 2023 @09:14PM (#35077583)
You can get loans backed by the shares themselves. Ie, the lender gets x% of the shares, rather than being paid back a specific dollar amount at a later time.
Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by runako on Wednesday March 08, 2023 @09:40PM (#35077753)
In this market, the X% might well need to be so near to 100% as to make the transaction not worth doing.

For ex: Stripe has marked itself down ~50% over the last year. Suppose you think the haircut should be more like the 70% comps like SQ and PYPL have taken, and build that into the X%. Then on top of that loss buffer, you prudently demand an illiquidity premium and a profit margin. That arithmetic doesn't leave much room for the employee to retain any stock.

Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by zamnos on Wednesday March 08, 2023 @11:02PM (#35078208)
More explicitly, if the shares go to zero, you don't owe any money
Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by nrmitchi on Thursday March 09, 2023 @03:31PM (#35086257)
If the shares to go 0, and the loan is discharged, the discharged amount is still considered taxable income (at least if you are subject to US taxation)
Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by choppaface on Thursday March 09, 2023 @12:46AM (#35078630)
Right, that's what banks were doing for Uber employees, for AFAIK, as low as 7-digit packages. I believe the interest was conditional on an IPO happening tho, and in some cases the IPO not only got delayed but the IPO price was actually a little below secondary market price right before the IPO (same as Facebook).

I would think banks would do this again? But perhaps with a longer IPO window? Like the banks that would do this would also likely participate in the IPO anyways ...