Btw this applies to those who are still employees too (if they explicitly bought vested options)
My advice to anyone joining a startup - if you have the negotiating power, insists that you must pre-exercise and purchase all options immediately when you start your job. You must put some money, but if you don’t believe in the company, why spent years there. Most companies don’t like this and their VC will object. This is why I said “if you feel you have the power to ask that”. If you can’t do that, exercise as soon as they vest
Edit: to clarify - this isn’t same as accelerated vesting. Vesting rules still apply - but you become a shareholder with appropriate rights.
I corrected by saying "vesting rules still apply". But the tax consequence (AMT or otherwise) will discourage one to exercise as the estimated stock price becomes bigger and bigger as the company grows.
If you do month 1: Strike price = $1. Pre-exercise, file 83-b with tax. Pay 0 AMT. You quit after 2 years, get to keep half the shares, company might pay you back the principal for the lost half (yes, there is a risk there)
If you do this 2 year when you quit, may be perceived value of stock is $10. Now you out-of-pocket cost = $1 + AMT tax on (income + $9). Moreover, you probably hate the company when you leave, so even more unlikely you will want to buy your options. I have friends who have lost $100k+ with that attitude.
These days, AMT cut off is much higher, but this could apply to some of the valley's sought after engineers.