Inside a 1M+ Subscriber Newsletter (My Exact Strategy) | 126

All Healthy has over a million subscribers. What's worked the best for driving growth?

In terms of what's worked really well for us, I always recommend—

Sean Devlin spent years at Optimism helping build a portfolio of email-first brands to millions of readers before founding his own.

A lot of our initial growth came from cross-pollination from other newsletters, and obviously you could do this in swaps with other newsletters too.

He built Nice News to over 800,000 subscribers before it was acquired by Encyclopedia Britannica. In his latest newsletter, All Healthy, 1.3 million subscribers and an incredible 52% open rate.

It's important to determine what it is that your goals are for the newsletter to start. And if we want to group it into 3 categories, we can group it into engagement, monetization, and retention.

If you have an email list and you want people to actually look forward to opening it, you're going to want to stick around for this one. What works best for monetization?

For monetization, for us, we're—

Sean, welcome to the show.

Thanks for having me. Excited to be here.

So I want to dive right in. All right. What's one format change that anybody could make that would make their subscribers more addicted to opening their emails?

All right. So I would start with analyzing your existing format for your newsletter. What does your newsletter look like right now? Why are people engaging with your newsletter? What's resulting in forming habits in your readers and keeping them coming back? And then building on that. So for All Healthy, we have a couple sections that are specifically included to form habits in our readers. One of them is actually called Healthy Habits, so it has habit in the name. The other one's called Final Thought. And these are sections that are further down in the newsletter with the goal of getting people to obviously form a habit of actually reading the entire newsletter too. But you can include something further up too. And then for Healthy Habit, um, these are two sections that don't even have CTAs. So the whole goal is basically to get people to build a habit of actually just reading them and getting value out of them. Healthy Habit is just a tangible recommendation of something you can do that day to live a healthier life. Um, what would it, what would an example of that be? Yeah, so an example would be, um, like Make Tomorrow Easy. So you're getting your clothes, your workout clothes, or choosing your outfit in advance, or getting your lunch ready beforehand or something like that. And then right after that, we have Final Thought where we have quote alongside an image. And our goal for that is to kind of choose something that's relatively unexpected. So we'll choose something like, um, from a podcast or from a book and really try to provoke thought in our readers. And ultimately that section is trying to kind of like evoke some sort of emotion. Maybe it's like awe or inspiration. And our goal with that is ultimately to kind of get them to feel something. And I like to say that you might not remember everything that you're reading in a newsletter, but you're going to remember how you felt when you read it. And that feeling is what's going to result in you coming coming back the next day, the next week. So that's kind of what's resulting in that return behavior. So we really lean into that with those sections. And I mean, for your newsletter, it could be something wildly different. You could do a fact or something that happened that day in history and intention and insight or recommendation. I think the goal is for it to feel like it kind of like fits with the format of your newsletter and doesn't feel like a random add-on and it's providing value and is integrated in a way that makes sense.

Yeah, I like that. I'm thinking about James Clear's newsletter where, you know, his 3-2-1, he's ending with that one question for you. And so he's probably, I haven't talked to him about this, but he's probably wanting someone to walk away with this feeling of like, oh, I'm smarter or more introspective or it's something like that. You know, uh, like thoughtful is the feeling coming out of it. Whereas another example would be Anne Helen Petersen has a section in her newsletter called and it's just a link that just says, just trust me. And that's always, you know, something funny or insightful or something like that, um, where you're like, oh, just trust me. Like, you don't even have any context, just click on it. And, uh, Marissa Lavelle, who runs From Boise, which is a local newsletter that she and I, uh, co-founded, she borrowed that just trust me format. And it's always something funny or all that. And so going back to a feeling, right? You're going to read From Boise either about the news or history or the events. And the last link is the just trust me. And it's the highest click link in every issue. And it delivers every single, like every single time you're like, oh, Marissa, I'm glad that I trusted you and clicked that link because it brought me joy. And so then it reinforces this idea that From Boise is about joy and happiness and lighthearted. Um, so I love that, right? You're, you have a set format that is designed to create a feeling.

Exactly. Yeah. No, I love that approach. And we. We've tried similar sections of that where the goal is obviously to get clicks or engagement, but also to provide value in a unique way.

Yeah.

Yeah.

What do creators get wrong about email formats?

I would say what I think personally, what I get wrong is I lean into certain metrics like open rate and click-through rate and think about it maybe in more of a short-term viewpoint. So for open rate, that could look like. A/B testing 5 subject lines and one maybe being a little bit more offbeat or framing it as a question or incorporating an emoji. And then let's say that one wins and that's sent to the entire audience, but it happens consistently over the course of a week or something like that. I mean, it can be a little annoying if your subject lines are framed as a question every single day. So I think it's kind of finding that balance in terms of tone and approach and making sure you're representing your newsletter the way that you want to. Or for click-through rate, it could be you include something that maybe feels a little bit clickbaity, but it ends up in your audience clicking it. And like on a performance basis, I mean, you're looking at the click-through, you're like, oh wow, it performed really well today. Like the newsletter performed really well, but did it leave a good taste in your, your subscriber's mouth? I think it's important to be thinking about the long-term relationship with your subscriber, not just looking at those metrics more near term.

Yeah, it's interesting thinking about clickbait, which we describe as a negative term, right? Like, oh, you don't want it. That's a clickbait headline. But it's only a negative thing if you don't deliver.

Yeah.

Like if you bait me into clicking on something.

Exactly.

And then it, it pays off. And as a, as a reader, I'm like, oh, had you framed that in a boring way or a generic way, I wouldn't have clicked it, but I'm so glad that I did. So thank you for, it's not like we're fishing or something and now you've got me on the hook. It's like, no, thank you for Um, getting me to engage with that, like my life is better, my insights are better, whatever, because of that.

Yeah.

So were there things that you've maybe pushed the envelope on, but then made sure that you could follow up and, and actually deliver the value with it?

For sure. Yeah. I mean, we'll lean into that in terms of like phrasing for certain wording where it's like, this one's our favorite, or maybe you missed this to get someone to click. But ultimately to your point, you need to make sure you're providing value to them and they're happy with where it is that they land and they're not like, what is this? It's like a sponsor or something like that.

So if I understand correctly, All Healthy is over a million subscribers. Yeah. Right. Mm-hmm. And you have pretty crazy open rate numbers. Like I always see people grow these big lists, but then the open rate declines and I'm like, you don't actually have that much engagement.

Yeah.

Talk to me about one, what is the open rate? And then two, how do you, how do you still manage to have that high of an open rate on that many subscribers?

Yeah. So for us, open rate's really important. I mean, our newsletter is a 5-minute digest. Our core goal is to get people to open and read. We're not focused as much on just getting someone to click. So developing that relationship with them is really important. Our open rate is north of 50%, around, hovers around 52%. And I think we're able to do that just ultimately by providing value to, to our readers every day. And they come to expect a specific format with the content that we're sending. And we still have kind of like some element of surprise sometimes with changing things up in terms of the sections that we include. So it's this balance of providing value every single day. Um, getting trust from our readers and then that results in them coming back.

Yeah. So a daily email, is it 5 days a week or 7 days a week?

It's 7 days a week.

Okay.

So it's truly daily. It's like a roundup though.

Okay.

So it's, yeah.

And I think people's worry is that if I send emails that often, I'm going to have higher unsubscribes. I'm going to wear out my readers. I'm going to not, I'm not going to get high engagement and I'm going to cap my growth because the unsubscribes will always be a percentage and the growth is a fixed. Fixed number. How do you think about that? Why a daily email for us?

Yeah, I mean, it's definitely something that we've considered in terms of the frequency, and we, we explicitly call that out in the footer, like, do you want less emails? Click here. So our Sunday email is more of a weekly roundup. People could just get it once a week if they wanted to, but we try to really cast a wide net with the topics that we're covering with All Healthy. So we'll cover everything from, I mean, nutrition to fitness to relationships to mental health. And because of that, it's wide-ranging and there's value in people find the content interesting each day. But at the same time, I mean, you don't have to be opening and reading it every day.

And it's not like, oh, we, yeah, we missed episode 4 of the season and now the rest of the season doesn't make any sense.

Exactly. Yeah. So for us, I mean, obviously it's great to be able to monetize our audience every day too. So there's value in that. And I think it really depends on the content that you're sending. If it is relatively niche, it probably doesn't make sense to be sending it every day. And if you're looking at your unsubscribe rate and it's skyrocketing when you send a particular type of email or frequency. And maybe reevaluate from there.

Yeah, you brought up monetization. So how does All Healthy monetize? And then also, like, there's other newsletters in the network, right? You've scaled Nice News, you've scaled a bunch of other, uh, newsletters. Like, what works best for monetization for this style of newsletter?

Yeah, so for monetization for us, we're in email sponsorships. So in terms of what's worked really well for us, I always recommend that people think about how your newsletter sponsorships are incorporated in a way that feels seamless and provides value to the reader. Reader to in terms of obviously the sponsors that you're including. You want to make sure you're partnering with brands that are aligned and actually provide value to your readers. But also, of course, you're like labeling that this is a sponsored section, but sometimes when it stands out so much to the point where it's just like drastically different in design and it's something that like feels very like different from the rest of the content that's included, people can form the habit of just skipping over it. So we find a way for it to feel really cohesive and integrated well. And then obviously like there's value there. And what we do in terms of tone of voice is we make sure it's written by our editorial team in a way that kind of is cohesive and seamlessly is integrated. And we also try to take an editorial approach with the content. So as an example, for a sponsor that we have called Native Path, which is a collagen supplement, we'll talk about, um, kind of how collagen impacts bone density as an example. And then we'll dig into that a little bit and then link out to learn more. Or a hydrogen water sponsor, we might be talking about what does the science actually say about hydrogen water? Like, why is everyone talking about this? And then get them to click to learn more. So that approach just feels more, it kind of draws the reader in, gets them interested in the content, and then gets them to click. And we've noticed obviously engagements increase, but also conversions, like total conversions can increase because you're just getting the audience interested in something and then getting them to engage from there. So that approach has worked really well for us too.

Yeah, I'm thinking about that. Most sponsorships, like let's say that, uh, we had a newsletter about the creator economy or something and Kit was sponsoring. Most would come in and be like, sponsored by Kit. Here's why Kit is so great. Go sign up, go become a Kit customer. And what I hear you talking about is, you know, instead it'd be like, why email is important as part of your Creator tech stack. And then it'd be thoughts on that. Maybe some quotes from, uh, you know, John Youshaei or someone like someone that's trusted within that community. And then it's like, oh, go learn more. And this is brought to you by Kit. Is that right? Of taking this editorial approach instead of the sales approach?

Yeah. Like kind of getting that initial interest in the topic and then providing a solution to something rather than just like starting with the solution. Like, this is why you need this.

And you're like, need what? I didn't know that I cared. Yeah. So it's, I guess I could see that, that content, maybe the first thing is sparking curiosity, right? Of having the headline of the section or, you know, you have to open this loop that then you're able to start to close and you don't even have to fully close it. Like something that I've seen work well with newsletter sponsorships is when they're really just trying to get the click-through and then ultimately retarget those people later. And so you don't even really care about making the sale on the page that they click to. It's like, We got people who are now interested in our target market. You know, they're within our target market, interested in our topic. And then as a brand, we can follow up later with retargeting or with, you know, we're probably not running one ad in All Healthy, right? We're running a series over a series of months. And so there's a lot of opportunity to make the sale long-term.

Exactly. Yeah. And that's our ideal partners. They're not just looking at that one placement and conversions from that one placement. Obviously they're analyzing it, but they're looking kind of more holistically. Yeah. And then in terms of, of placements that we have, I always recommend having more than one type of sponsorship inclusion. So we have a primary, we have a secondary, obviously more ad inventory equals more dollars, but it allows you to charge different price points, maybe test something on more of a performance basis. And we have a section that's called Quick Picks too, which allows us to, it's like more short form. We can test a performance sponsor in that section, actually get kind of a higher volume of engagement too.

So I've seen a few people do those where they might say like, here's my Um, 5 favorite things, like the, the, and 3 of them, or there's 5 in a list, but 2 have an asterisk next to them that ends, has a note of like, you know, sponsored partner or something like that. Is that kind of the style?

Yeah. We just do one that's sponsored and it's not every day, so it doesn't feel too, too heavy, but yeah, that's the approach.

Okay. And then from a monetization perspective, what can you say about what sponsorships in the newsletter cost, how you structure them? Like if someone is saying, hey, I've gotten to I have, let's say, 50,000 to 100,000 subscribers in my newsletter and I want to start to take on brand deals and, and, uh, sponsorships. Like what, what advice or direction would you give them? And then we can get into more specifics of, you know, monetization strategies.

Yeah. I mean, obviously it's always great to be able to just have flat rates that you're charging your sponsors and you can just do it based on a CPM. Ultimately they're looking at performance on their end. And I always recommend starting at a more reasonable rate just based on the inventory that you have available and then building up from there. I mean, if you have, if there's scarcity, you can start charging more and more. And then depending on the partner, it could make sense even if they're really kind of opposed to or not interested in something that's flat rate, you could test out a CPC and certain sponsors click exceptionally well. That example I gave from Native Path, they're on a CPC for us. It actually performs better than if we were to do flat rate. So it depends on the approach and the sponsorship you want to take on, but being flexible early on, I think is really important. And then building from there based on the inventory you have.

So a lot of creators might get a couple of brands that come in and say, oh, your audience is the perfect fit for who we're trying to reach. So we're willing to pay this high amount. Let's say, I don't know, $2,500 or $5,000 for a flat rate sponsorship. And I won't do the math on CPM, but let's just assume that that's a good, a good CPM. And so then the creator gets attached to that number and they're able to sell 2 or 3 more at that, but it's. Sporadic, maybe have their own product that they're promoting in there sometimes. And I think what I hear you saying is it's best to not be attached to the high price and instead maybe be at a lower price where the brand is saying, wow, we got a crazy return on investment, can we book out a bunch more? And then you're getting to where the demand is really, really high. You've got 4 or 5 sponsors that are all performing really well and their ad teams are like, how can I buy more? And you're like, well, we're actually— Q2 is already booked out. Yeah. Then it is to say like to command the highest price and have these openings where you're like then starting to have to really push to close them. Is that right?

Exactly. Yeah. Because if you have limited inventory, it allows you obviously to increase the rates. And for us, I mean, we're a daily newsletter, so someone is going to probably ask, do you have remnant inventory available? I'm like, sorry, we don't have any inventory available. We're booked out 100%. That allows us to charge higher rates. And then also it has to perform well enough for them, for them to, to come back and you want it to be a recurring relationship.

Well, and that's the thing that I think creators get wrong is they, they, most creators that I talk to, they want a CPM, uh, based relationship and most brands want some, uh, like pay for performance model. And so they're naturally at odds with each other, but what the creator doesn't realize is that. The brand is evaluating it based on performance regardless. And so it's not that one is better, like better than the, than the other. Like ultimately they converge to the same thing and it just shows up in how many repeat buys did this brand make? And so the, like, I, yeah, I guess what I think is creators should be way more open to a cost per lead or cost per click or cost per conversion model because that ultimately aligns with, with the brand. Um, and just test both.

Yeah, I agree. And I think that I understand the hesitancy in terms of like a CPA or CPL model. And that's something we, we try to avoid in particular for brands when we're uncertain what the performance is going to be if we haven't tested something before. But once you have those baselines that you can work off of, then you understand like what makes sense for the brand and what makes sense for you, what the likely engagement is going to be, and then you can price it accordingly.

What about getting, once we have that baseline filled, you know, it's like, hey, we've got our slots. It might be a blend of a few different deals with a few different advertisers. What's worked the best for being able to drive up those rates over time? Probably ultimately drive up the performance over time for the advertisers.

Yeah.

You know, but you know, as a creator, I'm like, look, I've got 100,000 subscribers. I'm making a good amount. I'm not going to increase my sends per week, you know, either because I physically can't because I'm already at 7 or, you know, I'm at my limit as what I can produce, but I want to earn more per impression. What are the things that make the biggest difference?

I mean, for us, I mean, you mentioned like booking out for the quarter. We typically do it. I would love to book out further in advance, like for, for even annually, but it can work well booking out more short term. So like our April, for instance, is full and now we're trying to book people out for all of Q2. And then it allows us to, to reference kind of the inventory that we have available and then try to kind of fill the slots. And make it feel like we don't have— I mean, hopefully you are in that position where you just don't have as much inventory, so you're then filling at a higher rate. I think having like those consistent partners that you're booking out on a quarterly basis or monthly basis is going to be where you're— allow you to have the most success because you have kind of that consistent, like every other week this brand is performing and we're expecting that we're including them based on our rates that we have right now.

Yeah. And so that makes sense to me, but I'm wondering about What things I should do in the newsletter itself or in deeper partnerships with a brand? Like what, you know, for like, hey, we're at a $20 CPM is what it ultimately, however it's, it's billed, it ultimately is equating to this $20 CPM. And I want it, I really want it to be a $22 CPM.

Got it.

Like, what do I—

How do you drive that up?

Yeah.

Yeah. Yeah. I mean, ultimately you have to find ways to increase performance. So if you're bringing in new audience, that can be really beneficial for increasing engagement. Also testing out different things. I mentioned taking the editorial approach with the copy, maybe leaning into that, trying different approaches for what it is you're covering, the angle that you're taking, the placement type. Uh, maybe you throw in something that is shorter form to drive more engagement in addition to the main sponsorship that you have. So testing things out and ultimately they have to see that performance on their end for them to be willing to pay more.

Right.

So hopefully you're growing your newsletter and that justifies the increase in rates too.

Yeah, I like that. I've also seen creators go through and say, hey, you're sending these clicks that I'm giving you through to a generic landing page. Can I, you know, can you make a custom landing page for me that has a quote from me talking about the product?

Love that.

You know, and has some of this handoff and really, I mean, it just comes down to, I guess, probably two things. One is standard conversion rate optimization that would like work whether you're running Meta ads or anything else. It's like, Does your headline match the thing that they clicked on originally? You know, you're bringing people through. But then the other thing is taking responsibility for the performance, right? I think the more the creator says, it's not just my responsibility to hand over 200 words worth of space, you know, and, and 300 pixels or whatever. It's like, no, I'm, I'm taking as much responsibility as I can for the, sales that are ultimately driven. And then as a result, I want to get paid more for it. Mm-hmm.

Yeah. I think thinking holistically like that is important because it has to be successful for them. And if you're driving them to a landing page that isn't converting, then you're not going to be able to continue to work with them. So it's great when you find partners that are open to that feedback and have the flexibility to be able to implement ideas and suggestions that you have.

I like it. Okay. So I want to go to newsletter design and structure, right? Because people can get tired of a certain format or, or they can fall in love with a format and keep coming back to it. But as you've worked on different newsletters, I'm curious, what's like, do you have rules of thumb or things you keep coming back to on like how the newsletter is designed and laid out and that sort of thing? Or ones that you see and you're like, ooh, you know, gut feeling is like, don't do that.

Yeah. I will say it depends on the goal of the newsletter. Like there are ones that I've launched in a previous life that are like legitimately like just a trivia question. So you're just trying to drive traffic to web or just like trying to drive traffic to an article in that place. And in that, um, case, you want it to be obviously super short form and you don't want it to be like, you don't want to provide all the content, uh, to them in the newsletter because ultimately then they're not going to engage. We take a modular approach with our current template for All Healthy and we took a lot of the learnings that we had from Nice News and applied it to All Healthy. And what's worked really well for us in terms of like the beginning of the newsletter, and when we have intro text, we're establishing that relationship with the reader and then kind of drawing them in further and then having a few featured stories. Um, and then from there kind of having some sections that the, like I mentioned, healthy habit and final thought that the reader comes to expect, but also throwing in some new sections here and there, um, which allow us to kind of have this, this balance of predictability and surprise.

I like that. Are there any newsletters that you don't work on that you follow that you're like, ooh, they, they particularly do things well, or you're like, all right, there's real craft behind it, or I want to build a newsletter, you know, on that scale, or get ideas from?

Yeah. Um, I mean, in the health and wellness space, I'm like always thinking about that. I love, even if it is just primarily text, I think finding ways to have the content be seamlessly incorporated. It works really well. So I love like Pump Club and Fit Insider and some of these that are a little bit more kind of industry specific. But yeah, I mean, it really depends on what you're trying to get your audience to do. So if the format is allowing your reader to stay in the inbox and continue to read, then something's working well if that's what you're trying to do. And then if the format is resulting in them clicking to go to web, if that's what you're trying to do, then it's working well. So it kind of depends on your goals from the beginning too.

Anything that you've seen that's really novel where you're like, okay, I've been in the newsletter game for a long time and here's someone doing something that you're like, that's different. It may not be right for my goals, but like, that's an interesting use of email.

Yeah. I would say in terms of finding that balance between the two, I really love, uh, the Washington Post has a newsletter called like The Seven and they incorporate CTAs in a way where it's like they're providing a good amount of content in the inbox still. So it's kind of like building that habit with the reader.

It's not all just about clicks.

Exactly. But then they do the CTAs in a way for their featured stories that feels like it's really compelling. Like you want to click to read more. So it's this balance of like, I'm sure they're monetizing on web and then, or upconverting people from there. And then also they're getting people to engage in the inbox. So I think it's difficult to find that balance between the two. I think they do it really well.

Yeah, I like that. All right, let's talk growth for a minute because you, you don't get to a million plus subscribers without having a few things figured out on growth. Obviously you've gone, um, broad appeal with your newsletters. Which makes it easier to get to tens of people, right? Like if someone's building a business newsletter to over 100,000 people, that's very hard to do. And that might be equal difficulty to like a food newsletter at 200,000 or 300,000, right? Where the broader the appeal, um, the cheaper you can acquire traffic, larger target market and all of that. But what's worked the best for driving growth? And maybe we could talk at different scales, like the 0 to 100,000 subscribers, and then we could dive into the, you know, 100 to 500 and then beyond a million.

Yeah. So I will say we were in a unique position with All Healthy in that we were a part of a wider Optimism portfolio, our parent company. At the time, there were a good number of brands in the portfolio. So a lot of our initial growth came from cross-pollination from other newsletters and tactics that worked really well for us there. And obviously you could do this in swaps with other newsletters too, but, or paid placements too. Uh, we would incorporate, I mean, explicit sections to get health and wellness in your inbox and then, um, guide to landing pages to upconvert from there. But then once we had kind of those core subscribers that were extremely engaged, we then kind of scaled beyond that and then included pieces of content that were our highest engaging pieces of content. And then in order to click to read that piece of content or to get access to that piece of content, kind of like a lead gen flow, you have to input your email to, to get access, or from the click initially, you're being subscribed from there. So that allowed us to really scale early on. Um, and then now a lot of our tactics are via paid, in particular Meta is is where we're really scaling spend and we're using kind of some of those same flows in terms of lead gen. So we have guides that we're doing for All Healthy around a particular topic, like how to undo sitting all day or how to, um, how to like things you need to throw away in your kitchen, like something that feels really compelling and aligned with like topically what it is that we're covering.

And it sparks that curiosity where I'm like, well, hold on, what should I throw away? Yeah. You're like, wait, now I want to know where's the guide.

Exactly. Exactly. Um, so that approach has worked really well for us because obviously like we get a lower CPA, but also once someone subscribes, they then, they have to click in their inbox to be able to access what it is that we're sending to them. So you get that initial engagement. If someone's not clicking, we're filtering them out. So we're able to still kind of like keep on board the people who are actually engaged. So we've leaned into that a lot. And then through our sister publication, Superage, we're doing a good number of quizzes too.

Okay.

We've done a quiz around like how long you're likely to live, and then we're asking them a ton of questions. So we're getting a lot of data points up front, relatively low CPA, and then sending them the results via email. They're engaged in the inbox immediately. So I think thinking about flows that aren't just like sign up for my newsletter, click here, they're signing up, which can work really well too. Um, it's allowed us to get a lower CPA and sometimes even higher engagement.

Yeah. Okay. So let's dive in on Meta ads in particular. Like what, what do you think of as for each of your brands, like a good CPA that, you know, for acquiring a subscriber, what do you target there? And then what are the things that have helped the most to drive that down?

Yeah. I mean, some of the flows that I mentioned in terms of lead gen have helped us drive that down. Like for Nice News, we were hovering around like a dollar CPA for the typical flow, which was like driving traffic to a landing page to get good news. And then you're. Inputting your email explicitly to get that in your inbox. Currently we're sitting like less than 50 cents for CPA. And sometimes, I mean, depending on the campaign, that can even be like 30, 40 cents. So that's relatively low. I know people are willing to spend a lot more for subscribers, but I will say that obviously some of those subscribers are just trying to get their quiz results or just trying to get this particular guide and then they aren't as engaged. So you have to filter people out. And it's worked really well for us also too, because we have the ability to share kind of cross network. So we can even lower that CPA further if sharing it with another newsletter, um, or having an integration like SparkLoop or a partnership with another newsletter can allow you to lower that CPA too.

Yeah. Yeah, that makes sense. I've seen people really build those optimized flows where it's usually exactly what you said, a quiz or a lead magnet on the front end. It's not the main call to action isn't get healthy tips 7 days a week. It's like very specific pain point solved. And then, you know, it flows into that. And then usually the cross-promotions, uh, whether it's through something like SparkLoop or, you know, that you manually put together where it's like, hey, I'll cross-promote your newsletter. You're paying me if they end up becoming engaged over here, or the offers portion where, you know, maybe there's a brand, like one of your sponsors, you know, whether it's the water brand or someone else, right? That's in that opt-in flow. Um, and helping to recoup some of that. And then more in the creator space that you see is a lot of like a direct upsell into a product. You know, if someone has a $10 to $50 product that is tightly aligned with the lead magnet, you know, I've seen like coaches do something where maybe you're downloading the industry checklist, you know, or the 5 biggest mistakes made in X industry. And then it's like, hey, do you want to pay for you know, pay $100 for an audit where we'll go and audit, see, like give you, you know, a half-hour coaching call of like, are you making these same mistakes? And, um, and I've seen that work well, especially, especially for someone who's doing a low volume of leads. You would never want to offer that, you know, thousands of leads. But if you're a coach and you, you know, you're like, look, if I did 10 of these a week, that'd be amazing, then some funnel like that can work out. And then you have You're either getting to a much lower CPC, CP, CPA, or CPL, cost per lead, because you're making up that money relatively soon in the funnel.

Exactly. That's what we're trying to lean into more now is like lowering that subscriber payback period. Cause it's just, I mean, it's amazing when you can get that back immediately.

Right.

Yeah.

Compared to when you're like, well, let's see if this person opens consistently over, if they're this likely to open consistently over the next 6 months, then we'll make it happen.

Click on a sponsor here. Yeah.

Yeah.

To get a little bit more granular in that regard. Yeah. So I think it's helpful to think about, I mean, depending on what it is that you're offering, finding something that monetizes that, that individual faster or engages with them. Maybe you have a set onboarding flow that's like your top engaging content for that individual. They don't necessarily know that that's what you're sending them, but it gets them then to drive to wherever they see something different than the average subscriber that is gonna result in, um, getting that money back faster.

Yeah. Okay. I'm curious about these. I, I spend a lot of my time in niche newsletters, right? Where someone might have 10 to 100,000 subscribers, but a very high revenue per subscriber because they're talking about marketing or engineering or some, some like very focused topic. And so it's interesting for me to talk to you where you're in the broad appeal and you're like, hey, How do we, you know, nice news, right? As a premise is just like, like, could be anyone.

Yeah.

Could be anyone.

Yeah.

Right. Do you like happiness? Would you like to be happier and see the good things in the world? Yeah. Um, I'm curious if there's anything that you've learned from the broad appeal newsletters that you would recommend for the like narrower niches where you're like, look, they're not two separate worlds. You should, you shouldn't dismiss all of this over here. Here's how you should incorporate it?

Yeah, that's a good question. I mean, in terms of user acquisition, I think it's like much more lenient for us where we've done like joint giveaways with different people. And because our content is so general, there's a high likelihood or high probability that people are going to be interested in living a healthier life or having positive news in their inbox. So that approach can work really well. Um, I think you obviously, like, if you are more niche, you just have to look at where your audience is and try to target them outside of just casting a super wide net. Um, yeah, so I don't know if that's directly applicable necessarily for, for user acquisition, but I mean, for monetization, I mean, we're still thinking through the lens of like, we're trying to provide content that is valuable to our audience. So we're trying to find partners that our audience is genuinely interested in. I think that translates to, I mean, you need to be partnering with brands that are providing value to whatever it is that you're, you're covering and why your audience is reading your newsletter each day.

Yeah. Yeah, that makes sense. And thinking about individual tactics, you mentioned, um, using partnerships a lot to grow the newsletter, which helps, right? That you're like, oh, well, we're within, within our own company, we have, you know, large newsletters already we can cross-promote. Um, cause it's not really this angle of like, well, if they read one newsletter, they won't read anymore. It's like, no, if they're, you know, you might have like someone who reads Nice News could happily read All Healthy, right? And cover different angles on it. So the cross-promotion there makes sense. But something that I've seen a lot of creators do really effectively is the collaborations or the newsletter swaps. And those work well within niches because it doesn't take— if you have 10,000 subscribers and someone else that you're working with, talking to has 15,000 in a related niche, like it doesn't take that much results for it to be worth it for me to write like a great guest post for them.

Yeah.

If I get 200 subscribers, like, okay, that was, you know, like, uh, a couple hundred high-value subscribers that would've cost me, you know, $400 or $500, $1,000 potentially to go acquire in Meta depending on, on the niche. Um, and so I, I see a lot of creators do that, but the thing that I feel like they mess up is they do like 2 one-off partnerships where they're like, oh yeah, I did it with this person and that person. And you're like, did it work? They're like, yeah, it worked great. So what are you going to do?

I don't know.

I think I'm going to try Meta ads or I think I'm going to go do this. And you're like, you just described to me something that you, that you could replicate that worked multiple times. And so go do it.

Find a way to replicate it.

Yeah. Go do it 50 times. Like, um, there's a book I'm reading. I think it's just called The Book of Elon, uh, by Erik Jorgensen, which is about, it's just quotes like Elon's life philosophy and, and all of that, all in his own words. Um, and, uh, one thing that the book talks about is what happens if you scale this up, right? To, to think in first principles or, um, to like pressure test ideas. Like, okay, well, if we, if we did 2, everyone else is like, oh, we could do 10. Like, okay, well, what would have to be true to do 100? You know? And then you're like, oh, okay, we could reasonably, like, is there enough total addressable market to do 100 partnerships with other newsletters? That are interested in our content. Yeah, probably.

Yeah. And how do you find that way to scale it?

Yeah.

Because I think for us, we probably should be leaning into that more in terms of, I mean, you mentioned guest posting. That's a great way rather than the typical swap of like, let me include your newsletter in this placement. You include me in, in this placement, which can obviously work well too, but you can only scale that so much because you're not including like 100 newsletters and individual send.

Right.

Uh, so yeah, finding ways to, and we've done actually something I mean, in this vein where we'll have like a spotlight on an individual in our newsletter, and I'm sure it's worked well for you in like the podcast space where it's like you have a guest on, they then reference that, like share with their community that they were on your podcast. Similar for that spotlight section for us. We feature them. We request in return if they're open to sharing that with their community. I think finding ways to kind of scale it in a unique approach and collaborating with different individuals can work well rather than just kind of the typical swap and I'll place you here. You, you place me there.

Right. Yeah. It made me think of what you're talking about with Remnant Inventory as well of like, you could fill all of your ad slots and a third of them are paid because you're able to sell those deals and all the rest are, are those, um, swaps that you're doing.

Yeah.

Because more growth is going to get you, uh, a bigger audience, which is then going to make you, you know, it's like it fuels the whole flywheel. Like if I'm saying, hey, I have 10,000 subscribers, can we partner? You're going to be like, um, I have a million. That's not quite going to work. You know, so I'm going to be able to partner with people in the, like, call it 5,000 to 25,000 subscriber range. But then as I grow to 25,000 subscribers, I can partner with people in the 15,000 to 50,000 range and up from there. So growth fuels everything. And so, yeah, I think what you're talking about is not only doing the swaps to fill the remnant inventory, but then also say like, hey, let's figure out any way that we can make this really valuable. Might be more that we're doing on social, or it might be like, what else can I do to help grow your newsletter or help promote your brand as a creator? Because that's gonna make people more eager and excited to partner with you.

Yeah. And it could even be centered around just providing value, to your point, where it's like they're providing content to you that's really valuable, you're providing content to them that's really valuable, then I mean, growth is sort of like icing on the cake.

I think, yeah, I guess the way I was talking about it more is about the swaps. Mm-hmm. But you could even just say, you know, all these creators, they write a newsletter every Tuesday and they're like, they might be running out of content and you're like, hey, can I come teach this? I get paid to do this for workshops and for keynotes and all that. Can I just teach my best stuff to your audience for free? Mm-hmm. And a lot of people would be like, yes, please. You know, it's like, well, what value did you deliver to the creator? They don't have to write that week's newsletter and it's going to be really good. You know?

Yeah, exactly.

Yeah. And so especially if you're friends with people, um, that's going to be much more likely to, to work where they're like the combination of like, yes, you're taking this work off my plate. Maybe I'm doing you a favor in some way, but like your content is good. So when I get in front of my audience, yeah, I like that. I'm thinking about flywheels, um, because what I want people to do is really to, to dive in, like, to pick one growth mechanism. Like, if you're amazing at meta ads, then like do that and obsess over how to get your CPA down and, um, you know, bring the— like decrease the cash conversion cycle and all of these things. Um, or if you're like, if you're great at partnerships Then like do that for a long time. And so I'm curious if there's other flywheels that you've implemented inside of All Healthy or Nice News that you're like, oh, I see the more we do this, the better results it gets and the, um, the easier it becomes.

Yeah. I mean, if we want to talk about kind of like content creation as a flywheel too, I mean, we, in general, I think that talking about like, if this is something you're good at, lean into it. We, try to like have that philosophy with our entire team. We're a really lean team. It's me and 2 people on our editorial team. Okay. And we have some freelance writers too, but my goal is to make sure that everyone's focused on what it is that they do best and all the content that we're producing or everything we're doing is being utilized the best way possible. So we have, um, like we use a platform called Feedly as a news aggregator. We're pulling all the content in based on specific sources and what we want to pull from and then selecting from there. Importing it into Airtable, using Airtable as like a CMS, also as a, um, like, um, a collaboration tool, um, like a project management tool too, kind of having everything live in there. And then from there, determining kind of when we're sending content, um, deciding the send date and working backwards from there and having really kind of set workflows. And then also translating that content to different platforms too. So everything's in Airtable. We can then decide if that content's living on social media, we have this like integration with AI that ranks content in Airtable that could potentially work well on social, which platform it could work on, translates that content then for that format. And then, uh, from there we have the ability to kind of like edit and, um, populate it on different platforms and then kind of have everything live together there. And then it allows our team to really focus on what they do best in terms of actually writing and producing content.

I mean, I'm just thinking about the volume of content that you have to produce. And so the fact that that's done 3 of you and some freelancers.

Yeah. And I'm actually not even producing the content I'm doing. I'm doing like sales and partnerships and growth and other things. So yeah, we have, we do have freelance writers too. So that really helps, but it allows, I think because it's such like a refined process, we, I think it's important to like prioritize and focus your time on what it is that you do best and what you have to be doing versus what someone else could be doing. And it's obviously easier said than done, but we have, uh, freelancers in the Philippines that help with like certain campaign management tasks. They help with, um, customer experience, like replying to emails with different templates that we're using or flagging certain things if we need to make sure that we see them. They help us with account management for sales and partnerships in terms of like getting assets and approvals and things like that. So it's like, those are things that like we can create a process around that. It's not something I need to be doing. I think a lot of time can just go, especially as sole, sole individual creators. It's like. You're jumping from task to task to task and it's just not productive. So finding ways to kind of like on a given day, you understand this is, this is what I'm working on. You have the ability to kind of like time block and prioritize your time. And then if there's something that like you're currently doing that you can have AI or a virtual assistant do, create a process for that and figure out a way to do it.

Right. Yeah. So I'm trying to figure out the, the key leverage points in like your editorial process. Was there something that you implemented where you're like, okay, this actually, like, had the most leverage or made a big unlock?

Hmm. I mean, I think using Airtable for everything has been really helpful where everything's living in the same place. Um, we actually incorporated with our CMS the ability for the content to translate from Airtable directly into a template. So that saved a lot of time. Um, yeah, I think that was, that was a big one for us. And then we have the QA process, obviously, in the inbox to make sure everything looks perfect, but we're not having to kind of manually, like, copy and pace things, that's helped.

Okay. And then you mentioned you have AI to help you determine what content was it, what content would do well on social and which platforms.

Yeah. So that is more kind of like translating content to different formats, but we actually are training a Claude bot right now. That's going to do just that where we are currently meeting as a team to analyze performance for content, whether it's for sponsors or for other pieces of content that performed well, didn't perform well. Every other week, but we're pulling that kind of like relatively manually and analyzing it and hypothesizing as to why we feel like something worked well or didn't work well. So leaning into AI to make those kind of, or do analysis for you and make recommendations from there, I think can be really valuable. So that's something that we're, we're going to try to lean into in terms of content performance or sponsorship performance. So it has more data points and obviously we're still from there determining what makes more sense, but it's just a tool that we can use.

Yeah. Are there other places that you've implemented AI in the workflow?

Yeah, we use it for, I will say that our editorial team doesn't use it for all these things, but we've explored using it for different things. So like we can use it for top editing if we need to. We use it for like creating outlines, uh, for content. We use it for like ideation for preheader text or subject lines, things like that based on what's worked well. We use Midjourney for like illustration creation.

Okay.

Yeah. Um, I'm sure there are other things I'm not thinking of that we use it for.

On the illustrations, have you been able to get that all in the set style so it like matches your brand guidelines?

Yeah. So initially we had designers create the illustrations and then from there it kind of allows us to replicate that style and format without needing to have a, a designer do it every time since we're such a, a lean team.

I think that was, has always been the challenge historically with image generation with AI. It's like it'll make something great and you're like, great, now make one like it. But with this instead. And it'll be like, here's something completely different. You'll be like, no, what?

You know, Midjourney's a lot better than GPT.

Yeah, exactly. And so now I think a lot of people have written off that because they had, you know, maybe a rough experience, uh, originally. And so I encourage everyone to go back to Midjourney or these other tools. And there's just so much better control now around make this, but in exactly the style of the last 10 that you made.

Yeah, for illustration creation or something else. I think for us, we think of AI as like a tool to enhance what it is that we're doing. We're obviously not like replacing content creation in general.

Sean, I'm curious if you have any hot takes on the newsletter industry or newsletters in general, since you see so much both in your own business and, you know, everything that all your friends are doing too.

Yeah. For me, I would say I think some people don't think as much about the design of their newsletter and the importance of the design of their newsletter and how it's presented. But for us in particular, in the health and wellness space, and even in the positive news space in a prior, um, life, I realized the importance of having really quality design, whether it's like a logo mark, word mark, the colors that we're using, how it's incorporated in the design. So it doesn't feel just like a generic newsletter. And I think it helps build trust. It helps with engagement and, um, returning behavior retention. So I think people. Sleep on the importance of design of their newsletter. And that's something we've really valued, like, from the beginning with every project that we've done.

So in the, the spectrum between plain text emails, like, the content is all that matters, and let's heavily design everything. What I see you doing is saying, like, look, these aren't two separate ends of the spectrum. Like, we can actually put these, like, this is a multi-axis problem. It's like, let's have super high quality content. And let's design it really, really well. And with that, we're going to stand out. Whereas a lot of people are just like, eh, you know, I threw some AI-generated content in a generic template and why are people unsubscribing? I don't understand.

Yeah. It's hard to like have trust in something that feels like it's very generic or produced by like someone who doesn't typically produce newsletters.

Yeah, exactly. What's something that well-designed newsletters do in the first 10 seconds that most newsletters never do?

Yeah, I would say for the first 10 seconds, I mean, I think it's important to establish trust with your readers, a connection with them, and then draw them in to read further. So for us at All Healthy, we have our intro text is the first thing that someone's reading that is written by the editor. It's in our tone of voice. It's reminding the reader that there's a human on the other side of the email. So we're, it's an opportunity for us to be like really voicy, reference something timely. Even maybe click out because it can, it's the first thing someone's reading or kind of reference something further down in the email to ultimately draw them in. And I also think it's important to think about the header of your newsletter and how that looks. A lot of people might just like slap a logo on it and call it a day, but it's kind of setting the emotional tone for your newsletter. So something even as subtle as like color can make a big difference. And for us at All Healthy, I mean, we keep it relatively simple, but another newsletter like Dense Discovery, they have a full-fledged illustration artwork alongside a quote to bring, to open things up. That really draws you in and gets you to want to read more. Or you could do something like a mission statement or tagline, kind of reinforcing why someone's opening and ultimately, hopefully enticing them to continue to, to read from there.

I could see that quote having like the instant payoff where it's like, I don't have time to read the newsletter, but I know there's a good quote there and Ah, I guess I'll keep reading and go from there. Right. Like, you know that there's going to, even if you only have 10 seconds to allocate to this email, you're at least going to open it to see if, to see what the payoff is and then go from there. Whereas others you're like, I, there probably will be something good buried within this newsletter that I'm going to be glad I, but I don't have time to go find it within that. Yeah.

And I think it depends on the format and approach of your newsletter too, but the goal would obviously to not have it be getting someone in the habit of just reading that quote and then leaving. You have to kind of find a way to, to draw them in further if that's your goal.

Is there anything with newsletter content about open loops where, you know, you see this in TV shows or something where they like leave you, you know, they wrap up what they're doing and you're like, oh, the episode's going to end here. And no, they actually start a new thing and you're like, right as, and they end it here. Is there anything where, I don't know, you create open loops early in your newsletter where it's like they want to, keep reading or we're going to come back to that. I see speakers on stage do this as well, where you, you, they conclude one story, but lead a question that then like keeps you engaged because you're like, oh, they're going to, what happened there? You know, is the payoff going to be there? And so I'm, yeah, I'm wondering if either you've seen anyone do it well or you all do that to be like, hey, there's something further on that you're going to remember.

I love that idea. I mean, for us, honestly, we only really use the intro text as a tool to do that. Um, but I think that's a fun, a fun incorporation where maybe even like in a featured story, you're hinting at something else that's further down or depending on the format of your newsletter, maybe it's easier to do that and draw them further down or have a cliffhanger at the end for something that's— tease something that's coming for the next send too.

I guess the ideal newsletter would have the immediate payoff that makes me feel really glad that I clicked in, or the feeling of like, I'm, I'm at home, right? We're delivering on this promise now that I'm in the newsletter. And then also the thing towards the end. That is like, but I gotta make sure to stay for that. You know, the just trust me link or the, um, you know, the, the question in 3-2-1 Thursday or, or those things. It's like, I might skip over a few, a little bit of this if it's not interesting, but I'm gonna at least make sure I get to this point. And it's hard to like bookend that and make sure you have, you're delivering, especially 7 days a week on both those things.

Yeah. 100%.

Yeah.

We try to do that with the, the sections I mentioned, but yeah, it's, it's, it's tough depending on the frequency and approach for it to feel organic and natural.

So we're in this state of email is doing really well and we're excited about it and all that, but people might be listening and be like, ooh, I don't feel like my email is doing super well. So I'm curious if you have like a top 3 things that you fix if an email is underperforming.

Yeah, I think it's important to determine what it is that your goals are for the newsletter to start and then work off of that. So like, what does underperforming even mean to you? And if we want to group it into 3 categories, we can group it into engagement, monetization, and retention. And if we're focusing on engagement, like let's say your goal for your newsletter is to drive traffic to web, then analyze your existing format. If it's a longer form newsletter, you're providing all the content to the reader in the newsletter. They're probably not going to want to click out. They don't need to click out. So incorporating a section like Quick Picks where it's like short form enticing, some sort of like tease to get someone to click could work well, or evaluating even the entire format of your newsletter. Maybe it needs to be shorter. Perform. Maybe you need to reevaluate how you kind of have what the sections and structure are of your newsletter as a whole, and then kind of build from there. If we're talking about monetization, I mean, obviously start with focusing on your, um, section, your sponsorship section, and figure out what's working well. I talked about some ideas there in terms of like making it seamlessly incorporated, making it in your tone of voice, taking an editorial approach, um, that can work really well. And if we're talking about retention, so maybe you have like a paid subscription model, or maybe you're just, your goal is obviously to keep people reading Leaving every day in the offboarding user flow, ask them why they're leaving. Try to understand how you're not providing enough value to them if they're willing to provide that feedback to you. And then let's say for us, since we're sending 7 days a week, it a lot of times could just be based on the frequency. Like it's too many emails. Okay. If that's the issue in our footer, let's have the option to like explicitly call it out. Too many emails, click here, give them the option to just receive the email on Sunday instead, rather than have it every single day. So try to understand kind of what the issue is at hand and then find fixes for it and then evaluate and see if that's working.

Yeah, I like that. I like the personalized approach because the great thing with email is you can automate so much stuff. You can set up these systems or a specific link that does, you know, this, this task, and then you can personalize to each individual subscriber. Is there anything that you do kind of at this scale of personalization? Because you can do it. But, you know, then when you have a million plus subscribers, like, do you personalize based on behavior of what they click or their interests or anything like that?

We're starting to a little bit more. It's interesting because like on the most recent survey we had for our audience, it was like only, I think it was 6% of people said that they're like, would like AI recommended curated, um, like things, which is funny because I feel like AI could curate probably better than our, our like editorial team to an extent because it understands what individual subscribers Exactly.

Of like, oh, I can, for this one person, I can tell you here's exactly everything you've clicked on. Here's what you're likely to click on again.

Exactly. So I think we're finding that balance in terms of like the reason that people are engaging with a newsletter in the first place is because they are interested in kind of the opinions and the voice of whoever it is that's producing that newsletter. So leaning into that a little bit more and like sometimes people value the fact that like everyone's getting the same newsletter that day, but at the same time, there could be a certain section that is more curated to that individual based on their interests. And then ultimately it's probably gonna end up engaging better too.

Yeah. I'm thinking about like on my newsletter, I followed pretty much the same format pretty consistently, but I haven't taken this level of analytical approach and like been really thoughtful of like, am I delivering for the reader? And it's more like, this is what I'm interested in and I hope you are too. Yeah. But I'm just even thinking about formats where mine probably follows, like I have the intro which is like a mini essay, and I'm writing a decent amount about that. Like, that might be 200 to 500 words, and that is kind of the bulk of the newsletter. And then I have, um, usually a couple other things I'm linking off to, and always the podcast episode. Um, but I feel like they might be providing— it might be too repetitive. Like, as you're talking, I'm like, okay, from a design perspective, how could change up the format of the podcast episodes since that's a recurring thing that, that comes out, or maybe make the, the individual recommendations I'm making of like, check out this book or this YouTube video, um, or this new kit feature, right? Making those look differently. Um, and so I'm wondering, would you just experiment with that and like try it out week to week? Would you ask for replies? Would you put a poll in there? Like what types of things would you do as you experiment to say like, Hi, dear readers.

Do you like this? Yeah, I think it's, it's all the above. I think, I mean, first of all, make one change at a time, obviously. So it's hard to analyze if you're making multiple changes at the same time. So let's say you're not sure about a particular section or you're like evolving that section, changing the format of it, test it out for a certain period of time and see how people are engaging with it. Do a poll, ask for feedback, talk with, uh, with users or do a survey too and try to get an understanding of if it is working Um, yeah, I mean, we love surveys at All Healthy. We'll do them quarterly and ask, and it allows us to get a lot deeper. In particular, if it's a section that like doesn't require a click, I mean, it's hard to like A/B test it and understand what it is that's working best. Yeah.

You just don't have the, there's no, like on the web you can know, oh, here's what the cursor did over this, or the, the user lingered here at this. And it's like, we know open for the most part and we know click.

Yeah.

Also for the most part. Exactly.

Yeah. And if it is something that you're truly trying to get someone to click on, then I think it's a great tool to A/B test and 50% of your audience, one version without that section or without that CTA or whatever it may be. And then 50%, the other version, that's easy. But then if it is something that isn't more focused on engagement like that, then doing surveys or trying to get feedback from them is, uh, works best.

Yeah. I like it. Sean, this has been a ton of fun. You have a unique insight into the creator economy and newsletter space and all of that.

That.

So it's been fun for you to share, like, hey, here's behind the scenes at millions of subscribers, here's what works. If people want to follow you, check out more of what you're doing, uh, where should they go?

Yeah, I mean, follow me on LinkedIn, connect with me on LinkedIn, send me a message. I'd love to explore what it is that y'all are doing. And yeah, I think that's probably the best place to connect with me, and then we'll love to, to chat.

Sounds good. Thanks so much for coming on.

Thanks for having me.

If you enjoyed this episode, go to YouTube and search The Nathan Barry Show. Then hit subscribe and make sure to like the video and drop a comment. I'd love to hear what some of your favorite parts of the video were, and also just who else you think we should have on the show. Thank you so much for listening.