We're discussing here a group of people who started their careers dead smack in the middle of the dot-com bubble, practically all of them in software/network security, a field that has stayed valuable since its inception. Of course they've done well for themselves.
This would be interesting if the denizens of #w00w00 had, say, invested in each other's companies. But as I understand it (I was a #!r00t person; our biggest win was ISSX) that's not at all what happened.
Sorry to sound pissy. I'm just hoping to forestall another goofy HN conspiracy theory; the idea that w00w00 is, like, the Internet's "Skull & Bones". No.
Also, I suspect the stories about w00w00 as a "hacking group" that broke into people's machines: total BS.