Most successful IM story you know well on a personal level?
I think for me it has to be Bankaholic. The site owner is believed to have sold his site for $12 million. I know the site well because the owner use to be a member of Digital Point forum. He use to buy huge number of links from other members. I think the huge payoff was in the potential the site had rather than based purely on what the site was making.
http://www.warriorplus.com/w/v/f2fwlp