Look at it close enough... it's different even though it utilizes the milliondollar schtick. He's "selling" to a different audience for sure, and there is enough here to be TW newsworthy IMHO.

That's the media business. He's acting as media, which is his job. He's dedicated a share of his contracted air time (perhaps that's exploiting a market inefficiency in talk-radio, or perhaps it's defined within "artistic license" for now, until somebody decides to formalize that):

So if there isn't enough traffic from his audience to his site? Add appealing content, and talk about that.. just like a webmaster. But he's also now in the business of selling links:

Just like Google. That puts him into a category known as "black hat". Will his site be banned?

This one could disrupt talk radio / web as it exists. Howard Stern can start selling links, expire them monthly, and charge ten times as much as Liddy, or auction them all. What's to stop him? Or Oprah?

The charity thing is also noteworthy... it offers a carrot to soften the disruptive blow.... allow him (it's charity, after all wink wink) but then ban Howard Stern? Tough to be you, Mr. Cutts.