Joe Casabona: Is your newsletter the product or is it the way to promote your product? Some creators treat their newsletter like a magazine, but others treat it like their sales team. This is something that I have really struggled with. I want it to be both, but I've treated it more like a product, which means I haven't sold to my list as often as I probably should. When. Which means that when I do try to sell something, no one buys because they're not warmed up to the idea of buying from my emails. So I brought in my friend Dylan Bridger to help me sort all of this out. Dylan helps course creators and coaches with their welcome sequences and helps them make more money with their newsletter. He also became a dad this year and so we talk about how that has affected his workflows.
Plus, we get into a short lived side project that taught him a ton in the few months that it was live. I really think you're going to enjoy this episode. Dylan is a great guy. He's a wealth of information and he helps me personally clear up a lot of issues I've been having with my newsletter. So definitely check it out. Check him out. All the links in the show notes. But for now, let's get into the intro and then the interview.
If you're overwhelmed by a chaotic business that's stealing time from your family, streamline. Solopreneur is for you. Hey everybody. My name's Joe Casabona and I've been there. And on this show I will show you how to turn chaos into clarity. So you can stop checking your email at the playground.
All right. I'm here with Dylan Bridger. Dylan helps course creators with their email marketing. Dylan, how are you today?
Dylan Bridger: I'm doing great. Joe, how are you? Excited to be here?
Joe Casabona: Likewise. I am fantastic. So let's dive right into it. You're still helping people with their email sequences. How exactly do you do that?
Dylan Bridger: Yeah, so I'm still doing it. It's been, been in business now for about four and a half years or so. And the way I do it is really just to, to go super deep on research. So figuring out what makes, you know, you, Joe, and your product unique and just really trying to tease out those little morsels that are fascinating and then crafting emails around those in a way where it's ideally constantly enhancing the relationship and not just, you know, shoving products down people's face. So kind of creating that narrative and trying to make that, make that make sense.
Joe Casabona: Do you think people, like, skimp on the research phase in their own work?
Dylan Bridger: Definitely. I Think it's the biggest, it's the biggest difference maker. Like in my, even from my own experience, like there have been times over my career where I, where I haven't done as much research and inevitably those campaigns do not do as well, where the ones where I go really in depth perform and like it's really excruciatingly draining and boring work but it really makes all the difference. And especially today with like everybody AI tools, you know, you can sort of get some ideas started, but I still think there's a massive place for that human synthesis of the information.
Joe Casabona: You preempted my question. So anybody who's playing the 2025 AI drinking game, take a drink because it's been mentioned how, how are you using it?
Dylan Bridger: Yeah, so honestly I use it, I use it more so internally for my own writing my emails than I do on client facing stuff. And it's partially because I've done some tests on side projects where I've run human generated copy against AI generated copy. And it's not a massive sample of data. Like I've probably only spent like 3 to 5k or so in total kind of, you know, tinkering with this. But it seems like when the human generated copy, as of right now, you know, 2025, it's, it's been pulling better for me and my tests so I just want to look out for what's best for clients. So I kind of over index on the human side there. A really good use case for it however, in both client and internal is just you get the rough ideas down and then you edit your draft. But then those tiny details to add some of the nuances of the author's voice.
It can be really helpful for that. Just sprinkling in layers of their voice. That's one good thing. Another thing is like coming up with ideas you might not have otherwise thought of. So I'll sit down, I'll come up with maybe 20 ideas and then, you know, I might even feed the AI with that and be like, what am I missing? What are some more ideas that would resonate with this audience? And a lot of times it's generic, but sometimes Even if it's one in 10, it'll be something I had I would have never thought of. And that alone makes it worth it, kind of as like a gut check, if that makes sense.
Joe Casabona: Yeah, absolutely. And, and so the timing for this is perfect, right? Because I am working on a sales email that I don't know if I've. This is like another thing that you probably get asked about, but like, when's the perfect time to send an email? We're recording this at 2pm Eastern on Tuesday. I was hoping to send this email out earlier, but I haven't yet. But something I did to help me with this is I have a new product. I've done three calls for it already. I gave Google Gemini, which is the flavor of the week for me, the transcripts. I said, what's the language they use? What are commonalities? Can you write a draft email? And I think like, what you said is right.
Joe Casabona: Like it gave me some good stuff, but it didn't give me, for example, a direct quote from a client during one of those calls. It didn't leave a spot for a testimonial. Not that it would have known I got one, but spot for a testimonial. And then there's also like a scarcity factor, right, where I'm. I'm only doing this 10 times, right? And so like only 10 people will be able to buy this thing. And again, like it didn't know that, but that's for, for me to fill in. So I think this is really, really interesting approach, right? It gave me kind of the rough sketch for what my email should be, but I just like haven't filled it out enough to feel comfortable hitting send on it, I think.
Dylan Bridger: Yeah, for sure. It's like when it, when, when these tools were first coming out. And like, Claude is definitely the one I would turn to for anything writing adjacent, more than probably any of them else at this moment in time anyway. But at first I was excited about it from the idea of like a content generation perspective. But as time goes on and on, I find myself kind of inching back towards doing most of the generation by hand and then using it as either like an ideation or like that final polish. Because admittedly, especially if you're on a tight timeline, like when you draft something, you usually want to have Ideally at least 24 hours to like sleep on it, come back and read what you actually wrote and not what you kind of thought you wrote. Right. So I find AI is good for that.
If you're in a pinch and you need to kind of run it through a bit of a polish, what AI does in that final polish is usually good enough. And I just instruct it to basically only deviate when it's absolutely necessary and leave it as close to the essence of the original as possible. And that works pretty well for me. And I do that with a lot of my own emails and a Lot of my own social content. Not so much social, but emails and it's been much faster.
Joe Casabona: Nice. Yeah, I think for me, I always tell it, don't edit the original work, just tell me the edits to make and then I can. I kind of. Because I. My prompt is like, I'm a better writer than you, so don't even try. Just tell me if it makes sense. So I like that. Now, last question here, right.
I kind of prompted you in the beginning before we hit record. I don't want this to be a personal Joe coaching call, but how does one get over the fear of hitting send? Right? Because, like, what I've got here is got a subject line. I don't know if it's good. I've got the content. I don't know if it's good. I've run. I've run like a beta of this type of coaching call. And I, the people who had it loved it.
And I am actually, I'm doing more than I've ever done to launch a product which is actually like, use language from people who have tried the product. And I'm still just like, what if it fails? Like, what happens if no one buys it or no one wants it?
Dylan Bridger: Yeah, well, email in particular, there's a number of ways I can answer your question, but to that last point you just made, like, if that fear of what if no one buys it is one of the bigger blockers that's holding you back from pushing send. Like, the truth is, email as a medium is very forgiving for that particular issue because unlike social media, when you make a post and you either have, like, crickets, like 0 replies and whatnot or tons, email is a very private medium. You know, I'm not suggesting to be dishonest, but what I'm saying is that if you send an email and no one buys, candidly, that's really between you and yourself. And while it doesn't feel good, the stakes are more internal than they are publicly external. Right. So that's just something I always like to keep in mind. Your list kind of doesn't know the difference what's going on behind the scenes. And also, you never know.
I try to approach email, and honestly, just business in general, with the pretense that most things will in fact fail. So that is reality. And if you just put that as a constraint and then just essentially go through the motions to unearth those one or two things out of ten that might be successful, it makes it easier on the soul to brace for all.
Joe Casabona: Those failures that's really good. Again, the other drinking game is Joe mentions baseball. And so in baseball, right, an exceptional hitter hits.300, which means they only connect 30% of the time, right? That's considered exceptional. So, yeah, you're right. It's just, I don't. You know what? I don't think I do enough is I don't think I swing enough. Because the other fear is, well, I don't want to annoy my audience by always trying to sell them something. And so, like, you know, I think I had a weird setup.
You helped me with my welcome sequence, and it's great. It's like largely on the. The words have changed, but like, the structure is largely the same. And this new offer will hopefully slot into that last spot. But I'm actually, I'm actually curious about this too. Now. This. Now we are going into Joe's curious about something Joe did, please.
But, I actually changed my welcome sequence to go out once a week. So like on Wednesdays, it's like welcome Wednesdays. And I know I got this idea from, I think Barrett Brooks and I think Nathan Barry also does that. And I'm just curious, like, as the architect of my welcome sequence, what do you think of that approach?
Dylan Bridger: So it sort of depends. I think if your goal is to use your welcome sequence to generate a response, whether that's a lead raising their hand or a sale of a product or whatever it is, if that is your goal, I tend to recommend front loading, you know, kind of more or less being more frequent on the front end of the journey. So like maybe doing it like immediately and the next day and the next day, if not even more aggressive. And the reason for that is because when someone opts into your newsletter at that very moment, they are, they're like telling you through that action that they're interested in what you are about and what your solution is right then and there. However, you can probably empathize with this as, as a, as a consumer on the Internet, I certainly can. Which is fast forward 24 hours, not to mention seven days. You're probably in a completely different headspace. You might have completely forgotten about why you cared about subscribing to Joe's newsletter.
You might be on to the next thing. So if you can keep the momentum going, there's kind, I, I believe there's kind of like a. A decay in interest that naturally occurs the longer someone you know goes through that sequence. And for that reason, if you want to kind of get in front of someone when they're most likely to be receptive to your sales message. I think sooner is better.
Joe Casabona: Interesting. So I think this goes to purpose, right? Cause I think, like, something I have certainly struggled with, right. Is. Is my newsletter the marketing arm or is it the product? Because I love writing. You know, I love writing about automation and mindset. I don't know if your burner email address is still on that list or if you even see, like, the emails I send, but, like, every Friday, I. That's not a test. I know.
No pressure, but I see some of them anyway. Every Friday, you know, it's Automation Friday, and it's like, very educational. Right. And Mondays, I don't officially call it Mindset Mondays because everybody calls it that, but, like, it's like a. More of a mindset piece. It's like what I'm thinking about in the moment to yesterday I wrote about, like, a headshots because I went on viral. I went viral on LinkedIn for the first time ever. I saw that and then.
Right. So I was shocked. I didn't think that would go viral. But, like, you know, it's whatever. The thing you. The thing you don't expect to go viral is the thing that will go viral always. And then. And then I call Wednesdays welcome Wednesdays, and it's like, here's to.
Here's how you get to know a little bit about me. And so, like, can you speak to that a little bit? Like, how do you know if your newsletter is the product or is just like your. Your marketing tool?
Dylan Bridger: It's interesting you say that right now, because to tell you the truth, I was out on a walk yesterday and I had this kind of. I was just reflecting a little bit on my business, on my offering, who I help and stuff like that, and I realized that this might actually be kind of a fundamental, maybe a disconnect in the way I've have been presenting my solution to the. To. To the market that I serve. And it's exactly what you just said. I mean, for. For some camps of, like, solopreneurs, course creators, whatever you might. Coaches, whatever you might want to call them, the newsletter, like you said, is.
Is more so just like a value. I think it's. Josh Spector refers to it sometimes as a value delivery mechanism. So, you know, it's like just delivering value, not necessarily, you know, hoping for or even expecting a sale of any kind. And that's completely valid. But there's another sort of camp of creators where they're kind of doing. Delivering value and also making the sale kind of at the same time, which is maybe a little bit more kind of like old school Internet marketer E. You know, in that, in that, you know, telling stories than asking for a sale, sharing a tip than asking for a sale.
If I'm being really honest with myself, my, my sweet spot and what I tend to do best of is that that ladder camp of, you know, kind of offer a bit of value, but ultimately viewing it as a marketing and as a sales tool for, for better or worse. So I think I just say that to answer your question, that they, they are, they are different, different things. It's not to say that they can't coexist. You know, I do believe that you can have, you can still deliver a ton of value in an issue while teeing that up to a sale, whether it's a super soft sell at the end or even just having the, the piece of education being a demonstration of your expertise to tee up doing more. But honestly, I don't know if I have an answer to how you sort of define what its role is in your business. And I guess if it is more of a value tool, I think it's important to eventually ask yourself, you know, what is my sales process? What is my sales mechanism? You know, because ultimately you need to generate sales for it to be a sustainable business long term.
Joe Casabona: Yeah, I mean that's a really good, I think a really nuanced answer. Right? Because like what you just said, like tell the story, ask for the sale. That's like kind of my move, right? Like, I mean, and I have been looking through like Caitlin Burgoyne's emails because I know like when she sends her more value based emails, there's one template and when she's asking for the sales, it's a different template. And you know, I'm in Chanel Basilio's community where for most of those folks like the newsletter is the product. And you know, so I've been like, I think I've been really struggling with that. Right. Because I don't, I don't really participate on social media aside from LinkedIn and I don't really know how to sell on LinkedIn. And so the, the, my biggest acquisition channel honestly has been Google, which is kind of crazy.
Dylan Bridger: Oh wow.
Joe Casabona: Like SEO, like I'm record, we're recording this. Yeah. In the year 2025. But I, I want my newsletter to be more of that. And so I think like I, I really have to have a, a hard think about the positioning of that and I think I know the value I offer and it's just like, how do I want to invite people into this? And maybe, you know, I've engineered this in a pretty smart way where I have a sequence called short welcome where it's just like one email after the confirmation. I do like a double opt in, but they still get a confirmation email because they got a free thing where it's like, here's how it works. And so I do have the flexibility to add to that and then still have like the welcome Wednesday, like emails after that. So I think it's like something to think about. And it's probably, as you probably know, always an experiment.
Dylan Bridger: Yeah. And like, to be clear, there's nothing, I don't think there's anything wrong with your idea of having those like, longer tail drips of like once every week for however many Wednesdays or however you have that configured. Because if nothing else, that's good. You're just, you definitely know that you at least have, you know, one email going out every week for an extended period of time, which is good in case you ever, like miss a week or, you know, you're behind on your content calendar. But yeah, it's, it's an interesting, it's an interesting question.
Joe Casabona: And I mean, yeah, right to your point, right. When someone walks into a car dealership, they want a car, right? No one just, I mean, maybe some people walk in just to look, but as far as the car dealer is concerned, they're probably a very warm lead and they know that if they leave, they might go to a different car dealership or they might decide, oh, well, we, we can, we can stand for one car for a little longer or whatever that is.
Dylan Bridger: Yeah. And like, one thing you might like, you probably have this already configured already. But just a really quick point to your last point is like, if you're not sure if you want to like, go too hard on like the promotionalness, because the newsletter is, is perhaps the product itself, one way you could do it too is like have like link triggers. So if someone clicks a certain link, like maybe you have like somewhere dispersed in your ecosystem, you have links to your products and your offers. If someone clicks that, then and only then you can have an automation that follows up with them a little bit more in a bit more of a direct sales manner. Because those folks, if they made it onto your list and if they clicked a link to go check out your product page, those folks probably want to be sold to more than you realize.
Joe Casabona: Right? Yeah, that's a good point. I did do that for a while. Right. I did like the classic click on this product and then if they didn't buy, hey, why didn't you buy? Right, like that sort of thing.
Dylan Bridger: Yeah.
Joe Casabona: Cool. All right, I want to switch gears a little bit. You recently became a dad. Recent is a relative term, but I want to know what's the biggest way your work has changed since becoming a dad?
Dylan Bridger: Yeah, for sure. So I've been a dad now for eight, eight months as of a few days ago. And the, the biggest difference, I think, like I should preface this by saying I'm very fortunate that my, my wife is, is currently on maternity leave. And so during the days, that's a huge relief. She's, she's able to do a lot of the heavy lifting during the, during the kind of traditional work day and we have grandparents who can help as well, so we're well supported. But I think it's caused me to, to, to kind of focus on fewer, more stable, kind of higher paying clients and really shift gears from an, a new customer acquisition lens to a retention, retention customer satisfaction lens because it's so much easier to keep and continue delighting an existing client and keep getting paid from them than it is to find a new one. So that's been one, um, major way my work has changed. Um, but I'd be lying honestly if I said that I haven't been a little bit less motivated and inspired by work than before I had my daughter.
Um, so that's been, that's been kind of a negative thing that has, that has definitely been noticeable for me. Um, and yeah, so those are kind of a couple things. I can unpack more details there.
Joe Casabona: Yeah, I mean, I think that's like super. So I mean, my first question, right, as someone who's based in the United States, you are based in Canada. Have you thought about, is it like, do they, do you get a year maternity or is it like.
Dylan Bridger: Yeah, I think she has a, I think she has a year if I'm not mistaken. Yeah, roughly that.
Joe Casabona: I mean like it's, it's like the Wild west in the United States. You get like, depends on the place. And then with fmla, you get, you get, you get your job guaranteed. Like you can be gone for six months and like not lose your job, but like paycheck is not so like, it's very. That's not politics, friends. That's just a fact. That's just a straight fact. So have you thought about, have you thought about yet what it's going to look like when your wife does go back to work or if she's going to go bad. That's, like, a really personal question. So answer that however you feel comfortable.
Dylan Bridger: No, for sure. Yeah. She plans on going back to work in a few months, and she's already kind of slowly started that process. She's just doing some work kind of from home here. We've thought about it. The details are not fully firmed up, but the beauty is, since a lot of the work I do is asynchronous in nature, and I've, like, designed it to very much be that way and set very clear expectations with any of my clients, it allows me the nimbleness to kind of work in a day when I. When I need to. I mean, it all depends on, like, energy levels and stuff like that.
But so we have some support through our. Our grandparents, the. My parents. Her parents. Yeah, that's going to be a big assist. There's probably going to be. It's probably going to be. Look like some of those days of the week, I'm going to be doing it, and then other days she's going to. But the sort of more honest answer is we're in the process of still figuring that out a little bit. But that's kind of.
Joe Casabona: Yeah.
Dylan Bridger: Yeah.
Joe Casabona: I think, like, that's the most honest answer. Right. Because I think, like, I mean, I went into it. Oh. Oh, yeah. I'll just work on the baby naps, and I work from home, and Aaron's a nurse. Anyways, it doesn't matter. And it changed, like, having a.
Here's a fun fact about babies. They don't nap when you need to work. Right? Like, yeah, they don't. They might not nap one day. Right. And they. Well now, so be flexible. Give yourself lead time, I think is probably the best. Like, if you need to do something in two days, give yourself four days to do it. Right. Because who knows when you're gonna find those two days. So, yeah, I think that's a really healthy and probably the most correct approach is like, we're gonna figure it out as we need to.
Dylan Bridger: Well, that's good hearing that from you because you're. You're a few steps ahead of me on the. On the parenting front. So.
Joe Casabona: Yeah, my youngest is gonna be four at the end of the year, which is wild.
Dylan Bridger: That is nice.
Joe Casabona: Yeah. Awesome. So. So that. That's really. That makes a lot of sense there. Now, something else that you did actually. No, hold on.
Let's go back. Joel, you can edit that part out. Okay. So you mentioned that you want to keep Your you're trying to keep retainer clients, right? It's easier to continue to delight current clients instead of always trying to find new customers. I feel like this is a lesson that everyone hears, but it never sticks. And I think like mo, like a lot of parents who are also business owners, it took having a kid to make a lesson like that stick. So I'd love you, I'd love for you to speak more to that in whatever way that you feel it will be the most impactful. Right? Like maybe like what, what were you doing to get new customers versus how have you reallocated that time to your current customers?
Dylan Bridger: Yeah, for sure. So just to add a bit more of a dimension to it, I'm always on the lookout and open minded if customers are wanting to reach out and do business. Because the truth is things change and that makes sense no matter how much you try. Customers will churn for various reasons. So I think it's one thing you definitely don't want to do is get caught where something changes in a client's business and all of a sudden you're three to six months behind trying to, I should add, I sell B2B services. This is different depending on what you sell. But you know, if you're a solopreneur selling Some sort of B2B service, this is particularly relevant to you. You don't want to get caught where like something changes and then you're three to six months behind what you need to do to get your next client, whatever that might look like.
For context, most of my clients come from word of mouth. Some come from my, my own email list. I have a, a small but pretty engaged email audience myself that I, that I mail and promote my services to. And I was once upon a time it was more so cold outreach in terms of like that kind of thing. So. But the thing is, is like once upon a time, my. When I was a little bit more naive in business, my, my mindset was get customer, like that is the goal and like, you know, do what you said you would. But if maybe it didn't work out as well as they would, like, you know, that's life and you move on.
That was like my, my. I'm ashamed to confess it, but that's how I once kind of thought about things. Whereas today my new perspective is, you know, get like, get the customer and realize that that's like the starting point, not the end point. So that's the starting point where like it's all about keeping them happy in every which way. So there's the actual, you know, the work product and the results from the work, whatever that might be for you. But what I've learned is that equally as importantly is, you know, like, communication going above and beyond and the little details that they're not expecting stuff like that. So. Or like if things don't go as, as you had hoped for any reason, making it right is another big thing.
Like still to this day, some campaigns don't work as well as I hope, despite my best efforts. And you know, I try to think like, how can I make this right instead of just moving on to the next thing? So it should be common sense and it should just be like basic integrity. But I think when you're, when you're just gunning to grow your business, it can be really easy to overlook that kind of thing. And I just think if you're really genuinely operating from a frame of taking care of your clients really, really well, you can kind of get a lot of other things wrong and things will tend to sort of balance out, I've found.
Joe Casabona: Yeah, I love that. I am so former guest on the show Summer Os. Do you know Summer?
Dylan Bridger: I don't actually know.
Joe Casabona: She has a newsletter called Emails Done Right. It's kind of like how to make money with your email list as well.
Dylan Bridger: Oh, cool.
Joe Casabona: But she, she posted on LinkedIn recently about kind of the importance of nurturing the relationship with current customers. And I said going for the sale of like getting a new customer and then forgetting about them is kind of like the one night stand of business.
Dylan Bridger: Yep.
Joe Casabona: It's like, all right, well I've got your money. So now I'm going to leave through the window and try to find the next, you know, sucker. So I really resonate with what, what you've said here. I think that's really important.
Dylan Bridger: It is, yeah. And it's like, it's so, it's so easy to overlook because, you know, a lot of the excitement I think is like we, we glorify like this. Getting the sale, getting the clients, growing the business. But it's, it's just, yeah, it's, it's an important piece of the puzzle.
Joe Casabona: It's like what the business bros say, right? Bigger, more hustle, more clients get close, more deals. Right. When it's like, you know, I think just as a society, it's always more and more and more, but like, be happy and cherish what you have. I know that's like a really deep for a business relationship, but it's, it's really important. I think in all aspects of life, it is.
Dylan Bridger: And like, ironically, like, when you do that, other, other things to your selfish benefit will tend to materialize. Like, recently, I had a customer who once had a. An engagement with. Hadn't worked with him in. In a couple years, reached out to him and just kind of made like a remark about, you know, like a positive remark about something he was doing that I could see from being on his list. And next thing you know, he said, like, I want to re engage you. And today we're working together again. So even on the selfish front, it's just good business to be doing this as well.
Joe Casabona: Yeah, absolutely. Now, the last thing I want to key in on here is you said that you're B2B for the long time. As a matter of fact, up until a couple of minutes ago when you said it in my head, B2B has always meant like Fortune 500 to Fortune 500 companies. Right. Like big business to big business. But I assume that that's not actually the case for you, right? You're a small business owner and you work with other small business owners, right?
Dylan Bridger: Yep. For the most part, some of them are doing like nine figures, but nonetheless, they're all kind of in the scrappy startup mindset, and some are generating more than others.
Joe Casabona: Yeah, yeah. So I think I just wanted to point this out. Like, B2B is not a size thing. Right. It's that the value you most deliver is to another business. And I think, like, considering how you deliver that value, like, I'm B2B. Right. I help other solopreneurs and small business owners. I'm not selling, like a consumer product to someone. So I think that's a, again, another just really important thing to think about.
Dylan Bridger: Yeah.
Joe Casabona: I guess it's also worth noting that, like, if I'm. If I want my newsletter to be a product, I should also consider that. Right. I deliver value most to other businesses, not necessarily to consumers. And so that's really. That's really interesting. I feel like my mind has just been blown, like in this moment right here. Always good on.
Joe Casabona: On your own podcast.
Dylan Bridger: Nice. Glad to hear it.
Joe Casabona: Yeah. Yeah. So before we get to the side hustle, I checked the schedule. This episode is being released a couple of weeks before Black Friday.
Dylan Bridger: Okay.
Joe Casabona: So I'd be remiss if I didn't ask you to give your top one to three Black Friday tips. Number zero. Could be. If you're just starting to think about Black Friday, it's probably too late. Maybe it's not, though. That's Just what I've heard.
Dylan Bridger: No, absolutely, yeah. It's funny because to be honest, I have, for someone that does email marketing campaigns for a living, I have done fewer Black Friday in particular launches than you might expect. And that's partially because, so sometimes I'll do engagements where I'm, I work on a commission only basis. So I'll generate your emails, we'll deploy them, and I get paid as a result of what I bring in. And Black Friday can be a great time for generating sales, obviously, but it can also be a very competitive time to stand out in the inbox. So ironically, I actually sort of favor sneaking in in times that are kind of random and coming up with funny reasons why we're doing a promotion than I do always following the pack in terms of Black Friday. With that being said, I think a lot of what I do kind of on an evergreen basis throughout the year would be just as relevant with Black Friday and well, relevant by necessity. But I think like having short windows of a sale, I think is, is a very powerful thing.
So instead of like, you know, five days or something, like going for like a 24 hour, 48 hour max kind of a window can be very powerful. And over that amount of time, I really think it's like as many emails as you can stomach sending and still go to bed at night and, you know, not hate yourself. I think that's probably a good goal because most of the businesses I work with, their problem is never sending too many emails, it's always sending too few. So I would think basically the maximum you think is reasonable, aim for that and then pick, you know, your favorite five or six or seven emails from that pack and go and go from there. I'm trying to think things, Black Friday in particular that are relevant.
Joe Casabona: Well, so let me actually follow up on that, please. Should you send more than one email in a day?
Dylan Bridger: Yes, definitely. During, definitely during a launch or a special promotion. And especially at a time like Black Friday when everyone else is sending probably more than one email a day and everyone else is doing it at the same time because you know, someone opens their inbox, they see yours, two minutes later, it's going to be absolutely just stampeded with other inboxes. So they could have been a perfect candidate, they could have bought that, but they just didn't open, didn't click. So you need to pop up to the top of their, top of their inbox. You know, this assumes you have decent like, deliverability, health on some of the, the technical side of things, which I'm admittedly not an expert on, but you know, if your average open rate is like below 10% then you're going to want to be very cautious doing anything like that because chances are there's technical problems that you don't want to aggravate by doing that.
Joe Casabona: Right.
Dylan Bridger: But like if you're sending one email a week all the time or one, two, three emails a week, you absolutely should send more than one email, especially on the deadline day of your promotion.
Joe Casabona: Ooh, that's good. That's really good. Because I know like, you know, I've heard again, Nathan Barry say this again. Nathan Barry, coming from the world of your newsletter is the product, right? More or less, yeah. Never send more than one email in a day. Now this was general advice for why you should have automations and why you should have different lists and stuff like that. Maybe it's never send more than one value based email in a day. But I just, you know, I want to make that distinction because I think people internal, I've certainly internalized it. That's why I know I can only send sales emails on Tuesday, Thursday, Saturday and Sunday because I already have emails on Monday, Wednesday, Friday. So I think that's a very important distinction to make.
Dylan Bridger: Yeah, it's and I know it's, it's like one of the class, especially in the email marketing community that like I'm in. It's, you know, it's a, it's a debate, right? You know, like people, businesses never want to send more in and like I get it but like I just encourage you to try to think about it from your consumer's perspective when you open your email inbox, like you know how, you probably know how crowded that space is and like sure no one likes to receive tons of emails within minutes of each other, you know, you know, have a little bit of taste with it, but certainly towards a deadline, like assuming it's a really good offer, that's the key thing, right? You're like, I'm assuming here that you have a really good product that's going to help someone. I think there's no reason why you shouldn't make a splash in the few moments where in the grand scheme where you are actually promoting something that's legitimately special.
Joe Casabona: Yeah, I like that. I'll also just say here like I bought something from NFL.com a week ago, two weeks ago, something like that. I've gotten multiple emails from them a day to the point where like I kind of like unsubscribed a bunch of times and marked it as spam. But when I need my next Giants thing, I'll be going back to NFL.com.
Dylan Bridger: Right.
Joe Casabona: Like, you know, if, if, if you're selling something that people want, then you should be or that will help people. Like you said, they should know about it. And the only way to know for them to know about it most of the time is for you to send them an email or a text maybe. How do you feel about tax campaigns?
Dylan Bridger: I haven't done a whole lot of work with them. In fact, I've done 00 work with them. So I can't really comment with any authority. But I think yeah, if you have the SMS list, it's an asset I would use for that though. My, my uneducated opinion is to probably veer on the side of less is more. Just because it's a little bit more, it's less crowded again than an email inbox. Right. So there's less actual need to follow up as much, I think.
Joe Casabona: Yeah. And it's, it's a lot more personal. Right. Like I don't have email notifications on it on any of my devices actually.
Dylan Bridger: Yeah, likewise.
Joe Casabona: But like text notifications. Sure, of course, yeah. Awesome. All right, so I want to wrap up here with you. Shortly after you became a father, decided to launch a side project which I'm not going to judge because shortly after I became a father I left my full time job and started my own business. So, you know, fatherhood makes you do crazy things. Maybe it was about table tennis. Tell me a little bit about table tennis. What drew you to this?
Dylan Bridger: Yeah, so like for context, I have been playing table tennis or ping pong just like with friends, totally recreationally for, I don't know, the past few years. Like on the weekend we, there's a bar where I used to live and we'd go and like, you know, just play there in the middle and have some fun. Um, it was just purely like, you know, play. And so I got inspired. I follow this. There's this very interesting person named Ken McCarthy and he, he kind of goes way back in the Internet and he has this, this website. What is it called? Oh my God. It's, it's escaping me.
It's about jazz. Jazz on the tube is what it's called. And what it is is basically just like this daily email that goes out and it's just a video to a great jazz live performance every day. And he got a lot of attention from it like back in the day. So I found it kind of amusing. So I Said, what if I take that same concept but do it for table tennis rallies? And that was essentially the idea for this. The project was called Rally Real, where every day I would curate and send like a, a one line email about some crazy table tennis rally I had seen on YouTube. And that was the idea and that's about the extent of where it came from.
And so I said, okay, maybe I'll just like build this in public on Twitter and LinkedIn and just have some fun with it. And I think if I think about the motivation, I think it was because right after I, you know, I think I, when I became a dad, I was lost a little bit of inspiration from my main line of work, a little bit. But I, I didn't want to just blow it up, like blow up the business and do some other idea. So I said maybe if I just like allow my, give myself permission to do this side project and not have it be too much of a distraction, that will scratch the itch. And. And so it did. So I, you know, I gave myself a constraint to only grow it through paid ads. So I had meta ads running and I grew the list.
I, I mean I, I think I only put a few hundred bucks in it, but I, I grew the list to like 150 or so people and had had some people replying with interest and stuff and some people from my main business poured it over. But to tell you the truth, when I was like a few weeks into this project, I immediately lost, lost all momentum and interest in it. And it's, it's, it's now a failure. Not a failure, but it's, I'm no longer working on it. I still have my beehive account sitting there. I'm still paying for it, but I'm just delaying the inevitable to, you know, just shut it down and. Yeah, and I think there's a number of reasons why that's the case, but, and I haven't really announced that publicly, but like, yeah, is, I think the, the path to doing it on a long term was a path I, once I got into it, I wasn't sure I was realistically wanted to do. And there was some signals from the market as I was doing it.
Like it started admittedly just as like a fun little project for me and maybe I should have just kept going with that frame. But when I got a lot of feedback from people that were joining the list, I realized these were like really professional. Like not professional but like advanced table tennis players from the states and they were like asking for insights and knowledge that I didn't feel like I was the messenger to bring to them. And I didn't just want to like go to AI and send them slopes.
Joe Casabona: Yeah.
Dylan Bridger: So through a combination of factors, I was just kind of like, is this worth me kind of reshaping and molding into something I'm going to commit to long term or should I take that amount of time and do literally anything else with it? And yeah, I've decided in the latter.
Joe Casabona: Nice. So, I mean, so a couple of things here, right. First of all, did what you learned in your side project, were you able to bring that to your main business?
Dylan Bridger: Yes. A lot of good came out of it. I connected with a few people that like generously reached out and like, it was the thing that interested them to reach out to me. After many times of being in each other's kind of universe, they reached out offering to help. Like, I had this one, this one guy, Tatsuki, he, he's like a meta ads person and he gave me a ton of help with like getting my meta ads dialed in. So I, I kind of like skilled up in, in like advertising, so that was worthwhile. I, I also had the opportunity to test some of this AI copywriting that I spoke to earlier. So I deliberately, with the ads, they were 100% generated with AI and that was intentional.
I wanted to see kind of like, can you even get any traction with AI generated copy? And it did okay. But the ads I wrote by hand outperformed them. And then so that was kind of something. I also connected with another guy, Billy. Billy bro, us. And he was, he gave me some help on, on messaging and stuff like this. So I think from a networking perspective, it was great on that end. Ironically, people also saw me posting about it on LinkedIn and clicked through to my profile and booked a call with me kind of as like Dylan Bridger, the email marketing consultant.
So I got at least one client through it. So there was some cross-pollination there. But more than anything, I think it just kind of allowed me to sort of flush that, that yearning out so that I could refocus on, on the business or at least give myself permission to explore more projects like that if they come in the future. Yeah. So I think it was, it was worthwhile, and I'm really happy I did it.
Joe Casabona: Really appreciate you coming on and talking to us today. And if people want to learn more about you, where can they find you?
Dylan Bridger: Yeah, thanks so much for having me on, Joe. It was a blast to catch back up. You can find me on LinkedIn @DylanBridger, Twitter or X. Dylan, I think it's Dylan underscore Bridger. Or you can go to dylanbridger.com I need to update my website. So, depending when this gets released, that may or may not happen. But in any case, if you, if you google me, dylanbridger.com, you'll find a little bit more about what I do. And yeah, feel free to reach out to me.
Joe Casabona: Yeah, awesome. I will link to all of that and a lot of stuff, stuff that we talked about in the show notes over at streamlined.fm. But Dylan, thanks again so much for joining us. I really appreciate it.
Dylan Bridger: Thanks, Joe. Thanks, everyone, for listening.
Joe Casabona: And yeah, thanks everyone for listening. Until next time. I hope you find some space in your week.