In this episode of Your Dream Business Podcast, Teresa Heath-Wareing sits down with email marketing expert Jay Schwedelson for a deep dive into the tactics and tools that can supercharge your email marketing strategy.
From writing irresistible subject lines to knowing the best times to hit send, Jay shares actionable tips that can immediately boost your open and click-through rates. They also explore how AI is transforming email campaigns—from smarter automations to more effective personalization. Plus, you’ll learn why weekends might just be your secret email weapon.
Jay also gives an inside look at his innovative Guru Conference and how he’s revolutionizing the way we experience virtual summits—with humor, star power, and unforgettable value.
Whether you’re new to email marketing or looking to level up, this conversation is packed with expert insights you won’t want to miss.
KEY TAKEAWAYS COVERED IN THE PODCAST
Subject lines are everything. Jay explains how great subject lines are the #1 way to increase open rates—and shares real-world examples that work.
AI can make your emails smarter. From optimizing send times to refining content, AI tools are changing the way we approach email strategy.
Don’t underestimate weekend sends. Contrary to common myths, emails sent on Saturdays and Sundays often perform better—especially with the right audience.
Automation isn’t optional—it’s essential. Jay breaks down how automated email flows save time, re-engage cold leads, and drive long-term results.
Your CTA buttons matter more than you think. Personalized and benefit-driven call-to-actions get more clicks. Jay shares what to say (and what to avoid).
Email is still king—when done right. Relevancy, frequency, and personality are key to building lasting connections through your list.
If you enjoyed this episode then please feel free to go and share it on your social media or head over to Apple podcasts or Spotify and give me a review, I would be so very grateful.
Connect with Jay Schwedelson on Website, Linkedin, Instagram
Connect with Teresa on Website, (Grow, Launch, Sell), Sign up to Teresa's email list, Instagram, LinkedIn, or Facebook
Transcript
Teresa: We all know that we should be sending emails, but how do you maximize the emails that you're actually sending? Should you be putting emojis in the subject line? What day is really good for getting people to open and read your emails? And how can you use AI to write your emails today I am interviewing.
The amazingly smart and super funny, Jay Shri, and he's sharing all this one is not to be missed. Welcome to the Your Dream Business podcast. I'm your host, Teresa Heath, wearing an international bestselling author, award-winning speaker, TEDx speaker, certified coach, and the host of this number one ranked podcast.
I am so excited to guide you on the journey of creating a business and life that you not. Perfectly aligns with you and the season of life that you are in. In each episode, I'll share with you easy, actionable, and insightful strategies to grow your online business. Plus we'll be diving into some mindset, tools and strategies that keep you [00:01:00] focused, motivated, and are going to stop you from getting in your own way.
So if you're a course creator, membership owner, or coach, you are in the right place. Let's get started. Hello and welcome back. To another episode of the Your Dream Business Podcast. As always, I'm your host who, Heath Waring. And this week I have a great, great guest for you. I am smiling even just doing this intro because I've just been watching the video 'cause you'll know if you've listened to this podcast a while.
If you're new, welcome. I'm super, super glad you are here. I. Record, obviously I batch record the interviews and when I go to do the intros, I sometimes have to just go back and flick through the video and go yeah, remind myself again about some of the things we said and just check my notes and genuinely just even see the beginning of this interview making me smile and laugh.
'cause I. Fricking love this guy. Today I'm [00:02:00] interviewing the Amazing Jayton. Now I don't even think I've said it right this time. You will hear how I try and say it to him on the actual interview. He is well just fricking awesome for one, but two. An amazing marketer, right? Like, you know, that I geek out on, well, if you, if you're new, I'm just sharing, I geek out on all marketing, all funnels, all online stuff like numbers, stats, facts.
Like, I love it. Like my brain goes into overdrive when it's like, oh, that's clever. Oh, that's really cool marketing. I like what they did there. And Jay is like the best person to know about this stuff because he. Has got so much knowledge. He's so smart. He's very self-deprecating by the way, and you'll see this, like he often will, you know, say things that makes it like he knows nothing.
He knows. So much stuff. So Jay is actually the founder of a few different things. [00:03:00] So he has an agency that helps people with marketing, a big agency. He's also the founder of subject line.com, which basically if you need help coming up with a subject line, or sorry, I. Let me rephrase that. If you want to check your subject line, then basically you can put it in subject line.com and it'll tell you whether it's a good subject line or not.
And he is the founder of Guru Media, which basically is an events company and he does online events. So he does the guru conference, he did event testing, and he gets like. 30,000 people to these events. It's insane, literally insane. And the online events are like no online event I have ever, ever been to or witnessed.
It's wild. The stuff they did, like they had live Sky day divers answering questions at event testing, like it was crazy. He's also very funny. And I just loved talking to him. I was actually on his podcast Do this, not that a few weeks back. So if you haven't listened to that, [00:04:00] please go and take a listen to his.
It's a real short podcast. Gives you really kind of practical, strategic, tactical stuff like mine does. But he manages to say it a lot quicker than I do. Uh, so his is short of the mine, but you are gonna come away with so many hints and tips and tactics that you can use like. Should you be putting an emoji in your subject line?
What days are best to send emails? This is so practical and things that you can take away today and do in your business today with no cost, and it's fun. We have so much fun. Honestly, I love this guy. He's awesome and you are gonna love him too. So without further ado, here's the awesome Jay. Welcome to the podcast, Jay Delson.
Have I said it right? Did I? You rushed it. Are you, are you sure? I, not even kidding. I have been practicing. Okay. Like this afternoon I got everything off my to-do list and went, this is all I can do. So I went and Googled God and I went God to LinkedIn, God. And I thought you would at least have the voice thing on your [00:05:00] LinkedIn.
Jay: Oh, I should do that. I should do that. You should. I should do that.
Teresa: Because it's not an easy name.
Jay: Listen, my name
Teresa: I, and that's coming from someone has a big name as well.
Jay: I just learned how to spell my last name like a week ago, so you know, it's not easy.
Teresa: That does not surprise me. Like it's hard. Anyway, Jay, welcome to the podcast.
Jay: Thanks for having me. It's an honor to be here.
Teresa: I am excited because I was saying to you before we got on that I am, and they'll know this, the listeners who listen regularly, I'm an all like geek, right? Numbers, facts, stats, like I love it all and. Do you know what? I just worked out that I wasn't on your personal email list.
I've been on the guru email list. Right. Okay. And I recommend it to everyone because it's one of the only emails. Now I, I've just signed up for your personal one by the way. Thanks. But it's one of the only ones that I literally open and read every time because there's always something gold in there.
There is always some like fact stat tip, and I love that.
Jay: I love hearing that. Yeah, [00:06:00] we try, you know, I'm a big believer in like the 10 foot level of stuff. Like what can you do and try right now that doesn't cost any money, that you don't need some special software tool or whatever, because those little things make a big difference and everyone's always talking about these big ideas.
It's like we need the little ideas.
Teresa: Yeah, totally. And there's something that you can tell me today and literally my next email, I can try it like, and I love that.
Yeah.
Okay. So you are renowned as like one of the world's best generally marketers, but email marketing is definitely your jam. Yeah. Is that like, are you just a geek for email marketing or did you accidentally get that and go on?
I better lean into this.
Jay: You know. Oh, it's fun. It's a, it's a funny thing. I don't consider myself any of those things. It's very kind of you to say that, and I'll tell you honestly how that happened. So I've had a, an agency forever, and when I've had this marketing agency forever, I was really struggling to get business early on.
And I would go into these pitches and I would say, I do 75 different things for a living. [00:07:00] Nobody would care. And then I was like, you know what? I, I'm not known for anything. I couldn't get any business. I said, I gotta double down in one area. So I said, you know, I doubled down an email 'cause maybe I get known for email.
I can get the business from my agency in all these other areas. And I said, how am I gonna do that? So I said, I need a website that people can use that would think that I know something about email. So this was years ago and I went, I bought the domain subject line.com for 500 bucks and I stuck up this ridiculous website where you can go and mess around with the subject lines and stuff.
And that did okay. And then what happened was like, oh. You are the dude who, who knows about subject lines. 'cause you have that website. Meanwhile, I didn't know anything at the time. I'm like, I'm an idiot. I didn't know anything. But then everyone kept saying, you're the subject line guy. I'm like, I, I better get better at this stuff.
And so over time, yeah, we started to really figure out and, and, and double down and all these different things and test a million things. So I appreciate you saying that. But it was almost like I was forced into trying to figure out how to do this stuff because I didn't, I liked eating [00:08:00] food and I didn't wanna go outta business.
Teresa: I love that. I love that. That's your main thing, like, yeah, I really like being able to eat food. Yes. So I probably need to figure this stuff out. Like, do you geek out on it now? Do you like, does it, yeah. Do you lie awake, like, Ooh, look at this. Like, is that, is that your job?
Jay: You know, it's almost like anything, whenever anybody, whatever sector anybody's in, you can't unsee it.
Like when I open up my inbox now and I'm looking at subject lines like, that's a good idea. That's horrendous. This won't work. This is gonna crush it, you know, and I'm always making a folder of like stuff I wanna try, but whatever industry or sector somebody's in, when you're on your social feed or whatever, you're like, oh, this is horrendous.
Nobody's gonna engage with that. I love this idea. I'm stealing this. You can't like turn your brain off from that content. So. To, it does get me excited. I show my wife, I'm like, look at this subject line. She goes, you are the biggest loser of all time. This is noting interesting. Did I marry you? Yeah. Right, right.
And then, but she's the dermatologist and then she'll show me on her phone, look how [00:09:00] disgusting this thing is, this cyst. I'm like, that's disgusting. Don't show me that. So it's like, you know, we show each other stuff, but neither one of us gonna see it.
Teresa: Evens. I, that's fine. That's good. Same with my husband.
He's a aircraft engineer and the minute he starts speaking, it's like I just go into this nod and grin. Mm-hmm. Like, yeah, yeah, yeah, yeah. I have no idea what he's talking about. Yeah. Literally none. And I think that's why relationships work so well. Right. A hundred percent. Like two different worlds. Two different lives.
I love it. Yes. Okay. So I said to you when we got on that, one thing I'm really good at is saying to everyone all the time, you need an email list. All the time. You need an email list. It's like one of the most important, powerful things that you can have in your business. I don't need to repeat that again, but one of the things I'm not great at is talking about how we manage and love those people on our email list, because it's one thing getting lots of good people on your email list.
So that's the first thing, not just getting any randoms. But what are we doing with them and how are we looking after [00:10:00] them? Like what, in your mind, what is the very basics that people should be doing? Like is there a number of emails they should be sending? And I mean like basic stuff Or is there how many times they should be doing it?
There are certain types of emails they should be doing. What? What kind of things do you see that
Jay: are working? So there's a few things I would think about. First off, I would think about the very, very first email that somebody gets from you. It's a very, it's the most important email and people have it backwards.
When I say the first email, someone signs up for your newsletter, someone buys your product, they give you their email address, and now you, that email goes to that person. It's not that you're establishing your brand or your tone, or your voice or any of that garbage when you are sending from your platform.
And I'm not gonna get technical, but you're hitting send from whatever platform you're using, and that person's receiving that email for the first time. There's this handshake that's happening between your sending platform and that person's receiving infrastructure. It could be Gmail Outlook, whatever.[00:11:00]
Now, if that person's receiving your email and they don't open and click on that first email that they get from you, mm-hmm. What you are telling your inbox, your provider is, Hey, I don't know who this new sender is. I don't care about them in the future, you could put 'em in the junk folder or the spam folder 'cause I don't even know why they send it to me.
That is what you are saying by not interacting with that first email. So the game is that first time you send somebody an email it, that subject line needs to be the most sensational subject line, outrageous subject line. You need them to open it. You need them to interact with it, because then you're gonna generate that signal.
To your own infrastructure saying, oh yeah, keep this in the inbox. So it's not, thank you for signing up. Not thank you for subscribing. Thank you for downloading. It's not a receipt that you're sending somebody. Yeah, it's, Hey, you're now a VIP. Check out what's inside.dot awesome to have you on board. This is just for you.
Special gift for new people, whatever. Get them to open and interact with that first [00:12:00] email because the likelihood of staying in the inbox, if they open and interact with that first email goes up by over 85% by doing that. So that's step one. I know I can just go on and on on. Do you want me to, let me, should I go further?
Teresa: Yes, go further.
Jay: Okay, so great. I think the biggest problem that we all have is, and, and we all talk about, we have people on our email database, right? Okay. I got, you know, thousands of people on my email database. Who cares? It's, are people interacting with your emails? Are they opening them? The weirdest stat in all of marketing is that we somehow think it's normal.
So let's say you have a database of 10,000 people on your file. Mm-hmm. Your list. Okay. And on average, you get. Maybe a 30% email open rate, 20%, 35, 40%. Why is it normal that the majority of people on your list. Over 50% are not opening your emails. And we're like, oh, that we did great. We got a 40% open rate. 60% of the people didn't open the email.
Yeah. Literally. Why are we, it's weird. Yeah. It's so strange. Like way to go. The [00:13:00] majority of people didn't like what we just did and like we high five each other and so odd. So I'm very, very focused on. Get the email open because who cares what's in your email? Who cares about your amazing offer, your copy, your content.
So I spend a lot of time and energy saying, okay, and that's why we started subject line.com. What are the things I could do in my subject line? And believe it or not, there's lots of little things, the easiest little things that will get my email open. 'cause every time you hit send, you're in a battle.
Mm-hmm. What am I gonna do to get my email opened and not all those other ones around me? And so, for example, people always ask me, well, how long should a subject line be? You know, how many characters should it be in my subject line? Should it be under 50? Under 60? It's the most ridiculous conversation in the world.
Nobody reads the whole subject line. You could put at the end of the subject line, Jay's a big loser. No one would see it. 'cause you don't actually read it? No. Okay. And so what you wanna think about is the first character, the first word, the first two words, [00:14:00] your subject line, because we do our social scroll in our inbox,...