When mainstream companies buy hot young digital properties, it's often a story of faux hipsters walking into trouble. Witness the New York Times Co.'s stumbles with About.com, Microsoft's $6.2 billion writedown after snapping up the aQuantive digital ad business and the biggest horror show of them all, Time Warner's ill-fated hookup with AOL in 2000.
Not so for Advance Publications, the Newhouse-family enterprise famous for publishing the New Yorker , Vanity Fair and Vogue. Advance spent little more than loose change in 2006 to acquire Reddit, one of the Internet's edgiest news and comment sites. Now Advance could be looking at a 30-to-1 jackpot on a fast-growing property that's arguably worth $240 million or more.