Building a Personalized Email Newsletter That Works for You with Brennan Dunn

Joe Casabona: A few weeks ago we talked to Louis Nicolls about the importance of having a good newsletter that helps people — something targeted, an educational resource. Brennan Dunn knows a thing or two about that and has built an empire around segmentation and personalization. The last time he was on the show, we talked about RightMessage. Today, we talk to him about email templates and newsletter strategies that we can implement with his new tool, Palladio.

I’m really excited for you to hear this conversation with Brennan where he equates emails to sales pages, where he talks about how to run sales in the middle of sequences and creating evergreen newsletters. It’s going to be great and I know you’re going to learn a ton, especially if you, like me, are trying to grow your newsletter.

In Build Something More, we talk about how he built Palladio, the virtues of a minimum viable product, and email client issues. If you are interested in hearing an ad-free extended version of this in every episode of How I Built It, you can head on over to joincreatorcrew.com.

This episode is brought to you by LearnDash and WP Wallet. You’ll hear about them later in the show. But for now, let’s get on to the intro and then the interview.

[00:01:28] <music>

Intro: Hey everybody, and welcome to How I Built It, the podcast that helps small business owners create engaging content that drives sales. Each week I talk about how you can build good content faster to increase revenue and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

[00:01:52] <podcast begin>

Joe Casabona: All right, I am here with Brennan Dunn. He is the founder of Create & Sell, RightMessage, Palladio, and a bunch of other things. He’s a busy guy. I don’t know how he does it all because I know that he also has some number of children. I think they might be a little older than mine. Actually, that might not even be true. Let’s bring Brennan in and then we can talk about it. Brennan, how are you today?

Brennan Dunn: I’m good. How are you, Joe?

Joe Casabona: I’m great.

Brennan Dunn: For the record, I’ve got two older kids 10 and 13, and then a one-year-old.

Joe Casabona: Okay. Okay. Most of yours are older than most of mine. But I have a four-month-old at home. Awesome.

Well, thanks so much for coming back on the show. I think I had you on a couple of years ago, post-CaboPress talking about RightMessage and segmentation, personalization. I’m glad I’m having you on now because I finally did all of them. I cleaned up my ConvertKit account, I got rid of so many unnecessary tags. I’m trying to use custom fields more. I’m not using them quite… You’re a master at this. Maybe we could talk about that.

But I have like four segments and I have email sequences for specific segments. And I’m excited to finally be focusing my efforts on that. And that was all thanks in part to you and that first CaboPress I went to where we talked about the need for… I signed up for ConvertKit that day that Chris talked about-

Brennan Dunn: Oh, nice.

Joe Casabona: …and then I started getting into more of the segmentation stuff.

Brennan Dunn: Awesome.

Joe Casabona: So the listeners, if I did my intro right, I’m breaking the fourth wall. If I did my intro right, I’ve already kind of talked a little bit about you. So they know we’re gonna talk about Palladio today, which is a super awesome tool. I signed up the day you launched it, which I’m now very grateful for it because I think it’s switched to a subscription model. Is that right?

Brennan Dunn: It’s going proper SaaS.

Joe Casabona: So proper SaaS.

Brennan Dunn: You got the LTD.

Joe Casabona: Yes.

Brennan Dunn: You got the lifetime deal.

Joe Casabona: One of the only lifetime deals I actually use. So maybe we can start off with what is Palladio? I’ll try to say it with my Italian, right? The Palladio.

Brennan Dunn: Palladio.

Joe Casabona: What is it? And maybe how did you come up with the name?

Brennan Dunn: Sure. So what Palladio is, is imagine Webflow but for email. So it’s just an easy way to visually create not only email templates. So we think of email templates as being the shell, like a WordPress template, like the thing around the content, but it’s also a tool for creating and using widgets which are kind of like, I mean, to get WordPress—I know a lot of your listeners use WordPress—it would be like adding Gutenberg elements or something like that, that are a little more than just rich text.

So you think of most email content as being headings, italic text, bold text, images, and that’s kind of it. Palladio allows you to create really anything you want that you can then add directly in line to your emails.

Joe Casabona: That’s pretty important, right? Because ConvertKit, they switched to a more block editor recently. But there’s still this kind of weird handshake you need to do with their widgets/snippets/reusable areas. And unless you’re really adept at HTML and Liquid, which is my weak point, and I guess understand how email clients work, all of those things have to converge for you to do this properly on your own. And Palladio kind of handles all of that for you.

Brennan Dunn: Yeah. That was the goal. I mean, it started out… Let me answer the name thing and then I’ll tell you about the origins. So back at university, I studied kind of the classics. So we did a lot of stuff with the Greeks and Romans and everything else. We kind of made our way through Western civilization.

One of the people we focused on was Andrea Palladio who was the Renaissance architect in Italy who kind of brought architecture into the modern age. So that’s kind of the parallel here is this is the way to kind of bring email to the Renaissance, if you will, of email designs. So I just picked the name for that reason.

Joe Casabona: That’s fantastic. I love that. I mean, as an Italian American I absolutely love that. I’m going to look up Andrea Palladio. Quick side quest. I think you also got me into some of the Stoics reading, right? I was reading the Ryan Holiday book.

Brennan Dunn: All right. Yeah. We read and translated Epictetus, Seneca, Aurelius, and stuff like that in college, too. I haven’t read actually Ryan stuff, but I know he does a good job of kind of, I don’t know, packaging it up for modern world.

Joe Casabona: Right. It’s like a primer, right? But you’re the one who kind of encouraged me to read the source material. And after that, I read “Meditations.” And I have Seneca’s on deck. I have a personal retreat coming up and so I have Seneca on deck for that.

Brennan Dunn: Hopefully Ryan is a little less… Again, I haven’t read his stuff but I know [inaudible 00:07:36] he talks about basically things like if your child dies or something, just realized that’s-

Joe Casabona: Yeah.

Brennan Dunn: A little brutal first for the modern-

Joe Casabona: Yeah. It’s funny because he does mention that. And I’m like, “You have kids now, Ryan.” But I guess that’s if you’re fully embracing the philosophy. Maybe we can talk about that more in Build Something More.

Which, by the way, I didn’t mention the episode number nor do I have it handy here. But the show notes you’ll be able to find over at streamlined.fm/267. There it is. I bounced back. So everything that we talked about here and you can sign up for the Creator crew, where you’ll be able to get ad-free extended episodes of this podcast where Brennan I will talk about a bunch of other stuff, maybe how he built Palladio and the Stoics and stuff like that.

So instead of jumping into the how for this episode, let’s talk about the why. Maybe we alluded to it earlier but what encouraged you to do this?

Brennan Dunn: For the longest time, I was very dyed in the wool with kind of the way I think a lot of us when we got started with email marketing thought, which is plain emails are best because they look more like from a real person, right? Like I wouldn’t send you a personal email that would have like grids. I would send you something that was like, “Hey, Joe…” newline and stuff like that.

So that was my initial thinking. And then I started to do… The real petri dish for me was Double Your Freelancing, which was kind of the company that I led to everything I’m doing now. Which with that the big kind of takeaway there… I forget where I heard this, but somebody said something like, There’s a reason we don’t generally write sales pages in Google Docs.

And I know many of us might start that way. But when it comes to things like consumption and people skimming, especially sales email and longer emails and stuff like that, structure is a big thing. And it’s good to have clear divisions between thematic sections.

What I started to see was that people would use creative uses of headings and emojis to do this. Like they’d break apart or break up different sections of their emails with different emoji, headings, and things like that. But what I wanted to do was I wanted to find a way to easily using the tools already used, because obviously, Amazon and like Ecommerce companies do a lot with graphical and designed emails. I mean, they’ve been doing that for ages.

But I wanted to find a way that I could do something like that where I could, you know, starting with like call to action areas, and things that I really want to stand out. Where before I was doing the little emoji pointer thing with then the URL “click here” in bold. Which, obviously I’m not saying that doesn’t work, but I wanted to find a way to make it so… I could make the emails be a little more digestible, if that makes sense.

Joe Casabona: Yeah, absolutely.

Brennan Dunn: So yeah, that’s kind of what led me down. I don’t do generally the kind of crazy design emails personally. But I like having a bit of structure, especially nowadays where you find a lot of creators will have like, Oh, this newsletter is sponsored this week by a company. You want to have a nice, elegant way of showing a little call out for that sponsor. And then you want to have a referral area or a social share area, or something like that.

Obviously, you could do it with just rich text and stuff like that but I find… Again, I wouldn’t say I’ve done this scientifically by any means. But personally I find it a little easier to look at a testimonial, for instance, that is set aside with the photo of the person and the quote they said, and whatever else rather than just a paragraph of italic text. That’s like Joe’s testimonial or something.

Joe Casabona: That lends a little bit more credibility to testimonials too. That’s what they say on landing pages, right? Don’t just have the text. Have a picture of the person if you can, and make it stand out.

Brennan Dunn: And that’s the thing. I mean, sales pages are meant to convert people, right? They’re meant to get people to buy. Again, I know a lot of people will kind of scrap away, set up initial sales page maybe in Google Docs, but eventually, we tend to design it. We tend to make it a little more structured and laid out.

Joe Casabona: Right, yeah. And you know, kind of the headlines because people are going to skim, so catch their attention, you know, break things up with images, have those trust-building sections like the logos and… It’s funny that you’ve mentioned sales pages a couple of times. Because I think there’s also probably… just like it’s simpler emails versus kind of more designed emails, there’s also like, how often should you sell to your email list? What’s the dance of providing value versus selling?

I had Samar Owais on a while ago, I think now earlier in the year for sure, and she said, you know, don’t sell in the very first email but you can kind of subtly mention your offers throughout, and then you can have a full sale sequence. What’s your kind of approach to selling to your list? I’m on a couple of your newsletters and I don’t feel it’s heavy-handed. So it feels good to me.

Brennan Dunn: I don’t do the usual way I think. Not the usual but the way I see a lot of people doing things is kind of the model of purely educational emails for a while and then you kind of shut down the list and do a big launch every once in a while, or a big promotion of something. That’s going back many years.

I mean, that’s what people like [inaudible 00:14:05] has done. I forgot the name of the guy. I think it’s Joe Walker, the Product Launch Formula guy. That kind of model of like you do the educational, educational, educational to build up the trust and kind of create indebtedness to all the good stuff they’ve given you or you’ve given them, and then you kind of cash out with a big launch.

My preferred way, and this is all to get back to Palladio, another reason I built Palladio is to leverage segmentation, personalization to make it so I can do interesting things like, well, what do I know about Joe? Well, he’s told me he uses ConvertKit, he told me he’s at the stage of his business, so on and so forth. Oh, he hasn’t bought Mastering ConvertKit so at the end of today’s newsletter, he’s going to happen to see a call to action or an ad, if you will, for that product design. Whereas somebody who uses, say, Active Campaign would not obviously see my ConvertKit course.

So I’m more of the model of I want to just show up every week and write a newsletter, write original content, and then let the call to action that brings the money in be dynamically generated based off of who’s getting the email, what I know about them, and also what have they bought or haven’t bought. So that’s kind of the dynamic.

I started calling it a dynamic, yes, way back when, but it’s kind of evolved into something where even now with Create & Sell I’m doing things where I’m mixing that model with my referral program. So if you refer people to my list, you get store credit, and then it also recommends a product. So if you’ve sent like 10 people to my list, you get $5 referral. You’ll see the price of the product I’m recommending to you discounted by $50 based off of your referrals.

So that’s my model. I much prefer just doing list-wide kind of blasts, if you will, of original content each week, and then letting the call to actions be dynamically placed.

Joe Casabona: That’s really interesting. So is this a mix of your other products, I don’t know, your main product-

Brennan Dunn: RightMessage?

Joe Casabona: RightMessage.

Brennan Dunn: Yeah.

Joe Casabona: …and these templates?

Brennan Dunn: Kind of. I’m using RightMessage as a way on my opt-in pages or post-opt-in pages to segment people, usually along like who are they and what are they looking for at the moment. So in my case, it’s stuff like, why did you join Create & Sell?” “Well, I’m struggling with building an audience.” “Cool.” “What do you use?” “I use ConvertKit.” “Awesome.” “How comfortable are you with ConvertKit?”

So I get into that kind of questions but I’m using RightMessage for that. And then all that gets fed into their subscriber record. So the benefit there is I’m getting about 83% of all people who join going through that survey, which means I’m starting with more than just, you know, “This is Joe, and this is his email address.” I’m getting a bunch of other good info too that I can use to drive that engine.

So that initial seeding is done with RightMessage, but everything else is 100% ConvertKit, where I am using a lot of Liquid which I’m using, frankly, Palladio to do. Because Palladio is not only kind of a visual template builder. It’s also a tool that includes a bunch of widgets but also does stuff like Liquid writing for you. Like it’s still outputs Liquid for ConvertKit or whatever. But it lets you create that liquid in a way that doesn’t make you write Liquid code.

That’s what I’m doing is I’m using internal data. So I’m obviously already tracking what people bought and haven’t bought within ConvertKit. And then it becomes a matter of just using a bunch of Liquid to say, “Cool, here’s everything Joe’s eligible for, but he’s bought this, he’s bought that, we’re not gonna pitch Palladio to him because he owns it. That’d be dumb. So we’re gonna pitch the other stuff to him.” And yeah, it tends to work really well.

[00:18:13] <music>

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[00:19:20] <music>

Joe Casabona: Let’s talk a quick philosophical question here because I know tags are what a lot of people use. I use them mostly because it’s easier for me to implement, right, even as a programmer. I just haven’t taken the time to set up the right automations to use custom fields. But I know you are a big proponent of custom fields. Or at least you were. Is that still the case?

Brennan Dunn: It’s always the case.

Joe Casabona: So maybe you can tell us just like a 10,000-foot overview why a custom field is better? Can you do the same kind of stuff with tags? One of the reasons I use tags is because they’re a little bit more exposed with the ConvertKit API. So like automations are a little bit easier. Tagging is more easily automatable, I believe, than custom fields in certain cases.

Brennan Dunn: Yeah. So I’ll get on my soapbox for a second.

Joe Casabona: Yes.

Brennan Dunn: Functionally they’re identical. You can trigger automations by custom field changes. You can do all that kind of stuff. Some of the drawbacks there were integrations with ConvertKit often will only write tags, not fields. So you’re kind of screwed there.

But the main reason that I tend to prefer custom fields is that often a lot of what I’m using… So it all boils down to segmentation. Like we want to know this about this contact. Let’s say you have a segmentation data point, like what is somebody’s number one problem. That could change. That could change from over the relationship of them being on your list.

The issue with tags is that let’s say… to keep it easy, let’s just ditch the number one problem, let’s talk about favorite colors. So what’s Joe’s favorite color? And typically, people would say, “Well, I’m gonna have a red tag, green tag, a blue tag, whatever.” The big issue is that if you are tagged red, meaning red is your favorite color, if that needs to change in the future, you end up needing to write clean up automations that will say, “when green is applied, go and remove red if it exists and remove blue if it exists, and then leave them with green.”

Tags cleanup automatically. You know, to go back to the programmer idea, you would never have a SQL database that has a bunch of “is blank fields.” You would instead generally have some sort of state data about, I don’t know, plan, plan type. You’d have a field called plan type and the options would be like basic, silver, bronze, gold, whatever. Typically, that’s how we model data.

So it’s the same thing where custom fields automatically clean up. Let’s say, I want to track somebody’s email service provider. The ones I’m tracking, I have another option. But I also track up to 10 different main things, like ConvertKit, Drip, ActiveCampaign, HubSpot, and so on. That would mean I’d have 11 tags floating around, where instead I have one custom field. So it ends up being a lot cleaner.

Again, let’s say they don’t use an email service provider, and then a month after my list, they click on my ConvertKit affiliate link and now they use ConvertKit and now I want to start pitching them all my ConvertKit stuff. If I wanted to tag them as ConvertKit, I would need to go and remove the “doesn’t use anything” tag. Because otherwise if I want to send a dedicated email to somebody and I target people who are tagged “don’t use anything,” well, what if they also have the tag ConvertKit? Like, which one is it? So it lends itself to ambiguity.

Joe Casabona: Yeah, you need to create either segments or right in the email like, “is tagged with don’t use anything, and also not tagged with Convert Kit.”

Brennan Dunn: With anything else. So then it just doesn’t scale well at all.

Joe Casabona: I mean, from another kind of information gathering standpoint here, I think maybe a classic example you’ve used is membership. You can tag somebody as a member. And when they churn out, you can remove that tag. Or you can have a custom field that’s like current member or member plan if you offer multiple plans, or you can tag them as not a member or custom fields can be not a member. Or it can be churned. Right?

Brennan Dunn: Yeah.

Joe Casabona: Again, that’s less clean up because if you have member, not a member, churned, it’s only going to be one of those things. Right?

Brennan Dunn: Yeah. I mean, the quintessential example there would be let’s say you have a membership site, and a trial period, and then they’re an active customer. Say you’re using tags to drive all this, and then they cancel, so you have trial applied, you need to then have logic that would say, “when they move to active, remove trial if it exists. And then likewise, when they go from active to cancelled, remove active, apply cancelled.”

But then the big issue is let’s say they cancel and they go back to sign up again like a few months down the road. Unless you have the logic in place that says when they go to sign up, also remove canceled if it exists, which you’re probably gonna forget to do that, then say you send a dedicated email campaign to everyone who’s canceled. Well, that person might start getting emails from you saying, “Hey, come back.” And they’re like, “I am back.”

Joe Casabona: “I am back.” Yeah.

Brennan Dunn: I mean for things like where you shouldn’t truly have multiple states at once, that’s where custom fields come into play. And you generally don’t want multiple states at once should you want to do any sort of personalization. Because typically speaking, if I want to track what is Joe’s number one priority at the minute, I don’t want multiple answers. I want a single focus that I can then personalize the content that you get.

Joe Casabona: That’s a great way to put it. Custom fields are kind of like a one-to-one relationship. At any point the custom field should represent one state tags. I’m using again tags for my multiple newsletters. Maybe somebody wants my podcasting newsletter and my creator toolkits newsletter.

Brennan Dunn: That’s perfectly valid use case work.

Joe Casabona: Awesome. I’m glad we went down that road because I think it’s really important. Again, I was stuck in this until very recently. I was just kind of sending people one weekly personal newsletter as Louis Nicholls put it on his episode, right?

And those kinds of personal newsletters are a hard sell for anybody who doesn’t know you personally. So I did like the reinitiate welcome email. Like, “Hey, a lot has changed around here. I’m offering a few different things. Click on the statement that you think works best for you. And then I want emails about podcasts. I want emails about site building, or I want it all.” And then if they hadn’t clicked it was kind of based on what form they signed up for.

Again, that’s been working really well for me. But the personalization and the segmentation really… if you want to grow your newsletter, which I think you should, I think that’s really important.

Brennan Dunn: Yeah. Great.

Joe Casabona: Awesome. So we kind of mentioned, right, it used to be conventional wisdom to send simpler emails, because they looked like they were from real people. That said, I feel like another common thing people are doing with these emails is sending like one sentence as paragraph and then having like 20 paragraphs. It feels like a very panicked way to write and read. I don’t think you do this. Yours are very long-form writing, if I recall correctly.

Brennan Dunn: No, definitely. I mean, I’ll sometimes have a short paragraph. I’m not doing Victorian-era style, you know, half page, long paragraphs. That’s a digestibility thing. Because I do think, to your point, I mean, it’s easier for me as a reader to digest short bits than… And you find this a lot on the internet marketing side of things, I think, where they’ll have these very… Yeah. You know what I mean?

Joe Casabona: You walk into a store. Period. New line. You see the shelves are empty. Period. New line.

Brennan Dunn: And all that’s for is for digestibility, right?

Joe Casabona: Yeah.

Brennan Dunn: I mean, it definitely has its place, and I think it works. But I tried to do more straight up… I’m not as baity I think with the content that I try to send. So I wanted to just be almost more of like a slow burn. Like, if you’re legitimately getting value from me each and every week, then my expectation is at one point you’ll probably buy something, and then hopefully you’ll buy more. And that’s kind of my MO with this stuff.

Joe Casabona: Yeah, awesome. I love that. I really like that—if you’re getting value from me. Again, one of the things that I’ve kind of gleaned from you because I saw this section in your newsletter and I was curious about it was the referral section. I’m using SparkLoop. You’re using SparkLoop. I’ve explicitly paid for Convert Kit Pro just for the SparkLoop integration. It just financially makes sense that way. And then I also get the benefit of being able to fix links that are broken later.

So you talk about, you know, if you’re getting value for me it’s a little bit more of a slow burn. How important do you think referrals are to this whole strategy? And then secondarily, I guess, how important is it to make the referral section stand out? Maybe that’s like a softball for you. Because you could just have like “Refer this.” Right? It could be just text. But you’ve put time and effort into making a couple of different referral widgets that I think really stand up.

Brennan Dunn: Well, that’s me… Again, I mentioned a second ago I try to do baby things. This is absolutely where I do baby things. The widget in question that you’re referring to is kind of this leaderboard style. Not even a leaderboard. There’s no competition. But it’s more of a gamified progress bar. You’re this far away from the next year thing.

And quite a few people have picked it up. Probably the biggest being James Clear. What’s cool about it is I wanted to have something that would be a bit more than what you were implying of like the simple plain texting. I wanted to have a proper area at the footer of an email that would then be able to show somebody like, “Here’s what you’re tracking toward next.” And that’s where Liquid comes into play because that’ll be personalized based on what tier they’re on.

I read a few weeks back an email about this to my list about… I don’t know, if when you were in middle school or elementary you did that magazine sale thing, where you’d get these thresholds you’d hit of like when you sell this much, you get this toy or something. And you sell a bit more and you get another toy. And that’s kind of how I’ve always seen the SparkLoop model of these different tiers that you track toward.

So I wanted a way where instead of just saying you’ve done zero, three, or two, or three, or whatever, I wanted to have a more horizontal version of those vertical ones at elementary schools I’ll ever have of like, “This is how big we’re getting to the top. And once we hit there, we get the new play set or something on the playground.”

So I wanted something like that because I knew it would work, I knew it would be visually a lot more effective. It absolutely has proven true because people keep using it and they’re ditching what they have been doing for that. I mean, that’s what I wanted. And then that’s where it started.

But then there’s also a lot of other interesting ways that I’ve found to leverage SparkLoop. One of the more recent ones has been… you know the “click to tweet” stuff you see on blog posts all the time?

Joe Casabona: Mm.

Brennan Dunn: Well, I wanted to build an equivalent of that. That you could embed as a widget in an email. And the benefit would be it would automatically include your SparkLoop referral link in it. So you could say like, “click to tweet” inline in the middle of an email. They click that, it tweet it out, and they’re getting attributed for anyone who clicks through on that thing you just tweeted.

That’s less of a general “share my newsletter” and more of a “share this interesting concept I just shared from this part of the newsletter.” And yeah, it’s just a lot of fun ways that you can do stuff like that. But yeah, I absolutely think SparkLoop has been instrumental for me. On a good month, I’m getting about 11%, 12% of all new referrals-

Joe Casabona: Oh, wow.

Brennan Dunn: …or all new opt-ins from SparkLoop. I mean, there are people who do much better than I do. I think one thing I haven’t touched yet that I want to at some point would be like giveaways and more intentional campaigns. Mine have always just been kind of passive things, the footer of every newsletter a little thing. Although, with Create & Sell I’ve actually retired my famous wish thing in favor of that referral or recommended product edge I mentioned.

Joe Casabona: Yeah, I noticed that. And I’m really glad you mentioned that because I wasn’t sure if you were recommending Convert Kit.

Brennan Dunn: It’s a test. I don’t know. I actually don’t know. The big picture thing, which I hinted at is you’ve referred people on my list, there are no more tiers. There’s no more like, “send 10 people and get this prize.” Instead, it’s “for every person you send, you’ll get this much credit.” And then “here’s the recommended product for you with your credit applied if you have it.” So kind of bakes in all of it into one.

But I haven’t done like the ditched in that case, the progress bar in favor of the big recommended thing within text under about how to get credit. It’s stuff like, “Hey, if you have a podcast, let’s all go on it and we can include your link basically. We haven’t talked about this, but we probably should.

Joe Casabona: I definitely will.

Brennan Dunn: Exactly, yeah. But things like that. “If you liked this article, here’s the permalink for it. Go ahead and share this in your next newsletter” since most people on my list are creators and they have their own newsletters. I’ve been using that and favor the thing that most people who buy Palladio for, to be honest. But it’s a test. I don’t have enough data to know if I’m going to keep doing it.

Joe Casabona: It feels good, though, right? Because it’s very concrete and consistent. My rewards right now are like, I don’t know, like a free eBook, and then free membership for a year and then a consulting call with me.

And if nobody cares about the eBook or the membership and they just want to get the consulting call, now it kind of feels like a slog to have to get to that many. Whereas, like, if I say, “Hey, you’re gonna get credit to Joe Casabona Inc. and you can use it for the membership or you can keep saving and get a free consulting call with me, that’s fine too.” And then you can have that vertical bar like you’d have in-

Brennan Dunn: Everyone likes discounts too.

Joe Casabona: Yeah, right.

Brennan Dunn: So you would say like, “Here’s Joe’s… you know, some product for yours that you’ve got. And if it’s regularly like $100, you could say, like, “It’s $70 for you because you’ve sent me six people,” or whatever the value is for a referral.

Joe Casabona: And that’s the other thing. You are assigning a value to each email address and then you’re kind of forced to think about… Because this was the first thing I did the onboarding call with SparkLoop, and they were like, “Well, how much is each subscriber worth to you? That’s how you should determine your rewards.” And I’m like, “I have no freaking idea. I don’t know.”

Brennan Dunn: Yeah, exactly.

Joe Casabona: So I had to think about that. Like how much is a subscriber worth.

Brennan Dunn: It’s one of those things where, you know, I’m making less money, but the question is always, “Would I have gotten that sale if they weren’t incentivized with a discount, because their referrals that they’ve made, whether it be intentional or not? And, you know, I got more people on my list.

SparkLoop does a good job at doing kind of antifraud stuff. But I’ve absolutely seen a few people who have blasted it out to their telegram group. None of the people who have joined are the kind of people that should be on my list, but they’re real people. I just kind of let it slide. But yeah, I mean, that’s the other big thing too.

It’s not like you can cash out. I think when I was talking publicly on Twitter about doing this, people are like, “Oh, well, can it be abused?” I’m like, “Well, it can really only be abused if potentially somebody gets stuck by stuff for free, or alternatively at a big discount. And the fact is, I’m selling digital products, so my margin is like 97%.” So if they get it for 40% off, I’m still okay at the end of the day. It’s not like physical inventory or something. Right?

Joe Casabona: Yeah. I mean, that really is the affiliate model, right? I mean, up until recently, ConvertKit was giving you like 30% of every dollar that they made off somebody you’ve referred. Honestly, I was vocal about that on Twitter. I try not to piss and moan on Twitter as much anymore as I did in my younger days.

But that one really got me because it was a very sudden change that could have a big effect on creator’s bottom lines. I think after six months your job is now done, right? You’ve got people onto the platform. And if they stick around for six months, now they like the product.

But for a while I was like, I mean, they must be just making money because everybody I refer is now… maybe they’re referring other people or they are… It felt like an interesting model because they were losing 30% off the top of everybody I was referring. That felt like a big cut. Awesome.

Well, this has been a great conversation. The last thing I want to ask you about is not really related to designs or referral sections. Which by the way, again, at the show notes at streamlined.fm/267, these will be affiliate links to Brennan’s Create & Sell newsletter. I think it’s really good. I strongly recommend it. I’ve learned a ton. As well as SparkLoop because I’m using that now and I’m approaching my list building for that.

This next question is kind of based on that. Evergreen versus kind of one off segmented emails. I have a new newsletter called Podcast Tips at getpodcast.tips. This is an evergreen newsletter that I’m using SparkLoop primarily with. I don’t know if you can set up different campaigns in SparkLoop. A cursory turned up empty for me because I’m only using it with this one newsletter because it’s a very targeted, “Hey, do you want to send more podcast tips to people?” But it’s also evergreen, right? So when people get referred, they get pushed to the top of the stack.

What’s your opinion on kind of evergreen versus one-off? Is there a feature in ConvertKit I’m missing where like I can pause the evergreen segment to insert a more timely email or anything like that?

Brennan Dunn: Yes, you can. This is something I’ve been doing for myself for a while only because… I call it a shadow newsletter. It’s the same thing. But the idea is that for a lot of us what we’re sending doesn’t change. We’re not sending like-

Joe Casabona: We’re not like Morning Brew.

Brennan Dunn: …stock market stuff where it change every day. This is stuff that’s pretty evergreen. I mean, my thinking is that the problem I have with live newsletters… And again, Create & Sell is still live newsletter whereas Double Your Freelancing is not a live newsletter. It’s a shadow newsletter at this point.

But the biggest show I have as a consumer have a live newsletter is the same issue I have with blogs, where when you go to like a typical blog you see it by date ordering. Like the most recent article, then from there on, the other stuff. Whereas if I’m somewhere new and I want to learn from a brand or a company or a person, my thinking is I want something a bit more curated. And with an evergreen or shadow newsletter, you can do that.

You can say, “Well, here’s three months’ worth or a year’s worth of content that I’ve written.” And it makes sense to order it in a certain way, rather than just kind of the usual newsletter thing of like whatever I happen to write this week and send it out is what you get, regardless of how long you’ve been on the list, regardless of how familiar you are with what I talk about, so on.

So I really like evergreen for that. I find it to be a better user experience. You can combine it with things like the upfront segmentation we talked about. Case in point, one of the things I ask is, how experienced are you with email marketing? Well, if somebody’s really experienced, maybe it makes sense for them to skip some preliminary stuff that other people might get.

And these things other people like, it could look like a weekly newsletter, right? Like I can change the ordering, if you will and say like, “You get on this track if this is your need. You get on that track if this is your need.” And then once you’ve exhausted these tracks, you go to a generic track or general track. And then you just go from there.

Because you can still do all the stuff I talked about with dynamic call to action and your referral area and stuff. Like the end-user doesn’t know or care potentially that you didn’t write that this morning and hit send. As long as the content is what they need at that point, awesome.

So I’m a huge fan. That’s actually how, when I started RightMessage, I was able to step away from Double Your Freelancing. Because Double Your Freelancing did… You know it has a 52-week evergreen newsletter. That’s a year.

So the benefit there is somebody can go join the list today. And I don’t need to show at all and they’re getting weekly newsletters for me every week for a whole year. The benefit there was I could do that and go and start RightMessage and focus on that while having minimal impact to sales because all that stuff kept happening on the Double Your Freelancing side of things.

And to quickly answer your question about the technical thing of like, what if I have like an urgent… not urgent. Like, I want to send this out to everyone-

Joe Casabona: Timely thing.

Brennan Dunn: Well, you could either do the easy thing which is just send two newsletters that week or one live and they’ll get the evergreen, which is more content from Joe, maybe not a bad thing. Or the more complex thing would be ConvertKit sequences will not send emails to somebody’s already received by default. So you could technically do a bulk operation that would remove everyone from your sequence, that is the evergreen newsletter-

Joe Casabona: Got you.

Brennan Dunn: … and send your broadcast and then after that put them all back in that and they’ll filter down to where they left off or where they were before. And that’s typically the traditional way of doing something like that. Because that makes sense.

I mean, I’ve always thought… For instance, one of the things I talked about a few weeks ago on my newsletter was having a kill switch where it can be as simple as just I don’t… Let’s say you send out every Saturday on your evergreen newsletter, and this Saturday happens to be Christmas day. Maybe you just want to skip a week, right?

Joe Casabona: Right.

Brennan Dunn: So you could do that. You could use this to do that. Because your automation doesn’t know. The problem with automation is it only looks at relative date intervals. It doesn’t know that Ukraine just got invaded today or that it’s Christmas day or something like that. So that’s why I’m a big proponent of having systems that can say like, “Shut it down” type thing and having that easily done.

Joe Casabona: You know, it’s funny I got flack for sending an email on Thanksgiving Day. And someone was like, “I just don’t like to be disturbed on Thanksgiving Day.” And I’m like, “I’m not disturbing you. I didn’t send you a push notification.”

Brennan Dunn: Right.

Joe Casabona: “You checked your email app.”

Brennan Dunn: They’re sneaking away from the kitchen table to see who’s emailing them. I mean, that’s me to be honest nowadays with Black Friday starting not on Black Friday. Everyone should be used to that anyway.

Joe Casabona: Yeah, exactly.

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Joe Casabona: I like how you call it a shadow newsletter. So you know, more people want something more creative, having a kill switch. It’s also funny that you mentioned the typical blog thing because I just, on one of my websites, pinned or made a bunch of posts sticky. Usually, it’s one that’s the important one. I made like five sticky because I’m like, “These are the five most important topics I want people to see on this blog.” Everything else is to keep the content machine going for Google or whatever.

Brennan Dunn: Yeah, to feed Google. Exactly. Again, the way I look at it or the way I think about it often is if your weekly newsletter is kind of like a rushing river, if somebody just joins today, you throw them in headfirst. Let’s say you’re doing a series. Like this is the second email of a three-part series you’re sending. If they just jump in at that point, it’s gonna be a bit confusing.

That’s why I really like having something that before you get to… Say this week is a really technical kind of geeky thing, might be the wrong email to start with for somebody. And obviously, you probably have onboarding emails and so on. And this would just be an extension of that.

So you would have your welcome emails, and so on and so forth. You could even have like early on pitch. But then you can segue them into a shadow newsletter. And then you can just go from there and just keep appending to that. I always find it easy.

What I try to optimize for is how little can I log into ConvertKit? Because the more you’re not logging into ConvertKit, the more you can be heads down building your products, focusing on acquisition, or going on a cruise. But at the end of the day, no recipient, unless you’re sending like temporal Bitcoin update emails or something. If you’re teaching people marketing, it doesn’t change that frequently.

Joe Casabona: Yeah, right. That’s exactly right. I have a recurring reminder in Todoist every four weeks to add more emails to that sequence. I’ve got like I think three months leeway. I don’t want to get too far behind, especially for the very first people who joined.

But you’re right. You know, you look at ConvertKit, and again, ConvertKit Pro is 790 bucks a year. And coming from the WordPress space, people will say, “Well, that’s really expensive.” But first of all, I can justify that cost just from the sales I got on my Black Friday sale, right?

Brennan Dunn: Yeah.

Joe Casabona: ConvertKit helped me make more than that. So they paid for themselves. So but like you said, if I don’t have to log into ConvertKit to do things, now they’re justifying their value by giving me hours back. So if I’m charging 200 bucks an hour, well, now they’ve justified themselves in less than a day.

Brennan Dunn: Yeah. I think the big thing that might be a good way to kind of close out this theme would be, I think oftentimes when people think about automation, so that’s what we’re talking about here, is it being something that’s better for us, the market or the creator, whatever, it allows us to go sit on the beach and not do stuff. But we often don’t think about the recipient.

Automation done well means that you can say, Well, what do I know about this person? I know this, this, and this.” What would make sense to send them first? Then what should they get next? And then what should they get promoted at this point? And so on.

Which is better than like, the live broadcast model of like, Oh, Joe’s calendar happens to say that this week he’s doing a big list wide pitch, but I just joined yesterday. Now I just joined this list. I was eager to join, I’m gonna learn a bunch of new stuff and all this guy’s doing is trying to sell me stuff. I think there’s something to be said about automation done right can be a lot more tasteful than the live schedule lead or calendar lead way of doing things is.

Joe Casabona: That’s such a great point. You want to use your newsletter to build trust. And if someone signs up and then the first email they get is “I’m having this big time limited sale,” that does the opposite. Right?

Brennan Dunn: Exactly. But that’s that kind of shotgun approach of hoping to just blast out to the list and hope you’re gonna piss off new people who might not be ready to buy, but hopefully you’re gonna have sales that you won’t care at the end of the day.

Joe Casabona: Right, right. I think, like you said, the next step for me, something that sounds like you’re already doing is segmenting this podcast list further to be like in that first email, “Hey, where are you on your podcast journey?” And then dropping them into the appropriate segment. So if they’re starting, have a sequence of emails for tips for starting. But if they already have one, those people can skip those 10 or 12 emails and just get right into the “I want more downloads,” or “I want to get my first sponsor.”

Brennan Dunn: Exactly. Exactly. Which makes perfect sense. Like you should be sending more relevant content to people and live newsletters make that hard.

Joe Casabona: Right. Again, just to wrap this up, my live newsletter is my personal newsletter. Again, like we said earlier, people who know me are interested. This is the content I made in the past week. These are some of the things I’m trying. And here’s kind of the stuff I’m working on for my membership for this week if you want to sign up. But by and large, I mean, especially the last 50 or so people who’ve signed up for my list don’t know me. They signed up from a tweet I sent. So I want to provide a ton of value for them.

Brennan Dunn: Yeah. And the benefit, too, is when you really go down the rabbit hole you can be doing automated pitches that are based more on when you joined or when you kind of did certain actions that indicated a lot of interest. And then the benefit for you as a creator is you’re used to like no sales, spike in sales, no sales, spike in sales. Right? But even though that’s really fun, it’s nice knowing you make a lot of money in a week, I like more steady stuff, which this allows for.

Joe Casabona: Yes. As somebody with steady bills, I would like something more steady as well.

Brennan Dunn: Especially if the net result is more, because they’re getting pitched when they’re ready to be pitched rather than on your schedule. It means more net sales which we all pick.

Joe Casabona: Right. That’s the other thing. If you’re doing a flash sale, or whatever, and someone signs up for my membership or buys my course because this is the best price they’re gonna get it at but they’re not ready to take it yet, well, now they’ve wasted their money. Right?

Brennan Dunn: Yeah.

Joe Casabona: Now, they’re probably not going to buy my cohort-based course because they didn’t get value from the last thing they bought from me.

Brennan Dunn: Right. Right. And that’s exactly it. And we all know how important it is to, you know, when somebody gets something recommended at the right time they buy it. And then if they’re successful with it, the likelihood of them going on to buy more and to tell people about what you’ve got and kind of that whole thing is just so much more likely to happen.

Joe Casabona: Win for everybody. It’s a win for everybody there. Awesome. Brennan, this has been great. I mean, you shared a lot with us, but it is now a seven-year habit almost of me asking my favorite question, which is, do you have any trade secrets for us?

Brennan Dunn: Trade secrets. I don’t have anything that secret and that I’m not ardently public about it on social media. But I think the big thing is I wouldn’t call it a secret as much as an advantage. And that is started out in software development, went into marketing, and applying all the stuff that us coders do all the time to say emails or sales pages can be super effective.

So yeah, just being able to do things like saying, “Show this case study excerpt in a pitch email if Joe uses WordPress. But if he uses Ghost, maybe show that other thing.” And that kind of stuff, which is kind of the things that we all do naturally. Like if I’m at a conference and I’m talking to you and I find out this about you, I’m absolutely changing. If you asked me about my business, I’ll describe it differently to you that I would maybe somebody else. That’s the stuff that I think it’s just a little code that allows it to happen. And it can go pretty far.

Joe Casabona: That’s awesome. Because you usually hear the opposite. Like programmers are bad at marketing. Coders are bad at marketing. But we don’t have to be. We can take the way we think and apply it to marketing in a very effective way.

Brennan Dunn: Exactly.

Joe Casabona: Brennan this has been such a great conversation. If people want to learn more about you, where can they find you?

Brennan Dunn: The best place would probably be createandsell.co. I do have as of actually today at Palladio.dev opt-in which eventually will turn into a proper marketing site for the product. But in Create & Sell, my weekly newsletter, and I’ll talk a lot about email and everything we talked about. It’s probably the best place. I’m also on Twitter @BrennanDunn.

Joe Casabona: Awesome. You can find links to everything that we talked about as well as a way to get ad-free extended episodes. Brennan and I will talk for a few minutes in Build Something More about how he built Palladio. You can find all of that at streamlined.fm/267. Full disclosure, the Create & Sell link in the show-

Brennan Dunn: I was going to say, don’t use the vocal thing. Go to the permalink for the episode and click that link.

Joe Casabona: Yeah. That will be a referral link that will get me some money off of… Eventually, I’ll buy Mastering ConvertKit as I’m like, Yes, I want to do more. So that will help me greatly if you do that. And then there’ll be links to the SparkLoop and a bunch of other stuff we talked about. But that’s it for this episode of How I Built It. Brennan, thanks so much for joining us today.

Brennan Dunn: Yeah, thanks for having me, Joe.

Joe Casabona: And thank you for listening. Thanks to our sponsors. Until next time, get out there and build something.