The transcript below is available for those who prefer to read along. Please be aware that it may contain minor errors.

Grace Clark
I really appreciate you joining us. So I’m going to go ahead and kick us off. So today we’re here with Jay Scwedelson. If you could just introduce yourself in your own words to our audience today.

Jay Schwedelson
Sure. So I have an agency, a marketing agency that’s mildly boring, more fun stuff is my company puts on really large virtual marketing events. We put on one about email, since we’re talking about email called Guru Conference. It’s free, you should check it out. It’s fun. And then we have different websites like subject line.com where we’ve checked 15 million subject lines. It’s free, you can go there. It tells you how to write a subject line better. So we do all sorts of stuff trying to tell the marketing world how to just do stuff better from what we are trying out.

Grace Clark
Very cool. So to kind of get our conversation started, what would you say to B2B marketers who think that email is a dead platform?

Jay Schwedelson
Good luck to you because email is, in my opinion, your email database is the most important asset that your company has. There’s nothing else on planet earth that at any moment you could decide to communicate with the entire population of people that know and care about your business or that you want to communicate with. You can’t do it on social media. You can’t just do optimize your website and have it show up in the search engine for everyone to see. There’s no other way to do it. So if email’s not working for you, it’s not because email’s bad for the sector you’re in. You might not be paying attention to a lot of the little things that allow email to work and it’s worth investing in it because it can radically change your business.

Grace Clark
So with those little things that are worth investigating, where are some of the places that you would suggest someone get started to figure out what’s not quite working?

Jay Schwedelson
Well, when you think about sending out any email, it’s a chain of events and if any part of the chain breaks, then the person’s going to stop paying attention. So what I mean by that, you send it out, when did you send it out? What time of day, what day of the week? Great. Now you got there at the right time. Then they look at the from address, what’s the from address? Okay, I like it. Then I look at the subject line, what does it say? Do I like it? Open it up. Then the headline and so on and so forth. So you have to take each little step and feel confident that it’s pretty good because you’ll lose the person with each step. So what should you do to get started is to take a step back and look at the email and really simple be like, would I open this? Would I read this? Would I respond to it? And if the answer is no, then why not? And then try to adjust the things that are epically boring in your view.

We’re human beings and a lot of times, let’s say you’re in the B2B sector, you’re marketing to engineers, you’re like, okay, they’re very intellectual. They’re not going to get turned on by an emoji in the subject line or a funny word or a curiosity type of subject line or something really compelling in the headline. They just want to know the statistics and they want to know the trends that are kind of little nerdy, but that’s not reality. Everybody. We all have human behaviors. We all react to the same stuff. So being as human as you possibly can and injecting a curiosity and humor and suspense and fomo, this is what drives response. The basics of marketing.

Grace Clark
I like it. So with sending out emails to your audiences, how many emails would you say is too many emails to be sending someone?

Jay Schwedelson
The funny part about frequency is that I would guess the majority of people listening to this are not sending out enough and they’re probably saying, no, no, no, you don’t understand. I send out a lot. But really frequency is a direct related to relevancy. So marketers make the mistake and business make the mistake saying, our email’s not doing well, we should send out less. It’s not doing well because we’re annoying people. So they start to send less. That’s horrible math. You’re not going to send less and get more customers, more prospects, more response. It doesn’t work that way. The reason it’s not going well is you’re not sending out stuff that’s relevant. It’s really boring. Nobody cares how you’re writing. It is terrible. Okay. So if you can be relevant, then you can send out an email every single day. And here’s the interesting thing about email these days, is that people think the reason that you go to the junk or spam folder is because you wrote something in your subject line like the word free, or maybe you have too many capitalized letters or some other nonsense that there are these spam trigger words or whatnot.

That was the case 10 years ago. That was why you went to the spam folder 10 years ago in the junk folder. But now you go to the spam folder or the junk folder in business to business marketing for lack of engagement. What the receiving email infrastructures are looking for is how often is this person open or clicking on your email? And in general, the sender, how often are people opening and clicking on the emails that are being sent? And so if you don’t send out enough email, you can’t generate enough opens and clicks to actually stay in the inbox. So the of email is you need to be sending out a decent amount to stay in the inbox, but of course it can’t be garbage. It’s got to be relevant.

Grace Clark
So then would you say that for someone who’s keeping track of their KPIs and things like that for an email campaign, I mean I know it varies depending on what you’re trying to do, but would you say that engagement is one of the most important KPIs?

Jay Schwedelson
Absolutely. I mean, look, a lot of people tell you things you shouldn’t look at open rate, send you people opening up your emails, I think should, I think it’s ridiculous not to look at it. Your clickthrough is critical. If people are applying to your emails, you’re sending out sales emails, that’s all critical. The number one KPI that I don’t think enough marketers track as it relates to email is your email growth, meaning how many net new people are you adding every single day? The scary part, especially in the world of B2B and in the sector, the engineering sector is among the hardest, the average attrition rate for any email database is about 20% annually. In the engineering sector, it’s actually even higher. It goes up closer to 30%. There’s lot of turnover, a lot of changing of jobs and roles and things of that nature.

And so that attrition number is brutal. And it happens. People change jobs, they change email providers, all sorts of stuff. So if you don’t have things in place to constantly be growing your database, different ways to be doing data captures, then on annualized basis you’re going to be shrinking. So email engagement is really important. Those are really important KPIs. But for me, the number one metric that I look at in my business every single day is how many net new people got added to our database, and also how many people do we lose for whatever reason? And we got to be growing. If you’re not growing, then eventually you’re in big trouble. So I don’t think enough marketers look at their database growth. I don’t think they have enough plans in place that while they’re sleeping, that they’re growing their database. And that’s essential.

Grace Clark
That’s a really great point. So for those who hear that and they’re like, oh, I have a subscribe button, what else do I do? What are some ways that you can grow that database?

Jay Schwedelson
I think the most underutilized tactic, and a lot of business marketers are afraid to do it but they shouldn’t be is pop-up contact captures. And a lot of people say, well, I hate I go to a site and they annoy me. They’re terrible, they’re the worst. But the reality of it is when you go to a site and you see a popup and it says, Hey, give your email address and you’ll get the five things all engineers need to know in 2025, what do you do? You either put your email address in to get the piece of content or you get really annoyed and you hit the X in the upper right hand corner, and then after you hit that X, do you leave that website and you say, I hate this website. How dare they? Or do you just go onto the website and you forgot to even click the little x?

Well, 99% of people forget that they even saw the popup and they move on. But on an average basis, first time visitors for B2B websites will actually fill out that form about 7% of the time. And you don’t have to do just popups on somebody going to the page. One of the best things you could do is have timed popup contact captures depending on the topic of the page. So let’s say for example, you might have a page that’s a pricing page for your services. If someone’s on that page, let’s say 30 seconds, I don’t care what platform you use for your email and your website hosting, they all have this. Somebody’s on the pricing page for 30 seconds. You can pop up a popup specific to that page that says, you want to know more about our pricing, put your email address here. Or let’s say you have different pages for different industries, or you have a page for retail versus hospitality versus healthcare. Somebody’s on that healthcare page after 30 seconds, they’re on there, they’re reading stuff, you pop something up, do you want our guide about the healthcare, blah, blah, blah. Great. Put your email address in. These things work so well. And while you are sleeping, you are growing your database and this costs no money. So I’m a big fan of that.

Grace Clark
I like that. I like the cost: no money, working with people who have very limited marketing budgets.

Jay Schwedelson
For sure.

Grace Clark
So you’re mentioning things like relevant content and guides, things like that. Do you feel that every email that you’re sending to a potential client or your database, does it need to have that takeaway like a guide, here’s a thing for you to download or can just messaging be enough?

Jay Schwedelson
Great question. And what I would say is that I think it’s important that actually the majority of the emails that you send out have absolutely no agenda whatsoever. The biggest mistake that in the B2B world is we constantly are hitting people up saying, register for this, download this, fill out this form, do this. It’s very annoying and it’s very hard to position yourself as a thought leader. A lot of times I think attribution is garbage, right? So what do we try to do? Oh, we did this paid search ad. So they clicked on it, they became a customer, we sent out this email, they filled out this form, they became a customer. It’s because we did that thing. That’s not true. The way it works is that we create surround sound in the B2B world. We are constantly providing, hopefully providing value information and then position ourselves as a thought leader.

So when the time comes that that company needs your product or service, like, oh, you know what? That company is really good. They’re always sharing really important stuff. I’m going to go and reach out to them. And so the majority of your emails should be things that you are sending out that are completely ungated, no form to fill out. And it is content where it may be literally one sentence from your salesperson that says, Hey, there’s this new trends report thought you find this interesting. By the way, there’s no form to fill. You always want to tell the person that. So that way they know that there’s no barrier. And you do that a lot. And then over time they’re like, wow, this person’s not just trying to sell me. They’re giving me stuff. And that is how you win and that’s how you really can grow into a position of authority when the time comes for that sale to occur.

Grace Clark
Building a lot of trust, essentially.

Jay Schwedelson
Absolutely. That’s everything.

Grace Clark
That’s a really cool way to put that. I like that a lot. What do you think are two to three elements that every good email will have? Is it always like you’ve got to have your logo with this link or something like that?

Jay Schwedelson
I think it’s changing a little bit. I think before it used to be a certain way that you design stuff and a certain way of laying out your email. So it flows a certain way. But I think that the world is changing quite a bit because of ai. There’s so much generic garbage that’s being sent out. People are going to chat, GBT, write this email for me, create this blog post, blah, blah, blah. And there’s this flood of just generic. And so what stands out now? What really works now, what resonates now is this kind of humanity of it all, where you feel connected to the person that you’re hearing from and the brand has a voice as well. And maybe the format stands out a little bit differently because it’s not like what everybody else is doing. So I think the days of having a template that, oh my God, this is our template, it’s so good. It checks every box. I really think we’re starting to migrate away from that because we are just getting inundated with just the sameness everywhere. So we’re in this evolution period, I think because of AI.

Grace Clark
I mean that makes a lot of sense. And AI is moving so fast. I mean, I’m now seeing AI apps in just about everything that you use. It’s driving me nuts.

Jay Schwedelson
Yes, it’s getting crazy.

Grace Clark
Do you feel like, so bringing the human element into an email, do you think that looks like more of when you send an email, it has a human address, an actual persons address, you’re addressing it as a person, gone are the days of general addressing people?

Jay Schwedelson
Yeah, so twofold. I think that of course brands are always going to be sending out emails from their brand accounts and they should. That shouldn’t go away. But I don’t, regardless of how big your company is, I don’t care if you’re a Fortune 100 company or a tiny company or whatever it is. I think that every brand should have a newsletter that comes from someone in leadership at some capacity that is written in a voice that sounds like it’s a human being because this is going to become the dominant form of email that works really well. And the reason I say it’s going to become that I’m talking about a newsletter, it’s coming from a human within that brand is that later on this year, Apple’s going to be releasing iOS 18. And when they release iOS 18 on the phone, they have the mail app.

And over 50% of business to business professionals check their email on the mail app on their iPhone. And what Apple’s going to be doing is they’re going to, for the first time, be leveraging AI and they’re going to be bucketing emails automatically within the mail app into different buckets. There’s going to be a primary tab, a promotions tab, some other tabs, and the majority of our emails can all go into the promotions tab, the brand emails. But the personal newsletters are going to stay in that primary tab. They’re going to be deemed one-to-one. And so having a promotional email vehicle in the form of personal newsletter is going to become critical to your business in order to get your message out there and across. Because anything that goes in that promotion tab is going to have a tough time. So that’s why I’m so bullish on making sure your brand has a human voice.

Grace Clark
Yeah, it’s great to know that that’s coming down the pipeline with that. What are some other trends that you’re noticing right now and other things that you think might become more common as the year goes on?

Jay Schwedelson
Well, one of the other things, and not to get too far into the weeds on it, but the pre-header. So you have your subject line and then you have your second subject line. That little gray Texas under your subject line, that’s the pre-header. Well, in iOS 18, they’re actually getting rid of the preheader. So it’ll be really interesting to see how marketers react to that if they change whether or not they include that or don’t include that. So we’ll see what happens there. And then I think there’s going to be also a big push towards back towards letter format emails as opposed to just heavy graphical format emails. And then there’s going to be a whole new ushering in of keywords that we need to learn within email. And the reason I’m so focused on iOS 18 is that it’s going to change everything. But in iOS 18, they’re going to take emails that have certain keywords like your appointment’s coming up or this is shipped, or a series of different words like that. And they’re going to list it as a priority message. It’ll even show up on your phone and when it’s locked. So learning what those keywords are to see if you can get any of your messages to show up like that I think is going to be the new email game that we’re all going to have to learn how to play.

Grace Clark
Is there anywhere that people could go to find out those keywords or, I mean, I’m sure you guys are going to be on it.

Jay Schwedelson
We’re working on it, so not yet. So iOS 18 right now is out in beta and literally just three days ago they released the first beta version that had the mail app with what they’re calling Apple. So information is just trickling out right now. I would say by September, late September, we should all have a pretty good idea of what all the words are and all the things. And then by October this is going to roll out. So as you close out the year, your email performance is going to do really well because what’s going on? Or it’s going to do really bad because you haven’t been paying attention.

Grace Clark
Well, hopefully people go in the not bad direction, right?

Jay Schwedelson
We’ll see what happens. They’ll learn quickly.

Grace Clark
Alright. And what are some recommended tools that you think everybody should be using when they’re writing emails for clients?

Jay Schwedelson
The easiest thing to use, which I think is underutilized, is chat GPT. What I mean by chat GPT is not going on there and say, write this email. Don’t do that. If you go to chat JT and you take the email that you’ve created, the graphical people don’t realize, you can go to chat GPT and you can now upload an image very easily. So when you go to chat GPT, the free version, the regular version, right next to the prompt bar, there’s a little paperclip icon. You click on that and you could upload an image, you take a screenshot of whatever your email is and you upload it. And then you ask chat GPT, Hey, I want you to act like the greatest email marketing consultant in the world. I want you to analyze this email. And the goal of this email is to get webinar registrants, tell me, analyze everything and don’t be nice about it. What do you think? My call to action, the copy, the paragraph length, the images, everything, and give me a full rundown of what you think I should change and why. And it will give you back as if you just hired the greatest email consultant in the world, a complete shredding of your email. And it works incredibly well. And I don’t think marketers or business owners or anybody leverage the fact you could upload images to chat GPT like that and it works great.

Grace Clark
That’s a really cool idea. Would you say the AI robot is pretty mean to you?

Jay Schwedelson
It is mean to me. I ask it. It’ll say something. I’m like, I want you to be harsher. I want you to be more direct. And I also think that’s the problem with AI that people don’t understand. It’s not a search engine. People ask it very basic stuff. It gets back very basic answers. But the more you push it, the more you ask it, the more detailed you are. You could say, okay, my call to action button, can you tell me 25 different ways to rewrite that to create more urgency? It’ll give you that. You just need to be that specific.

Grace Clark
Would you say it’s pretty accurate in its assessment?

Jay Schwedelson
I’ll tell you why I think it is. So we did this wild thing where in my agency we do for our clients, we’ll do, we don’t just do email, we do lots of different media, but we do a lot of email campaigns, promoting webinars and content downloads and all this stuff. So we took 200 campaigns where we had an A and a B version of email creative that we had sent out for these 200 different campaigns. And for each of these campaigns, we had already run the campaigns. We knew which of the A and B version had done better, but we wanted to see how good was ChatGPT at predicting email and what was going to work. So we uploaded 200 times the A and B version where we already knew the outcome for all the campaigns. We said, which one is going to do better? Predict it based on this desired outcome. And it got it right 88% of the time. And it kind of blew our minds like, wow, you could upload two different versions of creative that you’re working on and say which one’s going to do better, and this is a pretty good chance ChatGPT is going to predict the outcome without you even hitting send. So that kind of changed my view on how good or bad Chat is.

Grace Clark
Wow, that’s intense to say the least.

Jay Schwedelson
It was. It was a lot. It was pretty cool.

Grace Clark
What do you think that means? Just curious, what do you think that means for people like us who are in marketing, who are helping people with their marketing and ChatGPT can do things like that. What will be our future role in consulting?

Jay Schwedelson
I actually think we’re going to have a bigger role than ever because the people that I think are making the mistake are going to ChatGPT and say, write this for me, create this for me. It’s one thing to take what you’ve created and say, ‘Hey, ChatGPT, what do you think of this? What am I missing? Help me think out of the box a little bit.’ That’s a win. The consultants, the agencies, all the people that are helping out that are going there to do the work for them, yeah, they’re going to be in trouble. It’s not going to go well for them, but if you have it kind of be your partner as opposed to just being the solution, I think that it’s great. I’m a big fan.

Grace Clark
That’s a great perspective. Outside of ChatGPT, are there any other tools or maybe recommended readings that you have for people to check out who want to learn more?

Jay Schwedelson
Yes, I would say don’t sleep on some of the other very simple free tools that are out there. I’ll give you an example. So Gemini from Google, just like ChatGPT. Google has Gemini, it’s gemini.google.com. It’s free, it’s as easy to use as Google is. Don’t be afraid of it. But the things that you could do in Gemini are different than ChatGPT. So for example, you can go on Gemini and let’s say you don’t have time to watch a webinar or to listen to a whole podcast or whatever, you could go on, take the YouTube link, it works for the YouTube links and go on Gemini and say, ‘here’s a webinar. Can you please summarize this for me? Can you please tell me every stat that was mentioned? Can you turn this YouTube link into a blog post?’ It can do that instantly with any YouTube link.

And I love that. And then the other thing that Gemini does, which I think is super cool unlike ChatGPT is it can analyze websites. So let’s say we were just doing this for a client. They were an accounting software client and they wanted to come up with their go-to-market strategy. So we went on Gemini and said, ‘Okay, please analyze these three accounting software sites, FreshBooks.com, QuickBooks.com, netsuite.com, and create a graphical table for us instantly with check marks for if somebody’s good or bad at this on the website for pricing, what industries they’re in, competitive differences, and make me a table that breaks down each site compared to the other one.’ And instantly it will do that, right? So being able to use Gemini to analyze websites I think can be a game changer that I don’t think enough people are paying attention to.

Grace Clark
That’s really cool.

Jay Schwedelson
Yeah, that is cool.

Grace Clark
That’s awesome. Well, I think that’s most of the questions I had. Christine, did you have any that you wanted to ask?

Christine McQuilkin
No, it was a great conversation, but just like you talk about things other than work, Grace was going to dive into some of those areas.

Grace Clark
I wanted to ask, I’m not totally caught up on it, but have you been watching the latest season of The Bachelorette?

Jay Schwedelson
Of course I have. What’s wrong with you?

Grace Clark
And your thoughts so far? I mean, how do you see it going?

Jay Schwedelson
I like Jen a lot. I think she’s a great bachelorette. I’m a big nerd and I’m a little upset because I love the Olympics, don’t get me wrong. But because of the Olympics, the viewing numbers are down the last two weeks really badly on the Bachelorette. So there’s a lot of information out there that the season’s not going well, but that’s just not fair and that’s just not true. So I feel bad for Jen because she’s not getting all the attention that she deserves, and some of the guys are just total clowns as usual. My biggest thing that I’m upset about is that I’m very excited for the Golden Bachelorette, which is coming out in September for the first time. That’s not the Golden Bachelor, it’s the Golden Bachelorette, but they’re not having a Bachelor in Paradise season until 2025. So I’m very sad about that because Bachelor in Paradise, which is the show of all the rejects on the Bachelor and Bachelorette is my favorite in the Bachelor universe. So we have to wait another year for that, which stinks.

Grace Clark
Oh, that’s a bummer. Just curious, why is it your favorite out of all of ’em?

Jay Schwedelson
Well, first of all, it has the highest rate of success. You have all these people that are so desperate to get married and so they all are there and there’s an equal number of men and women, whereas a Bachelorette or bachelor, only one person can get paired off. But on Bachelor in Paradise, it could be like 5, 6, 7, which is fantastic. The marriages don’t work out and they’re all a disaster, but at least you feel good for five minutes. Do you guys watch these shows or am I alone?

Grace Clark
I don’t watch them as much, but I do enjoy really junky shows like Marriage Bootcamp. And a few times there’s been some Bachelorettes and Bachelors on there. They’re pretty hilarious trying to pull together.

Jay Schwedelson
That’s not junk, that’s quality entertainment. Good for you.

Grace Clark
A quality entertainment of watching people who should not be together.

Jay Schwedelson
Absolutely. That’s the best part. Like Married at First Sight. That is just unbelievable what goes on. Yeah, it’s all good.

Grace Clark
Good quality stuff. I know Christine doesn’t watch any of those.

Jay Schwedelson
Well, she’s an intellectual. I understand that.

Grace Clark
She’s an engineer by trade.

Jay Schwedelson
She thinks Bridgerton is intellectual. That’s what’s going on there.

Christine McQuilkin
I’m working my way through The Mindy Project. I’m like decades behind everyone else.

Jay Schwedelson
I like that. The Mindy Project is great. And then she also wrote that other show. Oh no, Never Have I Ever, which she wrote, which is so good. Mindy Kaling, she has to check it out.

Grace Clark
It’s very good. You have to check that out. Love her. Those are all the questions that we had for our podcast today. Was there anything that you wanted to add, maybe like a parting word to our audience?

Jay Schwedelson
No. Well first of all, thanks for having me. This is super fun and engineers are people too, so let’s treat them like people and market to them like people. And this is awesome. And I appreciate you guys and gals.

Grace Clark
We really appreciate you joining us today.