Stipple Gets $2 Million to Help Web Publishers Bring Images Alive

A San Francisco startup called Stipple has raised $2 million from big-name investors to help make images on the Web more interactive. Specifically, the company wants to help publishers who puts lots of photos online to turn them into gateways to various kinds of interactions, including online purchases.

When you think about it, images on the Internet are weirdly static. The Web is dripping with them, of course, but they lack the interactivity that we expect these days from audio, text, and video. Stipple’s technology lets anyone with his own website layer interactive labels atop each image, including captions and what it calls “dots” offering details and links about specific people, places, or things. The information is invisible until a Web user mouses over the image. (Check out the images on Stipple’s home page for a taste of how this works.)

“Generally speaking you’re doing the same thing on the Web with images today that you were doing 10 years ago,” says Stipple founder and CEO Rey Flemings. “They are the forgotten media type on the Web. There hasn’t been a tremendous commercial focus on making it super-easy for people to discover what’s in photos. That was the initial idea of Stipple.”

That idea resonates with customers who’ve been using Stipple’s technology since the company’s August 2010 launch, including blog hosting company Six Apart, the E.W. Scripps newspaper chain, and record labels JIVE Label Group and Atlantic Records. And it appeals to the startup’s eclectic group of investors—it’s not too often you see singer/actor Justin Timberlake and staid Silicon Valley venture firm Kleiner Perkins Caufield & Byers backing the same company.

Stipple image illustrating 'people dots'Other contributors to the $2 million round include Mike Maples’ Floodgate Fund, Parkview Ventures, Quest Venture Partners, Global Brain Corporation, and individual investors John Ferber, Rick Marini, Eghosa Omoigui, and Naval Ravikant. In a press release announcing the investment today, Maples offer this buzzword-ridden yet succinct summary of the startup: “By marrying the ubiquity and engagement of photos with a business model and user experience that harnesses the power of community and network effects, Stipple has created the underpinnings of a company with disruptive potential in a massive market.”

Massive indeed: there are well over a trillion images on the Web, yet the only data available about most of them is their file names—and that’s usually something cryptic like “IMG_7149.jpg”. (Some images also come with metadata tags using the exchangeable image file format, or EXIF, but this usually only covers technical details like the date and time the picture was taken, or the settings of the camera used.)

Companies like Munjal Shah’s Riya have tackled the problem of making images more discoverable using computer vision techniques. Such algorithms are getting better at recognizing faces and certain kinds of objects, but aren’t yet able to attach specific, actionable labels. Riya’s software might have recognized a black handbag, for example, but it would never have known that it was a Kate Spade Metallic Priti bag, available at for $445. (Riya morphed into shopping site and was then acquired by Google.)

The other main approach to image labeling has been to let Web users themselves take care of it. Almost since its launch in 2004, the photo sharing community Flickr (bought by Yahoo in 2005) has included a “Note” feature that lets both the creator of a photo and random Flickr visitors attach text notes to specific areas of a picture; as with Stipple, the notes are invisible until you mouse over the photo. (I went wild with this feature in this 2005 photo posted on Flickr.) Then there’s tagging—the ability to tell Facebook and other sites that a photo you’ve uploaded includes specific friends, meaning that image will show up in their news feeds.

Flemings says services Flickr and Facebook have made a good start toward basic photo labeling, but says “there is a still a lot to be done.” He argues that digital files of any kind are much more useful to Web surfers—and much more lucrative for their creators—when they have five properties, namely that they can be easily published and consumed, and that they’re discoverable, monetizable, and what he calls “socialized’—looped into social media channels like Twitter or Facebook.

Stipple Dots on BritneyStipple’s service is designed to help with all of those things. It’s free to sign up—all a publisher has to do is embed a bit of JavaScript code in its website or blog, which enables Stipple to make all the images on that site interactive. Authorized editors can add captions or dots to images either from their content management system or on the live site. Say you’re a travel publisher and you’ve got a photo of your roving correspondent on the beach in Mallorca, Spain. You could write a basic caption, and you could create a “people dot” that shows up over the correspondent’s head and links to his Facebook account or his latest tweet. You could also create place dots for every beachfront hotel visible in the background, and have Stipple annotate these dots with text ads or links to reservation sites.

The information is unobtrusive until a site visitor mouses over the photo or touches the photo, if she’s using a touch-driven device like an iPad (Stipple’s technology is platform-independent, relying on basic HTML and JavaScript technologies rather than Flash or other proprietary formats). Whenever an interaction with a dot leads to a click on an ad or a purchase at an e-commerce site, Stipple earns a per-click fee or an affiliate commission, and it shares that revenue with the publisher. “We make money as our publishers make money,” says Flemings.

You can spot a photo that’s been “stippled” by the small black tab in the lower left corner—it looks like a corner mount in an old-fashioned photo album. Flemings calls this the “call to action,” and says it helps site visitors avoid wasting time mousing over images where no extra labels are present. But in the long run, he says, he’d like to do away with the tab: “If this works, the goal ought to be that there is no call to action—you just know that if there’s an image, you can mouse over it and it’s going to reveal all the information that’s there.”

Flemings is a serial entrepreneur who hails from Memphis, TN, where he headed an economic development agency for the local music industry. Since 2006 he’s been the head of Tennman Digital, a San Francisco-based venture incubator funded by Justin Timberlake. Tennman’s investments include Tapulous, a maker of iPhone games that was acquired this summer by the Walt Disney Company, and Particle, a “Web applications foundry” known for consumer apps like the video calling card system and the invitation system Crusher.

Flemings says the initial idea for Stipple came to him in 2008, but that other projects within Tennman kept him busy until December 2009, when the organization started sharing prototypes with potential users. “We showed it to large publishers and media companies, and there was immediate interest,” he says. “They want the ability to monetize images and share more information with customers. When you find a good opportunity with that kind of market interest, it can lead you down a path very quickly.” That’s what happened with Stipple—by August the company was ready to open its system to all Web publishers.

The idea of making digital photos more informative should be attractive to anyone who goes to the trouble of putting images on the Web—even individual photographers (who might eventually be able to tap Stipple’s technology through services like Flickr or Facebook; Flemings says the startup wants to build relationships with photo-sharing sites like the one it already has with blog host Six Apart). But at bottom, Stipple’s proposition is about engagement and e-commerce. And the big question is whether consumers are ready for the idea that browsing images on the Web could become an almost literal form of window shopping.

Stipple hasn’t released data about engagement rates yet, but Flemings says the early results have been promising. “We are a very data-driven company—mouseovers, the rate at which captions and dots are triggered, all of those things are captured and analyzed—and we’ve been stunned at the data,” he says. “One of the big questions we want to answer is, does this form of user-initiated content and advertising outperform display advertising, and we’ve been very, very pleased by the results.”

Now the startup just needs to sign up more publishers, and help them add genuinely useful data to their photos. (Flemings says Stipple has an in-house team that can help big publishers with thousands of online images power through the manual labeling process.) Flemings says he’s aware that if Stipple becomes just another way to litter the Internet with commercial messages, consumers will steer away from labeled images—he says the company has heat-map data from mouse-tracking studies, showing how consumers actively avoid mousing over ads that look like they might activate intrusive pop-ups.

“We absolutely believe there are best practices to doing this,” says Flemings. “While there is always pressure on a startup to earn the extra nickel of revenue, thankfully we have an investment group that wants to build a great long-term company. So [the labels] have to be around providing value in a non-spammy way. To the extent that we do that, we win. To the extent that we break the users’ trust, we lose.”

Xconomy goes the extra mile to bring you in-depth startup profiles. Compare this story to:

Stipple Secures $2 Million to Build Photo Tagging Tools for Publishers (Mashable)
Stipple snaps up $2M to easily tag the web’s pictures (VentureBeat)
Stipple Raises $2M From Kleiner Perkins, Mike Maples … And Justin Timberlake (TechCrunch)
After a new influx of cash, expect big things from Stipple (The Next Web)

Wade Roush is the producer and host of the podcast Soonish and a contributing editor at Xconomy. Follow @soonishpodcast

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