When I was hired at AOL in 1995, I missed a granting period by two weeks. Instead of starting on June 1, I started on June 15, so that I could give two solid weeks worth of documentation work to my then-employer. That also mean that I missed a split. I was pretty peeved about that, but ultimately let it slide. I did get something like 3000 options valued at the next granting period, which I believe was like December 31st.
Fast forward a couple of years, and I got some more stock options as bonuses, as well as saw a couple of splits. In 1996, I did convert all the vested options I had to cash (with taxes taken out), which meant that I finally cleared $80k in options over my annual salary of $60k -- for once, the options actually made me more money that year than my salary did. That has never happened again throughout the rest of my career (so far).
And then things got toxic enough that I could no longer remain at AOL, and I left. Of course, I lost all my unvested options.
A while later, I did the calculations. If I had held on, and sold when the stock was at its peak, I would have cleared over $16m from the sale of the options. I could have retired at 30.
But AOL had become a toxic hellhole and no amount of money would have been worth trying to live through that.
Every time I see Gene Kim at a conference, he and I take up the next chapter in our ongoing series of "So, what was it like before the wall went up between devs and ops?" versus "So, what was it like after the wall went up between the devs and the ops?"
In the end, I had good experiences at AOL, and I learned a lot. And I'm glad I got out when I did.