31 | How to easily produce a premium newsletter to your paid subscribers
19 Nov 2025 · 24 min
Pete Ericson and Tyner Tyler Channel show how to split a general newsletter into free and paid versions. Tag subscribers in your email system, clone your template, and add paid-only perks like full-text delivery, earlier send times, and exclusive sponsor offers.
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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 Leaky Paywall. Leaky Paywall is the most flexible WordPress subscription platform. Find out more@leakypaywall.com where you can download Leaky Paywall for free. And now for today's episode foreign.
To talk about how to easily offer a premium newsletter to your paid subscribers. And welcome to episode number 31 of the Paywall Podcast. I'm here with Tyner Tyler Channel, and he's from Paywall Project and we're going to talk premium newsletters. Welcome, Tyler.
Hello. Hello. Let's do it.
Okay. So when we were going to record this episode, we were going to discuss how to build a proper newsletter. It really dawned on me that, yes, you need a newsletter as a publisher to drive your visitors back to your website, but what you really need is the ability to target your readers in a nice way.
Better.
And you have two types of readers essentially, right? You have like your free readers and that they're, they're on your general newsletter and you have your paid subscribers. So how do you deal with that? And this is the opportunity where you can provide the right messaging to your free readers and the right messaging to your paid readers.
Right?
Now the problem is that if you have a newsletter like a one size fits all newsletter, you don't really have the ability to message in a really targeted way, which hurts your ability to convert paid subscribers. Right. And what I will say is that if you don't have a newsletter at all, and I talked to a publisher last week who just started paid subscriptions. They have 700 mixture of 700 free registered users and paid subscribers and they haven't sent out one newsletter. Whoa.
Yeah. Yeah. The free registration is virtually, you know, why do it without, without the newsletter?
Right. And, and to be fair, he was very well aware that he start doing it, but, um, I think he just needed to literally kick himself in the butt and say, okay, I need to start sending it out. Busy, you know, starting to, to have some success with this publication. And also was. We talked about automation quite a bit, which we can talk about at the end as well.
Yeah, yeah.
All right, so let me just, let me just dive into this.
So.
So you have, we're going to assume that you have a newsletter and it's going out to all your readers, regardless. What I'm going to suggest here is you start, you split it and this is so easy to do. You can totally automate it. And you absolutely need to do it because you can speak more clearly to your free registered readers and your casual readers, and you can speak very clearly to your paid subscribers. We're going to call that a premium newsletter or paid newsletter. And the paid newsletter trend is, is, is, is, is always worked. And with the advent of Substack and others, the paid newsletter world is really exploding. Creators are, and content producers are, are, are seeing that readers are willing to pay just for a paid newsletter, you know, that has, has that information. And why? Well, because the newsletter is a package of helpful information that gets delivered to you. You don't have to go anywhere.
Right.
It's just that package and, and it works. And it's worked forever in paper, in print, and now in digital. So as a publisher, content publisher, you need to have, and I'm going to argue that you need to have a paid newsletter. And you can take your free newsletter that you have now and very, very easily with just a couple of tweaks, make it your paid and premium newsletter. And the benefit you get is, yes, you get to speak to the free crowd better and you get to speak to your paid crowd better, but you also end up with a paid product, essentially.
Right.
So when you're encouraging your readers to upgrade to pay, essentially, not only are they going to get, you know, let's say full access to your great content, but they're going to get your premium newsletter as well. So they don't just get their free newsletter, they get the premium newsletter. That sounds pretty good, I think. Or call me crazy.
Yep, yep. And the messaging part of it, being able to, you know, send different offerings through the free newsletter, even different content. And the paid, obviously premium, maybe it's whatever it is. So there's not to go too far down a rabbit hole, but there's a newsletter that I follow that sends houses that are for sale that are under a hundred thousand dollars and they're like old mansions in the U.S. so they're like, a lot of them are in upstate New York in the middle of these small towns, and it's something you have to pay for. Could I go on Zillow and find it? Yeah. But it would be a nightmare to go through and sift through all that. And they just send it to my inbox and it's there.
That's right. Yeah. Nobody wants to spend the time to comb through anything.
That's right. I want it to be curated. I want someone to have spent the time on it to save me time on having to go scour the web. And quite frankly, I'm not going to buy a house. Hopefully not in the middle of nowhere, America. But I like, I like the, I like to see them. I'm interested in, in this list. Yeah, for sure, for sure.
And I, I will say that your, your comment about you can offer different content to, you know, your paid subscribers versus free. Absolutely is a strategy. But I, I'm also going to suggest that you don't even have to do that. Yeah, but they're just a couple of tweaks to make maybe one tweak and that's it for. So let's break this down. Let's talk about what your free newsletter looks like and then after that, let's talk about what your paid newsletter looks like. So right now you have one newsletter goes to everybody, right? Your free newsletter should essentially be the excerpt of your articles and the link to your article. So you have your title, you have your excerpt and a link, right? That takes the reader back to your website to read the article. And of course, the strategy here is you want to send this, you want to collect as many free registrations, which we won't talk about in this episode, even though we talk about it in every episode, drive people back to your website, chew up their free allotment, trigger the upgrade to pay message to subscribe, right? So you have your, your free newsletter has your excerpts. And then very critically, let's say using mailchimp or Campaign Monitor or some other email tool is you want to make sure that when somebody registers for free or just, just gets added to your newsletter that the, that person is tagged as free on your, let's say your mailchimp list or whatever list you're using. And that's critical. So this is how you start segmenting the free newsletter. So you know who to send the free newsletter to. That person has to be tagged as free. And just as an aside, like with, with Leaky Paywall, we mirror tag. We, you know, we do tag mirroring. So if someone registers for free, they're tagged as free. As soon as that person pays, the tag changes to paid. So you, when you're automating your newsletter, you know the right newsletter is going to the right type of person, right? Free is going to free. Paid is going to pay now. So you get that free tag. So that's critical. You got it. You have to, that's how you target, right? The second thing you want to do is you want to do it like I have this newsletter up on my screen now, which is from small boats and I'm on their free list and I get, I get their nice newsletter and you can see that there's some messaging on here. Join today and receive unlimited access to them.
Right.
So they're messaging me as a free registered reader that I need. I should upgrade.
Right.
And they can do that because I'm tagged as free on their list. So on your free news, on your, your free news letter, you have a section which promotes your paid subscription newsletter. Only goes to free. That promotions, they're seeing it every time, right? So if it's a daily newsletter, a weekly newsletter, every time you send that newsletter they're seeing all your great content and they're seeing that message to upgrade to get full access.
Right.
So that this is how your free newsletter is. Is coming together. And then, and then another thing, I don't know if it's the last thing, but you probably have some ads and those ads can go into the free newsletter. Maybe it's all your ads. Maybe you have a sponsor. You want to be clever about it and find a sponsor for your free registration, which we talk about a little bit. Which I think you could put a nice package together for a publisher where they could get their branding on the actual free registration form on your website as well as their branding into the newsletter that goes out to free the free subscribers. Now if you're doing that, we have a publisher in Australia that does that. But if you're doing that, I'd love to know about it. Something I don't see very often, but it works for them in Australia. Okay, did I miss anything on the free, like the free newsletter construction?
I don't think so. I will say I had one publisher that I worked with that had like a local bank sponsor their free registration. Yeah. And it worked quite well. They actually, I believe they named the plan after the bank or whatever. So like whatever hometown bank subscription level, kind of a brought to you by kind of thing. And it worked quite well. People, people responded to it and they, you know, got to see the sponsors messaging and. And then I don't know if they actually advertised inside the newsletter or not, but it's quite. Was quite clever.
Yeah, that's great. That's great. I think it would make sense you could do it for a period of time, you know, whatever, whatever, however long your sponsorship runs for. Okay, so that's your free newsletter excerpts. Make sure that all those folks that sign up for free are tagged as free so you can target them. Make sure you have a section that promotes your Paid subscriptions and then maybe have a sponsor for your free. Okay, so that breaks down the free newsletter. Now let's talk about your paid or premium newsletter. This is going to be your new. Yes. So most publishers we work with, when, when I go to their signup pages, you know, they, they, they give you a few benefits. Hey, get full access. Hey, get our newsletter. Well, this is going to add some value to your paid subscription where you're going to be able to promote your premium newsletter. So get full access and get our premium newsletter only for paid subscribers.
Right.
I think that sounds more compelling to me. I know what you think, Tyler.
Yeah, yeah, I like it.
So as a, you know, as a paid subscriber, it's like another thing of value that I'm going to get. And we, as we have seen from print to digital, we as humans love good packaged products like newsletters. So there's value there. Okay, so I'm going to break down some ideas for how you can again, quickly, easily create a paid newsletter. Copy your free newsletter, remove your, your, your messaging to upgrade. Because this is going only to paid, already upgraded readers, right?
Yep.
When somebody pays for this, when somebody pays for your subscription, make sure you send the paid tag into mailchimp or your, whatever email service you're using. And with Zapier and with our mailchimp integration, super easy to do. So somebody goes from free, they change to paid. Now you know that the paid newsletter is going to anybody who's tagged, everyone who's tagged paid. And now your messaging could be specific to your paid subscriber. Okay, in no particular order, here are a couple ideas that I've seen in the past that work. One is maybe you want to offer the convenience of having a full text newsletter for your readers. So I remember, I know I Politics does this where part of their benefit of subscribing is you get a full text newsletter instead of just excerpts. So the feedback they got was, hey, you know, our readers want the morning news. I think they send it out at 6 or something like that. They're getting ready in the morning, they're, you know, brushing their teeth, whatever. And they want to be able to, you know, basically have their phone like on the counter and just start, like read the full article instead of having to like click and log in. Right. And then you can do. So you can do that with this setup because you know, only a paid subscriber gets the full text.
Right.
You don't need to send folks back to your website if they're already paying. But you may want to give them the experience of the full convenience of the full article.
That's, that's super clever too. You cut down on the password, you know, having to log in and people complaining about not remembering their passwords and then messaging your support team and so. Yeah, that's, that's super cool actually. Yeah, give it, just give it to them in the email. Just stop all this nonsense.
Yeah, easy to do. You just, just set up your email service to display the whole article. If you're going to automate it or when you're producing your email, just drop in the full text. Time is another one. So early delivery. I know that politics gets these premium emails out at six or some very early time and then the free registered users, free newsletter subscribers get the news later. So time can be a very simple. And you can schedule, if you're automating, you can schedule when your newsletter goes out.
And for you traditional print publishers who still have the, the E Edition or Epaper or whatever you, you call it, you know, typically you're, you're finished with that a day before it's sent out in print. Send it out early. Send it a day early to these people.
Yeah.
That are on your paid plan and on your paid newsletter. In this case, people will really appreciate that and they'll see a lot of value in that. Being able to essentially see what the newspaper looks before it comes out.
I like that a lot. Special value.
That's good.
I like that. I'll just keep going here. Make sure there's no messaging to subscribe. I mentioned that before. But you, you do have the opportunity to message, to upgrade. If you have another upgrade path for your paid subscriber, maybe it's a different product, a special product. Maybe it's, maybe it's other products that you would buy. You could do that. Or our favorite is donation. If you have a publication that's very mission based and you do take donations, then your paid subscribers are really your best target for having them donate. And this might be a donation campaign you run for a month or whatever, just have it there for a month. But now you know you're dealing with paid subscribers, it's easy to just insert donation messaging.
And if you're doing that you can, obviously you can use leaky paywall to do that. But a very effective way to get people to donate. And it's super simple without any kind of logging in or anything like that. Our stripe payment links, super easy. Create, create a button link to it and it works. People will do it. They can change the amount that they want to give you if they want to. If they don't want to give you 25 bucks, they want to give you 500. They could type it in and. And then off they go.
Yeah, that's a great idea. Do you happen to have a website with an example of that?
I sure do. One second, let me send you a link.
Yeah, take a look. And what that, what this means is stripe payment links is essentially just a single singular purchase through your, your existing stripe account. So you don't really need to set up anything except for the payment payment links. Okay, so here, pulling up the Salem Reporter and.
Okay, that's got to go away. But that's the Pico vortex.
Yes, I know you're migrating. Okay, so here's some buttons. 50, 100, 250, 500. Okay so if I click on 50, I go straight to the stripe checkout. And it's a nice simple form. I just pay and off I go.
And every option, they have the option to change the amount. So if like ah, 50 bucks is not what I want to give, I want to give like a random amount or even more than what's preset for me. You can do that in here. And it's super simple. No logging in. It doesn't mess with their current subscription system inside of leaky paywall. And it works. In the case of Salem Reporter, they were after some documents from the city and it was, I believe it was like 4,000 bucks. They put out a campaign and they exceeded that campaign like fairly quickly. And this was how they did it with, with these payment links. It just worked, worked better than Pico's system. So that's great.
So they're doing some reporting. They had a need to raise money to, to finish their reporting, to execute. Important to the community. That's right. You know what, we need you to look at this, this you know, bad behavior in town. So here's some money to do that. And it worked.
Yeah, they had, they, they had a call to action and a newsletter, you know, letting people know about the situation. I don't know, I don't know if it was the cost of the foia, the Freedom of Information act or what it was. But, but whatever it was, it cost 4,000 bucks for them to obtain the documents that they were after and the public had interest and they exceeded that $4,000amount quite quickly. So.
Fantastic. Yeah, that's great. Stripe payment links. Easy, easy, clever.
Clever. Easy way to get funds directly into stripe.
Yeah. And if you wanted to, if this is. If this is a very regular thing for you and you want to make the donation level sort of permanent and leaky paywall, you can do that. You just create a new subscription plan, call it donations. You can even select a range, like from low to high, how much to donate, and then assign access on that donation level. So you can keep it all in leaky paywall if you wanted to. Kind of depends on your application.
Cool.
All right, so I think that's what I have as far as the free news structure and the paid news structure. So it's real easy to essentially, you know, clone your existing newsletter, change the language for the free subscribers, change the language for the paid subscribers, and you get, you get a. You have a. Create a better experience for both sides. Right. You know, the, The, The. The free readers, you know, they get the newsletter, they get the messaging to. To upgrade. They get maybe the right sponsorship on there, and then the paid subscribers, maybe it's full text, maybe it's an early delivery of the newsletter, Maybe it's a special sponsor. You can, you can target them for donations. And it's. Everyone wins in this. And you get yourself a. You get yourself a premium newsletter to promote as part of your subscriber benefit, which I think is a huge plus. If I were running a publication, then that's. That's what I would do. So I guess I'll go tell Dan at tjourney to do that.
Yes. And for those of you listening who haven't really played around with your newsletter, maybe you don't send a newsletter. Maybe you don't have time for a newsletter. Set up RSS automated sending through mailchimp. You know, maybe it's not the prettiest newsletter in the world, but at least you're sending it out, people are getting the information, and you're moving forward with that. And, you know, maybe down the road, when you do have time, if you ever do have time, you can start customizing it a bit more with. With what Pete's talked about here. Yep.
Yeah. And. And regardless of how much customization you do, you can absolutely target the free with. With the right messaging and your paid list with the right messaging. So you set up two RSST email campaigns. One one that targets your tag free, one that targets your tag paid, and then you have your appropriate messaging on. On each newsletter fully automated.
You know, I think.
You don't think everybody lift a finger.
I think every podcast for me, it comes back to just do something, you know, move the ball forward, regardless of whether you do all of these things, which you should.
Right.
Just getting the ball rolling will. Will get you there.
So, yeah, start. Start with your free and create it. Create a. A paid. It's once you. Once. Once it's done, it's done. Is really very little extra workflow to send both of those messages out. And Leaky Paywall keeps it totally, totally clean with. With tagging, too, so you know that your readers are getting the right the right messaging for your free newsletter and your paid newsletter. Okay, awesome. All right, let's go to work with those newsletters. And Tyler, thanks again. We'll catch you next time.
All right, see you guys later.
Yeah.
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.





