Are small tweaks in your marketing strategy costing you big wins? From email subject lines to debunking commonly-held myths, simple changes can unlock massive improvements.
Today we’re exploring the art of finding small changes with big impacts in marketing with Jay Schwedelson, Founder of SubjectLine.com, CEO of Outcome Media, and host of the Do This, Not That! podcast. We’ll discuss how research-backed insights fuel his success, myths holding marketers back, and more.
Jay Schwedelson is one of the top marketing experts in the U.S., renowned for providing marketers with the latest research-backed insights and best practices.
As the founder of SubjectLine.com, the top free subject-line rating tool globally, Jay has tested over 15 million subject lines, helping organizations master impactful email
marketing. He also founded GURU Media Hub, which hosts the GURU conference, the world’s largest email marketing event, and other major marketing gatherings attracting over 50,000 attendees annually.
Jay’s podcast, “Do This, Not That!: For Marketers,” consistently ranks in the top 10 of over 50,000 marketing podcasts in the U.S. and is in the top 0.5% of podcasts globally.
Through his agency, Outcome Media, Jay’s team executes over 40,000 marketing campaigns each year for iconic brands. He has been named to Crain’s Top 100 Industry
Leaders for 10 consecutive years and is in the Hall of Fame at the University of Florida College of Journalism and Communications.
With his unique blend of expertise, Jay shares super tactical tips on marketing, specifically email marketing, content marketing, and LinkedIn strategies.
RESOURCES
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Connect with Greg on LinkedIn: https://www.linkedin.com/in/gregkihlstrom
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Transcript
Note: This was AI-generated and only lightly edited
Greg Kihlstrom:
Now let’s get on to the show. Are small tweaks in your marketing strategy costing you big wins? From email subject lines to debunking commonly held myths, simple changes can unlock massive improvements. Today, we’re exploring the art of finding small changes with big impacts in marketing with Jay Schwedelson, founder of subjectline.com, CEO of Outcome Media, and host of the Do This, Not That podcast. Jay, welcome to the show. Super excited to be here. Thanks for having me. Yeah, looking forward to this. Why don’t we get started? I know I gave a brief intro, but why don’t we get started with you giving a little background on yourself and your current roles?
Jay Schwedelson: Yeah. So I have an agency that I’ve had forever called outcome media. I’m down here in South Florida, about a hundred or so person firm. And for the longest time I’ve had that agency. And originally when I got going, I had a really hard time getting clients because I presented myself as an agency that did everything, email, direct mail, print, digital, whatever. And I quickly learned that if I wasn’t known for some kind of a channel that I wouldn’t get any business. So one night sitting on my couch, a million years ago, I registered the domain. subject line.com thinking that, all right, maybe I’ll try to be known for email because nobody was really doing that back then. And that kind of, uh, we made a free tool, people started using it. We became known for email and it really helped my agency a lot. So that’s how I got into the world of, of kind of the email world and subject line.com and all these other things. Um, and it kind of took me down the rabbit hole of this idea of small changes, big impact, as opposed to always looking for the home run swing. And that’s kind of been my, uh, I guess that’s my origin story.
Greg Kihlstrom: Yeah. Yeah, great. Yeah. I, um, as a recovering agency owner myself, I did not specialize like that. And you know, it was all, it was always, it was a tough thing to say, okay, I’m not going to do stuff. Cause I, I think like a lot of people, like a lot of different things and like variety, but I found that even in the little ways that I specialized, I became more successful, um, as opposed to just trying to be everything to everyone. Right. So, yeah.
Jay Schwedelson: Yeah. Yeah. I always found, I, what I realized is at first I shied away from being known for something. I was if I’m known for something, it’s like pigeonholing me, how am I going to ever get the other business. But then I realized if I’m not known for something, I’m known for nothing. And then I get nothing. So it’s kind of like this, this email stuff is a backdoor into all the other stuff that we do. And so I’ve leaned in to try to be known for something. So that way, when I’m not in the room, and they bring up, you know, email, it’s like, Oh, that guy, Jay, maybe he’s not an idiot, we should work with him. And so that has helped me a lot in kind of growing my overall business.
Greg Kihlstrom: Yeah, yeah. Love it. Well, yeah, let’s, uh, let’s dive in here. I want to talk about a few things with you, but the first thing is kind of building on, on what we were just talking about and. This idea of focusing, but also on making small and incremental changes. And so, you know, much, uh, I’m a, I’m a. fan of agile approaches here. So I like this, this concept here, but you know, you’ve, as you just said, you’ve built a reputation for email and, you know, subject line.com, you know, so making small changes, subject line tweaks, and yet delivering big results with those small changes. Can you share, you know, what are, you know, some of the more impactful small adjustments that marketers can make along those lines?
Jay Schwedelson: Yeah, you know, oftentimes people that email marketing may say, Oh, it doesn’t work for me. I’ll say, well, you’re not focused on these little things that I could have a big impact. And marketers generally have a backwards, they’ll work on their creative or their copy, and their offer and everything inside the email. And then they spend no time on their subject line when if you don’t get it open, in my opinion, who actually cares what’s in the email, right? So believe it or not, there are very, very little things that cost you nothing that take no time that you can do in your subject line that can significantly change the number of people that are opening up your emails. And one of the biggest things that people don’t realize is nobody reads the whole subject line. They don’t. You could literally put at the end of the subject line, Greg is super uncool and no one would ever see that because they don’t read the whole thing. They read the first few characters, maybe the first word or two. and then they decide whether they’re going to go further. So what you put in those first few characters is everything. So for example, if you start your subject line with a number, you know, the seven pitfalls to avoid, the three biggest trends in fashion, whatever it is, a number as the first character, a numerical number actually will lift your open rate, the percentage of people opening up your email by over 15% than if you didn’t start it. you know, with a number. Why? Because when you’re doing that social scroll in your inbox, that little thing, that millisecond that somebody pauses and grabs our attention, those first few characters is what’s going to be the game changer. Other things that you could do in the first few characters, for example, is capitalizing the entire first word or phrase of your subject line, not just the first letter of the word. If you write the word new, N-E-W, maybe it’s new guide, you capitalize the whole thing. Or big sale, if you’re on the consumer side. Every letter in those words or phrases are capitalized. Again, it’s that millisecond pause that grabs their attention. Or even emoji. As silly as they sound, they’re a graphical symbol that will get you to pause. And you don’t need to use a smiley face. You could use a calendar. You could use a checkmark. You could use whatever. And all these things allow you to grab that attention. And the things that you always want to be saying to yourself, what am I doing to get my email opened and not everybody else’s? And the world has changed. People think, oh, if I use an emoji, if I capitalize a word, if I do use a number, I’m going to the junk folder or spam folder. That’s information from 10 years ago. That’s not the case anymore. That’s not why you go to the junk folder or spam folder. So I would focus a lot of energy at the start of your subject line.
Greg Kihlstrom: Yeah. Yeah. And so, you know, with your, with your agency had over 40,000 marketing campaigns, that’s a lot. Um, so I’m sure you’ve seen some, some overall trends, but you know, what’s something like surprising or that you wouldn’t have expected. I would imagine with that volume, you’ve seen a lot of different things too. You know, what’s, what’s something that surprising that maybe most marketers overlook.
Jay Schwedelson: You know, I think that the odd thing, especially about email, is how much it changes. You think about email’s been here forever. It’s a legacy channel. How much can it really change? But the odd thing is it is always changing. I’ll give you a great example. If you rewind a year or so ago, personalization in the subject line, if I wrote Greg comma, check out this whatever, actually putting the person’s first name in the subject line would really increase the percentage of people that open up the email because like, Oh, this is for me. It’s not for everybody else. But like all great tactics, what marketers do is once they see somebody doing it, it works. Everybody copies each other, right? So now if you go to your inbox, it is not it is wallpaper to see your own first name in that subject line, so much so that for the first time ever, and this is just in the last six months, that first name personalization in the subject line actually depresses performance, it actually hurts your performance. So instead of doing first name personalization, the type of personalization now, that’s working really well, especially in the subject line, is this idea of telling people who they are. So for example, if you’re a business marketer, In the subject line, you would put something like their industry, you know, just for people in the retail sector or their job title, what CFOs need to know. And if you’re a CFO, you’re like, wait a minute, I need to open this up. You see yourself in that subject line. So personalization with their function or title, or even your company, you know, is Acme at risk. I work at Acme. I need to check that out. Or on the consumer side, you know, just for DIYers, just for people in Miami, for golf enthusiasts. So personalization beyond the name in the subject line, is really driving massive, massive lift in engagement. And so this idea that email is not this static channel, I think is a really important concept for marketers to kind of wrap their mind around.
Greg Kihlstrom: Yeah. And I mean, is that do you see this just continuing as like, there’s always gonna be like, so now people listening to the show and to your show, they know that trick, right? So they’re, they’re gonna get amazing results for, I don’t know, like 90 days, 120 days, and then the next thing or whatever. So is that I guess two questions there. I mean, is this kind of just the way that it is? Like, we’ve always got to be kind of, you know, finding the next thing. And how do you approach finding like, is there have you in the in the years you’ve been doing this and very successful at doing this? Is there kind of a way that you think about, okay, it’s it’s kind of time to find the next thing? Or how do you think about that?
Jay Schwedelson: Yeah, it is always time to find the next thing. And things are always evolving a little bit technology, especially in email is always changing, you know, a little bit about what you can do. Right. So for example, the from name field, when you send out an email, let’s say coming from your brand, you know, coming from Acme, coming from Nike, right, that from name, when you send it out, there’s a from address that you send it from, you don’t want to mess with that. But the actual from name, the alias or the friendly from that used to be something that we never touched. If you’re Nike, it’s just coming from the word Nike. But if you go to your inbox now, what you will see is that there’s been a lot of testing and trending towards treating your from name is almost the start of your subject line where we’d say, you know, Nike, big sale, or, you know, if you’re a business brand, you know, Acme webinar. where they’re actually inserting whatever the offer is as part of the from name and changing that every time they hit send. That’s not something that anybody was doing a year, two years ago, really. And it’s this kind of new tactic. And now when you layer in what’s going on with AI, and how AI now is beginning to bucket our emails that we’re sending into these different buckets, you know, in your promotions tab, whether you’re an Apple or Gmail or whatever, Trying to be a marketer that reacts to what what allows you to go into this bucket versus this bucket It’s another one of these game-changer moments. So we always are iterating always changing always trying to keep up You know one step ahead if possible
Greg Kihlstrom: And so, you know, there’s some marketers, at least out there that are, I would say, pretty scientific in their approach. And, you know, they follow the data and all that. I would say that there’s possibly a larger percentage that are not as much as marketing, I believe, is a data driven, you know, profession and all that. There’s a lot of let’s call them like urban legends out there as far as, you know, myths and things that people just kind of glom on to, you know, the here at once, and then that’s the truth. And maybe it’s, it’s even along the lines of what you’re talking about here, which it was something that was true in, you know, 2005, but no longer true or now, but, you know, what, what kind of myths do you run into, you know, whether it’s from, you know, talking with other people, clients, or whatever that that are still kind of prevalent, but untrue.
Jay Schwedelson: Yeah, that’s a really great point that you bring up. I think one of the biggest things, and I’ve mentioned a few times now in our discussion, this idea of open rates, you know, somebody out there is listening and they’re saying, well, open rates are garbage. And what is an open rate? You send out a hundred thousand emails, you go into your tool and it says you have a 30% open rate. And that means that 30% of the people opened up your email. And a lot of people say, well, open rates are garbage. They’re inflated because of bots, because automatic opens because of all these things. And that’s true. Right. And so this myth that no one should pay attention, their open rate is total garbage. In my opinion, the reason being is while the number that you see in your tool, it doesn’t matter what tool you use is not accurate. You don’t really have a 30% open rate in that example, because of all the things I said. What is true about your open rate is that it’s incredibly important metric as a directional metric. What do I mean? When you send out an email, for example, and you do a test, okay, that guy, Jay, who talked too fast, he said to try an emoji. So I’m going to do that, right? Version A has an emoji in the subject line, version B doesn’t. And version A with the emoji has a 40% open rate. But version B that doesn’t has a 20% open rate. That doesn’t mean 40% or 20% open yet. But it does mean directionally, the one with the emoji did better, right? It’s almost like a survey on your tactic that you’re doing. So when people say open rates are meaningless and garbage, because they’re not an accurate metric anymore, that is a ridiculous thing, in my opinion, because directionally, they’re really valuable. And I think one of the biggest myths that are out there, this idea of spam trigger word lists, it drives me crazy. If you go on Google right now and say, spam trigger word lists, They’re gonna be all these lists coming out the 2025 spam trigger word list. These are the words that if you put in your subject line, your body copy, you’re going to go to the junk or spam folder that is based on technology from 10 to 15 years ago, because the receiving email infrastructures had no other way to figure out what was garbage and words like free were really being sent out by the bad guys. But now the reason you stay in the inbox for us to go to the junk or spam folder is based on engagement. How often is somebody open or clicking on your emails that you’re sending? And if they are, they’re going to, you’re going to stay in that inbox. It’s not because of the words. And ironically, the very words that people avoid by these spam trigger word lists that are total garbage, like words like free are what generate more engagement generate more opens, which ironically cause you to stay in the inbox, right? So there’s a and the problem in general is that we are very lazy in marketing, we regurgitate information, best practice information, by the time it’s a best practice is probably out of date and something you should retest and almost avoid. That’s the nature of a lot of best practices.
Greg Kihlstrom: Yeah, so I mean, this kind of goes back to the earlier point as well. But you know, so how how do you look at being data driven that I mean, it sounds like a lot of and rightfully so like a lot of what you’re doing is like questioning assumptions, looking at the numbers and seeing what the numbers actually say versus what, you know, you Google and find out so like, how much how much focus do you put on on the the data part of the business?
Jay Schwedelson: Yeah, that’s a lot. And I’ll tell you, even listening to me, I wouldn’t believe a word that I say everything is about testing always. And retesting. I hate, for example, industry averages, what are the industry average, whatever’s, you know, click through rates, or what? I hate that. Because You’re your own brand, you’re in a sub-industry, you’re going after a certain type of customer, you’re a certain type of offer, certain type of brand, certain type of everything. Industry averages for anything are completely meaningless in my opinion. And anything that you hear in a podcast like this or anywhere else, I think it’s all about getting ideas that you can test. And then you want to create your own benchmarks. I always think about data as being like a swimmer or weightlifter, right? I don’t care what other companies do. I’m just trying to beat myself. And I want to benchmark everything and even benchmark within benchmarks. So if you think about email, for example, people make the mistake, oh, our emails get, you know, this click through rate and this open rate and this response rate, and this is email. Right? And that’s ridiculous. Same thing for social media, our social posts, get this many engagements, whatever wrong, you want to bucket them because within them, there are buckets, right? So you have what type of emails you send out, transactional emails, promotional emails, email newsletters, onboarding, welcome emails, social posts, maybe you’re doing, you know, something, you’re promoting a new piece of content, maybe you’re promoting a webinar, you want to take them all put into different buckets. And then you want to benchmark the performance within those buckets. Because the reaction to your email newsletter is very different than the reaction to when you’re promoting a webinar or a new sale. So you want to benchmark within each category, and then be yourself as best as you can every single time. And we are testing every single day.
Greg Kihlstrom: Yeah, Yeah, I love that. Yeah. And I love the, the idea that yeah, we’re, we’re kind of here to provide some ideas and not Yeah, not prescriptive, right? I mean, that’s, there’s too many details to just throw something out and say that it applies to everybody, right? Yeah, always. So I want to switch gears a little bit here and talk a little bit about some of the other things that you’re doing as well. So you know, we talked about subject line calm and your agency outcome media. You also have a podcast called do this, not that. And you also run a conference. So you do a couple things. You’re right. You like to stay busy. I respect that. how do you look at the relationship between these things? There seems to be some obvious through lines, perhaps, but how do you look at and maybe why do you do all this and how do they complement each other?
Jay Schwedelson: Yeah, it’s a good question. I should ask my wife that question, because she asks me that all the time, actually. I think what I’ve landed on the last few years, without any type of real analysis behind it, is I think attribution is garbage. I know that’s a big, loaded statement. But the reason I say that is I think that marketing is no longer transactional, that you do a webinar, someone attends, they become a client, or whatever. I think there’s this idea of surround sound. right, where you are consuming content from a company or a person or maybe a brand that has a person that’s kind of like leading that brand, you’re consuming their content, you’re seeing them here, there, wherever you’re getting tidbits everywhere. And then when it comes time for you to be in market, for that product or service, they are in the shortlist in your brain for that thing. And so this idea of surround sound to me, I think is really important in this world of AI and this tidal wave of garbage. And so that’s why, you know, I have a podcast where I put out five episodes a week, which is hard, right? I have a newsletter, I have multiple virtual conferences, we do all this stuff. So that way, we are top of mind when the time comes. And I think while it’s hard, and it’s not sustainable, and I’m losing my mind, I do think that that’s the world that we’re in now where attribution, it’s, you’re gonna have a very hard time, I think that for market, it says, I’m going to do this, and it’s going to result in that. I think that that ship is sort of sailed a little bit, maybe I’m often saying that.
Greg Kihlstrom: No, I mean, personally, I totally agree. And it’s, it’s why I try to do a few different things myself. I mean, it, it kind of reminds me of like the, um, the B2B equivalent of like the cinematic universe kind of thing, you know, like the Marvel universe or whatever. It’s like, cause I think B2B, you know, Speaking to a B2B audience, primarily it’s their consumers in real life too, right? And they’re consuming Omnichannel. And to your point, they want to go to events, they want to listen to a podcast in the morning or whenever they take some time. And And stuff like that. And so yeah, I mean, being it’s kind of like, what I tell brands that I work with, like, you kind of have to be where your customers are, and your customers are everywhere, right? Right. Exactly. Yeah. So I mean, I guess what what lessons could marketers take from from this approach? I mean, you know what, they’re probably on multiple channels, but are they thinking about multiple channels in the right way, from your perspective?
Jay Schwedelson: Yeah, I think a lot of times markers are checking a box. So with social media, like, okay, we posted on LinkedIn, we posted here, we did that with this piece of content. Great. We got our newsletter out. Great. And they’re checking a box that they’re doing the thing, but they’re not really being intentional and make that thing particularly good, which I think is an Epic waste of time. And I also think there are things like a negative signal where you’re putting out kind of half bay content. and people aren’t really going to think of your brand a certain way. So I would really take a step back, and I would do two things. Number one, be very intentional about where you’re putting out your content, what you’re doing, and how. Like for me, I go heavy on LinkedIn. I go heavy with my podcast because that’s where we’re putting a lot of our energy, right? And then the biggest thing is I’m not the smartest dude in the world by far. I’m kind of clueless. But what I’ve learned is about consistency. If you are consistent, and you don’t stop, you’ll beat out 95% of the people that may be even better than you or smarter than you or bigger than you or whatever. And that’s like with your podcast or a newsletter or whatever it may be. You can’t stop or post it on social media. You just can’t stop. You can’t do it for three months, can’t do it for six months. You have to keep going. And that is ultimately I think how you win. And it’s not sustainable. It’s very, very hard. But doing the things that are not scalable, not sustainable, I think that that really is a recipe success. At least it has been for me.
Greg Kihlstrom: Yeah, yeah. Well, and, you know, kind of a follow on to that. And first, you know, thanks so much for joining today. I’ve got one last question that I like to ask everybody on the show. You know, what do you do to stay agile in your role? And how do you find a way to do it consistently?
Jay Schwedelson: That’s a big question, right? Um, I’m a big believer that you have to be a part of all the pieces of your company that you’re, you know, whether you own it or not or whatever. So if you’re in marketing, sit in on sales calls. Okay, if you’re in sales, try to sit in on a marketing meeting, sit in on client services calls, right? Here what the complaints are, I do this all the time, sit in on as many different departments that you’re not a part of all the time, because that is if you get too far removed from that, you’re not going to know what’s going on, you’re not going to know how to react, you’re not going to have to grow your business, grow your brand grow your things. So don’t remove yourselves from the daily stuff and step out of your zone into other zones. And that for me has allowed me to stay agile.
