Not gambling, but I have an old 401k from when I used to work for McDonnell-Douglas/Boeing. It has mostly Boeing stock in it, but also a bit of a bond fund and an SP500 fund. When the stock started to tank earlier in the year, I moved some of it into the other two funds...around $370 per share, I think. I bought a little bit back when it was around $350 per share. It crept back up, but then fell back into the $350 range again, so I bought a bit more.
I don't do anything crazy, just a little rebalancing here and there. I was in the Boeing 401k program from late 1997 until I switched companies either at the end of 1999 or 2000. It's funny, I used to remember dates like that really well, but I guess the older you get, the less relevant that stuff is, and it slowly slips from the mind. Anyway, I picked up all that stock originally in the $30-50 range, more or less.
What I really miss was the old McDonnell-Douglas days. I remember their stock was around $20 per share when I started in 1992. I was just part time in those days, and wasn't eligible for the 401k, but they always showed the stock price on the pay stub. I also remember it doing a 3:1 split, and then a 2:1 split, and finally, when Boeing took over, a 1.3:1 split, and Boeing stock was around $57/sh at the time.
So, in 5 years, $20 would have gotten you about $445, about a 22x increase. But in the next 22 years, you "only" got about a 6.3x increase ($359 as of yesterday's close divided by $57). Still, nothing to sneeze at.