SPECIAL SERIES ==> Stop Sending Emails at 9 AM 🛑 <== | BATHROOM Break #93 COLLAB: The Marketing Millennials + Do This, Not That

Summary

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Podcast Summary:

Do This, NOT That: Marketing Tips with Jay Schwedelson
Episode: SPECIAL SERIES ==> Stop Sending Emails at 9 AM 🛑 <== | BATHROOM Break #93 COLLAB: The Marketing Millennials + Do This, Not That
Date: February 2, 2026
Guests: Jay Schwedelson (Do This, Not That, Subjectline.com), Daniel Murray (The Marketing Millennials)
Main Theme:
Unlocking actionable marketing automation strategies—making automated outreach more personal, impactful, and less robotic. Includes bonus personal tips for Valentine’s Day, interwoven with lighthearted banter.

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Episode Overview

This special collab between "Do This, NOT That!" and "The Marketing Millennials," hosted by Jay Schwedelson and Daniel Murray, focuses on transforming marketing automation from generic and ignorable to engaging and personalized. The duo share rapid-fire tips for marketers to make their automations stand out while weaving in a playful, Valentine’s Day sidebar that serves to humanize the hosts and kickstart practical gift-giving advice.

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Key Discussion Points & Insights

1. Valentine’s Day as a Marketing Analogy [00:19–02:01, 08:26–10:25]

• Opening Banter: Jay teases Daniel’s romantic side and uses the approach to relationship milestones as an entry point for “automation” in love and in marketing.
• Daniel's Advice: Don’t save appreciation for special days—do it all year round. Celebrate on alternative dates to avoid clichés like overpriced menus.
  • Quote: “Sometimes it's better to celebrate the day before or something. So you don't get these prefixed annoying menus that they have that are overpriced.” (Daniel, 01:32)
• Jay’s Advice: Shop for gifts together to avoid disappointment and get the perfect gift; document hints throughout the year.
  • Quote: “Now I've come to this place...where we shop together. Where I am no longer like, surprising her. You know, because I am clearly very bad at this.” (Jay, 09:16)
  • Quote: “When your significant other is mentioning something that they want, document it. I have a notes in my phone of things Ari wants.” (Daniel, 09:28)

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2. Making Marketing Automations Feel Personal [02:01–03:55]

• Daniel’s Tactics:
  • Use personalized language in automated DMs (mentioning weather, location, or specific details) to spark real replies—even if users know it’s automated.
    • Quote: “I say I'm currently enjoying the weather in whatever area where are you right now? And I get tons of replies...either like you're so lucky or like oh I know this is automation but this is really good automation.” (Daniel, 02:49)
  • Inject GIFs, memes, and multimedia (like a Yoda gif in welcome emails) to make automations lively, fun, and branded.
• Key Insight: People interact more when automation doesn’t feel automated.

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3. Mixing Human Touch with Automation [03:55–05:02]

• Jay’s “Over-the-Top” Strategy:
  • Send unplanned, human-written one-off emails on top of automated flows without turning the automations off.
  • Uplifts engagement and business results as it “wakes up” recipients.
  • Quote: “We’ll have emails that go out...that is really just a one-off written by a human being...in addition to [the] email… The ones with over-the-top would do phenomenal.” (Jay, 04:12)
• Takeaway: Never “set and forget” your automation; human touchpoints amplify results.

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4. Advanced Automation Tips [05:02–06:42]

• Daniel’s Recommendations:
  • Keep marketing—add incoming leads to advertising audiences for retargeting and education, not just email nurture.
  • Use automations to create exclusion lists for more tailored ad spend.
  • Employ data enrichment automations: collect, segment, and personalize based on enriched vs. unenriched data.
    • Quote: “If you're collecting first-party data too, that can help as well.” (Daniel, 06:28)
• Key Point: Automation can and should extend beyond email, encompassing ads and layered segmentation.

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5. Timing and Authenticity in Automation [06:42–07:43]

• Jay’s Rant:
  • Avoid scheduling all automations for common “best” times like 9 a.m.—it creates forgettable, ignorable “wallpaper.”
  • Use odd times, like “8:07 pm,” to stand out.
    • Quote: “What you don't want to do is...all of our stuff's going to go out at 9am... That's a fail. Then you're literally creating wallpaper.” (Jay, 06:55)
  • When automating social media, be live to engage with comments in real-time; otherwise, posts go “dead on arrival.”

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6. Platform & Channel-Specific Personalization [07:43–08:26]

• Daniel Notes:
  • Use tools that adjust automation timing/channel based on audience preference (SMS, email, social).
  • AI can now fine-tune messaging and timing.
    • Quote: “Generic automations are kind of dead. They know people are going to do it... Figure out ways to be more personal, more timely, more relevant…” (Daniel, 08:10)
• Takeaway: Personalize automations at every touchpoint—one-size-fits-all is over.

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Notable Quotes & Memorable Moments

• Personalization, Even When Recognized:
  • “Oh, I know this is automation but this is really good automation.” (Daniel, 02:53)
• Surprise-and-Delight Human Touch:
  • “It wakes them up a little bit.” (Jay, 04:22)
• Automations Shouldn’t Be Set and Forgotten:
  • “Treat automations like they’re not automations.” (Jay, 07:18)
• The Death of Generic Automation:
  • “Generic automations are kind of dead... be more personal, more timely, more relevant.” (Daniel, 08:10)
• Valentine's as Metaphor:
  • “Now I’ve come to this place... where we shop together. Where I am no longer like, surprising her.” (Jay, 09:16)

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Timestamps for Key Segments

• 00:19 — Episode intro, Valentine’s Day banter & analogy
• 02:01 — Jump into marketing automations; making automations feel real
• 03:55 — Overlaying human-written emails with automation cycles
• 05:02 — Power of advertising automations, data enrichment, smart segmentation
• 06:42 — Don’t automate at obvious times; breaking the “9AM” mold
• 07:43 — Tools, AI, and the need for channel/personalization focus
• 08:26–10:25 — Personal Valentine’s Day gift strategies (bonus, analogy to personalized marketing)

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Summary Takeaways

• Humanize your automations: Use language, visuals, and timing that set your outreach apart. Recipients notice—and respond to—even “fake” personal touches when done creatively.
• Layer automation with real human interaction: Insert spontaneous, unscripted, or individually written messages into your journey; these “wake up” your prospects.
• Segmentation and timing matter: Avoid predictable patterns; leverage unique time slots and channels tuned to your customer’s consumption behavior.
• Automation should cover the whole funnel: Move beyond just email; automate ads, data enrichment, and exclusions to keep your approach holistic.
• Don’t set and forget: Even the best automation needs a human to breathe life into it—track, tweak, and interact in real time.

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For more actionable marketing tips and quick-hit strategies, listen weekly to the Bathroom Break series. For upcoming topics or to suggest your own, connect with Jay and Daniel on LinkedIn.

Transcript

[A]

Foreign.

[B]

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.

[A]

This collab is 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 top and if you want to be in the bathroom, fine, just don't tell us about it. Thanks for checking it out. We are back for the Bathroom Break. I'm here with Daniel Murray, the marketing millennial. I'm Jay Schwedelson from Do this, not that. And before we get in, we're going to be talking about automation streams. Very exciting. But what is exciting, I'm curious, is not too far away is Valentine's Day and people don't know this about Daniel. Extremely romantic guy. He's like Cerno de Bergerac. He writes poems and sings these songs to Ari. It's unbeliev. So Daniel, I know you must plan months in advance. So do you really plan seriously for Valentine's Day as it's approaching?

[B]

I believe like this is cheesy to say but I think you should do what you do on Valentine's Day tons during the year anyway for your significant other. So I think there's the romantic of me but I do think that it's a carved out date. So I like to plan a dinner, get a little gift. This year I want to do like a gift from our son to her idea. So like something cute like that. So yeah, I do think that. But I also do think like sometimes it's better to like celebrate the day before or something. So like you don't get these prefixed annoying menus that they have that are overpriced. So that's an option as well.

[A]

There you go. I love it. I love it. Well, there you go. You got the, you got the Valentine's advice from Daniel. So let's jump into it though about we're talking about automations. There's a lot of things out there that we all automate. Whether you're a business marketer, consumer marketer, whatever, non profit, you're automating people, going to a landing page, filling out a form, an email goes out, you're automating certain social posts go out at certain times, you're automating some of your outbound sales outreach emails, people that didn't open an email, you're sending this, that whatever. So Daniel, kind of give us what are some quick win tips for people's automations that maybe is not on their radar.

[B]

I think one thing is make your automations feel personal and you could do it in a generic way. So for example I have this like DM automation in my community that I say like I saw you scrolling and I saw your name pop up and I wanted to reach out and say how are you doing? Blah blah and I say I'm currently enjoying the weather in whatever area where are you right now? And I get tons of replies either like you're so lucky you're in warm weather or like oh I know this is automation but this is really good automation. So when you're doing automation always make it feel personal, fun, part of your brand. I think another layer to add on is adding GIFs or multimedia stuff into to make it feel like more fun. So like in my welcome email I have like a Yoda meme like I mean Yoda gif. So it's like do little things like text messages now you can add gifs in there. So in your automations add things to make it more personal, more fun, more relevant to your audience.

[A]

Yeah, in general you do a really good job of that. The more that you can make your automations not feel automated, the more that people interact with them and you actually get business. And the other thing that we've tested which is really interesting is we like to also come over the top on our automation streams with our clients. So our clients set up automation streams could be some sort of B2B SaaS product or some sort of, you know, direct to consumer play, whatever that they have the automation streams already all set up. But then we'll have emails that go out for example that are over the top again in addition to email that'll go out to the same population of people that is really just a one off written by a human being email. And we're not pausing the other automations but we're doing it in addition to. And we looked at those scenarios where we just had pure play automation and then we had automations with kind of some of these over the top where we inserted them and the ones with over the top would do phenomenal. They would just get us so much extra because people are like whoa, what's this? It wakes them up a little bit. So I think you can't just do this, set it and forget it and think it's just going to be this Always on thing that's going to make you money. It just doesn't work that way anymore.

[B]

I think there's like other things you could do in automation. I think one thing, I think people make a mistake is to stop doing advertising to those people. So when they, when they do come in your funnel, having that as a list in your, in whatever tool you're using to collect emails and have an automation to funnel that as a, an audience in your, to run educational stuff. So you stay top of mind because now you've got them in one point of funnel, now you need to educate them anymore. So do some air coverage type advertising. And also you can add that as an exclusion list too now to some other things you're doing as well in advertising. So that's another automation to think about is like now I can put this in a different bucket of advertising and I can also create an exclusion list for people who are for this part of advertising. So that's another thing that I think about is how to automate that to keep marketing them on other. Because now you have the email and then obviously then another level of automation is if you have a tool that can get more information about enrich that data. So having an enrichment automation so then you can start getting more personalized data and then separating enriched versus not enriched and being able to personalize both those lists and have an email for unenriched versus enriched people, that's another way. And if you're collecting first party data too, that can help as well. So there's some automations I think about as well.

[A]

Yeah, I love all that. And there are also some simple things that you could do with your automations. I think people miss on. So for example, if you're doing email automations you got all these different triggers based on what they do, did or haven't done or fallen off or this, that or whatever. What you don't want to do is like all right, all of our stuff's going to go out at 9am or 6am or 11am That's a fail. Then you are literally creating wallpaper. People start to get accustomed to the garbage that you're doing. Have automations go out at 8:07pm at night. Have automations do things that are so counter to what everything else is and that's how your automation is not going to feel like an automation. The worst thing you could do is just be checking a box and be like well we turned that on. It's going. It's the same thing with social posts. If you're automating all your social posts and then you're not taking the time when they post to actually interact in that first hour when people are interacting with the post that you just automated and your company just automated, those posts are going to be dead on arrival. So treat automations like they're not automations.

[B]

And there's like tools out there that can have automations be more timely and more platform based. So, like if people are more a text message audience versus email versus social, you can more timely hit those people on different types of. And now with AI, you can get more in depth with that as well. So there's things that you could do too that are not generic. I think generic automations are kind of dead. They know people are going to do it, you're doing it. So figure out ways to be more personal, more timely, more relevant in the inbox to be even seen by that consumer.

[A]

I love that. So, all right, back to the Valentine's Day thing. Do you write poems?

[B]

No, but I feel like you're a poem guy. What do you do for Valentine's Day? What is your mood? You've been married for what, 20 years?

[A]

I've been married for 22 years.

[B]

See? Exactly. So give me advice. Tell me what I need to do.

[A]

I'm going to tell you the advice that I should give my younger self. And it's related to birthdays and Valentine's Day. And I think you already do it a little bit. I used to buy gifts. Okay. I'm going to buy my wife a necklace or something. And then I would buy it and I'd say, here you go. And she goes, not really. Don't love that. And I'm like, oh, crap, I don't even know the return policy. I'm like an idiot. So now I've come to this place in the last few years, which is great, where I don't. We shop together. Where I am no longer like, surprising her.

[B]

Exactly.

[A]

You know, because I am clearly very bad at this. So that's my advice is get on that page. It saves you a lot of pain and heartache.

[B]

There's two things I would add to that is one, when your significant other is mentioning something that they want, like document it. Like, have I have a notes in my phone of like things Ari wants. And then I slightly bring it up in conversations way before, like, oh, like, oh, that looks nice. Like. And like, see her reaction. That's, that's one. One thing is like document. And second, we like some of the major like, like, like store brands out there. I have to log into her account and I tell her to add things to her wish list on there. So she's always adding wish list. And so I always. I was like, add things to your wish list so I know what you like so I can get things for you.

[A]

That's. That's huge. I'm gonna give you login to, like, my Amazon account. I'll add things in there so you can get it for me. That's my new.

[B]

Oh, yeah, I'm gonna start doing that. Salad with salmon is gonna be sent to your office every. Every, every week.

[A]

I can't wait. It's amazing. Well, all right, everybody. Now you're prepared for Valentine's Day.

[B]

We've really.

[A]

We've really crushed this. Appreciate you all being here. Leave Daniel a review on the Market Millennials or leave me one on. Do this, not that. You all are awesome. See you 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 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 shout on LinkedIn and tell us what you want to hear. Peace out.

[A]

Later.