Run an automated newsletter business with Brennan Dunn

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Writing a newsletter and hitting send every week? You might be missing out.

With 11 years of experience in building automated newsletter businesses, Brennan Dunn shares his strategies through his newsletter Create & Sell. In this episode of Creators on Air, Brennan joins us to discuss:

  • audience segmentation
  • personalised experiences
  • automated sequences
  • lead magnets
  • and much more

Brennan Dunn has helped countless businesses bridge the gap between their offerings and audience engagement. With his course ‘Mastering Convertkit’ and 11 years of experience in building automated personalisation for newsletters, he now shares his strategies with creators through his newsletter Create & Sell.

In this episode of Creators on Air, Brennan Dunn, founder of RightMessage, joins us to discuss newsletter growth, audience segmentation and the importance of personalised communication.

Follow Brennan:

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Episode Transcript

Akta: [00:00:00] When you send out an email to your subscribers, do you know who you're actually sending it to? Are they gettingthe right message and are there pain points actually being addressed?

Brennan: I would justreally try to find like the brand that has the features you want along with youseeing yourself in the audience.

Akta: Brennan Dunn isthe founder of Write Message and he writes a newsletter, create and Sell, andhe'll make you think about newsletters in a completely new way. In this episodeof Create and Air, Brennan shares how to personalize your messaging, segmentyour audience, and build a scalable automated newsletter business.

So most of the time, or early on, I should say it waspredominantly word of mouth along with uh, spark Loop. Referrals. So I had areferral scheme that I had, uh, set up with the newsletter, and that did fairlywell. The thing about the Create and Sell newsletter is unlike my previousbusiness, which was Double Your Freelancing, which that is a list of 50,000freelancers, that [00:01:00] was all donethrough search.

So all of the growth over the last decade for that list, ahundred percent due to people going to Google and typing a question, finding ablog post, and then opting in, create and Sell, never got that lucky. We reallynever. Cracked the uh, or we still haven't yet cracked the search nugget, Iguess so. Um, Early on it was word of mouth, and then it was the referralscheme.

And over the last six months, really I've been doing, um, I'vebeen buying, uh, through Spark Loop's partner program, uh, the ability where Ican partner up with other creators. And what I had set up with that isbasically just a pay per referral kind of thing. Um, so if you're familiar withlike the creator network that ConvertKit just rolled out, it's, it's similar tothat.

But this was before that existed, so I'm actually migrating nowto, um, To the Creator network, uh, now, so, yeah.

And what about things like lead magnets? Because some, that'ssomething I see in, um, email marketing especially quite a lot. Is thatsomething that's important to [00:02:00] have?

Brennan: Yeah, Imean, yeah. So typically a lead magnet is any sort of incentive to get somebodyon an email list, right?

And with Crate and Sell. To this day, it's still just ageneric. Newsletter opt-in with Create and Sell At the minute. There's a bit ofa Cobbler Shoes problem in that my lead magnet is still just a newsletteropt-in, and that's doing well enough. I mean, it's working, but the thing thatreally grew my other brand W Freelancing was an email course.

So I'm really bullish on email courses is a way of gettingsomebody onto your list, getting them familiar with who you are, what youteach, what you're good at, and ideally even pitching them on a paid offering.So, um, yeah, I'm, I'm very, I'm a big fan of email courses. I just haven't hadthe time with all the things I, I have going on, uh, to really build one forCreate and Sell just yet.

Akta: And if you didgo about making something for Create and Sell, what do you think would make itenticing enough as a lead magnet for the newsletter itself?

Brennan: So itreally, the, the simple answer is it depends [00:03:00]because one thing that I do that I'm pretty good at at this point is audiencesegmentation. So when you join, create and Sell's email list, and you opt in onthe confirmation page, instead of it saying, go and check your email, and clickthe confirm link it instead.

Runs people through a segmentation survey where I ask themspecifically, why did they join the email list? What email platform do theyuse? How experienced are they with it? And so on and so forth. And the goodthing about that is that that's actually 85% of all people who opt in completethat, which means I'm not just getting a first name and an email address.

I get. Their, you know, biggest pain point, their emailplatform and all that kind of stuff. So what I'm doing at the minute is I amsending people through a personalized onboarding sequence, which at the minuteis kind of my email course equivalent. It's not as intentional. It's not asmuch like an asset as a proper email course, but I'm segmenting people andpersonalizing that welcome.

Experience for them. And then I'm putting people on anautomated newsletter that is also [00:04:00]based on their segmentation. So what I would do would be given, if somebodyjoins my list and they say, I am looking for help with audience growth, thenI'd wanna put them through an intentional email course on audience growth.

Whereas somebody who says, I'm looking to turn more subscribersinto customers, they would get a different sequence. So like I have an emailcourse with right message. That's our main way of getting people under ourlist. We do exactly that. So we find out what are their, what's their currentchallenge, and really we ask similar questions and then we run them through anine day email course.

That's really kind of a crash course on how do you segment youraudience, how do you then use what you learn to then deliver more relevantexperiences through personalization. It's all hyper-personalized based on thedata that they give us. So one day I'll do that for print and sell. You're

Akta: actually askingall the questions that I want to ask right now.

So I really wanna dive into this audience segmentation thing.So is it that you have like set options that you've already decided or is it [00:05:00] like a open question survey? Like how do,how do you actually. Go about doing audience segmentation. Good question.

Brennan: So there's,there's a lot of technical ways of doing it, but let me start with kind of the,what it actually is.

So what I'm doing is I have a set list of, choose one of manyoptions that primarily center around two different things I care about. One ofthem is why are you here? So, you know, what, what's your current focus at theminute? Um, what are you working on? You know, something like that. Like, whatdo, what do they need my help with more immediately?

Why are they joining my email list? Like, what are they hopingI send them? And then I also wanna find out, uh, identity questions. Like, whatemail platform do you use? How experienced are you with it? What, what industryare you in? What, how big is your company? You know, things like that. That'llhelp me deliver better case studies, deliver better examples, and.

All that kind of stuff, right? So I am, um, I'm a big fan ofone of many options. So choose [00:06:00] oneof many because the problem with many of, many, or raw, so like a big textarea, is you can't personalize with that. Um, you can't, if somebody tell typesinto a big text field, you know, I want help with X, Y, and Z, you can'tactually.

Do anything with that programmatically. I mean, sure, you couldmaybe pipe it up to chat G B T, who would then say, oh, put 'em in this group,or something like that. But for the most part, to do personalization, you needto be able to say, you know, given somebody's favorite color, if it's red, showthe red picture.

If it's green, show the green picture. If it's blue, show thegroup blue picture. And that's effectively what I'm doing. Through automatedemail campaigns where I'm saying, if you're here for X reason, then I'm gonnagive you X example, and I'm gonna say X thing to you just to make it so itlooks a little more specific to, to what you're here for.

Akta: And you've alsotalked about personalizing your message. So is that purely just through theautomated emails, or is it also like the weekly email that you write? Like,how's, how does it work? How does it

Brennan: work? So, okay.Okay, so I'm gonna, I'm [00:07:00] gonna giveyou the, uh, the, the machine, the overview of the machine.

Okay. So what I have in place is I have a, I have two primarythings. That are done over email. So the first is the indoctrination, which isthe welcome sequence, and that is actually a multi-month series of emails.Starts out more frequent, and then it gets into things that ask people thatregular touchpoints about What would you like me to write about next?

What do you think so far, now that you've been on my list for amonth, I'd love to hear your kind of raw feedback about what, what you'relooking for. And I use these as opportunities to kind of use the data that theygive me. So they said, I'm here 'cause I want help with audience growth. When Icheck in a month after they join, I say, when you joined, you told me you werehere 'cause you wanted help with audience growth.

For the last four weeks I've been sending you email, afteremail, after email about how to build an audience with or how to, how to babasically build a better email list. Am I doing that for you? Like here's justa check-in type thing. So I'm using it for that, for that welcome sequence andthen. [00:08:00] After or while that's goingon, I put people in into an automated newsletter where I have three tracks.

And these three tracks mirror the three reasons why peoplejoin. So when somebody joins, let's say they join on a Friday, they're gonnastart getting my welcome emails that are all dialed into what they told me thatthey need help with. And then every Tuesday like clockwork for the next fewmonths, they're gonna get an email about, say, audience growth or an emailabout turning subscribers into customers or whatever else, depending on whatthey've shared with me.

So I'm using. The segmentation data to drive specific messagesto people, namely different emails to people. Um, and, and my, the way I dothat is I just, I look through everything I've ever written and I grouped itinto one of these three buckets. And then I said, great. Well, if somebodyjoins and they need help with audience growth, what are the best things I'veever written about audience growth?

And I'm just gonna send them week, by week by week that ratherthan just it being a live feed of whatever I happen to be writing about thatweek. I also have that live feed of whatever I happen to be [00:09:00] writing about that week that goes out onThursday. So what that means is that somebody on my email list gets two emailsfrom me a week.

One of them is automated that is specific to what they've sharedwith me. The other is my normal weekly newsletter. Um, and added or andcontained in all of that is a recommendation engine that I built that allows meto have targeted and personalized calls to action that get people in front ofproducts of mine.

Based on their segmentation data. So I'm, I'm, I do a lot ofupfront work. A lot of what I just said, it's probably seeming like unusuallycomplex, but the good thing is it's done. It's one and done. And now all I dois I write my weekly newsletter. I send it out to my list, but the calls toaction that, the things I want people to do.

When they're reading my newsletter, all of that's dynamic. Soyou might get an email from me that is pitching you on a certain product, mine,and it's describing that product in a different way. Whereas somebody else getsthat same exact email, that same exact email newsletter, and they're seeing atotally different ad, or they're seeing the [00:10:00]same product being promoted, but it's described differently.

Um, so if you, if you. What a lot of people frankly do is theyjoin my list a few times. Maybe this is why my list has grew quite a bit. Theyjoin it a few times with different inputs, different, uh, they, they answerquestions differently and they just kind of reverse engineer what I'm doingthat way, which I guess I'm okay with, but yeah.


Akta: Wow. That'ssuch a system. I've never heard of someone with so many different parts of asingle newsletter. A lot of the creators I speak to kind of have that oneweekly newsletter that they write every single week. What advice would you givethem, do you think? Personalized messaging. Is something that most creatorsshould consider.

Brennan: I thinkwhere it matters really is with the initial experience somebody has with yourlist. So I think, I think it, it, it, I think it makes sense generally speakingfor everyone to find out a bit more than just their email address and theirfirst name when you get a subscriber to your list. 'cause most of us, The onlysegmentation data we have is we know they're, it's not even segmentation data,but [00:11:00] we, we have their first name, wehave their email address and maybe we tag them at their customer or somethinglike that, but we don't really go beyond anything like that.

So what I would recommend would be to do something where you'reproactively telling people, I wanna make sure I create the right content,create the right products, give you a better experience, reduce the amount ofnoise I send you. And the best way for me to do that would be for you to sharewith me.

What are you looking, what's your biggest challenge at theminute? A bit about like you and your needs and that kind of thing. Uh, becausethat'll give you, even if you don't do anything personalization wise with that data,it just gives you a nice top-down view of like the composition of your audienceand who are they, like actually who are they?

Um, what percentage of people fit this profile versus thatprofile. And I think a lot of us know at a gut level who our audience is. Weknow, oh, we have designers on it, we have developers, we have marketers. But Ican actually tell you that, you know, 72% of my audience is this, and 24 isthat, which I think is a really [00:12:00] nicesuperpower to have, um, because it, it helps you figure out what to do.

But then over time you can start to say, well, if half of mylist is just starting out, and the other half is people who are a bit moreexperienced or looking to scale, well those who are just starting out, ifthey're seeing only. Welcome emails for me that are all about like, Hey, I'mgonna help you scale your business.

And here's a example of somebody like Nathan Berry or somethingor, or whatever, and somebody who's truly a beginner is gonna look at that andthink they're in the at the wrong place. Whereas somebody who's established, ifthey're seeing the opposite, which is all beginner stories or something,they're also gonna think they're at the wrong place.

So my thinking is assuming you can equally serve both, Make itclear when somebody joins that you are listening that to what they shared withyou and that you have a plan for them to help them with whatever challengethey're facing, given their unique situation, given where they are, and kind ofthe journey, I [00:13:00] guess is a greater orwhatever else.

Um, so that's, that's what I've been doing. And it, it worksreally nicely because in terms of like every metric, 'cause I do a lot of ABtesting with this too. Every metric shows that more specific language always beatsgeneric language. 'cause if somebody is seeing, you know, common denominatorlanguage that needs to appeal to a wide variety of people, I.

They might not see themselves reflected in what you're sayingor you need to say if you're this, if you're that, if you're that, if you'rethat, if you're that, I can help. But then it's just a lot of noise. Whereasif, if you're on a super niche list and it's like, Hey, for people who lovedogs and live in Lestershire, like here's boom.

Like people who love dogs and wants to share are gonna thinkthat they're right at home when they see that. And that's basically what we'retrying to emulate just in a more. Automated way, instead of going super niche,being able to stage kind of wide, but giving the experiences for eachindividual subscriber, making sure that they have a [00:14:00]kind of a more unique experience.

And when

Akta: you go aboutdesigning that sequence, like for example, let's take the welcome sequence, howdo you kind of decide what's the most important to them and how many emailsneed to go out to them and you know, what that sequence is gonna look like?Like?

Brennan: So I have.And this is actually covered in my book, but I have, um, I recommend fouremails typically for a, a welcome sequence, which is four day at a time.

Emails. The first one is more of just a. I've, I've heard whatyou have to say. And here's my overall plan, given what you've shared with me.So, you know, welcome to Create and Sell. You've shared with me X, Y, and Z.Here's what I hope to do, and, and, and here's how I can help you. Here's kindof, I. My why, why I'm, uh, qualified, and so on and so forth.

Right. Um, so the first is just to kind of make it clear thatthey're at the right place and show them you are listening. You do have a planfor them. The second email that I sent is kind of the [00:15:00]transformation email, where the idea there is to say, if you know you, your,your struggle now is you sell digital courses and coaching and you are juststarting out and you need to help building a list.

If you can achieve that, here's what this might look like foryou. So you know, maybe you're doing this as a side hustle. Imagine being ableto go full-time on this. Imagine what it would be able to do. Just kind of apaint a picture for what tomorrow might look like for them. The 30 mill thenwould be going even further and saying, here's a specific person that I'vehelped who fits the profile.

Of somebody like you, here's their story. So again, what you'retrying to do is just kind of really make it clear you've done this before, youhave a plan for them, and you're pointing them toward kind of what could happenas a result of them saving on your, on your list for a while, and ultimatelybecoming a customer, and so on and so forth.

And that the fourth email, the final email. Would be kind ofsetting the right expectations about [00:16:00]what's to come. So, you know, every Tuesday and Thursday you're gonna get anemail from me. Um, I'm gonna be checking in periodically. Here's like myYouTube channel. Here's maybe a podcast that I, that I host or something justto kind of get them maybe outta the inbox and following you on social media,subscribing your YouTube or, or whatever else.

Um, and just to kind of really set the stage of what to expect.'cause I think a lot of people, they get like lead magnet. They get P D F andthen. Randomly, they start getting newsletters or something, but there's noclear kind of bridge between the two. So that's my recommendation at a minimumfor welcome sequence.

That's personally what I use. But then I also, like I said, dothings where I kind of check in every few weeks, every few months, just to see,you know, it starts out more of like, how can I help you? Like go to this forumand let me know if I could dedicate next week's newsletter to you. Will youtell me what that newsletter should be about?

And that gives me. It kind of automates the collection ofthings to write about, which I think is all of us as creators [00:17:00] struggle with sometimes. So it kind oflets my audience, lets me kind of have inbound market research for what Ishould be doing. Yeah. In an automated way. And then, then I use that sameextended sequence to also, like I've mentioned, check-in.

Say, say you shared X with me. That's why you're here. Am Idelivering on that? And if not, what I need to do differently? And if so, whathave you liked so far? And it's just a really good way to kind of collecttestimonials effectively on autopilot, uh, that way too. Yeah. So I'm very bigon having these nice systems that are lifecycle based, that are based on how.

Who somebody is and how they are kind of in the overall journeyof their relationship with you and just having these nice check-ins and stuff.So how

Akta: many audiencesegments do you actually have in your list?

Brennan: Well, I justcalculated this yesterday for right message, so I'm gonna tell you on the rightmessages end, uh, a right message.

We have a total of, so I, I calculated [00:18:00]how many variations of our email course do we do? We do. And the maths aroundthat is you basically take, uh, What, what I call a segment group, which islike a category, so like industry job role. And then each of these has segmentsunder it. Um, so we have 135,000 variations of our email course, um, that we'redelivering.

Which sounds crazy. Yeah. But it doesn't mean we have 135,000separate sequences or hundred 35,000 emails. What we're doing is we're, we haveconditional content in our emails that say, if you've told me that your emailplatform is ConvertKit, instead of us saying, so, you know, to think aboutsegmentation with your email marketing platform.

Instead we say to think about segmentation with your ConvertKitaccount. Okay. Um, and we just kinda stack all that. So if they say they are asoftware company, um, they use HubSpot. They have a lot of experience withpersonalization on the website, but they don't have much with [00:19:00] email. We're using all that to changesentences and even replacing paragraphs and stuff, which again, it, it, itseems crazy to the number of permutations that, that we're, we have available,but what we're delivering is something that didn't take a ton of time to set upabout 10% of the time.

The authoring time of the email course was spent coming upwith, okay, well, you know, make it say, convert kit here, make it say activecampaign here, make it say HubSpot here, or whatever else. Um, that's the easybit, to be honest. It, it was tedious, but it was the easier bit. Mm-hmm. Um,but what it's done is it's made it so when somebody joins, if they say they're,uh, e-commerce company who uses Klaviyo versus somebody else who says they're asoftware company who uses HubSpot, they're gonna get most of the same content,most of the same educational material in that email course.

But there's gonna be little refinements made that make themfeel a lot more at home. And that's kind of what, what we're, um, trying to do.So I haven't calculated with Create and Sell, I haven't multiplied all thenumbers yet. Um, [00:20:00] but with rightmessages it's a hundred, 135,900 something. I've got the exact amount.

And what

Akta: if you are notin such a clear cut niche? So you're not really sure maybe what segments toinclude or what categories within each. Segment to include. How do you go aboutfinding out enough about your audience that you are setting up audiencesegmentation in a way that actually works?

Brennan: Yeah, sothis is something I've actually helped quite a number of people with, um, wheremy recommendation is usually if you have an audience already, so you have anemail list, but you have no idea who they are and you don't really, you can'tguess.

What groups to set up or what segments to set up. An easy emailto send is, Hey, I'm looking to, I wanna make sure that over the next fewmonths I create the right content for you. Would you mind replying to thisemail and sharing in a sentence or two why you're on my list? So why are youspecifically here?

Like what are you hoping to learn from me? And in a few words,a bit about who you are. So obviously that'll depend on. What kind of audienceyou have. But like, [00:21:00] let's say you'rein the health and fitness space, it would be like, what is your current fitnessgoal? And um, I'd love to know like, are you, are you married single?

Do you have kids? Um, you know, are you looking to buildmuscle, lose, lose weight, you know, why are you here? And then let peoplereply to that and you're gonna get a lot of raw feedback. But you can start tokind of go through that and you'll start to identify kind of common trends,right? I, I tend to. Uh, open up a blank spreadsheet and I'll, I'll go throughthese responses and then I'll say, every time there's kind of a unique newthing, like something that, you know, somebody hasn't said before, I'll add itas a new column and I'll paste in the response into that.

So, over time, you start to have, you know, you're gonna have ahandful of columns with raw, in their own word, voice of customer. Language foreach. So you'll see like weight loss and then somebody is like, oh, I reallywanna shed the pounds or something. And then another person will say, oh, I [00:22:00] want to look at naked or something.

Right. And, and you'll have different ways kind of describingthe same thing, but you'll have weight loss as a category or as a segment. Allthat raw data is gonna be great in the future. 'cause then when you're comingup with like, say, personalized campaigns, you can say, well, if somebody saysweight loss, I'm gonna talk about the look of Naked and the Shed, the poundsand all the raw language that actual people shared would be, whereas somebodywho's looking to, you know, get really muscular, they're not gonna, thosearen't the words they're gonna want to read.

And, and that's not what they're gonna wanna see.

Akta: Okay. And whatabout, um, double opt-in or single opt-in, because that's something that I seeon email platforms all the time. Like is there a significance to what youchoose and how does it

Brennan: work? Imean, I tend to prefer single, and I'll tell you why. Um, okay.

My, my issue with double is most email pla I haven't seen anyemail platform that I think does this right. And, and what I mean by that isthat like, let's say with ConvertKit, which is the platform I use, if you dodouble opt-in, [00:23:00] They send out oneemail that says, click here to confirm. But if that, if that's never clicked,that's, you can't email them and ConvertKit's never gonna nudge them in any anyway.

So what I prefer doing instead would be a single opt-inapproach where you basically put them in a quarantine for maybe a month or afew weeks or whatever time period you want. Where you're basically tracking,you're sending multiple touchpoint, so obviously the same first email of like,Hey, to confirm, click here.

But instead of it being a built-in incentive email, likeConvertKit calls, it's just an email sequence you set up. You can then send afew emails and say, if after following up with them for a few weeks, they stillhaven't clicked the stupid link, then we automate and unsubscribe, then weautomatically unsubscribe them.

So the benefit there is, 'cause a lot of people, myselfincluded, I'll be on say Twitter, like in bed or something, and I see somethingcool and I opt into it, but that I don't go into my inbox because it's [00:24:00] means like, you know, going into my inbox,which maybe I don't wanna do. Then by the time I do check my email the nextday, it's way down low and I forget about it and I never see it.

And now there's no recourse for that creator to talk to meagain. Mm-hmm. So I prefer single opt-in, but with the same end effect asdouble opt-in, which is making sure that somebody truly does what it be on youremail list.

Akta: And how do youmake sure that you are encouraging engagement amongst your audience with yournewsletter.

Like, is that something you

Brennan: consider alot? Yeah, I mean I tend to really like replies 'cause it's one of these thingswhere I really get encouraged when people reply to my emails saying how muchthey liked my emails. Yeah. Um, so I think asking for those replies is alwaysgood at asking. Um, it could be a straightforward as just say you write about acertain topic, asking somebody to reply and tell you what they plan on doingnext.

As a result of what, what you shared with them. Ask for eventhings like I've done where if you completely disagree with what I just said inthis [00:25:00] email, I'd love to know why.Like reply, you know, we, we could, we'll still be friends. Um, and I, I reallylike having these kind of scalable ways to create, I.

Individual conversations over email, especially when you'rejust starting out. I think that's really important. Maybe when you're on likeJames clear level and you have 2 million people on your list, you don't wannaget potentially 2 million replies. Um, but I think when you're especiallystarting out, it's a good idea.

And the other thing about that is, um, it does help withdeliverability. So when right, email servers like Gmail, see that a replyhappens to an email. Whether it's automated or real, that is a signal that thisis a, a real, you know, real email that 'cause who we don't reply to likeAmazon order notifications.

Right? Um, or at least I don't, but if, if, if you send me, ifI'm on your list, you send me an email, I'm more liable to reply to that.Especially if you want me to, if you ask me to, if you gimme a reason [00:26:00] to. Um, and that just helps with overalldeliverability. So it's kind of, you get a. You get the, the raw data back andthe ability, especially if you're selling coaching or something, you couldthen, somebody could reply and say, Hey, this is great.

I've really struggled with this. And then you could follow upand, and say, oh, well tell me more. And then eventually that leads to a paidcoaching gig or something. Right. So I, I'm really big into letting mybroadcast emails turn into kind of sales discussions and, and stuff.

Akta: Yeah. And I'mreally interested how you integrate.

Products into your newsletter? So for example, coaching, doyou, do you have like an email that is just, that's just for coaching with acall to action? Or do you kind of integrate it into, you know, what you'regenerally writing? Like how do you do it in a way that works well?

Brennan: Yeah, so Ihave my, I, I really have, with Creighton Salt, I have one main product andthat is mastering ConvertKit.

So it's course and ConvertKit. And then I have, I guess [00:27:00] the book, which is, Weird because it's notsold by me. So I don't actually know if you're a customer, 'cause you buy it onAmazon and you know, who knows if you're a customer. Um, so I don't really havegreat data about that, but I do segment people when they obviously buy mycourse.

So one thing that I do, and I, I meant, I kind of brieflytouched on this earlier, is if you use ConvertKit, Then you're gonna be pitchedon mastering ConvertKit by me. If you use active campaign, you're not, becausewhy would an active campaign user get pitched on a ConvertKit course? But ifyou do use ConvertKit, then I'm gonna be promoting that to you.

And there are kind of two media, two methods that I use to dothat. Really. Three actually. So the first is more, the more kind ofintentional. So you're on my list. You shared with me that you use ConvertKit.You will get a dedicated promotional series of emails about ConvertKit at somepoint. On top of that, in my, in my normal newsletters, I have, I mentioned thecall to action that I include in that recommendation engine that I built.

Well, if you use ConvertKit in that recommendation engine [00:28:00] will be promotions for masteringConvertKit. You don't use ConvertKit, it won't be, you'll be getting promotedto write message in other products of mine. Um, so that's kind of, that's theone I I really like most because I'm able to just write my usual newsletter.

And I know that the promotional stuff I. Is really dialed inand targeted to the reader. Um, and I don't need to think about it. I justknow, cool, sending out to 10,000 people something, we're gonna get promoted.That something we can get promoted. This, it automatically figures out ifyou've already bought Master ConvertKit, you're not gonna get an ad for MasterConvert kit, because that'd be silly.

So it's, it's, it's smart in that sense. Um, and I really, thatthat's what drives, frankly, most of my sales is just, I just need to do the,the creating of content and. It's kind of dynamically placing differentpromotions depending on who somebody is.

Akta: Yeah, and youalready mentioned that with your welcome email sequence, you unsubscribe peoplewho haven't.

Or you know, [00:29:00]anything like that. But do you ever go through your email list and cleanse itof cold subscribers like every so often? Or is that something that creatorsshould think about doing just to drive up that

Brennan: engagement?Okay, so I'm gonna be controversial for a second. Okay. So when I said I dothe, when I do the scrubbing, I only do that for one type of, Subscriber, andthat is the ones I paid for.

Because the way Spark Loop works is if they stay subscribedafter 14 days of being my list, I pay for them and I'm paying $3 as asubscriber for referrals, right? Mm-hmm. Which adds up. Yeah. So what I do isif somebody does not engage at all, and they came via a paid channel, so SparkLoop, then I force them off within 14 days.

If they're not engaged for everyone else, if you come directlyto create and sell an opt-in, I actually don't do that. And the reason I Idon't do that is because first off, open rates are not accurate at all. When anopen rate is really all, all that that means is that a hidden image is shown [00:30:00] or just loaded, and then that phone's hometo the email platform saying, Hey, this subscriber opened this email.

So that's all an open is. But especially with all the privacythings going on these days, a lot of email clients are either proxying those.Or disabling images from being loaded. So if you're ever in Gmail and it saysimages, were not loaded. That means the person who sent you that email, unlessyou click load images to them, you have not opened that email.

Um, so that's usually the metric that these auto pruning thingsuse is open rates along with click, click rates. So open rates are accurate.So, I've spoken to quite a few people who are really good at deliverability,and the consensus seems to be that until you're sending hundreds of thousandsof emails to hundreds of thousands of different people, that email platformsreally don't care about you.

They're not gonna think of you as a spammer or whatever else.So I actually don't do any [00:31:00] pruning,uh, because the last thing that I want, so I sur charge a thousand dollars formastering ConvertKit. I get a good amount on sales of that. If I auto prune youand you could have paid a thousand dollars to me in a few months, that's areally dumb decision, especially if it has zero impact on actualdeliverability, which generally doesn't until you're in the big leagues ofsending.

So I personally don't do any scrubbing because the only benefitof scrubbing is. Saving a few pence per subscriber, whatever they charge,right? Like, yeah, it, it, it's not that much in the grand scheme of things,the cost savings just isn't much, especially compared to like the potentially Ikicked you off my list and you could have been a customer.

It just doesn't. It doesn't equate to me.

Akta: Wow. I thinkyou're the first person I've come across that has said open rates not reallythat accurate or important. So I'm curious, like what metrics do you look at toanalyze your newsletter growth and how well it's doing if, if any? Like what?What do you

Brennan: look at?

Yeah, I mean, so [00:32:00]click, click rates do better. Open rates don't 'cause clicking is somethingthat despite all the, all the privacy things, the way it works with a clickrate is when you, if you include a link to your website in, in an emailplatform like ConvertKit, what they actually do, and you might see this when,if you click on a link that from, you know, a ConvertKit sent email.

You're gonna, if you look at the U R L bar, it go, it's a, it'sa ConvertKit U R L, that then quickly flips to your site. And what that is, isknown as a proxy, U R L. So what happens is when you click on A U R L from aConvertKit email, even if it's meant to go to your site, it first goes toConvertKit and then they register that as a click, and then they pass it on toyour website.

So there's no way around that. And the only caveat there issometimes some email, especially the enterprise, some email. Platforms andprograms will auto click every link looking for phishing links and will make itbasically register a click even though no one actually opened or clicked youremail. So, but that's rare, especially if you don't email people in big [00:33:00] enterprises.

If you're just setting it to people with like Gmail accounts,you don't really need to worry about that. So I look at clicks, but my biggestthing is really sales. I mean, that's, that's what I'm looking for is what kindof revenue am I getting as a result of clicks from, you know, emails that Isend to sales pages that then turn into, add to carts, then and, and then theyput in their credit card and buy.

That's the thing I care most about because the thing is theopen rates not being accurate. Where they are kind of accurate ish is when itcomes to relative open rates. So if you're consistently getting, say 60% openrates every every week, and then one week you have a really terrible subjectand you get a 40% open rate, even though you probably realistically don't haveanything close to 60, 60% open rates, that is a bit of a, a difference and.

That indicates that something is different about your subjectthat made fewer people willing to open the email. But generally speaking, youcan't look at 60% or [00:34:00] whateverConvertKit dashboard tells you as being anything authoritative. Okay. And

Akta: then in regardsto the links, is there any kind of best practices?

Like should you kind of be aware of how many links you'reincluding? Like does that. Impact things.

Brennan: I mean, itdepends on the kind of thing you're sending. Like if you're sending a, ifyou're trying to sell something, it tends to, it, it's generally a pretty badidea to have like a bunch of calls to action that go to different products.

'cause it just leads to confusion and paralysis and not knowingwhat to do. So generally speaking, most marketers will say, you know, one callto action per email, which I, I agree with. But if you're setting a really indepth kind of research backed newsletter and you want to cite. So you mentionedlike a, I don't know, some sort of data point and you wanna link to the review,or not the review, but the like article that, that initially included that datapoint.

Um, those are really called ACT calls to action. So like when Iread a long form email that's kind of a newsletter, I will link to [00:35:00] Twitter threads or. Blog post or whateverelse. But when it comes to the calls to action to like what I want somebody todo next, do I want 'em to reply to this email? Do I want them to buy somethingor whatever else?

I tend to try to have a single action that somebody should takeas a result of going through that email.

Akta: And is it evera problem to have that same call to action for every email, or is it like, doesthat get too repetitive? Yeah,

Brennan: that's agood question. So I mentioned I have, my main thing is that kind of.

Automated call to action that I put in my newsletters. Yeah, ifyou, let's say you've bought everything of mine except for one thing, thatmeans you're only gonna get promoted, that one thing. But I do have variationsset up, so it will cycle through different ways of describing it. Like, so theright message one has three different variations that are shown.

So there is some randomness there. Every week. It's not gonnabe like the same stock thing. But I, generally speaking, I mean I do that askind of a way of just being able to kind of mix up the message. But [00:36:00] generally speaking, I don't, I, I don'tthink if trying to get sales, like I don't think it's necessarily a bad thingif you're showing kind of the same thing.

'cause it does take frequent exposure and, and maybe like nowthey're finally at the right point to be ready to be receptive to your, youroffer. I'm not too against kind of that kind of repetitive promotional stuff ingeneral.

Akta: Okay. And whatabout, um, let's talk about email platforms because I feel like there's just somany.

You've already mentioned ConvertKit, there's beehive with,yeah, syn in Blue. There's just so many. What should people be thinking aboutwhen they're choosing which platform to use?

Brennan: I think a, abig mistake people make is they go into, they, they tend to, not, not everyone,but some people will go by cost initially, and they'll go for one that is.

More limited in features, but it's cheaper. And then I thinkthe problem always is, is that as a email marketing effort matures and as youstart to add more automations or want to add more automations, migrating isreally, [00:37:00] really hard. I mean, onegood thing about being an email platform is that it's really a pain to move.

Your emails or unless you're just sending broadcast emails,which is kind of easier if you have automations in place and you have a lot offorms and this and that feeding into your email platform, um, and then you havelike stripe hooked up to it and then you have like podia and teachable and allthis stuff, it becomes really difficult to, to change.

So with that said, I think if. If money shouldn't be a factor,I wouldn't really make it a factor. I'd look for the, what are the, there's aquote about like houses, like you should never, you should buy your, your dreamhouse first or something if you can, or whatever. It's kind of that same thing,right? Okay.

I go for something that is feature rich enough that if you planon doing higher touch sales and you need built in C R M, then I would go forthe active campaign or HubSpot account. Day one, I wouldn't try to kind of gooff like something that is a little less powerful and then try to switch later.

Again, it's doable. It's just not, it's not fun. It's never anyfun to migrate. And it can be a bit risky too. [00:38:00]So if possible, I would look for, given the kind of business you run, I'd lookfor, you know, if you're running something on Shopify, then you're probablygonna go to Klaviyo or Drip or something, because that's who they focus on.

You wouldn't go to beehive for that if you're, you know,looking for, C r m stuff. Again, active campaign, HubSpot, or one of thosethings. I would just really try to find the, the brand that has the featuresyou want along with you seeing yourself in the audience. If you're a creator,ConvertKit and beehive, do a good job at like targeting you.

Um, and that's usually where, where I would start.

Akta: Amazing. So I'mgonna end now with a quick fire round. So I'm gonna ask you five questions thatI ask all creators that come on air, starting with what's your favorite thingabout being

Brennan: a creator? Ithink honestly the, um, the eventually being able to solve that, what I callthe, the, the coma problem, which is, you know, I went on holiday last week toAthens, my wife was speaking at a conference, hung out with my two year old thewhole time.

[00:39:00] And emails went out,people were nurtured. People bought stuff. Like I could go into a coma and forthe foreseeable future there'd be zero impact on anything because I haveautomated newsletters, I have automated welcome sequences and stuff like that.So I think that kind of truly separating, you know, getting, being able to getoff that hamster wheel of needing to log into ConvertKit, write somethingoriginal, send it to keep the list warm and all that stuff.

I think ultimately that's my favorite thing is kind of truly.Detaching time for money in that sense.

Akta: Yeah, I thinkthat's actually really, I'm glad that you've said that because I think.Creators who are listening, they might still be on that hamster wheel. Hmm. Itmight highlight the importance of what you've been talking about today, so I'mglad that you've mentioned that.

Yeah. Yeah. Um, what's something that gives you the mostinspiration for what you

Brennan: create? Ithink, honestly, like, and this is something interesting 'cause I mentioned,I've run a software company too, and I was actually describing this to somebodyyesterday where I'm like, with create and Sell, I'm like a guide.

I'm, I'm telling people like what to avoid and what not to door whatever else. Um, how [00:40:00] to best doemail marketing and, and the way that I think it's done best, I. But then I'malso like a tool vendor with Right Message where I'm selling a, a, an app,right? Like a, a software product with right message. I never get feedbacksaying like, 'cause of what you've given me, I've like changed my lifemeaningfully.

Um, whereas with Create and Sell, I do get that feedback wherepeople are like, you've never heard from me. You don't know who I am. You've,we've never talked, but I just wanna let you know I did something a few monthsago based on what you shared with me. And it's like completely changed mybusiness and it's trajectory.

And I think that's, to me, what, 'cause I've, I've been doingweekly email newsletters for 11 years now. Like I, it's not. I've been doingthis a while, and the one thing that never gets old is that, I mean, money hasgotten better as I've been doing this longer. Um, I've made more money doingthis, but that part still is just as exciting as it was the first time I got anemail like that.

So for me, that's the, that's what does it.

Akta: Nice. Andwhat's one tool that helps [00:41:00] you mostas a creator?

Brennan: Hmm. Uh, Imean, for me, The, the thing I, the, the, the heartbeat of it is that my, atthis point convert it because if that went belly up today, that coma proofsystem I mentioned would fail. Um, so I'd have to say that, yeah, I'd have tosay, um, I'm very dependent right now on convert It and it's automations.

Akta: Okay. Um,what's something that helps with your creative work-life balance?

Brennan: Um, Iactually, I, I think like, so. I'm obviously not from here, but I live in theUK and I think moving here from the States has probably been the biggestcontributor to that. 'cause it's really, yeah, I mean people here I think just,uh, are a little better work-life balance than Americans, to be honest.

Oh wow. Um, So I think that has helped. Uh, I mean, my dailyroutine is like walk, walk the baby to nursery, go to the gym for an hour and ahalf, come back, do a few hours of work at the computer, and then [00:42:00] go pick up the baby from nursery, whichI'm doing after this call. Um, and to me that's like all the balance I need.

Like I'm able to get my creative energies out by creatingstuff, but I, uh, yeah, I just get to kinda enjoy Nice, amazing, nice life. Ilove

Akta: that. Andwhat's one piece of advice that you'd give to other creators?

Brennan: I think thebig thing would be truly kind of how we started things, which is do better, dobetter proactively listing.

And I think that what that means is I think we kind of havelike a, um, not, again, not to get too UK ish, but I'm, again, I'm, I'm, I'm,Yeah, if you go to Hyde Park, Hyde Park Corner, right in London and they havethe, uh, what do they call 'em? Like the speaker's Corner thing, right? Yeah.Um, and it's just the people like who rant about stuff and to whoever willlisten.

I think a lot of us, when we're doing our newsletter, we'relooking at it as like a broadcast. I mean, that's technically what, let's sayplatforms like Convert, convert, you call it, when you think of broadcast, you [00:43:00] think of one to many and not a, not adialogue. There's no, there's no back and forth. But I think even as you scale,Even as you add tens of thousands of people to your list, I think if you canfind and build systems that allow you to constantly get feedback, um, that'smore than open rooms, that's more than clicks.

So any of those vanity metrics I talked about, which I don'talways approve of, um, if you can find out specifically why are people joiningin their own words Also, also, what does this mean to them? What would it dofor them to be able to kind of change this or change that? That's going to keepa really nice, tight feedback loop between you and your audience that you canuse as inbound market research you can use to help write sales pages.

'cause the audience is literally telling you their pain pointsthat you can then recycle on sales pages. Um, but most importantly I think itjust allows you to tell people that I am listening. I might be listening inaggregate, but I am listening and I wanna make sure that I'm [00:44:00] always creating the right stuff that youneed from me.

Um, so yeah, I think that's what I'd say.

Akta: Amazing. Thankyou so much. I mean, it's like you've said, you've, you've actually reframedhow I look at newsletters completely. Oh. With this call. Okay, cool. 'cause Idefinitely, I definitely thought of it as like a broadcast. Yeah. And I thinkit's really interesting how you've kind of flipped it around.

Like, and even when I think about email marketing, I've alwaysthought it was a bit too like salesy, but the way that you've made it soundlike. Community building, listening, like getting actual research that you'remaking more valuable content. I think that's just really insightful. So thankyou so much for coming on air.

Of course. It's been a great conversation. Yeah,thanks Akta. If sponsorships are part of your newsletter strategy, then checkout Passionfroot. We help you to streamline your entire sponsorship workflow.I'll see you in the