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Re:Airbnb Plans to File Confidentially for IPO in August by twblalock on Tuesday August 11, 2020 @02:56PM (#24124360)
Couldn't they grant new options to the employees whose options expire?

An IPO seems like a pretty big hammer for that particular nail.

Re:Airbnb Plans to File Confidentially for IPO in August by beambot on Tuesday August 11, 2020 @03:06PM (#24124512)
Granting new options causes tax headaches: If strike price << fair market value, you get taxed immediately on the illiquid gains.
Re:Airbnb Plans to File Confidentially for IPO in August by refurb on Wednesday August 12, 2020 @01:26AM (#24128832)
At granting? I get annual option from my $10B+ annual revenue employer (where strike price < current stock price) and I don't pay tax until the options vest and I choose to exercise. Then I just sell-to-cover.
Re:Airbnb Plans to File Confidentially for IPO in August by twblalock on Wednesday August 12, 2020 @03:06PM (#24135577)
That depends on the type of options. Some are only taxable at exercise.