Welcome to Press This, the WordPress community podcast from WMR. Each episode features guests from around the community and discussions of the largest issues facing WordPress developers. The following is a transcription of the original recording.
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Doc Pop: You’re listening to Press This, a WordPress community podcast on WMR. Each week we spotlight members of the WordPress community.
I’m your host, Doc Pop. I support the WordPress community through my role at WP Engine and my contributions on torquemag.io. You can subscribe to Press This on RedCircle, iTunes, Spotify, or your favorite podcasting app. You can also download episodes directly from WMR.fm.
Now, the media landscape has always had its ups and downs, but the past few months have felt particularly grim to me for journalism. Prominent newspapers like the Washington Post and Los Angeles Times have had massive layoffs in January.
And since then other sites like Sports Illustrated, National Geographic, Pitchfork, and Vice—that’s a big one—have had their newsrooms gutted, turning them effectively into ghost brands. These companies will still exist as a brand, but just without the journalists.
In the wake of all this, we’ve seen a few successful worker-owned sites like Defector, Flaming Hydra, and 404 Media popping up and doing great journalism. We’ve also seen the rise of independently owned newsletters powered by platforms like Substack, Patreon, Ghost, and yes, WordPress.
I wanted to learn more about the future of publishing so today I’m talking with Ryan Singel, the Co-Founder of Outpost Publishers Cooperative, which helps subscriber-driven newsletters and sites thrive with independent tools rather than using the VC funded platforms of the olden times.
Now, Ryan is, like I said, the Co-Founder of Outpost Publishers Cooperative. He’s also the founder of Contextly, which is one of my favorite WordPress plugins and a former editor at Wired Magazine, Ryan, how are you doing today?
Ryan Singel: Great! Thanks for having me on, Doc!
Doc Pop: Yeah. Yeah. With that big bummer intro hopefully you’re gonna brighten things up today. I know that you came from the world of journalism. Why don’t you give us a little bit of your just a brief rundown of your WordPress origin story.
Ryan Singel: Yeah so I had had my own kind of blog sites. I think the first one I had was on MovableType, and then when I was working at Wired, which was part of a, you know, owned by Condé Nast, a big publishing, you know, conglomerate, we were stuck on sort of terrible magazine-centric CMS that we all hated, and we kind of had an internal revolt and managed to sort of get Wired to be allowed to run WordPress and it was a liberating experience for us.
So I think that was, maybe that was fairly early on. I wanna say like 2007-ish maybe I wanna say. And so just, it freed things up, launched a bunch of just sort of like standalone blogs that did really well. Folks like, and the biggest one people might remember is Danger Room, which is, was led by Noah Shachtman, who then became, you know, Editor in Chief over at Rolling Stone as of late.
But we were able to sort of, you know, it sort of freed us up and then as we were working, you know, working on it, I got frustrated with how we picked related stories for our posts and and eventually created my own solution and then left journalism to start Contextly, which kind of like makes it easier for people to show great recommendations back to their own content, whether that’s algorithmic or editorially picked.
So, WordPress, you know, both changed my daily life publishing and also changed my life in terms of turning me from a journalist into an entrepreneur.
Doc Pop: You know, I’ve talked to you several times on this show and a few others.
One of my favorite plugins, Contextly, is a WordPress plugin that allows people to have a way to keep visitors on their site longer. Like, they read an article and Contextly helps suggest another article, hopefully to keep them sticky and, hopefully to let you know what people are interested in. It gives cool daily information and analytics that are pretty different and more useful, I think, than Google’s analytics.
And we might talk about that later. I don’t know if that’s really relevant to today’s conversation, other than the fact that, I think, right after you left WIRED, you started thinking about the issues you faced in the times of journalism and publishing and kind of wanting to find solutions for it.
How do you keep people sticking around and using things like WordPress to use those tools? Currently you’re working on a project, the Outpost Publishers Cooperative, I don’t know if it kind of fits that vibe or not, but why don’t you tell us what’s going on there?
Ryan Singel: Yeah, so one of the things we really wanted with Contextly was, you know, you get somebody to come into your site is you want to get them to read more so that they come back, right? Or, you know, kind of become a subscriber or a loyalist. The goal we were trying to build there was really like how do you build a loyal audience, right? Not just, you know, getting sort of a viral hit.
But that was, you know, during the days of, the fire hose of Facebook traffic. So most publishers were just fine. You know, we didn’t care if we got people’s email addresses. We don’t care if they come back as long as we kind of just keep pumping stuff out and we’ll just make money off of the, you know, the Facebook ads and, you know, the Facebook traffic.
And that was a little frustrating. And then, you know, what we’ve seen is a change over the last few years, you know, where people are starting to sort of want to be loyal, they want to, you know, support the people whose stuff they like, right? Whether that’s on Patreon or or Substack or, you know, there’s a number of different platforms for that.
And then we started looking at Ghost, which is an open-source publishing system. That’s a little, that’s more sort of like, has membership and newsletter sending kind of baked into it and decided like, this was the, you know—felt like there was kind of a mixture of the zeitgeist of change in the world and people wanting to do some, you know, wanting to sort of build publishing, you know, sort of, I don’t know—build a publication that is sustainable and people being willing to pay for things. And just seemed kind of the perfect storm of sort of social, economic, and then technical changes.
It just became easier to run a site that is subscription driven. So I feel like it’s a continuation of what we were doing with Contextly and it’s an interesting moment to be in because it’s both full of peril and bad news and also lots of opportunity.
Doc Pop: You mentioned Ghost, it is an open-source platform. It seemed like it started off as a competitor to WordPress. I didn’t follow it very closely, but it feels like it then pivoted to, sort of, you say subscriber-based; I tend to think of them as powering a lot of newsletters while still having kind of a front-end kind of WordPress-y website.
Is that, is that kind of a fair thing to say is that they, you know, started off as a competitor to WordPress and pivoted to a slightly different model that focused on subscribers and newsletters?
Ryan Singel: Yeah, I didn’t follow them super early on so, you know, I think early on they wanted to be kind of the, you know, a fast, React-based alternative. We’re doing a lot of stuff to, like, help, you know, people run headless websites. I think a lot of their early clients, we saw a lot of, sort of, corporate blogs, you know, startup blogs that were running on a different-ish platform.
And they have kind of a different underlying architecture, so it’s more API-driven rather than plugin-driven. And I think it was about three, maybe three or four years ago now, they started to move to more of a sending out newsletters. And I like to think of it less as the, sort of like, you know, I like to think of sites as being sort of like—what I think Ghost is really good at is the subscription part.
The newsletter is kind of nice, you know, that it’s very easy to sort of write a post and send it, but I think, you know, with subscriptions, what you’re really kind of talking about there is sort of like the community-ness of it, right? Being able to easily get someone and sort of, like, have them, their member, I don’t know, their member-ness being like very much a part of your publishing system.
So, yeah, I think they’re less of a sort of a general attempt to be a general replacement, you know, in the way that I think WordPress feels like a Swiss Army knife where it can, you know, you really can make it kind of do everything, to being a very specialized tool that’s focused on publications that are really about getting members and distributing, you know, distributing via newsletters or being, you know, paid or graded content.
Doc Pop: We’re going to take a quick break here. And when we come back, we’re going to pick up our conversation with Ryan, and we’re going to talk about some of the journalist-owned publications that are kind of filling the gap and using these small tools to, like I said, fill the gap in the news space.
So stay tuned for more after this quick break.
Doc Pop: Welcome back to Press This. Today, we’re talking to Ryan Singel, a Co-Founder of Outpost Publishers Cooperative.
We are talking about how journalists can use new tools to hopefully fill the gap that’s left when these larger journalistic empires are now gutting and getting rid of their staff. I think of some of the successful stories that have happened in the past year: we’ve got Defector, Racket, Flaming Hydra, 404 Media, which is a personal favorite, Lever News, and Tangle.
These are just some examples. I don’t know if they’re all worker-owned, but they are all small publishers that are focused around finding sustainable ways to bring journalism to readers. Ryan, can you tell us a little bit about some of these sites and what they have in common?
Ryan Singel: Yeah, so I think what we’ve seen is, you know, we’ve got people who have, you know, journalistic experience right? They know how to write stories, they’re hungry, they want to move fast, and they’re looking for independence and so that they’re not at the whim of, you know, in the case of sort of newspapers, right, you get private equity that just buys up the whole chain or just bad corporate decision making or the reliance on advertising, you know, that’s where you just need tons and tons of page views in order to pay the bills.
And so I think what we sort of, the common thing is like, you know, everybody’s trying to do something new, but they want to do something journalistic, right? You know, they want to report news, they want to build a community.
And so I think we’ve largely seen is like most of them, you know, the main focus is build a loyal community, sending out things via email addresses, but, you know, can also be having their paid members get the paid version of their podcast, for instance, or join their Discord community, right?
So it’s just very community-focused, and then other sources of things like ads or even events, are kind of, they’re secondary to that. So I think what we really see is like a mixture of sort of a frustration with the current world, trying to do something new, and a tenaciousness to sort of fight their way to the point where they’re sustainable.
Doc Pop: Now, when I think of a few of these publications that we just mentioned, it seems like they are shifting from the days of ad-funded news and leaning in more towards subscriber-paid funded news.
And oftentimes it kind of, brings to mind paywalls. I don’t know if necessarily all of these are paywalls, even if they are kind of raising money from subscribers. But It definitely feels like we have the shift in how journalism is getting funded, but also in how people like you or I might interpret someone asking us for money up front for news, where I definitely two years ago would have been like, “why are you sharing paywalled articles?” And now I’m probably guilty of sharing articles that I’ve paid for without even thinking about, like, the old me trying to read them.
Is there like a shift in how this is being funded?
Ryan Singel: Yeah, there is a shift, you know, and especially on the small side. You know, I think you’re starting to see it, you know, we’ll see a mix of, you know, I think what a lot of people do is a mix of like, the majority or half of their stuff is not behind a paywall. We’re seeing more stuff that is behind, kind of, a registration wall, so you have to give your email address to read it.
And then some portion of the site being, you know, for paying subscribers only. And it’s definitely a tension, you know, because nobody really wants to paywall their stuff. But they, you know, at some point you kind of have to—there’s, you know, the calculation of like, “how do we get someone to go from being free to paid, right? How do we do this?”
In the kind of local news space, there’s a large portion of the, sort of new sites that are out there that are on a nonprofit model and don’t do any of the sort of, you know, sort of the hard paywalls. And then the memberships, they are generally kind of, cast as more of a, kind of like a donation model, you know, sort of a public broadcasting-ish model.
But that tends to mean they’re more reliant on grants and other sorts of funding because it’s just they just tend not to get as much membership money that way. But they see themselves as being, you know, a public service and, you know, often bringing news to communities that just don’t have any other source of news.
But there’s definitely been a change in the number of things that have gone behind paywalls that, you know, used to be only the Wall Street Journal could get away with it, and now, yeah lots of small indie folks are finding out that, you know, that can work for them as well.
Doc Pop: Emotionally, there’s a difference between me landing on a Washington Post article and being asked for money, and me landing on a 404 media page, where I know there’s literally four journalists who are getting paid with that, right?
It’s not like a whole staff-wide thing, it’s like, “oh, this is going to pay for your writing,” which also kind of goes hand-in-hand with, like, why I might be more likely to subscribe to a newsletter is because it’s like, there’s a person and there’s a name and there’s a human connection there.
Where if it’s a large company, at a certain point, and they’re asking me to pay for something, but there’s still ads and, you know, product marketing happening inside there, I’m a little less likely to do that.
Ryan Singel: Yeah, I think there was just, there’s just definitely been a shift, you know, and I don’t know if it started with Patreon, but like, there just seemed to be a cultural shift where, you know, we’re just more willing to hand over money to people whose stuff we kind of, like, we just want them to be out in the world, right?
We want their stuff to exist. We want them to be able to do what they’re doing and, you know, make a decent living doing it. You know, because, the amount of content you’re gonna get for, you know, ten bucks a month from a newsletter from someone who you really like, you know, you’re going to get a lot more from the Washington Post, at least in terms of volume, right?
You give the Washington Post ten bucks a year, you get tons and tons of stuff, but you may not get, you know—but that misses the person whose, like, perspective you love, or who is writing about a niche topic that you care about, or someone who’s writing about your local community. So I feel like there has been, you know, a aort of a cultural shift.
And then we’ve just also seen the tech tools have made it easier to do that. So, that smaller site, the 404media, has, you know, a membership system that I would say is as good as most mid-range publishers, you know, mid-sized publishers, you know, or even better. You know, some of those, some of the larger tech sites, larger news publishers have terrible tech.
So, it’s—there’s been a democratizing function of, I think, open-source CMSs and, and even some of the corporate-funded, well, you know, VC-funded ones that kind of goes hand-in-hand with that.
Doc Pop: On the subject of tech. If someone was running a WordPress news site and they wanted to get it funded, one alternative, we mentioned Patreon. Patreon has a really good plugin for WordPress that allows you to connect it and paywall basically articles so you can have your Patreon site, but you don’t have to just publish on Patreon.
You can still have a WordPress site that has, like, “Oh, to have access to this section, you need to, you need to do this.” And it might be like, some of your articles are free, but there might be bonus content or podcasts or things like that. I think bonus stuff is a way a lot of these people are doing it.
Like we’re providing a lot for free. But if you want a little bit more, or if you want this free without ads, here’s a way to do it.
Another alternative in the WordPress space is something you told me about. I haven’t heard about this, it’s called Newspack. Can you tell us about that?
Ryan Singel: Yeah. So Newspack is actually, I think, I believe they’re an offshoot of Automattic. So Newspack essentially bundles together vetted plugins that basically all kind of like local news people basically need, right?
So kind of including advertising analytics, ways to send newsletters, etc. And then there’s kind of a flat fee that you pay per month for them to provide all of these sort of vetted plugins and help your site run, etc.
Newspack has been around for a while, you know, and it tends to be used by smaller local publishers mostly. There’s money out there trying to help all the, especially around local news, trying to survive and come back, cause there’s been such a decimation of newspapers.
So the Knight Foundation, which is this gigantic foundation based out of Florida is now—has been traditionally giving money and giving grants and so forth, and now they’re going for a big push to essentially try and figure out how to make all of this sustainable and how to get local communities to get funding.
So they’ve got 500 million dollars that they’re wanting to spend over the next few years to try and revitalize local journalism, both by supporting individual publishers, organizations that help those publishers, and then also some of the tech. So NewsPack got, I think, something like eight million dollars from them to help build out this, sort of, like, this tech stack.
And then there’s a, yeah, and there’s a number of other tools. I think there’s Memberful, which is, I think also from Patreon in the WordPress space.
Doc Pop: And in the Ghost space, there’s Tiny News Collective?
Ryan Singel: Yeah, so they’re a little bit different. So Tiny News Collective would be one of those organizations that gets funded to help publishers. So they work with people that want to start something up, maybe, you know, who, especially in communities that just don’t get any representation, or in communities that just don’t have anything.
And they help them, sort of, launch something, right? So folks that, you know, maybe don’t have—don’t know what to do in terms of the tech, and so forth. So they’re big, sort of like, they help folks there.
And then they have their publishers that they work with use Ghost. So, and they’re kind of, they’re separate from Ghost, they’re their own organization, they—Tiny News Collective also got money from the Knight Foundation to help. So, Ghost is kind of off on its own sort of like, you know, in the same way Automattic is largely separate from all the things that you can do with it and the people helping it.
So Tiny News Collective…Yeah, so essentially, like, help people get launched, get them on Ghost, give them a nice-looking theme, and then give them kind of ongoing support in, you know, both on the tech side and the sort of strategy side.
Doc Pop: You know, we’re going to take another quick break and when we come back, we’re going to wrap up our conversation with Ryan Singel and talk a little bit more about CMSs such as WordPress and Ghost and talk about how they can help the future of journalism.
So stay tuned for more after the short break.
Doc Pop: Welcome back to Press This, the WordPress Community Podcast. My name is Doc. I’m talking to Ryan Singel, the Co-Founder of Outpost Publishers Cooperative.
And Ryan, early on in this interview, you mentioned your days at Wired and how there was an internal revolt about the CMS, and it kind of reminded me—and this was the CMS before they switched to WordPress—it reminds me, though, that I think just yesterday I heard an interview with Nilay Patel, the editor at Verge who said, I’m going to read his quote here.
“Boy, I’d like the reporters who work here to write for us in the text box that pays us money instead of over there in the text box that extracts value.”
Now what Nilay is saying there is that he’s seeing his writers having more fun publishing on, you know, Twitter or threads or wherever. And he’s like, “why can’t it be fun to publish here?” And he goes on in that interview to talk about some of the changes that they made to the CMS to, I guess, streamline it, to make it more fun. And I guess that just kind of seems relevant to what you’re talking about.
If it’s painful for a writer, if it’s literally painful to write on a CMS, then obviously they’re going to want to go to Facebook and write their post or somewhere else. Did you find that to be true?
Ryan Singel: Yeah, I mean, absolutely. So, you know, we had sort of the one main CMS and the workflow all worked through that and it was very slow and it involved the art desk.
And then when we moved to WordPress, you know, we ended up being, you know, I think we were actually like 10 different WordPress sites. So we had, we kind of changed things so that, you know, each sort of vertical had its own like WordPress site.
And so we could just do fun, quick posts. We could, you know, and one of my favorite ones we did back in the day is we—I remember when the Homeland Security had its threat level color-coded things, and every once in a while we would just make a fake version of that, you know, we did like a hot dog version, you know, with a, you know, Tijuana Danger Dog being at the top, and then a vegan pup being at the yellow color. And, you know, we could just write that, send it out, it was fun, right? And then we would still go do the real journalism kind of stuff.
But we couldn’t, you know, when we didn’t have access to the CMS ourselves and, you know, couldn’t press publish, you know, ourselves. We had to wait to go through, you know, four levels of editors and the art desk. So it did make things a lot more fun and things got a lot more experimental and we were able to try things about what would happen if we, you know, published ten posts a day really quickly, you know, little short things, or, you know, should we focus on long form? Or so forth.
So it was just a really fun time, you know, sort of putting that publishing power more towards, you know, in a large organization, pushing that down so that, like, individual writers and editors could make decisions and do things quickly really did revolutionize what Wired was like in the 2000s.
Doc Pop: You’re mentioning experimentation and how y’all could kind of play around more quickly. I do hope that maybe something that happens from all of this, I do worry about, not the sustainability of these smaller sites, but like the fact that they are not going to necessarily hire as many people as ou know, previously it’s, you know, all of these collectives we’re talking about are still pretty small.
But the one nice thing about having a small group is that they can experiment more and they could create their own Mastodon instance or whatever. And that way, when they’re writing in the small box that that isn’t the official website, it could still be like their Mastodon instance or something like that.
You know, maybe we’ll see people kind of trying different things and experimenting more and still owning more of the content as a result, and not just willy nilly sharing the content around onto other platforms that are extracting value from them.
Ryan Singel: Absolutely, yeah, I think we’re going to see some fun experiments with that and so, you know, I would love to see more of, you know, even when you do sort of like share out there doing that sort of like “POSE” thing, you know, the “publish once, syndicate everywhere” idea from the IndieWeb, where even if you do share your stuff out there, it’s still live somewhere on your own site, right?
And you can do more fun, interesting things. So if you want to do your snark it can be over there on the, you know, in the sidebar or in a different part of the site, right?
You know, the main homepage still looks serious, right, but then there’s the the fun places, you know, the places for people to do things that are a little more fun and not, you know, necessarily, you know, the kind of thing that you’re going to have show up in Google News, right?
Doc Pop: And on that note, Ryan, where is a good spot for people to follow your snark online?
Ryan Singel: Yeah my snark these days is mostly over on Mastodon. I am RyanSingel, all one word, and that’s S-I-N-G-E-L @writing.exchange. And then the sort of the fun stuff we’re doing to help publishers on the Ghost Platform build their businesses, you can see what we’re up to over at outpost.pub.
Doc Pop: Outpost.pub, and here I see the list of services you’re proudly powering, including The Atlantic, 404 Media, Tangle, Future Crunch, a lot of great stuff here, Vallejo Sun. So that’s super cool to see that, you’re part of those awesome networks.
Well, thanks for listening to Press This, a WordPress community podcast on WMR. Please visit TorqueMag.io to see transcribed versions of these podcasts, plus more WordPress news and tutorials. You can subscribe to Press This on RedCircle, iTunes, Spotify, or download it directly from WMR.fm.
I’m your host, Dr. Popular. I support the WordPress community through my role at WP Engine. And I love spotlighting members of that community each week on Press This.
