Combining personalization and automation for next-level email marketing

Brennan Dunn is the creator of Double Your Freelancing, RightMessage, and Mastering ConvertKit.

Brennan is one of the most well-regarded email marketers on the planet. Using cutting-edge techniques in personalization, Brennan has generated millions of dollars in sales of his products – and a lot of that is automated.

After starting Double Your Freelancing as a blog in 2015, Brennan realized that he could more effectively sell his courses using personalization on his website and in his email. In 2018, the founders of ConvertKit, Teachable, and convinced Brennan to create a software platform called RightMessage.

Brennan teaches his advanced use of email marketing in his popular course, Mastering ConvertKit.

In this episode, we talk about how Brennan built his broad skillset, the job that changed the way he thought about sales, why he built an agency and ultimately closed it down, and how Personalization creates a better experience for your audience while also increasing your revenue.


Learn more about RightMessage

Subscribe to Create & Sell

Learn more about Mastering ConvertKit

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Brennan Dunn 0:00
My mind was blown because I was doing like, I had this 20 person weekend workshop that I charged 1000 a head for. And I'd make you know, I'd bring in 20,000 a weekend, and the SAS was doing like 2000 a month at the time.

Jay Clouse 0:15
Welcome to Creative Elements, a show where we talk to your favorite creators and learn what it takes to make a living from your art and creativity. I'm your host, Jay Clouse. Let's start the show.

Hello, my friend. Welcome back to Creative Elements. If you've been listening to this show for a while, you may see a pattern emerging from the creators that I've interviewed. Regardless of platform, just about every creator I talked to on this show references writing as an essential part of their business. And more often than not, they talk about email as well. Email is one of the oldest aspects of the internet itself. And usually the oldest aspects of something are the first pieces to be innovated on or even eliminated. But email just seems to be this piece of the digital toolkit that isn't going away. Even with messaging platforms like Slack and Discord, or social media platforms. Email seems to be here to stay. And if you spend some time talking to creators about email, how they utilize it, and where they've learned some of their more advanced techniques, chances are, they will reference today's guest. Brennan Dunn calls himself an email marketer. But to me, he's more like a digital unicorn. He can code, he's a great web designer. He understands sales psychology, he makes incredibly well produced online courses, and even had a podcast for a while. But at the core of all of Brennan's work is incredible innovation in the form of email.

Brennan Dunn 1:55
Email marketing automation, to me is the ultimate combination of creativity, because I get to do with like, persuasion and sales, copying, and stuff like that, along with the stuff that makes the programmer me really happy. Like being able to do stuff with conditional logic.

Jay Clouse 2:13
This really started with Brennan's blog, He realized that there were all kinds of different freelancers, a problem that I found with freelancing school as well. You have designers, developers, copywriters, coaches, consultants, marketers, on and on. And with so many different identities, it was hard for him to make it really clear on his website that his articles, his courses, and his other content could help any freelancer. But he had to break through and realize with some basic coding, he could personalize his emails on the fly, to speak directly towards the reader.

Brennan Dunn 2:47
I could just focus on that I could use language like fees or something that would work for them. Whereas, you know, budget might work for designers or something like that. And I could just tweak bits and pieces, so it's a little more specific to them.

Jay Clouse 3:00
As you'll hear in the interview that had an immediate and meaningful impact on revenue, then he went beyond email. He wanted to learn about the reader when they landed on his web page. But before they had even subscribed, he built some custom code so that his website could personalize messages on the fly too. That code eventually became a software platform called write message, which Brennan focuses the majority of his time on today. But Double Your Freelancing not only continues to exist, but it continues to generate meaningful income for Brennan, because he really doubled down on email marketing and automation.

Brennan Dunn 3:33
It was easy because I intentionally build up you're freelancing, and all the marketing arms have to be optimized that if I were to go into a coma, there'd be no impact on cash flow. So everything's automated and still is this point.

Jay Clouse 3:45
So in this episode, we talk about how Brennan built his broad skill set, the job that changed the way he thought about sales, why he built an agency and ultimately closed it down, and how personalization creates a better experience for your audience, while also increasing your revenue. Brennan has an incredible newsletter called Create & Sell in a course called Mastering ConvertKit that I can't recommend more highly. We'll talk about both in the interview, and links to both are in the show notes. I'd love to hear your thoughts on this episode. As you listen. You can find me on Twitter or Instagram @JayClouse, take a screenshot tag me, let me know that you're listening. And if you're not already in our listeners community on Facebook, I'd love for you to join. But now let's talk to Brennan.

Brennan Dunn 4:32
Before I got into anything I'm doing nowadays back in early 2000s. And in high school, I almost went to art school. So back then I was go into like borders, books, music, got the computer arts magazine with the city go home and do like a little tutorials trying to figure out like how do I make this look as grungy as I can? Right? So get photos, roll down these filters and stuff. Anyway, that was my crash course I guess in design. My issue though, is I never felt That creative. Right side, I had that kind of typical thing of like, Oh, I can't, I can't draw, I can use Photoshop. But how much can I really do with that. So switch, shifted gears into teaching myself how to code first with PHP, then in the mid 2000s, with Ruby on Rails, and so build up an agency exited the agency, because I, I wanted to build my own software instead of, you know, building for other people, and started a little SaaS in 2011, called Planscope. And that was my first kind of Crash Course into the whole, like building and selling stuff online, sold that company in 2016. And the content marketing arm of Planscope was about freelancing, because it's a project management tool. And I wrote articles on like, pricing and getting clients and all that kind of stuff. So part of the deal with selling it was I get to keep the content, you can have the software, but I'm keeping the the audience and the content. So that became over you're freelancing. Yeah, I just kind of had to learn, I guess, like a lot of us how to know one guy, how do I keep afloat selling what initially was an ebook in 2012, called double your freelancing rate, which then morphed into a course got redone a few times and kind of expanded from there. So yeah, that's kind of how I got into the whole email thing was, you know, I'm kind of that stereotypical lazy programmer who wanted to be able to do things once, like I like with scripting, like set up a campaign of emails one time, and then let it run, and reap the rewards continuously. So that's what got me an email. And yeah, I mean, that's pretty much the last 15 years in a nutshell, I guess that kind of led me to what I'm doing these days.

Jay Clouse 6:46
That was a very efficient story. And open up some new pathways. I didn't know I was gonna go down here. So let me take a step back. And you said you almost went to design school felt like you weren't creative. So then you taught yourself how to code?

Brennan Dunn 6:59

Jay Clouse 7:00
That to me isn't necessarily like the obvious step. You know, from I can do Photoshop, I guess I better learn how to code. What was the the forcing function to say I want to take on this really difficult task of teaching myself how to code.

Brennan Dunn 7:14
I say that I made this big transition. But simultaneous, so the Photoshop stuff, I was also like, running a very early version of Red Hat Linux on my machine at home, which, at the time, just to connect to the internet, he basically had to write your own device drivers. So I was kind of learning the Boolean, if else's, and that sort of stuff before deciding. No designs. Not for me. But yeah, I mean, I've always enjoyed both, and I still do to this day, and that's why I love frameworks like no as polarizing but a tailwind because it's kind of like it's it's coders who basically created this CSS framework that makes things look nice. And I can work with that. Because I've always kind of straddled both worlds of the creative stuff in high school, I used to go every summer to a writing workshop, right? Did creative writing and poetry and fiction. And then, you know, I'd come back and I get back into screwing around with Linux and, you know, trying to run my own little web server and stuff.

Jay Clouse 8:15
Well, one, I think it's a shame, you know, hearing all the things that you were doing, to hear that you had this self limiting belief that you didn't believe you're creative. All those things are such innately creative things. And I don't know why it is that so often, a lot of us are brought up thinking that we aren't creative if we can't draw if we can't sketch. And I don't know what that is. But we got to fix that culturally. You mentioned that you started an agency after you started to learn to code and put these things together. That's another to me not obvious next step to me, maybe an obvious next step is to take a job. So where did you build the confidence that you could start a business or an interest that you could start a business as opposed to working at an agency,

Brennan Dunn 8:55
there were two jobs in between finishing college and in the agency. So I did work in an agency, which is where I learned how agencies work. So I did that for about a year. And before that, I worked at a company that Funny enough, this is down I was just out of college, and I was living in South Florida. And I looked up on like, indeed, or whatever one of the job boards, found a because I wanted to do programming, and I found a job that did flash development to that was kind of cool. So I, I took that job. And what they did was there was this framework called flex, which was like flash with Java or something on the back end, that I kind of immersed myself in with this job. And this company, all they did was they they would they had this kind of productized offering where they'd run Google AdWords saying hey, if you're a mortgage person in real estate one generate leads come to us for exclusively it's and what they did is they sold their clients on single page landing pages built in Flash would have like houses like faded and like a little person avatar, scroll over. or whatever, that they would basically run the AdWords to these dedicated landing pages. And then if somebody opted in, they would then deliver that lead in real time to the realtor, which was really big back in, like 2004. So this was like, most of the people were buying off the lead lending tree or the shared lead type things. And this is a really interesting thing. And for me, I was fascinated by it, because I was like, people are paying $100 for name and an email address and a phone number, which blew my mind. Like, but then then I learned about how the backend worked. And I was like, okay, they make like, 5000, if they sell it, you know, off their mortgage commission or whatever. And you get, like, you know, 10 leads you close one, it cost you $1,000, to get a deal, it's pretty good deal. that stuck with me that whole lead gen form optimization, they were running, a lot of, they were they're paying for a lot, because basically, they footed the Advil for their clients and paid them a flat price per lead. So what was interesting to me was, they really had to, if they could increase conversion substantially, they would basically up their margins, if that makes sense. And well, this stuck with me was that, in doing that, they started to do personalization, type stuff, or customization, I should say, where they would do things like, oh, if you were searching from Fort Lauderdale, Florida, they're going to basically drop Fort Lauderdale on the landing page somewhere. And just do kind of geolocation on the fly and substituting out content. And they would, you know, they did it because it made their cost per lead cheaper. So that's kind of in a way, the beginnings of what led me to what I'm doing now, in a strange way started from kind of that experience. But that was a full time job didn't last very long. Move to the agency, they were not remote. So how to kind of quit, did freelancing and got to the point where I could either turn away work, or I could scale a team. So I decided to scale it.

Jay Clouse 11:59
How long do you sit with that decision, because a lot of people get to that point where they're freelancing and get to a point where it's like I am at capacity. But to scale a team is either really unknown to them. Or if they know the trade offs, they recognize that it's a pretty big chasm to cross. So how long did you sit with this idea of do I just want to increase my prices stay here or scale a team.

Brennan Dunn 12:23
So I started freelancing full time. And then a year later, which was early 2009, is when I hired the first person to work with me. Now when I say hired, bear in mind, initially, that was just a contractor. So subcontracted out work. So it wasn't like I didn't have W2 payroll or anything like that. Just yet. Got that up to about five people who were subbing for me, these are people that I've met at like Ruby conferences and little code camps I was doing up in the DC area, decided to go out kind of on a limb, this is the hard thing and open up a physical office and convert people if they would, into full time employees, otherwise, to start bringing on full time employees, did the office thing, move to a bigger office because we outgrew it and got to the point where we had 11 people on team on the team. And we were doing pretty much all Greenfield custom web applications, some mobile apps, but mostly web apps. And at around this time, I took a course from Amy Hoy and Alex Hillman called 30x500. This is early 2011. So one of the early cohort based online courses, start a new thing. And did that and I just kind of opened my eyes to the whole, you know, wouldn't you rather have 500 people paying you 30 a month, and instead of like three clients pay you 20 grand each month, then needing to chase around invoices and stuff. So definitely got bit by that bug and the agency stuff got very good. I was very demotivated to keep doing that. So I decided to on a whim again, start a SaaS product called Planscope, which was just a project management tool to the quintessential agency builds a project management piece of software type thing that our CRM I guess, and I and I built that and then I exited the agency, I handed it off to person who was doing sales rate and effectively sold it. Yeah, went into a full time online higher scale stuff.

Jay Clouse 14:21
What about that work? Or what about that point in time became demotivating? For you? Was it the administrative stuff? Was it selling?

Brennan Dunn 14:30
administrative honestly, if you if you if you really psychoanalyze my thought process back then it would have been, I didn't like even though we had a good pipeline of work. I didn't like knowing that I was I basically created a nine to five for myself, because my employees would get resentful if I was out at conferences and which I thought is legitimate lead generation things. But obviously I'm out at like the after parties at an event and having drinks and mingling with people and all that stuff. So there was a kind of a percolation in the office. And I blamed myself. I mean, I should have probably created a better culture that this wouldn't be as big of an issue. But the feedback was, we're here because we wanted to work with Brennan, but Brendan's ever here. And my justification was, look, I'm on the road, doing what? Like, if I'm sat in my office? I'm not. That's help, right? Yeah, I just I kind of resented that, to be honest, I resented feeling kind of captive to this job I created for myself. And I really, I like the idea of that kind of that passive income, not not as much of the passive side, but more of the location independence, I could go and create some software, have a lot of people who are paying me a little bit and none of them have any sway, because of the fact of the matter is, we would have three, maybe four clients at any given time. And if one of them called saying Brennan, we need this done now. I mean, I would make sacrifices to make that happen. But I really liked I know they've kind of fallen off a cliff lately. But, you know, back when Basecamp, before they were them, and 37 signals, their whole thing was we don't do enterprise customers, because we don't want to be beholden to any one customer. So as an agency owner, I was like, Wow, that sounds great. Like, I would love to not be beholden to any single one customer. So I think that's largely what kind of demotivated me out of the agency. And not only is it a nine to five year career for yourself, but you're also responsible for making sure you're bringing in enough projects to pay the payroll, which I imagine was pretty heavy on you, if you had 11 employees, there was one time where I couldn't make payroll, I had to borrow money from a buddy of mine who had an agency when your expenses are, I mean, I think we peaked at like 60,000 or 70,000 a month in expenses, when you know, just to break even you need to bring in that much monthly a in you know, it's not recurring revenue. It's transactional, right? It's people who need a new app build great. I mean, it will take a few months. But when they finish up, there's no vacancy, right? So I mean, I think if I was if I would have had a very, you know, retainer based recurring model, or something where all of our clients are paying us a set fee monthly, it was just like a SaaS, but bigger amounts monthly. It might have not been as big of a deal for me, but it was just that constant churn of new clients coming in and always wondering, it's fine now, but three months from now. Now, how am I getting how that 60,000 a month coming in?

Jay Clouse 17:27
After a quick break, Brennan and I talk about what happens when a client project is a failure, even if you deliver on what was asked. And a little bit later, we talk about why he eventually chose to close down his agency right after this. Hey, welcome back. One of Brennan's not so secret skills is his knack for selling. When he was running his agency, even those projects were more transactional than recurring. They were big projects. So it seemed to me like he probably picked up a lot of great sales insight when he was running that agency.

Brennan Dunn 17:58
I remember the first networking event I went to, when I decided to kind of go out on my own people would come up to me and do that, you know that you did the usual like, so what is it you do kind of thing when you mingle around the room. And I remember telling somebody that I owned a Ruby shop. So because you know, Ruby on Rails. And if I was at a Ruby conference, that's what I would say, but I'm here with like, a banker or something or some real estate agent? Who thinks I'm a jeweler, or something at this point, right? So there was that kind of reprogramming? In my mind of why is it that people are paying money for code. And really, it took I think it took me get kind of getting in between my team who was doing most of the doing the clients to really internalize that people weren't just wanting to cut really large checks for lines of code. They, you know, there was a business outcome that I kind of always knew was there, I think we all know is there. But until I started to think about how do I then sell the business outcome instead of selling the talent or the tech, that's when things for me really shifted was when I really started to internalize that and start to bake into the whole sales process. Well, how do I learn about what it is? What is the goal you need to get to? How are you firing your existing website or your existing app? Like what did they do wrong? And what is this new thing that we're going to be building for you? What do I need to do differently? Because I think what I what I realized which I know a lot of us end up realizing is that you can technically succeed but it can still be a failure. Right like you can still you can build the right thing that was ordered but it could flop and I think we all have in our portfolio probably client projects where even though we built the the thing they asked us to build it didn't pan out or be successful so.

Jay Clouse 19:45
Say more about that. Why? Why would something technically successful be a flop?

Brennan Dunn 19:49
Yeah, so I mean, we would have like for instance, we had a there's one client that wanted to build this kind of social network for musicians and venues like bars and rest clients that needed to live musicians. And we absolutely sold the hell out of him on things like private messaging between the two and all these like social media, things like groups and stuff, we basically built a very normal social network for him. The problem is he never he never, we never encouraged him to go out and actually validate that this is something that the market needed. And we never actually conveyed to him that when you have this marketplace model of you've got, you know, buyers and sellers, you've got the restaurants and the bars and the musicians, it's really hard to do a multi sided marketplace like that out of the gate, unless you really know what you're doing and have big marketing spend behind you, and so on and so forth. So I think that, even though we built what he needed, we built what he told us to build. At the end of the day, his startup went down in a ball of flame. Right, like and it wasn't, I like to think of the you know, at the time, I was probably thinking that one sun our fault. It's like if you, if I one thing that I put in one of my courses in this example I use all the time is if I sell a pizzeria, the most amazing brick oven in the world, but they use shoddy ingredients, and they open up in a crappy location. And no one ever comes in the door and buys Is it my fault is the vendor that oven for them not succeeding as a pizzeria. And that's something I think we all need to kind of wrestle with, is it our job when we're working with clients to kind of get involved on the business side of things, which I think I know a lot of freelancers, especially really struggle with doing that. Because they've, I think we all tend to think I know I did that the clients already figured all this stuff out, like they're coming to us after they've already figured out the whole business side of things. But you know, let's face it, a lot of us, we have our ears to the ground, we know what's happening in the world of technology. And if we're getting commissioned to build, say, a web application for somebody, I think it's our job to not just execute technically, but execute correctly. And that means being a bit of a filter and really coaching and working with the client on figuring out how do we get you from to where you need to be as safely and reliably as possible. And sometimes, I mean, that might be as simple as starting with a type form form, and a bunch of new code type things before, you know somebody is ready to take that next step.

Jay Clouse 22:23
This is really interesting, because I want to play this out a little bit to think through this. Like to me, it makes a ton of sense if you're optimizing for ROI for the customer, and therefore a positive experience for them probably a testimonial for you maybe even repeat work down the line. If you deliver what is asked for and it fails, because they didn't do proper diligence. I mean, like the failure is probably not a positive testimonial, not repeat work. Are there other major downsides here that I'm missing that are even more problematic?

Brennan Dunn 22:53
I think it's just the fact that, like you said, I mean, there's not gonna be repeat work, you could, you could use it as a case study, even though it wasn't the mean, I think we all want in our portfolio clients who grew up because of our input. But I think at the end of the day, like if you're, if you're, say, a web designer, or a developer or something like that, the thing that I think is probably the best thing you can do to not only increase your value, and what you're able to charge, but also the likelihood that you get referrals, the likelihood that you go on to grow bigger and better, is to say, Alright, I'm a designer, they want a new website built. But what is the job of the website, the job of the website is to generate leads or generate sales or something like that. So how do I how do I allow? How do I enable design to that end? Right, rather than just focusing on the aesthetics and what it looks like and what sizes, the logo and you know, that kind of stuff, right? So I think, even though Yeah, at the end of the day, if we if we build what was ordered, and it's a failure, I would agree that I don't think it's not necessarily our fault, just like the oven being bought by the shoddy pizzeria isn't the fault of the manufacturer. But I do think if we want to have a really strong portfolio of clients who've done really, really well, because let's face it, businesses hire people to make more money or lose less money. So if we can show that we've done that, why wouldn't you want to have that?

Jay Clouse 24:18
Totally. It's pretty clear to me that Brennan has definitely taken the approach of going the extra mile to help his customers be successful, even if it's harder or requires more effort in the beginning, in this started with the content he was creating to support the customers of his software, product Planscope. But he told me it wasn't long until that content was working so well, that he began to question the software all together.

Brennan Dunn 24:41
With Planscope. You know, I built I did the marketing site. I did the validationy type stuff and build a very small launch list. But I think I I underestimated how hard it was to sell software, specifically online. So what I thought I would do, which again, this this actually came out of Amy and Alex's 30x500 program was this idea of content bombs, as they called it right? Or more value bombs, I forgot what they called it. But basically, the idea was just what we all take for granted now, which is build really good pieces of content that meet somebody where they are today. So, you know, my thinking was, if I can get somebody who's googling, how do I get clients? Or how do I raise my prices, you're probably not actually looking for software, or not looking for project management software, but the right profile, somebody who could use the software. So the mistake I made early on was I did that, and I did it somewhat successfully, because back then there wasn't much online for like freelancing advice. So this is, again, 10 years ago, I was doing this, but the mistake that I made was the call to action on the articles was to sign up for a trial of Planscope. And the disconnect that came from, I think, a discussion at micro conch A few years later was if somebody is looking for how do I raise my rates, and then they read it article, and they get to the end of it, meaning they haven't bounced, and then they're seeing a promotion for some project management tool that they want you to start. They're not in a software buying mood, they're in a raise rate raising mood, right? Like, that's what they're doing at the moment. So I shifted toward an opt in instead for a five day crash course on freelancing. And the idea there was to you know, build a list and then just kind of send out good content, and then kind of softly mentioned this software product that's associated with with the, with the content. And I did that but Funny enough, more people were interested in diving deeper into the content side of things, then the software, right, so I would get accounts. But that led me to create an E book at the time called Double Your Freelancing, right, which was the number one issue that people kept going on about, which was how do I start focusing on value and pricing on value and so on, that then turn into the consultancy masterclass, which was a two day cohort class that I ran from 2012 to 2013. That was on building an agency. So it was a two day weekend type thing. And that led to to multiple conferences, one in the US, one in Europe every year, and a podcast and all that stuff. And it did well, kind of the heyday was 2016 ish, I think. And yeah, I mean, it was just interesting, because I built this thing, but thinking that it would generate leads for the software to generate leads, but they wanted, they wanted more educational and kind of coaching stuff, right? So ended up thinking I can't keep juggling the SaaS and the other side, you know, the majority side side that's actually paying me like a lot more than the SaaS. So I ended up selling the SaaS.

Jay Clouse 27:41
In that moment before you sold a SaaS.

Brennan Dunn 27:42

Jay Clouse 27:43
How did that feel to you to be like, I built this thing in the purpose of selling SaaS. And now the thing is working in the SaaS still isn't selling.

Brennan Dunn 27:52
It was demoralizing as hell, honestly. I was like, What am I doing wrong? I'm doing the whole like, if you're supposed to do content marketing if you have a SaaS and I'm doing content marketing, but they don't want the SaaS what's wrong with this picture?

Jay Clouse 28:05
So you weren't you weren't just like, giddy like, Okay, I guess I'm doing digital products. Now you're like, why isn't this working? I wasn't, I'm gonna jump to this full force. Because this is working. It was why is

Brennan Dunn 28:14
I left the agency with some savings and the revenue from Saas in displace that the money I was, you know, burning, and it was more immediate revenue. To be honest, it was better than getting back into consulting. So, you know, that's what led me to do that. And my mind was blown, because I was doing like, I had this 20 person weekend workshop that I charged 1000 a head for. And I'd make you know, I'd bring in 20,000 a weekend. And the SaaS was doing like 2000 a month, at the time. You know, I mean, the the, the, the lazy programmer and me wanted the SaaS to just keep doing its thing, because I much preferred that kind of consistently recurring revenue model. But the pragmatist in me was thinking, well, this is doing kind of well.

Jay Clouse 29:03
So interesting people story around money that they'd be willing to pay $1,000 for a weekend workshop, but probably when they're looking at a pricing page that says, hey, this is $10 a month.

Brennan Dunn 29:12
Yeah, it's like, oh, it's expensive. Yeah.

Jay Clouse 29:14
It's it's so bizarre.

Brennan Dunn 29:16
Yeah, it is.

Jay Clouse 29:17
When we come back, Brennan, and I talk about how he's automated Double Your Freelancing to continue generating significant revenue without needing any attention whatsoever. And before we round out this conversation, we talked about his new software product, RightMessage that can help you to do the same. So stick around, and we'll be right back. Welcome back to my conversation with email marketing. extraordinare Brennan Dunn. Brennan had sold his SaaS company Planscope in 2015 and was focusing full time on Double Your Freelancing for the next two years. He had been digging deep into personalization on the Double Your Freelancing site and in 2017, a new opportunity for software emerged.

Brennan Dunn 29:57
I was doing twice annual conferences. And I was producing content and people were liking it and buying it. And it's all good. And well, and I think I did get bit by the SaaS bug, I think I just I kind of missed having software that I was selling, how it came about was anchor, the CEO of teachable, reached out to me and saw what I was doing, because we had known each other for a while. And he saw what I was doing with personalization on w freelancing. So where this came about was, people would come to like, my course sales pages, so w freelancing, right. And they would email me, or a few people I should say, would email me saying, Hey, I'm a copywriter I heard about your course looks good. But like all this, all the testimonials are from developers and designers, and it seems very developers, can this help me? In a reply saying, honestly, it's agnostic? Like I don't, none of it is specific to what kind of work you do, as long as you work for businesses. It took me a while, but I eventually realized that, you know, there's probably a lot of other people who thought that but didn't bother email me. So I thought, well, what if I could? What if I could ask people what kind of work to do? And then when the copywriter shows up on sales page, just do some if else was wizardry to just show the copywriter testimonials because I had them? So start doing that. And then I went beyond that because I would do things like I'd have an email course that would lead to that product, not ask people when they join the email course, what are they hoping the email course helps them achieve? Do they? Are they losing out on proposals? Do they want to start pressing on value? Are they just starting out with freelancing, they want to know how to price in general. And then what I would do is I change the pitch, they'd get emailed and the sales pitch that the pitch would lead them to, to reflect that core issue. And then sales started to go up a lot. So basically, I realized effectively that I was able to deliver a nice experience, which niche businesses always performed better than generic businesses for that niche, but without actually needing to niche anything. So I got really into that. Now, as it turned out all my developer ish tendencies. I did that for a few different, so I wasn't doing any consulting. But if you bigger companies reached out saying, we've seen your tweets, can you do something like that for us? So companies like Gumroad, and some others hired me to do a little small gig for them. And I did that a few times. And then Ankur reached out to teachable, saying, Hey, we want this but we wanted to software, can we raise around funding with a syndicate, and you can also get some other investors and we can make this a real thing.

Jay Clouse 32:32
So someone came to you and said, We want to help raise around to funding for software for you to build.

Brennan Dunn 32:38
Yeah, and they were kind of the majority investor. But we also raised some other money, we raised about 600,000. So it's not a ton, but it kind of helped us start, if that makes sense. Yeah, I partnered up with Shai, my co founder, he's a technical guy on the marketing salesperson, we built a SaaS. And the problem is we've we've realized that personalization is so brand new for a lot of people that we've completely are in the process of shifting, not pivoting, but shifting the focus of how we position the product. As a result.

Jay Clouse 33:12
How did you then now again, balance Well, now we have a SaaS product have a content product, the content product doesn't necessarily feed this SaaS product, the SaaS product could use its own content, how did you start managing your time in that world?

Brennan Dunn 33:25
I didn't take a salary from RightMessage for a while. And all my income came from automation on Double Your Freelancing. So I wanted to be in the position that if I never need to log into at the time it was stripped now converted. If I never needed to log in, convert it again, the business still works really well.

Jay Clouse 33:44
And to make this explicit, you're saying this is all automated through email mainly. So walk me through, like what types of automations are happening in email that is making this work, run, generate profit for you.

Brennan Dunn 33:57
So how I've designed it is at the point of Ingress. So when somebody opts in, I segment them I segment, about 80%- 85% of people on a confirmation page and two things of around, what kind of work they do, what stage their business is at what their goals are immediately, and so on. And then they get sent into a personalized email crash course that leads them to a paid product pitch that's evergreen, where they get a week long window just like a live launch, but for them where there's a discount attached. And, you know, the goal is to convert a lot of those people into early sales quickly. The majority of them won't buy so they get into a 52 week long evergreen chatter. I call it a shadow newsletter but evergreen newsletter, where back behind that newsletter is this bit of automation that I call an offer funnel where what it does is it looks at all that segment data along with what kind of articles you're reading and what you've bought already. And it basically calculates what should j buy next for me, right? So if you I think you should by mastering convert it. So it would set that on your record. Then every week in the newsletter that goes out like clockwork, every Thursday, there'll be a explicit personalized call to action in it, that would link you to that product. So the goal was to get myself written center weekly, and as soft promote a product, but then every quarter to do a live launch, which is just for you have that product that is recommended for you. Now, if you were to buy that product, subsequent emails and subsequent automated launches would then be based off of how the offer calc or the offer funnel re computes what you should buy next. So if you buy this, everything, you stop getting promoted that now you're getting promoted this. So it's basically just a giant Turing machine of things that are looking at inputs, what does Jay told us explicitly, along with how is J behaving, and then it's crunching what based off my own. I mean, I wish there was more machine learning involved, but it's not, it's just me thinking, if you fit this profile, and you haven't bought this, then you should buy this, and so on, and so forth. And that just, that just works because people don't care if the email that they're receiving today was written that morning by me or a year ago, as long as it's helpful for them.

Jay Clouse 36:07
If you're like me, this strategy of automation may be blowing your mind. And you might think that for Brennan to customize his emails for three different audiences, he would need to write three different variants of each type of email that he wanted to send. But actually, that's not the case. Instead, he uses a coding tool called liquid to personalize his messages within a single email.

Brennan Dunn 36:28
Some email marketing platforms, notably ConvertKit, and others utilize something called liquid templating, which allows you to inline add conditional content. So I would have a single email, but I might change the subject of it to say something like designers, Colin, here's what you need to raise your rates today. And I might include a sentence or a quick one liner testimonial, that would just be switched off of what kind of work they do. So here's a designer testimonial, here's a developer testimonial or something like that. And the goal there is just make it so the emails slightly more relevant to them, even though the majority of the content of the email is identical, but it helps open rates because they see themselves in the subject, they see an example. And this really shines in like pitch emails, not as much newsletters, but definitely pitch emails where you can really focus in on I know, this is the thing you're currently struggling with, because you've told me or you're on my website, and you're reading mostly articles about marketing. So I can infer you have a marketing issue. And I'm going to then focus the positioning of this product to be centered on either what you've told me or how you're behaving just like I would in person, like if, you know, if somebody comes to me at a conference, and they are like, Hey, I'm a web designer, I've heard about your course. I'm just starting out, do you think it's it's for me, I would absolutely tell her how I described the thing. With them in mind, I wouldn't talk about like agencies who have bought the course or anything like that. The same concept just done through conditional content, and it doesn't require fire is the mistake people make is because you can you can layer different things, you can say, I want to change this bit of email based off of their experience. And then that bit based off of the kind of work they do. If there's three experience levels, and five different types of work, you don't need 15 unique different pieces of email, you need a single email with some very easily written liquid conditional content.

Jay Clouse 38:16
And now all this is in Mastering ConvertKit. And now between Mastering ConvertKit and your new project Creat & Sell, I can tell that you're really focusing on creating excellent content for like the advanced email marketer or the aspirationally, advanced email marketer. So I'd love to talk a little bit more about that, because that is a hole that I've also seen, like, as someone who's trying to learn this stuff, all roads lead to Brennan, when I'm trying to learn these things. So how did you start to realize that you were in a position where people who were doing this type of work didn't have content that was really serving them?

Brennan Dunn 38:50
I mean, it makes sense why but I think like a lot of the content you find online about email marketing tends to be more to be one beginner focused, right. And I know, I know why it's that way. There's, there's volume reasons why it's that way. But I think just like if if everything when I was learning how to code if everything stopped it, how do you install Ruby? Or how do you you know, get a basic Hello, world app up? I yeah, I mean, it would be I wouldn't have advanced at all right. So I think what I'm trying to do with Create & Sell is to try to say others who have a real business that they are currently running where their products are offering, they're mostly doing their sales through email marketing, they have an audience, and you want to amplify this and you're ready to go beyond just the usual broadcast emails you sent out from time to time. And then like, Oh, it's my calendar says it's May 12. So I'm going to shut down the list for a week and do a live launch pitch thing. You want to get away from that and you want to focus more on automation and the angle that I'm trying to also take with great and sell is that automation doesn't nest usually mean it's, it's just for the person doing the automating, like I think there's this idea that if you if you've automated everything, you just sit on a beach somewhere with a Corona. And like, that's your end goal. It's like that whole like Lambo with the mansion passive income thing.

Tai Lopez 40:16
Here at my garage just bought this new Lamborghini here fun to drive up here in the Hollywood Hills.

Brennan Dunn 40:22
The argument I'm trying to make is that automation done right allows you to deliver the most relevant content to the right person at the right time. So if somebody is getting content that's more relevant to them, and more specific to their needs at their stage, and where they are, then they're more likely to keep reading your content, they're less likely to unsubscribe, they're more likely to really pay attention when you contact them, which the net effect of that is going to be more people are willing to buy from you. So my argument is that automation done right, personalization and right. And the underlying segmentation data, which is required for personalization, done, right, is going to lead for a more engaged email list. And I mean, obviously, you need good content, too, but more engaged email list, that translates into more revenue for us. So that's the whole long and short of what I'm trying to do with it is to say, if you can stop treating everyone identically, and just going in and saying, we're going to create a new broadcast and send it out to everyone, and the only personalization is sticking somebody's first name that they already know, at the top of the email, there's more we can do. And if we can do that, it's better for everyone involved.

Jay Clouse 41:29
It's clear to me, especially using tools like RightMessage, how you can do personalization in email. But we don't see this on like Instagram, like, will we ever see personalization? When I'm looking at videos on Instagram or videos on YouTube? Do you see it entering different mediums?

Brennan Dunn 41:45
I mean, it's there's there's macro personalization happening, where you're absolutely being served a timeline that is based off of previous consumption behavior on your part. But then on the micro side being the individual post, there's no personalization. That's one of the arguments I have for why email is better, is that it's truly one to one, rather than if I tweet right now on Twitter, it's one to many, and there's no permutations of my tweet at all. The yeah, so I don't know if it'll ever be I mean, it's hard to say because with the people, you know, the powers that be that control the different platforms like well, Twitter ever have conditional content, and how it How would that even work? I can see more on Facebook side, because they capture more information about you know, likes and dislikes, and Okay, I guess Twitter does, too. But I mean, the extent of it that I've seen used and I think, wasn't there some thing that hit the internet a few days back, where it was some someone that was kicked off of some platform, and they basically, were running ads that were saying, like, Instagram knows X, Y and Z about you or something. And all they were doing was doing layered targeting. So they were saying, here's an ad that says you like baseball, you live in New York, and you I don't know, like the color blue or something. You've told Facebook this because you put it in your profile somewhere. So they're running an ad saying, I'm going to target baseball, plus New York plus blue. And here's the ad creative that we're going to serve them. And Funny enough, that's, if you remember the Cambridge Analytica issue with the Trump campaign way back when that was the issue they were doing, which was literally, what is the thing you care about the most, you know, pro life taxes, whatever you tell the Trump campaign you care most about taxes, and suddenly, you're getting a lot of content about his tax stuff. That was the root of the issue. And I personally didn't see anything wrong with it. Because that's literally I think, what we're supposed to be telling, which is reacting to inputs that we're getting. But yeah, I mean, I think that that's the stuff that the extent of it, I think on social networks will be pretty much that being able to run very targeted ads based off demographic inputs,

Jay Clouse 43:56
You are creating this content that is like at the cutting edge of the top end, people are trying to do email marketing, that boundary will continuously move. So how are you thinking about? Will you continue to move with the cutting edge? Or will you continue to be in this void that you're finding now, which is like the next step after the beginner stuff?

Brennan Dunn 44:15
I hope so because I keep redoing constantly the course, the ConvertKit course, because I find, I think better ways of doing it, which is largely from customer interaction, right? So somebody will try something and they're like, Oh, I want to make it so you know, we can do this or that instead. And then we'll brainstorm of it and then we'll, we'll find a better way of doing it. Like I've actually I used to do all of my what are called glossier automations, which are ways of saying, given somebody inputs, how should I speak to them, right? So the end goal would be able to say, hey, as a blank as a design agency as a freelance developer as a freelance marketer, and just have that blank that gets auto populated with that where you're combining, are they solo or an agency and then what they do so that used to be done through a giant visual automation in ConvertKit. Now it's done through a single content snippet. So I've actually changed my whole thinking on that. So I'm, I think, what I love about the mastering ConvertKit specifically community as its 400 plus people who are kind of the upper echelon of people who are doing, really finding ways creative ways of breaking ConvertKit. And, you know, one, one perk of that, I think, is that we're helping, ultimately, hopefully building a better product and better email marketing platform. But we're also finding really new and creative ways to do what I was getting at, which is, how do we make it so we're able to stay individually relevant, even though this is a campaign that's going to hundreds of 1000s of people.

Jay Clouse 45:48
Brennan has built such an incredible set of businesses here and the way he utilizes personalization and automation to run Double Your Freelancing without putting much additional effort into it is so incredible, and just so aspirational. Believe me when I tell you that most passive income schemes are much much harder than guys like Tai Lopez and their garage are willing to tell you, but it's not impossible in Brendan's approach to using email marketing is a prime example of what is possible. If you want to follow along with Brennan, you can find him on twitter @BrennanDunn. I really recommend his new Create & Sell newsletter. And if you really want to go deeper in his incredible email marketing course, you can pick up Mastering ConvertKit links to both are in the show notes. Thanks to Brennan for being on the show. Thank you to Emily Clouse for making the artwork for this episode. Thanks to Nathan Todhunter for mixing the show and Brian Skeel for creating our music. If you liked this episode, you can tweet @JayClouse and let me know if you really want to say thank you. Please leave a review on Apple podcasts. Thanks for listening, and I'll talk to you next week.