A friend of mine lost nearly everything selling Yahoo! short in the bubble. He kept saying, this is riduculous, it can't go on. Eventually he was proven right but the window was longer than he imagined. By the time Google went public he got a second mortgage on his house and bought as much stock as he could at the IPO and held on to it. (I do thing he sold it in the high 600's).
On the apocryphal teenager story it would be helpful to have a citation since there were many stories of pump-n-dump artists in the dot com days, however most of them involved people doing actually sketchy, probably illegal things (like sending email spam to millions).
Up top you wrote: "He fully disclosed that he bought the stock and liked it."
But the articles say: "... the kid had bought stock and then, ''using multiple fictitious names,'' posted hundreds of messages on Yahoo Finance message boards recommending that stock to others. "
That latter is "classic" pump-and-dump. Create a fake pattern of interest in a stock you bought and then sell into that interest that you created. He should have been prosecuted since it's illegal.
I'm guessing his current 'newsletter' has the disclaimer it does (at least according to Wikipedia) because now he knows if he doesn't include it he'll go to jail.
That isn't the whole story according to the book. In the book, he explains that he tried posting hundreds of messages under his own name, but there was some mysterious limit on multiple posts, so he created the extra accounts. Michael Lewis wrote that he didn't try to make them look like separate people, just separate accounts. Furthermore, he posted the exact same message, either through lack of guile or lack of intent to deceive.
In his emails he said he liked the stock and owned it. How is this deceit? He liked it and owned it. He said the price would go to such-and-such. It did. If I post here on HN as raganwald and again as regbraithwaite, is it deceit? How? There is no strong injunction against multiple accounts on HN.
Given that the internet does allow you to create multiple email addresses and that Yahoo doesn't actually insist on one account per real person (unlike, say Facebook), Michael wrote that it is far from clear that he was breaking the law, which is why the SEC settled: They were desperately afraid of losing the case and having the emperor revealed to have no clothes:
There really isn't anything different between Jonathan Lebed and a brokerage leading an issue, except membership in a cozy little club. It's total clutching at straws to say he pumped and dumped but companied are allowed to hire PR firms to talk up their prospects.
Sure, the SEC will always try to find some trivial technical difference to justify closing the Jonathans down, it's just like a casino kicking a card counter out for "cheating."
On the apocryphal teenager story it would be helpful to have a citation since there were many stories of pump-n-dump artists in the dot com days, however most of them involved people doing actually sketchy, probably illegal things (like sending email spam to millions).