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How to Grow Your List To 50,000 Subscribers with Brennan Dunn

November 6, 2023
The Recognized Authority Podcast Cover

The podcast that helps experts & consultants on the journey to becoming a recognized authority in your field, so you can increase your impact, command premium fees, work less hours, and never have to suffer a bad-fit client again!.

Tired of working every hour delivering custom services on hourly rates? Wish your subscribers felt more valued and engaged? Renowned online entrepreneur Brennan Dunn joins host Alastair McDermott to share his journey from agency work to selling digital products.

After building a successful consultancy, Brennan yearned for something scalable. He took a leap of faith, pivoting to content marketing and community engagement. Learn how Brennan attracted 50,000 subscribers without spending a penny on ads.

Brennan unlocked rapid growth through segmentation – by understanding subscriber needs, he created tailored content tracks that subscribers raved about. His audience insights also revealed promising new product ideas.

Tune in to discover:

  • The instability of reliance on a few big clients
  • Bootstrapping your audience with blogs and communities
  • Why most businesses fail at basic segmentation
  • Optimizing confirmation pages to learn about subscriber
  • Debunking the myth that you need absolute authority

If you’re struggling to engage subscribers, this episode is a must-listen. Brennan’s list-building and segmentation tactics will help you keep subscribers hooked and uncover hidden opportunities.

Show Notes

Key Insights

  • Agency work can be unstable with reliance on a few big clients
  • Built initial audience through blog content and community comments
  • Segmentation allows you to tailor messaging and content to different groups
  • Most small businesses just collect email, missing segmentation opportunity
  • You don’t need to be an absolute authority to share your knowledge


  • Get involved in relevant online communities and share your expertise
  • Use sales page surveys to segment and personalize subscriber experience
  • Send curated content tracks based on interests subscribers share
  • Partner with other newsletters for webinars to attract new subscribers


  • Write detailed answers in online communities linking to your content
  • On confirmation pages, ask short multiple choice questions to segment
  • For the first 3-4 months, send targeted content based on subscriber interests


Brandon Dunn: “I don’t like when content creators or people with newsletters send just sizzle content where it’s motivational, it’s a story, but if you want to get anything useful you have to buy something.” (Timestamp 17:58)

Brandon Dunn: “What most small businesses collect is just email addresses. They know nothing beyond that. Segmentation opens up product ideas and content opportunities.” (Timestamp 33:49)

Brandon Dunn: “There is no absolute authority. It’s all relative. I may know a little more than someone just starting out.” (Timestamp 43:12)

Alastair McDermott: “Our biggest competitor is usually not our actual competitors. It’s inaction.” (Timestamp 44:09)

Guest Bio



email, talk, started, book, content, building, week, opt, work, agency, clients, authority, write, courses, people, audience, creating, learned, freelancing, sell


Brennan Dunn, Voiceover, Alastair McDermott

Brennan Dunn 00:00

I’ve never seen being prolific about creating content hurt me in any way.

Voiceover 00:03

Welcome to The Recognized Authority, a podcast that helps specialized consultants and domain experts on your journey to become known as an authority in your field. Here’s your host, Alastair McDermott,

Alastair McDermott 00:15

I have a super episode for you today with Brennan Dunn. Before we get into that, I just want to briefly mention the Authority Bootcamp challenge. This is a paid challenge that I’m running in November, starting from this Thursday, the ninth of November, we’re going to run for four weeks until Thursday, December the seventh. And the goal is to lay down some foundational blocks of authority building an inbound lead generation before the year ends. And all of the work that we’re going to do together is actually going to be done on the calls. So you don’t need to commit any additional time apart from the calls that we’re going to be doing. So we’re going to be looking at positioning and LinkedIn optimization in week one, we’re going to be starting publishing in week two, if you want to publish in week one, that’s great. But we’re going to be working on that specifically in week two. And I’m going to show you some AI tools that can help with that as well. for week three, we’re going to do some more content creation. And we’re going to look at one of either video, or carousels.

Alastair McDermott 01:20

I’m actually going to cover both. And I’m gonna let you choose which of those you want to focus on. And then for week four, we’re going to focus more on distribution. So that’s getting your content. And again, you’re going to be creating content. during the bootcamp, we’re going to focus on week four, on not just the creation part, but also the distribution part. So we’re going to be doing that live weekly on Zoom, there’s going to be three zooms every week. One is the weekly kickoff, which is going to be led by me where I’m going to be walking you through what that week’s work is. And then there’s going to be two focus work sessions. And both of those work sessions, we’re going to be working live on the call, it would be great if you can make both of them. But ideally, you would attend at least one of those each week. And that’s where you actually do the work. So the way it works is I’m going to introduce and do a quick roundtable at the very start, we’re going to talk about what we’re going to be working on. And then we’re all going to hit mute. And we’re going to work away, we’re going to have a Pomodoro on screen. So I’m going to share that. So you can see a 25 minute timer, I can tell you’re going to work for 25 minutes, take a short break, and then work for another 25 minutes. So that’s what the focus work sessions are like.

Alastair McDermott 02:31

These are really great for making progress quickly. Because there’s a there’s an atmosphere of work in progress. There’s accountability. And also, it’s a time blocked on your calendar, just to focus on this. And the reason why this is so important is because the work that that we’re doing here, a building authority. It’s always important but never urgent. And because of that, it always gets dropped. And so what I’m trying to do is help you not to drop it, I’m trying to help you to make progress. I’m going to be doing q&a Every week in those weekly kickoff meetings. And I’m also going to be available depending on the the option that you choose, there is a VIP option that includes one to one as well. So you can learn more about this at the recognized Now on with the show. So today, my guest is Brendan Dunn. And Brendon is somebody who I’ve been following online for quite a long time. Because I just checked actually, it’s nearly eight years, Brandon, that I first opted into your email list, courtesy of Troy Dean, who’s another person in the kind of the web agency kind of space. So you’re very welcome to The Recognized Authority. Yeah,

Brennan Dunn 03:45

thanks, Alastair for having me.

Alastair McDermott 03:46

So I was gonna do the one line intro but you’ve done so many different things that it’s very hard to do that one line intro for you. You’re somebody I pay attention to. So I want to put that out there. First off. Right now you’re the founder of write message, the author of this is personal and you write weekly at create Ansel, a lot of people will know you if they’re they’ve been in my world through the W freelancing brand. And before that you had a project management software called plan scope. And you had an agency before that. I’m interested because what you told me before this in the pre pre show, was that when you were running the agency, you felt that you would like to have one of those businesses where you have lots and lots of customers and sell kind of cheaper, less expensive things to them. And it strikes me as really interesting because I have this conversation with people quite a lot. It’s always like, it seems like the grass is greener, whichever side of that divide you’re on. If you’re selling high ticket agency type, you kind of feel oh, it wouldn’t be nice to have kind of a smaller, smaller ticket low touch stuff. And then if you’re on the other side you think wouldn’t be nice to have less clients. What do you think about that?

Brennan Dunn 04:57

I mean, it’s funny, like we’re probably

Brennan Dunn 05:00

get to this point, I’ve actually come full circle. We didn’t talk about this pre show. But I’ve within over the summer I started a new agency. So I’m actually back to, to somewhat doing client work. But yeah, I mean, I think I think like a lot of people who are doing service work for clients get to the point like I did, where you have, no, you have a great client base, you have a waiting list, you have a great team, you’ve got all the right things in place. But then you realize that, okay, while I make great money, and while we have like, big, you know, we our average budget was six figure plus for most clients.

Brennan Dunn 05:35

If one of them pulled or if one of them, you know, walked away, that was that was, that was a shock to the system, even though yes, we had a waitlist, we could have, you know, knocked on doors, and so on and so forth and bump people up. I just, I hated kind of that, that game of like the wining and dining that needed to be done. The long drawn out sales cycle, the meetings that bring in like this, Matt and I had friends, a lot of what we were doing was building web applications for clients. So we were building MVP startups for people. And I had friends in that space, who were happily selling $20 A month subscription software. And they’re like, yeah, we’ve got a few 100 people paying us 20 bucks a month and, you know, carve out a great living work with a laptop in the cafe, don’t need to talk to anybody, unless they write into support. And that’s, that’s it. And the introverted engineer in me was like, that sounds good. Oh, yeah. So yeah, I actually that that’s that’s kind of what led me down the path of thinking, Could I safely exit the agency and kind of transition into software as a service? And that happened back in 2011. So can you

Alastair McDermott 06:50

tell me on the listener the difference or what the relationship was between the project management tool, the software as a service, and then the content side of the business, the Double Your Freelancing part? Can you can you tell me how those connected and how one grew from the other?

Brennan Dunn 07:07

Yeah, so annoyingly, we, you know, I say we, but largely me, along with some help from my team built this initial tool called plan scope. So we coded it, we did the marketing website, we built the app, and we’re very proud of it. But then I learned that I didn’t have a clue as to how to get people to actually buy it. So that was the thing I had to kind of learn firsthand. And the best practice at the time, and still largely is, was to go and create content. So have a blog, write content, and hopefully the right people. So in my world, agencies and freelancers would find that content, and then read it like it and get to the bottom and there’s a little banner ad or something that’s promoting our software, they click on it, they buy it and everything just works. So that was the kind of the operating model I went into for growing plant scope. That kind of works. But I think the mistake I made early on was thinking that if somebody goes to Google and types in how do I price a project, or how do I rate or proposal or how do I get my first client, that having a call to action, at the end of that article that links to a project management tool, is a bit of a disconnect. So that led me down the path of thinking, Okay, well, what if I can create other products that maybe can fund, if you will, the development of plan scope, and make us more money without needing to kind of try to fight over each and every new customer plan, scope, whatever, we could just sell courses and workshops and stuff that would kind of teach what I learned to building this agency. And maybe then finally, they’d still sign up for plan scope. But I could also make money doing that too. And that works well. And funny enough that the Irish connection here is the reason I wanted to do that was I wanted to go to a conference actually off of Galway on Inishmore. And it was this random little conference called Fun college. And at this time, because I put so much money into the development of plan scope, and I had gotten out of the agency, I didn’t have the money to just fly to Ireland for a week. So I actually pre sold a book to this budding email list and ebook called Double Your Freelancing rate, which would basically be everything I knew about how to price projects, and it kind of worked and I made money and I made enough money to book the plate and book the conference. And again, that’s how that’s how you’re a part of the world fits into my trajectory. running this business was that’s what got me into the if you what we used to call the info product world, which is now the crater world.

Alastair McDermott 09:50

That’s that’s class. I didn’t know that connection either. That’s hilarious. Yeah. Inishmore is the largest of the Iron Islands. It’s just off the west coast, not a million So way from where I live as well, it’s a nice part of the world to be in. I want a great place for conference.

Brennan Dunn 10:05

Yeah, it was beautiful. Yeah.

Alastair McDermott 10:07

So having been on both sides of that, and seeing, you know, the the agency world, and then the kind of the larger scale, kind of create a world where you’re creating content. And now going back to agency, like, what, what’s the what’s the big difference in an approach? Or like, how do you feel about that? Like, clearly, you’re going back to an agency again? So you know, there’s a reason for that. Can you tell me a little bit more about the decisions there?

Brennan Dunn 10:36

Yeah. So it’s, I wouldn’t say I’m going back to it, I would, I would phrase it as I’m adding a new offering to my lineup. So the way I look at it is for any, any problem domain. So in my world, that is the world of email marketing, and website personalization, and personalization, and so on, you have on one end of the spectrum, you have to put yourself first, you know, the people who want to buy a course they want to buy a book or something, they want to go through it, they want to apply what you teach in a generic way to their unique situation. On the other end of the spectrum, you have people who just say, I want to throw money at the problem, get it solved. And the agency or consulting world solves that kind of done for you way of tackling the problem. And then you have the do it yourself way, which is the you know, the course creation and in that sort of thing. So simply put, I wanted to cover the entire spectrum, I wanted to I have a very successful set of courses and products, and now a book that helps people on the do it yourself side. But then the people that hire highest echelon, the clients we’re working with now with this agency, who aren’t the sort of we’re gonna buy a course, you know, that they don’t want to do this themselves. They don’t want to learn it themselves. They don’t want to even equip their team internally to do it themselves. They just want to get me who I’ve taught them how to do this stuff, you know, in a way that is, you know, you talk a lot about authority building in a way that I’ve built up my own authority by teaching stuff for free publicly. I’ve entered on their radar, and they’ve said, okay, great, he has this course, I love the sales page and love it, or the course promises. But we don’t do the course, not only time sensitive, but it’s also a bit risky. We’d rather just get the person who teaches the course to help us even if it’s not me, it’s my team execute on on on their own problem. So that’s largely why I’m going back to it. It’s not because I’m retreating or anything to it, it’s because I’m trying to kind of complete the entire spectrum.

Alastair McDermott 12:29

Right? Yeah. So so it seems it seems to me that the the content creation on the courses and the information products that you’ve put a lot of time and effort into creating, now that they’re created, you don’t need to keep going back to those. So now you freed up some time to go, what am I on the right track with that

Brennan Dunn 12:49

you are and you always have the risk when somebody takes a course or say reads a book that they might enjoy what you teach and get a lot out of it, but they could botch up the execution of it. Whereas with this, we’re, we’re taking control over how we do things for our clients, which means we’re able to get some really incredible case studies. So we’re getting ridiculously good case studies that we can then use to bolster the broad appeal stuff. So getting people on our email list, getting people from the courses, and so on. So we’re looking at this as a way of not only being able to help a different kind of client, who is not a course taker, but also be able to really kind of strongly guarantee that the work we do will actually yield a financial ROI for them, which then we can then deploy as case studies. Again, like I just said, get people on our email list, everything just works out. And we’re already seeing that now where that kind of approach has been working really nicely for us. So

Alastair McDermott 13:49

one part of this that I’m really interested in is the part where you started creating content. And that content, I’m interested in that journey of content creation is something I talk to people a lot about it by demonstrating your knowledge, sharing your expertise in order to build authority, because I think that’s basically what we need to do. But I’m really interested in kind of where the line is for what we’re creating, publishing for free, versus what we should be putting into courses and charging for, or putting into, you know, books and things like that. How do you think about that? Yeah,

Brennan Dunn 14:21

so I um, I don’t like when content creators are excited people who are in newsletters or whatever else, just send sizzle content, where it’s just, you know, it’s motivational. It’s a story, but then if you want to really get anything that is actually useful you nearby something like I that’s completely counter to the approach I take my my approach is that, I want to make it so anytime I send an email, I’d say the email and it’s unright should be super valuable, so they should feel they finished the email that it was worth their time to read it. And it was worth their time to get an email from me All right. So my thinking is I want to give away my best stuff. The difference though is the way I present my paid courses is these are more systematic frameworks rather than like a random smorgasbord of content. So the way I look at my newsletter is every week, or actually twice a week, I’m sending out material, but there’s not a rhyme or reason. It’s, you know, this week, it might be about something that I’ve learned writing a book, The next week, it’s about something that I learned about, I don’t know, positioning or something, and so on, and so forth. But the way I present my courses, or my programs are, these are kind of curated, you know, start to finish systems that aren’t just training. So it’s includes resources, I, I’m a developer myself, so you know, I built like little mini tools that I bundle into my courses. That can be as simple as you know, worksheets that are included, video case studies, video tutorials, like walking through and showing how to use a an email system and do things with it. And even things like community or some degree of one on one access. So I think like, the big, the way I draw distinction is when you get something free from me, so say you’re on my newsletter, it’s going to be, it’s going to be random in the sense that it’s not going to be like I wouldn’t, I wouldn’t just deconstruct one of my paid courses and send it out over the span of four months or something to my list, it would be, you know, it’s going to be something kind of random, but it’s useful. And on top of that, there is no one on one expectation or anything given. If you want the one on one, whether it’s from me or somebody that works with me, that you pay more, you get more access to get more specific application of, of what I’m teaching, and so on. So yeah, I’m a big, I’m a big fan of just I don’t I don’t I try not to hide anything with the free stuff. I try to make it very, I want people to be thinking, if it’s free stuff, is this good? What’s what’s it going to be like if I buy the paid, paid thing? And that’s been my attitude? Yeah.

Alastair McDermott 17:03

And with the random emails, I think he used the word random, I’m not sure if he did. But that’s what I wrote down in my notes. If those emails are seemingly random, do you feel that the expectation for people on your email list is that like they’re okay with them with with these seemingly random topics? Or do you try and keep it fairly tight in terms of the topics that you cover? Because you mentioned something about publishing a book and one of them and you know, something totally different in it, you know? So what’s the pattern there? What’s the kind of the underlying theme?

Brennan Dunn 17:35

Yeah, I mean, they’re, they’re specific in the sense that my newsletter, for example, is all about helping people who sell digital products or coaching over email. So that’s kind of my that’s the, that’s the confines, if you will of my newsletter. So with the book thing, for example, I was talking about how I’m using email marketing with my own list to keep to try to make the book a perennial bestseller. So everything I do is centered on that. I do sometimes flirt with things kind of out of balance. So I talked about my the whole process that I had for getting a publisher, getting an agent, all that kind of stuff for the book, which technically has nothing to do with, you know, marketing, but the book is about email marketing. So I had to talk about kind of some of the questions my publisher had with like, hey, books supposed to be broad appeal, is this to niches is too technical, and how I went through thinking about that. And people were really receptive to that. So I think like when I’ve asked my list, because I’ve asked them actually before, like, do you mind when I go out of balance? Do you mind if I occasionally will talk about, you know, how I went about hiring an assistant or how I went about, you know, organizing an event, like a workshop or something? I think there’s enough overlap with my audience where, because they’re all selling, say, digital products, the idea of like, Oh, here’s how you got a book deal, or here’s how he organized it in person workshop. Like, there’s still enough interest, even though it doesn’t directly align with like, email marketing as a topic, but I tend to stick to just all things email. Yeah.

Alastair McDermott 19:08

Yeah, cool. Um, you know, I feel you on that, like, I talk about how to build authority, and all the related things. And under so much related, like, we could talk about how you can use a book to build authority to use podcast, email marketing, AI, for example. And I’m actually going to splinter off the AI discussion, because I feel like I’m talking about a little bit too much on this podcast, I’m actually gonna Splinter it off into its own thing. And then, like, I actually talked about what you just talked about how to hire a VA. I posted about that recently on my blog, because a few people were asking me about that. And I wanted to kind of give them step by step instructions. I feel like that’s all interrelated and it’s all it for me, that’s all tightly aligned. But I can understand how somebody looking at that is thinking, you know, this, this seems to be different or random as he as he said, so that’s something I’ve been thinking about myself. I think

Brennan Dunn 19:57

just to go back to the to the random thing, I think what I really meant by that was that there’s no like, let’s say for the next three months I’m I’m talking about nonstop things you can do with email marketing. But it’s not necessarily that today’s email builds on last week’s email, which builds on the previous week’s email. Whereas the course I would expect that kind of progression. Yeah, yeah.

Alastair McDermott 20:18

It’s, it’s, it’s, it’s kind of more episodic rather than serial. Correct? Yeah. Yeah. Yeah. Yeah. And I wasn’t picking on you using the word random, but just it’s it’s something that I think about myself for myself, and and I feel like, I can come across that way as well. With that kind of episodic jumping from one thing to another. But yeah, so I think I think the the, I think that the building the audience and growing like you told me, I think you had 50,000 subscribers and 10,000 customers. For for W freelancing. Yeah. Yeah. Yeah, that’s, that’s pretty cool. Can you tell me a little bit about that? Like, when you started, like, did you start from zero with that? Or were you able to populate that, you know, with with some of your agency? I mean, I assume that most of those were not agency clients right? Now.

Brennan Dunn 21:09

Now. It’s it started truly from zero. What my so early on, I kind of did the standard, write blog posts, have an opt in form, publish the void kind of model. What I ended up doing that worked pretty well was to go and get involved in online communities, like at the time it was, there was Reddit had a freelancing subreddit, there were there was Hacker News, which didn’t, it wasn’t exactly 100% freelancers, but a lot of that a lot of people there were. And what I would do is I would get involved in discussions, and then I would find ways of cleverly linking to a blog post I happen to have on the topic in a way that didn’t seem like, like a bot did it right. So I would actually get involved. You know, I write like a lengthy comment reply. And this stuff did not scale, but it helps see the list. I’d really like to reply, and then just link to my, you know, the article that I had on it. And I actually ended up getting the point where I was like, Oh, well, I’ve got like a nice portfolio of content that I can just use whenever. So if somebody’s like, Hey, what are your thoughts on? What do I do when I get a new lead? Like, what what should I be doing? And initially, I was like, oh, good content from that. Now, I just pointed out instead of saying the same thing again, and again and again. And then so I started that way. And eventually, because it was kind of early, this is 2011 2012. I did really well, I was I’m not an SEO person. But I somehow did well with like Google search. And I started to get a good amount of traffic from Google, which is helping a bit. And then what really helped was I started doing partner webinars. So I did events with companies like woo themes with 99, new with bid sketch and stuff. And again, this was back 2012 ish. So it was, while people on the internet marketing side of things, I think we’re doing this, I didn’t ever consider myself to be an internet marketer, and like sales page kind of way of looking at it. But I started doing kind of these workshops, where I’d say to like, roofings, hey, I’d love to do this thing. And this is after I created my course, I had created that that ebook. I mentioned the W freelancing rate ebook. And I basically went to like a road show, if you will, trying to sell that ebook. And I’d go to themes and say, Hey, most of your customers or freelancers or agency owners, at this book, that’s kind of a primer on how to price, I’d love to do a thing like a joint venture thing, you get half I get half of any revenue that we make from the workshop, workshop itself will be super valuable, I’m going to do a soft pitch at the end, but it won’t be like a, like just a bunch of like stuff. And then oh, if you really want to get the secrets, you need to buy the book. And that did well. And I ended up getting in one summer alone about 15,000 subscribers to my list. Just remember that because what I would do is I’d root themes or whoever would email their list to my landing page. We got the opt ins, we’d have you know, 15 20% of people who opted in actually attend live if we were lucky. And But needless to say, 100% of everyone who opted in ended up on my list. Now, they weren’t always the highest quality there. It’s not like somebody who went to a blog post and read it and loved it and then opted in. But it ended up kind of growing list pretty quickly. And then from there, that kind of compounded things because I started getting more word of mouth and I started getting people back linking to the site and then it just started to grow and grow without me being ever I hate saying this, but like I was really really never that intentional about like link building or SEO or anything. It just kind of happened. And yeah, that that eventually got it to where it ended up being or it’s now bigger than 50,000. But

Alastair McDermott 24:58

yeah, that’s that’s pretty cool. So zero to 50,000. And if you were to do it now, do you think that you would do it the same way, if you have to now there,

Brennan Dunn 25:06

there are different tools now that I’d probably be looking at. So there’s tools like on, on ConvertKit, there’s the Creator network on there’s tool called spark loop, which allows you to kind of partner with other newsletters or pay for subscribers on a cost per action basis. I never actually paid I never ran ads. I tried running ads for about two weeks until you’re freelancing, but I had no idea what I was doing. So I turned it off. But I outside of that, I never really paid for subscribers. And I think if I was doing it today, with a new business like that, I’d probably be doing not only that, but I’d be doing probably not as much on the on a like written content side. But maybe more on like YouTube or other platforms that have good distribution. I never really did anything with social back then. Because again, in 2012, people were using Twitter to talk about like, sitting on the toilet, like no one was using it to like promote their business and stuff. So there’s pretty much all search from Google.

Alastair McDermott 26:05

And it’s come kind of full circle now to the really.

Brennan Dunn 26:08

Exactly, exactly.

Alastair McDermott 26:11

So, okay, let’s let’s segue into segmentation, then. And can you tell me a little bit about why that’s important and how that relates to what you talked about already?

Brennan Dunn 26:24

Yeah, so I think what’s most important to me and kind of a experiment or experiment, but the the thing I’ve been kind of exploring for the last six years, has been so back when I was selling consulting work, I used to really enjoy the fact that if I, if I’m in a room with somebody, or if I want a phone call with them, and they come off as being pretty tactical, maybe they’ve done this kind of thing, before they’re in, you know, retail, or some industry or something like that, I used to really enjoy knowing that I could kind of take the core thing that I say to most people, and change it up, depending on who I was talking with. So if they’re technical, I’ll speak more technical to them. If they if they don’t care at all about the tech, they just want like a web app, maybe they don’t even know what a web app is, they want a web site where you can do stuff, then I would speak less technical to them. And you know, I think anyone who’s done high touch sales, we know that we’re not just parroting a script, we’re kind of modifying what we say, based on what we’re hearing what we know about somebody, and so on. So we’re how this applies to what I’m doing today. When I was doing W freelancing, our main product, the book evolved in a course called W freelancing. Right? So started, I was about to turn into a full blown course. The sales page had testimonials. It was kind of a standard kind of core sales page with like, here’s what’s included. Here’s testimonials. FAQ is right for you, all that kind of stuff. And I remember getting an email from somebody who was a copywriter. And she wrote in asking if the course is right for her, she had heard good things about it. But looking at the sales page, it’s all developers desires, as the testimonials and stuff. And again, that comes from when I started out on Hacker News was mostly developers and designers who, who found my stuff initially. So I was able to kind of talk to her over email and let her know, hey, the courses agnostic about what it is you technically do. It’s, of course, and how to how to sell yourself to a new client, and how to price your work. So I was able to salvage the sale, but it got me thinking, how many other people had that same concern that they didn’t see themselves in the product and close tabs, but didn’t email me? So that’s when I started thinking I put on my developer hat and thought, well, you know, when I’m on Facebook, it’s a webpage according to my web browser. But I’m seeing my stuff, I’m seeing my friends. And when I’m on a sales page like mine, again, it’s just a different web page. But I’m seeing everyone’s seeing the same thing. And I thought, well, what if I could find how if I could somehow know that this person was a copywriter? Could I maybe change the testimonials on the page to be copywriters, and use language that is more copywriter ish? And that’s what I started to do was just thinking, Okay, well, I’m a developer, I can like, write some if else conditions and say if they’re a copywriter, because they’ve told me through a survey, then show the copywriter language that their developers show the developer language and so on. So started doing that. And then it started to really work well, and that’s the segmentation angle is like, you can’t do that you can’t show more personal more relevant content unless you have segment data under that. So I, I went down this path started working well. I got on the radar of a few bigger companies who had a lot more skin in the game, notably being teachable. And their founder anchor reached out to me and said, hey, what if you stop screwing around with this shit on your own for your own stuff? And can we just throw you a lot of money and you make this a proper product, what you’re doing on your on your stupid little freelancing site? it because this would be huge like this, this needs to be done. So we hit up raising around a funding, led by anchor and along with about 10 other investors hired a team and build up this product that just took the manual code that I’d written and made it a self serve tool that a marketer could use. Because the issue I had was, I did try to make this a product that code I was doing for W freelancing, a product that involves downloading a zip file, and taking a bunch of JavaScript and saying, here’s a little written text file on how to use it. When you get that to the standard, like the average marketer, they’re gonna be like, What the hell is it? So that didn’t work that well. But again, it eventually led to deciding let’s let’s make this a tool. Let’s get back into software game, I’d, I’d sold plan scope, but let’s try it a new one. And that this has done much better than planned scope. obraz.

Alastair McDermott 30:58

Awesome. And so tell me then a little bit about if somebody is starting out, and you know, I’ve got an email list of just under 500. So it’s not zero, but you know, it’s not 50,000, either. Is segmentation important, a kind of smaller scale. Or

Brennan Dunn 31:17

it is, because even if you don’t plan on doing anything with it yet, I’m always thinking, like, it’s great that you have 505,000 50,000 people, and a lot of people, that’s what that’s what they say is they’ve got like, they’ve got a newsletter, they’ve got 500 people out. But if you were to ask people to say, Well, tell me about the composition in that list. Like, why are they there? Why, why did they join? Who are they and who could change depending on what kind of newsletter or audience you have. But if you can know that, like so, what what we usually help people do and what we’ve been helping people to do is to say, look, when somebody joins your list, you usually capture first name and email address. And that’s all you have about them, like, you know, nothing beyond that. What if you could find out a bit about why they joined and what their expectations are with you, and a bit about who they are in a way that is, serves them. So it’s not just for your own purposes, what if we could say, we want to better serve you. So for us to do that, we have a quick multiple choice survey that you just show on your confirmation page. And that data then would then get synced up to their record. So it’s not just aggregate data, but it would also get attached individually to like Brendan’s record. He’s this, he’s joined for this reason, and so on. So I think like, even if you’re just starting out, I think it’s useful to have that information. I mean, we’ve, I’ve talked to plenty of companies who, when they have relatively smaller audiences, they, they’re still doing this. And it’s giving them directional ideas about what products should we create? What are the things that we can’t infer just purely on open rates, or click rates or Google Analytics data, which gets geographic data and so on? Like, what if we can know that 40% of our audience struggles with this problem, and 20% struggles with that problem. Maybe this indicates, you know, potential products that you could be creating, or, you know, the type of people who resonate best with your content, so you can go get more of them. And there’s just a ton of applications that you can use with this, like, big thing, too, that is under utilized is when you start to segment out your audience, you can then superimpose it on your reporting, and say, not just how much money did we made? Or did we make or what is the value of a customer or the value of a subscriber? But how does somebody who don’t know is is a designer? What are they worth relative to somebody who’s a copywriter, and when you when you start to have that information, you can do so many incredible things. But it’s so rare that I think anyone out of the enterprise actually does stuff like that they go beyond anything beyond their email address, and maybe tagging them at the live from you or something like that.

Alastair McDermott 33:57

So let’s say I was to do this. And, by the way, I have done a little bit uncensored, I have used ConvertKit, where I’ve sent out surveys, I guess, probably every six months or so when I ask people to click on a link and I tagged them with an interest. And I do that every so often, just to see, you know, one of the topics and I did this recently and give it a whole bunch of different topics. And the top three that people were interested in listened to on this on my email list are building authority, obviously, generating leads, and the reason why we want to build authority is typically to generate leads. And then I was interested that AI using using AI was actually third. But I also think that there are people out there on this, listen to this podcast who think that I covered that a little bit too much. Because I have like I’d say I’ve covered in maybe four of the last eight episodes have mentioned AI to some significant degree. So and I don’t want to like I don’t want this to be the AI podcast. I will make another one for that. But like is that the kind of thing you’re talking about? Are Can you tell me like where do I go next? Like where would you go if that was your you were talking to somebody or give Then advice, but like, what will be the next step?

Brennan Dunn 35:02

I mean, you can do it through LinkedIn email. That’s kind of the the easy way of doing it. The only downside is, it’s cumbersome to ask more than one thing. Right? You’re probably asking them, like you said, which which, which are you most interested in? Click one of the following. Usually, I think when you’ve got somebody’s attention, like so we have internal data that shows if somebody answers one question, the likelihood of them answering questions 234, and five, are 97% Plus, so if they answer that first one, might as well use is to ask either a follow up question that relates to what they chose. So let’s say they chose, you know, they want to they want to, they’re interested in what you have to say, because they want to, you know, generate more leads or something. So then you can ask them a bit about, okay, tell me about your business, are you, you know, is this something you’re gonna decide, is it a full time thing, you have a team, and you can kind of drill a bit deeper to get add more context and color to their situation. And it’s just different, you can’t really have a single email that asks multiple questions you just kind of falls apart. So what I usually recommend, as the best thing to do would be when somebody is most excited, that’s around when they opt in to your email list. They buy from you they do, there’s some like, transaction that occurs, right. And usually, most confirmation pages post opt in are like thanks, check your email, which to be honest, is kind of lame. So what we recommend people doing is change that to say, hey, you know, welcome, I want to make sure I get you exactly what you need. I’ve got a quick 15/22 survey. And it’s all multiple choice, none of this fill in the blank stuff. And you just rapid fire, ask people questions. And then what we’re seeing response right wise is usually 80 to 85% of all new subscribers, when when when the questions are phrased correctly, when they’re saying they’re not too prying, and so on. 80 to 85% of all new subscribers will be segmented which the average for a, and I’d love to hear your stats on this if you have them. But the average for when you send an email to your list with links, it’s less than 30% Typically, will actually engage with that, and do it. So you have higher coverage. And at that point, they’re they’re excited. They’re just literally said, I give you permission to email me. So at that point in time, if you can say, Great, I want to make sure you get the right emails from us. How can I best serve you? Why your Why are you here? What do you need from, you know, for me or from us? That’s a great time to to ask that information. And that’s usually what we recommend people do.

Alastair McDermott 37:40

Yeah, that’s really cool. And, you know, you’re I think you’re right there. Like I just checked to see what the stats were on that I had a 48% open rate on that email, which is kind of the average for my list is 45 to 50. So that’s pretty, pretty high, I think, decent. And then the click rate on that was 5.1%. So so the actual, the number of people are actually watching this. Yeah, yeah. So yeah, it’s, it’s, it’s pretty, like it is hard to get people and I think that now some of that may be because, like, whenever I think about open rate, I always think this is the reported open rate, it’s not necessarily the actual open rate. Because you know, there’s a lot of privacy tools that are not not allowing you to know what’s happening there. Which I, which I fully agree with, like that. That’s good. But then, you know, like, I don’t know, what the, like, what the, the, the what is it that we can do to get people to take more action on these things? Like, I think, for me, like if anybody’s listening to this, and this thinking like 45%, open rate, that’s actually pretty good. Like, that’s, that’s quite a strong open rate, you know, by industry standards. And so I’m very happy with that. But then to see a click rate of 5% is super low. I’m kind of disappointed that it’s that low, considering how many people are actually looking at that email. So I don’t know how to square that circle. I don’t know how to fix that to bridge that gap.

Brennan Dunn 39:07

Yeah, I mean, a lot of it just depends on how you position the question. Is there anything that it’s kind of like when I get I get NPS survey emails all the time from brands, like when I go on a flight? You know, a few days later, I’m gonna get a survey from the flight, how do we do or something like that? But there’s never anything baked into the question that benefits me in any way. I mean, you could do the cheap thing and say, hey, you know, tell me how you did on the flight. We’ll give you 1000 There miles or something, your account. But I think the more important thing would be if the question can be posed as we want to make sure that you get exactly what you need, and nothing more. And this is where personalization comes in. So one of the things I do is when somebody joins my list, and they share with me, there’s one of three core reasons why somebody would join, they want help building an audience, they want to help automating their marketing, or they want help with selling more so they want to turn more subscribers into customers. So when you choose one of those and again I’m getting it on 85% of all new people joining my list segmenting themselves. So they’re answering that question. When you choose one of those, I have a secondary, non live, Evergreen newsletter that goes out. And it’s curated. So if you choose that your focus is on audience growth every Tuesday for three to four months, you’re gonna get an email that’s dialed in on just what I’ve had to say about audience growth over the years view answered automation, for the first four months, just what I have to say about automation and an order that I think makes sense. So I still send out those random emails on Thursday, the live emails, but on Tuesday, they’re getting a curated tract of content that aligns with what they shared with me. Now make it very clear when they opt in with a welcome sequence that you shared with me that you want to help coordinate your audience with email or building your email list and growing your audience. Here’s my plan to help you for the next few months, I’m gonna be sending you every Tuesday emails about nothing about audience growth. And you also shared with me that use ConvertKit. I also use ConvertKit. I’m going to also include in these emails, tips that you can apply directly to your ConvertKit account. People get that and they’re like, holy crap, like this guy’s this is like, and I’ve had replies from people saying, first off, that’s kind of cool. But they’ve also said like, they really like the fact that it’s obvious that I’m listening even if even if it’s an individual listening, like I’m not there like wizard, Wizard of Oz style man behind the curtain, like saying, oh, Alastair opted in, he said, this, I’m gonna push in here. I mean, it’s automated at this point. But I think the fact that I’m saying, I’m listening, the fact that you want to help with automation, so I’m going to deliver you a track of content that is dialed in automation, because that’s what you need help with. And that that I think, goes a long way. And, again, it’s because I positioned the question as if you give me if you help me out, I can, I can serve you better. So

Alastair McDermott 41:51

and I’m gonna go check that out. That’s at Creighton Right? Yes. Yeah. Cool. I’m just gonna put that up on the on the screen here as well.

Brennan Dunn 41:59

So you’ll see it when you opt in how it works.

Alastair McDermott 42:05

Email here, so cool. I’m just gonna put that up on screen for everybody. Yeah, so Okay, so I’m just aware of time, we got to wrap it up. There are some questions, you know, that I always ask my audience, one of those is about building authority. What is the number one tip that you would give to somebody who wants to build their authority?

Brennan Dunn 42:28

I think the big thing is, so what’s helped me is, I mean, the obvious answers create a lot of content and make it public. But I think the the thing that I think sets a lot of people, or keeps them from starting is this idea that they need to be an absolute authority. I learned firsthand that I learned a lot better from somebody just a few steps ahead of me than somebody who is academic ivory tower. It’s been ages since they’ve actually been in my shoes kind of thing. So I think like a lot of people, which makes sense, think like, oh, there are so many spaces so saturated, there’s already people say talking about, you know, marketing or whatever else. Who am I like, who am I to actually throw my hat in the ring and be another voice be more noise. But I think when you realize that there is no absolute authority, there’s no like, show me a list of all the authorities in the you know, marketing space, there’s no, there’s no database for that. Instead, it’s all relative, it’s, you know, I’ve helped this person and say in my hometown, get their email system set up and running to them. I am the authority. They don’t know about anyone else out there. And I think when I first learned this was with plan scope, when I would ask people about what are the other project management tools you’re using? And because I knew the competitive landscape, I knew my competitors, and a lot of people replied saying like, like, there are other tools and stuff, you know, such think like, I wouldn’t worry too much about the imposter syndrome that comes with, am I am I just gonna be more noise? Because I know that’s something I’ve struggled with and to degree still struggle with.

Alastair McDermott 44:08

Yeah, I always think, you know, our biggest competitor is usually not our actual competitors, our biggest competitor, this usually in action. So, yeah. The one thing I just want to ask you, and by the way, do you have a hard stop? Are you able to go two or three minutes? Okay, so just before I dig into this a little bit, you said, create a lot of content and make it public. And I know that there are other people out there who kind of resist the idea of even advising people to make lots of content. Now, obviously, I suppose that idea because that’s what I’m doing right here. You know, I’ve got this, this will probably be episode 141 142 of this podcast. So, you know, I truly believe in creating a lot of content and writing books and publishing, but there’s a lot of people kind of feel, you know, I don’t have time to do that. What like, why would I want to do that? It feels like you know, it’s it’s so much effort. Can you just speak to That little bit about how you feel about that.

Brennan Dunn 45:02

I mean, I think Okay, so let’s quickly talk about the consulting room, because I assume a lot of people are, is it true that a lot of your audience is probably still doing like stone services? Or

Alastair McDermott 45:10

yeah, yeah. So independent consultants, experts in their field, people like that. So

Brennan Dunn 45:15

when I hire consultants, myself, I want to see a track record that goes beyond any flashy marketing website that they have. I always really enjoy being able to say, oh, like, here’s, like, I one thing that I’ve always appreciated is when I can see somebody who they talk publicly about the interactions they have with their clients, you know, maybe questions that come up with with a potential client, who, you know, the example I always give is, we had when I had the agency, we had a client who wanted to build a smuggling, social network type thing. And we were like, well, don’t don’t start with the social stuff. Start with like, the core unique thing that you’re going to build. And we ended up just talking a lot about it. Because we had, we did a lot of local events for office, and we did a whole workshop on why you should start with your unique value prop rather than, you know, tacking on social stuff. And I think that’s the kind of thing that if you can, if you can say like, here’s my thought process about why I responded to this new project lead and this way, and other people can look at that and say, Well, I like the way that this person thinks I like that the way that they do business. I think it can only help one year not just putting this wall of your marketing site between you and the world where you actually have where you expose, like, here’s, you know, here’s something we learned on this client project. Here’s, we know, we tried out this new way of doing things and it worked really well. And, and here’s what you know, what worked, what didn’t work, and so on. I think that’s because eventually you get to the point where you have new project leads, and you can just drop links this content. Like it, I think it makes you so much more authoritative. When you’re like, Hey, I’ve actually written a 2000 word article on it. Here we go. Or something like that, rather than needing to rehash everything kind of on the spot, but again, I I’ve never seen being prolific about creating content hurt me in any way.

Alastair McDermott 47:15

Yeah, yeah. Okay. Well, I mean, I simply agree with you. But I know that there is the there is the fear of we’re making too much content, or, you know, it’s something I’ve just spoken with, and published an episode with another guy, Steven Lewis, about the type of content that we should be creating. But I don’t want to dive into that, because we’re coming up on time. And thank you so much for taking the extra couple minutes. Speaking of things that maybe didn’t work, can, can you tell me if Is there a business mistake or failure that you’ve experienced that you can tell us about? What you learned from it?

Brennan Dunn 47:49

I think with so yeah, I think so. With the, with the W freelancing thing, I think I made the mistake of as it was growing a bit off more than I can chew. So I mentioned that I had conferences that I ran, I also tried to run like worldwide meetup groups, because I figured, look, I’m there. I’m the circus leader of this group of 50,000, freelancers, and agencies, there’s a one to many relationship with me. And then how can I create many, many, how can I because I knew that if you get smart people to room together, if I organize that, naturally, they’ll mingle and then partnerships, we forge or, you know, we’ll get a ton out of that. so on. So I think the mistake that I made when I looked back at that business was I didn’t focus enough on the things that were working, I tried to diversify, by having like, you know, doing multiple podcasts and doing events and doing this. And it was really just me. So eventually got to the point where I started seeing kind of, I was spreading myself, myself way too thin. And it did it did affect the core business. So I think like, there’s something to be said, I’m trying to be a lot better at this now about just focus and seeing what’s working. And doing more of that, rather than trying to do all this. Because I have shiny object syndrome. I see people doing this on LinkedIn, and people doing that on Twitter, and people doing this over here. And I’m like, I should do all that too. But yeah, I’ve come to realize

Alastair McDermott 49:23

that’s the problem with the kind of the engineer, creator type mindset. Yeah, where you can do all the things and that’s the that’s, that’s the hard part. Is there a business book or resource that’s been important for you, or that you’d recommend?

Brennan Dunn 49:37

Yeah, all my books are on my bedside table. Now at the minute I’m finally reading April Dunford, obviously awesome, which is a book on product position, which to be fair, or to be frank is something I’m struggling with at the minute with right passage, because we’ve kind of shifted and pivoted a bit. So it’s a really great book on just kind of how do you contextualize your product or service in a way that the customers You want to have will relate to, and it’s brilliant book on kind of going beyond the usual position statement and coming up with a really good way of contextualized in your business. It’s very jobs to be done, if that resonates with anyone listening. Yeah,

Alastair McDermott 50:15

awesome. And final question is do you read any fiction at all? Is there anything that you live in?

Brennan Dunn 50:20

I did read a lot of fiction. I’m in the middle of Ken Follett, who is one of my favorite authors just released a new book. I forgot the name. It’s part of the Kingsbridge series, but it’s certainly 18th century. So I read a lot of historical fiction, a lot of World War Two historical fiction, and a lot of like, medieval stuff. I don’t read a lot of fantasy or or anything like that, but I do a lot of historical fiction. Awesome.

Alastair McDermott 50:46

I just like to get get a flavor for people like Brennan, where can people find you if they want to learn more and I have Creighton On the screen here as well. So

Brennan Dunn 50:55

Creighton Soto Axio if you want to get in my head, my book, this is first of all, just was released a week ago. And that’s it. This is personal It’s available on Amazon, all the usual places. And yeah, other than that, there’s right message comm or find me on Twitter, Brennan, Dutton Bjarni and an en un. Awesome,

Alastair McDermott 51:18

brown done. Thank you so much for coming on the show. Thanks. So thanks for tuning in. Don’t forget to check out the authority bootcamp at the recognized camp, if you want some help and support in building authority and getting a win on the board in terms of content creation before the new year. Thanks again. See you next time. Bye.