34 | Special Episode: WordPress Publisher Sessions
19 Nov 2025 · 72 min
Episode 34 (WordPress Publisher Sessions) is a recorded panel (hosts: Pete Ericson, Leslie Sim of Newsletter Glue, Steve Burge of PublishPress, plus Stuart) focused on using newsletters to build community and boost revenue for WordPress publishers. Key recommendations: treat newsletters as a relationship channel (personalize, use bylines/photo, editor’s note), ask subscribers to upgrade (soft asks and member perks), shout out and engage readers (publish replies/testimonials), segment newsletters by topic or cadence, automate drafts via RSS but keep an editorial curation step, favor consistency in schedule over frequency, use free registration to capture first-party emails behind a tighter paywall, consider premium newsletters (full text, no ads, early access) for monetization, and leverage cross-promotion and curated roundups to grow high-quality lists. Technical notes discuss common ESPs (Mailchimp, ActiveCampaign, Mandrill/Piano) and implementation approaches (RSS-to-email, transactional sends, per-user programmatic emails).
Chapters
Welcome to episode 34 of the Paywall podcast. This is a special episode where we feature a new group called WordPress Publisher Sessions, hosted by myself, Leslie Sim from Newsletter Glue, Steve Burch from Publish Press. And our mission is to help publishers who use WordPress succeed. In this episode, Leslie is going to talk about building community and increasing revenue with newsletters. Newsletters are critical to your publishing operation and we hope you enjoy this. So let's jump in. Welcome to WordPress publisher sessions number one. This very experimental session is brought to you by Leslie Sim, who's going to talk about newsletters from Newsletter Glue, Steve Burge from Publish Press and myself, Pete Erickson from Leaky Paywall. And we are all involved with publishers and their success. And after wordcamp for publishers has sort of slowly died off, we thought we'd step in and. And see if we could share some knowledge and help publishers that use WordPress succeed. So we have session one here, building community and increasing revenue with newsletters. And Leslie, you want to take it away and we'll just dive in. And as I would say that if we. Questions for those that are joining us, let's save them to the end and we can have a little discussion as well. How's that?
Cool. Yep. Thanks, Pete. Actually, I'm going to contradict you over there and just say that if you have questions, just because it's like this is the first session and we're just kind of feeling out how we want to do things. If we have questions during the thing, we can like, just go ahead and ask them and we can figure it out as we go.
Sure, let's do it.
Yeah. All right, so this. Oops. So today's session is about building community and increasing revenue with newsletters. And the way I wanted to approach this was kind of talk about the high level principle and the way you approach newsletters and how they're different from other marketing channels. So as publishers, most. Well, most publishers have a website, they have a social media presence, they have newsletters, they might even have a podcast, amongst other marketing channels that they have. Maybe, you know, you can consider ads as a marketing channel as well. And so you want to really think about them on two different levels or ways. So with discovery, you've got the website, which is SEO and social media and paid ads. And the what people are expecting from you there is quite different from what people are expecting with newsletters and podcasts. And what I mean by that is that when it comes to newsletters and podcasts, people have opted in. Right? They have to subscribe to you in order to get the content. And that means there's some sort of, you know, I like your content, and I've decided to subscribe to you going on there. And so by the time you get to that, there are a whole bunch of implications, and there are a whole bunch of things that change as compared to what you can do on your website with your articles on social media, Twitter and stuff like that. And so I wanted to kind of go through some of those implications and how you can leverage them to grow your community and get more revenue.
That's what we want. Yes.
So a couple of things. The first is that you can actually be a lot more personal with your newsletter and go a lot deeper than you can on Twitter, for example. So if you're a writer or an editor with an article, maybe not so many people might know your name. But if you're writing the same newsletter, going out to the people who have opted in, they're going to see your name every week or every day. And after a while, you build a relationship with them, and so that changes how you can relate to them. And I'm going to go through. Let me just go through. Go through each one by one, rather than getting stuck here at kind of like the contents page. Okay, so the example I gave here with the deep personal and going deep was the Washington Post. So I'm kind of a little bit of a newsletter nerd. So I've signed up for a whole bunch of newsletters. And one of the nice things that I noticed about the welcome email from the Washington Post is that when I signed up for each for a bunch of different newsletters, I got different welcome emails, each with the type of the writer or editor's name and a customized welcome email. Even though the. The main bit, the main call to action, was the same for everyone, which is they want to make sure that the email shows up in your inbox, and please copy and paste the email in your address book. So, like, the bottom part is all the same, but even then, it's kind of phrased differently. And aside from that, like, hey, listen, they're all very different.
Yeah, this is Steve, and this is a really great graphic collection of these newsletters you put here. What jumps out at me immediately is that you talked about being personal at the top of each of these, there's a photo of each person. The newsletters I've written in the past tend to tuck the profile picture at the bottom, much less personal. These. These put the person writing the newsletter right at the Very top of each one.
Yeah, I noticed that as well. Yeah, I love it. I changed our newsletter right away.
Yeah, it's kind of like an author byline at the top of an article, right?
Yeah.
It does look like actual newspaper. Washington Post article with the byline right up there.
Yeah. So I think this concept can extend to the newsletter itself. Obviously, this is just a welcome email, but if you think about it, most newsletters, even if they're email digest, they have like a introduction or editor's note at the top. And I think don't be afraid to go really deep into whatever it is you want because you're building a relationship with your audience. I think one of these even talked about cats. I don't remember which one, but yeah, like, you know, feel free to talk about your cats. So that's kind of the first one, big thing. The second one is.
That's great.
Thank you.
Yeah. The second one is don't be afraid to ask for things. So a lot of publishers, like, you know, there's a lot of giving involved. Like, here's the best articles of the week. Here's something funny I've seen. Here's, you know, so and so and so on, and people are kind of scared to ask. There are newsletter subscribers to join their memberships, to subscribe to things, to buy things, and I think if it's done properly, don't be afraid to ask. And so this is a newsletter from Men's Health, and if you see the moment you join it, they immediately ask you to join Men's Health mvp. I don't even know what that is, but I really liked the way that they did it. It wasn't like a hard sell. It was more, you know, the title is a friendly hello from the editor in chief, which again, goes back to the personalization with the name and his signature. And it's really just asking them to. Asking you to join their community. And it's selling immediately and, you know, explaining why you should buy it. You know, all the benefits, expert advice, useful tips. And I bet this email, because it's so simple and it's so clear and it's so friendly. I bet this email converts like crazy.
It's really short, isn't it?
Yeah. Yeah, it is.
It's four sentences long. Maybe. Maybe three.
Yeah. If it was me, I even improved the copy a little bit because it's not that clear what expert advice or useful tips or insider info is. But even without doing that, I bet this converts like that. Yeah. So I kind of suggest other people to do that. Like, a lot of publishers are sending subscriptions, and a lot of the time it's just this kind of dry, dull box asking you to subscribe or become a member for $1 or, you know, that sort of thing. But there are a lot of different ways that you can do it. And sometimes being more direct and being more personal can really help.
Yeah, having, having a, this is a free newsletter, maybe a free registration, but it's free. And so having a call to up, you know, upgrade to join for the paid product is, is critical. And you know, I'd say if, if you're listening and you're running any kind of a free newsletter or free registration, you really have two lists by definition. You have your, your free list, which is always promoting the upgrade, and then the, the paid or premium newsletter, which has no content about upgrades and just, you know, member subscriber benefits.
Yeah, but even the paid newsletter, right. There's always stuff that you can, you know, assuming you've got a new product or you've got a new promotion going on, you can, you can like, you know, don't be afraid to mention that to your subscribers. And because they're already paid members, they're even more likely to purchase something from you and want to support you.
Absolutely.
Okay, the next one, I think this one is kind of like the thing that not enough people do and potentially not enough people know about, and that's kind of appreciating and shouting out to your subscribers. So this is an example of newsletter I can excerpt from a newsletter. And in the excerpt itself, Sean shouts out to a specific reader and, you know, kind of screenshots a testimonial from a reader and kind of thanks him for liking his book. And I think this sort of thing is really nice because it's really nice for a couple of things, right? So as a subscriber, if I read that, I'm like, firstly, I realize there's this book. And then you have the social proof of people are liking this book enough to publish it on Twitter. And as the reader, you feel really, if you're Jacob, the person who did this, you'll feel really good because you've now gotten a shout out in the newsletter that you like. And also as a subscriber that didn't get the shout out, now I would want to, I feel more inclined to making such shoutouts on Twitter or even just replying to an email because then maybe Sean might mention me in his next newsletter. I don't know if I kind of said that In a very complicated way. But basically shout out your readers. It's always really nice. Another person who does this really well is Ann Henley. Is that how we say her last name? She's like a really prolific newsletter writer and she always encourages people to tweet about her. I mean, yeah, tweet about her newsletter and also reply to her emails. And whenever you do that, she always mentions a bunch of readers in her following emails. And yeah, it's just kind of like a nice touch and it makes newsletters which otherwise feel quite one way, quite broadcasty feel more of like a relationship.
Yeah, that is a very fundamental difference. You had the first slide at the beginning comparing newsletters to being different from social media. It's a very one way medium most of the time. And this seems like a solution to that, at least to make it a little more two way.
Maybe this is a question for later, but how do you get readers of newsletters to reply to newsletters?
I mean that, that ask them. That's how I would say it.
I, I feel, I feel like, you know, when we get asked a question, like we run our help desk people, someone will ask a question. It's great. Oh, so a question came in. Sometimes they're really interesting questions, but it feels like the newsletter should be the, really the trigger for that in a way where, where. And maybe we're just doing something wrong.
We've always had a fairly good number of people replying directly to the newsletter and so when we. Someone else. I have to go through the spam filter to make sure none of them have been caught. The people are on the phone, they get the newsletter. Oh, I have a question. Something about published press was on my mind. Reply. It's a fairly easy way to get in touch with you. It is if you don't use a no reply at email address.
Absolutely not.
It sounds like you want to see something.
Yeah, I was saying you could also seed it. Like you can just put a response in the newsletter and make that normal and then people can see as they're reading it. Oh, you take responses and sometimes publish them. Like if you fake it almost the first couple of times, just reach out to friends. Like, hey, could you like send me a tweet that we could embed as a thing to do here? Maybe a little underhanded, but if you want to jump start that process, it's one way of doing it.
Yeah, that's an awesome suggestion. Yeah. I think creating every newsletter is like a microcosm. It's like a little ecosystem and so it's important to nurture and create the culture around your newsletter and how you want your subscribers to interact with it. And so, yeah, I guess, like, in lieu of. Or if you have a relatively new newsletter and you need to jumpstart it in a way, then I think Stuart's suggestion of seeding initial ideas to kind of get the relationships going in a certain direction is, yeah, really great way to do it.
Yeah, I like that. I think we've been too, like, sort of feature oriented. We do case studies, but it's not like it's not really personal. I mean, to your point early, it's not. I think it's more corporate. That's still a word.
Is that the wrong. Leslie, you see a lot more of these newsletters than we do. You tend to recommend people against the corporate approach and to go for much more of the personal kind of.
Yeah, I mean, if the Washington Post can go personal, I don't see why we can't.
Right. Yeah.
Yeah. That was part of why I wanted to start off that, you know, kick things off with the Washington Post, because I knew that that question would come up right away. Like, people are going to be, you know, oh, it's too big. We can't do it. But nope, yes, you can.
Yeah, well, it's very human. Right. We connect with people.
Yeah. The other one that I wanted to mention, I've just forgotten his name. The astrophysicist Neil DeGrasse Tyson. So he has a podcast that I really like, and he, for whatever reason, also has a Patreon going. And during his podcast, he always shouts out his Patreon members. And also he has a Q and A at the end of each podcast. And he can't answer all the questions that he gets, obviously, so he always prioritizes the questions from Patreon members. And so I think, like, that's also a great way to approach it. You know, think of little perks of being a member, of being a subscriber, and kind of showing your subscribers that they get special treatment. Um, yeah. And again, Neil DeGrasse Tyson's a huge figure in the science world, and if he can shout out Patreon members, I don't see why we can't.
Yeah. Cool.
Yeah. All right, next one. Segmentation and multiple newsletters. So this I think most publishers are already doing, but for the few that aren't, I highly, highly recommend segmenting out your newsletters. It could be something as simple. So there are a couple of ways to do. Could be something as simple as a Weekly digest as one newsletter and then editorial newsletter. So like, that's one pretty easy way to do it. And then you really only spend time writing the editorial and the email digest is quick to put together. Another way to do it is to just split up your categories into various newsletters. Obviously, that quickly means that you have five or 10, 20 newsletters. So then it's just about prioritizing which categories you are best at or have the most traffic and just start out with that. But definitely for sure, if you're not already doing it, this is a great way to build a relationship with the people who care about specific topics. And that way you can go much deeper. So the idea here is always that you want to go a lot deeper than you otherwise can in any other medium. And so if, for example, you have this is PC magazine, right? And they've got security watch. So if you've got huge security nerds out there who only want to receive a newsletter purely with 10 articles on security, now you can. And they'll be overjoyed when they read an editorial by the security editor, which would be completely incomprehensible to someone like me. And you can go as deep as you possibly want and they would love it. And that's kind of like the way to think and approach this. Whatever you can do to go deeper is something that you should definitely try.
You haven't done much shouting out for your product, Lesley, so let me give you a chance. Is this something you can do with newsletter glue, which is your plugin? Can you present a set of different newsletter alternatives to your readers?
Uh, it's not, but it's something that's highly requested and we are planning to build it out this year. So this is, this is called an email preference center.
I'll. Let me set. Let me just step this down a little bit because this is, this is a fairly advanced strategy. The publishers we work with, believe it or not, occasionally run into a publisher is not publishing a newsletter. And it, it's, it's. I know that's terrifying.
Publishers with a lot of content, but they still don't publish newsletter.
That's right. It's amazing. It's just absolutely amazing. And then they, then they finally set up a free registration, which everyone should, if you're charging for paid. And then they're then also in their newsletter blows up, right? They're just, they're just pouring it. And I always, by the way, Leslie, I always recommend newsletter glue because you just save so much time, you know, just publish once publishers, boom. Push it out and off you go anyway. And the publishers that we deal with mostly typically have one newsletter like a main newsletter and they'll put all their content in it for better or for worse. And a lot of what I hear is I don't have time. It is a lot of work to put a newsletter together. And so the time thing, yes, newsletter glue is a great solution, but it's what I tend to focus on from the subscription side is to, is to create two newsletters. Create that free. The, make sure you have the. Keep the free newsletter, right? Like what they currently have is typically the free newsletter that, that you know, the pop up box on the website or whatever, whatever. However, they're annoying their, their readership to get those signups, which is a whole separate discussion. But anyway. And then what. Lately this is, this is, you know, fairly lately I've been really pushing and it's working well because we just see this with our, our publisher base is creating the premium newsletter, right? So now you have two newsletters. You have your free newsletter that's got all the promotional upgrade information like what Men's Health you showed earlier and then they have the premium newsletter. And the premium newsletter is just, could be as simple as not having ads because it's going to paid subscribers or it can have like another simple thing is full text, right? So you get the newsletter, it's full text. You don't have to click anywhere or log in anywhere and off you go. So you know, I see this and I, and I see a PC magazine. I see, okay, this is a big publisher and this is great and we do have publishers that, that, that have several opt ins and the opt ins totally work like, like I don't know, it's 80% or more. People absolutely opt into the categories that they want. But I just wanted to kind of bring it down to like you know, the fact that some publishers don't even have a newsletter, right. Like still they're coming from the, they're coming from the print world or I don't know what world, but they, and they're publishing on the web and they're leaning on that and they haven't really understood how important the newsletter is to their publication. Cause if we look at again a whole separate topic, but if we look at subscriber data, the newsletter is usually the number one source of paid subscriptions. Sometimes number two, usually number one. And it's getting more and more important because it's first party data, right? It's what they control.
Pete, could you flesh that out a little. So once you sign someone up for the free newsletter, that is either the first or second most common way that people become paid subscribers. What are the other kind of COVID channels up there?
So some publishers will report Facebook is a bit. Is a huge channel news publishers, although recently we've seen Facebook actually declining pretty substantially as far as traffic goes. And then Google, you know, just, just general Google search, that's, that's can be very, very dominant. And then the rest sort of fades away. Yeah, so I'd say Google is more dominant than Facebook, but Facebook used to be more dominant than Google. It's, it's a bit of a battle going on, but the newsletter is always there. And it's the. It. Like you said, it's the personal connection and it's the, it's your. You have total control over it and it's driving it. You know, it, it's, it's. It's the number one direct marketing tool that publishers have. You are sending something into someone's inbox which says, hey, I'm here. Remember me? This is my brand. This is what's going on. Cool stuff. Click on the article, go back to the website, like over and over and over and over again. And it's that repetition that eventually causes somebody to say, you know what? I want full access because I keep getting stopped by the paywall.
Leslie, Stuart, do you guys get any insight into how important the newsletters are to, to your customers in terms of driving revenue?
Yeah, they're important very much for the same reason. Like Pete was saying, like, the way in the kind of mental model of things is like, people are coming to these sites because they're trying to answer a question. So they have searched for something and then something has come up. Like, all right, that's a brand exposure. Unless you are then doing some kind of like, retargeting through Facebook and Google to kind of have that secondary exposure. The best way that you can do that is getting someone into that email list as quickly as possible so that they can have that second, third, fourth, fifth, sixth, so you can show the value in your content, the value in your journalism to then get that paid upgrade without having that or some other means of dealing with that. So other things are stickier podcasts, but those are hard to get people to jump in and sign up on. Newsletter is easy because you can make it a problem for them to be like, you want to read this piece of content? You have to join this newsletter. Please continue. And that's generally how it works. We see a Lot of our publishers doing very leaky paywall approaches. Three in the month, they're free. The next two, you have to be on the page newsletter and then some content will also be marked available for newsletter and then after that it's into the paid subscription. But that paid newsletter is the actually the primary touch point through the whole conversion process, not the website.
Very wise words.
That's awesome. What about you, Leslie?
Yeah, I don't think I have anything else to add, Steve. I nailed it.
Yep. Cool. I'm going to listen to that again when I rewind.
Steve, it looks like you have something else you want to see.
Oh, the thought was forming, I guess I was trying to think back to how our customers interact with the newsletter. And there's an audience of people who are active on Facebook and will be on our Facebook group and posting questions all the time. And the newsletters that we send out reach a slightly different audience. I think perhaps people who are maybe a little. They don't have the time to be on Facebook. They're all less engaged on a daily basis. But once a week, once a month, this drops in there in their inbox and they appreciate it.
I think that's an interesting thought too, is that it's not a one size fits all problem. Like as a product business, you're going to treat that newsletter differently because some people are, people are come. People are looking for a problem, solution to a problem. They're coming to websites like, oh, this whole thing is the solution to the problem. The content is the solution problem. And then you are upselling on that. I think you would approach them in different ways.
Yeah, direct marketing, it's. You get to directly touch somebody regularly. It's. I mean it's powerful and that social media can't, can't really touch that.
Do you guys. You'll work mostly with. I know Pete, you send out a regular newsletter, but you mainly are working with clients who are sending out newsletters. Do you get them on schedules? Is that an important part of building the trust in the community is doing them daily, weekly, monthly? They're very predictable. Schedule.
Yeah, most of them are coming in with schedules. They do have their routines. You know, it's a, it's a daily depends on, you know, we deal with daily newspapers, weeklies, magazines, niche publishers, all kinds. They all have totally different schedules, but they have their schedule and that's really important. A lot of them do, do complain about the time it takes. So that's what we talk about like automation. Right. Like how do you, how do you publish once in WordPress and then have that automatically fire out, which I know newsletter Glue can absolutely help with and, or RSS to email with like, like a mailchimp can, can do that. And it's split. I find some publishers are very much, they want to, they want to craft their, their newsletters very very brand sort of centric. And some publishers are absolutely. Couldn't care less. They're like, just, just get it out. Like if I, if I don't have to get it out and someone, some machine can send it out for me. Great.
It's where they completely would not have that approach to publishing on their website, to publishing the, the articles. But for the newsletters.
Yeah, yeah. And, and, and they, they, you know, I think they're getting more savvy about it. I think that's, I think they're starting to realize that. I had somebody tell me this is not very long ago said we had this discussion about newsletters and, and that he was all on Facebook for years and years. It was a, was a sports publisher in Ireland or something. A rugby rugby or something. And he said, he said, you know, I, I can't. I just wish 2 years ago I had really focused on my newsletter like that. I think that, I think publishers are starting to feel like, oh, you know what? I've kind of been missing the game here. You know, just. Which is interesting.
Yeah. Because newsletters is where curation really, you really like the subscribers really benefit and feel the curation. And I think like you said, it's a missed opportunity because even when you put in lots of effort to decide which articles to publish, what to write about and stuff like that, like when a visitor just lands on your site from SEO, they're not really thinking about any of that. They're just landing on the specific article. And then maybe if you're lucky, they might click on your homepage and get blasted with easily 30 articles without even scrolling. And so when the best, you know, this week's best articles or this week's most clicked articles as a newsletter gets sent to them, I think there's, there's a real benefit there that it's unfortunate if people aren't doing that.
We have, I'll tell a little story. We have a local news publisher's friend of mine, it's Daybreak News in the Upper Valley in New Hampshire here. And what he does, which I know some publishers are starting to do, but you know, he's an independent, he's a journalist and he just combs, you know, Reddit and YouTube and the local news sites and the college websites and, and puts together a daily morning email that's just, it's just curation. He doesn't really write. He occasionally will write original content, but his, he puts the link in to the website as the title, and then he writes a very short summary of what it's about. And then you can scan it every morning and get huge value from knowing what's going on in our community. It's the one, one of the few things I read, you know, every morning, very religiously as far as local happenings and, and it works. And his subscriber base, in a year, he hit almost 10,000 subscribers in one year, in his first year when he came out. Because. And the big newspaper here does not do that. And they, I think it was a missed opportunity for them. And he's, you know, we're. We're in New Hampshire. We're in the, we're like in the mountains in New Hampshire. We're not in a hugely populous area. Our, Our whole, like, readership, which is like 30 towns, is maybe 80,000 people or something like that. And he's managed to bust through 10,000 subscribers. And, you know, that was, that was a year ago. So.
So he's basically taking Leslie's advice to the max in terms of curation. He's popping on, on the Reddit board, on the local newspaper, and kind of picking and choosing the best from all of that. So that someone who's busy doesn't have to go and read it. Doesn't have to exactly go on his website.
Huge time saver. You know, what's going on. You don't have to, you don't have to pay attention to social channels. Yeah. And that's, and that time, that's. That's the world we live in. Right. If something can save us time, it's worth more than money in some cases. So.
Yeah. And Steve, you mentioned about publishing schedule, so I just wanted to talk really quickly about that. So it doesn't really matter if you publish daily. Weekly. Monthly is not so good. Twice monthly is better. And so none of those schedules really matter. What matters is that you stick to it and you stick to it over a very, very long time. So the newsletter that's published, let's even go monthly. Right. So the newsletter that's published monthly for 10 years is going to beat the newsletter that's published daily for a month. And then that person burns out. And so just kind of committing and sticking with it, whatever the schedule you choose. I think that's the most important part.
Sorry, go on.
No, you go, you go. I was just going to say like if you look at PC magazine you can see that they've got a bunch of different ones, right. So they've got daily here, they've got weekly here and so forth. So it doesn't really matter what there isn't a best publishing schedule.
Yeah, I just to agree with that and I think you can have all of them like you might have like your daily firehose like someone because you're going to have different kinds of readers that want different things. You're going to get folks that want every post as soon as it's like and they live inside of their email and that how they want to consume it. You're going to have folk who want a daily digest of everything. A folk who want a digest of one particular category which seems to be very much how Easy Magazine or here works. But then you're going to get folks who are going to want like a monthly digestive in review. We had a publisher that had a weekly newsletter of just kind of stuff that went out and that was fine. They brought on a columnist and gave him his own newsletter. So they had this kind of like group thing that went out from everything that was on the site. Then this like one guy, highly curated like here's what I effectively an article that would have been on the site but only to his interested parties. He was a former politician in the UK and then that led to a kind of like looking back like what was popular this month on our on our site and then a follow up one of like here's a shortcut to everything that's in our print magazine so you can click through directly onto for just for print subscribers. So there's all kinds of different ways. They had a daily, a weekly one, a monthly one bimonthly whenever you don't need to have one. And if you get smart with the data you can tailor it to an individual user like yeah, I want everything right at the time. I want everything once a day, want everything once a week, want everything from this category once a week. But it's how do you arrange that and do all those segmentations? Because at a certain point you could be generating an individual email for each user in the database which is doable like it's cheap to do but you can if that's what you want to go down.
Yeah, that's great.
Stuart, what does the tech stack or the organizational stack look like to manage something of that size and that complexity? You have like two or three people managing the, managing the emails. Plus do you have an off the shelf platform?
Like you would be surprised how much you can get away with in mailchimp. You know, like it is very good at what it does because in their case they're just consuming an RSS feed of everything that's coming through the site. You can go further down that road. So if you want to do more of that kind of like here's a chance that this user is going to end up having an individual email. You could take the basis of newsletter glue and kind of use that to do your generation, but you're passing in specific data to it. You also aren't moving the subscription where that is managed away from something like mailchimp into your own database and then sending them directly through like Mandrel or one of the other transactional meal platforms. Because they're not a big batch. They are like, this is this user's email and this is this user's email. But you can set them up on a cron to run it like, okay, for this user, here's what they want. Off you go.
Yeah, once you get, once you get the logged in user, you get a lot of great data and that's, that's where that free registration is just so critical.
I would say that most, most newsletters, like, unless you have a couple million or more subscribers, you probably, it's not really worth doing the personalization on the level of per user. Like per 5 to 10 users. It's, you know, get your, get your first 5 to 10 newsletter segmentations out first and then in the distant future you can go crazy with the programmatic newsletters.
Lesley, what do you see people using for their stack? Are they mostly using mailchimp or using Mandrill or one of the common, one of the common delivery providers.
So Mandrill is a transactional email provider that belongs to mailchimp. So they're not using that. A surprising number are using mailchimp actually. So mailchimp is popular. Activecampaign, I would say is second most popular. And then you have actually a bunch of email service providers that I never even heard of until I started doing this. So Piano is an example of one of them. They are very into the programmatic stuff and I believe they only work with really, really large publishers. Yeah.
As a platform or Piano.
Yeah, they're going after the really big, big publishers.
Yeah, yeah. And it's funny because like I think I only heard of them last year and by then I'd already Been working in newsletters for a while, and it was kind of cool. Like, every time I think I've reached, you know, the top or, like, I know all the products out there, it's like, nope, there's a whole other level that I don't even know about.
There's a lot, especially when you get into print publishers, then they got all sorts of special needs.
Yeah.
Yeah. I also wanted to mention briefly about the automated newsletters or automatic newsletters in rss, because we've tiptoed around that a little bit, and it's just a great way to get multiple newsletters up and running quickly. So rss, basically, you can set this up in almost any common email service provider. Basically, you just kind of pick the RSS feed from the category or the tag or whatever it is that you want to have your newsletter about be about, and plunk it into a template and click Schedule or Send, and it just kind of sends out the articles within that filter on a schedule. So that's a really common way to very quickly start multiple newsletters, and it's a way that many, many publishers do. And, you know, if you don't have time and you just want to get going, then I really, really recommend that. Another way which we have NewsletterGlue has, is automated emails, and it works very similarly with one difference, and that's we allow you to schedule the creation of drafts so that you can pick which articles within the category that you want. And this is useful because with RSS, you don't like. Let's say you've published 10. So let's say we have PC Magazine, right? And we've published 10 articles on Apple this week. And we don't want all 10 to go out in the newsletter because not all of them. There are varying levels of quality. So we want 8 out of the 10. If you set up an RSS newsletter, there's no way to curate that all 10 are going out. And worse still, if there was an update and you don't even, and there was a mistake, there's no way to correct that mistake. That mistake is going to go up in your RSS newsletter. What we allow publishers to do is create the draft so you get 99% of the way there and then send a test email, do your curation, write an intro if you want, and then after that send the email out. So you get all of the benefits of the automatic creation but none of the stress around, oh, I didn't want this email to go out, or I don't want this article to go out or what's in this week's email? I don't even know. Was this broken? No idea.
That's a cool idea.
Thanks. Yeah. And likewise, once you've gotten it all set up, then you don't have to have a full time writer every week managing 10 different newsletters. It's 99% automated. And this gets you, lets you have your cake and eat it too, I guess. You know, you get the multiple different segmented newsletters, you get the very, very specific, you get to build very specific relationships with all the different types of subscribers. And it doesn't take a whole lot of time.
How do you batch the newsletters? Like how do you batch the articles, not the newsletters?
What, what do you mean by that?
Well, let's say I'm. Let's say I'm writing 10 articles a day. I'm a news, local news publisher and I have 10 articles that I publish and I want to get, I want to automate that as much as possible. But, and like you said, I, I want, maybe I want eight of those articles to go out just to, just for argument's sake. So how, how do I actually get that done? Do I send eight in individual articles out? You know what I mean?
I would do like a daily recap. So kind of similar to what PCMAG has over here. Like what's new now? Your daily dose of latest tech stories. So I do something like that in the case of a local newspaper, maybe I do yesterday's top stories or something like that, or today's top stories and you send it out in the evening. And so with us you can set up a template. It's just like all articles published in the last 24 hours. And so you've got your 10 articles there and the draft is already created and you just go in and you click to hide the ones that you don't want to have show up.
Nice.
And yeah, that's it. So it's about clicking once or twice to hide the ones that you don't want and you're ready to publish the hide checkbox.
Great, that sounds awesome. Thanks for that. And let me just, just for anybody listening who doesn't know what RSS to email is. So mailchimp, as an example, as an email service provider, it will scan your website a few times a day. I don't know what their schedule is. And it will look for new content. And if you set up the RSST email service, it will just pull that content into the template that you set up in mailchimp but with newsletter glue, it sounds like you have way more control over this process. So there you go.
Yeah, but I recommend both. You know, if you have the time, just set it up and don't worry about it. And your list will benefit from it for sure. All right, let's move on. So the next one is about quality over quantity of subs. So something you kind of have to accept about newsletters is that you're always going to have fewer newsletter subscribers than you will Twitter followers, Facebook group members, website visitors, and so forth. And it's just the nature of it. It's, you know, going back to my original slide about discovery versus building relationships. You know, if you walk down the street on any given day, you probably walk past hundreds if not thousands of people. And those are all people that you kind of have exposure to, which is similar to kind of walking past someone on Twitter. In contrast, the newsletters are people that are your friends, people that have actively opted into building a relationship with you. And so you're always just going to have much fewer friends than you will random passersby. And I think that's kind of a good heuristic or a good way to think about it. So don't worry too much if the number of email subscribers you have is way lower than what you're getting on other marketing platforms or distribution platforms. And as an example, here's a little screenshot from Twitter. It's a conversation. The first person's asking, how many email subscribers do you think it takes to make it comfortable full time living? And the second person, Jason Resnick, who works a lot in the email space, says, surprising, it's not as many as you'd think. I've seen lists make six fingers, six figures from 200 subscribers. And I think this is something really important to keep in mind because if you've done a good job with all the other stuff we've mentioned about segmenting, going deep, being personal, then yeah, for sure you can make six figures from 200 subscribers. You know, if you think back to the Security magazine Security newsletter from PC magazine, if you've created a super specific security course and you sell it to the security subscribers, they're going to buy it because you know, they already love everything to do with security. Whereas if you have a million subscribers and they're all kind of generic, you know, we subscribe because of a contest or you know, some, some other random thing, that million subscriber list might not get you as many conversions for your security cost as your super specific Security newsletter. And yeah, that's something important to take note of.
Yeah, financial publishers fall into the same boat. We have some and they charge a lot of money for their newsletters.
And I bet they have really few subscribers, right?
Oh, there's so many niches in finance too, depending on industry. Yeah, yeah.
You're getting in the realm of thousands of dollars a year for a subscription.
At that point, right?
That's right. Can be hundreds or thousands. Yeah.
So a question I guess for all three of you in terms of quantity versus quality. How do you talk to your clients about getting subscribers? Is it boxes at the end of stories? Is it pop up boxes? I presume you're not making them run dumb raffle competitions where you have to enter your email address to win an iPad. What are the strategies you're recommending to people to get more quality subscribers?
Oh, I'd love to answer that one.
Stuart looks like he has good answers too.
Well, I mean it's simple from my perspective, but it's hard to swallow and do it. And that's you leak a few articles each month and then ask for a free registration. But the real answer is, is you leak one article a month, you really tighten down the paywall so that you know, okay, one article, let's Google index everything and let's that you know any single article be shared in social media to different folks. Fine. But then you can make the promise of okay, you're, you're. If you want to read this next article, which is the motivation when somebody is on an article and it's locked down, it says hey, read this article for free. You know, the language is important. Yeah, that's what I want. I want to read this article for free. So they register, they're going to get the newsletter. Maybe they get one or two or three extra articles per month for doing that and you sell those benefits and now you have your, now you have the startup of a relationship versus you know, the pop up box for the, you know, the zombie. You get some zombie subscribers when you pop in a boxes that at people and yeah, so if you have a.
Tighter paywall that gives you then more stuff to perhaps give away as an incentive for the free subscribers and then gives you more to upsell. So the tighter the paywall, the more freebies, the more goodies you have to work with.
That's right. Yeah, you can get people to register sooner in the path. I mean the, if you look at Google Analytics, right, you get one to two article views per visit on average. So if you're, if you set, if the setting is one, you're gonna jump your registration rate by a ton. For all those folks that are going to two. And some of those convert, it's amazing when we switch on a new, a new publisher that their free registrations just, they just load up daily. You know, people are pouring in with the tight, with that tight setup. And then there's a percentage of those that convert to paid. But those are, you know, that's the start of the relationship now. Now you have these folks that have you, have you introduced a little piece of friction? Because at the very least, you're collecting an email address and asking for a password, right? So it's, it's different from. And you're, and you're, you're, you're giving a promise. And you look at the New York Times, they've been experimenting with this for, for a decade, over a decade now. And you know, you go there, they let you read one article, they make you register, you get more, you get a few more. That's their language, a few more. You know, pay attention to what they're doing. It's amazing.
I was on our local newspaper site this morning and they locked down a lot of articles and immediately it's a request to join to pay. Your recommendation is typaywall. First up, the first option should be to join as a free newsletter subscriber. So type payroll, sign up for free, and then upsell.
Yeah. So the biggest, when I take publishers through this, the biggest opportunity are the cat. This I call super casual readers. So you have, it's like a bell curve, right? Like the front of the bell curve is your, your big fans, they pay right away. So no matter what you do, doesn't matter how you screw up your paywall, you'll get those, those fans right away. They'll pay you. And then you have the folks on the other side, the right side of the bell curve, they'll never pay you. They're, they're just, for whatever reason, they're just flybys. They're sort of interested. And then everybody in the middle, these are people that are interested in your content. They like you, they like what you're doing. They're just not ready to pay. Right? So that's the opportunity. All those. And how do you, how do you get them to pay? Well, they're not going to pay now. They're just not ready to pay now for whatever reason. But they may pay you in four months, right? So you have to get that email. Like you have to get them on your newsletter and then it's, and then it's building the relationship you're getting. You're sending the content, you're sending the special things, the curation, whatever it is. And then at some point when they keep seeing the upgrade message because you're pushing them back to the website to refresh, read more content and they use up their free allotment because you've been a nice publisher giving them some free stuff in the newsletter, they finally get tired of that seeing the upgrade message and they say oh, okay, I'm gonna, I'm gonna pay.
Leslie Stuart, same question for you guys. Do you have ways in which you recommend people get quality subscribers?
Yeah, I'm gonna have to jump off. I've got another call in a minute. So I'll just like info dump I guess very much the same. Like put it all behind a registration wall. Even if you never charge for a payment. Like put everything behind that registration wall. Like 1, 2, 3 posts. Make it very clear on the post like you are on reading 1 of X free articles this month so that it's not a surprise when it comes up. Move away from thinking of things as pages. I've seen something really effective recently where once you load in a post post that you are reading it basically infinitely scrolls. So if you keep scrolling down you're reading the next post in that category and someone if the posts are well related can very quickly eat through their 332343 that month. Then when you get to that registration, don't make it necessarily an email and password like have that be an option. But a one click register with Google to remove the frictions that you are getting them into that email list is definitely the way to go. Things like ad blockers. If you have a thing that was like the text, like oh, you're using an ad blocker, like you're never going to turn it on, they're going to go away from the site, turn that into a subscription sign up. I've never seen that done but I'm dying for someone to let me do it. But yeah, that's kind of the stuff we look at. And then emphasize the benefits of personalization. You'll get more targeted email newsletter stuff available to you. You'll get like preemptive new access. So maybe they'll get the post an email an hour before it goes out on the site. Depending on the site. Obviously not going to work for breaking news, but if you've got like a high volume something that you know like a financial news site, someone might Want information about something beforehand. Like, that's great ways to kind of push that. It's comes back to all marketing. What is the benefit rather than the feature? The feature is you're a member and I. But what is. What benefits can you make up that justify that? Cool. Right. I'm really sorry, but I'm going to have to go. Got another call to be on, but it's a pleasure.
Thanks, Stuart.
Yeah, thanks very much.
Yeah, thanks. Thanks for dropping by. See you.
Yeah. We're seeing trends in hiding ads. So if you. You pay for a subscription. Some publishers are trying just to hide ads, but you're paying for content and you pay extra. So like a premium plus subscription and it hides the ads as well. There's a Swedish news publisher, there are few, but the one I can think of is pretty striking because they shared their data is they have a. They have a premium subscription for their content and then you can choose to select the highest level which hides the ads as well. And you know, they get 10% of their subscriber base choosing the higher option. And the higher option is 40% more expensive than the. The main paid option. So you can kind of see where we're at in society in terms of how we feel about ads on websites.
So.
Interesting stuff.
Yeah. One thing I also wanted to mention, which we don't. I'm not sure if I've actually seen any publishers do it, but it's really common in the newsletter world is cross promotion. And so I'll talk about what people in the very specific newsletter world do and how I think publishers could adapt that strategy. So in the newsletter world, basically you can give shout outs to other newsletter writers or give shout outs to the newsletters itself or articles and so forth. And it's a cross promotion. So I shout Steve and Pete's newsletter out and then in their newsletter they mention mine and so on and so forth. And the reason why this works so well is because you already know you've already selected for people who are into newsletters because not everyone is right. Like as we talked about earlier, there could be people who don't ever look at the email and they are really big on Facebook groups or Twitter and so on and so forth. And so once you've self selected for people who like email already and assuming you've done decent job at curating who you're cross promoting with, that strategy has proven really, really successful for multiple newsletter writers to grow their subscriber base over time. So the problem that publishers run into is that not all Publishers want to shut out other publishers. Right. Either due to brand issues or editorial differences and a whole myriad of other things. But I think there are ways to get around that. And also it might be awkward if you're just kind of doing an email digest and it's weird to specifically shout out a different publication. So a couple of ways that I could see this working for publishers is having like a external curated article section. So you've got your, the section for your own articles. And then you could also do like a separate section called around the Web or something similar. And then you can list other articles which, which are selected from the publication that you're doing the deal with and that publication might already know. Okay, these, these articles have a good track record of converting people to newsletter subscribers. And so like on both sides you could do that and then you can cross promote the articles and then get the newsletter subscribers that way. Another way is simply cross promoting. And so this is where having multiple newsletters is important. Right. So simply cross promoting your own newsletters because if you've got 10 or 20 across different categories and segments and stuff like that, there are probably going to be a lot of people who like, who are interested in both or more. So just kind of periodically shouting out your own newsletters, I think would be really powerful as well.
Yeah, no, I think that's great. If you're into curation, like our local daybreak newsletter, then you're almost always shouting out. But you're right, like local publishers tend not to do that. But I'd say niche publishers are probably more likely to do that and the world of niche publishing is exploding now. So. Yeah. Finding others in your same space that have interesting things to talk about.
Yeah, I think if it's interest based then you could. And that's kind of how a lot of newsletter writers, like, I wouldn't call them publishers, but newsletter writers work. Like if it's in the same space, then it'd be fine. Right. If you're, if you're a camping magazine, it would be totally fine to shout out a camping newsletter. And I don't think that would be awkward or strange.
Yeah, or RVs, you know, or micro trailers or whatever the niche is.
Yeah, for sure.
And I think it's good to look at it from a demographic point of view rather than a specific niche. So like, just because you're a camping magazine doesn't mean that you're only limited to other camping or RVs or firestarter lumberjack newsletters. Like you could just broaden your target Audience to any newsletters for people who live in more outdoor areas, or dare I say, men between the ages of 20 and 40 or something like that?
Yeah, yeah, yeah, absolutely. Yeah. Play. Play nice with others. That's that. It works. Lifelong lesson, right?
Hey, we. We do a. At least one newsletter a month that is kind of like. Like Pete describes. It's in a niche and we basically just summarize stuff other people are doing in that niche. And you'd be surprised how many people will sign up just so they can see if they're included and also try and get included. It's a good way to build community.
Yeah. And I think that's a great way to have quality over quantity of subs as well. Because, you know, everyone who signs up for that is going to be, you know, someone who's actually interested and isn't there because you've run a contest for a free iPad.
Yeah. They're there because they're begging for inclusion or they've been included in the past and they're happy about it. And the curated newsletter is the one thing that people mention when they talk about this particular business. Now that, oh, you're the guys that do the monthly roundup. It's a good approach.
I need to go look up this newsletter. I'm not sure I get it.
Oh, this is in another software niche outside of WordPress.
Oh, okay. All right.
But it might be a good. I mean, that's what basically post status does. We. We started talking through the post status WordPress group, and there's a bunch of these newsletters in WordPress, right. That basically take the created approach. And a lot of plugin developers or theme developers will subscribe just to see if they can get a mention in that week's newsletter.
Yeah, well, WP Mayor does. Does something related, right? I mean, they, they do a lot of paid reviews. I mean, they do regular reviews and they do paid reviews and they've built a pretty big community doing that. And it works.
Yeah. All right. Last, last one and then I think we're done. So this one is simple. Treat your biggest fans. So your new sentence subscribers are always going to be your biggest fans. They're going to be more into whatever content you're making than your Twitter following, your Facebook page followers, your website visitors, and so on. So treat your biggest fans right. And there are so many, literally a million creative ways that you can do this and that you can have fun with this. So I don't think I can go through some examples, but I think the big takeaway is to do it and to have fun with it and see what works for you. So the easiest one is just to offer them a discount or a unique offer. You know, here's a 10% discount code because you're a newsletter subscriber. Or it could also be recency time based, meaning your newsletter subscribers get your articles or get sales open to them earlier than other people. So it doesn't even have to be that you affect your bottom line by offering your newsletter subscribers a bigger discount. It can just be they get to it first, they can get a freebie that you've created for them, a lead magnet or a guide or something like that. Only they are getting that no one else is getting and so on. So I think again, like I said, there are so many ways to do this and what's important is just to have fun with it and to do it to begin with.
Yeah, having a, if something is premium, like I always go from like free to premium newsletters because that's the world we live in. But you said time, like that's really important. We have plenty of news publishers that, you know, you pay for a subscription, you get, you get, you get the, you get early content, you get content delivered early, you get full text. Obviously you don't get any ads. And that's enough. I mean, that's plenty. Pick one.
Right.
It's special. That's special.
Right?
And, and, and value. That's, that's a, that's a big benefit. So, yeah, that's good.
So, Leslie, everything you've been saying today basically revolves around making it more, more personal. The newsletter subscribers are much further down the funnel than people that follow you on social media. For example, these subscribers have given you something. They've given their newsletter, their email newsletter, email address. They've given some trust. And to be a good newsletter writer, you need to be giving more of yourself than you would do to people on social media or other venues.
Yeah, I mean, that's kind of the starting premise of what I wanted to talk about today. Right. So like there's discovery and then there's relationships. And because newsletter sits squarely in the relationship side of things, there are a whole bunch of things that you can do for your newsletter subscribers that might actually come across weird or wrong or might even offend people on social media because they're at a different stage. And so, you know, being aware of the fact that it's discovery versus relationships and new statistics and relationships allows you to play with things in a very different way. And it's Important to know that and have that as your starting point.
What a great way to wrap it up. Yeah.
Awesome. Thanks, Leslie. Pete. Leslie, do you guys have newsletters that you send out for. For Leaky Paywall and for Newsletter Glue?
Yes, we do. Yep. LeakyPayWall.com would be a place to go for that. And we tend to focus on things that publishers are doing with their paid subscriptions that are actually working to generate, you know, more subscribers.
Oh, yeah, I get yours, Pete. And it's a lot of case studies.
Yep.
And, Leslie, ours is NewsletterGlue.com blog, and there'll be a form to sign up for our newsletter right on the top. And mine's actually slightly different, so I've kind of taken a more personal approach, and I have, like, an editorial at the start of each newsletter, and it just kind of talks about what we've worked on that month, and then the rest of it is our latest posts for the month. And, yeah, so it gets a bit. I try to make it a bit more personal.
I love it. I get it. I read it. It is personal. It's very nice. It's definitely your. Your tone of voice, and you feel a connection. It's good.
Also, the newsletter glue very much comes from. From Leslie rather than from Capital N Newsletter, Capital G Glue from the company. It very much comes in your voice and your. Your approach.
Yeah, that's. That's what I try to do, at least.
Yeah, I may have to steal that approach. Go more personal. I think that's my takeaway from this. You know, and we're. And we've been. We've been working. We're doing a rebrand right now. We've been working with a group of people, and the thing. The clear message is, you know, you know, get your. Get your personal connection out there. Make it personal. You know, really bring it. Bring it down. Make it human.
Make.
Make. Even though you're selling software, it's like your people behind the software. So connect, you know, as people connect, because that's what works.
What about you, Steve? Where can people hear about or subscribe to your newsletter?
I've just realized that we don't do a good job of collecting the newsletters on our product sites. In the past, they were overwhelmed with spam, and we took down the newsletter signup boxes. So generally, we. We've only been sending to people that have paid for our products. I need to fix that.
Yeah, we're in the same boat. After this webinar, I'm gonna rush to the website, figure out where to put the email sign up box.
Hey, that was why it's good to have a a session with Leslie. You come away with all these notes of things to do.
She's thinking, those two numbnuts, what are they doing?
Yeah, every time you send out a product update, you're going to get a bunch of conversions. So you've definitely been missing out.
That's funny. That's really funny.
Yeah, we send once a month to two people that have paid for us already, but we suddenly, we don't have a funnel in the newsletter. We just have people that are already in the funnel and have already paid us.
All right, well, let's wrap it up for today, shall we? That was a great first session. I think hopefully our listeners, whoever you are out there listening, think so too. We're open to suggestions. We're here to talk about all Things Publishing and WordPress. So if you have a specific topic you'd like us to tackle, a specific question, could be anything. Please reach out and let us know. And where can people reach out? That's the next question. Since we're just starting, this is going to go on YouTube, right? So there's some comments there.
Hey, we'll figure that out for next month.
Okay.
I think people can dm. We're all on the post status slack, so people can message us there. I'm on Twitter a lot and I'm at Leslie Pizza. L E S L E y. And my DMs are open so you can contact me there.
Before we sign off, Leslie, what's the origin of that Twitter handle?
Oh, I just, I just like playing around with top line domains and I found Pizza was available. Leslie Pizza. And so I just kind of branded myself as Leslie Pizza across the Internet.
Everybody loves pizza. That's awesome. I'm more on LinkedIn. Peter Erickson on LinkedIn, it's slash. Erickson is the. Is my URL, whatever that is on.
LinkedIn and Steve Burge on Twitter.
Awesome. All right, thanks, guys. We'll catch you next time.
Hey, thanks, Pete. Thanks.
See you guys.
See ya.
Thanks for listening to the Paywall podcast.
You can find us@paywallpodcast.com Be sure to.
Subscribe and your podcast player of choice and we'll see you next episode.





