How to setup a successful holiday subscription promotion + results (Part 2 of 3)
19 Nov 2025 · 20 min
Pete Ericson and Tyler break down holiday subscription promotions that work. Dominion Post converted 4-5% of free registrants to paid subscribers via Black Friday email. Salem Reporter's $10 for three months trial converts at over 60%, and habit formation takes about 66 days, so annual plans discounted work better than monthly.
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Episode 51
December 14, 2023
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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 and now for today's episode.
All right, welcome everybody. Welcome to episode number 51 of the Paywall Podcast. I'm here again with Tyler. Tyler, welcome back from Tyler, Thailand.
Thank you very much. It's freezing cold. What have I done?
Awesome. Well, maybe not awesome, but welcome back.
Thank you.
And today we're going to talk about how to set up Black Friday promotion and the results of a Black Friday promotion. And really you can apply this to any kind of promotion that you want to provide. This will be part two of a three part series. Our last podcast was about 10 promotion types that we approve of. We're not big fans of promotions. Of course, when you're in the B2B space, promotions get a little more nuanced. But in the B2C space, like a local news, the data doesn't lie and we are having success with it. And we also look outside at what other publishers are doing. So I thought I'd actually jump into that. Jumping into an article here on toolkits.com which is a great. Jack over there is doing a great job. Might want to sign up to their newsletter. And this one is about some data about promotions. So they did a study of over a thousand consumers who were subscribers and 73% of them said that they're more, more likely to subscribe when offered an introductory discount. Now that's a pretty big number. And 76 said they're more likely to subscribe if a free trial is offered. So about the same. Whether it's an introductory discount or a free trial, there's a big number that said, hey, yeah, they'd like to jump on that. Now here's an interesting one. I thought we could talk a little bit about the free registration. 54% of consumers also said they're more likely to subscribe if a publisher has allowed them to access some content for free. So meter your content, offer a free registration, you know, start, you know, give a little content away for free and that will bump up your, your conversions as well. And finally, 60% of consumers said, yeah, we'd like to subscribe if canceling was easier. Which is kind of crazy in my book because yes, of course, canceling should be a one click process. Now, just a little more data. Where's My other, my other data piece. This came from twipeonline.com just thought I would, I would round this out. They came up with some, some other interesting data. What you're trying to do here with subscriptions is create a habit of paying. So if somebody is not a subscriber and you're, you want them to become a subscriber, you basically want to create the habit of them paying for your content. And the, the, this data point keeps being pushed out, but apparently it takes six days now to form a new habit. You need to do something for 66 days to actually create a habit today. That was from an article from tw. Whether you believe it or not, it's, it's still accurate, you know, philosophically speaking, because yes, we are humans, we are creatures of habit. And creating those habits is really, really, really important. If you can get somebody to, to read and enjoy your publication and pay for it every month or every year, then that's, that's the end goal. They reported also that about 50% of publishers had price increases over the last year, which seems to kind of line up with what we're seeing with our publisher base. For sure, if you haven't raised your price in a long time, it's time to do it. You probably would be able to to get a 20% bump in your pricing without too much pain from your existing readers. Take a, it's a good time to take a look at. It's the easiest thing you can do to bump your revenue. It works every time. And then the last couple of tidbits is 71% publishers sold an annual plan when they discounted it. So that was, that's pretty interesting. Annual plans do seem to outperform monthlies. But we'll talk about both on this podcast and surprise, surprise, younger audiences react to discounts very favorably. So if you're going after a younger audience, then this, you know, some kind of discounting promotion is probably in your future. Okay, so let's now talk a little bit about one of our clients, one of your clients, Dominion Post. And they had a Black Friday offer. I know there was some sort of setup in front with the free registration. You want to kind of walk us through what happened with their Black Friday promotion, who they are and what they did.
Yep. So Dominion Post is my local newspaper here in Morgantown, West Virginia. It's a college town, 30,000 people, maybe 50 or 60,000 people when the university is at capacity, which is the land grant institution of the states, the state's university, West Virginia University and they have, they recently set up a free registration on the site. So one article for free for anyone who visits the site, the second article is going to prompt you with the option to sign up for free. You get that free article and at which point you're then prompted to like we talk about all the time, you're prompted to upgrade. They cultivated a free registration list of emails over the course of I don't know how many months, maybe just a couple. It's not been that many that, that long, maybe two months, three months. And then they took that list that they were able to cultivate from their, you know, their pre registration setup and then remarketed back to them during Black Friday to see if they could get them to convert and pay. You know, of course these free registration people are seeing offers after that first article, but sometimes like we said 66 days, like it could take a while to get these folks to convert. And so one way to nudge them over could be sending them an offer during Black Friday. And it proved to be pretty successful at getting people to, to sign up to pay. Cool.
Cool. So do you know what percentage of, of those free registered readers converted?
I think somewhere around 4 and 5%.
4 and 5%. That is a, that's a, that's a nice conversion rate. Yeah. So they literally just started with the free registration they've been running for a while. I think they're. Newspaper's been around for a long time.
Oh my gosh. 1800s.
1800S.
Okay.
Two months ago this veteran newspaper set up a free registration on their site and then ran a, and then ran a Black Friday promotion against it. And they got 4 or 5% of those free registered readers to pay basically. And I actually have the promotion. You sent this to me, Tyler. But yep, I have. This is the email, correct?
That's right.
Okay, so if you're listening, I'm going to describe what this is, but it's essentially a very graphically oriented. It's a pretty email. It's blue and yellow. Go Sweden. And they have, they have there a lot of words on here also, I'll put it that way. And you know, quite frankly I think it's pretty to look at, but I think it's really a pretty, not a great promotion. It's, it's, there's a lot, there's, it's very busy and it's hard to see actually where the promotion is when you first look at it. There's the only thing I, I gravitate towards is the subscribe now button at the bottom, which is great thumbs up for having one subscribe button. But to actually figure out what the promotion is, I have to spend quite some time looking at it. Right in the middle is a $36.50 for the next 12 months promotion. But it's, it takes a lot of words to get there. At the very top. Get a one year digital subscription for Dominion Post for only 10 cents a day. Yeah, that could be a little, a little cleaner. But even with this not so clean promotion, they actually did pretty okay with their, with their. So that argues one, get that free registration going. If you have not set it up, you are missing out on revenue, period. Yeah, that, you know, you're, you're asking somebody to fill out an email address and choose a password to get that next article and get your newsletter, which is essentially what a free registration does. And that means these people have typed a password, they're read, they're logged in, they're, they've registered on your site, they've, they've jumped the extra, you know, bar to do this. They're, they're primed for converting. And then the Black Friday deal did some nice conversions. Now I'm going to take a look, we're going to take a look at what the Wall Street Journal did for their Black Friday or they called Cyber Cyber Week or whatever they call it. And you can see that the way that the Wall Street Journal handles it is quite a bit cleaner. I would just steal this type of promotion, make it an email. The biggest thing you see is $1 per week for one year. It's very clear, your eyes go right to it. And then there's the subscribe now button right below that. And that's essentially the promotion. And they have, they have a bundle going and such. And then when you hit subscribe now, you go to the registration page where they have again, they have the, they have the, the price, $1 per week. Big, big and bold. And then they cross out the original price. Just, that's another good tip is have your original price there and put a line through it so people can see what the difference is between the retail price and your promotion price. Okay. And then off you go. So that's, that's, that's pretty, that's good news. So they're, they're tiptoeing into the waters of, of running promotions against their free list.
That's right, yeah, yeah. And I commend them for not going down the rabbit hole of 99 cents for one year. They, they certainly discounted Their, their yearly price, which I think is 120 a year, so.
A quarter.
Yeah. So I mean, they've discounted it quite a bit, but they're not doing the. What's, what's the way to describe that? The Scam Life.
The Walmart price strategy.
That's right.
Price strategy.
Yes, yes. So the value is still, is still there. And people aren't assuming that your content and your journalism and everything that you offer is only worth a dollar a year. So I expect that they'll have a lot of these, maybe more than half will probably convert, like at the end of this paid trial, at the end of the year. I suspect a lot of them will do because that's. And that's common for a lot of the local newspapers that I work with, you know, the Salem Reporter, as sort of a ongoing promotion that they run virtually all year long. And the conversion rate is great.
Let's talk about the Salem Reporter. So that's a good segue. So if you're thinking about doing a monthly promotion versus an annual promotion, the Salem Reporter, they haven't, they haven't done it. A specifically Black Friday sale, like you said, this is a. I think they've been running this promotion for.
Since they started with me, even before me. I think they were, they were running this promotion with their previous vendor.
So a year. Has it been over a year?
I would, I would, I would say so, yeah.
Okay.
They actually had an update. They actually had an uptake on Black Friday too. I guess people saw it, just assumed that it was a promotion. Interesting. Yeah, interesting.
So let's, let's take a look at it. If I hit, I'm on the sale reporter. If I hit the subscribe right up top. Just, you know, nothing special, just a subscribe link. Yeah, I get the singular focused. And their, their promotion is a real. I think it's an excellent template for a monthly promotion. Yeah. You want to, you want to dive into it.
Yeah, yeah. So this is essentially their $10 for three months of access, which then after three months converts to a monthly $10 per month set up. And I think. What do we call this with leaky paywall, it's like the trial subscription delay.
Oh, it's a trial delay. Yeah, yeah, yeah.
So it's super, it's super easy to set this up. And leaky paywall, despite how complicated it sounds to change the time frames from three months to one month. But this works. It works really well for them. They, they have a lot of people that sign up for it. And the Conversion rates after three months are, are quite high for, for this particular promotion.
Yes. That's a really interesting piece of intel. We, we were talking about that the other day. The conversion rates. I seem to recall it was like 60% or more or something like that.
Yeah, it's, it's high. It's higher than you would assume for, for something like this.
Yeah.
And again, I think that's because you're putting down 10 bucks. You're, you're getting people into that habit forming. We're past the 66 days. Like, you're, you're 90 days into this and you're probably, if you're still, after, after 66 days, you're still into this and you're still reading it, you're still getting the newsletter. You're, you're getting the premium newsletter. It's going to be hard to stop that after, after 90 days. And so 10 bucks, you're already used to the $10 figure. Even though it's going from $10 every three months to $10 per month. That number looks the same, feels the same, even though the time frame is different.
Well, I think you nailed that. The psychology of that. $10 up front and $10 per month. Like if, if you're charging $5 for your, for your month, you know, do the $5 for three months and then charge. Yeah. The per month. Yeah.
Try to keep it, keep it the same. Because if people start to see the difference, they're going to be like, oh, oh my gosh, it went from $10 to $12. I can't, I can't do that.
Yeah, that's very clever. I think it's brilliant, actually. I think, I think if I were to do any kind of monthly promotion, this would be exactly the way to do it. So, yeah, you're discounting, you're appealing to younger readers. You got the 66 days habit formation under your belt. Of course, you could on a Black Friday, you could use it on a Super Tuesday, whatever you want. Yeah, it is. That's, that is. And, and to have the conversion rate over 60%, people that basically stick around. Yeah, that is amazing.
Yeah. And, and the reason, and the reason that's so high, I mean, I'm sure people are thinking like, how do they manage to get that conversion rate to be so high? The reason for that is their two newsletters are just, they're reliable. Like, they're, they're really deep diving into local journalism in the community. And they have the premium newsletter which adds just a little bit more for, for that Premium subscriber. So you're getting a lot for. For $10 a month, especially $10 for three months.
Yeah. Just a quick note on that premium newsletter. So what they do is they have an afternoon edition, which is essentially sending out the articles that were published during the day in the afternoon versus sending them out in the morning. So, and correct me if I'm wrong, there's really no extra workflow for. For them on having a premium newsletter. Now, their. Their upgrade messaging isn't on there, which it is on their free newsletter, which it should be. But other than that, is there anything that takes more work?
Not. Not really, no. No. And I'm not even certain that they send it out every single day. But it's just a few extra stories. They're not. They're not doing full text, giving everyone, you know, the ability to read the full story in the email. It's just a matter of a little extra content that everyone else maybe did not see. And that free newsletter.
That'S awesome. We did a podcast on that. You can go look for it.
Yeah.
All right. I think that wraps up this particular topic, this Black Friday topic. If you are a. If you favor annual promotions, you have a model for. For running an annual campaign. If you favor monthly. Monthly subscriptions, I should say, then you have a model for that. We do see more readers take annual subscriptions. That sort of. That matches the data that Twipe came up with. And so if you're struggling between, geez, which, you know, should I lean into annuals or should I lean into monthlies? Lean into annuals. In fact, this link at the bottom of the Salem Reporter here, this, which does get you an annual subscription, actually outperforms the monthly by a small percentage, and it's just a tiny link. So anyway, next podcast, we're actually going to talk about Facebook promotions. That'll complete our 1, 2, 3 series. The first, the last part one was all about the 10 sort of a wide net of promotion types that actually work that. That work well. This one's Black Friday or really any sort of specific targeted promotion. And the next one's going to be. Is super interesting. And this one is about to put Facebook to work and run promotions for you. Thank you, Tyler.
Thank you.
Stay warm. Think of Thailand.
Thanks.
All right, see 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.





