Episode 19 | Subscription Accelerator™ Part 3: Converting Casual Readers to Paid Subscribers
19 Nov 2025 · 41 min
Pete Ericson, Jeremy, and Tyler break down how to turn free readers into paying subscribers through better messaging, targeted email campaigns, and strategic site prompts. They cite New York Times growth patterns and Small Boats Magazine's email approach, then recommend testing conditional header bars, drip campaigns, and simplified subscription choices to move readers toward paid tiers.
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This episode of the Paywall Podcast is brought to you by zine101, the makers of Leaky Paywall. Leaky Paywall is the most flexible WordPress subscription platform. Find out more at zine101.com where you can download Leaky Paywall for free. On the Paywall podcast, we discuss paywalls and paywall strategies for news and magazine publishers. Let's get started.
Welcome to episode 19 of the Paywall Podcast. I'm here with Jeremy and Tyler and we're going to have a chat about how to convert your free and casual readers into paying subscribers. This is step three of our subscription accelerator framework and we're going to assume here that you have started collecting free registered casual, semi casual readers and that are getting some limited access to your content. And we're also going to assume that you're sending your newsletter of great content to these readers, teasing them to to pay for a subscription. So. Hi guys. Welcome. Hey. Hey. Are we recording? Actually, I don't see it. Yeah, sounds like it's recording.
Says recording on my screen.
Perfect. We've had some gotomeeting issues. Maybe it's just me this morning, but we're going to press on. One thing I will say is that if you are collecting free registrations on your website and you're sending your newsletter out to these free registered users, you are, you're winning half the battle just doing that. And so today we're going to dive in deep into what are the things that you can do to up the odds that somebody who's a casual reader that's in your newsletter now will actually pay for a subscription. So what I thought I'd do first is just kind of jump in with some statistics. And actually what I'm going to do before first is talk about what we're going to talk about today. And there are really three things. One is your messaging and your benefits to these, these casual readers that you want to convert. Two is we're going to talk about touch points and targeting. So what moments in time you have the ability to get your, your message across. Hopefully convert that paid subscriber. And then we'll also touch a bit on some easy opportunities that, that you might want to explore as far as adding additional benefits or revenue to, to your publication. Okay, so now onto the data points. So we are looking, we are doing a screen share here. So there's a little video component of it, but we'll describe everything we see. And I want to just get back to the thing that sort of launched us into building leaky paywall. And that is the New York Times. So the New York Times launched their paywall in 2011. I discovered this morning, or remember this morning, with zero digital subscribers, right? And this is the point where we find a lot of print publishers at, or brand new publishers at, when they starting starting fresh with Xero and then 10 years later. So from 2011 to 2021, they've been growing their paid digital subscriptions to their news, and now they have other products too, like recipes and games and such, but their news platform. And when you look at the curve that's on my screen here, you see something that's really interesting. If you, if you go back to 2011 and you extrapolate, you'll see a pretty flat but steadily increasing curve of new paid subscribers. And then somewhere around 2016, I think was the Trump bump that bumped up paid subscriptions to a whole new level. And then even just in the last few years, 2019, 2020, the digital subscriptions actually accelerated for the New York Times. So they went from, in 10 years, from 0 to 5,600,000 paid digital subscribers of their, of their news product. So I think that's interesting, and I think that that also speaks to how time is really your friend in this equation, which kind of takes me to the next data point. You will as a publisher, and if you're reaching into digital subscriptions, your hardcore readers, your hardcore fans, those that are close to you, will subscribe pretty quickly. They'll just come on board pretty quickly, and then the next group, which we're looking at a chart here, which breaks down into heavy users and casual readers, and it's those casual readers that come next. And what the data's showing now is that these casual readers are really your biggest opportunity. They're the biggest group members of your audience, and therefore they actually translate to your biggest potential as far as new subscribers go. But again, it takes time. And what we're going to do now is we're going to talk about how over time, you can make the experience of your publication to these casual readers better and better. Okay, So I say the word experience very deliberately, and something that we went through ourselves not that long ago was essentially how to onboard new, in our case, publishers, and in your case, new subscribers, paid subscribers. And the onboarding experience is something that was a real light bulb for us was that the onboarding experience starts with the first view of your website, in other words, and you want to, what Samuel Hewick will say, show the top of the mountain. So in other Words. You as a publisher offer lots of features and benefits to your paid subscriber. Really what I see is publishers offering mostly features. But what's the benefit to the reader? What's that singular benefit that your reader gets when they become a paid subscriber, when they become a member? And if you're a local news publisher, it's joining the community. If you're a magazine publisher, you're joining a community of like minded enthusiasts. Let's say, as an example. What is the benefit? How does life get better, better for your subscriber? And you want to think about that really at your first point of contact and all other points of contact in the experience of bringing that casual reader into the paid subscriber. So you're always onboarding. That's sort of the point. And by the way, Samuel Huick wrote a book called User Onboarding. And if you go to useronboard.com, you can find it there. It's excellent. It'll absolutely open your mind up in terms of how to approach your customers or in your case, your subscribers or members. Really terrific. Okay, so we've gone through the onboarding conversation. So one of the things that I see, and I'm just going to harp on the experience a little bit, is that it's very tempting to throw advertising at your readership saying hey, join now. Discounts and promotions and email blast and such. But just be very careful of that. That affects the experience that you're bringing on. You want this kind of messaging to happen slowly over time, and you want it to fit your brand. You want it to be sort of gentle, not aggressive advertising. And you can work that into all your touch points. One of the things that you can do too is as all organizations struggle to sort of find that that tagline or that messaging is ask your own readership, your best subscribers, why they pay you, and that will help you come up with really the reason and the big benefits to your readership which will help you architect the experience that you want to architect. All right, I've gone off the deep end a little too far. Let's get into some brass tacks here. Okay, I want to jump into the first point of contact, which is really the most important. And that's the email newsletter that goes out. And this is the thing we've talked about before. If you've listened to any of the other previous episodes, when you get that free registered user, now you're sending your newsletter to that person over time, it's likely the second largest source of paid Subscriptions. Sometimes it's first, sometimes it's third, but typically it's about number two. It's a great conversion tool and I would say with your email newsletter because it's so important and it's really your main direct marketing tool that you need to make it awesome. So now's the time to really step back and look at it. If you're using mailchimp or Constant Contact or really any other email provider and you haven't stepped back and really designed it to match your brand, that's worth the money. You'll get that money back so many times over. Make it clean, make it readable. And I'm going to show. And I will describe an email newsletter that, that works really well. Let's see if I can figure out where it is here. Oh, it's in my Gmail tab here. So we're looking at Small boats Magazine, smallboats monthly.com. you can check it out. There's a free registration on there. Sign up and get that email newsletter. It's a great model of what it can look like. Now. It is a magazine, but it's got something in it that I think every publication really needs to have. And it's a call to join in every newsletter. So what they do a good job doing is. And it's, it's not intrusive. It's at really, it's underneath the content for that. In your case, it'll be day or every week or every month. And essentially it says join the small boats community and you'll receive. And then there's a list of bullet points, six bullet points of benefits that you'll get. And then there's a big button underneath that that says join Small Boats today. And it's that messaging in your email newsletter that over time, you're not, you're not, you're not beating somebody over the head with hey, you know, subscribe or hey, discount or whatnot. It's just the, it's. It's essentially part of the newsletter experience. If you're not already a member, join these. This is how our content is going to help you. This is how it's going to benefit you and change your life. That's sort of the angle you want to come from. Okay, just taking a sip of my tea here. Any other comments on the email newsletter? I know we talk about it a lot, but it is, it is the really the number one direct marketing tool available in the toolkit. And you want to make it awesome.
I would say one thing that I like that Small Boats does that I don't see everyone doing is putting the list of benefits by the subscribe button. A lot of people will say, hey, subscribe today. But I like how here Small Boats has, you know, a list of like you said, I think six benefits of why you should. Because sometimes, you know, it's hard to for a subscriber to know all the different things they can get just by looking at your website. So I like how they spell it out here. And I think a lot of publishers that I've seen could benefit from adding that to their own newsletter and even on their subscribe pages calling more, calling out more of what the actual benefits are of subscribing.
Yeah, that's actually a really good point. I would encourage everybody to go to smallboats monthly.com and go look at that subscribe pa because what they do is exactly that they build. They have a landing page which sort of warms the, the reader up to what the benefits are for the subscription. And let's see, if I click that link, it should take me here. So, yeah, so here's the landing page. Essentially what it says is subscribe to Small Boats. At the top it's got a neat little intro paragraph with a signature of, from the editor. And then beneath that block it's the price and then the bullets and benefits of what you get if you subscribe. That's, that's a, that's a great. Now what they're doing too is they're simplifying their touch point and that's. We're going a little off the rails here. But this is a very, very important point, is that the less offers you have, the higher chance someone has of not being confused and having to make a decision and actually paying for a subscription. You know, Netflix has really proven this. You know, it's a, it's a recurring monthly. That's it. There's no annual subscription, there's no three month subscription. You can't buy individual episodes. It's just recurring monthly and that's it. No other choices. And so they. So Small Boats has one year recurring. That's it. If you look closely at their subscribe page, you'll see that they also call out their gift subscription right at the same time. So it's the same subscription, but either you buy it for yourself or you buy it for someone else. And that's a, the gift subscription is part of that opportunity section I mentioned we're going to talk about later. So. Yeah, good stuff. All right, Now I'm going to stay. I'm going to stay in the email theme. And one of the things that you can also do when somebody registers for free is target them via email in a nice way. And that's through a drip campaign. And so what is a drip campaign? Well, drip campaign is a, all the email service providers like mailchimp have them. Basically what you do is when somebody signs up to a certain level, you'll send a tag to, let's say mailchimp and then let's see if it's a free level. You could tag that as free and then you can start off a campaign of say, five emails that drip out over the course of 30 to maybe 60 days. And what's the purpose of these emails? Well, the purpose is to help explain why your publication will make the life of your paid member better. You know, what are they going to get? Now, every publisher that we look at has a lot of different benefits that, that are part of the experience, you know, and it could be certainly as joining the community, it could be having access to events, having, being able to comment as a paid subscriber on the site, having small boats actually provides access to unlimited classifieds posting, which works really well for them. And then of course there's essentially the big benefit of the emotional appeal of, you know, helping, helping the, you know, your publication survive. You know, like we need subscription income or membership income. And, and that works exceptionally well. So all that kind of messaging in terms of what the feature is, what the benefit of the feature is to the reader, how's it going to help them? You can drip that out over time, right? In a nice way. And so it's not a hard sell. It's really more of an education of who you are, why you need their support. And then ultimately, of course, in each email you have that know, join now button so that you, you, you're, every time you touch somebody, you give them the opportunity to join now. And that's, that's how you know that, that's, that's what works. You know, I get emails all the time from organizations I've given to in the past and they keep pestering me again in a nice way. Like Wikipedia does a, does a great job with it. You know, they're really, they're really good at focusing on the benefits of being a contributor. And you know, I don't give them a lot, but I give them something. And not every time, but sometimes, but they keep on me. You know, time wins, right? The chances of me giving increases as I don't give. And then I finally Decide to give. And that's how successful organizations that are in the SaaS world, which is really what publishers are doing with digital subscriptions software as a service. It's really content as a service. I guess we can come up with a new acronym, maybe Cas. I don't know. Stop me. Okay, so drip campaigns. Consider setting up a drip. It's super easy to do. I think mailchimp charged you 25 bucks to turn on that feature per month. And all those free registrations that come come in and pouring in, really, you'll have more free registered users than any other type of subscriber typically can be essentially in a nice way asked to pay over time as you drip them emails. All right, any comments on that? I will say just, just to be, you know, thorough here is that when, when folks do subscribe in on your site that you're going to assign a tag to that subscription to that subscriber and send that tag to an email provider like mailchimp. Try to keep your tags simple. In other words, if you're digital only, then it might be just free and paid regardless of whether they're monthly or annual or not. You could start to really, you know, break these out as monthly and annual. But what we hear back from publishers is that gets complicated to manage. So I would start simple. You can get complicated later. If you're a print publisher, you're probably going to have free digital paid and print paid as your main categories. And then you can, you know, with those tags comes the power to send promotions to. So yeah, you can, you can target your free tagged subscribers with a promotion. But just be really careful. You don't want to train people to expect discounts. That's really dangerous waters. You can, however, promote and let's talk, let's get back to gift subscriptions a little bit. So you know who's, who's likely to maybe give a gift subscription during the holidays right now? Well, how about your paid, you know, your paid readers, free readers, maybe they're somewhat committed to you as well. Maybe, maybe you can create a crafty benefit to the free reader where, you know, they get to get a subscription and give a subscription maybe through a coupon code or something like that. So these are these that would be smarter way of targeting without actually giving a discount. But consider that make sure that your tags are getting sent in to your, to your email provider. And by the way, gifts back to gift subscriptions. So from the print magazine industry, if you do any research, you'll learn that if you Have a giftable publication. About 20% of your subscription revenue should be in gifts, which, you know, when we look at our network of publishers is not generally happening. So there's a lot of money on the table by really going after gifts on a regular basis. Certainly during the holidays and year round. Gift promotions work and can be a big part of your revenue. Okay, anything about email newsletters, email targeting that we should talk about? Talking about targeting here, Touch points in the email world. All right, let's move on to on site targeting. So how do you, you know, how do you target on your site? Now the one thing I'll say is go to your website, don't log in, trigger your first subscription message, the nag, which is, which may be a paid subscription message. Hopefully it's the free subscription message and see what it looks like. Is it the default subscription message? I cannot tell you how many times we go to a publication and we go trigger the subscription message that says, hey, you've run out of articles, you need to join for free or pay. And it's the default subscription message. And this is again back to what I was harping on earlier. This is part of your brand, part of your experience that you're onboarding your potential subscribers to. So a clean branded, you know, your logo, colors and elegant messaging. If you're, if you're, and hopefully attracting your free level subscribers, then that's, that's all you want to promote is hey, join for free. Read the article that you're looking at right now. Maybe get one or two or three or more free articles per month, let's say. And that's it. The purpose of that first touch point on that subscription message is to collect that email address because then they're on your newsletter and then you have this. Now you have time on your side to convert them to paid. That's it. Yes, you should give them a link to log in and yes, give them a link to subscribe, but keep it focused on that free registration. And then the second, now go and log in as a free level subscriber. And what you can do is there's a user switching plugin that you should have installed so you can go to your subscriber table and just switch to a free registered user and then hit the paid look at some articles, hit the paid subscription nag and you know what do you see? Do you see the, the generic message or do you have a nice branded message? So I'm bringing up the small boats since we're picking on small boats here. The upgrade Your account message logo, Upgrade your accounts in big text and then subscribe now. The price, the benefits. A button that says subscribe now which takes you to that nice subscription landing page. And that's it. It's part of the experience. Now remember, this message will be shown over time multiple times, which is what you need to do today. You need to show your messaging multiple times to gain attention. And so you want to keep it elegant, you want to keep it simple. There's one button there. It's a clear call to action and you want to pester people over time with this. So if you have the default subscription message upgrade message, it's time to take a look at it. And again, whatever investment you make in time or maybe getting a designer to do some light design work and it won't take very much, will pay off. Anytime we see new designs come online for websites or email campaigns or whatnot in the digital space, the results are dramatic. You know, it takes time to put this together. But once, once you have a cohesive design and experience, especially messaging, it works and it works like gangbusters. So I would say give yourself the gift of time to look at how your subscription experience works. Okay, All right, let's go back to subscription options. We can all be small boats and have one subscription option. Sometimes we sell print and we need to have more than one subscription option. That would argue that you have as far as your subscription page, three or less items to look at. Which is the psychological best. You know, I don't know how to say it, but it's, it's, it's how our brains work. If we have choices of three, then it's easy. We can pick one, two, three. So you might have a digital, you have a print digital and you know, maybe there's a membership like a higher level that you're offering. That's it, three choices. Now on each subscription card choice, you could have buttons for monthly and annual. It's the same option. Maybe digital, only monthly and annual, print, maybe it's just annual and then membership is whatever and that's it. So if you have one option, great, you can really work on the messaging for that landing page. If you have two or more, stick with three and offer your gift subscriptions, offer your corporate subscriptions underneath as really kind of add ons and things that you might target separately. Promote to separately. Okay, on the theme of website targeting, there is something that, that works really well. It doesn't pester too hard and it's, it's what I call the header bar. Promotion. Jeremy, what's the name of this? Is this the conditional display notice, is that right?
It is, yep.
Okay, so conditional display notice. What does this do? This puts a little thin header bar at the top of your website. And the cool thing about it is is you can target what subscription level for it to show. So we have it, I'll describe what we have here. We have it on the site here. So you're looking at the page I'm looking at. There's a orangey brown header bar that says you have unlocked a reward. Get your first month free with our annual subscription and a link to the annual subscription registration page. And so this is a promotion that is set to only display to free registered subscribers. So if, if I'm a casual visitor, I won't see it. If I'm a fully paid subscriber, I won't see it. I'll only see it if I'm a free registered user. So I'm not paying it. I'm in for free. I'm logged into the site, I see this bar and what's cool is you can really, now you can now you can really target and message specifically to that person and the state that they're in. If you wanted to promote gift subscriptions, I would use this header bar to promote gift subscriptions for the holidays to anybody who's logged in as let's say a paid subscriber. Right. Run that for a bit and see how that goes. Change your, change your content, your text. Test different promotions. This is a fast place to change things up. Try different promotions, see what works for you. But the conditional display notice is pretty, pretty cool. Okay, targeting. The last thing I have on targeting is our add dropper add on which you can use to really to message on your website also based on your login state. So for instance, you can hide your subscription oriented ads on the site to people that are paid subscribers or paid members. And that's pretty powerful. So imagine going to read an article and I'm just a casual visitor from Google or from Facebook. Or maybe I'm a free registered and logged in user and I'll see a promotion in content or maybe in the sidebar. And that's great. I can, you know that promotion could be compelling and I'll click on it. Could be anything, could be text, could be an image, could be a video. I mean whatever you want in always recommend, keep it clean and simple. And then if I'm paid though and logged in, I won't be bothered. That message will be hidden. You know for mobile, the in content messaging works. And so now you have the ability to show subscription promotions to folks that are not paid subscribers and not bother the paid subscribers. So that's something that Addropper is really good for. Certainly you can, you can use it to run regular ads, but considering it considered a great way to target your casual and your free registered readers. Okay. Anything else on on site targeting we want to talk about or I missed take a sip of my tea.
I think that's good. One thing you we haven't really talked about is offering some kind of like free ebook as well to get people on your newsletter. So sometimes that can be a good way to get people who maybe wouldn't, you know, sign up a different way, you know, as a free registrant. But sometimes just to get them on the email newsletter offering some kind of ebook or access to a download can be a good way to get get even more people on your email list which then use that email list to show them all the benefits you have and encourage them to subscribe down the road.
Yeah, that's a really good point. A download is compelling. Maybe there's a section on your website that you've built specifically for somebody who signs up. Maybe it's an issue using issue m that someone gets for free and getting people on the list, whether it's a free registration or it's a pitch to download something or get sent a PDF via email works really well. And I would say too, if you're exploring Facebook like let's say as for promoting subscriptions, then really the thing that works is promoting something for free because free is very compelling and you want to grab those email addresses, which is the whole point of a free anything in the digital world. So if you have a PDF to give away, test that in Facebook. If you have a section of content that you reserve for anybody who signs up, give that away. You can certainly promote a free registration to get a certain amount of articles for free. And these are things that you can test actual results. You're not just getting clicks, you're looking at, hey, are people joining the email list? So yeah, we haven't even talked about targeting outside your own website, but when you get into Facebook and LinkedIn messaging, think about offering that that thing for free to get to build the email list. And then you can track with UTM codes which you attach to links you can track exactly, you know, how folks came in to claim their your free offer, whatever that may be. Yep, it's a good point. Okay, so let's let's switch to our last segment here. Opportunities. There's a lot of things that you can do with digital that can generate additional income. We talked about gift subscriptions being 20% of paid subscriptions. We talked a little bit about making sure your, your gift button or, or call out is visible on the subscribe page. We talked about emailing and targeting your paid subscribers for. No we didn't, but we should, we should talk about maybe taking donations. If you're a mission based publication, you should be absolutely asking for donations as well as paid subscriptions. You can do both. And we're seeing more and more publishers go after both and it works. Another thing you can do too if you're looking for to test something is you can create a premium plus level. So you have your paid subscription levels but you may be able to charge a little bit more per month or per year if you remove ads, which you can do with Ad Dropper. Now I get a pretty good knee jerk reaction from publishers that say, oh well, no, we don't want to do that. But the reality is, is that your paid subscriber base is, is a fraction of your actual, your casual reader base that come in from outside sources and your free registrants. It's very small. And the reality also, the other reality is that when you have an email address, you're sending people back to your content. They're, you're, they're seeing more page views, not less page views. You're actually growing your traffic with any kind of registration process. Free, Free and paid. So removing the ads. Yeah, technically you are removing some of, some of the ads, but it's, it's very fractional and it might very much. Someone might say, you know what, I don't want ads. That's, that's great. I mean it's a, it's. The banner ad world is a battle of, of attention right now and you have 40% of people using ad blockers. I mean it's very clear the opinion on banner ads. So why not ask a little bit more to hide them? Just get right out front with it. Another thing to do is to, you know, people password share, right? It's like family subscription to local news or maybe it's a magazine subscription. I'm going to send a login to my friend. Why not just move that part of the benefit forward and say hey you. And up to four family members or five family members can gain access to the publication. So you're just having that conversation right up front. It becomes a benefit or feel free to share your magazine subscription with a friend or give a limited access subscription. So another thing we're starting to see is you can create a hidden subscription level, let's say three free, but only three months or two months or some, some period of time of your choosing. And then in the, when someone signs up, they know that they're going to get be able to give away a completely free full access premium subscription or membership, you know, to someone else of their choosing for a couple months, three months, something like that. And so that helps build your email list, helps get your brand out and it really, really takes advantage of the viralness of email, which email's the original viral platform and it's word of mouth. That's what you want. You want somebody saying, hey, this is great, here's a free subscription. These guys are awesome. And then you have a much higher chance of converting that free subscriber. Let's see other opportunities. We mentioned small boats. They have a classified section and if you're, if you join as a paid subscriber, you can post unlimited classifieds. Their classifieds doubled in quantity and their paid subscribers went up just with a simple push. People that came in with boats to sell decided to just become a subscriber and what the heck, and then they could sell their boat and subscribers got that additional benefit of being able to post classifieds. You can do the same with an events calendar, letting paid members post on your events calendar. With leaky paywall and WordPress, since we're all sharing the WordPress user table, it's super easy to turn on permissions for paid subscribers to be able to have access to posting on a calendar or in classifieds. And I've probably missed a bunch of things, but those are what I have as some opportunities. All right, cool. Well, that's it. We've covered the messaging benefits. We went a little deep on, on that. Touch points and targeting some opportunities. If there's one takeaway here for you guys that are still listening, go sit down with a cup of coffee and some quiet, turn off all your notifications and spend an hour just going through the subscriber experience and thinking about how you can onboard that new paid subscriber from the first, your first, their first view of your website and all the touch points that you go through personally when you go in and sign up for free and pay for and pay for your own subscription to understand how, what your emails say, what things look like, is it an elegant experience and, and how does this experience play out over time? So that's your homework. Yep.
Yeah, I'd say a good way to do that too, is what I like to do is have like a keynote or Google Slides or something open and take screenshots of each of the steps of that onboarding experience. So I have, you know, the website, I have the emails, I have all that in one space that I can look through and then start finding one thing in each of those items to, you know, to improve. Sometimes it can feel a little overwhelming. So if you just concentrate on one thing at a time, you know, you can see those, see those benefits ratchet up over. Over time.
That's a great idea. We're big skitch fans around here. S K I T C H for screen share. It's super simple little app you can install on your, on your desktop to do that with. Good idea. Yep. All right. And as always, if you guys are new, if this is a new episode for you, I would recommend to download our subscription accelerator framework. It's available at LeakyPaywall.com grow if you have any questions. I love answering questions, especially questions about growing paid subscriptions. Please reach out to us at infoine101.com z e e n101.com and we'll answer. We'll answer them for sure. All right, guys, thanks for joining and we'll talk next time.
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