I'd prefer it be a reality not a story :-) but yes, it sure makes a great story.
I sold that Dell the same year I got engaged to my wife, 1994, and in the first several years of our marriage I kept saying: "If I had kept that Dell stock, we would now have $52,000" then a few months later: "...we would now have $88,000" etc, etc.
Finally she said: "Don't EVER tell me again how much we would have had, I don't want to think about it". :-)
Besides, it is only in HINDSIGHT that I can tell $55 was the high, in early 2000. It would have been impossible to know that & sold precisely then, right before the big downturn in the market. Chances are I would have sold way before then, or still be holding it (at about 1/2 the high).
Makes a nice "what if..." story, as you said.