TCC Podcast #396: How to Get Your Emails Opened with Matt Brown

We’ve been talking a lot about email on the podcast lately (see the last four or five episodes). But getting your emails opened takes more than good copy. So for the 396th episode of The Copywriter Club Podcast, Rob spoke with copywriter and email deliverability specialist, Matt Brown about all the non-copy things you need to know about getting your emails opened. And…how to add deliverability and ESP management to your services so you can attract long-term email clients. This is a good one. Click the play button below, or scroll down for a full transcript.

Stuff to check out:

deliverabilitynow.com
The Copywriter Club Facebook Group
The Copywriter Underground

Full Transcript:

Rob Marsh: Looking back at the last four or five episodes of this podcast, you might notice a theme. It wasn’t intentional, but somehow the last several guests have all focused on email, email strategy, and creating or running a business focused on a regular or daily email. For some reason, email seems to be having a moment. Maybe it’s the rise of new email platforms like Substack and Beehiv that make writing emails and growing an audience easier than before. Or it might be the fact that it is getting harder to connect with a regular audience on social media… posts, tweets, reels just don’t reach as many people as they used to. And paid ads on those platforms are getting more expensive and less effective. So attracting an audience that you can connect with regularly with email is as important—maybe more important—than ever before.

Hi, I’m Rob Marsh, one of the founders of The Copywriter Club. And on today’s episode of The Copywriter Club Podcast, I interviewed copywriter and email deliverability expert Matt Brown. I wanted to talk with Matt because it’s one thing to write and send emails and quite another to do what it takes to make sure those emails actually arrive in your reader’s inboxes and get opened. It happens less than you think. And Matt knows how to fix that. He shared a lot of technical stuff that you have to get right. If you know this stuff, you can be far more valuable to your clients that if you just hand over a google doc with the text of your emails. This is a skill set that can result in long term relationships with great clients. So stick around.  

Before we jump into the interview, I want to let you know about an upcoming training happening in The Copywriter Underground on this very topic. After recording today’s interview, Matt mentioned that it can be tough to wrap your head around some of the ideas he shared without a demonstration where he opens up an email account and shows you how to make adjustments. So he offered to show us exactly how to make sure your emails land in the inbox in a training for members of The Copywriter Underground. If you’re listening to this episode and think, I need to know how to do this, or I want to be able to offer this skill to my clients (and earn thousands of dollars from them in the process), then this training is for you. Go to thecopywriterclub.com/tcu and join the Underground today. And we’ll send you details on how to access this incredibly valuable training.

And with that, let’s go to our interview with Matt.

Matt, welcome to the podcast. I reached out to you because we’ve been talking to so many people about email. I feel like there’s kind of been a change around the way people are thinking about email with all of these new tools that have come online in the last couple of years as far as managing email newsletters and that kind of thing. So I thought it’d be really helpful to have you on, but before we get into all of the things we want to talk about email, tell us how you became not just a copywriter, but an email deliverability expert and copywriter.
Matt Brown: Yeah. So I’ll give you the long story since we’re on a podcast together and it has the inciting incident from a story and then the point of no return. I think this was back in like 2019, I kind of got my start in marketing and SEO and content writing, and then I wanted to learn more about copywriting. And I kept learning about that. And then I started working with people who were doing course launches and sort of Jeff Walker style product launch formula emails and for a few years, I was working with people where I’d write my 12 emails, 15 emails in a Google doc, and then just send it over to the client and say, Hey, here you go. Let me know what you think. Let me know if you want any edits. And then we’d work on the copy from there. And then either they or their team would load the emails into whatever email platform they were using. And I was like, great. And after the launch, we’d check in like emails did great. We loved it. Yada, yada, yada, that sort of thing. 

But I was working on a launch—’ll have to go back and figure out exactly when this was, but it was 2019, 2020—and my client was like, Hey, Matt, our ActiveCampaign person just bailed on us. Is there any way you can build the automations and load these into ActiveCampaign? I had never done that. I had used other tools like Drip and MailChimp and ConvertKit and stuff like that. I’m pretty technically savvy and I wanted to help the client. I was like, sure, yeah, no problem. Not realizing that this was its own skill set and this was like its own thing that people paid for. And I just did it for free. They gave me the login credentials for ActiveCampaign. I went in, I figured out how to use it in a basic way, built the automation to deliver the emails. 

Because of that, once the launch started, I had access to the backend metrics, which I had never really looked at before throughout a launch. And I think this person’s launch list was around 15,000 people. And I was like, Oh man, we are going to crush it. This is going to be awesome. It was a really great offer. And he already had a super successful business. And so I knew that the launch was going to perform well. And I was kind of like, Oh, I’m going to turn this into a case study and I’m going to do all these cool things. And we went through the launch and at the end, the launch did very well for this person. So he was selling an annual membership that was billed monthly. So people were signing up for an annual commitment, but it was split up into 12 payments. And he ended up adding about $20,000 to $21,000 in monthly recurring revenue to his business. So that was like a really solid lift for him. And so I was like, okay, that was great.

But as I was looking at the email metrics, I was like, man, these emails got a 7% open rate or a 10% open rate, 8% open rate, like what is going on here? I had really no idea at that time what the factors were that impacted email performance and placement and deliverability. And so that was the moment where my eyes really opened up into, okay, we did well with this launch, but what if we doubled the open rate? Or what if we got the open rate to 30% or 40%, how much better could we have done? That’s when I started going down the rabbit hole of, What, how do you increase the performance and open rates and click rates and visibility and all of that? And then there was a year-long exploration process there. Then I had a conversation with Brian Kurtz, who you actually have had on this podcast a couple of times.

Rob Marsh: Brian’s an amazing mentor and friend. He’s great.

Matt Brown: I love Brian. Brian has sent me a lot of free stuff over the years. He’s just such a good guy. So this is my moment to pay it back to Brian. Thank you so much, Brian. I was interviewing him for a podcast I was working on at the time. I was kind of doing a pre-interview, information-gathering sort of thing. We just started kind of talking about some of the stuff that I was doing and thinking about and I was talking to him about things like list management and email lists because I knew he had a background in mailing list management and then he just gave me this whole download. I wish I would have recorded it because I now just kind of have to remember it in my memory. 

But he just gave me this whole download about the importance of lists and list management and all of this stuff. And I was like, OK, there’s really something here. So that’s when I shifted my focus to trying to do everything I could to optimize this performance email deliverability. And from there, I took a lot of courses. I’ve talked to a lot of ESP support people, tier two deliverability support people. And there was a time where I’m having more conversations with active campaign deliverability than I am with my own family. It was a lot of learning. And it was around 2022, I think that I developed my own process and I started working with people almost strictly in an email performance optimization capacity.

Rob Marsh: Okay. So as I listened to you talk about looking at the numbers, the metrics and seeing, okay, they’re not that great. Most copywriters would respond, well, let’s try a different headline or, let’s try a different topic or maybe, that idea was wrong, but there’s a whole bunch of stuff before we even get to the copy that impacts deliverability and whether people are opening or not. Let’s go through these almost item by item. And in some ways, I’m almost asking for a 30-minute webinar or podcast-inar about all these things that we need to do to make sure that our emails not just get to the inbox, but get opened.

Matt Brown: Yeah, absolutely. As a copywriter, I tried all of those things, you know, I was like, okay, maybe this subject line isn’t working. And then I would do split tests, and then maybe the preview text wasn’t optimized. And let’s try a trick in the preview text line. And no matter what I tried from a content perspective with the from name, the subject line, the preview text, it never significantly moved the needle. So that’s when I discovered deliverability and placement,. There are levels to a deliverability problem, like a true deliverability problem usually arises when your technical setup is not done correctly. This has only increased this year because of all the new requirements, sender guidelines from Google and Yahoo. But in the past, it was still a problem. 

If you hadn’t properly authenticated your tools to send email on behalf of your domain, then they were just going to go to spam or not be delivered based on your DMARC record and things like that. I never worked with a client that had a true problem like that, that’s such a basic problem. Most of the people I worked with had reputation issues where they were getting a really mixed placement. Some of their emails go to spam, some go to the promotions folder, some go to the inbox. It wasn’t until I learned how to essentially guarantee that a message can go to the inbox or the primary tab of whatever inbox somebody’s working with that those 15% open rates became 30% open rates or the 20% open rates became 40% open rates. 

So to go through a step-by-step checklist or like a deliverability checklist: the first thing is your reputation as a sender. So your reputation as a sender, and I’m primarily working with people who have lists that are almost entirely made up of Gmail and Google Workspace contacts. When we do audits of lists, we typically find that 70 to 80% of all the contacts on the list are using a Google product. So it’s really what we want to optimize for. Google has its own set of criteria that it uses to determine your reputation as a sender and the quality of your domain and things like that. So the first thing I look at is to see how does Google actually rate your domain as a sender? There’s a tool—if you’ve been reading my emails, I’ve talked about it in basically every email. It’s Google Postmaster Tools. And when you install it and where you get it configured with your domain, it will start aggregating these reports about how it views you as a sender. 

So to give you an actual graph-like report of how they rate your domain on any given day, and you can have a high, medium, low, or poor reputation. And so if I started working with a client and they started with a low or medium reputation, I knew that that was immediately an issue and that was going to be significantly impacting placement. So then you have to take steps to improve your domain reputation. Most of that can be done within the email environment itself. But there are some other external factors where Google—it really depends on how you’re using your domain as well, like for your website or how old the domain is. So the goal initially is always to just get the sender reputation as high as possible, because no matter how good your content is, it doesn’t even matter if you’re sending promotional emails or not sales emails. If you have a low reputation, you can’t even get a personal one-to-one style email into the inbox of your subscribers. So that’s the first thing I look at. 

The next thing is the general tool or the tech stack that somebody is using. Your email tool isn’t as important as a lot of people think it is. A lot of people are like, oh, what’s the best? ConvertKit or ActiveCampaign or Klaviyo, Drip, Ontraport. Most of the tools are basically all the same. But they do have unique ways of doing things. And so just like you have a domain reputation, you also have an IP reputation that comes from your ESP. So not only is your domain sending emails, but there actually are IP addresses that are then connected essentially to your domain that you’re authenticating these specific IPs to send email from your domain. And those IPs will have their own reputation as well. 

So the way these email tools work is they put you on a shared IP with hundreds or thousands of other senders. And so it can be entirely possible that you’re on a set of IPs that are being used by people who are spammers or are doing not necessarily nefarious things, but just aren’t properly managing their list, aren’t keeping their list clean and are bringing down the reputation of that IP pool. So if you’re at a high enough volume, Google will start giving you reports about the IPs that you are using as well. So you can go in there and see, okay, I’m on a high, medium, low or poor IP pool. And then you can talk to your ESP, just be like, hey, is there any way that you can put me onto a better pool or upgrade us? And depending on the tool that you’re using, they each kind of have different ways of doing that.

Rob Marsh: Is that something Postmaster Tools from Google, they’ll tell you the IP rating or how do you check that IP reputation?

Matt Brown: They will tell you the IP reputation because it’s checking the IPs for DKIM authorized emails. So as long as your emails have been authenticated, like I know yours are, if you’re sending a high enough volume, and I don’t know what the exact volume limit is, but I think it’s probably somewhere between a thousand to five thousand emails at a time. As long as you pass that value threshold of your daily sends, you’ll start getting reports about that. So that’s something that you can check there. But some tools, they assign the same IPs to everybody and other tools will automatically put you into pools with similar senders, if that makes sense.

Rob Marsh: Yeah, as we’re talking about this tech stuff, I know you said the tool doesn’t matter all that much. Most of these tools, because of the changes that Google made this year, they implemented some systems to make sure that this stuff gets set up in the first place correctly. So you talk about the DKIM or DMARC setups, you almost have to have that in place properly to even use most of the big tools today, right?

Matt Brown: Exactly. There was kind of a major shift where in the past you could allow the email tool to basically manage your deliverability for you. And that’s when you would see something like Rob at thecopyrighterclub.com sent via ontraportmail or some long server name like that. And so it was almost a proxy way of sending email from your domain where they’re letting the inboxes know it’s coming from you, but it’s really not. It’s being sent from Ontraport or ActiveCampaign to Convertkit’s internal system, and you haven’t fully authenticated these tools to send email from your domain. 

That was one of the major shifts of the new guidelines that Google and Yahoo introduced in February, that now you basically have to do that. They do, if you’re below a certain threshold, if you have less than a thousand or five hundred contacts, there are still ways to not do that. But in all of the support documentation, they’re saying we highly recommend getting this set up when in the past it was more optional.

Rob Marsh: You mentioned there are ways to not do it if you’re under 500. But I can’t imagine a reason you would not want to do it if it’s going to impact your deliverability. Eventually, you might as well set it up properly from the start.

Matt Brown: Oh, yeah, you definitely want to do it. I think it’s more like the tools, they just created these safeguards, because they know there’s going to be a certain percentage of the user base that never opens their emails. They have no idea that this is going on. And so they kind of have to create these systems to protect their platform because they don’t want rogue senders just bringing down the reputation of whatever tool that is. For example, Kajabi while you can add your custom domain and authenticate all of that, if you don’t do it, they push you into this way of sending where you’re not actually even sending from your domain. They create an email address for the user. So it would be like Rob at KajabiMail.net. And so they just bypassed that whole thing and created a workaround to protect their platform. That’s how I view it.

Rob Marsh: That makes sense. So what else technically do we need to be thinking about when it comes to sending?

Matt Brown: So I think the design of your email is very important as well. I am not a designer. I’m not good at making things look good. I always create very simple email templates. But if you have a bunch of super design, custom coded blocks in your email or are using emails that are primarily image based… I know that this is something that a lot of e-commerce companies do, where essentially the entire email is one long image, or there could be 10 images that are two megabytes each that have different design elements. And they actually convert the copy  into an image file, which is actually no text in the image or in the email at all. That’s the sort of thing that I would shy away from for sure. But what’s funny is that if your reputation is high enough, you can get away with sending those emails. If your engagement rates tell Google and the other inboxes that even though it’s all images and takes forever to load, people want to receive these emails and they respond to the calls to action. You can still do that, but if you’re having placement issues, I would shy away from using a super graphic, heavily designed email template. And at least start testing a simpler format of sending your emails.

Rob Marsh: Okay, that makes sense. And again, a lot of the ESPs, the email providers… they have ways to set this up so that you don’t necessarily have to create images to send, but you can create the HTML blocks, that kind of stuff. So it really shouldn’t be a problem, but I know sometimes the default is create it all in Photoshop, kick out a PNG or a JPEG or whatever, and you can just load that up and make it happen that way.

Matt Brown: Exactly. And then from there, this is kind of a technical thing, but it’s now leaning a little bit more into the content reputation relationship side of email. is that it’s really important now to keep your spam complaints as low as possible. So previously, it’s always been recommended to keep your spam complaints low. But now it’s basically a hard and fast rule that with Google, you have to keep your spam complaints below 0.3%. So for every 1,000 emails you send, they don’t want to see more than three spam complaints. And as long as you’re doing a good job with your opt-in path and keeping in touch with people and informing people about who you are, how often you’ll be sending them, what sorts of things you’ll be sending them, giving them lots of opportunities to opt in for future communications or opt out. You should see those low, but there are people out there who click the spam button and you’re going to see spam complaints. 

It’s not concerning if you see consistent small spikes, but if you’re sending a high volume of email and you see over 1% spam complaints, then you’re definitely going to run into some trouble. And that’s the sort of thing that’s then going to lower your domain reputation. So it’s almost like this direct correlation if I’m working with the client, and they get a 5% spam complaint one day, I can almost guarantee the next time I pull up the domain reputation, it’s going to go from high to medium and then you kind of have to work your way back from there.

Rob Marsh: Cool. Anything else technical that we need to be really diving into?

Matt Brown: I think maybe the last technical thing is the actual email address that you’re sending from. And it’s not like there’s a hard and fast rule. You must send from a name, like rob at the copywriterclub.com. But you want to be sending from an email address that is also used in some way as a conversational email address. Based on what I’ve seen, Google and the other inboxes, they tend to deprioritize messages from email addresses that only have a one-way communication where it’s like, all right, this email sends out 50,000 emails and it has no one-to-one conversations with anybody else from there. So even if you’re using hello at the copywriter club.com, as long as there’s a support person that’s responding to emails from that email address as well, [that’s okay]. It’s a signal that this is a conversational email address versus just a promotional email address. So that’s another recommendation I have, if you’re going to send emails and if people are going to be replying to that email, use that same email address to send responses versus assigning it to some support ticket software to some other email address or something like that.

Rob Marsh: I think we’ve seen a big change in that. You know, 10 years ago, it used to be really common to get the do not reply address… nobody watches this inbox or whatever. I don’t see those very often. I did see one a week or two ago, and I was actually surprised because it’s been so long since I’d seen one. I was like, oh, somebody sending emails. And I’m guessing that a lot of those are usually used in the delivery of something rather than part of a help box or whatever, but I think that’s something that, setting up… oftentimes we’ll set up a hi or an info at whatever the address is. And then we’ll do most of our correspondence in a more personal box. I think that’s a really good reminder that if you do the two, you’ve got to make sure that you’re playing around in both boxes.

Matt Brown: Absolutely. And a lot of tools too, they give you the option to set two addresses, the from address and the reply to address. So that if you send from Rob, but the reply goes to hi, when somebody actually clicks reply to respond to your email, the way the email is coded, it’s going to override the response to the from address and then go to the hi. And so then the hi at thecopywriterclub.com email address is going to get all the benefit of the conversation. And maybe you set up Rob to appear personal, but in reality, you never actually send anything but marketing emails from that address. So you’re kind of losing the benefit of the reply.

Rob Marsh: Okay, that makes a ton of sense. I want to go back to, I think it was the first thing we started talking about, when we said this technical stuff that we need to watch out for like reputation, obviously is critical. What are the things other than not having the technical stuff set up properly? What are the things that we do with our emails that impact the reputation that we need to be looking out for?

Matt Brown: Yeah, so the biggest thing is engagement. I see people running into reputation problems when they consistently send to disengaged segments of their list for a long period of time. Let’s say that you have 25,000 active subscribers—people who opted in to receive email, and you’ve been mailing them for two years. And over the course of that two years, you have a 20% open rate. If you dig into some of the metrics there and you pull up a report of everybody who’s subscribed, everybody who’s received an email from you over the past 2 years, and then you add a parameter that says, show me someone who hasn’t opened an email in a year or two years or ever. A lot of people would be surprised to see exactly how many people have never opened an email, who haven’t opened an email in six months, nine months, a year. And so what brings down your reputation as a sender, in my experience, is when you have a really large chunk—it doesn’t have to be a majority chunk—but let’s say out of your 25,000 people, you have 10,000 who haven’t opened an email in a year or longer. By consistently sending to those people who aren’t opening, it sends a signal to the inboxes, specifically Google, that people don’t really want to receive the messages from this person. Yes, there is a section of them who are consistently engaging. But if you’re not muting those disengaged contacts or unsubscribing them, that’s going to shift you from inbox to the promotions folder or into spam. The larger that segment gets and the longer you send to those people. So to improve your reputation, you basically have to undo that process where you only send to your most engaged contacts for long enough so that you build up a signal of trust to move back into the inbox.

Rob Marsh: You said long enough, but how long is long enough? I’m guessing it depends. If I’ve blown up my list, I had, let’s say 20,000 people, half of them didn’t open. I still mailed them for two years. Can I fix that in a couple of weeks? Is it going to take me a year?

Matt Brown: Definitely more than couple of weeks. The shortest I’ve ever fixed this process was a month. That was somebody who really didn’t have that big of problems. I was honestly surprised that we were able to get it done as quickly as we did. The longest a project has ever taken me is nine months. I worked with someone last year and we started in May and I was like oh yeah we’ll be done by the end of summer, no big deal, because their list wasn’t that big. But I just didn’t have a real sense of how truly disengaged a big section of the list was. 

The other thing too is that this process is kind of delicate where it’s easy to think, okay, great, we’re back in the inbox, we’re all good to go, let’s mail everybody again—you can undo that work really quickly. So you have to maintain these sorts of really high engagement rates, I like to see, you know, between 35 to 50% true open rates, you have to maintain that long enough, and then be strategic about how you re approach disengaged people to attempt to reactivate them or unsubscribe them. So anywhere between, I’d say two to six months for most people would be long enough. If somebody out there knows a faster way to do it, by all means, please get in touch with me. I’d love to hear what you say, but I’ve done dozens of these projects and that’s typically what I see.

Rob Marsh: Okay, so engagement is really critical for reputation. Anything else?

Matt Brown: The content definitely matters. Once you solve your reputation problem, that’s when content becomes a much bigger factor in where emails go. Once your reputation is high enough, you can basically send whatever you want. I actually have this test that I do at the end of a project where I have a document with every spam phrase you’re not supposed to say in an email from every ESP. It’s just copied in there. It’s only spam phrases. Like, become a Bitcoin millionaire overnight, free pills, all the stuff you’re not supposed to say. And if we can get that message to inbox after a deliverability project, I know my work is done because inboxes are saying, we trust you so much as a sender that we know people want to hear from you, even if it has the most crazy things in this email. 

Now, I never send that email to a live list. I’m only sending that to seed lists for specific deliverability tools. It’s not something that ever goes out there, so it can never damage the reputation, if someone’s worried that that would happen. But when you’re in that middle place, things like subject lines do really matter. Preview text, the length of your email, the number of images you have in there. And so you can get really granular. 

I went through like an obsessive phase where I tested everything about an email multiple times before I sent it. It’s really easy to spend a lot of time over-optimizing or really trying to perfect an email, which is now why I really focus on just getting the reputation as high as possible. Because once that happens, you can worry a lot less about [about things like] is this image size too big? Or is the promotional percentage of this language too much? Or did they not like my link CTA copy? Because you can get messages to place in the primary tab of the inbox by tweaking those things. But it’s a lot of work, and it’s kind of a pain.

Rob Marsh: That makes sense. You mentioned, and this is just my own curiosity, you mentioned the preview text. I didn’t realize how preview text might impact that. Are you saying you should always include preview text or is it just the kinds of words that you’re using in preview text?

Matt Brown: It’s the words that you’re using in preview text. Preview text is definitely secondary to the subject line and the from name and the from address and everything else. But there’ve been weird situations where I didn’t change anything else about an email and you take a word out of the preview text and all of a sudden Google likes the email or you delete the preview text entirely and it likes it or you add an emoji and it likes it. So this is getting into like the crazy making part of optimizing emails, but it does, it is a factor in where an email place is.

Rob Marsh: Okay, and then what about multiple links in content? So for instance, today, we released a podcast, and I will always include a link to our website where you can listen to the podcast online, usually link to the episode on Spotify, I’ll link to the episode in Apple Podcasts, there might be an offer in the PS that there’s a link to. How’s that impacting reputation and maybe not just specifically to me, but any grouping of links like that, or even worse, links that have nothing to do with each other. How does that impact deliverability and reputation?

Matt Brown: Yeah, from what I see, it’s more about the total number of link destinations than it is the number of links that you include. Linking to a podcast episode, for example, and you have three calls to action interspersed throughout the email that are all going to the same place. My opinion is that’s treated as just one link, but then when you have links to a lead magnet and maybe an offer, and then you have your social media links at the bottom… What I see is that the more links destinations that are added in an email, the more likely it is to get a deprioritized placement. But again, f your reputation is high enough and if people engage with these types of emails for a long enough period of time in a meaningful way, you can still get great placement. 

I will say this, my theory right now is that Google is really cracking down on affiliate links in emails because what they don’t like is a bunch of redirects. So If you’re using click tracking in your emails, every link is essentially going to be a redirect where the first link that gets triggered is like the Octoport link or the active campaign link. So they know, this person clicked the link and then it’ll redirect them to Spotify or your website. For example, I did like a breakdown of an email that Tim Ferriss sent and he had like 60 link destinations in one email and the most of them were affiliate links for like Helix Sleep and Athletic Greens. And there are tools that can show you the actual paths that a link takes to arrive at its destination. And that email that I analyzed, it went to spam. And my theory for that one specifically was that Google was testing how to treat emails with a ton of affiliate links, where it goes from ConvertKit to ag1.com slash Tim to click.shareasale.timferrisathletagreens to some other like specific landing page. So there’s like five redirects because that’s actually a technique that spammers use to cloak links and deceive people. So I would definitely test placement before sending out an email with a bunch of affiliate links in them now.

Rob Marsh: I imagine a lot of people are thinking, well, no big deal. I don’t do affiliate deals, but I’m guessing that link shorteners like Bitly, Owly, and whatever may have the same… basically it’s the same process, right? So does that have that kind of impact too?

Matt Brown: It’s not recommended to use Bitly link shorteners in your emails. I haven’t had issues using redirect plugins, like pretty links and things like that, where the the link is going to like the root domain and then it’s just going to a 301 redirect on the same site. I haven’t had those same issues, but yeah, bitly links. I would not recommend using those.

Rob Marsh: As we’re talking about deliverability, obviously this is critical, but also it’s not all that exciting. Maybe a lot of copywriters who want to talk about copy and how do I write great emails, but anything else we should be talking about when it comes to this deliverability? We ghave ot to nail this stuff in order to get it through.

Matt Brown: Well, one, if you are responsible for the performance of emails, I would definitely start tracking and monitoring this stuff. So if you don’t already have Google Postmaster set up, you should just set it up for the domains you manage and for the brands or businesses you work with. And set up a weekly reminder or weekly task to check it. I check it every day because I’m obsessed about it. Because you want to understand what are the factors out there that are going to be impacting my emails? 

As a copywriter, you want as many people as possible to see your messages, to open them, read them, and respond to your calls to action. And then I would also recommend getting into the practice of testing the deliverability of your emails before you send them to the entire list. Once you’re good and in the clear, you don’t have to do this as much. But if you’re having problems, I recommend a tool called Glock Apps. Basically, the way that it works is that you sign up for this tool, you buy test credits. I think they give you three test credits per month. And they then give you a seed list of email addresses from every inbox around the world. So Gmail, Google Workspace, Yahoo, like Yandex, like mail.com, Zoho, every inbox that has a meaningful user base. They’ll create an email address for them. You then load that seed list into your email tool. And you can put it in its own list or tag it so that it’s quarantined from the rest of your contacts. And then you take the message that you want to test and you create a duplicate of it where you insert like a little text snippet, which is how Glock apps identifies that you’re the sender. This is the test credit that’s associated with this. You then send the email only to those seed contacts, and it’ll give you a report of what percentage went to the inbox, tabs, spam, undelivered, and it can be really helpful in identifying mailbox specific issues. Maybe you’re great with Hotmail, but awful with Google. And start, you know, taking steps to improve things from there. 

The thing about seed lists is that these are not real email addresses. So this is just one data point. If you can inbox with all the seed lists, in my eyes, you are golden, because these are basically unmanned email addresses that tools and algorithms and robots are monitoring. And each ESP handles IP assignments differently. So I know, for example, with Ontraport, I actually encountered this issue with Ontraport. They dynamically select the IP address to send an email based on the previous engagement of that contact. So their best IP addresses are reserved for the most responsive contacts and their worst IP addresses are reserved for the least. So a seed list, these are emails that are never really going to open an email or click a link. So they’re always sent an email from the worst possible IP pool. And so you can kind of get a false negative, but can be a really helpful data point in determining where do we stand in general with the inboxes? And then you can work with your ESP if you want to get a slightly more specific or more accurate way to test these. So a lot of them have deliverability tools, like Ontraport uses a tool called Validity to test their own deliverability. So if you ask nice enough, they will sometimes share that information with you about your account.

Rob Marsh: OK, I want to change what we’re talking about here just a little bit. Obviously, we’re still talking about email, but as we listen to your story and how you became an expert in this stuff, a lot of people who are listening are probably thinking, OK, clearly there is a valuable skill set here that our clients need. And in fact, I’m guessing that a lot of the stuff that you’ve been sharing here, most clients have never thought of, maybe don’t even know it’s even out there other than the fact that, man, my open rates are terrible. And so let’s assume I’m a copywriter who has been writing emails, or maybe I want to write emails as one of my packages, the services that I offer to my clients. How do I add expertise in deliverability? What do I need to do to pick up these skills? How do I approach a client as far as, hey, I can take over your deliverability, your ESP management. What does that conversation look like?

Matt Brown: Yeah, this is a great question. And this is really when I started getting a lot of traction with the freelance side of my business and working with clients was that I realized, there’s a lot of copywriters out there who hate the tech. Like I was in a bunch of groups and I was like, I hate the tech.

Rob Marsh: I don’t want to do the automation. I only want to send a Google Doc.

Matt Brown: Yeah, exactly. I just want to write. I was like, Oh, I like the tech. I really enjoy it. I think it’s just as interesting as writing copy. And once I started talking to my clients about that, it basically went from like, we’re considering you among other copywriters to like, how soon can you start? Like, oh, you can do the tech, like you can handle both sides of this? They were like, yes, let’s do this. And when you can basically guarantee that your messages will perform well, it’s very attractive to clients, especially most of the people I’ve worked with, they have a smaller team or a team of VAs who are capable of following directions, but can’t do the strategy. 

And there’s this void where there’s nobody really managing this very important aspect of their business because they have no interest in learning it. They don’t have the knowledge. And then the people on their team, they just want to do their job and do what they’re told versus make these sort of more meaningful changes. So for a copywriter who wants to add this in, especially if you’re already working with emails, I would recommend first, picking one or two email tools to really just go all in on. If most of your clients work with Klaviyo, become a Klaviyo expert. Just like take all of the free courses that Klaviyo puts out by Klaviyo education courses, and really learn how that platform works so that you can start using it in the best possible way. If it’s ActiveCampaign or ConvertKit, just pick a couple of the ESP tools that you know your clients use and master them. 

Then deliverability is kind of weird because there are a lot of documents out there on each ESP’s website about how to improve deliverability—deliverability best practices—but they’re very vague and they can be very technical. And there’s this void between what the ESPs educate you on, what the inboxes are willing to educate you on in terms of deliverability. So you really have to learn from somebody who has mastered this process. 

I’ve bought a lot of deliverability courses, some of them good, some of them not so good. One that I would highly recommend, I don’t have my own course, but I would highly recommend a course from Chris Orzakowski, who you’ve had on your podcast. He’s got a course called Double Your Deliverability. I paid, I don’t know what the current price is, but I think I paid 200 bucks for it. I’ve paid a lot more than that for deliverability courses and I learned the most from this one. It was very helpful and you can go through it in a weekend. So that would be a good place to start. And then really just start testing and get a sense of how your emails are currently performing and then do some of the things that we’ve talked about in this podcast to work towards improving them. You can also subscribe to my newsletter where I’ll share all of my tips about how to do this.

Rob Marsh: I can’t remember if this was something that you shared in your newsletter, but there’s this idea that has been kicking around the back of my head, and that is that old email addresses, as they get retired or people move on from an employer or whatever… sometimes Google will pick some of those up and use them as trap emails in order to test sendability. Is that something you’ve talked about or am I conflating that?

Matt Brown: I think I did two editions about that. I talked about robots, spam bot accounts. And then I did another email about spam traps and honeypots.

Rob Marsh: Yeah. Talk about that. Why is that important to know about?

Matt Brown: II always get these two terms mixed in my head. So if you’re a super technical person and I get this mixed up, you can email me and I’ll make it up to you. But I believe that what happens with honeypots is that anyone can sign up for a Gmail account today, five years ago, 10 years ago. And they recently went through a notification process which was basically: if you haven’t logged into your Gmail account, we’re going to be deleting it. We’re taking it over. It’s no longer yours. If you want to keep an old address, log in and claim it as yours again, basically. And all the inboxes do this. 

But what they do with some of the accounts is that they don’t actually delete the email addresses. Like if I owned Matt Brown 99 at Google.com. they’ll leave it active and then they’ll convert it into what’s called a honeypot. It’s still a hundred percent deliverable address… like a list cleaning tool, like emailable or Unbounce, they could pick it up, but your ESP will still be able to successfully deliver an email to this account. So it doesn’t appear like a dead email address. And so what the inboxes use that for then is to find all of the people who are probably spammers. What spammers do is they just scrape the internet for any email address. They try every possible combination of names and numbers and things. They just send emails with the hopes of getting their crazy message into somebody’s inbox. And so if you aren’t regularly cleaning your lists based on engagement and time, it’s possible that you have an email address or a couple of email addresses on your list that you can successfully send to, but that are no longer consumer addresses that are owned by the inboxes to find spammers. So if you get one of those hits, it’s like a spam trap or honeypot hit, that can bring down your reputation as a sender and put you into sort of a purgatory zone where you’ll need to take steps to rectify that. It’s very hard to find those accounts just within your ESP, which is why you need a third party tool like Emailable or Clean13 to do it.

Rob Marsh: So yeah, that’s an argument for cleaning your list. Not just checking to see who’s opening your emails and doing that, but actually doing a clean of your entire list where they identify known traps, known honeypots, all of that, and then give you that report that says, okay, these ones definitely take off your list right now. These are a little risky, whatever, and this part of your list is clean, and keep emailing them forever.

Matt Brown: Exactly. Yeah, that stuff’s valuable. 

Rob Marsh: Okay. I think that’s maybe enough about technical stuff. Let’s talk about email copywriting because again, you’re a copywriter and this is where you started. Obviously, a lot of copywriters are adding or want to do email as part of their services. In fact, my guess is that email is at this point the most in-demand copy deliverable out there. You can create a website, but websites are good for three to 10 years. You can create a sales page, but other than rewriting them occasionally, those are good for several years. But email, some businesses need emails every single day or at least every single week. So what are some best approaches to… what have you learned as far as writing emails for clients?

Matt Brown: So the broad strokes for how I approach email, and I actually learned this from another one of your guests, RySchwartz. I think early on when I was learning from him, his goal is to never be boring. And that’s kind of my approach as well. Never send out an email that could bore somebody. And you don’t have to be flashy and over the top and have a really well-defined sense of humor. But as long as you can write emails and send content out that you know your audience is going to find interesting and engaging and entertaining. I find that whenever I write emails and send those out, they tend to perform very well, not only from an open rate standpoint and a click standpoint, but through sales and conversion rates for different calls to action as well. 

And so I use a ton of copywriting frameworks and they’re just deeply ingrained in my brain at this point. But I really like to center emails around problems, urgent problems. I like to try to make those problems as real as possible in the mind of the person that’s reading the email and then connect that to promises and way better desired outcomes. Kind of set a scene and paint a really captivating picture and make it fun for someone to read an email. I think one of the first courses I ever took on copywriting was John Carlton’s course. And he was like, make your copy the most interesting thing the person is going to read that day. And while I’m nowhere near as entertaining a writer as John, I’ve always kind of kept that in the back of my head, too. Just try to make this the best thing this person’s going to read and that’s going to be specific to them. And yeah, that’s certainly worked well up to this point. Obviously you want to make it extremely readable and to create a very seamless, smooth experience for the person to consume the content. Telling stories, you know, it’s all in there.

Rob Marsh: Yeah, I’ve actually started collecting examples of emails, the different approaches that people have. Obviously, story emails are great, but very few emails that I get are actually just story. There are conversation emails where people are reflecting a conversation, teaching emails, so many different ways to approach it. And I think that idea of never being boring is good. Coupled with an always be useful frame, I think maybe helps with that. So, you don’t have to tell a story. If you’re giving me your email, oftentimes they give me something that’s like, oh, wait, I need to go check that because it’s going to impact this part of my business. So being useful, I think, is maybe the counterpunch to be entertaining.

Matt Brown: Absolutely, yeah. I think actually it takes a lot of bravery and courage to just purely tell a story in an email. It’s incredibly difficult to tell an entire story or part of a story in general. There’s a lot that goes into it in terms of aconflict and the different tensions that are keeping the story together. And from my experience, whenever I try to write a story email, it’s very easy to just fall into narration, where it ends up just going very long, and I’m kind of losing the point. 

So I applaud people who are just excellent storytellers in emails, and it is always something that I’m trying to improve in my writing as well. I think that might be one of the reasons why you don’t see too many of them. It’s easy to open with the story and then lead into a solution or a broader, useful piece of information. But like Tarzan is really great at telling stories. I mean, she did a launch a couple years ago. I think it was just one story the entire time. And I just had to tip my hat and give her a round of applause because we’re like, dang, you had the guts to do that.

Rob Marsh: Yeah, Tarzan, I think, is a really good illustration, too, of getting vulnerable in her emails, which helps create that personal relationship with a lot of her readers, especially if you connect with where she is in life, with the situations that she goes through. Sso vulnerability, I guess, would be another way to make sure that your emails connect.

Matt Brown: Totally. But like useful vulnerability, too, where it’s not just like cracking open the pages of your journal. It’s both captivating and like you said, useful to the person that’s reading it.

Rob Marsh: What else do we need to be thinking about when it comes to high-performing emails?

Matt Brown: It’s funny you mentioned the relationship because that’s really what it comes down to. Ultimately, you want to get to a point where people are opening your emails because you’re the one that’s sending it, not because of the time they got it or the subject line or the preview text. If through each touchpoint you have with a reader on your list, if you can start building that resonance and that connection to you as a sender so that they actively look forward to receiving your emails, you can honestly forget about everything else we’ve talked about in this email. 

I have clients who have “the Oprah status” in their industry where they’re just so beloved and known and people seek them out. They’ll find their emails in the spam folders that everything is broken with their systems, but they still get a 60% open rate and make tons of sales because they have done the actual hard work of building their authority, telling their story, becoming known, and building that relationship with their readers. So yeah, that would probably be my biggest piece of advice. 

And also, if you have a deliverability problem, it’s a great problem to have because it is incredibly fixable. So if after this, you go start testing your emails and everything looks awful, don’t worry. There is a systematic way you can get back from that. It is very solvable. It is much harder to completely dial in your messaging and your offer and your relationship to your audience. So if you’re already doing a good job at that, you are miles ahead of everybody else.

Rob Marsh: And how to do that I think would probably be an entirely different podcast or maybe a whole course.

Matt Brown: An entirely different podcast, exactly. You have to go back and listen to every episode you’ve ever recorded and then piece it all together and then combine it with everything else you’ve ever learned in your life. That’s the big thing. Exactly.

Rob Marsh: Okay. So what should I have asked you about when it comes to emails, deliverability, marketing, and getting all the things right, creating high-performance emails that I haven’t asked you just because my expertise isn’t deep enough to know what else I should be asking?

Matt Brown: That’s a great question. I feel like you did a really good job of asking me about all the things that I’ve been kind of blabbering on this entire time. So I feel like I’ve covered a lot. I think one thing that a lot of my clients ask me kind of privately, like, okay, Matt, how do we beat Google? Or how do we trick Google? And you can’t. Google is not going to be tricked, you should not be trying to trick Google. If you see little fads out there about how to do this or that, they will only work for a very short amount of time. And it’s possible that you could be penalized long term because of them. So I would suggest learning to work with Google and the inboxes. They’re not your enemy. 45% to 50% of all emails sent on a daily basis are spam. So they have an impossible job of filtering out the good from the bad. And as long as you learn what they’re after and can then build your strategy around that. You’ll have no problems in the future.

Rob Marsh: Okay, so before we started recording, I mentioned to you that I’ve heard a bunch of people mention your name. Chanti Zak, I think is somebody who’s used you. There’s a few others. You’re kind of becoming, or maybe you are, the email deliverability expert to a lot of the stars in my universe. If somebody’s been listening and they’re thinking, I need to learn from Matt or I need to be on the email so that I’m as up to speed as I possibly can be, where should they go? How do they connect with you and continue to learn from you?

Matt Brown: Absolutely. So the best place to go is deliverabilitynow.com. It’s just a simple landing page, but you can opt in for my newsletter there. That’s how we got connected, Rob, actually. I think Chanti recommended my newsletter in her newsletter, I saw your name pop up. And I’m like, No way, this is not THE Rob, is it?

Rob Marsh: It may not be THE Rob, but it is A Rob.

Matt Brown: It’s A Rob. So you can sign up there, I send out a weekly email. And for new subscribers, I actually have a catch up email  where I kind of send out some of the greatest hits of my recent newsletters. I talked all about the new rules from Google, I talked about Spamtraps and honeypots and Google Postmaster Tools and email design and testing and all of that. So yeah, that’d be the best place to learn from me. 

I actually love partnering with copywriters on projects. So some of my best clients have come from my copywriter friends pulling me into saying, hey Matt, we’ve got problems. Can you help us out? And it’s great because they get to write the emails and I get to fix all of the technical stuff. So if you’re working with a client or you have clients that have some potential issues, you can shoot me an email and I offer free deliverability audits for people so you can pop in and take a look at things and then you can be the hero to your client because you found the solution to the problems.

Rob Marsh: I’m guessing there’s a huge need for that across the board. Because like we said, there are people who are not paying attention to this stuff. They know they need better emails. They hire a copywriter. The copywriter writes an email, but it’s not the content of the email that’s the problem. It’s not even necessarily the offer. It’s this deliverability stuff. And so if you’re a copywriter and you’re seeing that stuff, it might make sense to call Matt and get him on your team. And like we talked about earlier, maybe you start adding these skills to your own skill set so you can fix them, learn from Matt so that you can do it yourself.

Matt Brown: Absolutely, it’s a great skill to have. If you touch email in your job, you should know a little bit about this, at least so that you can advise your clients and understand if you have a deeper issue, because you can often double the performance of your emails without changing anything about the content. 

Rob Marsh: That’s a headline right there. Double the performance of your emails is a great promise and something that a lot of my clients would love. So thanks, Matt, for spelling it all out. And you know I’m on your list. I pay attention to what you say. So thanks for sharing so much with our audience.

Matt Brown: Of course. Thank you so much for having me, Rob. Really appreciate it.

Rob Marsh: That’s the end of our interview with Matt Brown. Maybe you’ll do what I did as soon as you stopped listening, and that is go to check your Google Postmaster tools, or if you don’t have them set up, get them set up so that you can check them once the data comes in. You can get a ton of information there, spam reports, sender reputation, IP reputation, and a bunch of other metrics that can be useful to keep an eye on. I was pleasantly surprised that our reputation looks pretty good. 

Now I want to go back to the idea that Matt shared during the interview that he got from Ry Schwartz, who said that his key to good emails actually is a key to good copy: never be boring. It’s good advice. I see a lot of boring emails. And like I said, it’s good advice, not just for emails, but for copy sales pages, whatever it is that you’re writing. Never be boring, but also be useful. It’s not enough to be entertaining. At the end of the day, you’re building trust, you’re showing that you know what you’re talking about, you’re building your authority, and most importantly, you’re helping to solve problems. But writing an email that is the most interesting thing that your readers will see today, that’s a high hurdle. And if that’s the standard that you use, you may struggle to come up with ideas that you want to share. It’ll be easy to dismiss almost everything that you come up with for being not entertaining enough. So if you’re struggling with that, if you’re struggling to be entertaining or interesting, reframe this idea by looking for the least boring thing that happened to you today. That’s something that our friend Kennedy from email heroes teaches. You don’t have to be interesting. You don’t have to be entertaining. You just have to be not boring. And usually the least boring thing that happened to you today or this week qualifies as that. 

Let’s emphasize right now that the most important part of deliverability is the relationship that you build with your readers. If you’re sharing interesting, useful ideas and insights, that’s a good start, but you can do more. Re-listen to our interview with Daniel Throssell from a couple of weeks ago and learn from his world-building and dialogue creation ideas and strategies. These less obvious ways of engaging readers help them look forward to what you share in your emails, whether that’s every day or once a week or whatever the pattern is you have for sharing your thoughts and ideas with your readers. You want readers to see your name in their inbox and open your emails, even if they don’t read the subject line, even if they have no idea what’s in the email, because they know that no matter what, you’re going to teach them something or help them solve a problem, or you’re going to reframe an idea in a new way, or you’re going to entertain them. And yes, sometimes you’re even going to pitch them with offers that are going to help them and you want them excited to get that pitch. 

Now, if you’re on our list, I hope that we clear that benchmark for at least part of the time or some of the emails that show up in your inbox. And by the way, if you’re not on our list, you can join that list by visiting thecopywriterclub.com. Just scroll down that homepage. There’s a form there, or you can do the quiz on the homepage, or you can click the form at the bottom of any of our blog posts or podcast transcript pages. We would love to have you on our list. And if you are on our list, let us know what you think about what we send to you. 

I want to thank Matt again for joining us to talk about email and deliverability and even how to add this to your service offerings if that sounds interesting to you. I think there is a big untapped market of clients who are willing to work with copywriters or actually wanting to work with copywriters. long-term if they know that they can help them improve their deliverability, help them increase their sales by getting more emails into the inbox. And you can find Matt at deliverabilitynow.com. Go get on his email and start learning this stuff directly from him. He is a master. He knows what he’s talking about. 

That’s the end of this episode of the Copywriter Club podcast. If you enjoyed this interview, Please share it with a friend or an associate who might also enjoy it or learn from it.