Today, I’m talking to Brennan Dunn, the founder of Palladio, co-founder of RightMessage, and general email expert. As a newsletter author myself, I took to this opportunity to learn as much as possible about personalizing and optimizing my email strategy. You’ll also hear what most people get wrong in email marketing. Here’s Brennan.
Arvid Kahl
Hello everyone and welcome to The Bootstrapped Founder. Today, I’m talking to Brennan Dunn, the founder of Palladio, co founder of RightMessage and a general email expert. Now, as a newsletter author myself, I took this opportunity to learn as much as possible about personalizing and optimizing my email strategy by talking to Brennan today. You’ll also hear what most people get wrong in email marketing. Here’s Brennan. I have a burning question for you that why is it that I can tell a generated AI platform like Midjourney or something to Paint Me a Picture that rivals the quality of the old masters within seconds. But when I tried to design an email, even after putting in days of effort and work, it looks like I just opened the website from the 90s. Why is it so hard to make emails look nice? What’s the problem there?
Brennan Dunn
I think it is so, why? It depends on the email client. Let’s put it this way. The issue is that some email clients like Apple Mail use WebKit under the hood. So if you’re basically uses what Safari is and there’s no issue. You can make it through and whatever cool CSS you want and it works fine. And then you have some clients like Outlook and Gmail, which are honestly stuck in the 90s and don’t have Flexbox. They don’t have the concept of box shadows or whatever. I mean, Gmail can’t even load web fonts, including Google fonts. And then you find issues like, yeah, and then there’s things like Gmail. If there’s one issue with your CSS and an issue could be something like you’re using RGBA instead of Hex for color. It discards the entire style for that element, all the styles for that element, which then so basically, the issue is that we as people who are helping people create email templates need to go common denominator to make it. You know, we need to come up with like, what is the thing that will work for the majority of most email clients and that means coding for late 90s era, you know, browsers basically. So imagine being here in 2022 having these modern web browsers and needing to think we want people to architect, you know, this way, but it needs to compile down HTML that is compatible with like, you know, Netscape Navigator for like 1997 or something. So that’s the big issue is that it’s the email client vendors honestly, that are holding us back.
Arvid Kahl
Do you think this will ever change that there will ever be this kind of depreciation of let’s just do something like start with a new standard here? Or is it always gonna be an issue with email in particular?
Brennan Dunn
Well, I mean, there’s a few things, right? There’s the fact of like, email once sent is eventually static. Email can’t execute JavaScript. There’s stuff that’s kind of existing. But again, it’s not universal. And people like the dynamic content, the extent of it is honestly putting an animated GIF that on a server somewhere like a countdown timer you see. That’s not like JavaScript, that’s a server serving an image. And if you I guess it depends on the provider. But if you let it sit long enough, I don’t think they make if it’s like a 24 hour countdown timer. I don’t think the servers are turning 24 hours worth of animated GIF, right? Like it’ll last for some time. But basically, yeah, emails really primitive is what I’m getting at. It’s, you know, there’s no built in mechanism for handling opens or clicks or anything like that. Instead, us marketers had to come up with hacks of like putting a hidden image in it to figure out if somebody’s opened your email. And that hidden image is just basically hitting a server that says, you know, this unique ID happened to load this image, which is how email platforms track and open. So it’s like, when you compare it to things like a Twitter post or a Facebook post or whatever else, it is so super primitive. But it’s universal. It’s not beholden to any new platforms. And unlike with Twitter and Facebook and all that stuff, I can personalize these emails because they’re all effectively individual entities, right? Like the email I sent to you versus the email sent to Justin are two separate generated beings that have no relation to each other. So assuming you’ve got an email platform that’s processing these emails being sent, you can do kind of cool stuff and, you know, make these emails a little more dynamic based on who’s receiving it. So yeah, email
Arvid Kahl
I just wonder how
Brennan Dunn
I love it and I hate it.
Arvid Kahl
Yeah, you chose a business like an ancient technology to build something new on top of, right? To invent on that thing. And that feels like that is quite a thing to make a choice for, right? Because you know that you’re gonna be in this, the HTML, late 90s HTML for quite a while. And not only that, like you’re building a tool with Palladio, right? You’re building something that is sitting on top of other platforms. So you’re building something that is built on an open standard that has to be backwards compatible into the 90s on ESP platform, stead may also inject weird stuff to try and fix it. And I’m using a product and it’s really nice, like my newsletter looks good because of you, right? And still, I sometimes see like the kind of incongruence between what we want it to look like and watch the I would call it maybe the implementation of the day with the ESP, the provider themselves. What all of this thrown into one results in and that feels like wow, this must be hard to deal with. So how is it to partner with these much bigger fish, these bigger platforms and dealing with their own process to have your product have as much impact as possible on your customers?
Brennan Dunn
So partner’s a funny word. I haven’t actually partnered with anyone. Obviously, Palladio works with ConvertKit. But it doesn’t officially work with ConvertKit. It is hard because let’s just talk about email lifecycle. So totally Palladio, which, like you mentioned is the email template builder thing that I created. It creates HTML plus CSS templates that you can load into a tool like ConvertKit. And like you said, when you’re authoring an email in ConvertKit, you’re basically filling in the inner bit of that template with stuff. And ConvertKit creates its own markup, its own CSS and it injects it into your template. This can have unintended consequences, as you know, we know happens. But it is difficult because like you said, I’m battling both Gmail, Outlook, all these weird, you know, inconsistencies about how inbound emails are processed along with ensuring that the final result because ConvertKit in this case sends the final stitch together beginning to end email message making sure it all works with that and like Palladio creates, allows for creation of dynamic content, which means it’s actually also authoring Liquid code, which is what ConvertKit used for dynamic content. So it’s creating a combination of HTML plus Liquid plus the required CSS. And doing a lot of weird stuff in the process like needing to inline CSS because a lot of email clients don’t do well with broad CSS definitions. So you need to basically inline everything, which is tricky because if you inline it and bake it into, say, the email template and then you create content in ConvertKit and an email. Well, that content being created in ConvertKit doesn’t have that inline stuff because it’s a separate beast, right? So yeah, it’s a, sometimes I question why I did it.
Arvid Kahl
Well, one thing that immediately comes to my mind here is the question, have you then ever thought about just building a ConvertKit competitor? Because it feels like you know, you have this abstraction in there. And you don’t have to answer any of these questions if you don’t want to. But, you know, if you are already looking to struggling with these kind of additional platform requirements and limitations, did the thought ever cross your mind to just like do it yourself?
Brennan Dunn
Yeah, I’ve actually specked out. There’s a GitHub repo I have open that specs out in my mind, the ideal ESP and what it would look like and how it function where I won’t get too technical. But basically, the idea is, it’s basically you have a bunch of JSON blobs that represent each subscriber that has whatever data you wanna stick on them. And then you have the ability largely through a DSL to code automations that could be loops and so on. Basically, the ability to have like, think of it as like, think of a framer like Ruby on Rails or Laravel where you have like, Model View Controller. Model is the subscribers. Views are the templates and stuff. And controllers are how you, like I wanna have a coding framework that generates and powers automation, but I use it like I would building a SaaS or something, right? That would be my ideal. I don’t think that’s more of competitive ConvertKit, it’s more like a platform. And then you need something that kind of runs it and sets up all the like automated jobs and job queues and all that kind of stuff. But it’s, I don’t have the time to even look into that. I bought without how I’d love to use it. But yeah
Arvid Kahl
I remember I have plenty of those documents myself with really cool ideas
Brennan Dunn
Yeah
Arvid Kahl
Really fleshed out and no time to do it. But I love the idea of like thinking of who your customer would be. That’s like a person that understands like how to glue these things together and then offer that maybe as a service, or offer that like as an agency for somebody else. Like you have all these layers potentially that this kind of service could do. That’s cool. I like the idea. But let’s not dream too much here. Let’s just talk about the reality of things because I wanted to talk to you about email. Obviously, that’s the thing you’re really good at. And the service that you have at Palladio, I think is really nice because it makes certain things that you want as a creator today, just easier. And one of the things that I definitely don’t wanna do is spent a lot of time authoring an email beyond the thing that I actually wanna tell people, right? I don’t wanna deal with the layout. I don’t wanna deal with like all these little knobs and sliders in those ESP platforms that I have. And ConvertKit is great that you can very much write it yourself. But there’s still a lot of settings and configuration and stuff. And I don’t wanna do that. So that having a tool like yours to make this like a template, select, done, that’s wonderful. And I think particularly now that we have so many ESP platforms around that have all these different things. Creators can get caught up in the process of administrating not the process of creating, but you know administrating this. What is your stance on this? Where is this development going?
Brennan Dunn
Yeah. I mean, I think like you said, I really like structured content, meaning I really like the one thing I built it from day one with Palladio was the idea of having content slots rather than just the generic. You have wrapping stuff that wraps an email and stuff in that email is completely arbitrary, right? Because what a lot of people would do is say they wanna have like a digest email. They’ll go into ConvertKit. And they’ll have like, a heading and then they’ll put like things I’m looking at this week, and then they’ll put bullet points or something. And then they’ll have another heading with like, people I think you should follow and so on and so forth. And my issue with that is there’s static content, which is gonna stay the same, right? And then you have the dynamic content, which will change from email to email. And what I wanted in Palladio was the ability to do kind of like if you’ve ever used with WordPress advanced custom fields or any of these different things where you can say like, I wanna have like, here’s the sales page and I’m gonna define the heading and define the subheading. I’m gonna define the offer, the call to action button, the call to action button label and all these different things. And then you’re just filling in these variables. And then that just fits within a shell. And that’s what I tried to do with Palladio is to allow people to easily and it ends up creating a lot of weird Liquid to make this work. But to allow people to easily set up these placeholders, these meta variables within email campaigns, which at a minimum is just the email content itself. But it could be something as simple as like, hey, if I define a sponsor in a structured way under my logo, I wanna put this week where sponsored by sponsor name or something, which, yeah, you could do that through like weird copying and pasting of like, previous emails or something. But I wanted a nice structured like thinking as a developer, how would I do this if I was building like a web page? I would do it through variables and stuff like that. So yeah, so that’s what I wanted to do. And that’s largely what went into how I built Palladio.
Arvid Kahl
That’s how I use it too. Like for every episode or every issue that I send out, I have this little, you know, watch this on YouTube or just listen to the podcast version of this because that’s kind of how I approach my newsletter. It’s kind of one version of the content that I create every week. The other one is an article and newsletter or the podcast episode, both on YouTube and on transistor as a audio podcast. And I link all of them in the issue, a couple lines into the actual story that I start telling. And I have a little widget in there, right? That has predefined design as it should because why would I wanna do this every time by myself. And what I really do is just copy a couple of not even full URLs because the URLs themselves that go into this, they stay mostly the same, right? Any transistor share link starts with share dot transistor dot FM, so I just copy the little data part, paste it in there and it takes me like three copy and paste just of that data. And all of a sudden the thing works, right? That’s kind of how I would like to approach email more because I don’t wanna type it out. I don’t wanna make sure and that’s the thing like you can spot any automated email from miles away just from the fonts difference between the custom content and the pre configured content because people just copy and paste from whatever kind of document. They have your name and whatever website they’re looking at from, which is hilarious because they immediately that sorts them into spam for me, like mentally.
Brennan Dunn
Exactly
Arvid Kahl
These people didn’t care.
Brennan Dunn
Yeah and they don’t know how to use paste to match style. But anyway, yeah.
Arvid Kahl
That’s such an easy solution to this, right? But then there’s potentially data loss. So if you paste only as text you have the links are gone and all that stuff. So it feels like this shouldn’t be approached from the, you know, from the interface side. This should be approached from the structural side to begin with. This should not be an issue because you solve it before it becomes an issue. I really, really like that. And I think with personalization is another thing in this case that this enables, right? And you are with RightMessage and stuff. You’re big in that field. I wanna talk to you about that because I don’t use personalization at all. And I think I’m really, really missing out here. I know you have a newsletter. And I create and sell, right? And that is a, that’s a great newsletter and I think you’re personalizing it. Can you tell me more about that? Like what parts of the newsletter are personalized? Or what parts are done dynamic? I’m really excited to learn from you how you use this particular feature.
Brennan Dunn
Okay. Yeah. So let me explain kind of my thinking around email personalization. So email personalization, largely, unfortunately, thanks to tooling is quite difficult because to do it right, you know, what a lot of people think they’re doing with personalization is sticking like somebody’s name at the top of the email. And that’s really just variable injection, right? It’s saying, hey, first name, right? Yeah. But I think email personalization done right would be imagine you have a sales email. And then the second paragraph is an example of a customer success story. It would be showing a customer who’s like the person on the receiving end. So if somebody is a designer, they’re seeing a designer story. They’re developer, they see developer story. Like that in my mind is personalization, right? It’s basically thinking, how do I take a core message and postprocess it to make the example shown, maybe the language shown a little more relevant to somebody? So my thinking around this is that, again, to do it right, it requires a lot of if else conditional Liquid code, which is ugly to look at and brittle to write and test. I am working on ways to make that easier. Not there yet. But the end result is that somebody is getting an email where the content of that email is bespoke and highly relevant to them, right? So makes them more likely to read the full email. It makes them more likely to click on the Buy Now button at the bottom or whatever else. So my thinking here is, there’s a lot of effort that goes into it. So I wanna use personalization only in emails that really move the needle. So for me, that would be sales campaigns, that would be onboarding emails that are highly important because you want your onboarding emails to show somebody that they’re at the right place. So my usual way of doing this is post opt in instead of showing a confirmation page. I show a quick multiple choice survey where that data, as the answer just piped up to their new record in my ConvertKit account. So like with create and sell you opt in, I asked you things like what email platform you use. One of them being done. If they choose none, what’s holding you back? If they choose an existing one like say, ConvertKit, how comfortable are you with it? Have you done this with it? Have you done that with it? What is your number one goal now in joining the email list? I use that to basically build a profile, the new subscriber. And then what I wanna do from then on out is to think how do I take into account when somebody shared with me and give them better content? That’s my focus is like, people. I wanna have a strong signal relative to the noise that I’m producing to each individual subscriber. So what I do with that is for things like sales email, so I just did a Black Friday sale. There were a lot of, the emails I sent were tweaked based on that underlying data. And yeah it’s worked really well. I actually have a write up from last Black Friday that showed the percent increase because I did some A/B testing back then of what effect this sort of email tweaking had and it was significant. I’ve got the exact percentage, but it was something like 60%. I can, I’ll find the Twitter thread that I did a year ago and share it with you if you want. But yeah, I mean, it’s one of the things that makes a lot of sense where if you can reposition or focus a message to show somebody why they uniquely would care about this thing. It makes to you don’t need to overload your emails or overload your messages with like all the different various edge cases and, you know, conditionals and stuff like that. So I think onboarding emails, yes, sales emails, yes. Those are high value emails that tend to be evergreen, especially the onboarding ones. Those tend to be, you set it up once and it just runs. My other thing, when it comes to like my weekly newsletter is I actually don’t really do any personalization with that. What I do instead, which still counts as personalization is I have what’s called an Offer Funnel that I have running in the background. And all that is, is a fancy automation that doesn’t actually send an email. So it’s a visual automation in ConvertKit that does not send emails. Instead, what it does is when inputs occur, so when somebody changes their segmentation or they buy something, it reruns. And it just runs through a bunch of if else gauntlets to figure out what should somebody buy next from me, of the products I offer. And then what I do is, I then have a call to action in my newsletters that just pull from, you know, this specific person. This is what they should get promoted this week. And sometimes, I haven’t done it with creating sell yet. But with Double Your Freelancing, my other brand, I’ve gotten really fancy and I have it like rotate through different things. So it’s not the same thing every week. But my thinking is, I wanna be able to write an email, write a new article that I’m really passionate about, blast it off to the entire list, but have the call to action at the bottom, be dynamic relative to what somebody’s bought or hasn’t bought, and what they’ve told me and why that should affect them buying this product versus that product. Like so if they don’t use ConvertKit, they’ll never see a promotion for Mastering ConvertKit because that’d be stupid. But if they don’t use anything, maybe I drop my affiliate link for ConvertKit and say, hey, looks like you don’t use any email provider yet. Here’s my read up on what you should use. I recommend ConvertKit. Here’s some, here’s the link to go get started. So my thinking is I wanna and that’s part of the template that’s part of the shell that I just go with. I fill in the middle bit and that stuff happens under the hood automatically.
Arvid Kahl
Oh, that’s cool. That sounds very thought out. And that is kind of the scary part here for me at this point to think of oh, wow! Now I have to think of all these different alternative states that my customer could be in. And I have to consider not only what state they might be in but how I could then approach them the best way. And I know this is just work. You just have to put in the time and effort to figure it out. But that kind of scares me to have to do this and then have to set it up right and probably have a hard time testing it. Because you know, you can’t just like hope that people get to the right email. I kind of have to figure, it feels like there’s a lot of work. And in my mind, what has kept me until now from doing this is exactly this fear of like, what is oh, I might maybe over segmenting these things or under segmenting them? Am I doing too little, too much? Am I doing it right? Do you have any kind of, I don’t know, resource or hint for how to get started with this to just go baby steps?
Brennan Dunn
Yeah, I mean, my recommendation would be if you’re a creator and you have a few things for sale, always you probably have a product that is a good like entry level product for most people, right? So it’s what you recommend most people get first. I would just think like, alright, so I’ve got this entry level product. What should most people who buy that probably buy next? And then it can be a really simple linear, easy to construct thing that says, if they haven’t bought this, show a promotion for that or an ad basically for that, else, if they haven’t bought this, show that and just have a go through like a very simple linear thing. I mean that at a minimum gives you what you need. And the benefit there is if they get an email from you today and it’s promoting product A. And then they go and buy product A. They get an email from you next week, they’re now getting promoted product B. Whereas somebody who hasn’t bought anything is getting A, so it’s just a way to kind of, you know, it doesn’t make sense. Some people will like randomly mix up their products in emails that they send. And you know, this week, I’m hard coding in my newsletter edition, a promo for this. And sometimes they’ll go even further and conditionally only show that if they haven’t bought that, but a lot of people probably don’t do that. They just have the promo for that. This is just in my mind a lazy way that has a lot of our print setup time. But once I have it set up, it’s really just a thing that makes a lot of sense, like show promotions that relate, you know, to what somebody’s bought. Or you can do fun stuff like say you have like a self study course or an ebook that then you know is cheap. So you want most people to buy that first because it’s low risk. And then you have like a higher price course video course and then you have like coaching or something. You’re probably not gonna be able to push coaching on somebody who’s never bought from you because usually when those who’ve done coaching or have like, pricey masterminds, it’s usually people who bought our stuff, who get a lot of value from it and who then go on to buy the coaching. So it’s the same kind of thing where you’re just saying push the coaching to people who are already customers. Push the cheapy book to people who are not customers and haven’t trusted me yet with money. And it’s yeah, just makes a lot of sense. And it’s just, you know, once you do it, it’s automated. You just kind of do your usual email thing. And these ads get automatically included.
Arvid Kahl
That sounds like a good investment of time and effort. I will refocus my priorities around them. Honestly, yes, you can do so many things, right? As a creator, that’s the thing. That’s why I said earlier, you wanna spend as little time on those platforms like you wanna do all the things. You wanna create, you wanna market, you wanna be there with the people that you wanna help, or you wanna be on Twitter, or whatever platform du jour that we are on today. You know, you’re just all present in all fields and setting up something like this that is an automation that does the work for you, now that’s just smart. Like I really liked this. So thanks for mostly giving me something easy to start with. I think like
Brennan Dunn
Of course
Arvid Kahl
You can do so much segmenting along the way, right? For all these different things. It could probably figure out do people like my podcast more as a video than as an audio thing and then drop the video link or drop the audio link corresponding to what these people chose before. Now, one thing, I would assume you do this through tagging people with particular data tags or bought this thing or whatever, like put some data in there. Is there anything specific about this? I don’t really wanna go too deep into the technical here. But like, do you have any kind of hints on how to best both associate that data? And then I have a second question that I’d wanna throw in here as well. What about data that you can reliably get from the platforms that you sell your stuff on? Like, I’m on Amazon. I sell my book and stuff through Amazon and I don’t really have any way to get this information from Amazon who bought what. Like, what do I do about people that I sent to Amazon and hope they bought? Like, how do I express this for something like _?
Brennan Dunn
Let’s start with that one and then we’ll move to the first question. So with Amazon or any like, say it’s a I don’t know, some reseller who does, you know, you get royalties, but you don’t get customers from them. It’s never gonna be foolproof. But what you could do would be let’s say you’ve linked to Amazon, you could know that they click that link. And you could follow up with a very simple email, say a few days later that says, hey, I saw you clicked over to my book on Amazon. Did you buy it yesterday? They click yes, you just kind of then segment them as a customer, but it’s by no means foolproof. Another thing you could do would be if you have the book itself, Josh Kaufman does really well. If you have the book itself, links that link your site that really are kind of private links that only readers the book would have. And it’s like, you know, get it bonuses related to this chapter or something like that. You could kind of safely assume that people going through that flow own the book. One thing Josh Kaufman does The Personal MBA, which I really like, is he puts at the beginning of the book, hey, if you, you know, snap a picture of your receipt from, you know, Barnes & Noble or Amazon or whatever, and forward it to like, you know, my book at joshkaufman.com some address, I’ll send you some freebies that like videos and stuff that accompany this book. And all he does is it’s super simple. Just I think it’s a zap that just looks for any
Arvid Kahl
Auto replay?
Brennan Dunn
Yeah, any email that hits that gets then pushed into a CSV and segmented as a book reader. Sounds like it’s pretty basic. So anyway, that’s what I would do for that. But again, it’s never gonna be super foolproof. When it comes to technicals, so when it comes to, let’s talk about technicals of like, how do you promote a certain offer to somebody? My thinking here is I like to have my emails be dumped. And what I mean by that is I wanna just be able to say in my email template, if next offer equals Mastering ConvertKit show and after Mastering ConvertKit if next offer equals Palladio show up at for Palladio, I don’t wanna know how they’re offered this. I just want the template to say, hey, what is the field next offer equal to? And then so what I have is I have that automation I talked about. That for visual automation that it reruns whenever somebody’s segmentation or purchases change. And all that does is it goes through and says are they segmented as a buyer of Mastering ConvertKit? If they are, don’t you know they’re not gonna get next offer equals to Mastering ConvertKit. They’ll go down to another fallback. So that automation centrally manages this custom field called next offer. And it runs when prompted and it runs when somebody first joins the list too. And then that way, anytime like if I wanna send an email to say target anyone who I think should be buying Mastering ConvertKit next, I just go and send a broadcast and say target people with next offer equals MCK. And that’s what does it. And I prefer that because then you don’t need to be thinking like, God, how am I tracking people who, you know, how am I doing that again? I’m also a really big fan of documentation. So I have a Google Doc that specifies all the custom fields I use. I don’t use any tags. But if I did, it would show the tags. But mostly all the custom fields and their possible values. Because with ConvertKit, custom fields aren’t, they’re not list, meaning you can’t have like an enum field that has set values. Instead, it’s open ended. But what I do is I shove into, like, say I have an MCK status field, right? MCK is short for Mastering ConvertKit. And if it’s blank, that means they haven’t done anything. If it’s visited, that means they visited the sales page at least once. If it’s set to purchased, they bought it. If it’s set to refunded, they’ve got a refund. And why do it that way is it now is effectively like a state machine where no one can be both purchased and refunded simultaneously. So that field reflects what is their current relationship with this course. So if I ever wanna know who’s bought Mastering ConvertKit, I just say who has MCK status equal to purchased? And that’s my segmentation. But I don’t wanna remember that, right? I don’t wanna remember that when I’m setting up these conditional things. So what I do is in that document, I just have basically a little table thing, MCK status in one column. And then I list out the different options and what they mean. So purchased, this is set, you know, when somebody owns the product or whatever. So yeah, I’m my big frustration with whether it be ConvertKit or really pretty much every ESP I’ve looked at is they don’t make it intuitive or easy to look at, like, you know, how is this field getting changed? Or how are people getting on to my list? There’s no easy way for you to safely extend things because you’re never quite sure like, is this field or tag being used by an email? Can I get rid of it safely? Can I change it safely? So I like having a simple Google Doc that just lists out kind of in almost programmers terms like technical documentation, these are the different, you know, this is the data. That is you know, the database schema, if you will. For my subscribers, this is what all the different fields do. This is how they’re set, this is where they’re read and then I can just in one place. I mean, it creates a bit more work when I’m doing stuff, but it’s a lot safer for me, because I know, oh, I can screw with this. And these are the things that will get affected. So if I wanna screw with this, I need to go make sure I don’t screw anything up over here.
Arvid Kahl
Oh, yeah, I guess we have to build these little crutches or as we developers call it documentation to deal with the shortcomings. And I mean, it’s just like we wish the world were perfect, right? And then we would have no problem. We would get immediate information on oh, no, don’t remove this tag. It’s being used over here. But it’s not a business case ready for ConvertKit to implement that, right? They want you to grow your list because their value metric is how many people are on your list, not how easy it is to remove a tag. And maybe let’s talk about email lists a little bit because I’ve been hearing people referring to email lists as either as newsletters or as lists. And I think it’s a good opportunity to talk about like the definitions here. What’s the difference between an email list and a newsletter? You as an expert probably have a very defined opinion.
Brennan Dunn
I mean, I don’t have like I think I mean, the big newsletter thing is a bit of a fad, I think in the sense that it’s nothing new, like it’s been done for
Arvid Kahl
Old letter?
Brennan Dunn
Yeah, I think it’s, I mean, the word again, I’m not a meta historian when it comes to like, the art of the newsletter. But I think they started out as like printed things like here’s the neighborhood newsletter, and you can get in, you know, like locally or something. And it would be like, like, Oh, here’s a little carnival we had at the park. Or you know, this person has the garden of the year or something, right? Like, it’d be way to announce things, which is the news in newsletter. But I think most of it are now most of us. Well, originally were using newsletters as a way to basically keep a list warm and deliver a lot of trust or create a lot of trust between you and your subscribers so that you could eventually cash out and sell something to them. Which is basically I think the how most of us online creators look at newsletters. That’s sort of shift though with this whole like newsletter ad thing, where you know, people are getting paid to write broadcasts emails. And that’s kind of the end goal for some people instead of selling a course or product or coaching or whatever else. But I think traditionally, the way I’ve always looked at it as you know, you wanna be able to. First off, you don’t wanna just show up anytime you have something to sell because that probably wouldn’t work. I mean, it would work, but you get a lot of unsubscribes. And on top of that, you want to show people that you have a lot to offer that you’re smart about stuff and that you can help them in some way. And so, you know, the normal formula has always been usually has been show up usually once a week, with a valuable piece of content, send it to your list. And then every few months or whatever, shut down the entire list and just send like a week’s worth of high hit, you know, heavy hitting sales emails, and rinse and repeat. I mean, that’s what people like, you know, OG people, like remain steady and people have been doing for a very, very long time. So I don’t look at it as being like, I look at newsletter as being a more manual nurturing email, you know. It’s not like an email course, which is automatic. It’s not like onboarding emails, which are automatic. This is a manual, usually a broadcast thing that could go and its job is just to kind of send more good content to your list to keep them liking what you’re sending and wanting to read your emails.
Arvid Kahl
Right. So it’s just like a part of the whole overall strategy to have a newsletter and newsletters just like a distribution method, really, to get something out there.
Brennan Dunn
Yeah
Arvid Kahl
To nurture
Brennan Dunn
I mean, I think like when it comes to newsletters, it’s usually you have like some sort of welcome sequence or onboarding sequence that acclimate somebody to your brand and what you’re up to. And then usually, you dump people into your life newsletter, from there and out. And like I said, then occasionally you pitch stuff. And that’s usually the formula for most people. You can get crazy fancy and do things like having automated newsletters, which are then just really sending weekly stuff that looks real time, but it’s not. And then like automating your pitches and all that stuff. But for the most of us are just keeping it simple and saying welcome sequence brings people on, then we put them on our, you know, now they’re getting our newsletter and then sometimes it’ll get sales emails from us.
Arvid Kahl
Yeah, I forgot one thing in my whole strategy over the last couple of years. I’m gonna tell this to you because you’ll probably understand how disastrous this was as a mistake to have made, but I get a lot of emails from people buying my stuff on Gumroad. Because most of my products are on Gumroad as ebooks and my courses only really available there. So I get all my course sales and my ebook sales from that particular platform. And they get fed into my ConvertKit list, which is just one big list and half of the list really has my newsletter and the other half does not. And for the last years, I only implemented this a couple of weeks ago. I did not tell the people who bought my products on Gumroad that I have a newsletter through that list. I did not have a follow up email to tell them, hey, if you’re interested, here’s something every week. Like there’s half of my list that doesn’t know that I have a newsletter, even though they’re on my list. It’s bizarre, right? Is that a big problem? I just wanna know.
Brennan Dunn
I mean, I don’t know if it’s a big problem because I think the default thing most people do is they would just add any customers to their newsletter. They wouldn’t really because a lot of people, frankly, when they’re sending a newsletter, it’s a broadcast to all subscribers. So they’re not actually that nuanced. And I mean
Arvid Kahl
Am I too kind to the people on my list? Like what’s going on here?
Brennan Dunn
I think I mean, different schools of thought I would say. Some people would say, if they’ve bought something from you, they wanna get more from you, right? And they can self select out at any time, but that unsubscribe link. But I think having a courtesy email or ideally set of emails that when somebody buys, you nudge them toward hopefully joining your list with one click, which really just segmenting them. I mean, they’re already on your list, but they’re not segmented as newsletter person. Yeah, you just have a link trigger that basically does that. And then you drip out a few emails. And if they don’t do it by the end of it, they’re just kind of in the other sitting there forever. But yeah, I mean, that’s basically because I think like that’s another thing too is I think being segmentation, we usually think of as being used to or we don’t actually use it. Think of it this way I should say let me rephrase this. Segmentation, we usually think of as a way to say, oh, this person’s interested in that, and they like this, and they’re struggling with this. And then we can use that to dynamically generate more relevant content. But segmentation can also include the relationships somebody has with you and your brand. So like, we know we think of newsletter. Being on a newsletter is an atomic thing, where it’s either you’re on it or you’re not. But what if you wanna say maybe you have like a monthly digest that you can say actually don’t wanna unsubscribe, but I wanna get a once a month thing instead of a once a week thing. So like, that’s all segmentation. And all that means is like, if somebody is buying it, they’re entering your list. If you can have mechanisms for say, hey, I have, you know, this weekly newsletter. So you wanna join it? Or do you maybe wanna get a monthly version? Yeah, I mean, then it becomes really easy for you, as the creator to say, cool, when I’m sending a newsletter, I’d send it out to newsletter status equals monthly or just sort of status equals weekly. And there we go, news of people, like I don’t know how their weekly. I don’t know how their monthly. But again, that’s what I’m really big into, like, dump implementation, if that makes sense, where I don’t really care about how, you know, they ended up this way. Yeah, I just want it when I’m setting up my targeting, or I’m doing like some conditional content in an email itself. I just wanna keep it simple.
Arvid Kahl
Yeah, that makes sense. That’s also, that is kind of showing time as to your list of the people that chose to interact with you. I like this as an approach. And again, it feels like, oh, that’s gonna be a lot of work. But you know, that’s just what you have to put into it to build this relationship with people, right? It’s a two sided things. That’s not that these people sign up for your list. And now you could do whatever you want with them forever.
Brennan Dunn
No
Arvid Kahl
There’s a lot of agency on there end too that you have to kind of uphold a certain quality of the interaction for them to
Brennan Dunn
Yeah
Arvid Kahl
Stay with you. I can tell you one thing, like I said, I did not tell people about my newsletter. And one person that I sent a Black Friday email to very recently, wrote me an email back almost being outraged about the fact that I hadn’t said anything to them for the year that they had been on my list. And now I come with a marketing offer. I asked this person to be on my list. They would have got a weekly email. I would have value nurtured them. Show them that I’m still thinking about stuff beyond the thing that they bought. And here’s more, here’s more every single week, they probably would have reacted way differently to that marketing email than if I hadn’t made the mistake for years not to tell them that there is a newsletter. So I just wanted to share that as a don’t do this at home story.
Brennan Dunn
A lot of these mistakes seemingly are made where we just don’t really ever put ourselves in the foot or the shoes or we don’t intentionally think through like what somebody think about this. Like, let’s say we’re doing a list, why launch of a new product? Are we thinking about the person who joined yesterday? You know, if they just came across your stuff for the very first time from Google, they opt in your list. Now they’re getting on a week long, heavy hitting like buy, buy, buy sales thing and like, what does that do, right? Like that’s I think it’s this empathy thing you brought up like being thinking through, like, who’s receiving this? And I think a lot of it is just the convenience of being able to say, we’re gonna send a broadcast that is gonna be a sales email and I’m just gonna do the default all subscribers thing, which is what ConvertKit default seems to be doing and do it that way. So anyway, I didn’t mean to cut you off. You’re gonna, you’re saying something.
Arvid Kahl
Nah, that’s fine. Like, I understand that people choose the easy way when it comes to interacting with their audience because they are used to broadcasting. That’s the thing, right? If you look at Twitter or Facebook, unless you’re in a particular group, or twitter circle, or whatever that were feature, that’s probably gonna be gone by the time this is released. It’s called, you know, like, these little subgroups, but usually you broadcast to your audience with one message. The segmentation, like you said, in the beginning of our conversation only exists where we choose to implement it, but we have no choice to implement it on social media platforms. I guess the default would be broadcasting. And I thought about doing this with my list. But I really didn’t wanna surprise people in a negative way. Because I know that every interaction that I have with the people that already gave up their private information, right? They gave up their email to me so I could reach them. That’s a big gesture. And I’m, that’s the thing I’m really thankful for every single person that puts their email into this field because I know that I don’t like doing this at all to anybody. I don’t give my stuff to anything that I don’t think is gonna be super valuable or that I can trust. So I know that this happens at scale for people who subscribe to my products or newsletter, whatever. So just pumping out stuff at them feels like I’m not valuing them. And that’s not the brand that I wanna have. That’s not how I want them to feel and then tell their friends about it, right? That’s kind of the thing. So let me ask you a more tangible question here. Tell me a couple more things that people who get into email marketing are doing wrong, that they misunderstand in this kind of way where they only kind of think about themselves. So what have you seen in email marketing that most people get wrong there?
Brennan Dunn
I think a big thing is, I wouldn’t say it’s a specific thing. It’s more of a relationship with automation. So I think a lot of people are put off or intimidated by email automation. I think the really the big reason for it is almost thinking of it as a bit of a runaway train, like you never know. Like, what if 50 emails go out to somebody in one day because they happen like the stars line. And now these different automations are all, you know, working on them. My thinking here is the issue I have with broadcast based stuff. Let’s say you decide next week, I’m launching this new thing I’ve been working on. That’s your schedule, right? That you’re ready for that. You’re ready to launch that because you’re done with it. You’re ready to unveil it. But that might not be when the people on the receiving end are ready for it, right? So I think like automation done rate should be more about thinking, how can I build a system that when somebody comes on board, when somebody joins my list, I try to uncover however I can a bit about their goals, a bit about situationally where they’re at, a bit about their identity, maybe what industry they’re in, what job role they have, whatever. And then how do I put together a choose your own adventure style experience for them that allows them to be recommended products at the right time? And it’s that whole thing like send the right message to the right person at the right time. Like how do I do that? How do I make it so instead of just one size fits all blast it out vice versa Stripe revenue, rinse and repeat, again and again? How do I instead think?There’s a lot of people who are joining my list. People come on every day, people leave every day. How do I curate a really great experience for them so that people are getting relevant content at the right time? And that when they virtually raise their hand saying I’m ready to be a customer of something that you offer, how do we then and only then provide that to them? And I think that’s something that the UX of email isn’t really thought about too much. I think people are so obsessed with like marketing campaigns. And thinking about like, what we’re doing this week when it comes to the emails. I mean, my end goal. You know, I think, again, to go back to the automation thing, I think a lot of people associate automation with sitting on a beach and doing nothing and getting paid. And that’s why we do automation. I look at it as automation done right, provides a better user experience to your subscribers because they’re getting the right. Like most of us, let’s be honest, aren’t sending like stuff that’s super timely like Bitcoin prices from yesterday. Like for the most part, a lot of the news that we’re sending in our newsletters is advice, or it’s, you know, insights, like these aren’t timely, right? Like if I wrote it in Senate today or if somebody if I wrote it a year ago and somebody gets it for the first time today, is it really that big? Like, who cares? It’s like a book, right? Like, who cares? I think like, if you can start thinking of automation is being a better UX or delivers better UX to your readers. And when somebody has better experience, they’re more likely to engage with their stuff and they’re more likely to read it. They’re more likely to buy. It ends up being a really great win-win for everyone. And on top of that, I think like, I look at my success as an email marketer is being how few times can I log into ConvertKit. You know, like, I think if I need to be going in and feeding the monster and thinking, crap, if I don’t write an email this week, the list will go cold or something and I won’t be able to promote. Like, that shouldn’t be what we’re doing. We should be thinking choose your own adventure stories, like different people have different needs. They’re in different places. They have different levels of awareness. How do we cater to that. And that does take time and thinking and planning and work to set up. It’s not something you’ll build overnight. But I think for most of us, that should be the end goal.
Arvid Kahl
I just wanted to agree this whole time because I feel like what you’re doing is so customer centric. You’re putting the person that you’re talking to first, like what are their needs. And that’s what marketing is about, right? Like finding people who need this and give them the thing that they already know they want and could just help them figure out how they can get it through you, from you. But it’s such a thing that I often feel is totally absent in the emails that I receive is compassion from where I am, like because the people want. I think the phrase here as my inbox is somebody else’s to do list too often, right? It feels like
Brennan Dunn
Yes
Arvid Kahl
What email I receive is not for me, it’s for them. And that making that a choice to not go that way and instead choosing to use automation to provide a better experience, that is just a mindset shift. That if you can do it from the beginning, is gonna just make such a better experience possible for the people that you’re interact with. And that is the word of mouth that people will present to their community. So like because newsletters are not usually recommended because they all have like the most genius insights. People recommend the newsletter not as a per issue thing. That’s how I feel at least in the perception that I get on Twitter when people recommend newsletters. They recommend newsletters because there’s a great person behind it doing them. And then because over time, there’s this wealth of knowledge that is presented in an approachable and consumable form. So it’s not the individual issue and the design of that particular piece of content that matters. But it’s the feeling that people get from being recognized as somebody who should read this, that they then spread into their communities. So thinking from that person first, that is really, really helpful perspective to take. I would like to look on the other side of this because there’s a lot of opportunity in email. But is there also risk? Like that’s what I always wonder, as an entrepreneur. Like is there a risk in reaching out like this to people or even setting up automation like this? You kind of touched on it just now with 50 emails on one day, but are there any risks that you haven’t talked about just yet in building these complicated email systems?
Brennan Dunn
Yeah, I mean, the big risk is ultimately gonna be not having a good control technical developer. It’s not having strong control over what you’ve got in place where people are flowing in and out of automations. You have no idea how that’s happening. You modify one automation and now that automation may be fed people into a different automation, which is like where the sales happen, that stops now. And it’s the risk of just making changes that have really big consequences. And my way of mitigating this risk is really strong documentation. Because again, there is no unit testing platform for ConvertKit. There’s no way to say, I wanna have, here’s an automated test that given a new subscriber who has this bit of data attached them. They should go through this flow in and out, you know, end up this way. Like there’s no way to do that, right? Like yeah, so the only way to do that at the minute is to just have documentation that is not stale, that is continuously updated. So if you make a change to ConvertKit, you pop over your Google Doc and update it there. That’s honestly the only, you know, from a yeah, I mean, like, well, there’s that risk, there’s another risk I wanna talk about too, which a lot of people don’t really mention is the kill switch. So really bad things happen, right? Like, take 9/11 as an example, right? If you have an automation that is a sales automation, these automations usually tied to a weak case. You can’t say ignore it around Christmas. You can’t say ignore it around this date or that date. And you definitely can’t say monitor the news. And when something is really a big deal, don’t start sending out shitty promotional emails. So I try, I built into my setup, a thing where it’s effectively a kill switch. So ConvertKit doesn’t have global variables. So what you need to do instead is you basically update every contact record or subscriber with. Basically, I have a deliverability field that I can set to don’t. And then all of my automations look at that in order to determine can somebody actually get this email? So that’s like, the end thing is, if they can’t. So the benefit there for me is, I know I can go in if there’s a giant tragedy and run a single bulk operation that sets this and then I don’t need to worry about stuff like that go out. And that’s, I think, the big risk, I think, us as marketers, we’re fine to do that. If we’re sitting broadcasts, you just know, okay, I’m not gonna send anything today. But when you have a bunch of like little mini automations going left to their own devices, they’re not gonna care or know that today’s a big holiday or that a big tragedy just occurred. So I think that’s a risk that I think very few people talk about. And I haven’t seen any ESP that has this built in. It’d be great if they did. But yeah, that’s another big risk too.
Arvid Kahl
That’s really cool. Never thought about that. Like I usually, honestly, with my approach to this, I don’t have much in terms of automation. Most of it is really just me manually broadcasting. I kind of cool it in those kinds of situations, but I still keep like some semblance of communication going because I feel like as much as in such a situation, you wanna be careful with a global audience. Just kinda hard to judge, right? Like obviously 9/11 is a global tragedy and there are many of these unfortunately. So kind of toning down their marketing outreach on those days is generally a good idea, but just even who not to send email to sounds hard. So kill switch is a great idea. It’s great to think of implementing this as a flag and then kind of switching it off and on if you need. That is really helpful. Thank you! That is a risk that I did not have on my mind at all. That’s really, really cool. Wow, the feel of email marketing isn’t really new to me. But the nuance is quite tangible. Like there’s a lot of things that you don’t think about because you are so used to other kinds of medium like Twitter or social media in general. Maybe as a final point here. If you were to look at the landscape right now of the way that people reach out to each other on Twitter, Facebook, LinkedIn, whatnot, do you see email as the kind of medium for people to de risk their social media presences? Is that something you would recommend to anybody? Or is it something you only would recommend to marketers or content creators?
Brennan Dunn
I mean, I think it does, I’m not. So put all my cards on the table. I’ve heard a lot of things about how people who are much younger than me don’t use email anymore. That might be true. Part of me thinks when they get into real world, they will use email, maybe I’m wrong. But yeah, imagine a 12 year old starts using an email, you know, maybe there. But I definitely think email is the way to go. There’s two reasons for that. The first is that it’s portable. You can’t be deplatformed. And I know we tend to think of people being deplatformed. Whether on like political streams or whatever. The fact of the matter is, deplatforming could be also Facebook up to a particular algorithm to make it. So the likelihood that people who follow you see your posts is significantly less unless you’re paying them money, right? Like that, email is peer to peer. It’s not centralized. It’s literally the tech is 50 something years old, where it’s basically saying like, it’s an SMTP server that’s knocking on the door of a receiving server and saying, I have a message for this user or this account on this system. Like when you look technically at how it all works, it’s super old. But I mean, it works. An email is basically think of it as a file. I mean, that’s basically what it is. Once it’s delivered, it’s delivered. Yeah, I mean, Microsoft and Outlook can have like unsend email as a feature, which is more of a handshake agreement between two Outlook clients, but it’s not built into email. You send me an email and you try to unsend it, no. I’m getting it. But yeah, I mean, ultimately, I like email because it’s very low risk. And I can move from platform to platform if ConvertKit won’t have A or if they’ve screwed something up big time, I can move elsewhere. And take my list. It’s a CSV file and take it wherever I wanna go. The other thing, I think because it is peer to peer. Like we mentioned is with Twitter, I can’t say I wanna tweet this. And I only want people who use ConvertKit to see this, no way of doing that. Whereas with email, assuming you have that data of do they use ConvertKit, yes or no? You can do that. So from a messaging tool, it’s a lot more flexible because you can truly personalize the content you’re sending in a way that you just can’t with social media.
Arvid Kahl
That’s derisking on many levels, right? It’s like the resultant of the deplatforming and also enabling you to not have to send the wrong stuff to the wrong people. That is, you know, like to prevent you from like over saturating the market. Very cool.
Brennan Dunn
Here’s a quick innocent example I wanna share. I know we’re ending but with that derisk. Let’s say you tweet your Black Friday sale and somebody bought at you at full price. They’re gonna see that tweet. I mean, they might not if they’re not looking at Twitter, but they’re eligible to see that tweet. Whereas if you’re doing your email, right? You’re probably gonna exclude people from seeing a Black Friday email about something somebody’s already, oh somebody already owns. So that’s another just example of like, you know, you’re not doing that in a nefarious way. You’re doing that just because why promote something that somebody already owns? I didn’t mean to cut you off. But that’s how I wanted to also mention derisking.
Arvid Kahl
That makes sense to us. Like that’s a saturation argument, right? You don’t wanna over saturate somebody who already is at the point where you want them. You don’t wanna throw more on them. So with somebody who bought this stuff to, very cool. I have one final question for you. And it’s of a personal nature. How many eggs did you eat today, Brennan?
Brennan Dunn
So Laura has told you about my new diet.
Arvid Kahl
That’s right!
Brennan Dunn
So far, I’ve only had two but I did eat a steak already for my first lunch. So
Arvid Kahl
Wow, you’re building the monolith, right? Is that what you’re doing?
Brennan Dunn
That’s the program I’m running and it’s been kicking my ass. So, yeah!
Arvid Kahl
Yeah, I bet, man. That sounds like a lot of protein. Yeah.
Brennan Dunn
Yeah. 200 something grams a day.
Arvid Kahl
Yeah. Wow, that’s substantial. Well, we all run these little experiments in our life, right? To figure out a better way forward. That is really cool. Well, thanks so much for being on the show today. Where can people find you? Where can they learn more about what you’re doing and what you have to offer?
Brennan Dunn
Yeah, thanks. So first of all, thank you so much for having me. It’s been so much fun. https://createandsell.co is probably the best place, that’s my weekly live newsletter. It’s not automated yet. But that’s where I send out stuff on just kind of like what we talked about today, email marketing stuff. We talked about Palladio and getting to Palladio is palladio.dev. And I’m on Twitter, twitter.com/brennandunn. So yes, thanks.
Arvid Kahl
Yeah, I recommend people follow. You’re source of great insights and great humility and just a good person to be around. So thanks so much for being on the show. That was awesome. And thanks for sharing all your knowledge today. Wonderful.
Brennan Dunn
Thanks, Arvid. Yeah.
Arvid Kahl
And that’s it for today. Thank you for listening to The Bootstrapped Founder. You can find me on Twitter @arvidkahl. You’ll find my books and my Twitter course there as well. If you wanna support me and the show, please subscribe to my YouTube channel. Get to the podcast in your podcast player of choice, and leave a rating and a review by going to (http://ratethispodcast.com/founder). Any of this will help the show. So thank you very much for listening and have a wonderful day. Bye bye
What We Talk About
00:00:00 Brennan Dunn
00:00:48 What is up with email clients?
00:05:05 Integrating with large platforms
00:08:34 Maybe build a competitor?
00:12:12 Emails and metadata
00:16:20 Email personalization and how it works
00:22:07 How do you get started with this?
00:25:28 Focusing time and effort on certain platforms
00:31:24 The difference between an email list and a newsletter
00:36:30 The importance of segmentation
00:41:06 Use segmentation to increase your list
00:48:56 Customer centric marketing
00:54:24 Is email the right medium to de-risk?
00:59:20 Don’t over-saturate
