Ditching Hourly

Jason Resnick - Masterclass In Pragmatic Email Automation

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[00:00] Introduction and Workshop Announcement
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JONATHAN STARK:
Hey, Jonathan here. Before we get to the episode, I've got a quick heads up for you. On Tuesday, September 8th, 2026 at noon eastern time, I'm running a live workshop called Positioning for Soloists who are having a hard time niching down. If you know you need to niche down but you've been hesitating because you're afraid of picking the wrong one, cutting off good opportunities, or boxing yourself in, this is the workshop for you. You don't need more convincing that vague positioning is a problem. You need a way to make positioning feel less risky so you can finally choose a direction, test it in the market, and adjust without blowing up your business. That's what we'll do in this workshop. It's the second session of my Fall 2026 Soloist Growth Workshop Series for expertise-based business owners just like you. Live attendance is limited to 20, so don't wait. Details are at jonathanstark.com/sgs, or just click on the link in the show notes. That URL again is jonathanstark.com/sgs. Hope to see you live in Zoom on Tuesday, September 8th. Now, on to the show. Hello and welcome to Ditching Hourly. I'm Jonathan Stark. Today, I am joined by guest Jason Resnick. Jason, welcome to the show. Thanks for

[01:13] Guest Introduction: Jason Resnick
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JASON RESNICK:
Thanks for having me, Jonathan. Excited to be here and geek out about email.

JONATHAN STARK:
Yes, we're going to go deep geek

JONATHAN STARK:
on email automation, so that you are forewarned, dear listener. You might recognize Jason's name from being on Business of Authority. I also actually recently interviewed him for a new podcast called Doing Daily, which is the kind of the genesis of this conversation where it was sort of meant to be a high-level conversation. We completely went off book and got into some fun stuff, and then after the show had probably another 45-minute conversation about really nerdy email automation stuff. So, I was like, oh man, we should just, you know, you were like, it's too bad we didn't record that. So, let's set up another call. So, here we are. Absolutely. All right. So, for folks who maybe didn't hear any of those other episodes, could you just give a brief who you are and what you do to set the context?

JASON RESNICK:
Sure. So, my name is Jason Resnick. I'm

JASON RESNICK:
the founder of NurtureKit, NurtureKit.co, and I am, in your words, which I use lovingly throughout all of my intros, is a recovering web developer turned email marketing and automation expert.

JONATHAN STARK:
Cool. Maybe start with what has been your emailing journey to date? You know, what do you use? How often do you send it? What do you send it about? Who's the target market? That's sort of just high-level stuff, and then we can get into like how you've evolved over time into the setup that you're moving toward.

JASON RESNICK:
Yeah. One of the things that I've, and I don't regret much,

JASON RESNICK:
if anything, but one of the things that I do regret in business is not starting email sooner. And when I did dive into it, it was mainly out of seeing how clients use it. As I said, I was a web developer and I mostly worked with e-commerce sites, not necessarily DTC stuff, but people that were taking transactions online, whether it was a membership site, whether it was digital product, whether it was a physical product. And I saw how email impacted their bottom line. And so I was like, okay, I see something here and I got to get into this. And so what I wound up doing was I started my own personal brand, helping other freelancers really just try to figure out how to build predictable income. And that was out of the genesis of too many people asking me the same questions over and over again. So I was like, all right, I'm going to create this personal brand around this. And so I just started emailing pretty irregularly. And then I kind of ramped it up to once a week. And then I just started mixing in certain things like just testing things. I mean, I'm a developer and so I was just trying to see what works, what doesn't work. How do I get a click? How do I get an open? How do I make sales? And as a, just me personally, I'm always been fascinated by human behavior. And I minored in psychology in college. And it led me down the rabbit hole of which I am today.

And a lot of what I do is based on human behavior. It's email that is smart. We're not using email as a blunt tool to kind of bludgeon people into buying things or unsubscribe. People get value while being on the list. And they themselves signal through clicks, through other things, but through clicks mainly that they are ready to buy something. And then they get pulled into various different automations to help them to that buying decision. And now to this day, currently I send emails daily, six times a week really, to two separate individual lists, one to course creators and marketers and the others is to that freelancer list.

[03:41] Email Marketing Journey
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[05:15] Segmentation and Automation Challenges
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JONATHAN STARK:
Cool. Okay. So it's always been my experience that people can go really nuts with, you know, I'm mostly familiar with Drip, but I understand that this is possible in ConvertKit as well and others where you can go nuts with segmentation and different campaigns and logic, branching logic. And when I first started with it, I also being a recovering web developer went way overboard with that stuff because it's kind of easy to set up, but then it got, it was very unruly and it was hard to tell what kind of experience any given individual was having. Like, did they, are they on like, are they getting a daily email and like three and they're on three like side things? And then I was like, okay, so now if somebody signs up for this, I need to unsubscribe from this and then resubscribe them, but only resubscribe them if they were subscribed before. And it was like, oh man. So, and whenever I've, you know, I read your, your daily list and it's always strikes me that you like to keep things, you like to automate things, but also keep them simple. Is that? Absolutely. Yeah. So talk about that. Like how did you, what was the, what was the, what was an early win for you in terms of like a simple automation that produced some results? Landing page abandonments. Just having somebody

JASON RESNICK:
click a sales page, not convert, not buy. And then follow up. Like most people experience this with cart abandonments, but in the space that I'm in with digital products or memberships, there's no cart per se, right? There's just this intent. Hey, there was this interest in the email that got somebody to click over into the sales page, but they didn't buy. Right. And that was like my first, like, oh, okay. That's pretty simple. And much like cart abandonment, the landing page abandonment, the, the psychology of it is the same from both the business side of things, but also the, the subscriber side of things and got similar results. Right. So anywhere between 20 and 30% people converted off of those. So for me, it was like, okay, this is, this is interesting. And much like you, I was, I was tracking everything, right? Like it's, it's funny because I run into people either track nothing, whether they track everything. It's like very few in the middle ground and then you don't get your answers you want if you're at those two ends of the spectrum. And so I did something very similar. I use Drip for a long time.

I use ConvertKit now, but same applies in infusion soft and all of these other active campaign and all these other ESPs, but just being able to understand who the subscriber is and put them in like a central backbone, whether that is a daily or weekly newsletter or something like that. And then allowing the intent of that subscriber to kind of pull them into other things and then loop them back in, right? So just really on, I can't emphasize it enough and I was having, I was actually talking with Jane Portman and she, she had me on her podcast and we were talking about segmentation and that kind of thing. And we went down a rabbit hole and much like what I've discovered and probably similar to you, Jane was like, look, segmentation makes everything else easier. And it's, I found the same way, right? Once I understood who the subscriber is, defining those automations and the paths at which somebody travels down becomes so much clearer, right? And you don't have 87 different automations running, wondering if somebody's getting seven emails on any given day, right? Because it's just like, okay, you know, that was me. Yeah. And, and it was me as well. But once I sat down and thought about the subscriber themselves, where they are, who they are, what's their motivation, those, what their needs are.

Once I understood that, then it was like, oh, I could write emails about this that lead directly to this product. Right. And it makes the path super clear. And it makes everything that much simpler too, because then you don't have to think about all these random pathways and how to get people

JASON RESNICK:
back onto the main road and all that kind of stuff.

JONATHAN STARK:
Okay. So I, I did, it's, I feel seen. I did exactly. I went from like over architecting it to throwing up my hands and tracking nothing. I do no segmentation, nothing. I know very little. I mean, anecdotally, I know who's on my list, but I don't have like a, I can't look and say like, okay, get me all the web developers on the list and I'm going to send them a special email. I don't use any liquid tags whatsoever. Um, yeah. So it's like, to me, it's just, it's the blunt instrument. They're either on the list or they're not on the list. And, uh, you know, so there's probably tons of room for optimization. I am gun shy about going about getting back to that. Like, wait, I don't even know how this Rube Goldberg machine works. Is it even working? You know, uh, I've never been a big fan. Well, we don't need to go down there. I've never, I've tracked stuff and then never looked at it. So I'm like, why am I tracking this? Right. You know, if I'm not going to use it, I'm going to stop tracking it. So, um, that's kind of where my, I kind of swung the pendulum, swung all the way to the other end. Uh, but I, I take your point where, where you can, you can help the, you know, the automation or the personalization and it not just like high first name, but like real personalization can help the reader.

And as long as it doesn't, you know, my, my, the tough bar to clear for me is like, it can't, I want it to be set it and forget it. Right. So like it needs to be simple because otherwise it's going to break, right. Or there's going to be some edge case or something weird. So let's, let's go back into that, that first big win and get really technical about it. Landing page abandonment. So you send an email, it's got a link in it. Are you tracking the click on the link or are you tracking on your website? Like, like who, like, how do you even know that somebody was on the landing page and then didn't buy? What are the moving parts there that, that don't require you to like pour over a spreadsheet? Right. So I was, when I first

[09:58] Simplifying Email Automation
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JASON RESNICK:
set it up, I was tracking both the click in the email as well as using JavaScript to actually on the page to send that back into Drip. Then in Drip monitor, because I already had the automation connected with the shopping cart, I knew if somebody made a purchase. So really it was just, Hey, if these two things match the JavaScript API callback, as well as that click, and they spend a certain amount of time on the page, but don't buy within a certain period of time, send the email, which was over-engineered. Like there's no reason for the JavaScript API callback. And, you know, and I took away some of the criteria. Like, I think I was like, if somebody's on the page for a minute, like 90 seconds or something, like I, you know, I was, I'm a developer, so I over-engineer everything. Right. And so I was like, that's unimportant. Right. If they clicked enough from the email, because that's really all email is designed to do. I can't take a credit card through email. So I have to email is designed to get the click over. So if the click happened, that was enough of an intent on my end. And now I don't even use landing page abandonment anymore. It's kind of matured a little bit more where I'm still tracking clicks over to sales pages, but I'm tracking the number of clicks over a certain given a time, right?

Because sometimes if somebody just comes onto the list, they see the link they're interested enough to click, but they're not ready to buy. Yeah. They're just kind of like, yeah, let me see. Looking at it. Right. But if they click on a second time in a short period of time, let's say a couple of days, if you're doing daily, then there's the intent. They know what they're going over to. Right. And they're going to, maybe I need to read this a little bit more. Maybe I didn't have time on the first time. And now at least know what the price is, whatever the case may be. Then if they click on a third time, you know, the intent is there. Your sales page is not doing its job in converting that person, but tracking that, that is something that I feel you can use Jonathan, because you don't need to know anything about the subscriber for that. I mean, it helps like on my list, I know what somebody calls themselves and who their customers are. Like if they're a course creator, they use customers. If they're a freelancer, they use, you know, they have clients. And so I do the hyper-personalization side of things, but you don't need to do that. Right. And this is something that's simple enough that you could kind of set it and forget it. Like you, you set it up once. All right. Now I just use this trigger link. I just, okay.

If this button or this link or whatever clicks over to the sales page, it just, let me apply this tag or change the custom field or whatever the platform calls for and do it that way. And it is a simple set it and forget it kind of thing. Um, you know, I've, I've have a client that has, you know, he's got a massive, massive list. Um, and he has been using this kind of campaign for quite some time and he's made over half a million dollars in two years, just from that list. And he's now not doing any sort of launches. He's just like, okay, that's good. Like I don't need to stress myself out over those quarterly, quarterly launches anymore to bring people in. It's just on evergreen.

[14:58] Salesperson Campaign Strategy
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JONATHAN STARK:
So you just said the magic words for me, cause I can't stand doing launches. Yeah, me neither. So, okay. So now you really just, you really just flipped a bit in my brain. So, uh, so let's, let's get, we're going to go deep. I told, I told you to your listeners and get deep deep. So I know, you know, Drip and ConvertKit inside out. I only know Drip. So if we could talk about it in Drip terms, that'd be cool. But you know, the principle applies. They both, both platforms are roughly comparable. So you, you said three clicks in a, on a particular link in a certain amount of time. I didn't even know you could do that in Drip. Like it's not with tags. It must be. Well, you'd have to, you have to create a, uh, in Drip, it's a workflow. Um, so you have to create a workflow that tracks that click. So basically it's applying the tag that triggers the workflow

JASON RESNICK:
that then updates a custom field for a counter and then remove the, remove the tag and be on their way. Right? So now every time they get that tag, every time they click that link, it counts them. Now, you know, I've Found with some audiences, like you might want to throttle that count a little bit. Like some people like click the link a few times, you know, or they click on it in their phone and then within five minutes they go to their desktop to click the link. And so there's that level. Like you have to kind of pay attention when you set it up just to understand what your audience's behavior is. But in the basic sense, it's just a simple workflow that, that when a tag is applied to then count a custom field and then remove the tag so that the tag can be reapplied later.

JONATHAN STARK:
Okay. And then, and presumably in there, there's an if custom field is greater than three or just became three, then move them off the main list and put them on a side list that's, that it's like, you know, we can talk about what the side list is in a second, but is that, do you have an if in there?

JASON RESNICK:
Exactly right. So once that count, once the count at the bottom, if they reach three and pass them off into the sequence or another automation or whatever you want to do, if not, just let them be on their way. There's another automation that kind of sits in the side that once that custom field gets updated, you start a timer. So, so that timer is there to kind of say like you and I, we write dailies. I have mine set to 14 days. Um, cause sometimes I do get people binging and like they'll save up my emails at the end of the week and then just binge. And, um, so what I do is I, I, for 14 days, as soon as that custom field gets updated to one that triggers off that other workflow and puts them in for 14 days, just puts them in a little delay for 14 days. That's it.

JONATHAN STARK:
It's just like wait 14 days and then do something. Yeah. And it's basically the trick, the goals of that workflow are the purchase or if the time expires and they haven't purchased, then we reset that custom field to zero and exit out. And you, and that happens on, okay, that was confusing. So I, like, I understand, like I, I get this, the timer side workflow, if they, if your e-commerce platform tags them as they bought this thing that the sales page is for, they've reached the goal and it yanks them out of the pause. Right. But when do you set, do you move them over there when it flips over to one? So, right. The trigger is based on one, right?

JASON RESNICK:
Because we have the one workflow that is triggered off of the, the link trigger, right? So that updates the custom field to one, which then triggers off the second automation, which is just a timer that then drops them into a 14 day delay. If that happens, if they don't buy, what happens at the end of the 14 day delay?

JONATHAN STARK:
You reset the custom field back to zero. Got it. Okay. So that, so it's like, oh, they went for two, they, they clicked, they weren't really that interested. They didn't click again. Right. So you just, it's just a way to reset it to zero if they don't buy. Exactly. Right. Cool. That's so smart. Okay. And it's actually easier than it sounded. That's a really, really short workflow. Yeah. And you know, like, and you can complicate it as much as you want. If you have multiple, multiple products and things of that nature, you know, like if you have a membership product versus a $9 thing, maybe you don't want the $9 thing going out when the membership, you know, so you can blow it up as much as you want, but that's the basic foundation of it. Okay. And so, okay. So then how does the, so if in the 14 days they click two more times, then they are going to, no, they click two more times, but they didn't, they still haven't bought. So there must be a, there must be a, what do you do when someone does buy in that, that counter workflow? If somebody buys, what do you do? In the counter? If somebody buys, that's a goal. So pull them out. Okay. But do you reset to zero? Do you like make sure they never go into this workflow again?

[20:02] Naming Conventions for Workflows
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JASON RESNICK:
So the way that I set up my email marketing is every workflow is a singular function. So if I'm promoting, let's just say a membership at, when that trigger hits three, the number three, I put them into a salesperson pitch for the membership, which is another workflow at the top of that workflow. I checked to see if they bought, if they're already a part of this, they exit

JONATHAN STARK:
Got it.

JASON RESNICK:
So that this way I don't have any funky logic or things to keep track of in other automations based on a product status.

JONATHAN STARK:
Yeah. It does get confusing though. Doesn't like, do you use some sort of like naming convention for your workflows? Cause like, okay. Cause let's talk about that because I get like from a developer standpoint, it's like do one thing well, so that you minimize everything's like a function. Um, and if they can sort of stand alone, it has always been my, like one of the things about the Drip UI is like, I'll look at a workflow and I'll have no idea if it's active, like it's turned on, but I don't have any idea if anybody's triggered it recently or like, like, is anybody, do I have a page on my site that I don't know about that's pushing people in here? Because you don't know, cause the triggers are set elsewhere. So, you know, like you might have a form where it's like, if somebody submits this, then add them to this workflow. But the workflow doesn't tell you that when someone's been added to it or any idea to know that if it's been used lately, well, it does, they've actually

JASON RESNICK:
improved that, um, where you could kind of go into this analytics screen of a workflow and it'll tell you kind of how many people have received emails. If it's, if there's emails in the workflow, but like what we're talking about with the timer and the counter, you kind of have to dive into the workflow and actually go into like the each node to see if this is actually working because there's no emails. So like that analytics dashboard would be just blank.

JONATHAN STARK:
Oh yeah. So, so, okay. Here's another way to, so this is a real developer-y question. Is, is each of the workflows listening for an event or are they, or, or event or are subscribers being pushed to them? Do you know what I mean? Or they, are they sitting there waiting for people to, to like an event to happen or is it explicitly like send jsmith at, at google.com over there? Yeah.

JASON RESNICK:
So the, basically everything is triggered. It, I shouldn't say triggered. Everything happens off of that tag being applied when they click the link. Okay.

JONATHAN STARK:
Right. So if they click that link, then the, the first workflow that is trapped,

JASON RESNICK:
the counter workflow is actually sitting there with that trigger in mind. When that tag gets applied, let's do everything else. So the timer workflow is kind of waiting for something to happen. Right.

JONATHAN STARK:
Whereas we're actually using the links in the email to push people into that counter workflow.

JASON RESNICK:
Yeah. And that's how all of my workflows currently work. Like you go to the top and like, no, one's been added to it. There's no segment added to it. It's like, if, if tag apply, you know, if this specific tag was applied, then suck this person in, but the, are you listening in the, you probably

JONATHAN STARK:
said this, but I missed it in the timer workflow, are you listening for counters to go to one or do you, is there no way to do that? And you have to like, can you get the top? Can you say that the trigger event or the event is like, if custom field equals one, you can. Yep. Oh, that's great. Yeah. I mean the other way around it, because in ConvertKit, you can't do that. Um, well actually I think they just changed it, but like the other way that I've done it in the past is just in the counter workflow, I just apply a tag that that is list that that triggers off the timer, that's all. Right. Fair enough. But only the first time. Right. Okay. So. Well, the tag itself can't be reapplied. So even if somebody comes in the second time,

[24:00] Handling Multiple Products
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JASON RESNICK:
they're already in the timer workflow. Oh, you don't remove it. I don't remove any tags until they're completely done with everything.

JONATHAN STARK:
Okay. All right. That's, I love that because there's sort of like, when I used to do FileMaker, there was a, there was a real problem when you would write these scripts. They were like macros. There was no way to know what was calling it. Like, so if you, if you couldn't, you could never delete a script because you didn't know what was calling it. And so the parallel here is you can never delete a workflow because you don't, because you don't know what might be calling it. But as long as you know that you only put, you only pull people in based on events, then, well, I suppose you still don't know if you could delete it, but. Or it's all based on naming convention.

JASON RESNICK:
Yeah. Let's talk about that. So, so how do you, like these two in particular, let's talk about

JONATHAN STARK:
those. So, so, so you send out an email, it's got a trigger link in it to a particular sales page or a landing page. They click it and a tag is applied and, and so that they hit that counter workflow. How do you name these to keep them straight? Yeah. So the workflows themselves is I, I name everything very similar. Basically the only thing that's going to change is the product that,

JASON RESNICK:
that it applies to. So I would name it salesperson hyphen counter or hyphen timer or hyphen pitch. Right. So now you've got three workflows that are all contained with that specific automation flow, if you will. Right. So when you, what does salesperson represent?

JONATHAN STARK:
So salesperson, that's what I, the moniker that I gave of this kind of campaign, because it's a

JASON RESNICK:
salesperson campaign for me, it's just like a salesperson. The sequence themselves, the emails is basically that kind of salesperson. That's going to come up to you and want to know what room in the house you're putting this TV in, or, you know, do you have an apartment or a media room? Right. And so it's tailored more towards that and open the line of communications, right? It's not this quintessential FAQ, you know, here, I know you have this pain. Here's the solution. Like, here's what other people say. It's not that quintessential sales, sales sequence. It's what, that's why I call it a salesperson campaign because it acts differently. Right. It's based on the behavior of that individual being and having seen your, your product and your sales page.

JONATHAN STARK:
Okay. Well then the product name must figure into the workflow. Right. So the, the naming convention that I would do would be salesperson, hyphen,

JASON RESNICK:
timer, hyphen membership, or hyphen product A, right? Or product B or whatever the case is. And so now if I know, Hey, product B sucks and I don't need it. And like nobody buys this thing anyway, I could just remove all three of those workflows because they're all related to product B. Got it. And so for each, essentially for each landing page, you've got those three,

JONATHAN STARK:
three workflows. Yes. And this model and one tag really that triggers off all three, right? Because one click the link. Yeah. Right. And so that link would basically that, you know, sales, that tag would also have a naming convention to it, which then is basically

JASON RESNICK:
clicked hyphen sales person, hyphen membership or product or whatever. Okay. So now I've got, you know, I use, I use a naming convention that basically is action, which is always a verb hyphen then context. So that's a noun hyphen meta information.

JONATHAN STARK:
Okay. Got it. All right. So then the, so, okay. So the path is I've gotten to three clicks in the counter workflow within 14 days. And that act, what is the action that sends them to the sequence? That's in the counter. If this, the number reaches three and then you tag them with something that, that sucks them into. Yep. Okay. And removes them from the daily list or no? Yes. Yeah. My daily list is, is usually, or I basically have a segment that excludes people that are being pitched. I see. So you'd say like, if the person is in this or this or this or this, well, don't that always gets messy because you're like, okay, I missed one or something. Right. Yeah. I made a new one and forgot to add it to this place. What I do in the pitch sequences, as well as a welcome sequence too, because that's an important sequence is I have a custom field called being underscore pitch and I set that to true. So anytime I'm pitching somebody,

JASON RESNICK:
that is one of the first fields after the check of whether or not they have the product, I set that custom field to true. And so that this way, my dailies are respecting that custom field. So if, you know, as long as they don't have being pitched equals to true, send them this email, then that covers all basis. If I forget, you know, cause I don't, one of the things that I got stuck on early on was like, just building a recipient list was like a nine minute process.

JONATHAN STARK:
Yeah. Cause I was like, I don't know. All right. Well, yeah, these people shouldn't get this. Maybe they should. And I was like, this is, this is annoying. Right. It's a nightmare. I just want to press send and have it go to the right people. And so that's why I was like, okay, keep it simple. My dailies go to everybody unless they're getting pitched or in the welcome sequence. And so being pitched can become hairy, like, because if I've got multiple products and I forget the product, well, all right, fine. In my workflow automation that handles that because I just set that custom field right away. And do you check for that custom field? Like, I don't know if this would be possible, but if, and this might be what you're saying, but like, if they are, do you also check for being pitched in the other workflows? So like, let's say I clicked two different links, three times each. Correct. Right. So I do in a matter of speaking based on priority. So that kind of gets a little hairy, right? Yeah. Because there are some, you know, with any business, there are products that you want people to buy and there are products that you're trying to get people to buy so that they buy the bigger product. Right. Like a ladder. Right. And so if they happen to trigger the, the flagship product, let's call it, then yeah, I basically ignore all the rest. Okay.

So they're, they're thinking about the big HONA. You're going to make sure that that gets priority. So like, and, and just, so it's obviously the dear listener, the thing we're worried about both of us is you don't want to send them like three emails in one day and selling three different products. Yeah. Yeah. And you're daily. Right. So it's like, it's like unsubscribe. Yes. Yes. It's like two over the top. It's not helpful. Like, like the goal of this is to be helpful. So, all right. All right. So then does anything happen? Oh, so let's talk about the sales. So we can see, you said it's not a generic FAQ type of thing. How long is once they get into the sales sequence, like what is the nature of the emails? How many are they? How frequently do you send them and what happens at the end if they don't buy or even if they do buy? Yeah. It sort of depends for me. It depends on, on the product itself,

[30:00] Optimizing Email Sequences
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JASON RESNICK:
right? If it's a $50 product or a hundred dollar product, I usually just send two or three emails. There's no reason to kind of, you know, beat them over the head. But if it's a membership or something else, then it's six emails over the course of the entire week. And I send, because my list is a custom daily. And even when it's, you know, on a list of a client that sends weekly, uh, it's a daily sequence and it goes over the course of that time. Um, I don't, I've tested this in the past to kind of be like, okay, well I don't, it's a sales sequence, but we don't want it to come off as a sales sequence and that kind of thing. Um, but when you, even on the, if it's a weekly email, when you start to spread that out, it's not as effective. And then people just like, all right, they just keep talking about the same thing and there's no reason. Um, ironically though, what I've found that has worked super well over the past year is in the very first email, calling it out, right? Like saying, Hey, I know that you've checked this out. Uh, my system tells me that you check this out. Uh, I want to help you out. You know, I want to make, you know, make sure that all your questions are answered, right? Really just laying it out on the table so that now it doesn't seem creepy. Right.

Like, um, and I got that idea from ironically, uh, an Amazon Alexa show because my wife and I were talking about salmon or whatever. Um, and then all of a sudden random salmon recipes were appearing on the display. Yeah, sure. They're not listening. I've had the same experience. And so I was like, well, that's creepy, right? Like, all right. You know, and I know that it, it has to listen because it's waiting for that weak word, but I was like, Oh, I wonder if you just do this in email. Like, will that work? Like, I mean, people know that it's automated and people always tell me anyway, that like, I can't do anything genuine. People are like, how'd you automate that? I'm like, no, that was my fingers, you know, doing the thing, right? Like, so everyone thinks it's a robot. I mean, I tell, I make custom personalized videos, calling their name and business and people like, how'd you do that? And I'm like, Oh my gosh, I turned on my camera. Yeah. So that doesn't scale. So I was just, you know, I was like, I'm going to test this for a little while. And it actually converted better. Like it, like that email itself converted more people than not calling it out. So it was kind of like an interesting kind of little test that I ran on my own business.

And then I found the same thing with clients as well, that were willing to kind of like inject a little personality into the emails there. So, um, so that's, that's it really. It's just the sequence itself is, is really meant for helping. Right. And so the first email is kind of setting the tone, kind of just like looking at them to, you know, kind of say like, Hey, this is, I see you, right? Like, and then the next email is going into, you know, if you don't know anything, anything about the individual, but if you do, it becomes even more powerful. If you can hyper, uh, make it hyper specific to who they are and sharing a story of a customer that looks like them. Um, otherwise, you know, you kind of know what the benefits of the product is and share a story in that second email. And then the third email is simple. It's Hey, hit reply. Why, you know, how can I help? Right. I don't want to belabor the point here, but you know, S or get off the pot kind of thing, right? Like you're here, you're, you're not unsubscribed at this point. And I know you've checked this and now we've had six or seven emails talking about this, that you've taken a look at the website as well. So there's 10 touch points. You still haven't bought, let me know what's, what's going on here. Um, and then the final two emails is another story usually.

And then, you know, the, the last email is like, I'm getting off this gravy chain kind of thing. Like it's instead of creating a sense of urgency, like there's an expiry, which you can do. And I've done that with some clients, some clients are like, let's give them a 10% off or something, you know? So you could do that, but I'm more of the mindset of like, I'm not going to belabor this point anymore. Um, I'm here if you want to talk, um, you know, that's it. And here's a little, um, you know, like depending on the product, I will sometimes give like a template or a worksheet or something out of that just to kind of, yeah, something that gives them a taste of what, what's behind the scenes. Um, in other cases like memberships, I've actually given them like a six minute loom video of what it does look like behind the scenes in that last email. Um,

[36:00] Evergreen Content Strategy
---

JONATHAN STARK:
and those have worked pretty well too. So what happens when they, you know, they're in the middle

JASON RESNICK:
of the sales person sequence and they reply and you start a conversation? Yeah. I mean, that's a good question. I, I mean, I don't overcomplicate things. They're going to get the next email, right? Like, um, if I start the conversation with them, um, then, you know, obviously the human factor comes into play and they know that they're talking to me, but they also know, because at the top I told them that they were in a sequence, right? Right. So I don't try to overcomplicate it. Um, the only thing that kind of gets hairy is like, like I have these things built in for my services, right? So that becomes a little bit hairy. I will actually remove people out of that because manually. Yeah. Because as with services and stuff like that, it's a longer sales cycle. It's not just, you know, random Tuesday, you're going to buy. Yeah. Right. Right. Right. They're going to, they're going to click a link and be like,

JONATHAN STARK:
here's 25 grand. Right. So, okay. So super, super interesting. And like, I know dear listener, I know we're getting into like small details, but really this is not that complicated, you know, like coming from someone if, you know, a grain of salt, like I'm a developer too. So, you know, the, the logic of it is not that complex. Like you could draw this on a flow chart on a piece of paper very easily. Absolutely. Yeah. If you think like that. Yeah. I mean,

JASON RESNICK:
I, if you, if you imagine a highway really, right. It's just your highway is your main newsletter, your email, your dailies, whatever the case is. And the off ramps are when somebody actually triggers off that link. And then like here in New York, a lot of places on the East coast, it's like a Cloverleaf all the exits. Right. So you got off the ramp, you went down the side roads a little bit, and then you got right back on. Right. Because you either bought or you didn't buy and you get back onto the same highway again. So it's, it is very simple and it's, it's super effective. It just doesn't like a phrase that I love is one by Leonardo Da Vinci and it's simplicity is the ultimate sophistication. And the thing, the thing that I've found with email marketing that, you know, you and I both ran into as well as, you know, plethora of other people is that you do get into the shiny object. Like, Oh, I could do this. I could do that. I could track this, track that. And it's mostly useless. Like you're not going to go back. You think you're going to go back and look at it, but it's just like, ah, now I'm just confused. And then I'm not going to log into this thing because it's overwhelming. Yeah. And so when you think of it, like, Hey, if I get people on the email list that is really just has these sales person campaigns set up for each of the products that I want to sell.

All I have to

JONATHAN STARK:
concentrate is getting people on the email list. Yeah. You can forget about everything else. Right. And it's like, you've got an automated salesperson for each exactly. Right. With a, like with a, a way to escalate to the manager by just hitting reply on any message. Exactly. How much time do you spend encouraging on the, on the sales sequences? replies or just, okay.

JASON RESNICK:
And there's two emails that specifically do that. The first and the third. Um, but people reply anytime, like, you know, they get, so, I mean, I just want to make sure that they open the line of communication, like they know that that line is open and so, um, because the thing that I'd looked at, like I said, is if you get your third email in that you we've hit you now 10 times. With this offer, like you're familiar with it. Like there's, I can't really say much more, like, unless you give me some specific question or thought or feedback or something like that. Um, and that is super helpful for me because then I can just turn that back around on the sales page.

JONATHAN STARK:
Totally. Right. So, and you do ask, you're like, you know, you get to that off the pot email and it's like, Hey, just, you know, if you hit reply, I'd love to know, uh, what the, what do you have, how do you phrase it? Like what the objection is or what the holdup is or just, I'd just say, you

JASON RESNICK:
know, I know that we haven't convinced you to purchase yet, uh, what's holding you back and it's just, I find that that email, the more human you make it and the shorter it is, the more effective it is because they've already seen a lot of, and I want to say fluff is the wrong, but they've seen a lot of copy already.

JONATHAN STARK:
Yeah. Right.

JASON RESNICK:
And so they've read the FAQ, they've seen the testimonials, they've, you know, that kind of stuff. So there's not much more to be said other than let me help you. Like that's what I'm here for. Like there is something that is triggering you to be here still. And so let me help you. And I'm just trying to reach you to the buying decision, whether it's a no or a yes, that's all.

JONATHAN STARK:
Yeah. Right. Okay. So here's a, there's probably going to be even more of these tactical questions and I'm sure your answer to this is like, there's nothing you can do about it, but maybe there's something I could do about it. So it's not uncommon. It's not super common, but I would say 10% of the time someone will subscribe to my email list with an email that is not the one they will use to purchase. And it might even be more than 10%. So I see a fair number of these, like, you know, mailing list at custom domain.com and then when somebody buys, it's like Jeff at custom domain.com. So they end up, well, I guess they wouldn't know that. No, they won't keep clicking though. Will they? So that they'll, the timer will scrub them out. Yeah. So this is the bane of my existence. But yeah, I mean, they're, they're not going to get pulled out of any sequence. Right. And so that's part of this is like when they make the purchase, we pull them out of being pitched and everything else. Um, but they won't, they'll still get those emails. Well, if they, they probably won't keep clicking the link, like they might never get to three clicks. Is that so? Oh yeah. On the front end side of things, then it depends on how you handle your customers. Right. So like me, I put everybody back on the highway, but I know that what they purchased.

So what I do then is use liquid in my emails to kind of filter that link out instead of saying, Hey, go check this out. I will actually nudge them to use the product instead. Okay. So wait, so when they go back on my dailies, if I know that they bought some digital product, when they get that email that talks about the thing that the call to action is to go by, I will actually use liquid code to check, to see if they purchased, if they did purchase, instead of saying, click here to buy, I will actually, I will click the link. I will give them a link to nudge them, to use the product. That's not penetrating my thick head. So in other words, like if, if let's just say that like one of my digital products is, uh, you know, smarter emails using liquid code, right?

JASON RESNICK:
Yes.

JONATHAN STARK:
Met a little bit meta here, but it's basically a code snippet library, right? Rip and run. You can go ahead and paste it into any email and it'll work.

JASON RESNICK:
Right.

JONATHAN STARK:
As long as your ESP is like Drip, you know, put ConvertKit and so on in the email itself, let's just say the email is all about personalization, right? And it talks to, you know, it talks about a story of how, you know, HubSpot did a study that, you know, personalization is, you know, personalized CTAs are 202% more likely to convert than generic CPA C CTAs. Click here to buy smarter emails using liquid. But if I know that you bought smarting, smarting, smart emails, then I will actually say, go ahead and go look at number two and give them the link to the number two snippet. So it actually prompts them to actually use the product instead of buying the product that they already have.

[45:00] Dealing with Spam and Bots
---

JASON RESNICK:
Okay.

JONATHAN STARK:
So, but maybe a dumb question.

JASON RESNICK:
That's interesting.

JONATHAN STARK:
Now, the reason it didn't make sense to me at first was because my assumption would be that you would, instead of advertising the product they already bought, you'd promote a different one that they haven't bought.

JASON RESNICK:
I could, in some cases I do. A lot of cases I actually, especially for smaller digital products, because people buy these things on impulse. And so a lot of times people don't use it. They forget they have them. Right. And so what that does is, Oh yeah, I forgot I had that. And then they'll go use it and then I'll get an email with a testimonial in it. Right. Right. Yeah.

JONATHAN STARK:
I do these, I, I handled that a little bit differently. I have like followup sequences for people when they bought something. Yeah.

JASON RESNICK:
And I do that too. Okay.

JONATHAN STARK:
And I don't, it's like crazy simple. Like they're going to get two emails from me that day. So like they bought, they buy a thing and they get like 50 emails from like Moonclerk and Stripe and all of it. They get a million emails. And then the next day they, they get a, you know, thanks. Um, if I don't know what, you know, it depends, it depends on the product, what the thing might be, but it's the same sort of thing. It's like, like, uh, for example, hourly billing is nuts is available in every digital format you could think of, including audio. So two, two kinds of audio. And I, I'm just out of curiosity. I'm like, what, you know, how do you usually read your, your eBooks? Is it like, like, how did you read this? Did you, I'm curious, like Android, iOS, Kindle, Audible, you know, like, where did you put it? Uh, and I get tons of replies to that. And then I think there's a couple of more, a couple of more after that, but I don't pull them off of my daily list. They're real, real short, like one, one or two question messages. Um, yeah. So I don't know. So I, so I do that follow-up once they complete the follow-up, then they go back on the daily. Okay. Yeah. I just, I don't, yeah, I don't separate it out. They're real short and they're like, they're like, um, I'm trying to, it's the same point though, I'm trying to activate them.

I'm trying to like, I'm trying to like get them to get the value, get the ROI. It's like, you spent 120 bucks, read the damn thing, watch the videos. Cause I don't want you to be, I don't want that, like, uh, I never got, you know, so yeah, so it's the same kind of thing, but I just, it's maybe mine's, mine's definitely a little bit less sophisticated, it's a blunt instrument. Um, but I've never had any complaints. I don't, again, I don't really look at any of the, usually people don't complain when they get multiple emails about a purchase. I found that, uh, people will complain if they like, and it's kind of funny. They opt in to like three lead magnets. Like I'm getting, you know, they'll say like. Next day, like, I'm getting like, four emails from you, right? I'm just gonna unsubscribe. Like, yeah, because you opted in that many times. I got that enough that I de-emphasized all except for one of my lead magnets, because I knew which one was the best. And, and I was that happened a lot where they would just sign up for things. So of course, you got four emails, right? But they don't, you know, it's like, you know, it's like, they imagine somehow I'm gonna, I mean, I guess it's not a crazy thing to imagine that I could somehow know that I already emailed them in the last 24 hours. Like, that would be a really cool feature in Drippy.

Like, did I email this person in the last 24 hours?

JASON RESNICK:
Yeah, but they're never gonna build that in for you. I mean, what I've done, because it was like, you know, I would say about five years ago, where every lead magnet had like three or four emails off the back of it. Right? Now, I just do one email, deliver the lead magnet, and everybody goes into the same welcome sequence. So when somebody opts in, they're expecting the lead magnet, right? Do I care if you use the lead magnet? Sure. But am I going to nudge you three times over the next three days? I'm not going to do that. I'm going to bring you right into the welcome sequence. Because I know off of the back of the welcome sequence, which is the goal anyway, of that initial sequence is to get you to buy something. So if I can start to craft the proper story arc from the welcome sequence into the sales pitch, then that that's the goal.

JONATHAN STARK:
So yeah, that makes sense. I'm more of a fan of the kind of like email mini course lead magnet than the like, here's your PDF. I've seen a decline in those the performance of those though, which the email series.

JASON RESNICK:
Really? Yeah. How's that? It doesn't make sense, though. I mean, if there if I if my goal is to get them on a daily list, sending them seven emails kind of makes sense. I think because people one people don't want to wait. They want a quick win. And I get and I guess it depends on what that sequence is, right? They don't want to have to wait until Sunday to actually get that win. They want the win now. And so I've just my main lead. My main lead magnet is actually one of those email courses, which I'm now changing to a better lead magnet, which is a PDF download.

JONATHAN STARK:
Interesting. I get this objection a lot from software developers who are like, well, you could have just given me the link. You didn't know my email address. Yes, I get that quite often. There are certain audiences like that. Yes, there are. The other so the other thing is, and I do have I have one very popular lead magnet, my main one six day free course about value pricing by value pricing bootcamp. And I have a PDF download of five page proposal template. Those are the two that I kept. And but I just massively de-emphasized on my website massively de-emphasized the template download. So now I could I won't do it, but it would be smart, but I won't do it is to like go back and actually see on a per capita basis, which one performs better. I don't even know how to do that. Like, like, in other words, say like, OK, because it's de-emphasized, the proposal template gets way less traffic. But let's say per person, you know, my customer lifetime value or like like their time staying subscribed before turning off the list is better for one or the other or the people that unsubscribe right at the, you know, like the welcome email, like, oh, thanks to you here. You can unsubscribe if you want, but you're about to go on my daily list and see what the unsub rate is at that point for the two different lead magnets. That would be probably the place I would look.

JASON RESNICK:
Yeah. I mean, what I try to do is with lead magnets, I do two fields, custom fields. One is what they came on to the list the very first time, what lead magnet that was.

JONATHAN STARK:
How do you do that? Like, how do you check to see if it's populated already? Yeah. So I have a origin campaign, custom field, and every lead magnet that they

JASON RESNICK:
come in triggers off a workflow. If that field is set, don't do anything. If it's not, then put it as that lead magnet. And then I do something similar with a last lead magnet. Most recent. Right. So same process or whatever. But basically between those two, it kind of gives me an idea of like, I look at it from the conversions perspective. So if they buy, what lead magnet did they go to last? Because that to me is an indicator of maybe a need that they have that leads to that product. And the origin, the origin, the very first lead magnet in a lot of those cases don't matter as much. Interesting. It's just the one I heard of. So it's like the one that crossed their

JONATHAN STARK:
radar. It's like their first awareness of your stuff. But I use that. I use that first one, like what you mentioned. I check on

JASON RESNICK:
subscribes to see like, OK, this lead magnet actually leads to a lot of unsubscribes within the first 45 days. I don't care for this one. Right. That makes sense. Right. So this is a super tactical question, but like how

JONATHAN STARK:
do you what's your process for like checking this stuff? Like when do you like are you obsessively checking these things or do you do it like on the first of the month or first business day of the month? Like how do you do you work that into your routine? Yeah, I used to. I mean, like anything, it's like when you set it up, it's like your baby. You're like refreshing the screen, refreshing the

JASON RESNICK:
screen. But I just like I will look at it regularly. I would say probably every three weeks, like by accident. No, intentionally. But I don't mean I don't

[54:00] Single vs Double Opt-In Debate
---

JONATHAN STARK:
mean by accident. Like you're like, oh, I should really look at this today. Or do you have it in your calendar? No, it's in the calendar. It's definitely more

JASON RESNICK:
frequent than once a month now because the list is growing. Right. So that's that's also something to consider. But if I get like a wave of like if all of a sudden I start getting sales notifications in Slack or something like that, then I'll be like, hmm, what was mentioned somewhere? Right. Or, you know, I will take a look at it intentionally if I see unusual activities, because I get no different notices in Slack for sales. I get if I get a certain number of when they start hitting that threshold in some cases, like services, I actually want to know, like if they're approaching it, because then I'll actually in some cases with the services side of things, take a look at what they're doing. I'll take a look at that subscriber. It actually pings my CRM as people start to approach that threshold. And so if I start to... What are they doing that's causing them

JONATHAN STARK:
to approach this threshold? The salesperson sequence. So if they get to like, let's just say for the sake of argument, they get to two instead of three. Three is the trigger. But if they get to two, it'll actually... I've created

JASON RESNICK:
a Zapier automation to kind of drop that person into my CRM.

JONATHAN STARK:
And what CRM do you use?

JASON RESNICK:
I use PipeDrive.

JONATHAN STARK:
Yeah, okay. Makes sense. All right. So and the reason there is because of capacity planning or?

JASON RESNICK:
Yeah. And also to see if like, you know, if somebody is a hotter lead, and they don't check their email as much.

JONATHAN STARK:
You might just go manually like, right. Yeah. Imagine that.

JASON RESNICK:
Yeah. And that's usually when I'd be like, well, how'd you do that? I get a reply like that. So.

JONATHAN STARK:
Okay. Cool. So like, I don't want to go too far down that rabbit hole. That feels very, very specific. So let's, I've got a couple of questions written down here. Maybe we could kind of talk about, I'd like to talk about the bigger picture animation stuff, like the animation, the bigger automation stuff that you're doing, if you want to talk about that. Even though that's definitely, that's definitely like super edge case for people listening. But I do, I think if anybody listened this far, they might be interested in the kind of like two year long campaign concept and how much you can set it, forget it. If you want to talk about that, that'd be pretty cool. And then I've got some like lightning round questions that, you know, just for an expert like you, it'd be interesting to get your take on this like black magic stuff with email deliverability and stuff. Cool. Okay. So, so I don't think we talked about it on the other show. I think we talked about it after the show, but you know, you've got this sort of like big picture plan to take, I mean, how long have you been doing it? Since October of 2020. Okay. So coming up on two years, if I, if I know what year it is. Yes. Okay. So coming up on two years. So you're talking about, you know, not, you know, what is it? 600 emails maybe. Yeah. Something like that. Well, so 600 times two, because I got two lists. Oh, two lists. Oh my

JASON RESNICK:
God. And yeah. And if anybody wants to know about Jason's process for that, stay tuned for

JONATHAN STARK:
doing daily different podcasts that we're doing anyway. So the, what's the plan? So at a certain point you're like, I'm just repeating myself. Like there's no, this is mostly all evergreen. There's, I'm adding nothing new to my own thought leadership. I'm not drilling into any new rabbit holes here. This is, this is basic stuff localized for a particular audience. And I'm maybe getting bored, maybe just feeling repetitive, not, not growing intellectually, whatever, whatever the motivations are, that'd be interesting to know. And then, then what do you do? You know, do you just turn, you know, Ouroboros just like, if you get to the end, you go back to the beginning.

JASON RESNICK:
Sneaky. Yeah. So the sense was, was just that, like this is, I speak about evergreen things. And they're just understanding the subscribers awareness of their own email marketing. There would be times where somebody would jump on my list and I'd be having a quote unquote conversation like this, right. Through a number of days in email. And they'd be like, I'm just looking to grow my list. Do you have any resource around that? And so I, I'm a, I suck at blogging. I don't blog. It's just one of those things. And yet I have written tons of emails about that. And so for me, I was like, okay, banger emails, like what are the best of kind of things on the pillar topics that I talk about? And let's put that into an evergreen newsletter, right. Which goes out six times a week. I've left space on Wednesdays and Saturdays and, you know, other days to be timely, right? So if there's something that happens in the news or something, you know, that like this podcast that I go on, at least I can talk about it when it releases and things of that nature. And so I've left space, but 80% of the emails that are going out were already successful and I could even improve them, right? Because I know what worked. I'm like, oh, okay, well, this other email wasn't as successful, but it definitely emphasizes the point.

And if I lean it towards maybe improve the subject line or whatever the case may be, I can make it so much better. So what I've done was get back 20 minutes a day from writing those emails by putting them into evergreen. And that 20 minutes is now used to put people onto the list. So refocus my efforts on other things for the business that actually drives people into that list.

[60:00] Closing Remarks and Contact Information
---

JONATHAN STARK:
Yeah, it's funny. After we talked last time and you mentioned this, I think it was that night, I usually write my emails at night, where someone asked a question about the previous day's email. And I'm like, I know I've answered this before. So I Googled my own email, my site, found exactly what I remembered, and then tweaked it. It was good, but the tone was off. It was a ranty kind of email and this person had a real reasonable question. And so I kind of wrote a V2 of an old message from 2017, a five-year-old message. And I was like, that was actually pretty great. It was like, I wouldn't have said it any better if I did it off the top of my head. And having the starting point, like, oh, yeah, these are all good points. It's like someone else wrote it. But I feel no plagiarism. If it was someone else's, I would feel very plagiaristic. It was similar enough that it would have been plagiarism. But since it was mine, I was like, oh, I really, this was clear. It was good. The tone's off. So I fixed the tone and I shortened it. I deleted some stuff because it was a little bit of a ranty email. It got kind of sloppy. And I imagine it's an interesting way, if editing equals thinking. If I go back and look at something, because I had, again, it's like super evergreen stuff. It wasn't about what was happening in politics. So revise it and make it closer and closer to diamond hard.

Do that for a year. And it's like, jeez, if I tag these things, which I don't, other than just regular keyword searching, you know, it's like they're not tagged. But if you tagged them and put them into groups, it would be a very interesting thing to do, where you could kind of choose your own adventure. I'm super interested in advisory retainers and they click a link and they get literally 30 emails about the, you know, not a sequence really, like not a today we're going to learn about this and tomorrow we're going to learn about that. But like topical, almost like a book delivered over email, a short book delivered over email about this particular subject, which I was like, jeez, that totally was like, yeah, you definitely triggered that kind of thought.

JASON RESNICK:
To be honest, that's kind of where I see my evergreen going. So because I ask off of the back of an opt-in what their goal with email marketing is. And knowing that I could kind of carve that path for them. You know, if you're looking for list growth, yeah, you're looking for list growth ultimately to make sales, but sales is a little bit down the road maybe. Right. And so, um, yeah, I, for me, I'm trying to get to an evergreen newsletter of one year, then take stock on all different, on my pillar topics. And once I do that, then take a look at that and then put people, then basically write an email to the list saying, Hey, what is your goal with email marketing? And basically let them plink of themselves down into the sequence that they go into just reshuffling the emails that I've already already written. Yeah. So just for the

JONATHAN STARK:
person listening, the thing that I fear about this is that I actually enjoy, it's almost meditative for me, the daily writing practice. So if I was going for me, I'm not actually planning on doing this anytime soon, but a thing that has occurred to me to do is to, I've got my system set up in a very unusual way that I wouldn't recommend, but that a developer might do, so that I could mark a bunch of evergreen emails that I've already sent and any day that I, whatever, it doesn't happen that often, but I've missed a day here and there, any day that I haven't sent an email by midnight, it sends a best of email, where it's like, where I'm racing against my own robot to write something, so then it's a little bit more, because you'll get my, people get my emails anytime at night, could be three in the morning.

JASON RESNICK:
I think I get yours at like four o'clock in the morning or something. I mean, I don't, I'm not usually up that late, but I am, I like to write them after the kids are

JONATHAN STARK:
asleep, so that's my, you know, which could be midnight, you know, once everybody's in bed, the dogs are away, and it's like, okay, now I can like really enjoy this, because I love doing it, I really do, but occasionally it's like, oh, there's family in town, you know, something, and you're just like, ah, you gotta like sneak away and dash off an email in five minutes, which I can do, and I don't mind, but that's not my favorite. I would almost rather know that I've got this robot that's going to pick a best of from 2018 and send that instead, so that would be, that's kind of like my, if I get hit by a bus, the mail just doesn't die. It's kind of creepy, actually, though, but a little bit, yeah, there's a book, there's a book called Damon that kind of gave me the idea, a sci-fi book. Yeah, I mean, for me, the fear was

JASON RESNICK:
two, actually. One, does somebody recognize an email, and two, right, so like, in other words, when I like, if I repeated an email that they already got, like, if they've been on my list for a little while, what I did was I basically dumped, took the bucket and dumped everybody in the top again, so that was one, and the second one was how do I address the timely stuff or pitching things during, which, you know, like if I said, you know, September 1st rolls around, I want to run a sale just because, you know, for whatever reason. Yeah, see, I know how I would do

JONATHAN STARK:
this. Yeah, so how would you do it? You do it with the Wednesdays and Saturdays. That goes for the timely stuff. The other bit of it is a content snippet, so it was just thinking about that,

JASON RESNICK:
because ultimately, really what I wanted to do was I wanted to get my time back, because I had already built the practice. I don't, I like writing. I like writing the thing, but I was just like, I actually wanted to make the experience better for the individuals, right, and so with the end goal in mind of, you know, at some point in time where it's this choose-your-own-adventure style kind of thing, which I did with a podcast, and it worked pretty well. What? Yeah, so.

JONATHAN STARK:
How the heck did you do that? I mean, it was the email list for that podcast, right? Okay. So they would, they would opt in, and then they get a series of emails that were related to the topic that they selected, but it was links to those podcasts. Oh man, that is so interesting, but what was, was that a nightmare? It was cool, and people loved

JASON RESNICK:
it, because like they got the answers that they were looking for, and so I was like, I've always kept that in the back of my mind of like, if I could just do that for email, like not necessarily a podcast, but same idea, topic, topical groups, like you were saying, like a book, and deliver that, maybe that's the best approach, and so that's where my ultimate goal is to get to, obviously a ton of content, right, and so I have the content already. Now I just kind of got to tweak it a little bit, and you know, but once the thing is built, yeah, yeah, and that's, that's what it is. I mean, I guess I'm like, right now I'm building the evergreen ahead of the cars, right, on the road, so yeah, yeah, you know, I've got a nice buffer, but at the same time it's like, okay, there's this evaluation that I'm always doing, and I do it like every other week now to get like a bunch of emails loaded into the evergreen, where I'm like, okay, I remember putting, okay, so like really getting the pillar topics in the evergreen to see how that, to see how that works, and what's interesting is like, I look at it, opens and clicks, like the same people got that same email, and better results, like better metrics, right, and I'm like, that's interesting, okay. Yeah, I've talked to, I've talked to one person who has already done this,

JONATHAN STARK:
I've only, I only know one person who's done this, and, and I was on his list, daily list, and he had a really unusual message one day, he just told this really, really visual, unusual story from his life, and I replied, I was like, I am positive, I read this before, did I read it on your blog or something, and he laughed, he was like, no, I just dumped everybody back into the beginning of the sequence, and you're the first person to notice it, or at least reply and say that they noticed it, but it was, it was really, it was a very, it was a notable email, it wasn't like, you know, it was like really easy to be like, oh, I've definitely heard the story, it was a story, so it was like, I definitely read it.

And what's funny is like, see, I did something really more direct, I linked to a tweet that obviously had a date on it, and I said, hey, they replied to me yesterday, well, that date was months ago, so I was like, I had somebody reply back to me saying, maybe you sent this out before or something, like, you know, so, but for me, the stories tell a lot, and I'm pretty active on Twitter anyway, and people might find that it is familiar, maybe they did get that email twice, but I share stories on Twitter a lot, and things like podcasts and things of that nature, so I'm not overly concerned with, and I don't share like, something like what you mentioned, like some, like, yeah, that's stuck in my mind, you know, like, but yeah, for me, it's more, I was just worried that initially that people were going to notice, and that was like, I just did a test, I was like, all right, I'm going to take 30 days, I'm going to dump email people into a 30-day sequence of past emails and see what happens, and nobody, nobody said anything, in fact, people replied to the same email that they replied to the first time, which was funny, so for me, that was like, all right, this is validating something, but whatever.

JASON RESNICK:
Yeah, yeah, they, yeah, so like, I was going to say, you know, probably 50% or more people didn't read it the first time anyway, and then, but now you're saying, like, even the ones that did,

JONATHAN STARK:
they had the same reaction. Yeah, which is funny, because I, I checked, I haven't checked in a while, but initially, when I put everybody through, I started like, okay, if they had already subscribed at this date, then let me see if they opened it beforehand, and I kind of did like a little thing, and it was like a 50-50 shot, and you know, let's be honest, I mean, everybody's busy, and if I'm sending daily emails anyway, people aren't going to remember what I sent to them three, three weeks ago, you know, so. Yeah, never mind three years ago. All right, so let's, let's, I know we got to wrap up, so let's talk about, I got a couple of lightning rounds, this might be a rabbit hole, so we'll just try and, like, we don't need to go into, like, a giant soapbox, we can point people with links to, because I know you've written about this, but the first one, maybe this will be a short question, I've gotten, I've gotten hit with form spam a couple times, because I had single opt-in, we're going to talk about double opt-in next, so, so I had, all my forms were single opt-in for years. And a couple times I got some kind of form spam. Do you know why anyone would bother doing that?

JASON RESNICK:
Why does somebody do that? But there's nothing, no, there's nothing in it. They just subscribe. They're not sending me email. What they're trying to figure out is how they can use your brand in phishing attacks elsewhere. So they're looking for the reply. Yeah, they're looking to see one, if your server is exposed, then maybe they can use that in their network of spammer, spam kind of things, right? So they get to get headers back when you reply, you know, or to respond back or whatever. So they could see headers and IP addresses and things of that nature. But two, to see like if Jonathan Stark, you know, your, your brand, your domain, your email address and all that kind of thing, they can use and send emails on your behalf.

JONATHAN STARK:
So they're looking for authentication. Yeah. All that stuff. Okay. Okay. But why would they send 5,000? They could just, I don't know. It's a script kitty. I mean, I guess basically they're

JASON RESNICK:
trying what, and this is the only thing that I can equate it to because I don't, again, that's like the other side of the coin on email. And I've never ventured down that road, but when you use a tool like Glock apps, and this is a tool that, that helps you with deliverability, it scans your emails, scans your list. It basically tells you, you know, if your email is going to get delivered in the inbox or promotion or blocked by spam assassin or whatever, but you get a, an email list back, a seed list that you put into your ESP and you send an email to that seed list and Glock apps spits back a report. And they're all their email addresses that they control. And what each email address is tied to, is it like an individual client? So like Outlook is for this and Yahoo's for this and Gmail's for that custom domain there and so on and so forth. So kind of see how your thing lands in the inbox on those various different clients. So my thought is, is when somebody's doing that, they're trying to see the same sort of thing. Like if they send 50 emails into your list, they're also monitoring clients from a scripting level on their end to see, Oh, okay. Jonathan's landing in the inbox in every client. We got to use that, you know? And that's a gut feel. I don't know if that's why, but that's my, my assumption on that.

I got a new one recently where, where they don't, they, they subscribe

JONATHAN STARK:
and then they reply. Like they have a bot that's replying, which is bizarre. I've had that, but it's like, they don't reply anything. It's just, they reply. They're replying nothing. Or it says for this to Rebecca at, and then nothing, there's no link. There's no, there's nothing for me to click. It's not some kind of phishing thing. It's bizarre. And it must've been, it must be reasonably difficult to code. So it's like, what the hell are they doing? I'm not sure. Anyway. Okay. So that, that leads me to my next question, which is single opt-in or double opt-in. Yeah. This is another episode, but I'll try to keep it concise.

JASON RESNICK:
Yeah. We can link to your.

JONATHAN STARK:
Yeah. So, and I've got a Twitter thread that goes pretty deep into this, but basically what,

JASON RESNICK:
what it is is the, I look at double opt-in always, but with a twist, not the default crappy double opt-in that every ESP gives you as a checkbox. I look at things like that are custom built, like what the morning brew did or the hustle or courts or any of these news outlets, these publishers that based their engagement on that opt-in. So they hold real true to, you know, I mean, the morning brew, I think it's 18 days. If you opt in and 18 days, you haven't clicked on something you got. And so that's, I've modeled that and I've built that model into my own list, as well as my clients list on certain platforms, because you can do it there. Um, but so, yeah, so for me, all the forms are single opt-in, but there's a double opt-in behind that, that doesn't give that, you know, Hey, go click an email, you know, confirm.

JONATHAN STARK:
Yeah. That's I, I first, I hate those as a subscriber and their nightmare as a publisher because they go to spam so much and, you know, or people forget or whatever. And it's like, they had the impulse, like give them the email they asked for. They asked for the email to give it to them. And, but when you get, you know, 8,000 opt-ins or 10,000 opt-ins in two days, something's wrong. And, and you're paying for that and it's garbage. And even if you run it through a validator, they might be valid, but there are still bots. What I would do in that case though, is I would add, you know, at least if that's not the norm, right. Um, then I would

JASON RESNICK:
add a recapture to it or something of that nature. I wouldn't go re-architect the backend to go double opt-in. Um, but yeah, that's a pain in the neck. Um, I get it, but I look at it like, you know, the morning brew has 4 million email addresses or something like that. I mean, who knows what the actual number is, but it's, it's in the millions and they're getting their whole model, their business models based off of referrals. So if they can do it right, we all have ESPs that give us the metrics to actually measure that stuff. Why can't,

JONATHAN STARK:
why can't we do it? Um, yeah. So I, I turned on double opt-in for my, all my forms just, but I knew it was gonna be temporary. And I love this idea of, of like, look, if you haven't clicked something in 18 emails, then you're probably not gonna, you know, you're either a bot or something. And yeah, I guess there's some like link followers in corporate that kind of like make clicks look real or something. I suppose it could be gamed, but, uh, I'd rather play that game and go back to the single opt-in. I recapture makes me want to vomit. I'd rather have, I'd rather have robots on my list and pay for them. And I get why, like the study that I did was basically to understand how double opt-in versus single opt-in affects the number of subscribers on your list. And I studied six months worth of data across 115 forms. And it was about 34% of those that opt-in to double opt-in got stuck in that purgatory. Like they were just, you know, they didn't, yeah. And you can't email. Yeah. You're locked out. And, and, you know, like Drip has one retry and other platforms have one retry. CovertKit has none. If they missed that email, they're done, you know? And I was like, this is, this, I mean, you, you either paid if you're doing paid ads or you're spending a ton of time on content organically to drive these emails. And a third of them are lost. And so for me, yeah.

And when I did the study and I reversed on these 115 to the single opt-in with the time based engagement, it went anywhere between two and 10%, basically dropped to the two or 10% of those emails that opted in were bogus. And so you just have a pruning process that goes off the back of that, either through that time-based thing. If they're, you know, somebody fat fingered. Their email address or whatever, and it just bounces all the time. And that's the other thing too. Most of these ESPs, they bounce. If it's a bounce, they unsubscribed them anyway. So I don't, you know, Yeah, I'm not worried about those. Those are, those are not a problem. It's the ones that it's, it's differentiating a real person from a bot. That's the problem. I've heard, and I've seen Klaviyo now can tell you as the business owner, whether somebody is reading it on an iOS device or not, which that's kind of, I mean, that's been the biggest wave landing on email marketers desk in the past year was their iOS update because of the privacy protection. Now, if I could tell that they're using privacy protection, then I can lump them into a segment that way. And what I've gotten from, you know, other ESPs in the past until I found that Klaviyo thing, that, that was impossible to do, to detect that. I'm like, well, now Klaviyo does it, so they're doing it. There's a way, right?

So, so yeah, I mean, double opt in for me. I, and the goal goes back to that same idea of the experience with the subscriber. Like just to do that handshake dance kind of thing. It's just annoying. And like, there's gotta be a better way. We want to innovate that. So. Right. Cool. This has been amazing. We could probably go for another hour, but, you know, tell, tell people where they can go find out more, where's the best place to go. Yeah.

JASON RESNICK:
You can find me on Twitter. I'm at res with three Zs on Twitter. My DMs are open there, or you can go to nurture kit.co and you can find out all about email marketing.

JONATHAN STARK:
Killer. Go do it. If you're sending an email, go check it out. If you're not sending email, what is wrong with you? Yeah. Don't be, I don't, like I said at the top, that was my first regret. Yeah. I've heard it from so many people. Why didn't I start this earlier? All right, gang, that is it for this week. I'm Jonathan Stark and I hope you join me again next time for ditching hourly. Bye. Hey, Jonathan, again, before we go, I've got a quick heads up for you. On Tuesday, September 8th, 2026 at noon Eastern time, I'm running a live workshop called positioning for soloists who are having a hard time niching down. If you know you need to niche down, but you've been hesitating because you're afraid of picking the wrong one, cutting off good opportunities or boxing yourself in, this is the workshop for you. You don't need more convincing that vague positioning is a problem. You need a way to make positioning feel less risky. So you can finally choose a direction, test it in the market and adjust without blowing up your business. That's what we'll do in this workshop. It's the second session of my fall 2026 soloist growth workshop series for expertise based business owners. Just like you live attendance is limited to 20. So don't wait. Details are at Jonathan stark.com slash SGS, or just click on the link in the show notes.

That URL again is Jonathan stark.com slash SGS hope to see you live in zoom on Tuesday, September 8th.