Perhaps this is the wrong question, there are "how much money did you make on your options" and there is "How much money would you have made if you had sold them when they were worth the most?"

You see I had some Sun stock left over from working there (about 8,000 shares) which at $60 a share in 1999 was $480,000, but after a reverse 3:1 split and selling them at $6 each in the Oracle merger they only netted me about $16,000. I "could" have sold them when they were $480,000 but I didn't. Not as severe a challenge as some folks in the dot com implosion but its something I think about from time to time.

If you ask what was the most money your options were worth on paper you get another (often higher) number. So if you were a Zynga employee on the day they went public you had some big value that they were worth but you couldn't sell until much later, and much later they were worth much less.

I owned 30,000 shares (common, not preferred) in a startup that I advised which when it was acquired only met the liquidation preference for the preferred (common stock ended up being worthless). At the last round of funding it was 'valued' at about $150,000 though. :-)

The bottom line is you can drive yourself crazy with possibilities if you aren't careful.