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Re:Filing Taxes After Exercising Start Up Options by argigg on Tuesday February 21, 2017 @07:07PM (#13701547)
To state the obvious, the downside of early exercise is you might lose that money if the company does poorly.
Re:Filing Taxes After Exercising Start Up Options by jjirsa on Thursday February 23, 2017 @01:56AM (#13712167)
The downside of early exercise is if you leave before vested and your employer repurchases the shares, you're out the taxes you paid (minus some deductions in future years that will offset other gains but will still be painful for most people).