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Re:Liquidity Is Coming by iandanforth on Friday December 04, 2020 @10:27AM (#25303298)
Bonus-to-cover + early exercise seems strictly inferior to a 10 year guaranteed exercise window, what is your opinion on this?
Re:Liquidity Is Coming by ultrasaurus on Friday December 04, 2020 @01:49PM (#25306106)
There are 2 key tax advantages: Qualified Small Business, and avoiding AMT. (But should both be considered playing on expert mode, higher risk/reward.)
Re:Liquidity Is Coming by choppaface on Friday December 04, 2020 @03:29PM (#25307398)
And AMT can mean a $5k/year accountant if you want to play it right. IMO AMT risk not worth it unless the comp package is well north of $1m.
Re:Liquidity Is Coming by choppaface on Friday December 04, 2020 @03:27PM (#25307367)
The number of startups that IPO and 2x or better is strictly less than the number that even make it to IPO. The 10 year window is certainly better than 90 days, but options just increase your chance of being a bagholder.

In the case of an acquisition, options also can screw you. In my view, it’s always better to have either shares or equity most comparable to what the founders have. Be ready to sell early at any time.