I mean, it's something I've been considering for ages....
Well, a webcast, in and of itself, isn't a bad thing. However, get more than, say, two or three people together, and it becomes a group of guys sitting around telling in-jokes that nobody wants to see or hear. My first ever foray into Internet Radio was in...2001? 2002? My flatmate and myself set up a trial stream for a one-time broadcast, and sat around with a few guys just chatting random crap. Granted, we also did some pretty sweet prank phone calls around the world, including an "Kerpal's Dog" soundboard prank to a couple in Florida that showed the ugly truth to how racist old people can actually be. However, outside of that, it was three guys in their early 20s being boring.
I'd love to get back into the scene, as it were, but I really can't stand the idea of going back to Rogues Radio (for various reasons), and I'm not starting my own station again. The last time that happened, it was...bad.
The main thing you need is content. If sitting there watching Charlie Sheen say "Winning!" all the time is someone's idea of great content, more power to them. However, if I'm going to give someone an hour or two of my life, I'd like something in return.