How AI is Changing Email | Bathroom Break #124

7 Sep 2026 · 11 min · 4 chapters

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In short

AI email “live text” summaries (Gmail/Apple Mail/Microsoft Copilot) and how to structure emails so the AI extracts the right details into inbox summaries or the preheader.

Guests

Jay Schwedelson (Do This Not That; subjectline.com) and Daniel Murray (Marketing Millennials).

Key claims

AI summaries pull the most important content from the first ~150 characters of the email HTML “live text,” often replacing the written preheader. Copilot is rapidly growing (30M paid users, +10M in one month), so this affects both consumer and business marketers.

Notable examples

webinar details or offer specifics should appear in the first 150 characters; avoid critical info in images (JPEGs) because AI doesn’t scan images for live text; alt text doesn’t count as live text.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Festival Talk with Daniel

0:41 to 2:26

Casual discussion about festival experiences and preferences.

“All right, we are back for another bathroom break.”

AI and Email Marketing Insights

2:26 to 6:33

Discussion on the impact of AI on email marketing and optimization strategies.

“For people who don't know, an SEO or like in Google, there's like AI overviews for search.”

Adapting to New Email Trends

6:33 to 8:16

Exploration of changing email strategies due to AI and live text.

“So like really like your subject line is the first line of the email, the preheader is the second line.”

Festival Experiences and Preferences

8:16 to 9:50

Light-hearted conversation about personal festival experiences and preferences.

“Speaking about losing the battle, I have a question for you.”
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Transcript

Automatic transcript. May contain errors.

0:07Jay:Welcome to a new special series called The Bathroom Break. That extra 10 minutes, you either have to listen to marketing tips or use the bathroom or both. But I don't recommend both, but that's your choice. This collab is going to be super fun. We have Daniel Murray from the Marketing Millennials and me, Jay Schwetelson, from the Do This Not That podcast and subjectline.com. Each episode in the series, we are going to go over quick tips about different marketing topics. And if you want to be in the bathroom, fine. Just don't tell us about it. Thanks for checking it out.

0:41All right, we are back for another bathroom break. This is Jay Schwedelson from Do This Not That. I'm here with Daniel Murray from the Marketing Millennials. And not only is it, we're going to be talking about something important in email that people aren't talking about enough live text. But before we do that, it is not only conference season in the world of business, but it's also festival season. I saw Burning Man's going on. Daniel, I feel like when you go to like a festival or something, you have like lollipops and neon stuff all over you. And you're just a disco inferno. Is that an accurate view?

1:15Jay:No, it's not very accurate. But I did go to Coachella five years in a row. Wow. Back in the day. and it's changed a lot but like I was never a camper Ari once camped and you can ask the question about camping but I'm watching all these influencers at Burning Man and it looks like Mad Max out there have you seen that movie Mad Max? yeah so how would you handle Burning Man? like would you be in like a bikini made of suede? like what would you be wearing? I would never be caught at Burning Man I need like access to like running water I know that's bad to say but I'm not a camper and I've never been I didn't grow up camping I can't I mean the furthest I'll camp is like in the backyard but I'm not a camper Have you ever made a s'more?

2:03Jay:Oh for sure made a s'more but not that's like the depth of camping I would do That's where your camping ended after you made a s'more? And then after I got roasted about not having a toolkit now they're going to roast me that I don't have a I don't camp. A tent. You do not own a tent. I don't own a tent. Yes. So what are we talking about today? For people who don't know, an SEO or like in Google, there's like AI overviews for search. But now since AI is in every tool, Gemini, a copilot for Microsoft, which are attached to all these email providers. now they're showing live texts or like summaries of what emails are coming on.

2:53Jay:And Jay was telling me some strategies of like how to do, how to like appear in these live texts. So Jay, you want to tell us a little bit of how to get the, like what is important in your email to be shown there? And why is it even important to be like, like optimized for this live texts and emails? Yeah, I think it's a big topic. So if you ask me what in the next 12 months, can be the most important thing in email marketing, it would be what's called AI summaries. Now, some of you already may see AI summaries in Gmail. Maybe if you use the Apple Mail app, you may see these summaries, but it's exploding.

3:28And what it's basically doing is AI is looking for the most important part of your email. And then it's pulling that information either into a summary at the top of your inbox, or it's pulling that information into the pre-header of your email, that second subject line. and it's removing the preheader that you put there. Now, I'm going to tell you exactly what you want to do to have the right stuff show up. But the reason this matters for consumer and business marketers is that Copilot within Microsoft has really exploded. It now has 30 million paid users. That's up 10 million paid users in just one month.

4:02And there's so many millions being added every single week. So this is going to be for business consumer. It doesn't matter what kind of email you use or what promotional email you send out. Now, here's the thing. What live text is, that's what the AI summaries are looking for. It's looking for what's called live text. Live text is just that. It's text in your emails that's in the HTML code. It's that 1994 style hyperlink that you could read the letters of the hyperlink. It is not image-based stuff. So what you want to be thinking about is in the first 150 characters of your email, that is what the AI summaries are looking for is stuff in that first 150 characters.

4:41and you want to be very authoritative. If it's a webinar, it's the details of your webinar. If it's an offer, it's the details of your offer. The first 150 characters are everything. And what you don't want to do, you can't have a JPEG, an image that has critical information in the image because the AI summaries are not scanning images for any live text. And then the other thing that's confusing out there is that alt text. So when your images don't appear and you have alt text, when your images aren't there, all text no matter what you do is not live text it does not count as live text so you need to actually have live text at the start of your emails i have a question for so i want to hear

5:20Jay:how you think about this because like the the the subject line and the preheader is always like meant to like get the open right um so is it do you think you in your first couple you need to like kind of bait it a little bit so it doesn't give away your whole email so nobody opens it or should Should you give it all that's what's in the email so the consumer could decide open or not open? Yeah, I would say within the next six months, 50 % of pre-headers are not going to be the pre-header that you wrote. It's going to be an AI extracted thing from your message that's going to be sucked into the pre-header spot.

6:03So right now you still want to play the same pre-header game that you've always played. But what you really want to be thinking about is that first 150 characters, you basically almost want to say whatever it is you were going to say in that preheader or say the hook that you want to use. Because about 50 % of the time, that's actually what's going to be showing up in the preheader. So the whole game is going to change. The subject line is not changing at all, but everything else is.

6:29Jay:Yeah, I've always learned like, I mean, the preheader is the second line of your email. So like really like your subject line is the first line of the email, the preheader is the second line. So like you'd be thinking about subject line preheader. Like now you got to think of your second line also being important in your body. You met where before you would go like subject line preheader, then whatever else you were going to say to like follow up on that preheader. But now you have to like also think about that it might not pull what you're trying to do in the preheader. So make sure that you basically say sort of the same thing.

7:07Jay:You don't have to say the same thing as you want to say, but close so it pulls in what you would put in that pre-header. Yeah, and the other last piece I would play in everybody's mind is the prettiest email is no longer winning. It's not about what's the slickest design, what do your images all look like. You have to play the game for what these AI summaries are looking for. So you're going to have to go back to your templates, go back to your stuff, and don't just be like, It has to be this because you're going to lose. Because in a weird way, we're going back like 10, 15 years as it relates to the way that emails need to be structured.

7:38Jay:I think this is even a deeper thing to discuss about like there's AI summaries on emails, but then now like you're getting on like Apple phones and text messages, like even those summaries. So like starting to optimize for like, how do I get into the bulk like summary that Apple is showing or the text message? So if you're doing like SMS marketing or how do I make that one line so important to get that? I still have to learn that. So I'll come back later and make sure we can talk about that. But I think there's so many summaries that you need to think about right now. And if you're not being shown in them, you're losing the battle against other people who are showing in there.

8:19I totally agree. Speaking about losing the battle, I have a question for you. You're a big dude. You're like 6 '5", D1 football player. When you used to go to Coachella and there was one of the musicians, you're like oh I'm really into them did you just body everybody and get right to the front of the stage and did you like just mosh pit right to where your spot was because I feel like you could

8:37Jay:truck everybody um I always used to be like the person who like when in the group that would guide people to like like they were attached to me and I would go through like the crowd created the path yeah I created the path um but also like what something that's really annoying I think is festival and I get the reason but it's also like I also believe like in concerts there's like a first come first or more like a you you you get your spot and you get your spot like but since I'm a tall guy people assume that like oh you can go further back because I'm shorter and I'm like no no no like because then it becomes like someone goes on someone's shoulder that someone goes on and then you're then you're behind a person on their shoulder who's way taller than you so uh So, yeah.

9:26Jay:Festivals are interesting. I don't think, I have too much anxiety to go back to a festival like that. I don't like sweating next to people that are sweating. You live in Florida. That's like the epitome of Florida. I know. That's why I don't leave my home. I like to be sweating next to people who are sweating. Everybody's sweating in Florida. I know. Everyone's disgusting. I'm disgusting. We're all disgusting. But you know what's not disgusting? This episode. This episode was the opposite of discussing. Listen, follow the show. Leave Daniel a review. Leave me a review and go sweat near somebody.

10:04Daniel, come on, man. I got to get back to work. Get out of there. All right. While he's still in there, this is Jay. Check out my podcast, Do This, Not That for marketers. Each week we share really quick tips on stuff that can improve your marketing and hope you give it a try. Oh, here's Daniel.

10:19Jay:He's finally out. Back from my bathroom break. This is Daniel. go follow the Mark and Millet podcast, but also tune into this series. It's once a week, the bathroom break. We talk about marketing tips that we just spew out. And it could be anything from email, subject line, to any marketing tips in the world. We'll talk about it. Just give us a shout on LinkedIn and tell us what you want to hear. Peace out. Later.

From the publisher

AI is already reading your emails before your subscribers do, and if you're not writing for it, your message might not make it to the inbox at all.

Jay breaks down "live text," the actual HTML text in your email that AI tools like Gmail summaries and Microsoft Copilot scan to build inbox previews and rewrite preheaders. Copilot alone just hit 30 million paid users, up 10 million in a single month, so this isn't a niche problem. Jay's rule: the first 150 characters of your email need to carry your most important, most specific information (webinar details, offer terms, whatever the ask is) because that's the window AI summaries pull from. Images and JPEGs don't count, and alt text doesn't count as live text either, no matter what you've been told. He predicts that within six months, half of all preheaders will be AI generated instead of whatever Marketers actually wrote.

Daniel adds that the preheader isn't dead, it's just unreliable now. His fix: write your opening body copy so it echoes what you'd want the preheader to say, so if AI does pull from it, the message still lands the way you intended. He also flags that this isn't just an email problem. The same summarization behavior is starting to show up in text messages, and Marketers need to start thinking about how their SMS gets condensed too.

The bigger idea: the prettiest, most designed email templates are losing right now. If AI can't read the words inside your design, it doesn't matter how good it looks. Email Marketing is quietly reverting to a text-first format, closer to how it worked 10 to 15 years ago.

If you want your emails to survive the next wave of inbox AI, this is the episode for you.

Follow Jay:
LinkedIn: https://www.linkedin.com/in/schwedelson/
Podcast: Do This, Not That

Follow Daniel:
YouTube: https://www.youtube.com/@themarketingmillennials/featured
Twitter: https://www.twitter.com/Dmurr68
LinkedIn: https://www.linkedin.com/in/daniel-murray-marketing

Sign up for The Marketing Millennials newsletter:https://themarketingmillennials.com/

Daniel is a Workweek friend, working to produce amazing podcasts. To find out more, visit:https://workweek.com/

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