Media Entrepreneurs: Contextly’s Ryan Singel on delivering great recommendations, building newsroom tools and learning to ask for money

Alan Soon
Alan Soon
Mar 2, 2017 · 12 min read

Ryan Singel, a former Wired editor, started Contextly in 2012, wanting to make tools by journalists for journalists. Contextly is an engagement and recommendation platform that delivers the right content to the right reader. For publishers, it helps extend the shelf life of a piece of content. And for readers, it’s a way of getting deeper into a topic.

Ryan appears here as part of The Splice Newsroom’s profiles of media entrepreneurs reinventing the service of journalism.

Photo provided by Ryan Singel

Contextly has been around for about 4 years. What was the trend that you saw at that time that convinced you that this was the right thing to do?

I had been working for Wired for about 10 years from 2002 to 2012, almost completely on the online side, after two stints at search startups.

The speed of change in online publishing in that decade is hard to underestimate. Wired went from filing a small group of reported stories once a day (like a newspaper) to posting much more often all throughout the day. The production flow of pitch to assignment editor to morning meeting to assigned word count to editor to photo desk to copy desk to front page editor collapsed. In many cases, writers took over nearly all those duties.

But at the same time, our tools hadn’t gotten smarter — even if they’d gotten faster. One of the main benefits of online publishing is that all the archives were online; context was available via smart links. And yet online publishing was focussing on the now.

I wanted to make it easy for readers to dive deeply into a story and understand the context. I got a small prototype done and Wired began using it. The popular weblog BoingBoing asked to borrow it and I realized there was a need for this.

I realized there was a problem and that I knew how to solve it. After that, it became a challenge to prove that I was right.

What’s the itch you wanted to scratch by doing this?

I spent two years before Wired working at search startups, and my favorite part of that job was hacking internal tools, even when higher-ups didn’t agree. At Wired, I could see how this context problem was broken. We felt it everyday in the extra editorial work we had to do to find and present links to readers. We’d drop those into the HTML of stories, where they’d be frozen in amber.

When I realized that these links belonged in a database, where they could change and be updated over time, I realized there was a problem and that I knew how to solve it. After that, it became a challenge to prove that I was right.

How do you describe your service today? How has the product changed in the last 4 years?

The product has evolved so much. We started with a tool that made it easier for writers to choose related stories and they had to choose related stories. We then realized that not every reader wanted to go deep, so we added some recommendations to new, unrelated stories in a separate section and added backup related links so that if writers didn’t choose links, there would be some basic related links.

Then, on the strength of early customers, I got into a media-focussed accelerator called and met a data scientist named Ben Autrey. He took the basics of what we were doing and supercharged it, adding machine learning and natural language processing to the system. This was key to us evolving as a business, and Ben became a co-founder and CTO.

We are now an engagement platform, helping to get the right stories to the right readers, in a growing number of ways.

With the intelligence we now get from understanding the content of stories and reader behavior, we now offer ways for readers to follow individual stories; for publishers to offer personalized newsletters and on-page recommendations. We can bring the best Twitter commentary about a publisher’s stories back to those stories so readers can interact with them. And we built a Channels product to let publishers create 10 to 20 topic-based newsletters that run without any editorial work.

We got paid less than the magazine employees, and we had fewer resources and less institutional respect and power. Pair that with a newsroom full of passionate reporters, editors and leaders with chips on their shoulders, and that’s a great recipe for innovation, especially as we were in the midst of a revolution in online publishing.

You were at Wired for 10 years as an editor. How did that inform your thinking around entrepreneurship and starting up?

The online side at Wired was an exercise in working for a startup. For the entire time I was there, the online side was the black sheep of Wired. We got paid less than the magazine employees, and we had fewer resources and less institutional respect and power. Pair that with a newsroom full of passionate reporters, editors and leaders with chips on their shoulders, and that’s a great recipe for innovation, especially as we were in the midst of a revolution in online publishing.

Culturally, the online side leaned towards saying yes to trying new things, including running early crowdsourcing experiments like having the readers help write a story wiki-style and giving writers complete freedom to publish-at-will. That’s still not common in newsrooms and certainly wasn’t at Conde Nast generally — or even at Wired magazine.

The crew that came of that time at Wired is pretty astounding: Mat Honan, Alexis Madrigal, Mike Isaac, Jenna Wortham, Spencer Ackerman, Evan Hansen, Noah Shachtman, Brian Lam, Joel Johnson, Quinn Norton, Kevin Poulsen, Kim Zetter and dozens more, who are now spread out across the media world at the New York Times, the Wirecutter, Buzzfeed, Fusion, The Guardian, Daily Beast, etc.

For a few years I also moved my main focus of coverage from security/tech policy to business and startups, so I got to know that culture up close. For instance, I wrote the first story ever about Y Combinator, now the most influential seed stage investing organization in the world. In that story, Reddit co-founder Alexis Ohanian bragged to me that the nascent Reddit had over 600 users.

Eventually, for better or worse, you start to think “I could do that.”

Do you ever look back and think, damn, I should have started up earlier?

I actually don’t. Prior to Contextly, I tried to build a business that would be a “copy-editing” service plugin for WordPress. I spent a bunch of time and money overbuilding it, only to find there was no market for it. I’d worked in startups before Wired, but it wasn’t until I was in the industry for a long time that I felt like I actually knew a real problem and how to solve it.

I think there’s a big difference between those who want to start a startup to start a startup, versus those who decide to start a company to solve a problem they are passionate about. I’m partial to the latter.

Did your peers think you were crazy to strike out on your own?

I think there was a little of that, but not as much as I expected.

I had a dream job as a journalist (and even being a journalist with a job is a blessing): I was editing a Wired section on hacking, security and tech policy, overseeing great journalists like Quinn Norton, David Kravets and Kim Zetter. But Wired was a place that sent people off to other organizations pretty regularly, including some to to startups. In fact, the day I announced I was leaving to run Contextly full-time, Wired magazine editor Chris Anderson announced he was leaving for a startup as well.

Do you still see yourself as a journalist?

I do. It’s in my bones. My closest friends are journalists and I even still host a Bay Area journalism get-together every few months. And sometimes I can’t help myself and I’ll lecture reporters on Twitter about what to cover or sometimes even commit an act of journalism myself on the side.

What would you say are your biggest gaps as an entrepreneur, and how do you fill them?

Understanding the institutional structures of large media companies and their internal politics — and how to get them to move. As a reporter and editor, I knew those were there, but they were problems way above my pay grade. As a company, we went through mentorship program from CNN/Time Warner called Media Camp. The folks that ran that, including Balaji Gopinath and Sandy Khaund, had been operators and knew how to grease deals and negotiate bureaucracies. I still lean on both of them for advice on working with larger organizations.

What things do you not like to do?

I dislike cold emailing and creating overly promotional marketing content.

When I started out, I’d quote our pricing and then immediately try to justify it or offer a discount. I finally realized that the best thing to do is to state prices simply and then shut up.

Journalists aren’t always good at asking for money. Was this a problem for you and how did you figure that out?

That’s funny you ask.

As a journalist, I got very used to talking to people, asking them about what they do, being improvisational on the phone, etc. That had long since stopped being intimidating. But as a journalist, you never end a phone call asking for money. When I started out, I’d quote our pricing and then immediately try to justify it or offer a discount. I finally realized that the best thing to do is to state prices simply and then shut up.

Our customers are used to paying money for services and I had to let the value of what we do speak for itself.

What do you know about yourself today that you didn’t know when you started the business? What have you learned about yourself?

I’m more resilient, resourceful and tenacious than I thought I was. And stubborn. Believing that you are right is a really powerful motivator.

The other thing I learned is how important it is to have supportive people in your life. You don’t need a crowd, just a few key people on your side.

Honestly, do you ever feel like giving up?

Of course. Every entrepreneur does. Much less so now than when we started. Starting something new is hard. A single day’s emotions can swing from euphoria (we’re going to land this big client!) to an intense feeling of doom.

The swings are the hardest part, but eventually you learn that the cure is to just do the next thing on the to-do list and breathe through the deepest doubts. You also learn not to believe the highest highs.

What lessons do you wish you learned earlier in the process of being an entrepreneur?

Two things I wish I’d learned earlier: A new business is a long slog to overnight success. Secondly, Silicon Valley tends to celebrate one type of success — a huge company with billion dollar valuations.

It took time to realized there’s a lot of definitions of success and lots of unheralded successes, including building a sustainable, profitable company that’s in line with your personal values and provides real value to its customers.

There’s obviously a certain lifestyle you have to be comfortable with. What did you have to give up to do this?

There’s three big things you sacrifice when you start an enterprise: time, money and energy.

A new venture takes a lot of time, and the distinction between when you are working and when you are not is hard to tell.

Starting a full-time venture means making very little, if anything, to start. Even if a company ends up raising a lot of money (and to be clear, raising a lot of money means selling substantial control and ownership to a third party), it takes time to build the initial product; investors expect much more than an idea.

So there’s no getting around sacrifices and learning to not spend money. We decided as a company to take very little investment and fight our way to profitability. While that’s harder road than raising a lot of money, it also means that we don’t have to depend on raising more capital or having investors dictate our product roadmap.

And energy is the least understood and perhaps the biggest sacrifice. Founders have to pour so much energy into the company, from worrying about servers being up to being fast with customer service to thinking about marketing to figuring out where they fit in the market to balancing books, that it’s hard to keep up energy for non-company things, like family, friends, outside interests, even reading novels. Having less energy for that doesn’t make you a hero. It’s just a reality and you have to work to make sure you keep energy for the other things in your life.

If you could look forward into the year ahead, what would be the one thing you’d want to celebrate at the end of 2017?

I think what we look most forward to on the product side is extending our vision of how to help publishers thrive in the digital era. There’s still so much potential for publishers, especially local ones, to connect to and serve their communities. Digital publishing is full of untapped potential.

On the industry side, we hope this is the year that publishers realize that platforms won’t save them — that platforms consider any individual media site as fungible and that publishers have to build direct distribution channels to and relationships with their communities. That requires letting go of timidity and seemingly easy wins, and aggressively thinking about how to serve the readership with innovative digital tools.

What’s the best compliment you’ve ever received from your customer?

Our company’s strength is two-fold: we’ve built some groundbreaking tech — like the ability to build storyline timelines without relying on tags and categories, and that tech is paired with an understanding of the industry and its daily editorial practices and blindspots.

For instance, one of the things we don’t do is provide a dashboard, which nearly all other SaaS companies do. Instead we send daily, weekly and monthly reports that are actually useful for the editorial team, including telling them what their evergreen stories actually are. So I think my favorite compliment is hearing from customers who asked in a sales call about a dashboard is hearing “We love your reports.”

My other favorite compliment came from Vox Media, which we talked to a bit about using our FollowUp button, but I got the distinct “not invented here” feeling.

A few months later, I saw this on their site. That was almost a year ago and I haven’t seen them build it yet. Followups are really hard to do right.

As a professional, what scares you about the future of media?

I’m most worried that the media world gets caught up in distracting initiatives like combatting “fake news,” when the reality is that the business and tech side of news still hasn’t adapted to the new digital world with any real sense of urgency.

For the most part, frontline reporters have: They’ve learned to be their own assignment editors, shoot video, engage with readers, write faster, embed social media, Tweet, etc. Meanwhile, management still has committees taking months to make small decisions and doesn’t invest in tech and experiments. The Washington Post, under Bezos, has been a strong counter-example, and the rest of the industry needs to adopt its approach. Unfortunately, there seems to be a feeling that you need Bezos’s money to innovate, when actually you just need Bezos’s spirit.

I’m also deeply concerned about the future of local media. I think 2017 will see a big shake-ups at large venerable publishers that used try to serve everyone, and we’ll see that at some VC-funded upstarts that are trying to also serve everyone. But there’s enough of this kind of coverage that I think readers won’t be too let down with these shake-ups. B2B and vertical publishers that serve niche interests can still thrive, especially if the old brands are willing to innovate.

But local news is a tough problem. Small markets may do better as there are few alternatives for readers and very local advertisers are less likely to turn to Facebook or Google to spend their ad dollars. But we see that mid to large-sized cities in the U.S., like San Francisco, Chicago, Los Angeles, Las Vegas and many more are shedding good reporters, losing big advertisers to platforms. That means essential coverage of local issues is growing threadbare. That’s bad for citizens, cities and democracy. And it’s spreading outside the U.S. as well.

This interview is part of a series of stories around the journey of entrepreneurial journalism and the different ideas that could help build sustainable models.

We want to showcase both the ideas and the courage that goes behind breaking new ground on the business of media. If you know of someone who should be interviewed here (or yourself), please drop me an email —


The Splice Newsroom: The business of media transformation.

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Alan Soon

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Alan Soon

Co-Founder, CEO of The Splice Newsroom. Covering the business of media transformation in Asia.

The Splice Newsroom: The business of media transformation.

We’re no longer updating our page on Medium. Please head over to our site for more —