The Newsletter Retention Playbook Every Creator Should Know

VIDEO - 30DOG Recap #2 (Engagement & retention)
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Chenell Basilio: [00:00:00] It got 15% of his readers to reply to his emails

I think one of the problems people have with welcome emails is they make

Dylan Redekop: This is just one of those little things you can do to, increase some retention in your newsletters

Chenell Basilio: he said like 40 or 50% of people click that link, which is huge

might make you think twice about unsubscribing.

Dylan Redekop: I'm like, Ooh, this wasn't a good experience for me yet. I'm doing the same thing to my subscribers.

Chenell Basilio: those two combined is like a really powerful way to turn someone who might be a very, loose follower into a more robust subscriber.

Chenell Basilio: Welcome back to the Growth In Reverse podcast. I'm Chenell,

Dylan Redekop: And I'm Dylan.

Chenell Basilio: Today we're gonna talk about engagement and retention for your subscribers. I think this is one of the topics that most people don't think about, but when you spend that much time trying to get subscribers, you probably wanna keep them sticking around, keep them happy and reading.

So we're gonna walk through some ideas for exactly that and how can you keep those new and existing subscribers

happy and reading your content.

Dylan Redekop: Yeah, just think about it like every [00:01:00] time you send an email you get unsubscribes, but what if you got zero unsubscribes? You're virtually growing your newsletter. Right? So I mean, if you think about it that way, this is like. This is a no brainer. People should really focus a little bit more, I think, on engagement and retention than just always trying to get that new subscriber.

Chenell Basilio: Totally. And yeah, stop trying to get more and more try and keep the ones you have happy they're already bought into your message and what you wanna talk about. So yeah, just keep keep doing that and there are a couple of strategies you can

use to make those work better for you.

Yeah.

Dylan Redekop: I got a quick question for you before we jump

in. This is off the cuff. What percentage of your time should be focused on growth and promotion, and what percentage of your time should be focused on actually writing, creating the newsletter?

Chenell Basilio: I am probably an anomaly. I would probably say 80% of your time on the content, if not more, and like 10 to 20% of time

on retention and growth or on growth. Um, I think. Because I think content, [00:02:00] it does two things, right? If you spend more time on the content, not only are you making your current subscribers happy, but you're also able to get new subscribers.

Because if someone sees a really good piece of content, they might share it. And that inherently is a growth tactic in itself. And so I think that the more time you

spend on content, the better off you'll be. And I usually see people doing the opposite. I would probably switch those, especially if you're going through like a growth plateau or things aren't working the way you want to.

I think if you spend more time making the content better, more exciting, more enjoyable for you to create,

I think

there's something beneficial there.

Dylan Redekop: Do you think it's possible to create content so good that you can do 0% promotion aside from just sending your newsletter and still grow?

Chenell Basilio: No, I think after, in the beginning,

no, I think after you hit escape velocity, you can probably really lower the amount of promotion you're doing and still grow. But in the beginning, like no one knows who you are, so you have to at least get, 5, 10, 20 people reading it. And then if the content's that good, they'll share it with one person and so on and so forth. But [00:03:00] if you don't share it with anyone and you're just like hoping and praying that someone comes to read it,

It's probably not gonna work out well.

Dylan Redekop: I agree. I think it's still important to, at all phases, to over and overindex on quality of the content we've talked about. You've talked about insanely valuable content a bunch of times before. You've basically are trademarking it at this point. Make sure your content is insanely valuable, and that'll just really dramatically help with engagement and retention and even growth.

But if you've already got that nailed and you want some more strategies, let's talk through some that we've got to share with you today.

Chenell Basilio: Yeah, totally. Cool. Yeah, I'm excited about this and we'll have to do a whole insanely valuable episode, but

for now, that was a little teaser.

Dylan Redekop: You go.

Chenell Basilio: There you go. All right. So I think the first one comes from again, the 30 days of growth. That, that I did that. We haven't shared

these on the podcast, so we thought, why not?

Let's do it. Jeff Felton is a friend who really over indexed on figuring out welcome emails and like, welcome sequences. And so I had him [00:04:00] come in and share his strategy. He calls it. Actually, I think I might called it the icebreaker method, but essentially it It got 15% of his readers to reply to his emails. And I love that because most people, a don't even know what the percent of replies that they're getting is because it's a manual calculation you kinda have to do. But he, he did know that number and I love that. And he says essentially what his strategy was, was in the welcome email ask a very, simple, but. Specific question with like, yes, no true false answers. You can even do multiple choice, like, hey, reply A, B, or C, depending on what your situation is. So for me, I could say, Hey, um. Hey, reader, really curious about where you're at in your journey. A you're just starting out or don't have a newsletter yet.

B, you've been going for six plus months, but you're still trying to grow, get your growth trajectory going or whatever. And then c, you're a seasoned, you're seasoned at this and you know what you're doing, and you're just looking for a few tips. So they just have to hit like [00:05:00] reply and say A, B, or C.

They don't have to think about the answer. They don't have to come up with some story

or think too hard about this. It's just very simple.

Dylan Redekop: Low friction, right?

Chenell Basilio: yeah, to do super low friction. I think one of the problems people have with welcome emails is they make the question they ask so complex.

It's what's your biggest problem right now? Or which is super open-ended you're asking someone to think through their situation, craft a response. And so I think some people ask two or three questions, which is also not beneficial because

I'm gonna get overwhelmed and probably answer none of them. So I think those are some of the things. It's like making the questions too open-ended

or asking too many questions.

Dylan Redekop: or

Too difficult of a question to answer that requires maybe too much thinking. One thing you said there was what's your, the biggest challenge you're facing, which I think is like better than what is a challenge you're facing right now? If you can kinda like. Have this priority of, the way you want somebody to answer it, like your most challenging issue right now or in the last year or whatever that [00:06:00] might be.

That's helpful. But I think being more focused and having more of a closed ended question that still benefits you, but gives the reader more time to answer is really helpful. One thing I'll just add onto when you're asking questions that I've seen, somebody share that I thought was really smart was they asked the question.

So the question, for example, Jeff gave some examples of like, what kind of business do you run? And then instead of just leaving it like that. You could have like a multiple choice option, or if you just wanna leave it as text instead of like a poll or, or other options.

You could say, are you a solopreneur or do you run like a small business? Something like that. If you wanted to get some more information or are you in tech or are you, you know, brick and mortar, if you're like focused on maybe like commerce or that sort of thing so you can like tag on. A second part of the question that just helps guide people or it's like, what's a big challenge you're having right now?

And instead of people being, geez, I don't know what, everything's a challenge, you could say, is it growth or revenue? And then you're kind of giving them one of two buckets to play with and they [00:07:00] can more easily reply. That's very similar to saying like the a, b, C kinda option. But, uh, this is just another way I've seen people frame it that's been apparently very helpful and gotten more replies than their usual.

Just What's the biggest challenge you're having right now?

Chenell Basilio: Yeah. It's funny because if you look at any like email marketing person that's like, I'm gonna help you grow your email list, most of them will say, ask your readers, what is your biggest struggle you're having right now? And it's like. Yeah, but that's takes so much brain work and like, I do wanna ask that question eventually, but if the goal of this email is to get the most replies, like maybe we should do something that's easier for people to answer. Uh, a little bit more straightforward. A a little twist on this, um, Jay Clouse from Creator Science, actually, he started asking, um. If I were to record a podcast episode specifically for the biggest thing you're struggling with right now, what would I make that episode about? And so it confines you to think of one specific thing.

It's still a little too open-ended for my liking, [00:08:00] but I think it's a much better like reframe and you're getting people to visualize what the output of this question's going to

be. So I like that one too.

Dylan Redekop: The frame was the word I was thinking of. It was like, it just puts you in a different perspective of like just randomly thinking about your day. And it's like, oh wait, if I'm scrolling Spotify and I see a podcast episode, that title just jumps out at me. What is that title? That's, that really helps you synthesize the challenges you're having and helps Jay figure out exactly what kind of episode he should create or what he should talk about. So I really like that idea.

Chenell Basilio: We're on the same topic of a welcome email, I wanna go to to talk about Tom Alder's welcome email, which is like one of my favorite ones. He writes a newsletter called Strategy Breakdowns, and his welcome email is so simple. It's just like really basic. There's like maybe six lines of text and it's Hey, I'm Tom, and there's a picture of him waving and then it says oh wait. Do I have it open right now because I'm gonna forget the exact thing. Oh yeah. Hey, from [00:09:00] Sydney, it's Tom here. Thanks for subscribing our case Studies will help you level up your strategy skills in just three minutes a week to complete your signup and get tomorrow's case study. Do these two things. One is reply to this email with the word hey, which he's trying to get a reply. Two is click this link to confirm your email. And so I think he said like 40 or 50% of people click that link, which is huge because on the next page he does something super smart, which is giving away a piece of content and he walks you through his first case study. And so he is keeping people in his orbit, his ecosystem, and this, the welcome email is super simple.

He doesn't give you a ton of stuff to. To do. He's not trying to tell you his life story or why he started this thing. It's just like very basic because he knows he can get into that in future emails. And so I really like this like very specific, call to action here.

Dylan Redekop: It says he gets 47.4% total click through rates on. The welcome email. So that's pretty [00:10:00] solid and 45.1 of clicks go to a full length case study.

So really solid numbers there. The prior version was 23%, so he is essentially doubled. Doubled his click-through rate by making it short, concise, and offering Hey, if you click through this to confirm, you also, I think, does he tease that he gets that?

He'll, you'll get a lead magnet if you do those things. Yeah, it does. Our case studies will help you level up and you have to get, you have to do those two things to get them

Chenell Basilio: Yeah, but he says to get tomorrow's case study,

but what you don't know is when you click that email, you're gonna get one right

now. So it's

interesting.

Dylan Redekop: yeah. Huh. I in that link that. The click this link to confirm your meal takes you right to that case study, right?

Chenell Basilio: Exactly.

Dylan Redekop: Dang. I love it. It's it's a little different. It's a little different than we've talked about Katelyn's reverse, Kaitlin Bourgoin's, reverse growth lead magnet, sorry, reverse lead magnet where she's like, do this so that you get this thing.

He's almost like he's saying, yeah, you're gonna get tomorrow's case study, but he's surprised and delighting you a little bit by, if you click that link, you get one, like right then and there, which I think [00:11:00] is, I think it de bodes well for you in the reader's eyes that you're just not making the weight and you're giving something right away.

Chenell Basilio: Yeah,

I totally like that big fan.

Dylan Redekop: big

fan. Yeah, that's a good one. If we want to stay on the topic of this is maybe a bit of a reach for segue, but here, and Drew does something kind of like Tom in some ways Tom's got the personal, Hey, it's me, I'm Tom. Picture in his welcome email, it doesn't necessarily prompt a reply, but, uh, you've called it or did he call it the magnetic closer?

Was that you or

Chenell Basilio: think I called it that

one.

Dylan Redekop: You called it that. So the cool thing with this is Kieran basically writes a line of text some words on a piece of paper that's hyper relevant to the newsletter he just sent you. And he puts a picture of him holding up and smiling at the end of his newsletter editions. And so a few things I love about this is one.

Very easy for you to do this as a creator to, to write some words on a piece of paper and take a picture. Of course, you're directly copying Kieran Drew, who I think copied this from somebody [00:12:00] else. You can do your own version of it, but my point is it's low friction for you to do as a creator.

And it shows like that A real person thought through and wrote this email, or at least took the time to I guess put together enough effort into it. That they were holding a picture of the relevant message from the email. So it just, to me, in the day and age that we're in of like AI slop, everywhere, whenever you're wondering if, you know, uh, a newsletter was written by AI or not, at least somebody holding a picture of themselves, then again, they could AI create that with ai.

I don't know. I, my whole point is like, it just feels more human, it adds more of a personality and like a real person behind the message.

Chenell Basilio: Yeah, and he said that he he would record or he would take a couple of these pictures. It's just so he could batch process them. So he had some bonus ones. If for some reason his hair looked crazy or he didn't wanna shower that day or whatever, he could just put in one of those, like evergreen ones he called them. But most of them were completely directly tied to the message. [00:13:00] And so like, he might be talking about. How he figured out that he was, he loved writing and how writing was like a through line for his life, his whole life, and so on. The message of the one that I'm looking at, it says, are you born to write? And he is like smiling, holding this picture. And it's oh Yeah. That's like a cool little message there. It's like tying back to the story he just told you.

Dylan Redekop: I really like it. Especially,

he doesn't necessarily come by this naturally. 'cause Kieran was a dentist. Like that was what he went to school for. That's, that was his profession. And he made a huge pivot and became like a content creator. It's really interesting how going from one very like, I don't know.

Traditional profession turned into something like this and how he's really like running with it. So I, I admire, I admire what he's doing and doing this, and again, it's not going to, this isn't going to like get you, you know, a thousand subscribers every day or anything like that. But I think this is just one of those things, like we talked about retaining people.

This is just one of those little things [00:14:00] you can do to, I think, increase some retention in your newsletters where people see, hey, there's a real person who's sharing some interesting. Information that's helpful and sharing some personality too. So it adds, again, a little bit more of a human touch in your, in your emails and just, I think it's more likely to keep people than the opposite.

Chenell Basilio: Totally,

and it's, you think about it like he puts it at the very end. So if you're like another email, let me go unsubscribe, and you're scrolling and then you see a Karen smiling face like holding up

this thing, it might make you think twice about unsubscribing. So I do like this. It's definitely not like a, Hey, add these to your email and you're

gonna reduce your unsubscribes by 20%. But I think there is probably some number like that. It's just not something

super quantitative that we can measure.

Dylan Redekop: Yep. Yeah, you could test it out if you start doing this and you notice your unsubscribe rate, starts going down over a period of time. But there's so many different factors at play with that, that it can be hard, pretty hard to quantify. So I get it. But I think it's net positive is, I guess my point doing this is not gonna be a [00:15:00] net negative.

Chenell Basilio: So talking about adding, personalization to emails and that kind of thing why don't we talk about the whole recommendation subscriber dilemma. Right now, just for context, like recommendation subscribers are if I, partner with Dylan and somebody subscribes to my newsletter, a little popup box might show up afterwards.

It says, Hey, you might also like growth currency with Dylan Redekop. You should go subscribe. Now. The problem with those is it's a very quick click. It's almost like. You gained a follower, not a real subscriber yet. And so you wanna do some extra legwork to make sure they know who you are, what you're actually gonna share with them, and what kind of content they're gonna be getting from you.

And so there was some really interesting ways you can do this and give people more context of who you are and what you talk about. Yeah.

Dylan Redekop: how I do that?

Chenell Basilio: Yeah. Go for it.

Dylan Redekop: Okay. Yeah I've been doing this for a while because I, .What I did notice was I made the mistake at first of just sending everybody who subscribed to my newsletter the exact same welcome email and. What [00:16:00] I didn't realize until I started receiving recommendation emails, so emails that I had subscribed to via somebody else's recommendation, all of a sudden showed up in my inbox.

I'm like, wait, what? I don't remember subscribing to this. It is just like a regular welcome email, assuming that I. Meant to subscribe or I knew who they were, or had followed them on social media, which in this case was none of those things. So I'm like, Ooh, this wasn't a good experience for me yet.

I'm doing the same thing to my subscribers. So I thought it made a lot more sense to treat them very differently from, than somebody who's maybe come to my landing page via LinkedIn, who's consumed my content on LinkedIn, and then is subscribing that way. So I I set the context, I guess I create a bit of a context block and say, Hey. You subscribe to my newsletter. If you don't remember so and so recommended you and in Kit, and I think you can probably do this in Beehive, um, in Kit I use Liquid Code and it pulls in the the name of the referrer who recommended them. So if it was Chenell would say, Hey, my friend Chenell from Growth in Reverse recommended you to my newsletter.

Thanks for coming [00:17:00] around. Um, or thanks for subscribing. Here's what my newsletter's about. If that sounds interesting to you, stick around and I'll be, I'll add you to my list. If not, here's a big unsubscribe button because if you didn't mean to be here or you if you're not interested in this content I don't wanna waste your time, feel free to unsubscribe.

And so in doing that, I've seen my unsubscribe rates drop quite a bit and uh, I should say I've seen my. Emails, send unsubscribe rates, drop right drop quite a bit because the people who maybe passively or accidentally unsubscribed, they will just get off the list right away. And I don't risk sending I guess newsletters to people who didn't want them and then getting flagged for spam or getting complaints and that sort of thing.

So I think this is just a. A really powerful way to kind of almost do like a list cleaning upfront. And it's just like a nice thing to do for people who are coming to you from a, out of context spot. Like a recommendations.

Chenell Basilio: Yeah, I like this a lot. Another good example of this I've seen was from Katelyn Bourgoin, who we talked about [00:18:00] previously, but, she actually puts a picture of the recommendations widget in the email. So it's like really jogging your memory on this one. And I started doing this as well 'cause I was like, that's super smart. I wanna show people like, hey, remember this box you might've seen

for three seconds? Here's where you signed up. And it just reminds people like, oh, I did sign up for this. I , I could put my guard down a little bit. Maybe I'll read about who this person is. So I think those two combined is like a really powerful way to turn someone who might be like a very, loose follower into a more robust subscriber keep them on your list.

Dylan Redekop: Yep. Get 'em from cold to warm, right?

Chenell Basilio: Cold to warm. I like

it.

Dylan Redekop: Yeah. Yeah. So I think, I think that more people should probably consider this, and I don't even think that you need to, um, you don't have to reinvent the wheel at all. It can be a pretty basic message, but maybe even consider other places that you are getting subscribers from.

Like, I've dabbled with the idea of like having a, subscriber, uh, LinkedIn, for example, a LinkedIn subscriber specific [00:19:00] either landing page or welcome sequence for people who are coming from there versus other places. So I think thinking through, uh, where you're capturing new subscribers and then sending that context in the first email you send them, I think can probably help you a lot more down the road with engagement and retention than just sending everybody kind of that blank welcome email.

Chenell Basilio: Yeah. All right. One more I wanna share and then I think we can call this an episode. Jason Resnick from Nurture Kit. Uh, he's super smart with email marketing and like all the little nitty gritty things you can do, but one of the tips he shared was what we called the four hour email. So essentially if someone subscribed to your lead magnet they were looking to get a specific resource. They're very excited about that thing. But then. Maybe they don't open and they don't click that email. And so it's like, well, why'd you sign up if you didn't really want this thing? So what he does is he sets up a trigger. So if someone doesn't open that email that contains the lead magnet in it if they don't click on that, he will actually [00:20:00] send them another email four hours later and say like, Hey, did you get the thing?

Sometimes like, things get lost. I wanted to make sure you saw this. Oh, and by the way. I'm curious what you signed up for. Is there something I can help with right out the gate? And so you're doing it, you're like kind of doing a resend of an email like, Hey, don't forget about this thing, but you're also able to get more people replying because it feels more personal.

Dylan Redekop: I agree. I think the powerful thing here is uh, it is twofold. So it's like just making sure, I think we've, we're all guilty of like signing up for a lead magnet and then forgetting to like actually click through on that email to download it. So making sure people actually get the thing that they came for that's going to hopefully help them and put a positive light in their mind about you and the content you're sending.

So the next time you, they see you or they reach out to you, um, they're gonna have that positive experience. But also, yeah, like. Getting replies is really important. So if you can really nail down that messaging in that resend not everybody's gonna get the resend 'cause some people will just subscribe the [00:21:00] first time around, but I think that can be really powerful.

Um, so I've found that, just, I'm just looking up a, a recent one because I've in implemented the four hour email into a few of my recent lead magnets for a recent landing page that I set up, the original email had an 81% open rate, which I'm pretty pleased with. Um, but for the remaining 19% I sent the four hour email and 55% opened that. So think about the amount of people that got the first email, the remaining 19%, another half of them.

Opened the second email, and then we had about a 10% click rate on that one. So again, it's not like, not everybody is going to open every email and click on everything, but sending that reminder email just got a few extra people to open and a few extra clicks. So, for the amount of time that it takes to set this up, I think it's definitely worth trying to do.

Chenell Basilio: Absolutely. That's, That's great. I mean, Again, like the goal with retention and all these optimizations is you spend a ton of effort trying to get these [00:22:00] subscribers. So instead of just letting that extra 19% go, you're like, oh no, I'm gonna take 8.5% and or whatever, nine and a half percent. I can't do math and bring them back. And that's a huge number. Like this stuff, it might seem small and like. Stuff to think about in the future, but it's like if you could just implement that and immediately reengage

9% of those people, that's a big number.

Dylan Redekop: And if you're worried about, people getting annoyed and unsubscribing. So far I have had zero people, according to Kit, here, unsubscribe after getting that four hour email. Again, it only went out to about 30 people, but still there's, zero people were like so annoyed by this at the unsubscribe.

So I think there's definitely value there.

Chenell Basilio: I think if anything, somebody would be like excited that they're like, oh yeah, I signed up for this

thing. That email got lost in my inbox. Thanks for reminding me. So

I wouldn't even be worried about the unsubscribes with that one.

Dylan Redekop: yeah. I know I did. I did post about this on LinkedIn and that was a few comments that I had oh, you're gonna annoy me, instant unsubscribe, and I was like, oh, okay. We're trying to be

Chenell Basilio: don't want you on my

list anyway

then.

Dylan Redekop: it. Yeah, exactly. [00:23:00] Yeah.

Chenell Basilio: No, this is awesome. I think this is one of the reasons, like in I have this thing called the Growth Fault. And in the Growth Fault there's a whole section dedicated to retention, and it's just for this exact reason. It's like you spend all of your time thinking about growth, but why aren't we thinking about keeping people happy, engaging those folks more? And so I just, I always love ideas for. Retaining customers better. So if you have some, comment on Spotify, comment on YouTube,

let me know. I'm excited to hear what you have to say too.

And maybe we'll include them in a future episode.

Dylan Redekop: Yeah, share successful either engagement, re-engagement, or retention strategies that you've had. 'cause we want, we wanna share those. Like we, these are things that we've come across, but, there's a large amount of people who we have not come across who are doing great things. So please share them with us.

Or you can send, I think we have a form set up for the podcast, right?

Chenell Basilio: Yeah, Growth In Reverse.com/question. But this isn't really a question. It's kinda like feedback. You could just email me.

Chenell Growth In Reverse.com. That works too. Um.[00:24:00]

Dylan Redekop: it.

Chenell Basilio: we'll get the thing either way. cool. I like this.

Dylan Redekop: Do you wanna go over your others or is that, should we leave it at that for now?

Chenell Basilio: I think that's good. We can always do a part

two or part three or whatever we need to do.

Dylan Redekop: All right, let's do it.

Chenell Basilio: All right.

Go retain some subscribers,

people.

Dylan Redekop: that's right.

Chenell Basilio: All right. We'll see you next time.

Dylan Redekop: See ya.

The Newsletter Retention Playbook Every Creator Should Know
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