I don't think there is anything wrong with that. It's certainly riskier and subject to the whims of a fickle public. But there is also a bigger reward for success.
Saying that a new media company should charge their customers before they become popular seems counter intuitive. IIRC, this is how the Onion and many other major media publications began...they gave their product away for free until enough people read it that they could charge for ads.
It seems to me that most of the author's points could apply just as well to starting a new magazine or newspaper. Yet, I don't think that many people would agree that college newspapers are killing themselves by giving their products away for free. I think that the expectations people have for web startups would change if people looked at them as media entities and not software companies.