They say people won't pay for content. They say that paywalls are stupid and that its just not monetizable.
Remember when they said that people wouldn't pay for music?
What Apple proved, and what I suspect is the issue with web content, is that monetization was a product problem. I never would have paid for music back in 1999 or 2000 when I was sporting my 64mb Creative Nomad, powered completely ilegally by Napster. Why? Because it was a tremendous pain in the ass. Search quality was low, I had no means of music discovery, and the device has what might have been the worst piece of software ever written.
Enter the seemless iPod + iTunes experience, and the next generation goes back to paying for music again as if no one had ever heard of Shawn Fanning.
Same goes for television. Why hasn't Avner Ronen taken over the world yet? Because plugging a computer into your TV is still just too goddamn hard for the average person. Cable is easy. You call them up, they send a redheaded guy with a box and you're done. People pay for cable because its one less thing they need to think about.
The same absolutely can't be said for web content. Despite over 15 plus years of progress, little has changed about the way we consume articles on the web since the internet started. It's still largely a desktop experience driven and produced by publishers clinging to siloed production and consumption experience. Discovery sucks, as does the multi-device experience. The best hope you have for sending me an article that I read is to e-mail it to me or DM me on Twitter—and to hope that wherever I’m reading the web, I’m also checking messaging services. Even so, there’s no “read” box, or way for me to share back, comment, etc. Unfortunately, as long as content is produced by people who send nastygrams to people building great consumption experiences, like Pulse, and who want us to download a new app for every site we visit, you can expect little change.
There are, however, glimmers of hope--small examples of features and efforts that paint a clearer picture of what a great product experience needs to be. The full experience is largely broken, but you're starting to get a sense of what a complete, end to end, net-native content stack should look like—one that works and is sustainable as a business.
Here are the things that I think a real web content consumption product should have which would enable better monetization—better ads, easy passage through paywalls where applicable, freemium features, etc:
1) Read Everywhere
Amazon is *nailing* this with books. The one-click Amazon to my Kindle experience is fantastic. What’s even more fantastic is that it also goes to my Kindle Android app. Click, I have a book everywhere I read.
This is one of the frustrations with Instapaper, because it’s very Apple-focused. Kindle integration is spotty at best, and there are no official Android or Blackberry solutions. This is going to get even more magnified with the Android tablets start coming out.
2) Social
This is where Amazon is really missing the boat. Amazon uses the data of other humans, but not humans that 
you actually care about—which misses the opportunity created by influence. I don’t just want to read things that people like me read. I want to read things I “should” be reading because I want to keep up with certain people. The notion of followers and influence hierarchies is very powerful in the recommendation space. It also has social value. When I read what my friends are reading, I can now interact with them in different ways.
I’m using this to replace discovery, because, honestly, anytime a machine has ever told me what I’m supposed to read, it fails. More powerful to me is to know what’s trending through the system close to my circles and among people I care about.
3) Remix, Comment, Blog, Tweet
Tumblr really made it clear to the world that consuming content should be seamlessly integrated with sharing. Adding your two cents and passing something along in a seamless act of curation is a very powerful feature. It’s the reason I stopped using del.icio.us I felt like I was throwing stuff into a void. Now, I’m much more likely to share something on Twitter than I am to tag it in del.icio.us. Sharing links on my blog is to cumbersome, but I’d do it if I had a better clipping tool that posted.
4) Easy Payments that Ensure Virality
The reason why I’m so much more likely to pay for a Meetup is because it’s integrated with Amazon one-click payment. If I was sitting in my reader, and I saw a premium post that just required one click to open up, I’d be so much more likely to do it than to sign up for a single publication’s paywall. If I have to start typing in my credit card numbers the second I read something, I’ll just move on. However, if you let me read the premium article, but then you make me pay for it the next time I use the site when I have more time to sign up, perhaps that’s a better alternative.
On top of that, you could create a system whereby the more you share, the less you pay. Let’s say I was a tastemaker—where not only do I have a big following, but people like to engage on what I point them to. If you’re a publication, you actually want to give me that article for free, so that I can tell others to view it. If you make it transparent, and even layer on some gaming aspects that take quality of link sharing into consideration, you could incentivize people in an interesting way. If I just start randomly sharing, and the clickthroughs are low, I pay full fare. But if I show real influence, I pay less. It’s not Pay Per Post b/c you don’t know what the discount was until after you share.
5) Publisher Friendly
I don’t think you can be in the content consumption, delivery, discovery, etc business without being publisher friendly. How many cool sites are out there that do interesting stuff with music that have “all the indies signed up” but can’t get any of the majors on board. The same goes for textual content. You can’t have the NYT suing you or griping all the time, because, at the end of the day, you need them for distribution.
6) Consumer Friendly
People like Instapaper because of the simple and elegant design. To become the content consumption platform of choice, it needs to be so easy and so sleek that Steve Jobs himself would be impressed. That also means the experience starting from the product onboarding and the web article. Remember how awful the experience of clicking on an RSS button was? It can’t be that. RSS left it up to you which reader you wanted. Fail! Most people didn’t have a reader, and in being flexible, it became confusing. If you build an awesome reader that cuts across platforms, you can build up enough of a base that makes it worth it to publishers to add your add buttons. Bookmarkets, plugins, extensions, etc. all need to be so easy that you don’t lose someone right off the bat like when someone had to handhold you on how to use del.icio.us.
Ok… that’s all I got. Thoughts?