Startup Stock Options – Why a Good Deal Has Gone Bad

Re:Startup Stock Options – Why a Good Deal Has Gone Bad by creaghpatr on Wednesday April 10, 2019 @10:49AM (#19625218)

Good point, although do long term cap gains apply to private company stock being held over years until the liquidity event?

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Re:Startup Stock Options – Why a Good Deal Has Gone Bad by bgentry on Wednesday April 10, 2019 @10:55AM (#19625295)

You get switched to long term capital gains 1 year after exercise or two years after the grant start date, whichever is later.

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Re:Startup Stock Options – Why a Good Deal Has Gone Bad by theIV on Wednesday April 10, 2019 @11:10AM (#19625452)

I don't believe the "or" part of this statement is right. I think you still need to hold for 1 year after exercise AND two years after the grant for long term to kick in.

Not sure what the best source on this is, but a quick DDGing:

https://www.fool.com/knowledge-center/tax-rate-on-exercising...

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Re:Startup Stock Options – Why a Good Deal Has Gone Bad by bgentry on Wednesday April 10, 2019 @12:05PM (#19626034)

I think we're saying the same thing.

If I early exercise my options on day 1, then I still have to wait until the 2 years after the grant date (2 years of employment) to get long term capital gains treatment.

If I wait 4 years, then exercise, then I have already satisfied the 2 years post-grant requirement, but I still have to wait a year after the exercise to get long term capital gains treatment.

The key part was my last clause: "whichever is later".

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Re:Startup Stock Options – Why a Good Deal Has Gone Bad by l2c1928 on Wednesday April 10, 2019 @10:50AM (#19625233)

I paid long term capital gains after selling a portion of my private stock via a tender offer last year.

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