How to Grow and Monetize your Newsletter with Matt McGarry

I’m Igor Kheifets, and this is the List Building Lifestyle, the podcast for anyone who wants to build a wildly profitable email list working from home. If you’d like to make six figures, travel the world and help people improve their lives in the process, this podcast is for you. I also invite you to claim a free copy of my best selling book, the List Building Lifestyle Confessions of an Email Millionaire at igorsbook.com. Get the free book plus $3,000 bonus package that includes my best capture page templates, email swipe files and traffic blueprints, visit www.igorsbook.com for details. And now it’s time to claim your List Building Lifestyle.

Igor Kheifets  0:53  

Welcome back to the List Building Lifestyle. I’m your host, Igor Kheifets. Matt McGary is a powerhouse in the world of newsletter growth and the founder of Grow Letter, often referred to as the newsletter Guy, Matt, has an impressive track record of helping over 50 of the world’s leading newsletters add more than 5 million subscribers. Grow Letter’s client roster boasts some of the most successful names in the industry, including the morning brew, the hustle, 1440 Cody Sanchez, the daily upside, James clear and many more. Grow Letter is renowned for transforming newsletters from 10s of 1000s of subscribers to millions, achieving seven figure sales in just months. 

One of his clients, the Milk Road, was acquired for between four and 7 million within a matter of 10 months before founding Grow Letter. Matt started his career as a freelance digital marketing consultant on Upwork, where he also gained experience as a media buyer and copywriter. Matt, welcome to the list. Building lifestyle.

Matt 01:55

Awesome! Thanks for having me.

Igor Kheifets 01:56

I’m excited to chat with you because, I mean, it’s pretty obvious that since around COVID, I’d say email newsletters have really been making a comeback. I don’t know what is it about them specifically, but all of a sudden, like the newsletters I mentioned in your bio. So morning, brew, the hustle, 1440 Cody Sanchez, daily, opposite, James clear, I’m like on all of them, you know. So what is it like? What’s going on? Why are email newsletters hot again?

Matt  2:30  

It’s become hot, really, about 2020, and then even more so again, in 2022 and 2023 for a couple reasons, really, two things, it’s become easier and more accessible. So there’s platforms like sub stack, started in 2020 made it way easier to start an email list, start a newsletter. Beehiiv, which I think started in 2022 made it also very easy, but gave a lot more advanced marketing and growth and monetization features. ConvertKit’s been around for a long time. That platform is great too, and has improved a lot. So the accessibility is there, and I think there’s been some big public acquisitions, like the hustle, for example, I used to work there. I led growth of that company. 

They were acquired for like about 27 million in 2020 morning Brew was acquired in 2020 for about 75 million. They’re now doing north of $100 million in revenue per year from their newsletters. Industry dive, which is like a B to B. Media company focused on email newsletters. They were required for $ 525 million in 2021. Milk road had to exit in 2022, for seven figures in like 10 months. And there’s been a couple more like that too. So people see those big names. Other times they see ads for them, because they have millions of subscribers, right? They’re reading them, and then they think, you know, this business model makes a lot of sense, and I’ve been able to work with some of those companies and teach people how to do this.

Igor Kheifets  3:48  

So what is the model? How are these companies making money? Because, essentially, yeah, newsletter, right?

Matt 3:54  

Yeah. So this is a little bit different than like, email marketing, although that’s super powerful, and these companies do that too, right? So we’ll just say morning brew is the one who really pioneered this and was the most successful. There are ones before that, like the gist or even the daily candy and the hustle. Morning Brew came out at about the same time. But so the morning brew model, we’ll call this like a newsletter, first media company. It’s a media company, so they don’t usually sell their own products. They’re usually monetizing through advertising. So Morning Brew will send out a newsletter. Right now, it’s like seven days a week for us in these newsletters, it’s five to six days a week. They’ll have one or the two ads in each of those newsletters, and that’s how they make money. Morning brew has $100 million plus ad business just with that. When I worked at the hustle back in 2020 we had a $20 million plus ad business just through having won the two ads in the newsletter six days a week, right? So that’s the basics of it. I can get into more details too.

Igor Kheifets  4:50  

yeah, I mean, I’d be, I’d love to, because again, the timing of it is really interesting, because a couple weeks ago we launched our own content email newsletter. As you know. Or, I don’t know if you know, but I’ve been in the email marketing game for a long time. I’m one of the emails like, they call you the newsletter guy. I’m like the email marketing guy. So, you know, I’ve been building email lists for ages and monetizing them, but it’s all for the purpose of marketing products and services. I’ve never, ever had an email list where I sent out quote unquote content.  

And if anything, I preached against content for many, many years, because oftentimes, in my kind of subset of this industry, people tend to think that when they sign a subscriber update to send the subscriber content in order to make them like and trust them, and only then after a little while, once every 10 emails or so, you get to send out an offer, and the subscriber because they’re so blown away with all the free stuff you sent them is supposed to be, you know, like in love with you and then giving you money almost regardless of what you’re promoting, which, of course, is not the case, like lists built for the purpose of marketing. You market to those lists every day. You make an offer every day. There’s a bit of personality in it, but it’s not heavy content driven. So this model is very different. There’s way less marketing there. It’s more about the content. It’s more about the news. It’s more about maybe the personality of the person writing. Perhaps, I know so I’d love to explore and better understand what, how, how this model works, and what makes it so interesting or valuable that, you know, a bunch of companies end up investing hundreds of millions of dollars in these acquisitions. 

Matt  6:42  

Yeah, both models work, and there’s some companies who do both well. But you know, in the email marketing model, you’re sending out marketing emails every day, essentially to sell a product, and usually you want someone to either buy or if they don’t buy, they’re not going to be useful to you. Right? In the newsletter, the first media company model, we want someone to keep opening our newsletters literally every day, and we want them to keep doing that pretty for years, because we get paid when they open an email and when we get that impression for the advertiser. So it’s really somewhat opposite in many ways, where we want them to stay on the list for one plus year. We want them to open 50% of emails you open, you know, three out of five emails, we send them every week, and they stay on the list for a long period of time, and we make, you know, between $10 to $25 per year from that subscriber through sponsorship sales. And so, because it’s all about retention and high engagement over a long period of time, marketing emails in that model can be counter to what you want to do, because that’s going to cause more churn, right? That’s going to cause more unsubscribes. 

Not that you shouldn’t be doing marketing emails when you have a media company, but the models are like, are very different. And there have been some people who have done both well, like at the hustle, we had an ad supported newsletter, $20 million plus per year business. And then they built out a paid information product that was a three inch dollar a year, prescription subscription had 15,000 plus paid customers, 300 bucks a year. And of course, they did marketing emails to sell that product. And that’s the most effective way to sell a product, is through marketing emails. So there is a way to do both, but the challenge, this almost becomes a challenge this almost becomes a challenge when you have to do a book, because now you have to segment your list, and you can’t send those marketing emails to everybody, because you have this big ad business that you’re building as well. 

And of course, you can have call to actions within your free newsletter too, but that’s kind of how they differ. There’s not really a right way or a wrong way to do it. There’s just different paths, right? And so the one advantage to the newsletter. First media company model is you may be able to build more enterprise value in more of a brand that then could be sold or acquired by another company. And that’s why I think we’ve seen a lot more newsletter first, media companies go on to get acquired, like Milk Road, the Peak, Morning Brew, etc, because they have a brand that people value, versus if you’re just a creator who has an email list that’s sending all marketing emails, another brand couldn’t take that over and get value from it, or it couldn’t be a strategic acquisition. 

The best example is HubSpot in the hustle. So HubSpot, a billion dollar software company, bought the hustle in 2020. They bought that company because they wanted to grow their audience so they could go and sell more HubSpot software, right? So the hustle had a one million, two million person email list. They had a very talented media team to create media and content. They had a podcast too. And so that was their strategic acquisition by HubSpot to grow its audience and continue to create more media so it can have a bigger audience over time and sell more HubSpot software. If that was just like they couldn’t go out and buy, like, an email list from a creator who’s just sending marketing emails every day, because that wouldn’t be strategically valuable to them. So those are some of the differences between the two.

Igor Kheifets  9:50  

Interesting. Okay, so let’s say someone’s listening and they’re starting a newsletter. What would you say are some of the fundamentals that they need to have in place. 

Matt  10:03  

Yeah, I like this right growth cell framework. So it’s like, what is the content we’re going to be sending, and when are we going to be sending that? So for most people starting out, it should be a weekly newsletter. It’s very hard to send editorial, high value content every single day. You need to wait to do that later. Really, the only time you should start increasing your editorial newsletter is when you’re selling ads. So you’re basically only sending the ad inventory that you have. So start weekly at first, because you need that cadence to engage people on a regular basis. And then as you start to sell a ton of ads, then you do two times a week, three times a week, etc. You also got to figure out who you’re writing for and how you can help them. I won’t get too much into this, but, you know, it’s the basic things of like, you know, picking a niche. 

I don’t recommend people go super broad. If you’re trying to be everything for everybody, you’re going to be nothing for nobody, right? So start niche or than you think, I like to kind of pick a niche or a category and then go to levels below that. Because the good thing about going niche is you can always go broader later. It’s kind of hard to go abroad and then go niche later. So I recommend focusing on the niche right now. You kind of want to reverse engineer a niche based off of where the money is. It’s just like with female work and just like with any business, right? So where the advertisers are spending a lot of money in email newsletters, pick the niches that they are advertising in. So some of those niches are things like B to B. So marketing, HR, many different B to B niches that are serving other industry professionals, finance and investing is big, making money online, building a business, things like that. Those all great niches. There’s many, many more, too, but those are some of the ones that come to mind. 

You don’t have to be in one of those, but you want to be where the advertisers at, or you want to reverse engineer from how you’re going to make money in your business, right? And then you need to start sending the newsletter. And I really recommend people start with a minimum viable newsletter, like, don’t go out and try and create some crazy thing that’s like a 10 minute read time. It takes four hours for you to craft every single week. Ideally, your newsletter should have less than a five minute read time, and it’s only going to be a handful of sections, maybe between three and five different sections. You might have an introduction section that has a table of contents for what you’re going to cover. Then you might have a main content section where you deliver a 300 to 500 word story. It could be an article. It could be a listicle. Could be summarizing an important news story. You might have a curated section where you’re recommending other content that’s relevant to your audience, and then you kind of have an outro section, and then a lot of times, we’ll have a poll, which basically says, how’d you like today’s newsletter? Five stars, three stars, one star. 

And then that’s it. So the newsletter in total, has like three to five sections, it needs to be repeatable. So you can do this every single week for years. And then also, so you can ramp that up to multiple times a week for years, because we’re really, we’re doing things for the long run here, right? And also, if you make a repeatable format like that, then it can be outsourced, right? If it’s so complicated and hard that only you can write it, then you’re never going to be able to hire someone to do that for you, or use AI to help you do that in some way, right? So not saying don’t make it challenging, but don’t make it too hard on yourself, especially when you’re starting out, because this stuff is going to evolve. Your first newsletter is going to look very different from the 10th newsletter that you write.

Igor Kheifets  13:13  

Interesting. Okay, so when do you think? Like, how would you give you my question, why would someone read your newsletter, especially if you’re sending, like, three to 500 word articles, if they are already getting a lot of that stuff over social media and other places, like, what exactly differentiates the experience for them?

Matt  13:39  

Yeah, you gotta think about like, what’s your job to be done? Like, how is this actually gonna add value to people? And so if you’re posting generic content, basic information, or things that you’re also posting on social media, people aren’t gonna subscribe for that, right? So everybody’s insights are gonna be unique to them. You wanna find the combination of like, what the market wants and what you have to offer, and then also what you can monetize and find something that’s in the middle of that Venn diagram. It’s hard to answer this unless I really know you know who we’re speaking to. For me, it’s been basically taking information that wasn’t really publicly available, basically information you couldn’t if you Googled it, you couldn’t find a good result for that information, right and delivering those insights in a weekly newsletter, right? So I have a lot of experience working with these companies. Some of the ones we mentioned, I kind of took my learnings from those I shared that in the newsletter. And especially, you know, a year ago, when I was first doing this, a lot of people had never heard of these things before. So if you have deep experience in the industry or through your life experiences that are just not common knowledge, you have a big advantage, right? But that’s not the only reason why someone read a newsletter. A lot of people read a newsletter to save time. So it’s like, would you rather Doom scroll through social media to get your news, or maybe you can read a concise, entertaining, funny version of the news that’s five minutes and it’s an email newsletter. Yeah, that’s kind of what Morning Brew has done, or the Hustle has done, or 1440 which is another newsletter with like, 3.5 million subscribers now and eight figures in revenue. So a lot of times, you know, saving people time can also be just as valuable as delivering unique insights. So there’s lots of different ways to approach it. Those are usually the two things that I think about interesting.

Igor Kheifets  15:20  

I want to ask you to do a bit of a highway rect and put me on the spot. I’m kind of putting you on the spot, but I’m putting myself on the spot. So I sent a link in the chat. You should be able to see it there . It’s the third issue of my newsletter. The newsletter is called the independent income Insider. I didn’t really advertise it much yet, we are at a point like you said, one a week. We’re trying to do two weeks now because I got, you know, I got a team so we can get away with more, with a bigger investment. So I would love for you to go through it. And you know, don’t hold back, but you know, offer your insight. Rip me a new asshole. I mean, do whatever you want. Just tell me, what am I doing wrong? What should I do differently? How can I improve? 

Matt  16:13  

Yeah, so first of all, I think it’s a little bit long, and that’s totally okay, especially because it’s weekly. But as you start to send two times a week, three times a week, I would try and like, copy and paste the total words and listen to like, a read time generator and try and name for the total thing to be under a five minute read time. You might be at that now. You might be a little bit over. It’s not crazy long, because you want people to be able to finish it, because if they can finish it, they can keep coming back for more. If they never finish it, they’re not going to come back for more, right? Overall, I like the format. So you basically have an intro section like, welcome to the newsletter, explain what it’s about, and then you give what we call like a table of contents. And today’s issue, here’s what we’re going to cover that’s really important, because you’re creating an open loop and teasing what’s going to be within the newsletter below. 

So people actually keep reading it. And also maybe can, people can go to like, maybe they want bullet point number four, and they just go straight to that. You want to make a newsletter, kind of like a magazine or a newspaper, where people can pick and choose what they want to read like no one’s. People will read all of it, cover to cover, but most people are just going to read a couple sections that are most relevant to them. So the newsletter, or any newsletter, should really be the same way. So I like that you also have custom dividers here between each section where it kind of has, like your logo, which I think is important. Like, you obviously need to have dividers between the sections so they’re identifiable, identifiable as different sections. And then you have, this is getting into the details here, but like, you have what we call a section heading, and then you have a headline for, I think, almost every single section, and that’s good, because it just makes it skimmable, right? So like, I can go see what section headings and what headlines interest me, and I can go read that content. 

It makes it really easy to get entered into the newsletter for the interesting part. So I think that’s good. I don’t have time to actually go and read through all the content, which is an important part of a newsletter, obviously, but there’s also a lot you can do with, like, just the design. So one final thing I would say about design is like, consider adding in some boxes. So right now you have dividers. Basically a box is just a line around the entire section. I think that really elevates design, and we’ve seen higher engagement when people use boxes versus dividers, you can still use dividers for some sections, especially if it’s a very long section. But if you look at Morning Brew, everything is in boxes. It’s very elegant, very easy to read. I’d also add in, like, a little bit more color here, so like your newsletter is black and kind of gold, you can make the section headings gold font that would add in a little bit more color, the maybe one or two more things I would add here is like, can we add content that’s a little bit more timely or more news oriented?

Igor Kheifets  18:57  

Yeah, that’s what I was thinking, because it is called a newsletter. And you know, you did mention that part of what makes the newsletter valuable, it kind of gives you the news, sums it up for you, saves you time. And there’s lots of newsletters I’m reading that do exactly that they give me, like the stock market news, the Trump being, you know, found guilty on the hush money, trial, verdict, etc. And I’m thinking, I’m writing in a newsletter about making income independent, basically being financially free. There’s like, I mean, there’s no, there’s no news that makes sense. 

Matt  19:38  

Yeah, yeah, it’s um, and that’s, that’s totally a challenge so many people face. I do too. In some ways, I think about like, what in the news? It doesn’t have to be national news, like some of those stories, but like, what in the news would be like most relevant to this, or could be relevant to this, and it doesn’t have to be like necessarily what you might think is news. It could be like something that, like, like you mentioned Gary Vaynerchuk in this or someone that is in this space, like something that they did, they wouldn’t really be newsworthy. There’s not an article about it, but maybe Gary did a social post about it, or he released a YouTube video about it. So it doesn’t always have to be news, but like, it could be things that I would call more like events, or things that are a little bit more current, and you don’t want to force feed people news that is relevant. 

So definitely don’t do that either. In evergreen content is great too, in many ways, because you can reuse the best stuff over and over again, right? So there’s some way to make it work. You don’t necessarily need to add more to this. You could have a section that’s more like curated content, where you basically have one line or a couple sentences recommending that thing and, like, that’s your news content, or that’s your current event content. That’s kind of what I do. Like, my newsletter is basically just one deep dive into a talk about growing your business. That’s maybe about 1000 words. But before that, I have, like, curated section, section that has different links around, like industry, new news related to email newsletters and media. And then I have different topics, like I have a topic on deliverability, on growth, on revenue, and then I link to relevant things that happened that week around those topics.

Igor Kheifets  21:16  

Where do you find the relevant things that happened? 

Matt  21:20  

For me, I basically have, you know, Twitter and LinkedIn. People I follow write them, book and marketing things throughout the week. But that’s not the majority of where I find things. There’s really about, you know, over time, as I’ve done this, I’ve written this newsletter for like, a year and a year and a half now, I found probably about like a dozen sources. This could be other newsletters, websites, blogs that I’ve gotten a lot of value from, and I, you know, they share relevant things that I want to share with my audience. And I basically have those sources in a spreadsheet. And every week that I’m creating my newsletter, I go and check those sources. So that’s what I do, and that’s it’s really kind of the same for everybody. Every newsletter writer I’ve talked to, they have, maybe some people might have 100 sources, if they’re going really crazy, but like 10 sources, then they have like social media accounts that follow you might even want to have like list on Twitter of like, just the relevant accounts to like this newsletter. So it just saves you time, because it does take time to curate this stuff, even though it might be 10 links that might take half an hour to find the most relevant things, an hour sometimes. So you got to have a system. 

Igor Kheifets  22:21  

Interesting. Yeah, I really, really need to think through on how do you get the news into the newsletter for something like this? Because on one hand, it’s great, because you don’t have to really follow the news or stay current and what we do, because a lot of the stuff that makes you money is timeless, but at the same time to make it relevant and to make it relevant now, like, maybe, I mean, what do you think about playing on current events? So, for example, the whole Trump trial, right? What if I found a way to spin it into something to do with independence, or something to do with income, or, what if…something like that.

Matt  23:06  

yeah, exactly. That’s probably not the best example, but there are examples out there that you can do that with. So like, so for me, it might like, like, the BuzzFeed. BuzzFeed going bankrupt. I could spin that article and talk about how it’s important to own your audience and be building an email newsletter, because Bucha is BuzzFeed relied on like Facebook and Twitter to reach their audience, and when those algorithms changed, their business changed and declined to so even though that article has nothing to do with like newsletters, I can still talk about the BuzzFeed bankruptcy, filing of the Bugs feed like stock drop in my newsletter. So those are the types of things that I would do. They’re also like, if you know, I love what morning brew has this section in every newsletter where it’s like, it’s basically like a market update, where it’s like, S, p5, 100, here’s the change, here’s the year to date, results, etc, etc. Like the bond market. I would love if you can have something like that. I don’t know if that would work for this, but if you have a recurring section that keeps people up to date on like news in a data backed way, I think that’s really cool. The Milk Road is a crypto newsletter. Obviously, they’re giving crypto prices like Bitcoin and Ethereum. They also did like a fear and greed index in every single newsletter that people really enjoy, even something as simple as, like, weather, that’s been something a lot of newsletters have had success with, especially if it’s a local, a local newsletter, obviously.

Igor Kheifets  24:26  

Well, obviously, yeah, yeah, yeah. We, in our industry, we don’t really have a market that everyone can look at for up to date prices and whatnot. I mean, we could perhaps come up with a way to like, average cost per click, or average cost per lead per industry this week, but I’m not even sure if this data exists. 

Matt  24:50  

You know, yeah, it’s tough in that that might not be the best fit for you, but for someone else listening, there might be something like that they can include. I’ve also seen some newsletters that are focused on like fashion, for example, in their posts. In the stock prices and changes of like, the biggest fashion companies, so like Nike, Lulu and stuff like that. So there’s ways you can get creative with it, but you don’t have to have stock prices. I like the idea, just like a curated section, too. The final thing I would say about the newsletters like, I think you could probably find one section to cut, because especially if you’re adding a curated Section N, I think there’s one section that, like, people don’t really love that you could probably cut and just make it shorter. And then, sorry, actually, one more piece of advice is, like, you should have a poll at the very end. Have you seen a poll in a newsletter before? Yes, yeah. So you’re asking people, like, how do you like today’s newsletter? I say, like, love it. It’s okay, not great. It’s usually three responses, and like that will make your life so much better, because you’ll get a lot of positive feedback, constructive feedback, and then you’ll also get, like, people will say more than just the poll response. They’ll say, love it, and then they’ll tell you why they love it, or they’ll tell you why they don’t love it. And when you’re sending an email, like, all you see is open rate, click the rate, unsubscribes, maybe spam, and that’s really not all that helpful. And to see how people really respond to the content. So doing a poll will help you see how people like the content, right?

Igor Kheifets  26:13  

So I’m just writing down all the things, trying to sum up everything you don’t, because it’s quite a bit. So the first thing is reading time under five minutes recommended

Matt  26:27  

ideally. And there are some great newsletters that break this rule, but that’s what I’ll recommend for something like this.

Igor Kheifets  26:32  

Okay, a poll at the end. Did you like this newsletter? Yep, okay, a box around each section, yeah? 

Matt 26:42  

I think that’s going to help. And I’ll send you my kind of design template too. I have that on my side so I can kind of tell you, like, what box specifications you should have. Um, okay, keep going. 

Igor Kheifets  26:54  

Okay, cool. Now, news or newsworthy, or play on current events, that’s going to be powerful.

Matt  26:59  

Yeah. And then also, like, who are you? I think really people would value like, you know, like Igor is bookmarks. Like Igor is from the desk of you. Like, what do you like reading this week? Like, what did you like? Like? So, like, if Gary V shared a piece of content, you got a lot of value from that you published that week. You can share that in your newsletter, and you can link to

Igor Kheifets  27:18  

that. Well, actually, we do have a section there. If you scroll down, you’ll see a book section, and I’m offering, yeah, for a book and why I liked it, and what I think you will get from Yeah, I think that’s helpful.

Matt 1  27:29  

I think you can do even more of that in, like, a shorter format too. Obviously, you can’t do five book recognitions like this, because it would be the whole newsletter. But you can have like, different things so that, like, current event content, like, current event content, like, it doesn’t always need to be news. It could just be like content that you found valuable, that was published

Igor Kheifets  27:45  

in the past week. Okay, got it? Um, curated section, so five to 10 resources or links of the things that I liked, yeah,

Matt  27:54  

and you don’t have to have this kind of like news section, and a curated section could be the same thing. So for me, it’s the same section. I don’t want you to go overboard and add a bunch of different curated content, because it’s more of like a bonus. Really, people are coming from, like, your original content that you’re creating, right? That’s where they’re getting the most value.

Igor Kheifets  28:15  

Okay, yeah, well, so we decided to put in a riddle in there as well. You know, because many of the newsletters have riddles, and I personally enjoy them, because I was like, I like, I like riddles, and then the next day I’ll go check for the answer if I’m not sure I like that. 

Matt  28:31  

That’s really smart. And I love trivia, riddles, quizzes, anything we can get people to interact where they can think about it. They can reply to their answer, or sometimes you can even do that through a poll where you can, like, give them a multiple choice answer, and they can answer in that poll. It’s, I mean, it gets people to reply because people don’t engage, which is great, but also, like, that’s gonna improve your send, your reputation or deliverability, because you’re getting more clicks, more replies, and so you’ll have higher engagement overall for the newsletter.

Igor Kheifets  29:01  

Okay, anything else that I missed? 

Matt 29:05  

I think that’s good. I think just like when you add this new section in, like, what’s the section you can cut, and then, because I think you have a lot of sections here, you have, like, one, I won’t count it out now, but I mean, you have, like, over four. 

Igor Kheifets

So that’s too much?

Matt 

I think you’re gonna find that, like, maybe one of these isn’t as necessary. I could be totally wrong, because I didn’t have time to read it word for word, the whole thing. But if you feel like one’s not necessary, don’t be afraid to cut that. So I would say another thing you can do later on is, like, do a poll or a survey that we can get a little bit more data from the audience, where you can ask people like, what is your favorite section in this newsletter? And then have another question that says, What is your least favorite section in this newsletter? And then can you explain why? And that’s how you might make that decision. Another thing, if you want to get you more audience feedback, is like jumping on a call for a couple readers and then just having them share their screen and pull up your newsletter and then just have them like, tell you how they read it. I. Because a lot of times how a user uses your product or reads your newsletter is different than what you may expect. Like a lot of times people just totally skip the intro, and they might go to a section in the middle, and a lot of people don’t realize that. So that will give you data that you just can’t get through a survey.

Igor Kheifets  30:16  

Interesting. Okay, now, what are some of the things that you’re not seeing in the newsletter right now? Stuff that you wish you I mean, with the newsletters you worked with was important, but you’re not seeing the newsletter right now. 

Matt  30:33  

I don’t know, because everybody’s a little bit different, right? So, like we talked about the news stuff, there’s no, like, perfect way to do this, right? We have some people like, like, a linear newsletter. He has a paid newsletters doing like seven figures in revenue. Like, every newsletter is a deep dive. That’s like, 1000s of words, right? There’s no news content, there’s no curated section, and then there’s Morning Brew is doing 100 million basically, curating content from other sources, like Wall Street Journal, New York Times. So I don’t think there’s anything missing. The one thing I just think that matters most is just talking to the readers, getting feedback, because that’s really how you improve. Like, there’s like, there’s a lot of theoretical stuff that we have as writers where we’re just like, oh, maybe people like this. Maybe people will like that, but there’s no better way than actually just hearing what they want. But you also have to ask for that too. So ask through it through a poll, but also like, ask people to reply to the newsletter. Like, Hey, What content do you like to see? Is there anything we can fix? We can make it better about this newsletter? Reply to this email and let us know you can do that at the top of the newsletter, the bottom of the newsletter, that’s really where you’re going to get value. And then I like to think about, if someone gives me a good answer, I’ll just write a whole newsletter for that one person, even though only one person asked the question, I know other people have the same question too, right? It’s going to be, it’s just how things work. You know, if one person has the question, 100 other people too, as well. So that’s kind of how I’ve got a lot of my content ideas. 

Igor Kheifets  31:58  

Interesting, yeah. What do you think about a section titled, like, a question from a reader or something.

Matt  32:03  

Yeah, I like that. And that’s like, you’ve seen, like, magazines back in the day where it’s, like, your prudence, yeah, exactly. There’s been a popular magazine, you know, section for decades, and so that totally works on newsletters. And that’s one way to get ideas on, like, what to include in the newsletters, to look at, like, physical media. A lot of people don’t do that. I’m trying to do more of that now, like I used to read like the National Enquirer, to get headline ideas, and you know, that’s why I follow from that, from that type of stuff. So that stuff totally works. 

Igor Kheifets  32:34  

Okay, well, let’s talk about growing the newsletter. Then many of the companies you worked with have grown into the millions and millions of subscribers. So give us, I mean, how? 

Matt  32:46  

Yeah, I’ll walk you through that. So there’s really just a couple of different channels that work for newsletters, and then I’ll break down the tactics within some of those channels. So one is like social growth. So publishing on social media could be any platform, oftentimes that’s LinkedIn or Twitter for B2B newsletters, Instagram or TikTok for others, growing your audience on social and converting that into a subscriber, right? The other one is what we call email platform growth. So using a newsletter referral program, for example, a lot of people have seen Morning Brew’s referral program where you share the newsletter of friends, you get rewards that could be forwarded to a friend that could be cross pointing of other newsletters, that’s newsletter platform, or that’s email as a channel. And then the third one, and the one that a lot of newsletters is used to scale to millions or 10s of millions of subscribers, is paid acquisition. 

So running ads to get subscribers. Usually those are going to be social ads, things like Meta, Facebook, Twitter and TikTok. There’s also other channels too, but those are the three channels. I recommend focusing on another channel that may work for another business is like SEO search as a channel. We haven’t found that to work very well for newsletters. There’s just not enough volume there, and you’ll try to get millions of subscribers from Google search for a newsletter, you may get customers, and that may build a huge business, but it’s not a great channel for newsletter growth. So like, I really think everybody needs to be doing social as a channel. Like, we’re creating a newsletter, we’re creating a content business, so we should be posting content on social too. I really recommend focusing on one social channel at a time, especially for people who don’t already have a following or a team. 

If you already have a huge following the team, that’s different, right? But one social channel at a time, I really like the text based ones, because we’re writing a newsletter. So like Twitter, LinkedIn are super powerful. One thing I focus on is like, making sure that all of our conversion rate optimization on our profile and our post is well done. So a lot of people, they’re just like, publishing on social media all the time. They might have a link in their bio for the newsletter, and they’re like, why am I? Why am I not growing my newsletter? It’s because you’re not focusing on and converting followers and subscribers. You’re not converting, you’re not focusing on converting followers into subscribers, right? So every post needs to have a call to action for your. Newsletter in your profile copy, there needs to be a clear call to action for a newsletter. 

You don’t want to use a link tree. You want to direct people directly to your landing page, because that will have the highest conversion rate, like in your profile header image, you got a call to action for the newsletter. All that’s really powerful. And if you don’t do that, you’re just not going to be able to convert people like you could. You can also use things like lead magnets to even get an additional incentive to sign up for the newsletter. I won’t talk about every single tactic. Maybe I’ll get into like paid acquisition, because that’s really what I’ve focused on with the newsletters that we work with. And that’s how you go from oftentimes, people start that from day one, but that’s how a lot of newsletters have gone from 50,000, 100,000 to 2 or 3 million subscribers. People like Cody Sanchez, Bloom, you know, the Hustle, etc. Like, you know the hustle we probably started out with about 100,000 subscribers from organic content, and then to go from 100,000 to 2.5 million, it’s all paid acquisition. 90% of that growth is paid acquisition. So that’s what I’ve specialized in. And done that for a lot of people. What would be most helpful to cover, like, what platforms work best? Like, how to use those? 

Igor Kheifets  36:05  

Yeah, that was my next question, actually, because we put ours on BeeHiiv. It’s a platform that came recommended by a guy who suggested we start a newsletter. So we went with it. But we also use ConvertKit, and I’ve definitely heard of sub-stacks, and I’d love to know your opinion on these platforms. 

Matt  36:24  

Yeah, I can break that down. I can also share a little bit more on, like paid acquisition, like the details of that too. But for newsletter platforms, the only ones I would really consider now are Beehiiv or ConvertKit. That doesn’t mean there’s not other good ones out there, but those are the only ones I would even consider, especially for starting brand new today. For the first time, my personal favorite is Beehiiv. I am like an affiliate. I am a small investor in that company. But I’ve been using it since January of 2022 and like, I think it came out in 2021 or late 2021 so I’ve used it with a lot of newsletters, the milk road, a ton of other ones. And what I like about it is as a combination of, like, very easy to use, but also advanced features. You know, if you ever use, like, confusion soft, which I think is now called confusion soft, like Beehiiv, is not quite like that, but you still have a lot of advanced stuff you can do. You can do email, automations, segmentations, analytics. I won’t break down the features, but you get the idea. So I love Beehiiv. ConvertKit’s also awesome. Big fan of Nathan Berry and all the people over there, but, um, those are the two I consider. And you can kind of like, do a free trial of both of those and see what works best for you.

Igor Kheifets  37:31  

 Yeah, I do like Beehiiv. I think it’s, I think, just like you said, easy to use, but super advanced features. I also love ConvertKit, but I use it more for the marketing part of what we do, and I didn’t consider it as a newsletter. First platform, from what I’m seeing, Beehiiv is like a proper news content, news focus only, yeah, yeah. 

Matt  37:56  

They’re focused on newsletter first companies, because convert behavior is built by the team that was early at morning brew. And when I first used Beehiiv, I was still working at the Hustle, and I was like, oh shit, this platform has features that, like our engineering team built at the Hustle accustomed to us, but it’s like, out of the box of Beehiv. It’s like they really get what you need for a newsletter, first media brand. And like, one thing I’ll say about that is you’re able to see subscriber analytics by growth channel, which is very important. And with ConvertKit, with pretty much every other platform, you can’t see that, or it’s hard to see that. So you can see like, if I’m running Facebook ads, what’s my open rate, click through rate, unsubscribe rate and upgrade rate from Facebook ads, versus Twitter ads, versus Twitter organic, versus Google search, versus any other UTM parameter or source that you can track. And so you can see, okay, where should I be spending my time and money investing in to grow? And that’s really powerful. And I just don’t see that available of other platforms. And so that’s one of the biggest reasons why I use it. 

Igor Kheifets  38:55  

Yeah, they’re really good so far. So good for us. I’m really happy, although it’s still early days for our newsletter, I’m still, you know, I have my doubts about growing it organically and Beehiiv, I believe, has this network right where you can acquire subscribers and you only pay for them once they’ve I believe, double confirmed and opened at least, like three emails or something.

Matt  39:22  

I think there is a verification process. They actually kind of keep that behind closed doors, because they don’t want people to know, because if you know, then it can be gamed. So that’s kind of, but it’s something like that. You don’t have to double opt in, but you need to open and click a certain number of emails. Yeah, I like that. 

Igor Kheifets  39:38  

I like that very much, because, as an advertiser and somebody who has actually been involved in both buying and selling email traffic for many years, I know firsthand the amount of fraud that can be done with traffic and every year just gets worse in terms of general internet media. Because, I believe it was pre COVID. When I read this article that stated that 40% of all internet traffic is fake, and might be even worse today, I wouldn’t be surprised that number is half now. So knowing that you’re getting a confirmed lead, a real one that opens and clicks, it’s very attractive. It’s very attractive. I

Matt  40:24  

think it’s powerful. And I don’t know if I can say their systems like totally perfect, or if any system is, but they’re doing a good job, and they have a lot of people working on that. And yeah, like, the thing is, with email, it’s like, you have more data on the audience than the other channel. That’s powerful, but, yeah. But also, there are some bots. There are some um, real subscribers who will have bought clicks because they’re subscribed from a corporate email or a, you know, education email, and, you know, everything that goes in and gets clicked by a firewall. You also have, like, Apple Mail privacy protection that’s going to create fake open so there’s no, it’s has only gotten more difficult and difficult with like ATT and mail privacy protection, where you have almost less and less data than we did a couple years ago, but you still have more than ever with email. 

Igor Kheifets  41:13  

Well, let me ask you one more question before I let you go. You’ve now been involved with, you know, at least half a dozen of major newsletter brands, many of which got acquired. You probably know about the game more than most. So looking back on all your experiences in the newsletter industry, what would you say has been the primary lesson you learned, or the biggest lesson you learned that has led to more newsletter success than anything else?

Matt  41:44  

Yeah, I don’t. It’s a tough one. I think the lesson, I would say, is there’s like, there’s no shortcuts in this, because everything has to be working together at a very high level, and you have to execute each part of your business. So going back to the right gross sales framework, like you have to write amazing content that’s unique and that is not just like generic, right? You have to be amazing at growth. So you may need to be amazing at growing on social media, you have to be amazing with your Facebook ads, creating unique creative and setting that up properly, creating the high converted landing page. Like, you can’t half ass growth, you can’t half ass writing, and you can’t half ass selling. You actually need to be able to monetize that list. So you either need to be able to sell them a product through email marketing or through a funnel, or you need to be able to go out to advertisers and sell sponsorships at a high rate, and that’s something we didn’t have time to get into. That’s a whole and also it’s not something I’m an expert at. 

I’m more on the growth side, but that’s a whole nother challenge too. So you have to have all three of those pieces working together to scale a newsletter, and you have to be executing those at a high level. And the final challenge is, like, it’s really all about monetization. A lot of people spend a lot of time like writing and growing, but not a lot about not a lot of time trying to sell products or sell advertisers. And I would focus on getting that part right, because really, with that you don’t have a business. There’s a lot of people kind of like to play business. It’s like, Oh, I’ve got 1000 newsletter subscribers, and that’s awesome. I really encourage everybody to start a newsletter and do this, but try and get that first dollar as soon as possible. It doesn’t matter the source, if it’s an advertiser, if it’s an affiliate recommendation or whatever, like, start trying to make money immediately, because that’s when it’s important. That’s what’s going to keep you doing this for a very long time. 

Igor Kheifets  43:22  

Okay, all right. Well, if someone’s thinking about starting a newsletter, or already started one, and looking for help, how can they perhaps reach out to you? And if they do, what can you do for them?

Matt  43:34  

Yeah, there’s two ways. So if you go to newsletteroperator.com that’s my newsletter, where I have a ton of free content about helping you build a newsletter business. I also have a podcast called newsletter I better you can search and listen to so if you want to learn from me, go there. If you want to work with me in my agency, that is growletter.co and that’s probably for newsletters who are north of 50,000 subscribers, north of 50k in revenue, who want to scale and spend a ton of money to grow their business. So that’s Grow Letter, but for most people, it’s gonna be newsletteroperator.com and read my free stuff. 

Igor Kheifets  44:08  

Awesome. We love free stuff. So there you go, guys. Matt, thank you so much for taking the time to break newsletters down for us. I’m pretty sure most people listening had no idea how lucrative content newsletters can be. But what I do love about this is that it’s still all around email. And I’ve been telling this for years, email is king. It’s the best way to make money online, to push products, to sell, to get attention, and you just generate the best possible quality customers and followers and fans hands down. So appreciate you taking the time. Thank you for making an appearance on the List Building Lifestyle. 

Matt 44:36

Yeah, thanks for having me. 

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