Trust, Cadence, and Content: Rethinking the Publisher Drip Sequence

One publisher we looked at sends one email after you register, just one, and it's their highest converting outbound push, period. Another one sends 18 emails, an 18-email drip sequence that drives paid subscriber, uh, paid subscribers after every single one of those 18 emails goes out. Same goal, build subscriptions, totally different approaches. They're both doing it. So today we're going to figure out what these publishers actually know, what everyone else is missing. Um, and why most of the drip campaign best practices you read are— they're okay, but there's some, some nuggets here to pay attention to. We're also going to talk about local news and drips as well. And those three things will be the sort of customer profiles. Now, welcome, Tyler. Hi.

Hello. Hello.

Here we are, Paywall Podcast. Tyler from Newsletter Glue. I'm from LeakyPaywall, and we're going to— we're going to dive in.

Welcome to the Paywall Podcast, where we discuss paywalls and paywall strategies for news and magazine publishers. This episode of the Paywall Podcast is brought to you by LeakyPaywall. LeakyPaywall is the most flexible WordPress subscription platform. Find out more at leakypaywall.com. And now for today's episode.

Now, before we jump in, what I want to do is, is go through some of the research that I went through this morning in terms of drip campaigns. And there, there are some, some things sort of like general things that we need to— I thought it would be really important to kind of make sure we went over because they're sort of fundamental to making sure a drip sequence works. And then we'll jump into those 3 examples. Now, what is drip? Let's just get that out of the way. So I sign up for your newsletter, you're a publisher, I sign up for your newsletter, or maybe I go through the free registration, which is the, obviously the best way to do it. And I get an email or 2 or 3 or 18 that essentially introduces me to your publication and What, what the benefit of following your publication is, what the benefit is to me as a reader. That's what a drip sequence is. It doesn't have to be 18 emails. It can be one, as we'll take a look at. But depending on what industry you're in will determine exactly how long that sequence should be. Now, one thing I will mention is as soon as somebody registers specifically on the site, they'll get a welcome email, more of a transactional email from you as the publisher. We have lots of publishers now that are running, thank God, free registrations, building lists very quickly. And that welcome email has usually an email and a password in it. It's plain text. It's very simple, but there's an opportunity here to make sure there's some sort of, we call it a CTA, a click-through action, like a subtle message in the welcome email at the bottom that says, hey, join or subscribe and get everything. It's a simple thing to add to your transactional email that I see a lot of publishers just flat out missing. And as you're looking at the screen, the welcome, the transactional welcome email is the most opened email you'll ever send. 70% is the, is the industry average. Okay. This is something we talk about all the time. It's confirmed through a Substack study, but If you're, if you're running a list of free registered readers that come in, you should expect 5 to 10% of them to convert to paid subscriptions. Could be even more, especially when it comes to local news, right, Tyler? And so this, this drip sequence becomes another important tool in your arsenal of, so your email newsletter. Okay.

All right. All right.

Let's look, I'm going to try to get through these as quick as possible. There's a lot of information here. Okay. How long should you drip your email? Now this is, this is an interesting one that I dove into. I'm not like a super duper email expert, but I did a lot of research. We have our own publishers that we're looking at and essentially, um, the, the, the, the like niche enthusiast publications where it's more membership, right? Like you're going to join a tribe, you know, like, hey, I'm, you know, I build small wooden boats, which we'll look at, right? And it's like, oh, I love, I love that. Or I love fishing, you know, I like deep sea fishing off the coast of New England. Like this is the tribe tends to be a little bit shorter. People know they want to join. You kind of just need to open the door for them. They love, they're already enthusiasts. And then there's the, it's kind of like trust-building educational side of it. So like Moss Report, which we'll look at, and we did the pod, we did an interview with Ben Moss the other day with another, another great podcast. If you want to, if you're a niche publisher, you should listen to that one. He's killing it. And what, but as far as like educational and building trust, that's where longer, like a draw, a longer email drip, and he does 18. Emails. You know, he's in the, in the cancer field, people are, are super engaged. And they're looking for information they're looking and, and he needs to build trust with that crowd. So there's really more informational emails that go out. So those are the two. Local news, I think is, is kind of falls a little bit into the trust building side of it. You know, you're building trust with your, with your local community. Is it, is it Membership? Not, not really, unless you have some very special programs running. And I'd say that there are a lot of different approaches to drip when it comes to, to local news, but I believe, yeah, 4 to 6 emails is sort of the kind of the middle ground for, for most publishers. Okay. Just a quick note on when you send your emails, your first, your first email or two will come pretty quickly, you know, within the first hour. Certainly within the first day, the first week, you'll kind of have sort of a compressed time to send the emails. And then you may want to go out over a month and then start sending emails out every few days if you, you know, depending on what your, what your, your, what messaging you need to get across for your specific publication. Okay. I'm just gonna keep, keep cooking here. All right. So let's talk a little, why don't we jump ahead to local news and talk about that? Tyler, I know you're, you're, you know, you work with a lot of local news publishers. I think they're doing different things. I, you know, I saw some things in this list here that I really like, but do you have any, you have any particular thoughts on, on local news that you wanna, you wanna make sure everybody knows about?

Yeah, for sure. So with local news, I think what's most important for a drip campaign series is more of an introduction to your team and what your mission and goal is for your community. And so we often have publishers that will, you know, obviously there's CTAs, there's call to actions in there about subscribing and things like that, but it's, I think it's more important for local news to introduce their team. Photos of your team, personalize those, those drip campaigns. And do you need to send 18 of them? Maybe not. We have publishers that have, you know, 2, 3, 4, 5, 6. It really kind of depends on what your, you know, what your target, who your target audience is. So most of our publishers are in, you know, smaller towns, medium-sized towns. So, you know, 3 or 4 is generally enough. They know who you are, at least even if they don't know you, they about you. So, you know, those, those drip campaigns can help sort of solidify that, that trust building exercise. So, so yeah, it's something you should do. Is it going to like fundamentally, you know, change everything for you and you're going to see like a, you know, 30 signups or whatever, like some massive percentage from it? No, generally not. It's sort of a long-term you know, again, a trust exercise, I think, for, for most publishers. And honestly, I think, uh, for, for publishers, it's, you know, comes down to your content, right? So everything you can do around that content, whether it's drip campaigns, the free registration funnel, all of these, these different techniques help and they help grow. Um, but ultimately it's, you know, it comes down to your content and what you're, what you're offering.

So yeah, for sure. Um, and yeah, just let's focus in on content, uh, a little bit as well, 'cause from what I, you've told me and what I've seen is local news publishers sometimes have sort of different content foci, if that's the right word.

Yeah.

Right.

Yeah.

Like, like I think New York City publisher there is crime and food is really hot, right? Like that's, that's looking at the analytics, you know, there's a lot of, of traffic in those two. Whereas maybe someone in rural West Virginia, that's not really the focus at all. It's, it's, And maybe it's, you know, just like high school sports and, you know, sort of the real local, local stuff. And then out in Oregon and the capital city, it's like, what are the politics going on in town hall? Like, what are the politicians doing? Let's cover, let's make sure they're, you know, we hold them accountable. So, but my point is, is that you pick your topics of focus and then when your email goes out, you wanna basically tell your, You know, you know, your potential paid subscribers. Hey, we focus on crime, you know, so you know what's going on, right? And, but, or food, so you can go check out the new restaurants first. Like, you know, whatever topics, like whatever topics are core to your publication, pick one, make one drip email, like on that topic, make it food, make it, you know, politics, make it. you know, crime and, and that's the one focus topic for each of the drip emails that go out.

Yeah. Yeah. I, I often publishers come to us and they're at, they, they'll ask us like, what should we focus on to help drive subscriptions? And like, what kind of content should we be focused on? And sometimes locals, you know, they're, they're focusing on all kinds of stuff. It's, you know, local government, it's schools, it's, it's a number of different, different topics. These are things you can figure out when, you know, in your analytics, you can figure out what's, what's most popular, what's driving free signups, what's driving paid signups, and that, and then you can kind of lean into that content. So speaking of a, a New York City publisher, they figured that out based on what was driving conversions. So if it's food and it's crime and those two things are working for your audience, that's what they want to read. Focus on it.

Yeah.

And so the same goes for any other town. So maybe you could try a number of different verticals of content and then see what sticks, see what's driving the conversation for people and then focus on that.

So, yep, for sure. And I would absolutely say don't get worried about having to create, you know, 10 drip emails or even 5. Focus on, you know, your, if your content is focused on 2, 2 topics, then, you know, send 3 emails, right? Mission is first. And then, you know, just to pick on New York City, it's like, you know, food is second, crime is third. And then maybe the fourth is just a, hey, like a promotion or something to get them to pull the trigger on paying for a subscription.

Yeah.

Yeah. So that's it. The less, the less you send to someone, the higher the impact.

Yeah.

Right. The, the, the, you know, it's, this is true across life. Like if I have to look at 12 things on a website, I don't know. I'm not looking, I'm just confused. Right. But if I'm looking at one thing, I know exactly what I'm looking at. So the impact of having less is, is far greater than having more. Yeah.

And that's something to note when you're building these drip campaigns, go through the process yourself after you've set this up, you know, if you've ever ordered anything online and you know, you get like 15 confirmations or shipping confirmation. There's just, you know, a number of different things that flood your inbox. You don't want to do that. You know, you want to, you want to slow the cadence on these emails with your drip campaigns. You don't want to overwhelm people. You don't want to be sending an email every 5 minutes, every 30 minutes, you know, nagging them to, to subscribe. So cadence does, does matter for, for, for conversions.

I'm glad, I'm glad you said nagging to subscribe, agree on cadence. And then this is, this, this camp, these campaigns are all about just introducing your content with trust. Like that's really what it's all about. You can have a, you can have upgrade messaging at the bottom of your emails, but this is really like your introduction to this new reader who just signed up for free, you know, with the, with the motivation that if you give them enough value and you give them and you build enough trust and it's, and it's content that they truly want that they will at some point down the road pay. But this is farming, right? Like this is nurturing. You're, you're, you're not, oh, hey, thanks for signing up. Here's 50% discount.

I was just about to say that like, this is not an opportunity to completely give away your product and offer a 50% discount on, on anything. So don't, don't fall into that trap. Like use this as, as you're saying, like as an opportunity to build trust.

Yep. Yep. For sure. All right. Let me just flag a couple of things I thought were really, really cool here. So you mentioned like a welcome from the editor and, and the mission email, like that comes, comes right up front. That's maybe an hour after, you know, the welcome transactional email comes in. One of the things I thought was pretty cool is like we broke this and I was thinking about Salem Reporter, you know, they do a lot of, a lot of coverage about, you know, what's going on in local government. Decisions and things like that. And it's like, you know, hey, we broke this, a signature investigation. Like, that's, that's really powerful. It's like just giving your, your free reader an example of like, this is the work we do. Like, we did this, you know, we did this investigation. It took X amount of time. This is what we dug up. This is the results. This is what your subscription gets you, right? Like, I thought that was super. I thought You know, that was a really powerful—

Salem actually has an email similar to that for their drip campaign. And it, it, the, the, the subject line of it is Holding Power Accountable: How Salem Reporter Works for You. And so they go through the process, get into the weeds of like, this is what we do daily. This is how we, how we make the sausage. This is what we're doing for the community and for, for you as a reader. So, exactly. You should be, you should be doing that in your drip campaign, especially if you're a local publisher.

Bingo. Okay. Well, somehow, somehow, uh, the publisher of some reporter is predicting the future here. This is good. All right. Um, let's see, we talked about picking your content that you're focusing on. A neighbor testimonial as one of the emails. It's like why one of your subscribers pays for subscription. You know, I thought that was pretty good. And you can have like kind of a soft ask in there.

Social confirmation.

Yeah. Yep. Yep. So anyway, I thought those were good. All right, let's move on. Um, we talked a little bit about, uh, the volume of emails, whether you're sort of in the membership identity space or more in the trust space. So I'm going to, I'm going to kind of skip, skip past this slide and then, all right, let's go talk about a couple of niche publisher examples and what they do for drip campaigns that have really knocked it out of the park. So we're going to, we're going to look at Small Boats. We haven't looked at Small Boats in a while. They are still plowing forward, rowing forward. Sorry, I was trying to come up with a good analogy here. But nope, I couldn't do it. Okay. So they, when, when, when somebody registers on their site, they, they give away one free article, then they pop the registration. You have to register to read that next article. If you're not doing that, start doing that. That'll grow your list so much faster, like 500% faster. It's crazy. And I have a sample. I have the example of what they send, right? It's a, it's a welcome to SmallBoats. Your account is activated. How to log in. That's it. You know, username, password, whatever you wrote. And it's, it's super simple. Now, this email gets on average a 70% open rate. So I would suggest to Small Boats that below this, have some simple text, nothing fancy that says, hey, you know, ready to join, you know, click subscribe, off you go. Okay. Now what, what happens in after 1 hour? This is what happens. They send an email, they wait exactly 60 minutes and send this next email. And it's the only email that they drip. It's the only one. It says, welcome to Small Boats. And this one, however, is HTML. It's beautiful, right? You got really nice, nice photos. Uh, welcome. If you're, if you're watching this on YouTube, you'll see this, but essentially it says, welcome aboard. Thanks for checking out Small Boats. We hope you enjoyed that free article, but believe us when we say you're, you've barely dipped your toe in. From seasoned mariners to the nautically curious, our members find what they need to keep their dream afloat. And then a join now button. Right. So this is like, I'm a, I'm a wooden boat building enthusiast. I've registered, I've gotten this email. It took me, it took an hour later. And what they're finding, I'm not going to share the dashboard, but what they're finding, I've looked at the numbers. What they're finding is that this email is their highest converting inbound marketing piece, period. Like by a long shot. People look at this and they don't, they, and they click the join now button and they pay. So why, why do they do this?

Right.

It's a couple of things. One is when somebody registers on your site for free, they're signaling engagement. They're like, oh yeah, I want this article. Uh, yeah, I'll take the newsletter. They're putting in their email. They're putting in a password. Right. It's not just an email popup. They're, they're signaling like real engagement. They get the welcome email. They look at it. Fine. It's not much on that. And then an hour later, they get this email. Now in an, in that hour, they've probably done what? They've probably read an article, right? I mean, that's why they dropped off the, I mean, they did the work to unlock an article, right? It's like, now they're reading the article. Give them an hour to read the article, right? And then cool off a little bit and then hit them with the, the, the, the join message. And you're hitting them in that, what we call a honeymoon period, right? It's like, I, I, I got the, I read the first article for free. It told me I needed to register. Okay. I registered. I read that article that I registered for, and then an hour later I get like, hey, why don't you join? Well, now I've read two great articles. I really like this. I mean, I'm feeling good about it. So the chances of me paying is, is up, right? I'm— you get somebody at peak engagement at this, with that one hour later. It's crazy, right?

Yeah. You're literally giving them time to digest your content. Your brand, they're brand new to you, like relax a moment, give them some time, let them, you know, take it in. And then an hour later they get this really nice, you know, call to action to, to, you know, to subscribe. So, and if you've ever signed up for or ever gone through like checking out for an airline and you're looking at prices and you put in your email address and then you don't book it, maybe you're just looking for how much it costs or looking at flight routes or stuff like that. You do that, you come back an hour later, there's an email. It's like, oh, by the way, did you want to book that trip that you were looking at? And you're like, oh yeah, I remember looking at that an hour ago. Right. So it's like, it kind of sucks you back in. Oh yeah, I need to complete that at some point. Right. So it is sort of the same, same kind of thing here.

Yeah, exactly. Yeah. You're, you're, someone's engaged. You don't let them go.

That's right. Yeah.

And it works.

It works. So they wouldn't do it. So.

Yeah, absolutely. Well, I, I've looked at the data. It's the highest converting inbound. We look at, so with our new Subscriber Insights dashboard, we have the UTM codes tab up there. If you, if you don't already know this and you're, you're, uh, uh, use our platform, uh, with the new Insights dashboard, you can just start adding UTM codes to all your links and everything you do. Could be a button on the website, could be your newsletter, could be any, any paid campaigns you do. You just put a little UTM code on the backend of all your links and then it will, in the dashboard, it'll just track everything. You'll see exactly what's converting paid, how many dollars are converting to paid. Super easy to set up and you get, you get the, you get the conversion data. Looking at this data, I'm looking at these numbers and I'm like, you know, okay, okay, okay. And then bam, this welcome email is like 5 times greater than any other, uh, any other metric they're looking at. And I think they got maybe 20, 20 UTMs running right now for inbound monitoring. It's wild. Absolutely wild. Okay. So let me just, if you're listening to this, let me just break down this email a little further. So it's a beautiful picture. It's got the welcome aboard and the text I just read. It's got that singular button. It's very clean button. It just says join now. And you join for unlimited access to, and then below that, you get both profiles. There's a, there's a block with a picture and some text. You get designs, the block, some text, you get reader-built stories, you get adventure stories, and these are all little nice blocks. And so they're, they're basically saying, hey, there's one, two, let's see, boat designs, designs, reader-built adventures. There's like four main content areas that you get. So they're showing that off and then, hey, you got much more and then another join now button at the bottom. So that's the, that's the structure of this email. It's kind of like baking in You know, the pitch up top, the pitch at the bottom, and then like the main content focus for them.

Okay.

All right. Let me check my notes. Let's see. And to be clear, there's no price on here, right? There's no discount. There's no urgency. There's no testimonials or countdown, you know, number nonsense on here. It's just a super clean, high-quality, elegant, you know, hey, you know, welcome aboard. You should join. That's it. Yeah.

Okay.

Uh, uh, so you could kind of think of it as a welcome brochure. That's an old, old-timey kind of a word, but it It is what it is. Okay. All right. Let's go to our second example. This one is different. This is, this is Moss Report, um, independent cancer journalism since 1974. This is really a membership. Um, again, if you want to dig into the success of this publisher, listen to the podcast we did. Recently, and they have an 18-email drip nurturing campaign. You and I talked about this during the podcast, or no, no, that was— sorry, Ben was on the podcast. I'm sure we talked about it sometime because we talk about everything. But the— so 18 emails go out after somebody registers. Now, just to paint the full picture, You know, they're dealing with a very sensitive topic, uh, you know, people that are struggling with, with cancer. Um, and they have a lot of, um, sort of more holistically based information that's been, um, you know, researched and they've been doing this for a long time. They've helped a lot of people. Um, something to, something to, to look at what they're doing and what he did. I think it was February. It wasn't that long ago. It was a few months ago is there's a, you know, they're in a space where there's a lot of information, right? And thousands of articles. And so what he decided is for the free registration, instead of just like giving away an article, they put together a package called the Essentials of Cancer, right? So if I click that, I get sort of a breakdown on what, what you're going to get. If you sign up for the Essentials. I think it's about 20 articles that you get. So you get a bundle right off the bat if you register for free. So if you're in the niche space, right, think about your content and think about if there's like a bundle of information that would make sense for you to give away if somebody, you know, gives you their email and password to create an account on your, on your website. So what he decided was to give a very helpful bundle What happened when he turned that on is his free registrations jumped 30%, have been up 30% since he turned it on. So it's a big jump in free registrations, packaging the bundle. Okay. So I drop in my email, I choose a password, I sign up for this, I get access to the Essentials content. And you can see that he's promoting the member content on the side here, which you have to pay to get access to. And then he kicks off 18 emails. Right. And then those are spread out over a month and a half or something like that, or a couple months. They're, they're, they're pretty, they're pretty spread out. Okay. He quoted, let me see here if I can find the, find the quote. I can't find the exact quote, but what he said is that every time he found that his paid conversions jump every time the drip fires, like he's looking at his analytics and seeing that when, when, when the drips go out, paid conversions bump. And he's in that building trust space, right? Expertise and trust. And, and you can really You can really only do that over time, right? You don't just run into this and go, oh, I trust this completely. You need to read the content, maybe try some things. Like it takes time to, to build trust. And what I think is interesting is that the bundle kind of makes the 18 email series work, right? It sort of sets you up for deep engagement. Like if it was like, read this, this one article for free and then then you get 18 emails. It's like, whoa, that's a lot. That's a lot, you know, but no, it's like the Essentials is 20+ articles and you're like, you get this like, you know, like mini library to dig into. And then, and then 18 emails over time is like, oh, well, here's more deep content. You're kind of ready. And again, you're, you're looking for, you know, you're dealing with highly engaged audience here. So this Works. Okay. Now, one thing that the Moss Report does really well in their emails is they— let me see if I can go find an example. What they do is they pull it up— is he writes kind of a personal intro. To each email with some little bit of extra information. And so I'm going to put in— and that makes you want to click to the website, right? And when anytime you get somebody to click to a website, what happens? You get a chance to, you know, upgrade message them, right? So here's an example of an email. Hello, healers. And he talks about, um, scientists begin suspecting that cancers have stem cells. So he provides a sort of value, like personal, personal, uh, uh, intro with value right in the newsletter and then a link to the article. So he's, he's, this is, takes effort. No doubt. This is not a, this is not a thing you just set up right away. He spent a lot of time and energy in doing this, but it's paying off. You know, his registrations are up, his paid subscriptions are up. You know, it's pretty impressive what's happening here, but he's obviously putting the time in. So every drip email that goes out, it's got like a personal, you know, little analysis of what's happening. It gives you value right there. And then you click off to the article. It, it works incredibly well. The other thing he does is A lot of these articles are only available for free for a limited period of time. So we have a, we have an extension called the Archiver. I think it's called the Archiver and you can set any article to, to go, to change from free to paid over a period of time. So it's like, you could, you could have like, article once it's published, it's good for 30 days or 2 days and he's just got like, an article, articles open for like 2 days, sends a newsletter out. And it's like, you, you have to, like, you have to click now if you want to read it or it's going behind the paywall. Right. So it's very clever. And he's creating urgency in his email series to get, getting people to the website and then being on the website. And then they go to the next article and, oh, I need to upgrade. I need to pay. They get the messaging to pay. So that's another, that's another sort of value for this drip sequence, you know, the drip sequence and then his, you know, fresh content go out. And, uh, you know, it's all about sending people back to the site. So if you have, um, maybe it's a category of content. I don't know what would work in local news. If this would, this would apply in any way, but you could get access to content. Um, because, you know, if you, if you click now, essentially, Right. As a way to drive urgency. So I don't know, just a thought. Okay. I'll just close with something philosophical. How's that? This is from Ben. This is not for me. This is from Ben. Cause I asked him in the podcast, I said, hey, you know, like what's, what's the one thing that you sort of have regretted a little bit and want to work and You know, and, and realized and, and now you're working on bettering, right? He said, my biggest failing has not been using and trusting my own voice. That was it. He, he, he's leaning into really, really trusting the power of his voice. And I think, I think you can appreciate this. You know, we talk to a lot of publishers and there's a lot of, there's a lot of AI going on and stealing content and there's a lot of, fear on like what to do, what to do next. And you don't want to, you don't want to piss off your readers by putting up paywalls and things like that. And, and the real, you know, I think what Ben said is like, trust your voice, your content's awesome. You have traffic, right? You know, you have content and those two superpowers give you everything you need to build your audience and convert that audience to paying subscribers. So I thought that was pretty cool.

I love it. I love it. Yeah. Publishers tend not to have any confidence in their content. And we see that a lot with Paywall Project customers where they come in and they're ready to go. And then they say, oh, we don't want to turn that paywall on.

Oh, really?

Okay. So, yeah, there's certainly like a level of of confidence and, and yeah, like leaning on your brand and what you've built and trusting that there's value there and giving it a, giving it a shot.

Yeah, I, I just need to say it again, you know, like if you as a publisher listening to this, you have two superpowers. You have your, you have your content and you have your audience. Those are the, you have traffic to your site, you have an audience that, that likes your content, you have your content, that's your gold. And you got to leverage that, right? Like that, that's how you survive in today's, today's world. You leverage it and you leverage it by putting up that free registration. So you, you, you, you're requiring people to give you their email list. You're not popping up saying, please, please put your email in here. You're saying, hey, you want access? Give us your email. And you can decide how much access you give afterwards. And then you tighten that, you just tighten that up. And all of a sudden you got yourself a booming list, booming paid subscriptions, and confidence, you know, heading, heading up and to the right.

So, all right.

Thanks, Tyler. Good stuff. Catch you next time.

Thanks for listening to the Paywall Podcast. If you'd like to get in touch to discuss subscription strategy, go to leakypaywall.com. See you next time.