Some years ago, I wrote a post that took Chris Anderson’s “freemium” model to task. In it I argued that once you had provided services and information freely, the conversion to payment was going to be a lot tougher. Free, I suggested, would become an implicit entitlement. Last week, in a withering attack in the New York Times, Ross Douthat lashed out at what he called “The Facebook Illusion”. Comparing Web 2.0 to the home ownership bubble, he took particular aim at the world’s biggest social networking site. The relative disappointment of its IPO should be read, he maintains, not as an indication that Facebook doesn’t make money, but rather that “it doesn’t make that much money, and doesn’t have an obvious way to make that much more of it, because … it hasn’t figured out how to effectively monetize its million upon millions of users … This “huge reach, limited profitability” problem is characteristic of the digital economy as a whole.” It’s probably a little early to call Facebook. Whether the IPO misfired or …