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Re:When a Unicorn Startup Stumbles, Its Employees Get Hurt by encoderer on Wednesday December 23, 2015 @11:54AM (#10784199)
The wider the gap between the exercise price and the fair market value the more AMT you will owe on the shares when you exercise. By making a speculative investment -- by exercising early -- you will owe minimal AMT at exercise time and more capital gains later when you sell.

There are very real tax advantages to exercising early.

Re:When a Unicorn Startup Stumbles, Its Employees Get Hurt by nemo44x on Wednesday December 23, 2015 @12:20PM (#10784346)
If you really believe in the company and it's a rocket ship (some rockets explode mid-flight or stall though!) then I'd recommend buying some shares early on to hedge for the reason you state. But I probably would't early exercise 4 years of options on your first day at the company.