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Not Content With Content: A Q&A With Contextly's Ryan Singel

The Internet offers a plethora of daily distractions.


Listicles. Viral videos. Videos you thought were viral, but were really Jimmy Kimmel — the Internet offers a plethora of daily distractions.

That makes the task of audience building infinitely more challenging.

Contextly, a content recommendation startup “designed for digital journalists by digital journalists,” is trying to improve the way websites engage with readers in the hope of turning digital window shoppers into daily readers.

The startup is the brainchild of Ryan Singel, who spent a decade at Wired’s website, where he co-founded the site’s Threat Level blog and covered topics like the NSA and tech policy. Singel left the media company to work on Contextly full time in November 2012, with co-founder Ben Autrey.

Last October, Contextly was one of seven startups selected by accelerator and early-stage venture firm Matter, which provided each team with $50,000 in funding.

As part of the Matter program — which was founded by PRX, Knight Foundation and KQED — the startups shared a co-working space in the SOMA neighborhood of San Francisco for four months.

Re/code caught up with Singel to talk about his new venture and the transition from one shaky industry to an even more unpredictable landscape.

Re/code: So what exactly does Contextly do?

Singel: Contextly’s mission is to build, engage and monetize a high-value audience. Our focus is helping publishers get readers to the right stories, give readers great context for stories and figure out ways to build loyalty and keep readers coming back, to eventually have them go to the site directly rather than using Twitter or Facebook as entry points to all of their stories.

How does Contextly differ from existing products such as Outbrain?

Singel: The biggest difference from a product like Outbrain or Taboola is they’re really ad units that have this sort of thrown-in recommendation to your site. Our focus is purely on engagement. And the other difference for us is more of a philosophical one, which is that we don’t send people off of your site ever. We are philosophically opposed to that.

And we are a combination of curation and machine work. One of the things we do is give publishers curation tools and editorial tools that allow them to control that section, control content recommendations, add input and intelligence into the system. We’re just a lot more than a little piece of JavaScript you drop into a template and forget about. What we really strive for is a combination of editorial wisdom and machine work.

In terms of the revenue streams for websites, would Contextly be taking away potential advertising dollars if it’s only linking to internal content as opposed to sponsored posts?

Singel: A lot of it depends on the CPM the publisher has. Building your audience is about getting people to read a bunch of your stories, and then they are more likely to come back in the future. If you send someone off your site on the first page view … if that visitor had stuck around and read two or three more pages, how much money would you have made from that visitor off that visit as opposed to sending them off the site?

So, for some publishers, their CPMs are super low, so Outbrain, Google, those modules are such a huge part of their revenue stream. But for companies that are not — either they have a high CPM or they sell products — keeping people around with more page views, engagement, in the long run we would make you more money than Taboola or Outbrain would. That model of sending someone off of your site to sponsored content of dubious quality is such a damage to their brand that it’s just not something they’re interested in doing at all.

How early on did you start thinking of the idea?

Singel: So, when I was at Wired, when you wrote a story, you would link back to the previous story or stories that you’d written on the subject. Beat writers know their beats inside and out, so we would always add links to the bodies of the story. Our biggest innovation was a text file that had the HTML you would use to drop links to related stories into the bottom of the post.

The genesis of Contextly was in reference to that, which seems obvious, but that’s metadata, data about the relationships between different stories, that’s something that changes over time. If you just drop it in HTML, you don’t have the intelligence to change it over time, so when that realization hit, we realized there was something interesting here.

It’s not about putting a little content widget down at the bottom, it’s about actually capturing this wisdom and intelligence that there is in the links between stories and making that dynamic.

I always like to tinker with things. I was always frustrated with our publishing tools and just publishing tools generally, so this started while I was at Wired. And it became the thing I started thinking about most in the shower, so it was the impetus to leave journalism, which was the hardest decision I’ve ever made. I covered things like the NSA and tech policy and I left in November 2012, so right before the era of [Edward] Snowden, which was maybe the worst time ever to quit.

What do you see as some of the major differences between working for an established media entity and a startup?

Singel: The online site at Wired has always been pretty scrappy, partly because it was one of the first online news sites, so there was always an element of trying new things, and something that is very similar between startups and news organizations is they are constantly shifting to something new.

The bigger difference is that there is a fairly set pattern in terms of what work looks like every day inside a fairly established news organization — like you have a regular meeting in the morning, you have a set of expectations about how many and what kind of stories are going to happen that week or that day. There is a pretty established pattern of how those things get produced and edited and promoted.

There’s room for experimentation within that, but in the startup world, all those things are constantly changing on a daily basis. What you expect to be doing today might change by 10 am, because all of a sudden, now it’s about talking to a client or switching what the priorities are. There’s just not quite that structure.

In the startup world, you’re constantly figuring out what to do next. All of a sudden you get an email from some company that wants to partner with you and it’s, “Let’s go have a meeting now,” and that feels very different.

This article originally appeared on

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