How to Upgrade Your Webinar and Email Strategy for 2026 with Jay Schwedelson (Founder, SubjectLine.com)

Hey, it's me, Dave.

0:00

This episode is brought to you by.

0:01

Our friends at Knack. Knack is a no code email and landing page creation platform focused on a problem every marketing team runs into. Have you ever had a really good marketing idea but then it takes forever to actually ship it out the door? It's usually not because your idea is bad, but because the process in the middle is slow. Briefs, more briefs, approvals, reviews, tiny fixes that somehow turn into weeks. And by the time the campaign is finally ready to go out, it barely even looks like what you originally wanted to ship. Yep, that right there, that is the gap that Knack exists to close. Knack is a no code email platform built for modern marketing teams. They have AI built into the platform that lets you prompt ideas and instantly generate on brand email assets so you can create, review QA and launch your email all in the same place. No jumping between tools or messy handoffs halfway through after the email goes live. Knack also gives you performance insights and recommendations so you can see what worked and how you can make the next send better. So if execution is the thing slowing your marketing down or you just want one system that takes you from idea to shipt to learning to improving, you should check out knack. Go to knack.com exit5 that's k n a k.com exit5. You're listening to the Dave Gerhardt Show.

0:02

Hey, it's Dave. This episode. My guest is Jay Tweddleson. He's the founder of Subject Line.com and Guru Media Hub.

1:39

He's the host of do this not that podcast.

1:45

We talked about podcasting, virtual events, webinars, live events, email, subject line tips I took legitimately. I don't know why I do this.

1:48

I could get the transcript later, but.

1:58

I took about three pages of notes.

1:59

During this conversation with Jay.

2:00

It's awesome because a lot of us.

2:02

Are doing content and content marketing and.

2:04

So much of the success of content comes down to packaging and the actual offer and the stuff we're creating.

2:06

We talk so much about that.

2:11

Plus, Jay is just filled with little nuggets and sound bites about the best time to send email, why it's actually okay to run webinars on Fridays, and why some of the best performing emails they've sent have come on Sundays. The impact of removing the preview texts from sending the email on open rates. There's so much good stuff in here on podcasting webinars events. Enjoy my conversation with Jay Schedelson.

2:12

It is a great one.

2:36

All right. Excited to do this episode, Jay Schwedelson. We got connected through email content over the years. Love your energy. Expert in all things email events and virtual events. We were just talking backstage, but let's kick off this. You actually, you created this virtual events business. We were just talking about how to explain to your lawyer friend like what a virtual event is.

2:37

Right.

2:58

Can you kind of like recap the events of maybe the last 30 days and that's a good way to introduce you and tell the story about your business.

2:58

Yeah, for sure. So I have a media business called Guru Media Hub. And some of the things that we do is we put on really large scale, completely bonkers, very different virtual events, ones that you actually might want to go to, we do them at scale. So we have one that's about events called Eventastic, that's about 15,000 people. But our biggest one is called Guru Conference and it's about 30,000 people. It's all about email marketing. It's a virtual event. We just had it. We had Nicole Kidman there. Whatever. So about whatever. Yeah, right. That's my flex. You like that?

3:05

Hold on, hold on. For the marketers listening, not to derail your story, but like how do you get Nicole Kidman for a virtual event? Does it seem like a regular event? She's got an agency. And you reach out.

3:35

You do. And I will tell you the thing, the reason I like doing virtual events is that with celebs, first of all, they're a lot less expensive because again, the fly somewhere and show up. It's like you know, 5, 10x what they have to do virtually so you can get people that we otherwise way out of reach virtually. And the thing I always get asked about is talking about an email marketing conference and people say, well, what the hell does Nicole Kidman know about email marketing? And I was like, absolutely nothing. Who cares? I go, this is a human to human thing. You want to show up and see what she has to say. And I think that's part of why people get virtual events wrong. They think you have to like follow this boring ass playbook that nobody cares about. So what ended up happening was after the event was a big success this year, it was bonkers. Ended up having a conversation with the leadership at Constant contact, the big billion dollar 500,000 customer global brand. And they're all growing up.

3:45

You know, that's where I cut my teeth at young Dave Gerhardt with hair.

4:35

That was where you became the legend that is Dave Gerhardt.

4:39

No, that's still a work in progress.

4:42

In my Own mind, the legend in your own mind. And so fast forward, they were like, we love what you're doing, and we want to lean in and make this even bigger. So they acquired Guru Conference along with some of my other media assets like subjectline.com and they just want to take, you know, email marketing to all around the globe. So it's really validating to see, you know, a big brand like that see value in something like a virtual event. And so, yeah, we try to look at the world a little differently.

4:44

Okay, so how have you created this virtual event that is worth a company spending lots of money to buy and forget that. Forget even the acquisition.

5:12

Right.

5:20

Even if this didn't happen, you were still going to come here. You've created these virtual events. You get thousands of people to go. You have really interesting plays, how you integrate brands in them. I thought people don't go to webinars, Jay. I thought webinars are dead. Isn't virtual event just another name for webinar? How have you made this thing interesting? And let's talk about it with the lens of, like, I believe in this channel, and I want to help people realize, like, it's not that the webinar is broken, it's about the packaging. And I think you guys do an awesome job at this.

5:20

Well, I appreciate you saying that. Let's just talk about webinars for a second. Besides, from my events, I think webinars are critical content play for B2B marketers, but they are stained and they're done completely wrong. I'll give you an example. What I mean, anybody that's out there right now that's using webinars as a go to Marketplace. If you are actually calling it a webinar, you should stop listening to this podcast and go and change that. What do I mean? We've done all this analysis where we take the exact same webinar, content, pictures, marketing plan, everything, and all we do is we do an AB test on calling it the webinar or something else. So when we, for example, call webinar a live panel, a live insider session, right? And live insider session will outperform the word webinar by about 35% in terms of registration. And all you've done is not use the worst word in the human language, which is the word webinar. The biggest mistake in marketing, you have a webinar that you're promoting, you send out an email. The first word you put in your subject line says webinar. Colon, boring, boring, boring, boring. Nobody cares. Okay? So you just need to think about everything, whether it's your virtual event. I'm happy to take you through some of the things that we do. But if you're thinking about your webinar, stop following everybody else's playbook and just look at it a little bit differently. And that's how you can win.

5:47

Yeah, I love that we call ours live sessions. I don't know, it just, it's not even, I'm not even trying to be cool with it. Just live Sessions. And it's actually become a joke that when we host them in the chat, like, I get mad if anybody calls it a webinar. And I joke like, this is absolutely not a webinar. Like wink, you know, and it works. That's amazing. Live insider session versus webinar, even just testing that. But that, that all goes back to like the packaging. It's like the reason no one's showing up is because we're not putting enough thought on the way in. Let's actually create a product here. And I also think there's something, there's a psychological trigger or some marketing hack where like, if you can name it, it just feels more real than like webinar. Tomorrow on the 10 best practices for blah.

7:06

A hundred percent. And I would say there's another trick. I hate calling it tricks, but welcome to marketing and it's on the way out. But you package in your marketing and what we've learned is that the world now needs to have attend to receive. What do I mean by that? We know that if people show up to a webinar as opposed to watching it on demand, number one, nobody actually watches on demand. Let's start there. But if they actually show up to a webinar, the percentage that they go to pipeline is about 400% higher than if they watch on demand. So how do we get them to show up? Because show up rates are down year over year significantly. So if you don't have baked into your marketing a tend to receive again, you might want to stop listening. Go do that. What does that sound like? What does that mean? So you want to say if you attend live, you get the Q2 summary guide for HR professionals. If you attend live, you get beta access to our new SAS release. If you attend live, you get live Q and A that nobody else will get. And then you put that front and center in your marketing. You need to have a tend to receive elements to your webinars to increase the shop rate, because that's when your bdrs get happy on following up on the lead. So again, it's not that webinars don't work anymore. It's that everybody's doing what they've always done.

7:44

So a tend to receive. Do you have like data around that you've seen that that improves people going. Because I feel like I would just go for like two minutes and then I'd be like, all right, I'm on the hit and I'm out.

8:55

Yeah. So you have to stay. You know, usually we time it. We have to say at least 50% of the time for it to trigger. And what we have found is actually increased show up rates by over 30%. And when it works. And when it doesn't work, it doesn't work. When it's just like in the background.

9:04

Yeah.

9:17

Like of your marketing. It has to be one of the lead elements of your marketing. Hey, this great new live insider session. And if you show up live, you get the Q2 report for blah blah blah. You need to lead with it. That's when you get the benefit.

9:17

So like I agree and then. But also my brain is like, but isn't there also a play where like people are busy? There are so many other things. Like it is a sign of interest if I'm interested in this topic. But I'm not going to show up live because I got other stuff on. Maybe I am going to listen to it later. I know that that's kind of like people who, you know, everyone works out every day or whatever. It's just you say it but you don't actually do it.

9:30

I don't buy.

9:52

I feel like if that content is good though, wouldn't I want to spread that to more people? Like I want to send you the recording.

9:53

So here's the thing. The answer is yes, we should be wonderful to all people. I don't subscribe to that at all. The problem is we've turned our marketing into Netflix. It's there whenever you want it. It's always available. You know what, that's how you wind up scrolling and never watching anything on netf. Know what the hell to do with yourself. So for example, at my virtual events, our big giant virtual events, we have 30,000 people. Whatever we don't do on demand. That's crazy for a two day event. We do not do on demand. So if you don't show up, you're screwed. You don't see any of it. But what we do is what we created something called earned on demand. If you show up for one hour to our virtual events, it will Trigger the on demand link. But if you don't show up for at least that one hour, you. You don't get it at all. And people wind up staying five, six, seven hours, whatever it is. And you know what? It's not touchy feely. I get a lot of hate email. I hate you. I really wanted to go. I can't believe you're not making this available. You're a terrible person. People tell me to die, which is terrible. Them about virtual email marketing content, who cares? But the moral of the story that I found is we need human to human connection, whether it's on a webinar, a live event, in person, a virtual event. And if you want to be all things to all people, you want to cater to everybody, good luck to you. Have fun going out of business. I want to get people there and get their energy.

10:00

That's interesting because there is something I'm just thinking about, selfishly about our webinars. The people who go, it's amazing. They stay the entire time. The chat is insane. People aren't just like dunking on the speakers. They're like trying to help each other out in chat and they're sharing stuff. So like, maybe it's like you're trading off. I might have to let go of like, oh, but all these people aren't going to see my content. Would I rather be able to say like 10,000 impressions or 250 super engaged people? Live. That's kind of the bet you're making, right?

11:15

Yeah. And you know, it's okay, let there be fomo. Okay. It's, you know, I think live events. I'm a big believer in live in person events. I believe that live in person events are going to be the things that outlast AI. Like, if I was going into my marketing career today, I would go into live in person events because it will win the day. People are going to be starving for human connection as this AI stuff unfolds. And so I think we need to treat anything virtually, whether it's a webinar, a virtual event, whatever, as if it's a live event. Because if you miss going to that live event, then you missed it. Yeah, you can watch the on demand that nobody's going to do. But the more we treat live things, the more we take our online stuff and we try to bring that live component to it. I think that that's how we're going to win.

11:46

I like that. I like that bet. I'm into that. I'm betting like I'm using AI. But I'm. I'm really into people right now.

12:29

Right now?

12:38

Yeah, right now. I think it's made me appreciate it. There's just a certain type of energy. I mean, I sit in my office and I spend half of my day. I don't know if you're real. Like, you know, it's a video. I spend all of my time on a video conference. But then last weekend we had, you know, 10 of our neighbors over for brunch and it was just hanging out, bullshitting with people. I think there's just a certain energy that I agree that we do miss.

12:38

Well, you guys have created an event also where you bring this energy live with drive.

13:00

Oh yeah.

13:05

You bring everyone to where you are. And I guarantee you coming out of that, there's just so much more than just if you're, you know, watching on demand garbage.

13:05

I was telling you about Dan, our CEO behind the, in the backstage stuff, we always joke, we call it being drunk on events because inevitably one of us is somewhere the other isn't. And it's like Thursday night at 11 o'. Clock, I'm never up that late. I'm calling him, he's like, what? I'm like, dude, I just left this event. I left our New York City meetup. And I'm like, I got 100 ideas. And then like the next week he's like, oh, you're just drunk on events right now. The next week he calls me, he's like, I just went to our Arizona meetup. And you won't believe it. It's like there is something different, 100%.

13:13

Listen, I think that especially in this world where a lot of companies are still not in office. Right. Like remote work is still a big thing.

13:42

Yeah.

13:49

The only place we're really getting together are these industry events or pop up events or dinners or whatever. I think more and more they're going to become that much more valuable. I do think that any business doesn't matter what you sell, what you do, how boring your industry is, whatever. If you don't have an in person motion for your business in some capacity in terms of some sort of micro event or whatever, or at least a big presence at industry events, I think that you're going to be left behind.

13:49

I want to talk more about in person events.

14:15

People love these little plays.

14:16

Like you got the subject line, you know, calling it an insider session versus a webinar.

14:18

They attend to receive.

14:22

Give me some more webinar, not webinar plays. You've learned over the years.

14:23

Yeah, right. So insider session plays webinar plays a few things. Number one, we're seeing attendance rates and registration rates on Fridays. Crush it. In the last 12 months for so long in B2B world, it was like, no, no, no, we don't do anything on Fridays because that's a really bad day. It couldn't be further from the truth. And if you haven't tested it, you should because sort of coming out of the pandemic, we found that Fridays are the day. Like you'd better yourself. You take less calls, somehow you consume more content. We see these show up rates and registration rates for Fridays has gone up exponentially. And the other big thing is the other big real estate that nobody's really using in B2B is weekends. Sundays big time. Sending out long form emails on Sundays around 11 o' clock or so is incredible because I don't have a work life balance. And if you do, God bless America, God bless you. If you could turn it off at 5pm on a Friday and not think about work until Monday at 9am, you are a unicorn. Okay. On Sundays is the only time I can really look at my email. Not everybody slacking me or this other garbage. And I can consume stuff. And what we have seen, this was a media post as well that click through rates for business to business emails on Sundays is up like 60% year over year. So if you're not promoting that webinar on Sundays, you're not taking advantage of Fridays. I think there's a lot of real estate out there that you should be reconsidering.

14:27

Amazing. Amazing. We need all this. I need all this in our business now. We just had this conversation yesterday. We need to do another promo for an event that we have coming up. And I was like, we should send the email on Sunday.

15:45

Yes.

15:55

Because we're targeting execs and a lot of execs are Sundays. You know, is the cleanup. You get ready for the weekday and then interesting your anecdote on Friday. I think there's something we got to do. We have this group of CMOs and we do their events on Fridays and they all say, actually we didn't choose Friday. We gave them a list of the dates and they almost all always said Friday. And the show rates on Fridays have been awesome. And so I think there is something there. I love the way you frame that. The we all spend the week. You kind of have less meetings on Fridays. Maybe Fridays you're maybe leaving a little early to go pick up the kids or do something 100% you take a call that day. I like that. That's really good. This might be too much. We're giving away too much. I'm not going to publish this. Sorry.

15:56

Okay.

16:35

This is for me.

16:36

This is for our business.

16:36

Yeah. What about the content? Like, for me, I love all these plays, all these things matter. But, like, to your point about Nicole Kidman, is that who it was? Right?

16:38

Yeah. Yeah.

16:47

It doesn't matter if she was on Friday or Tuesday. Someone's gonna go because she's there.

16:48

Right?

16:52

Talk about the overall, just like packaging. So we had this name Live Insider sessions. How can people get better on figuring out, like, what should we do a virtual event about, though?

16:54

So that's an excellent question. I always think there's two paths that everyone needs to think about. Because the biggest mistake in B2B marketing is that everything is a lead. If someone downloads a guide, oh, they go into our KPIs for our lead. We got another lead. If someone registers for webinar, they're a lead. If someone downloads a case study, they're a lead. And somehow we say all these leads are created equal, which is absolutely ridiculous because if someone downloads the 101 guide for HR, whatever, they're garbage compared to someone who downloaded a case study who's obviously in market for whatever the hell it is that you're promoting. And the reason I say that is I don't think that numbers should be what we are measured against. So, for example, if you're doing a webinar, what is your goal? Is your goal database growth? General awareness? Okay, great. Do basic stuff that's like, you know, what everybody needs to know about the 2026, whatever, very top funnel stuff. But if you're trying to sell product, okay, you want to get people that are mid funnel, not top of funnel. The intentionality of the title of your webinar is very important. How to fix this problem with your productivity in three simple steps. Because that's actually what your product does. And you're going to get less people to register, but the people that do register are going to be more of a mid funnel play. So I think you have to really be, not just, what should we call it, think about what the outcome is that you want. And the other packaging thing, which is really more of a trick, hack, gimmick, whatever, is how long your webinars are.

17:04

Hey, it's Dave. Today's episode is also brought to you by Optimizely. Okay, Everyone is using AI right now. Point blank. That part's done. We're all Using all the tools for copy ideas, baseline stuff, but there's still a gap. Most marketing teams are using the AI tools to think and not actually do. That's where things are headed next. And our sponsor Optimizely built this platform called Opal that lets you use autonomous AI agents to go and do the stuff you shouldn't be doing manually versus just being another chatbot. Here are some examples. Opal can create and optimize on brand webpages, emails, SEO content and campaigns by audience segment. It catches brand, legal and accessibility issues before anything else goes live on your website. It pulls data from your other systems like Google Analytics, your CRM and sales tools to auto build reports, summaries and recommendations and more.

18:30

And guess what?

19:21

It's completely no code. So marketers like you and me can build and leverage agents for any use case we dream up without having to rely on developers.

19:22

That is freedom. So get this.

19:31

Optimizely has this incredible offer for Exit 5 listeners. They're offering a free personalized 45 minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time with a practical plan that you can actually go and use right away. They're giving everyone who attends live a free pair of meta ray bans, which are awesome if you haven't used them yet.

19:33

So you should go grab a seat.

19:55

Right now at Optimizely.com/exit5. It's Optimizely.com/exit5. Check out the workshop Get Smarter About AI. The future is here.

19:56

If you're doing a 60 minute webinar insider session, you are out of touch. Nobody wants to put that on their schedule. Period. End of story. I don't even want to do 45 minutes. We are huge fans right now of 22 minutes. I'm going to tell you why that is the secret sauce number 22 minutes. Because what happens when you promote is 22 minutes. I'm like, I could do 22 minutes. They put a 30 minute block on their calendar, okay? And you give them, I hate that line. But you give them back eight minutes. And people say, well, I can't do it in 22 minutes. I'm like, well then you're boring and you stink. I had Yamini, the CEO of HubSpot came on my podcast. I did. That episode is an 18 minute episode because I knew I could have talked to her for three days. Okay, it was Yamini, but I knew if I kept it that short, it would get consumed that much more when you promote your webinars, 22 minutes, for some reason, first off, anything that's not a round number, a five or a zero, like 30 minutes, an hour, whatever.

20:08

Not believable, crushes it.

21:03

People believe it more.

21:04

Yeah.

21:06

So testing different time elements is another way that I would really lean in.

21:06

Do you think I should do that for the podcast then, too? Like, every podcast is just a default book an hour. But, like, if I just cut this right now, that was an amazing 15 minutes just on webinar stats. But then I'm like, but there's so much other stuff that I still want to talk to you about.

21:11

Yeah. Well, so I have a podcast. I've had a podcast for a while, and I have found the shorter I go, the more downloads I get. I think if I get to zero minutes, I'll take on Mel Robbins. But really more to it, though, is it's not even about, is the content good? People make the mistake with podcasts that I'm going to have the greatest episodes. This content is so good. Who cares how good your content is? That's not what people are doing. They're looking at the title of the episode and then they're saying, how long is 22 minutes? Okay, fine. Then they. Other times they're looking hour and 10 minutes. What is this garbage? Who has an hour, 10 minutes for anything? And they say, screw that. Now there's plenty of people out there that say, no, no, no, no. I listen to this time and I'm driving. I do it again and again, again. And great. You have 12 super fans. Good for you.

21:26

Yeah.

22:09

The reality of it is, if you chop it up, here's the way that the algorithm works on Apple and Spotify and all the things, they're looking at your downloads. Okay. And so if you chop up this episode into four things and people are loving it, and now they Download the next 10 minutes, the next 20 minutes, the next, whatever, you're getting more downloads. And then the algorithm within Apple Land and Spotify Land circulates your show more. So not only do you get more listeners because they're not turned off by how long it is, you're actually getting more listeners because the algorithms are seeing you're getting more downloads. Basically, you're gaming the system, and that is actually how you get greater circulation.

22:09

But in the Yamini example.

22:46

Yeah.

22:48

Did you just pick one topic? And I'm going to interview it just on this thing and that's it.

22:49

That's exactly right. Yeah. With her. I just did that with her. Is that that's it. We're going to talk about this. In and out. Yeah, done. And let people want more. It's okay.

22:53

But like, what if. Why not. If she said yes to the pod, you probably could have got it for an hour. Why not have recorded four 20 minute segments and then like you can put them out over time.

23:02

I should have done that. Okay, that was a fail.

23:13

Okay. I'm just wondering.

23:16

No.

23:16

Cause I'm trying to understand, like, this is actually a great takeaway, which is like, I'm totally with you. If I saw a podcast episode on, you know, that was 17 minutes long, specifically on webinar tips, I'm like, oh cool. Yeah, sometimes. And I even do this on my own podcast is like, I talked to the guy about where he went to college for freaking 30 minutes. And I'm like, why did I do that?

23:17

No. And we chop ours up. And then it's also good for social too, because then you can almost put the whole thing on social as one clip. You know what I mean? Because it's a topic.

23:38

Yeah, but I just. There's a psychological thing there which you totally. And then the webinar thing is also super smart in our. That's a big ask, you know, you to come on this podcast means you are. If I could talk to Dave, I know he's like, okay, legit, whatever. It'll be worth it. An hour is a big block on my calendar. If I got an hour, I start to freak out. But 22 minutes now you block 30. You can make a coffee in between your next meeting.

23:47

I think it plays everywhere. So like, let's say everybody has an email newsletter that's out there. One of the best things you could do in an email newsletter is you put it in the pre header or you put it at the end of every content block in your newsletter. You add two min read the number two M I n read or three min read. Right. You put that at the end of your content blocks. You put that in the pre header of your email. You know, 5min read whatever it is. We need to have extreme management of expectations related to time. All we're thinking about when we're deciding whether to consume a piece of content, whatever it is, is do I want to make time for this? And it's in the subconscious. When you add things like three men read to that content block and Google does this all the time in your newsletter, they'll decide, you know what, I'm going to click on this. I got 180 seconds to read about whatever and your click through rates go up exponentially. Thinking about what the person's experience is and how to consider their time can be a game changer.

24:09

So do you have any opinions on newsletter length?

25:06

I have opinions on things being visually boring. My newsletter is very long. But what I mean by visually boring is one of the biggest fails, I think, in all of email newsletters is when you open up a newsletter and you see big content blocks. So for example, if I got a text right now from my mom and it was this giant text block, whatever, I would know that that was drama that I have no desire to think about right now. And I'd push my phone off to the side because I have no time for that. But when I get an email and I open up and there's a big content block, anything over five lines in one given block of text, we don't realize it, but subconsciously we immediately tune it out and we like don't keep on reading for the most part. And this is why click through rates go down. So if you could chop up your content blocks into like three or four lines, you will see your click through rates go up and there's going to be plenty of people out there like, no, no, no, you don't understand. I love morning brew, I love daily skim and there's such big content blocks and blah, blah. Amazing. It's like saying that you love the Mel Robbins podcast and it's an hour and a half long. There are going to be outliers because the content is superior. It has built up this brand, this following. But your thing, you are a B2B boring electrical engineering supply company and I promise you, no one cares about the latest innovation and whatever it is that's going on. Enough to see a content block that has seven lines and it looks visually boring.

25:09

Yeah. I haven't looked at your newsletter in a while. Part of me, I'm on your list and I open everything.

26:30

I wouldn't read it either.

26:35

Yeah.

26:36

So your length is okay, but you break it up with design. Are you like making graphics?

26:37

Yeah. So mine's long. I have all this stuff, but what I do, I have a hack that has worked incredibly well for my newsletter, which. So at the bottom of every newsletter, I send out my newsletters about marketing tips. You know, what's going on, new ideas, whatever. The bottom of every newsletter I have a section called since you didn't ask. Every newsletter ever put out and is the dumbest crap in the world of anything that's going on that I'm so I'll give you an example. This past week's edition, I talked about two topics. One, I talked about the fact that High School Musical is a 20th year anniversary and it was released on TikTok in full, but they chopped it up into 60 second clips, the entire movie. And I talked about my fascination with High School Musical and Zac Efron, which is very weird. Not that I'm into him, but who cares? And the other thing I talked about was that in my office somebody microwaved a piece of fish and the entire office stunk like crap.

26:43

Yeah.

27:33

And I thought that I smelled for about a week. And I had a breakdown over this. And so at the bottom of every newsletter I send out, I have this section, since you didn't ask, where I talk about whatever nonsense is in my brain. And the reason I do it is it makes everybody stay to the end. You have to give a reason for people to want to stay other than you saying, and by the way, sign up for my webinar. And here's my latest podcast episode. Who cares except for your mom.

27:33

And it's such a great way to sprinkle personality into, like, you don't have to make the marketing stuff have a ton of personality because it doesn't have to be corny. But then people feel like, I get to know the guy who's writing this.

27:57

Exactly.

28:09

And like, that's such a good, like, anti AI slop technique also.

28:10

Right, Right.

28:14

You know, like, AI is not going to be writing about, you know, that Mary heated up the salmon and the.

28:14

That's exactly right.

28:19

How did you learn all this stuff? How does your brain work? Like your high School musical? Like, are you the guy that, like, if you and me went for a walk, you're pointing out, like, you see that thing right there? That was actually created in 1926 by this guy, you know? Do you know? Are you a history guy?

28:22

Like, no, I don't know nothing. So first off, as it relates to pop culture, I have the worst taste in tv. I don't know why, but from day one, I've. While I love reality tv, I've seen every episode of every season of the Bachelor, Bachelorette, Golden Bachelor, Bachelor in Paradise. I've seen every season of Love is Blind. I mean, you name it, I've watched, I mean, Real Housewives every geography. I don't know why, but I love this garbage. And so that fascinates me. And as it relates to all the tips, tricks and nonsense, you know, this agency I've had forever, we just run so many campaigns. And I just always feel that there's got to be something that you can do that will get you to stand out. I'll give you one that we've been doing a lot lately that crushes it that everyone sleeps on. When you talk about email marketing, what we don't think about is white space. So for example, when you look at your inbox, if you see an email and it has no pre header, okay, if you have a short subject line, less than three words subject line, and you have no pre header, there is extreme white space around your email. And just by having no pre header and three word subject line, your open rates skyrocket. And all you did was create white space for your email to send out. Because 98% of all emails have a pre header. Now for some people out there, they're like, whoa, how do you do that? You go on ChatGPT, you say, I use mailchimp, I use HubSpot, I use Salesforce, marketing, cloud, whatever you use. How do I send out an email in my system and not have a pre header show up? Because if you just don't write one, it grabs the first line of text and shoves it in there.

28:35

Yeah, I was going to ask you.

30:05

Because that's not the preview text field.

30:06

It is the preview text field. Right. And so, well, there's two fields.

30:09

But you're saying if you leave that blank the default, you need to change it so the default doesn't show like.

30:12

The first line of the email.

30:17

Exactly. So if you go into ChatGPT, you say, this platform I use, I want to have no pre header show. What do I do? It'll actually give you some different image references to put in your emails in certain spots. It's not hard to do. And then when you send it out, you will be in shock how much higher of an open rate you get just because you have white space around your email and all the other emails don't. So it always fascinates me whenever I'm looking at any marketing. How can I go in the opposite direction? Whatever anybody is doing. Like if you have a webinar and your promo has two circles of people's heads in it and you're sending that out. Don't do that. Stop it. Stop it.

30:18

What if it's a cool graphic though?

30:55

We do that.

30:57

Nobody. Let me tell you something, I can't stand it. I get these email templates with these. These two people are speaking on our webinar. Nobody knows who they are.

30:58

Right?

31:05

Literally nobody cares.

31:06

Except do that if It's Nicole Kidman. I actually, I used to obsess over like podcast titles. I had a podcast like 10 years ago, early podcasting. And you could actually like manipulate titles. And since then I've always gone back to like, do you put the guest's name in the podcast title? Well, if it's a guest that nobody knows. And I've taught a class on this and it was like the example that I use was like, if I had Tom Brady on my podcast, I should call that episode, episode 256, Tom Brady.

31:07

That's what I did. So I had Gary Vee on. Okay. I wrote Gary V. Is here. You know who that is? I mean, but other than that, right?

31:32

It's normal to want to be like the state of social media, what works on LinkedIn and content strategy comma with Gary Vaynerchuk. But then we buried the.

31:40

You buried the lead.

31:49

Yeah.

31:50

Whereas if I say you have the senior vice president of marketing for whatever SaaS platform, who knows who that is? I mean, so do you.

31:50

Only then are you only sending three. Like, is therefore my subject line always going to be bad if it's more than three words?

31:57

No, no. I mean, and it's all about testing. Everything I said. If I said seven things to try and to them work, you're like, oh, Jay's a doofus. Yeah. Which is true on many levels, but it's all about testing. It's not everybody. This is great.

32:04

I'm taking so many notes. Like, the lesson is like, you don't need to take this as it's not like a coin operated machine where everything works for everyone. But I think you've given a ton of examples that it's like. It's like this type of thinking might be how you move the needle on some of this. Like, let's try a three word subject line with no preview.

32:14

Right, exactly right. And the reason that it works with three words, I mean, you go forwards, five words, whatever. It's just if you make your subject line too long, you don't get the benefit of the white space. That's really it.

32:31

What else should I ask you about?

32:41

Definitely not anything that you should be watching on tv. That is.

32:45

Look, I have no shame. The only. I've never been a bachelor guy, but the only. My wife and I, every single night after we put the kids to bed, we usually have one hour before we go to bed and we just exclusively watch Bravo.

32:48

Oh, amazing. I mean, I had Andy Cohen do one of my events, so that's a.

32:59

Great virtual or live.

33:04

Yeah, no, he did. So I have an event called Eventastic which is an event about events. Yeah. And I had him keynote it last year as a fireside chat because first of all, selfishly, I just wanted to ask him random weird questions, which I did. But he actually puts on event called Bravocon.

33:05

Yeah, it's insane.

33:20

Which is, you know, a 30,000 person event. So I was like, oh, he's like a unicorn. He actually does this. So yeah, I'm all in on Bravo.

33:20

Yeah. I mean, my wife Leah's always like.

33:28

You need to get Andy Cohen to come to drive.

33:30

He's the best marketer there is.

33:32

D. Oh yeah, he's wild. He was a good dude and he played along. He was great.

33:34

Okay, what role do you think email plays for my audience? This audience here is B2B, Mid Market Enterprise. Types of marketers, what types of email strategy would you be thinking about? We're still in this world of like every brand kind of thinks they have to have a newsletter or they have content offers. They send out anything that stands out as like, you know, some strategy we can give out as it relates to email for these more, you know, marketers at bigger orgs.

33:38

Yeah. I would say in general, believe it or not, you're not sending out enough email, which I know is going to sound the opposite of what every meeting you're sitting in. Okay. And here's the reality of it. When you're in a meeting and they say, you know what, our email engagement's down. I think we're annoying people. I think we're sending out too much email and that's why it's not working. First of all, that's horrible math. The less email you send out, you're going to have less performance. I don't care what goes on. The problem is that you're boring people to tears. That's the reality of it. And here's the weirdest thing about email marketing now, as opposed to ten years ago. Ten years ago you used to go to the junker spam folder because you wrote the word free in the subject line or you capitalize something or something stupid like that. It was based on content that changed. Anybody that tells you that there are spam trigger words, it's garbage. That's from 1985. Whatever. The reason you go to the junk folder or spam folder now is based on engagement. How often are people clicking and interacting with your emails? If you don't have enough engagement, you as a sender into that network, you actually will go to the Junk folder and we'll go to the spam folder. The irony of email is you actually need to be sending out enough email generating enough engagement or you won't stay in the inbox. But then the game is okay. You convinced me we should be sending out more email. Which you should. It just needs to be better. And you need crazy subject lines, you need crazy headlines. You always want to think about email marketing like it's a chain and any break in the chain, it's gone, right? What is your friendly from? What is your from name? Is it just your brand? Are you just saying ACME or is it saying ACME Special content? Is it saying ACME Live event? Are you starting out of the gate with your friendly from your alias with something else besides just your brand name? Then what is your subject line say? What's the first one of your subject line? What's your pre header starting with? I'll give you a great example. On the pre header that people sleep on, that's that preview text, that second line of text. Okay. People say it's not important anymore because Apple doesn't show it all the time. Who cares? Nobody's using that feature yet on Apple. Your pre header is still very important. Here's secret sauce stuff for your pre header. If you start your pre header with one of these three words and but or plus and but or plus, they are continuation words. We are simple minded species, human beings.

34:02

Yeah.

36:17

Okay. When you read the subject line and then you see the word and or you see the word but or you see the word plus, all of a sudden you keep on going, okay, and we see it lift open rates significantly by using one of those three words. Because it's that chain. Get them to open, read the headline, the next thing, the next thing. So it's just about how do we keep them engaged. I talk a lot. I just talk.

36:17

No, you're good. I was just trying to think about like it's hard because your whole thing is like engagement. Like you actually want to get people to reply. And a lot of the ways that we use email at like a in a b2b.org is just like it's meant to just like deliver information.

36:39

Right.

36:55

If someone were to reply back, it would cause all these like, you know, ripple effects. Like we were just talking about this with our newsletter. The data is great, but I can get a feeling of how it went because of the responses that we're getting.

36:56

Well, by the way, I think that's a very important thing. Anne Hanley's been talking about This a lot, which is what she calls actual reply rate, which I think is a fantastic metric. So when you send out your newsletter and you encourage people to reply and you're looking at that rate, I do believe, and we're seeing it tested more and more. And this is a super awesome hack. And I'll tell you what everyone should do, all the B2B marketers out there. So what do we all do as a B2B marketer? We send out, we have a content piece that we want to promote. Right. It's the guide to whatever. You send out your email, say, hey, click here to download the guide, and you take them to some cheesy landing page and you hope that they download the guide. That's what everybody does. But here's the motion that markers are starting to test. That works like 300% increase in overall response rate. What you do is you send out your email, basically a short letter format, type email and say, hey, we have this new guide for whatever. If you want the guide, all you have to do is reply to this email and write the word guide. You're not taking them to the landing page, anything like that. Reply this email, right guide, and we will get you that guide. Now what happens in doing that? Number one, a lot more people do it than filling out the form. That's a win. But the secret hack is the number one way to stay in somebody's inbox in perpetuity is to get them to reply to an email that you send. It is a signal saying that you are interested in this sender. So when they reply guide to you, now you have this block, this technical lock that you're going to stay in their inbox. And also, by the way, you're in a dialogue with that person, which is also extra awesome. So this idea of what you just talked about, and not just anecdotally, like it felt like we got some replies, but actually using it as a response mechanism I think is a super great tactic.

37:08

Yeah, I love that we do it like in our newsletter. And that one works easy because it's like I wrote it. Hey, it's personal.

38:53

Yeah.

38:58

You know, what did you think? Reply back. I'm like, reply back to me. Yeah, Let me know what you thought. I do read every one of these, but you made me think of like the like reply guide thing. You could do that earlier on in like the welcome sequence and get that signal going right away. It doesn't just have to be in response to the newsletter.

38:59

Yep, agree.

39:13

Okay. Jay Schwedelson. I'm gonna rap with you because I'm gonna test. I'm gonna put my own. I'm like cut with you now because we're gonna put out a 37 minute episode which we usually do longer than that. And I'm gonna see you've jammed up my notebook. My mind is exploding.

39:14

Oh no.

39:27

Great to have you. People can find you you on LinkedIn. We'll link to all your stuff. Big fan of your work and I.

39:28

Hopefully I'll see you.

39:32

Appreciate you, man. You're a rock star. Thanks for having me on. Thank you.

39:33

Hey, thanks for listening to this podcast.

39:39

If you like this episode, you know what?

39:41

I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private.

39:43

Community for B2B marketers at exit 5.

39:51

And you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exit5.com our mission at Exit 5 is to help you grow your career in B2B marketing. And there's no better place to do that than with us at exit 5. There's nearly 5,000 members now in our community. People are in there posting every day, asking questions about things like marketing, planning, ideas, inspiration, asking questions and getting feedback from your peers. Building your own network of marketers who are doing the same thing you are. So you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days, so you can go and check it out risk free. And then there's a small annual fee to pay if you want to become.

39:53

A member for the year.

40:36

Go check it out. Learn more exit5.com and I will see you over there in the community. Hey, it's me, Dave. Our friends over at Customer I.O. are sponsors of today's episode. They're a really cool company that helps marketers turn first party data into engaging customer experiences across email, SMS and push. And they built their platform for marketers who actually care about the craft. Because marketing is a craft. It takes creativity, thought and taste. Right now, everyone thinks they're magically a marketer because they have access to AI and the result is kind of painful. More robotic emails, more noise, more bleh. AI isn't magic. It's not going to fix bad strategy or write great copy for you magically. But the best teams also aren't ignoring it. They treat AI as infrastructure. When it's built the right way, it actually makes marketing feel more human, not less. And that's what customer IO is doing. Their AI handles repetitive work like setup, orchestration, and tasks that should be automated so that you can focus on what actually matters. The craft of marketing, the strategy, the creativity. This is how good marketers are using AI right now. Not to replace thinking, but to support it. If this landed with you at all, this idea about the craft of marketing, I want you to go and check out customer IO. It's customer IO, exit 5. Go and check them out. Customer IO, exit 5.

40:38