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Key highlights in this report include:

• For publishers, the first step to monetizing something is to be able to measure it. The analytics tools now available make it possible to track the spread of content on social platforms closely.

• Until now there has not been a marketplace where those potential buyers and sellers of content could meet. Nor were there adequate tools to enable verifiable transactions between them. Tools like Cascade and Ricochet are helping put the foundations of such a market in place.

• Both publishers and licensees will need to seize the sort of ad hoc syndication opportunities that arise online and on social media networks. One of the major tasks facing publishers over the next three to five years will be to structure their repositories of content so they can be searched, sorted, customized, repackaged, and accessed in real time via standardized APIs.

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“If you look at content in the world in general, who is creating most of the stuff? Is it a better world if everybody’s creating? I think it’s a better world if everyone has the ability to create but I don’t think it needs to be that everyone is creating and gets equal attention because some stuff is frankly better than others,” he said today in a conversation with Om Malik at GigaOM’s Roadmap conference in San Francisco.

Since launching Blogger about a dozen years ago, he said he and his cofounder Biz Stone have been interested in democratizing the distribution of content online. But now, with both Medium and Branch, The Obvious Corporation-backed platform for hosting online conversations, he said, the focus is quality.

With Medium, the new collaborative publishing tool launched by The Obvious Corporation this summer, he said they want to provide a platform that enables anyone to create content but they don’t expect everyone to actually do it. And Branch similarly enables anyone to host an online conversation, but instead of opening it up to the masses, it lets users close it off to a smaller group to raise the bar of commentary.

He also said that while Facebook, Twitter, Instagram and other platforms may satisfy users’ obsession with the new and novel with a constant stream of updated information, Medium — which displays content in Pinterest-like “collections” of contents — is designed to give preference to higher-quality, longer-lasting and potentially longer form content.

People will always be attracted to the new and shiny object — and he said much of Twitter’s value comes from its real-time nature — but not all content on the Internet needs to be fast and fleeting.  He acknowledged that they sometimes wonder if they’re being “naive” to think that people might want more than the “junk food” content on the Web. But Medium’s hope is that people will “eat their information vegetables.” And If the site only appeals to a smaller audience in the process, he said, that’s just fine.

“Our goal at Obvious isn’t to reach the entire world, it’s to create as much value as possible,” he said. “HBO isn’t the most popular channel on TV but they do really really great stuff. And I’d rather be HBO than whoever creates “Desperate Housewives.””

Check out the rest of our RoadMap 2012 live coverage here, and a video recording of the session follows below:

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Launched in 2009 by three friends who met as undergrads at Yale, Williamsburg, NY-based Rap Genius started as a site where fans could crowd-source explanations of rap lyrics by annotating online text. Over the past few years, it’s grown to include millions of music fans around the world. But it’s also started to attract communities interested in annotating non-music-related text, from The Great Gatsby to the State of the Union address to Plessy v. Ferguson Supreme Court decision.

In an annotated (of course) announcement about the Rap Genius funding, Marc Andreessen said the startup’s broader mission is to “Generalize out to many other categories of text … annotate the world … be the knowledge about the knowledge… create the Internet Talmud.”

Rap Genius is about more than rap

With the new cash, the founders say they plan to not only annotate the world, but to create a social network out of it.

“Facebook makes sense as a social network because it’s based on where people went to college. But I think it makes more sense to build a social network around text – be it religious or literary – that people unite around,” said co-founder Mahbod Moghadam.

In his post, Andreessen also mentioned another reason —  which he said might even be the “real reason” — why his company was so interested in Rap Genius: it has the potential to annotate text across the Web, not just documents on its site.

“A big part of it is we think this is a way of creating historical documents that are going to live forever,” said co-founder Ilan Zechory.  ”It’s a new layer of Internet culture.”

As the site grows, co-founder Tom Lehman said Rap Genius could release Javascript or browser plugins that would let publishers and readers annotate documents across the Web.  While it wouldn’t necessarily replace some of what comments currently do, he said, it could enable people to comment directly inline and allow a community to really co-create content.

Andreessen noted that when he and Eric Bina first built Mosaic, they initially built a “group annotation” feature directly into the browser but later dropped it because their implementation required a server to host all of the annotation.

“I often wonder how the Internet would have turned out differently if users had been able to annotate everything — to add new layers of knowledge to all knowledge, on and on, ad infinitum,” he wrote. “And so, 20 years later, Rap Genius finally gives us the opportunity to find out.”

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That’s what CheckThis is shooting for. The newest micro-blogging platform, which launched out of Brussels, Belgium, announced today that it had raised $910,000 in seed money from a group of big-name investors. New York-based Lerer Ventures led the round, with Index Ventures, Betaworks, SV Angel, Hudson River Angels, Taavet Hinrikus and GroupeMe founders Jared Hecht and Steve Martocci participating.

With the new funds, founder Frédéric della Faille said, he and his co-founder are re-locating to New York in July to grow the business in a bigger market. While the pair spent time checking out different parts of the country, he said that with New York it was “instant love.”

“It’s about the community… and also the publishing and the media,” he said.

The more-than-Twitter-less-than-blogging positioning seems competitive with Tumblr, but della Faille said he believes they’re complementary because CheckThis is meant to create “temporary posters,” not time-intensive or long-lasting “posts.” It falls somewhere on the social publishing scale “between nothing and a blog,” he said, letting users express themselves spontaneously and easily.

The super lightweight platform doesn’t require any registration or setup.  It just prompts users to “tell,” “sell,” “ask” or “invite,” and then provides a basic template for filling in details (with words and pictures) and the tools for sharing it. Just as Instagram enables instant publishing for beautiful pictures, della Faille said, “we want to have instant publishing for beautiful posters.” (The Instagram connection seems to be more than just rhetoric as Instragam designer Tim Van Damme, also a Belgium native, is an advisor, della Faille said.)

Della Faille said he came up with the idea and built the company with friends three years ago. It picked up bursts of attention from users in Japan and Brazil, he said, but didn’t actually gain momentum until it was admitted to — and then won — the European accelerator SeedCamp earlier this year.

“We decided to apply like naive guys… [and then] we won,” he said. “Since then, it’s been going really, really crazy.”

In addition to the funding, he said, the company has grown from three employees to eight over the past two months. And, he added, with just organic, word-of-mouth promotion, users have created about 36,000 pages, with each receiving an average of 260 views.

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Thanks to a just-announced partnership with micropayment service Flattr, video producers using DailyMotion will now be able to tap into crowdfunding at the click of a button. It’s a move that the two companies think could change the game for online video producers.

“We’re always looking for interesting ways of monetization,” said Roland Hamilton, the U.S. managing director of Paris-based DailyMotion, which is the second largest video portal after YouTube.

“We’ve been really successful with our digital directors program, Motionmakers, but so far we’ve allowed people to monetize video through advertising — now we’re giving them another way to earn money for their work.”

Those who join the program can incorporate Flattr buttons on their pages, which allows users who are signed up to donate cash with a simple click. The Swedish startup — which likes to position itself as “the Like button that means something” — operates a hybrid donation-subscription model that allows users to put a stash of money aside each month, which is then divided equally between the various pieces of online content that they’ve liked over the course of the month.

“We hope this will change the way audiences think about online video,” said Flattr co-founder Linus Olsson. His hope? That people’s relationship with video producers will change if they can to easily donate money direct to creators of things they like.

Mutually beneficial

This move is tapping into an already-rising swell of activity around video and crowdfunding. This is already a big deal in the industry, particularly since the rise of Kickstarter, where film projects are proving massively popular.

But as well as giving video makers the chance to earn a little cash, the two companies hope it’s a mutually beneficial agreement for both of them as they strive for success.

For example the deal gives DailyMotion, which has long trailed YouTube, a chance to gain some ground in an important area. While YouTube has become a significant platform for video creators to make money, and the company has been aggressively pursuing online talent through its Partner program and the purchase of Next New Networks, its money is largely made through advertising.

Hamilton says it’s important to give some producers a different option — and of course it doesn’t hurt that it’s something YouTube doesn’t offer partners.

“You’re always trying to find the right balance of what you want,” he told me. “Some Motionmakers don’t want to have any ads at all, and some want to do custom ad campaigns in their videos. But this is a good alternative from having that ad pressure, if you don’t want it.”

“One reason we’re excited is that we have such a big audience — 123 million people each month, and 20 million of those in the U.S. — and allowing that audience to pay creators is very exciting.”

For Flattr, meanwhile, this is the biggest validation of its model so far — and that’s vitally important, because the service which has so far struggled to tap into the public consciousness. While the Swedish startup, which counts The Pirate Bay’s Peter Sunde as a co-founder, has found some traction in local markets like Germany, it has found it hard to secure major distribution deals to make its buttons ubiquitous online.

Olsson admitted that the deal with DailyMotion had been in the works for a long time — “To be honest, DailyMotion was one of the first companies that approached us, nearly two years ago,” he told me — but said that it may now be the right time for ordinary web users to switch on to the idea of micro-patronage as a parallel funding source to advertising.

“Kickstarter is for bigger projects that haven’t been done yet, but there are millions of pieces of content that are already in existence,” he said. “The important thing to remember is that ads require a big audience, but you can make money through Flattr with a small, dedicated audience.”

While he said it was impossible to know precisely how much partners could make because it’s entirely dependent on existing fanbase, virality, and so on.

“It’s extremely hard to say anything about what people might earn, the most traction has been with people who are very up front about it and say in their videos why you should use Flattr, and those who are showing transparency. There’s one German podcaster, Tim Pritlove, who has quit his day job and is living on Flattr donations.”

Right now the move only applies to creator-owned content on DailyMotion — and not those pieces of video that come through the company’s deals with copyright holders like EMI and Fox Sports — but it could expand to other copyright holders if there was enough demand, said Hamilton.

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Over the past couple of months, Gawker Media founder Nick Denton has made it clear that he doesn’t like blog comments very much, and that includes the ones on his own sites such as Gizmodo and Jezebel. He said so during an interview at South by Southwest, where he called the long-held idea that comments could somehow capture the intelligence of a site’s readership “a joke.” So Gawker is remaking comments from the ground up, Denton told GigaOM in an interview in his SoHo office on Wednesday — and the vision behind the changes that will be rolling out soon is nothing less than a reinvention of what the company is about, and also an attempt to literally flip the world of online content on its head.

This isn’t the first time Gawker has tried to fix commenting: the site got a lot of attention several years ago for launching an ambitious new commenting system that was supposed to offer readers an incentive system to encourage good behavior — a little like the membership model that other sites, including the New York Times, have adopted, which awards readers benefits for posting good comments. But Denton says now that this system actually turned out to be a massive mistake, and that all it did was encourage social-media gurus and professional commenters to game the system in order to get rewards:

It was a terrible mistake. It doesn’t work because people game it — and the people who game it are the people with time and social-media expertise, and those are not the people with information or insight. What person who actually has a job and a reputation… would give a f*** about getting some little badge like they’re in high school? It’s patronizing.

Everyone becomes a moderator of their own comments

So what is Gawker’s solution? The new commenting system, which Denton has hinted about but not revealed the details of, is designed to give everyone their own platform for commentary and discussion, one in which they control who they listen to or who they dismiss. And that includes the sources involved in a story at Gawker or Gizmodo or any of the other sites. That, Denton hopes, will appeal to people who don’t currently comment on blogs because doing so feels like “asking someone to go down to Occupy Wall Street and plunge into the mob and start shouting. No reasonable person is going to do that.”

In particular, Denton hopes that handling comments in this way will encourage the subjects of stories to become involved in rebutting these reports directly on the site, instead of calling him to rant at him about them. “I want to take all of those people and I want to have them in the discussion,” he says. “I want to see the story evolve and see the rebuttal, and the rebuttal to the rebuttal.” Not only does that produce drama — something Denton admits he has a fondness for — but he believes it could also help to get at the truth, broadly speaking.

Now I can say: your rebuttal will be given as much prominence as the original piece — we will respect you, we will protect you from the mob and we will let you say your piece. It’s great because it adds drama, and it keeps our writers honest.

Denton wants to reinvent how online media works

But Denton doesn’t just want to reinvent commenting; he wants these changes to be part of reinventing online journalism itself, by turning the traditional story model on its head. While many outlets treat comments and the discussion around a story as an afterthought, something that gets tacked on once the story is finished, Denton said he sees it not only as as the beginning of the story — but as the most important part. He said he even wants to take the discussion around a story that editors at Gawker engage in via private IMs and chats and make all of that public, as a way of sparking discussion.

This was actually the original vision behind Gawker: Denton said he noticed the discussion and gossip around a story in the newsroom or at the bar when he worked at the Financial Times was often far more interesting than the story itself — and he wanted to turn that discussion into its own form of media. In a similar way, the commenting changes are designed to make discussion among writers (who he said will be encouraged to spend far more time in the comments section) and readers and sources far more prominent, in some cases to the point where they become the story.

What’s interesting about Denton’s vision is that plenty of media sites both traditional and digital-only talk about how the “conversation” is the important thing, and how engaging the reader is a valuable tool for uncovering the truth, something that has been accepted wisdom since The Cluetrain Manifesto was published over a decade ago — but very few sites actually follow through on this promise.

Can Nick Denton manage to make Gawker into a poster child for that principle, and not only save comments and internet discourse but pave the way for the future of online media? And will anyone actually take him up on his offer to spend their day at Gawker moderating their own discussion? Stay tuned.

Post and thumbnail images courtesy of Flickr user Jeremy King

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The new feature, called the Explore Box, allows StumbleUpon users to surf through streams of content related to specific keywords or phrases they type in. By typing in keywords such as “New York City” or “Katy Perry,” you can now use StumbleUpon to peruse the web through a more narrowly directed content stream. Previously, you could only explore the web using StumbleUpon within certain sets of around 500 topics. With the explore box, you now have the option of viewing StumbleUpon content within hundreds of thousands of much more granular interests.

The Explore Box feature is launching on StumbleUpon’s web app Wednesday and should be deployed on its mobile apps in the near future. Here’s what it looks like to use (click image to expand):

In a recent interview, StumbleUpon CEO Garrett Camp told me that the reasons behind launching the Explore Box now are two-fold. First, customers have long been asking for a way to use StumbleUpon to find content on more specific things, such as their favorite celebrities or sports teams. And secondly, the service had to grow large enough for the deployment to make sense. Camp said:

“We’ve had a prototype of this for a while, but earlier on we felt like we weren’t getting enough results. We couldn’t really do it at the beginning because we needed a bigger index. In the earlier days, if you had typed in a specific term, you may have gotten just five results. Now, we have millions of pages of content, and it will just get better over time.”

Camp stressed that the company is certainly not abandoning its core goal of bringing serendipity to web surfing. “With the explore box, it still feels like stumbling upon things. But it feels like more focused stumbling,” he said. He was quick to emphasize that the explore box is not meant to be a search feature. “I think the term explore is better; it connotes that feeling of active seeking, but you still don’t know exactly what you’re going to get.”

Additionally, Camp told me StumbleUpon has started to bring in certain RSS feeds that will help bolster the amount of long-tail content it offers through the explore box as well as its flagship product. Previously, StumbleUpon only included pages that had been explicitly added by users.

In all, the explore box is just the latest example of how well StumbleUpon has been able to iterate very useful new features since it spun out from eBay  two years ago. As Camp told me in an interview last month, “Now that we’re independent again, you can have an idea here and make it happen very quickly.”

Here is a video of the Explore Box at work:

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StumbleUpon CEO Garrett Camp

At nearly ten years old, StumbleUpon is certainly well past the point of attracting users by being a new and hot trend. But the San Francisco-based web discovery engine has proven that slow and steady growth can still lead to success: Earlier this month, StumbleUpon surpassed Facebook to become the biggest traffic driver among social media startups in the US.

Given Facebook’s status as a media darling, its being unseated by the decidedly lower profile StumbleUpon has taken some people by surprise. I sat down last week with StumbleUpon co-founder and CEO Garrett Camp to find out exactly how the company has ascended to this point — and where it plans to go in the weeks and months ahead.

Here are a few main factors that have led to StumbleUpon’s recent strength:

• It’s a labor of love – Camp co-founded StumbleUpon in 2001 while doing post-graduate work in his native Canada. Since then, the company has been through its fair share of ups and downs — and Camp has been there through it all. StumbleUpon was essentially run out of its co-founders’ bedrooms up until late 2005, when it took on $1.5 million in seed funding and moved to San Francisco. Shortly thereafter in 2007, StumbleUpon was sold to eBay for $75 million. But like so many big M&A deals, the integration did not ultimately work out, and in 2009 Camp and one of his original co-founders Geoff Smith bought StumbleUpon back along with a group of investors.

   
  Camp’s dedication to StumbleUpon through thick and thin seems unique in an industry where the label “serial entrepreneur” is often worn as a badge of honor. The CEO told me he has stuck with StumbleUpon for one basic reason: It’s still the best place for him to turn his dreams into realities. “At the end of the day, I just really like the service,” he said. “To this day, when I have an idea, it always seems like StumbleUpon is still the best place to implement it. Now that we’re independent again, you can have an idea here and make it happen very quickly.”

• Technology comes first – More than two-thirds of StumbleUpon’s 80 person staff is technical, said Camp, who himself is trained as a software engineer. “There’s so much technology under the hood. We’ve spent so much time making the system, and by now it’s pretty complex and advanced.”

   
  Today, Camp said, StumbleUpon is just starting to reach the stage where enough people are online to really take advantage of the system. ”For the first several years we never made a proactive effort to talk to people. I was in Canada in grad school, and then in eBay there wasn’t a lot of press either,” he said. “In the last couple years people have really paid more attention to us; but it’s taken us years to get to this point.”

• It’s no one-trick pony – StumbleUpon’s roots are firmly in the web — but Camp says that’s really only the beginning. According to him, the company’s core technology can be fairly easily translated to many other mediums such as television, gaming, social networking, and beyond. It branched out in November with an app discovery service for Android. “The idea of providing recommendations without knowing exactly what you want can be useful in so many places,” he said. “We’ve built this backend, and now we can focus on one or two platforms at a time. But the only limitation [for growth] is the number of engineers we have.”

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