[jonathankoren]

You can't "exercise options before they vest" because you don't have the option until vesting.

What you describe -- and as someone that was bit by the AMT wrt ISOs, I recommend -- is exercising as soon as they vest to minimize the gain between the strike price and the fair market value at time of exercise. If the FMV goes up, you're going to be stuck paying the AMT on the spread, and not even be able to sell your shares to cover the tax, because pre-IPO stock is effective illiquid. If you wait until after the post-IPO lockout date to exercise, you'll pay even more in taxes, but at least you can sell some stock to cover it. Ironically, this is actually less painful, because you actually have liquidity.

[lavezza]

I did some googling and it does look like some companies will let you exercise early but not let you take possession until vested. https://carta.com/blog/exercising-stock-options/#what-is-ear...

[nwatson]

Wrong, I've exercised pre-vesting at several companies. https://www.cooleygo.com/early-exercisable-stock-options-wha...

[compiler-guy]

TBF, it takes special arrangements by the company granting the options to allow this, and not all do.