Part of me thinks they plan to make "enough" (however many zeros that happens to be) and then just disappear, and the ones we hear about are the ones who had too many zeros in their definition of "enough" or whose actual definition of "enough" is really "more."

A lot of the setups are so blatant though, that I think they are in it for the live fast, die young attitude. Make a shit ton of money, go crazy for a few years, get caught, do your time, repeat.

I first read that as "startups" and it's no less true.

Amen

From the article: "Insider trading is always bad and you shouldn't do it -- that concludes the advice portion of this section -- but sometimes people do it anyway. And sometimes nothing happens, and other times they get sued by the Securities and Exchange Commission and have to give the money back, and other times they get charged with a crime and have to go to prison."

Not everyone agrees that insider trading is bad. The United States SEC and DOJ are the only one that prosecutes it. When they do prosecute it, they have the stiffest penalties globally. And they only do it some of the times.

Well of course not everyone agrees it's bad. The people on the inside I'm sure think it's a great idea! The entire system would collapse if it was completely legal for business insiders to profit off investors, without the latter having any knowledge. Why would anyone invest if it was guaranteed you'd get screwed over?

There are entirely rational arguments for it, such as promoting an efficient market instead of wildly speculative prices. Some market participants will always have more information than others. The largest market participants being insiders and their friends that know their shares are going to be worth way less/more before the general public gets spooked/exuberant.

The laws deterring insider trading are - as you observed - to give people CONFIDENCE that they aren't going to get screwed. Confident to gamble in the markets, because they'll be "fair".

Stock markets aren't that popular around the world partly because investors don't feel like they won't get screwed over. Liquidity really does suck in most national and regional markets!

Its all a game of confidence man.

In many places, and yes you still see this in the US as well, the driving perception is that if you have attained a place in society to have privileged information, then you have the privilege of making money from it.

I'm in no way knowledgeable, but when I was younger, I remember my dad, who ran compliance at a financial planning/ life insurance place, frequently complaining about how much shady shit people could get away with because it was really hard for the SEC to actually put together strong cases.

Are you talking about the death puts scheme? It's not at all obvious to me that it should even be considered "wrong", let alone illegal.