Reddit has billions of page views, but scant revenues to show for it. The New York Times' Mike Isaac explains why it is about to change.

The company is trying to jump-start its advertising business, as well as bolster some smaller moneymaking efforts. Its challenge is to figure out how to become a real business without changing the essential nature of the service and alienating its powerhouse constituency of 114 million intensely loyal monthly users. If it fails, those users could revolt and ultimately depart en masse, turning Reddit into an also-ran like Myspace — another social web giant that faded into obscurity.

One big problem is that Reddit might have to deliver analytics–user tracking–which will Displease the Community. But another is this: if an ad out there is remotely good, it gets posted by users as content anyway. Advertisers who already have a good shot at running "content" will always be hard to please with other offerings.