Earlier in the year, I had a sit down interview with Roger McNamee, where he talked about why social was over, how Google was making bumbling mistakes, and why the opportunities being opened up by the mobile Web represented one of the most exciting times to be an investor he’d ever seen.

He’s looking half right on the first two. Facebook’s disappointing IPO has made social look a lot less appealing. Meanwhile, Google has had some less than stellar moments this year, but — today’s earnings miss not withstanding — its shares have been soaring since the great May face-bomb, hitting heights many investors thought Google would never see again.

Mobile is undoubtably only getting bigger. One in seven people have a smartphone now, and many of them are just scratching the surface of using it for more than texting and email. Mobile is already making relatively young giants like Facebook look old, and it’s sending shock waves through ecommerce. With more than 20 percent of ecommerce browsing happening on mobile and sales conversations 75 percent worse, it’s a category that everyone has to pay attention to.

But McNamee’s hopes that mobile would free content creators from a Google-dependent Web existence, allowing them to create quality content ripe with monetization potential, are already looking dim. The industry had a chance for a “digital do-over” where it could set the expectation that content, games, and apps that add value would cost money — not a lot of money, maybe just a dollar or two. The wow! factor of carrying the Internet around in your pocket was still fresh, and iOS sports the inherent plumbing for micro payments that the Web never did.

Well, so much for that. While ebooks, movies, TV shows, and music are all enjoying micro-payment mobile and tablet life, the rest of the things we consume on these devices have mostly defaulted to free, costumed with jockeying for position in Apple’s rankings. Entrepreneurs have substituted one “eyeballs, then cash” business model for another, and one third party gatekeeper for another. Flush with venture cash, it’s as if they can’t help themselves.

And for ecommerce, that’s not so bad. Companies like Braintree are aggressively pioneering one-click payments that make the model work, and in some cases, it opens up entire new windows to shopping at times when people never bought online before. One Kings Lane found that mobile gave them surges in purchases on Friday nights and holidays — and crazy expensive purchases at that.

But the rest of the mobile Web is once again in this uncomfortable oh-I’m-sure-we’ll-figure-it-out mode that has eerie similarity to the eyeball hopes of the desktop Web. Only there’s a far worse twist: Volume won’t bail them out. Companies like Foursquare and Shopkick keep saying their customer interaction points are of such a higher quality that they can create huge companies off a fraction of the users it takes on the desktop Web — quite possibly less than 100 million.

Most of the periods of we’ll-figure-it-out monetization plain haven’t worked. Google is an exception, and display advertising is an exception, because of the torrent of users sites like Yahoo and Facebook were able to amass. It’s a lot to hope that the mobile Web —  being built by the same investors and entrepreneurs in many cases — will have better luck.