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If the lockup is 180 days, you can wait for a pretty long time before exercising. It's usually halfway apparent when a startup beings IPO readiness.

What gets you with waiting, if you have ISOs, is how much AMT hits you. If you're at a >50% IPO company, it's somewhat common to exercise as many options as you can before the AMT hits you.

It's also worth remembering that your 50% startup could be Wework. It's worth $9B, but was valued at almost $47B.



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