And I'm not sure I'd classify making a killing on company stock options as "going into one or just a couple of stocks". I'd make the assumption those were not the only investments most of those individuals had.
I agree.
I personally did very well with some options, not they were not the only reason I retired when I did, though it helped a lot.
On the other hand, I (like to) think that it was a case of
"Luck is what happens when preparation meets opportunity" I did two things at my last job:
(1) for the ESPP I always maxed this out, but then when I'd held it long enough to get long term capital gain treatment, I'd sell half and put it into my normal, well diversified, investment portfolio. The other half I let ride. I wasn't betting everything on one stock, but I also was exposing myself to a great opportunity by accumulating shares a good prices. Yes, I had paid attention to the Enron debacle.
(2) I ignored my stock options for years - just holding them, but not paying attention to them as "income". In other jobs I had options and maybe made a few bucks, but often they were worthless. Since I didn't put any money into these options I wasn't risking anything. After a few years the stock
really climbed and I had accumulated quite a lot. I started to notice that if it went up much more it might push me into the land of financial independence. It eventually did and thats how I got to retire at 49 rather than a number of years later.
Lucky me!
On the other hand, I worked with many people who had the same opportunities and didn't reap the rewards I was able to.
One guy I recall cashed in his options after a slight run up and spent it on his house. Nice for him in the short term, but he missed out on a much bigger deal. Most people I knew sold their options when they were up a bit. They were content with a modest gain, but missed out on some really excellent gains.
And very few folks I worked with contributed the max to their ESPP (and sadly their 401(k)). I'd bring this up with some of my coworkers at times and they just didn't get it that they should be shoveling money into savings and that the company match and the deal with the ESPP plan was "free money". Sad.
So this wasn't lottery money, but truly what happens when preparation meets opportunity.