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Phil Bronstein, San Francisco Chronicle editor-at-large, said during the 2008 AlwaysOn media summit at Stanford that if he "could collect a buck every time anyone says 'monetize,' I wouldn't need any more money." But Internet users have come to expect free content. So, how will online media companies transform "free" into revenue? Nobody really knows-not even Google CEO Eric Schmidt, who refers to Web-based content profits as the Holy Grail.

How to cash in on the vast online audience for music, videos, news and other content? Media companies launching new online products find themselves weighing whether to build a subscription-based audience, charge on a pay-per-play basis, or rely on ad revenue. Online marketers tread the thin line between "free" and "fee" daily. For some strategies on converting the freeconomics of online media into monetization, here are three pieces worth a look:

Free! Why $0.00 is the Future of Business. Read what Wired's Editor-in-Chief Chris Andersen is thinking about free, in his blog and upcoming 2009 book on the subject.

"Let them eat chocolate." A Duke University case study on the power of that emotional hot button: free.

When Access was Free. A look back at 1999, when Netzero offered its Internet access service for free.

The Po!nt: Monetize with care. Judging the value of "free vs paid" offers online, in terms of their ultimate ROI, is a tightrope walk.

John McCain got people talking when he aired an ad that compared Barack Obama to style-over-substance celebrities like Paris Hilton; but the conversation really picked up when Hilton shot back with an entertaining rebuttal at the comedic website Funny or Die. Reclined on a chaise lounge-and attired in high heels and a revealing swimsuit-the celebutante outlined her own energy plan, a policy-wonkish hybrid of the McCain and Obama proposals, while also taking self-deprecating jabs at her vapid image.

"Infectious video content like the Paris video spreads like wildfire across the Web in under a week," says Chrysi Philalithes in a post at MediaPost's Search Insider. She notes that Google searches using the term "Paris Hilton" began to spike on August 5 and peaked on August 8 with a five-fold increase over normal volume.

Only a few companies seemed to capitalize on this heightened interest in paid search campaigns. When Philalithes googled Hilton's name, a paltry two ads appeared: one for Funny or Die and the other for Jeremiah Weed, which led not to the bourbon-maker's website but to the company's own YouTube reaction to Hilton's video. "Company strategists have recognized a pop and political cultural moment and are piggy-backing on to it to promote their brand," she says, "And they are not spending tens of thousands or getting buried in a time-consuming production schedule to do so. These opportunities have a short life span, so being quick to leverage them is crucial."