Subject Line Tips That Are Working | Bathroom Break #117

Summary

The Marketing Millennials – "Subject Line Tips That Are Working"

Bathroom Break #117 • July 20, 2026
With Daniel Murray and Jay Schwedelson

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Episode Overview

This lively "Bathroom Break" mini-episode features Daniel Murray (The Marketing Millennials) and Jay Schwedelson (Do This, Not That Podcast, subjectline.com) riffing on creative, high-performing email subject line strategies. In characteristic banter-heavy style, Daniel and Jay rapidly share hands-on tips, observations, and quirky trends that marketers can use right now to get more email opens. The episode blends fun conversation about South Florida breakfasts and pickleball with a rapid-fire playbook of what’s working in subject line marketing for both B2C and B2B.

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Key Discussion Points & Insights

Warm-up Banter: Breakfast Clubs and Pickleball

Timestamps: [00:50]–[02:20]

• The duo jokes about South Florida social life, pickleball, and the oddity of people with strict breakfast meet-up routines.
• Sets a relaxed, relatable tone while prepping for fast actionable tips:
  • "I see those people. Yes, I do. And I judge them." – Jay, [02:07]

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Winning Email Subject Line Techniques

1. Use of Emojis

[02:54] Daniel:

• Emojis make subject lines stand out—help recognition if used consistently:
  • "I, I totally believe in emojis...people start recognizing you for a subject line."

2. Partial Sentences & Ellipses

[02:54] Daniel:

• Start a sentence and don’t finish, or end with ellipses "…". Increases curiosity and opens.

3. “How to” and List Formats

[03:20] Daniel:

• Practical, tactical subject lines like “how to…” or “best of…” work well.
• Numbers, especially odd or unexpected (7, 9, 11, 13), stand out versus round ones.
  • "Numbering but not like a clear number, like a 7 or a 9 or 11 or 13...always crush."

4. Human vs. AI Copy

[03:44] Daniel:

• Split-testing subject lines from AI (ChatGPT, Claude) vs. human-written.
  • Most times the human wins because AIs tend toward generic phrasing and avoid bold tactics (emojis, quirky numbers).

5. “Un-AI” Approaches – Jay’s Playbook

[04:50-06:10] Jay:

• Go the opposite of what predictably “safe” or AI-generated copy would do:
  • Super long subject lines (up to 100–150 characters). Fills up the space, creates pattern disruption.
  • Ellipses at the start of a subject line (not just the end) increases opens by ~15%.
    • "Super weird. Grammatically, it makes no sense, but that lifts open rates by about 15%" – Jay, [05:31]
  • No capitalization anywhere (stands out in an inbox, feels less AI-generated).

6. Audience Callout & Personalization

[06:23] Daniel:

• Directly calling out the audience in the subject line (“For marketers,” “Social Media Playbook,” etc.) boosts relevancy and open rates every time.
• Jay expands: "The sooner you could tell somebody who they are...the faster they want to engage. It’s the easiest trick in marketing." – Jay, [07:29]

7. Topical Keywords (AI, Timely Trends)

[06:45] Daniel:

• Including “AI” in subject lines (e.g., “AI Prompt Inside”) taps into trending curiosity and drives higher opens.
  • “If you say AI prompt inside, forget about it. That’ll Crush it.” – Jay, [07:20]

8. Serialized Subject Lines

[08:15] Daniel:

• Number subject lines as a series (“Edition #1,” “Tip #2”, etc.). Promotes binging and FOMO—readers want to check previous or missed editions.

9. Repurposing (Vault) Content & SEO

[09:09] Jay:

• Host your newsletter archives on your site for SEO upsides and to drive traffic via referral links (e.g., “Missed last week’s newsletter? Read here.”)
• “Vault” approaches (best-of roundups, exclusive access to archives) can make for enticing content offers.

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Notable Quotes & Context

• On Ellipses at the Start:
  "Actually using them at the start of your subject line... that lifts open rates by about 15%."
  – Jay, [05:31]

• On Direct Audience Callout:
  "The sooner you could tell somebody who they are... the faster they want to engage... It’s the easiest trick in marketing."
  – Jay, [07:29]

• On Serializing Subject Lines:
  "Did I miss number two? Did I miss number four? ...I’ll go back and read, go read 82, 81, 80."
  – Daniel, [08:15]

• On AI in Subject Lines:
  "If you say AI prompt inside, forget about it. That’ll Crush it."
  – Jay, [07:20]

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Fun Moments & Light-Hearted Asides

South Florida Social Rituals

[00:50]–[02:20]

• Jokes about avoiding recurring social gatherings and breakfast groups, setting a friendly, irreverent tone.

Taco Bell, Salads, and Influencer Dilemmas

[11:15]–[12:49]

• Reference to the then-current Taco Bell lettuce news and marketers’ willingness to do (or avoid) influencer stunts for brands.
• Daniel shares, "I love Taco Bell breakfast, which is probably weird to say." [12:04]
• Jay quips: "That’s the new joke, right? I mean, sort of like Ozempic. Just go to Taco Bell and eat a salad." [12:44]

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Essential Timestamps

• [02:54] – Daniel starts rapid-fire subject line tips: emojis, partial sentences, “how to,” odd numbers, AI testing
• [04:50] – Jay’s “Un-AI” subject line hacks: long lines, creative punctuation, all lowercase
• [06:23] – The power of audience callouts and “AI”-themed subject lines
• [08:15] – FOMO and engagement by serializing newsletters
• [09:09] – Underrated value of SEO and “vault content” from newsletter archives
• [11:15] – Podcast veers into Taco Bell/lettuce headline, showcasing marketing’s overlap with pop culture

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Takeaways for Marketers

• Don’t play it safe: Stand out with formatting, punctuation, and playful twists that AI won’t suggest.
• Specificity and personalization drive engagement—call out your audience directly in subject lines.
• Experiment with trends and keywords (“AI,” “prompt,” etc.) to stay relevant and boost opens.
• Leverage numbering and serialization to foster habitual readership and archive exploration.
• Always double up: Repurpose newsletter content for website use and link between platforms for greater reach.

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Final Word

The episode wraps up with a reminder: every marketer benefits from quick experimentation and a willingness to challenge conventions—even if it means using a weird emoji, a 120-character subject line, or putting “AI” where you wouldn’t have dared last year.

"Go follow The Marketing Millennials and Do This, Not That Podcast—see you on the next Bathroom Break!"

Transcript

[A]

If Taco Bell came to you right now and they said, we want you to go and film this, go to a Taco Bell and eat a salad at Taco Bell and they were going to pay you a significant amount of money, would you do that?

[B]

Welcome to a new special series called the Bathroom break. That extra 10 minutes you either have to listen to marking tips or use the bathroom or both. But I don't recommend both. But that's your choice.

[A]

This collab going to be super fun. We have Daniel Murray from the Marketing Millennials and me, Jay Schwedelson 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.

[B]

We are back with another bathroom break. I am here with the Jay Schwedelson and I wanted to kick this off because I have a question for you because I know we both live in South Florida and I know you like starting to get into pickleball. So like, do you like pickleball and you play pickleball at a conference? Like, are you like becoming a full time pickleball person? Like, what's going on with that?

[A]

No, thanks for asking that. I really appreciate. No, I suck at pickleball. The problem is that I took a few lessons and then everyone keeps saying to me, hey, dude, you got to get into a game. And then everybody like, you'll meet up with these people and you'll play every week. But the problem with that is then I have to meet up with the people and I have to talk with them and I don't really like that part of my human experience. So let me ask you a question. Do you do anything on a weekly basis where you have to meet up with a set group of human beings and interact with them?

[B]

No, like, even more like tennis. I like switch up the people I meet up with.

[A]

Do you think it's weird, like if you have like a, somebody plays in a golf game or, or, or, or you meet up and, and you do something, like you meet up for a same lunch group every week. Don't you think that's a bit.

[B]

No, I, I, I, I, I, I see like a lot of people who have like these little breakfast groups. Do you see them?

[A]

I see those people. Yes, I do. And I judge them. Yeah.

[B]

Every morning they're like, and they like talking about some of the same things every single. Yeah, it's like who does breakfast group?

[A]

I, I, I see the breakfast groups. I know exactly. I'm always like, why are you guys meeting up every morning? You guys are weirdos. I don't know, maybe it's, maybe you and I are weird, but we probably are. But you know what's not weird? Our subject lines. Everyone loves subject line tips. Why not? And Daniel and I are always messing around for our brands, for my clients brands, whatever. What is getting stuff open for business and consumer marketers. So Daniel, let's rip through some subject line tests that people could try right now. Super easy. Give us some of your favorites and I'll give you some of my favorites.

[B]

I mean, I'm just going to go on a tried and true one. I, I, I, I, I totally believe in emojis. I totally believe they are way in two different ways. One, I think they stand out in, in a subject line. But also if you're trying to be consistent and do something consistent over time, people start recognizing you for a subject line. So I think one is emojis. I love, I love ending like having partial sentences, like starting a sentence and not ending it and putting or putting ellipses at the end of it. I think those always crush, crush for me. Another one that also crushes for me is I always, when I put like how to or like some, something that's like very practical like how to or best of or people love like, like tactical things that they could do right now. And I know one that I learned from you, which I use all the time is like numbering but not like a clear number, like a 7 or a 9 or 11 or 13. I use that all the time. And those always crush comparative to all the stuff. And I've also been doing something lately. I don't know if you've been like a split testing if ChatGPT or Claude can come up with a better subject line. So I'll put like Claude versus me. And most of the time, like the human win. Sometimes I get beat out by it. But I think just because I know like these little tips that if you try to do it in AI, they're not going to tell you to put an emoji or a 7 or a 6.5 or crazy stuff. They'll just try to put like a sentence together. So those are some, I'll come up with more once you, you rattle for yours.

[A]

Yeah, I'll give you the one. Speaking of AI, the ones that we were doing a lot are actually the ones that I like to call unai. So subject Line formats and things that AI would never give you back. So I'll give you a few examples of what's really doing well. And you're gonna be like, well, I'm a boring B2B2B brand. I can't do that. That's not true. Everything. Everything is for everybody. First off, super long subject lines. People was like, keep your subject line under 50 characters or 60 characters. It's not about that at all. It's about how do you get somebody to pause doing that, that, you know, millisecond social scroll. And if you actually have subject lines that are like 100 characters, 150 characters, what you want to be thinking about is space. And if you fill up the entire line, your email actually stand out and it will get cut off. But that actually works so well. Incred long subject lines do really, really well. Two other ones that are super weird. You know, Daniel talked about ellipses, the. The three dots at the end of the subject line. But actually using them at the start of your subject line, it works really well. It's super weird. Grammatically, it makes no sense, but that lifts open rates by about 15%. And then some of the other ones that I think are off the radar is no capitalization whatsoever. So again, poor grammar. But AI will never tell you to not capitalize the first letter of a word or whatever. But if you capitalize nothing in your subject line, it actually stands out a little bit. And that's what you always want to be thinking about. What can I do to make my email not feel like AI and stand out a little bit? And those things actually can work.

[B]

I think another thing to add, and I know this is like a repetitive thing that we both say, but just like calling out your audience. And the subject line always crushes it. Always. Every single time. I've done like marketers or social media playbook, like social media or something that pertaining to my audience. My audience marketers. It always crushes because it shows relevancy in the subject line. And I never backing away from that one because every time I back away from it, I always get screwed. I think another one is, I know this is people. Everything's AI. But I think adding like AI this, AI that, like I do a like say like if you have the best of AI of this, people are trying to get AI tips right now. Like whether you like or not, people are. So if you add AI into also will like boost your subject lines too.

[A]

Oh, 100%. If you say AI prompt inside, forget about it. That'll Crush it, you know, but back to what you were before. And I think this applies not just to subject lines, but to headlines in your social posts, your blogs, your offers, everything. The sooner you could tell somebody who they are, this applies to all marketing. The faster they want to engage. You know, just for DIYers, for nonprofit executives, for people that live near Omaha, whatever it is, for affluent investors, just for golfers, for people in the manufacturing sector. The sooner somebody could see that in the social post, on the headline of a landing page and the headline of your body copy, in your subject line in a podcast, they're like, oh, this is for me. It's not for everybody. So you always want to be thinking to yourself, what, what can I do to make the recipient or the person seeing this thinks that it is for them? Because then they will engage immediately. It's the easiest trick in marketing, I

[B]

think one that you, you've said. But I do think it, it works if you start off like this. But it, if you don't start off like this, it doesn't work anymore. Is like if you're doing, like I said, the emoji. If you do serialized sends. I used to have another newsletter and I used to do like, like 1, 2, 3. I just give someone something consistently to look back, look at, but also like will make people be like, where is, did I miss number two? Did I miss number four? Did I miss number 55? Like, where did I miss another one? And they'll go back. I know I read a newsletter that does that and I'm like, oh, I missed like 79. We're already at 83. So I'll go back and read, go read 82, 81, 80. Because I'm, I, I missed those ones and it made me think.

[A]

And that's what we do. You know, I've been doing that, my newsletter, we make it, it's an addition thing. We put the addition at the start of each subject line. But the other thing you always want to be doing with basically all of your emails, but especially any newsletters or business consumer, doesn't matter. You want to make sure that those newsletters are also living on, on your website from an SEO perspective, from an AEO GEO perspective, especially with that edition based stuff, because people want to go back and look at the other editions of your newsletter. But if you're not making sure that your newsletter, all of the content is also living on your website, you are just not using that content properly at all.

[B]

And it's also a good way you can like something you could do is refer back to it and. And put the link. And that is really helpful too is like be. Hey, you missed this one. Here's this, here's a link to it and drive to the website now.

[A]

So now easiest kind of content is vault content. You take like some of your best content, you throw it into an offer and say, unlock the vault. Get access to our top 10 best, you know, offers our top 10 best, you knowhall podcast, blah, blah, blah. Just make a vault of any of your content and that actually will. Will do phenomenal. So let me add back to the beginning thing where people are meeting up for breakfast and all this stuff. If somebody invited you in and say he Daniel, hey man, I see you just moved here. We got this group that gets together every morning. We'd really love for you to hang out and come meet with us. Are you just like, would you just be like, no or would you say sure? And then you go once and you ghost them like, how do you handle that invitation?

[B]

I just use the best excuse in the book that I have right now. Sorry, have a kid. Kid first. Sorry. Oh, the kid's going good napping at that time.

[A]

No, you're not going to. I think it's wildly inappropriate if we don't talk about one topic before this episode ends. Right now there's a lot going on about Taco Bell and people going to Taco Bell having some lettuce by accident and then running into some bathroom issues. Are you aware of what's going on with this thing that's spreading across the country?

[B]

Yeah, I put in my newsletter today. I'm so thankful that lettuce is not having its day anymore. I'm so thankful that people aren't eating salads anymore. I'm so thankful that I don't to have to hear one more person talk about lettuce for and also it's funny because I'm laughing is because every time we go out to dinner with my wife's family, we'll order the most unhealthiest things and they'll be like, but you forgot a veggie. Now there's not going to be forgot a veggie because they're all scared of veggies now.

[A]

Well, let me ask you a question. You take influencer deals, right? If Taco Bell came to you right now and they said, we want you to go and film this, go to a Taco Bell and eat a salad at Taco Bell and they were going to pay you a significant amount of money, would you do that now?

[B]

First of all, I'm not like, the biggest, like, Taco Bell person. My Ari is the biggest Taco Bell person. I love trying to convince it. I like Taco Bell breakfast, which is probably weird to say.

[A]

You eat Taco Bell breakfast?

[B]

Yeah, I've had it before.

[A]

What is that? Like, what are you, a egg?

[B]

They have, like, breakfast chalupas, breakfast tacos. Like, it's pretty good. You should try it.

[A]

Would you go this week?

[B]

You're going to do a Taco Bell breakfast club?

[A]

Yeah, that I might do. That I might do. I'm going to get you a salad from Taco Bell. I'm going to do that.

[B]

No, I mean, it might be a good. I've seen people say they lost, like 15 to 20 pounds on.

[A]

I know. That's the new joke, right? I mean, sort of like Ozempic. Just go to Taco Bell and eat a salad.

[B]

Yeah, but I don't think I want to be down and out for five days because I got a parasite in me. No way. I'm. There's better ways to do it.

[A]

There's got to be better ways. Well, it's also gotta be better podcast, because, you know, what did we just discuss? But appreciate you being here. Go follow the marketing Millennials. Go follow. Do this, not that podcast and we'll see at the next one. Daniel, come on, man. I gotta 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 I hope you give it a try. Oh, here's Daniel. He's finally out.

[B]

Back from my bathroom break. This is Daniel. Go follow the market Millennials 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. A shout on LinkedIn and tell us what you want to hear. Peace out.

[A]

Later.