How Often Should You Send Your Newsletter?

So the problem that you face as a publisher that you probably don't already realize is you're not sending frequently enough. I'd say with the hundreds of publishers that we talk to and we look at their newsletter strategy and how frequency they're sending, I'd say 99% of them are essentially not sending often enough. And maybe that sounds a little scary, but it's the truth, and we're going to walk you through.

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A couple weeks ago, I was talking to Coffee Review, and they asked a very, very good question, and I'm going to just read what they actually me. What do you find is the optimum frequency for emails? We're considering how frequently we need to create content, and that struck me as something I've heard before. I don't know if you've heard it before, but I have heard lots of publishers ask, when should I send the emails, how many emails I have this amount of content, what makes sense? And I thought, this is a perfect podcast, and there's some really good answers for frequency today. And Tyler, you being the new newsletter glue expert in the field, congratulations, by the way, on your acquisition.

Yeah, thank you.

I thought this would be apropos to jump into. How about that?

Let's do it.

All right. Welcome. Tyler, let's go. Okay. So the. The problem that you face as a publisher that you probably don't already realize is you're not sending frequently enough. I'd say with the hundreds of publishers that we talk to and we look at their newsletter strategy and how frequency they're sending, I'd say 99% of them are essentially not sending often enough. And maybe that sounds a little scary, but it's the truth. And we're going to walk you through depending on the type of publisher you are and the depending on the type of content you are. Essentially four cadences that are sort of general categories. You're going to fall into one of them or you're going to upgrade your way into the fourth, and that's what we're going to jump into. Does that sound. Do you see that. Do you see publishers under sending? Is that a. Or do you see publishers kind of doing it right?

I would say that the vast majority of paywall projects. Publishers that come on board are not sending a newsletter at all.

Oh, boy.

Yeah, so again, we're dealing with mom and pop types mostly. We have some, you know, there are a few medium to large publishers in our orbit, but even some of the larger ones aren't. Aren't quite doing it right. So, yeah, the newsletters, it's definitely worth a podcast.

Yeah, I agree, I agree. The more I dug into it, the more I realized, oh boy, we really need to talk about this.

Yeah, like, I'll just mention really quick, like, newsletters are so fundamental to a publisher's success. Like, that's why we at Paywall Project felt compelled when the opportunity came about to acquire Newsletter Glue, which is a plugin that you know can be used to send newsletters through WordPress. We were so kind of compelled by that, that fact that it just made sense to acquire the plugin. So that's how, that's how much it means for a publisher's overall success.

Yeah. Fits right into the flow letter game as well. So that's good. All right, so back to the problem. So the thing is, is if you're not sending your newsletter frequently enough, then you're losing out on the ability to keep your brand in front of your audience. You're also losing out on your opportunity of driving way more traffic back to your site, which you should be doing. And you're also losing the whole subscription opportunity of your audience not seeing the upgrade to paid messaging on your website that you absolutely need to be showing them. So again, I said this depends on your audience and content. We have four cadences we're going to talk about. Before we jump into the four, I want to talk about two quick things. One is if you're listening to this and you don't have a free registration installed set up to capture email addresses, then go do that first. Now, Tyler, please give us the quick three sentence description of what a free registration is. If you can do that. That's a big challenge.

Oh, that's a big challenge. Free registration allows for your users to drop off their email in order to access your content for free. And this is more than just the sidebar widget. We talk about it all the time. It will explode your. Your list. Even for smaller publishers, they see significant volume in building their newsletter list. So do that first. Open, open the gate for, for that list growth and then follow these, these cadences.

Perfect. Leak some content. Get people, require people to drop off their email, choose a password, give them maybe a little more, get them on Your newsletter, watch your email list explode. Good. All right. Second thing I just want to mention is something that I see some publishers who are on kind of the aggressive email side of the spectrum is sending too many, too many articles in one email. So I can't remember who it was, but I was looking at a newsletter the other day and There were about 20 articles packed into the news. Yeah. Titles and excerpts. And the problem with that is there's a 20 minute rule that you're breaking if you're doing that. And that 20 minute rule is the attention span that the average person has in their inbox. So let's say I've opted into my favorite enthusiast hobby newsletter or daily news or whatever it is, and I get the newsletter and there are 20 articles in there. Well, the problem is, is I don't have the attention span for, for to, to scan and decide if I decide to read an article because this is an area of interest or two, my 20 minutes is gone. I have to decide what I'm going to read. I'm gonna scan through the stuff. Oh, that one looks good. I'm gonna get in there. I'm gonna get lost on the website and come back. Maybe if you're lucky, I'll read a second article right after 20 minutes. And this is a maximum. I am done. I just don't have the time or space to absorb any more information. So keep in mind when you're thinking about your cadence, that if you're running very, very high quantity of articles in a newsletter, it's really, it's an easy thing just to break it up into more frequent articles newsletters. Okay. All right. On to cadence. All right, so here's the, here's the. Here are the four areas of frequency that and based on the type of publisher. The first one is a weekly, what I call the weekly minimum. Right. So you're a, you're a niche publisher. Maybe you're a solopreneur, or maybe you just haven't prioritized the newsletter and you're kicking out one newsletter per month. Or as Tyler says, zero newsletters per month. Or maybe it's two newsletters per month. Guess what? Way too low. One a week is minimum. Absolutely. Bare minimum. Figure out how to get a newsletter out every single week. You ha. It's the, it's almost like foundational for keeping your brand in front of your audience. Right. More is better. And then sometimes we talk to some really low volume content producers. They have extremely long form, high quality content. They're just not able to Produce as much as they'd like to and that's okay. So what I would suggest there is look at your archives. If you're producing long form content, I bet some of it, most of it is evergreen and you have probably some archives to pull from. So do. Let's, let's go back to what Small Boats Monthly does. They send a newsletter every week or two that has two articles that are related from their archives and that's just a standalone email. It keeps their brand in front of their readers. And most of your readers will not have seen all your articles anyway. So it's almost like new articles are showing up in their inbox anyway. So that's the weekly minimum sort of level. One publisher figure out a way to get it to weekly, look at your archives and Tyler, is it okay to send just one article in a newsletter?

Yeah, I was going to mention that we have a lot of low volume publishers in small towns and maybe they don't have as much content as some of the weekly or daily news operations. They will send out a newsletter whenever they have a news story. And so that newsletter will just contain one piece of content, which is totally fine in a small town where there's just not a ton of content. So don't be afraid to fire out a newsletter when you've got a new piece of content because again, if you're a local news publisher, you're likely the only source of what's happening in, in the community. So treat it, treat it as that, you know, as that gold in the community.

Yeah, Send an image, send a longer excerpt.

That's, that's precisely what they do.

Yeah, yeah, yeah. Find a sponsor, absorb some room. My dad always said nature abhors a vacuum, which is really the truth. So if you have space in your newsletter, you know, it'll get filled once you start thinking about it, especially a sponsor, it'll fill. Okay, that's. So the weekly minimum is the one. The second level is sending your content two to three times per week. This is a pretty typical cadence for like enthusiast sites that have a steady flow of new pieces or sections. So it could be like sports or hobby publications. Magazines always for some reason fall kind of into this category. Politics, like Monday, Wednesday, Friday, stuff or culture. It could be, you know, local cultural, like a city magazine or food. This, this cadence is a pretty typical one and is good. So if you're, if you're in any of those categories of publisher, you should be at the minimum aiming for two to three times per week longer form content. You probably don't have as much as like a Daily News publisher does. And two to three is pretty good. One is. You may be doing one. I hear a lot. Oh, we're doing two a month. We're doing one a week. It's not enough. Again, go back to your archives. If you need to pull those forward, make them related to your new content, and what you'll see is, you'll see that brand get in. You know your brand, get in front of your readership. You'll send a lot more traffic back to your website and that'll trigger the upgrade messaging for paid subscriptions. And it's. It's kind of a. I don't know what you think, Tyler. I feel like it's a. It's a simple formula.

Yeah. The incentive is more emails equals more conversions ultimately. And so think about it in terms of a profit motive. There it is.

Yeah, exactly. And there's data. I did some research pre this podcast and there's plenty of data that supports the frequency of emails. And the overall cadence of emails is growing. Like we're almost. Especially when we pay for something, we're almost expecting to get some. Some more volume. It's like, I want this. Here's my money, Give me more. You know what I mean?

Yeah, right. For sure. Yeah. And I'll be. I'll be honest. I've never met a publisher who's over sending. Yeah, that's right.

Yeah. Cautionary tale, though. I'm glad you said that. Cautionary tale. There is. There is one very clear line that can fall into over sending, and that's sponsored emails.

Yeah. Yeah, that's. Now that's a different story. Sending promotional content that is strictly and only promotional, red flag right away and can actually have a lot of damaging effects on your domain's reputation with whichever email service provider that you're using highly recommend not doing that. It's a quick way to get yourself in some trouble. But what do you recommend, Pete, in terms of actually sending that promo content?

That's a really good question. I'll just finish that by saying that is the fastest way to get unsubscribes if you really want to get people to unsubscribe. So there's no hard rule for this one. This is essentially, you have to earn the trust of your audience and deserve the ability to send them a promotion. And then you need to be very careful with your promotions to make sure that whatever sponsor article you're sending adds value to your reader and is a match for your brand. And it's something that you genuinely are enthusiastic about. So when you're helping or writing this article for your sponsor, that. That natural enthusiasm just pours out like, this is a great. Yeah, we use it. Yeah, this is sponsored. But, man, we're doing this because we love it. Like, that's kind of the vibe that you need to be sending. You know, the. The fisherman is a good example of this. So they're a magazine. They cover fishing up and down the Eastern seaboard in the US and they do a fair amount of sponsored content and they send sponsored emails. But you know what, they are enthusiasts of the, you know, the fishing gear that they promote, whatever it's gear or boats or whatever it is, they. They are truly, truly excited about promoting stuff that they like. And that's really where you have to be. Okay, good question. That's another podcast. I just did it. All right, so. All right, we've talked about two cadences. The weekly minimum, the two to three times per week for the sort of magazine enthusiast, maybe niche news type of publisher. Then we get into the daily. Right. Daily email sense. This is very typically, as you can imagine, daily news. Right. And the idea is, yeah, frequency news happens, news happens quickly. You want to get it out. And I would say at a minimum, if you're a news publisher, local news, regional news, you need to be sending out a minimum of a daily email minimum. What do you think, Tyler? This is kind of your wheelhouse in terms of working with news publishers. I mean, you have a range of publishers too, from the small to the bigger.

Yeah. Sending daily is when you compare it to those that don't send or to those that only send once or twice or even three times per month. The data is very clear on this. In terms of traffic, in terms of conversions, in terms of. In terms of retention of your customers. It's very important. People don't think too much about that when they're sending a newsletter. It's very important for your retention to keep your brand in front of them. So they think, oh, I see my. My local news, oh, yeah, I pay for it. But they're seeing that and they're thinking, yeah, I'm getting my money's worth and there's. There's value in that. So, yeah, sending. Sending daily. Again, if it's only just one article, it's totally fine. If it's multiple articles, totally fine. Yeah, the more. The more the merrier in that. In that regard. Not maybe not sending three times a day, but once a day at a minimum. For, yeah, I Think is a good general rule for, for anyone that can get to that level with their content.

Yeah, yeah. And it gets into this daily frequency for news publishers, gets into driving traffic. So you're sending every free registered, every paid subscriber back to your site. You're literally swarming your own site with traffic. And that gets you off of the social media and co treadmill. That's sort of a dangerous place to be. It puts you in control of your own audience. And then the second thing is that sort of rise of traffic triggers the upgrade messaging to your paid subscriptions much more frequently. And that's really the game. Cause you need for readers to turn into paid subscribers. They need to see upgrade messaging. You know, the statistic is somewhere around 13 or 14 times before they convert, before people convert. And so you need to show that upgrade messaging frequently. And that's done through your daily news. Okay, now let's talk about multiple times a day at the fourth level, the fourth cadence. And we do work with publishers. And I know some of you might be listening to this and thinking, oh my God, that sounds, that sounds horrifying.

Like so much work.

Oh my God, it sounds like a lot of work. It sounds like a lot of spam in my, in someone's mailbox. But it's, it's not. And so how, how do you handle this? So now first of all, multiple daily emails is usually when, when you're dealing with news of some kind that, where the, the volume is just enormous. Right. Uh, I mean, New York Times is, is the obvious example. Uh, I probably get push notifications. I'd say, you know, six, seven, eight a day. I don't really count, but a lot, maybe even more. I don't know. I'd say their push notifications are certainly more frequent than the emails that they send. But breaking news is really part of that. So if people are opting into breaking news. Yeah. Give it to them when it breaks. If it's something that's very segmented, like a re, like region or topic, like a category of news, sports, or maybe it's real estate or whatever. I've opted into. Yes, send that frequently, multiple times per day. Note that I've used the word opt in in this description. I'm actually gonna switch, switch to. So this publisher here, they have some on checkout and on my account page. They have regions here in Mexico that you can opt into when you check out. Now this is telling the publisher that I want news from these areas. This is my interest area. It's custom to Me. And so I will absolutely stand to have more frequent news sent to me because of this. Now, let's talk about automation a little bit, because you're freaking out. You're thinking, I can't do all this. This is not possible. How is this possible?

Right.

I have a small team, even a big team. It's like, this is a lot of work. So, Tyler, how do we automate this? How does this work?

Well, since most of the publishers that we work with, well, not most, all of them, are using WordPress, which means that all of your content is in one spot, you can set up automations in WordPress that will send out emails to specific groups of people, whether that's in mailchimp or Flow Letter or what have you, that go out whenever there is new content in that particular category. And so in the example of what we're looking at here on, on the screen, which is Mexico News Daily, they've got eight, nine different, whatever locations. Whenever they post content about Southwest Mexico or the Gulf side of Mexico or the Yucatan Peninsula, that content will be fired out in a, in a newsletter, in their case on the weekend. So if you want news about those regions, you'll automatically get that. And Mexico doesn't have to do Mexico News doesn't have to do anything special other than just post their content and ensure that it's in the correct category that they want it to be in.

Category driven.

That's it. So it's all category driven. Nothing changes for their workflow. People get to decide what they want. And because they're using. Let me just go ahead and shamelessly plug Newsletter glue. Because they're using newsletter glue combined with Flow Letter, they're able to pull off this automated newsletter system that requires no additional work because they're in WordPress and because they're using this one cohesive system.

Yep. Nice. Yeah. So opting in gives you the right to send more frequently because your readers are telling you do it, and then you automate that. Mailchimp will also automate your. If you're using mailchimp, you can use RSS to email in mailchimp. It's. It's a little prehistoric, but it does work and it does do the job. And if that's your only choice, then absolutely do that. Because you want to drive, you want to get the news in the box, you want to drive the traffic back to the site, you want that your brand in there, you want upgrade messaging in there, you want all that good stuff. Yeah. Yep.

And that's, that's the that's where the beauty of using Newsletter Lou comes into this is that you're using your existing WordPress data to automatically create this. See, there's a lot of design control over the output. So that RSS feed. Yeah. If you're using that, continue to do it. Like don't turn it off. Keep, keep that rolling. But just know that there are better alternatives if you're in the WordPress ecosystem to make that look and feel better connected to your overall brand.

Yeah. Yeah. Reach out to us if you want to dive deep into, into this one category of publisher I will make a shout out to is the sports publisher. Now we are obsessed in, with sports in general as far as humanity goes. I think we have a special level of obsessed in the United States with sports. And if I'm tracking a team, it doesn't really matter how many emails or notifications I get about my team because I want them all I to be first to get them. I want to know exactly what's happening every minute of every day with my team. And I speak from experience. So we did a project with a Pittsburgh sports publisher years ago and we built an app and I remember having a conversation with him because he was sending 11 to 12 push notifications a day about the various sports teams in the Pittsburgh area. And you know what he said? He said his readers wanted more.

I am not at all surprised. As someone who lives about an hour south of Pittsburgh, who's in the city often, I am not surprised by that. Pittsburgh's a big sports town. People love, love their teams up there.

Absolutely. Absolutely. So if you're in the, if you're in the tracking sports teams universe, then you probably need to just pour a little extra gas on your emails and your notific.

For sure.

I'll leave it at that.

Yeah. I would say one other use case too for the sports also the financial publishers who are, you know, maybe you're, you're writing about stocks and, and things that are, are, you know, people want to know about right away. Yeah. Give it to them as often as, as you can. As often as they want. For sure. That content. So yeah, there's any of those kind of frequent high volume type content types are ideal for this.

Yeah. Finance of course, you want the information right away as stuff breaks, especially if you're in the trading game. We work with several financial publishers and they have a lot of them have multiple newsletters, so that's very typical. And multiple paid newsletters. So one I'm thinking about I think is nine paid newsletters and their average reader subscribes to several of them. So there's a, there's a constant content blitz. But you're talking money, you're talking about being in the business of finance. You need this, you need this data. This is what you signed up for. Yeah. So. All right, Tyler, thanks so much. I think this covers it. We got the four cadences, we got the, the weekly minimum. So if you're not there, make sure it's once a week. Work on your archives. You have the two to three times per week you have enough content. Maybe it's long form. Your, your niche publisher. Two to three times a week is a, is a good cadence. If you're in the news game. Daily, daily, daily. And then if you really want to up the game, make sure you give people opt ins to opt in and then automate categories of your content. Could be by location around your town, by like towns around, around your city. It could be by category of content. But if you give the opt ins, you'll reduce your churn because people are giving you permission to email all those categories. All right, very good. And then a quick shout out to Newsletter Glue, which as mentioned earlier, Tyler has Paywall project has acquired and that makes, is going to make this better. Makes Flow letter better. Makes everything better. Everything's better with newsletter Glue. I'll end on that.

Thanks, Tyler. Catch you later. 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.