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A comment on Stripe Faces $3.5B Tax Bill as Employees' Shares Expire. Parent comment

Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by caseysoftware on Wednesday March 08, 2023 @10:45PM (#35078105)
With (3), they'd be taxed on the gains when they sell. Not "tax free" at all.

The difference is that they wouldn't be taxed until the gains were realized not when they were imagined on paper.

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Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by tyre on Wednesday March 08, 2023 @11:01PM (#35078206)
The reason we have capital gains is to encourage investment. They're not investing $1 for 1m shares to build something better. They're getting $1m worth of something for $1, risk-free.

That gap between strike price and FMV is much more like compensation than it is an investment.

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Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by buryat on Thursday March 09, 2023 @12:08AM (#35078499)
you can borrow against this asset and get basically a tax-free loan
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Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by KptMarchewa on Thursday March 09, 2023 @11:09AM (#35082785)
Can you _actually_ borrow against completely illiquid, pre-IPO asset?
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Re:Stripe Faces $3.5B Tax Bill as Employees' Shares Expire by konfusinomicon on Thursday March 09, 2023 @07:58AM (#35080712)
exactly this. tax time will come, hopefully. until then it's a tax on monopoly money.
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