In short
Podcast Episode Notes: Do This, NOT That: Marketing Tips with Jay Schwedelson
Episode Overview
- Title: SPECIAL SERIES ==> Stop Sending Emails at 9 AM 🛑 <== | BATHROOM Break #93 COLLAB: The Marketing Millennials + Do This, Not That
- Description: In this episode, Jay Schwedelson collaborates with Daniel Murray to discuss effective email automation strategies, emphasizing personalization and timing to enhance engagement. They also touch on relationship tips in time for Valentine's Day.
Key Themes and Concepts
Automation in Marketing
- Personalization:
- Importance of making automated messages feel personal.
- Example: Use of conversational tone and relatable context in automated messages (e.g., mentioning the weather).
- Incorporation of multimedia elements (GIFs, memes) to enhance engagement in welcome emails.
- Over the Top Automation Strategy:
- Combining automated emails with personalized, one-off emails to add a human touch.
- This approach can significantly increase response rates and engagement.
- Avoiding Generic Timings:
- Sending emails at odd hours (e.g., 8:07 PM) to stand out, rather than the standard 9 AM or 11 AM slots.
- This strategy prevents emails from blending in with typical daily communications.
Marketing Techniques Discussed
- Engagement Strategies:
- Automations must not be a "set it and forget it" task; continuous interaction is vital.
- Encouragement to engage with social media posts shortly after automation to drive more interaction.
- Audience Segmentation:
- Utilizing automation to create audience segments for targeted advertising.
- Keeping subscribers engaged through tailored educational content.
- Data Enrichment:
- Using tools to gather more information on contacts to improve personalization.
- Differentiating communication strategies based on enriched vs. unenriched data.
Relationship Advice for Valentine's Day
- Valentine's Day Planning:
- Discussion on the importance of being thoughtful and proactive in planning for Valentine’s Day.
- Suggestions include shopping together or documenting gift ideas based on previous conversations.
- Communication:
- Advice on documenting desires and preferences of significant others to ensure thoughtful gifts.
- Use of wish lists on retail platforms for easier gift selection.
Best Moments
- (01:52) Valentine's Day Planning: Celebrating early can avoid high costs and crowded venues.
- (02:37) Automated DMs: Crafting personalized automated messages that elicit genuine responses.
- (03:30) Using Multimedia: Making welcome emails interactive and engaging with GIFs.
- (04:29) "Over the Top" Strategy: Injecting personal emails into automated sequences for increased engagement.
- (06:45) Email Timing: Avoiding standard email sending times to increase open rates.
Closing Remarks
- Jay emphasizes the need for marketers to treat automations as dynamic and engaging rather than static processes.
- Daniel adds that both marketing and relationship advice can enrich both personal and professional interactions.
- Call to Action: Listeners are encouraged to leave reviews and engage with the hosts on LinkedIn.
Additional Resources
- Check out Jay’s [YouTube Channel](https://www.youtube.com/@schwedelson)
- Follow Jay on [Instagram](https://www.instagram.com/jayschwedelson/)
- Pre-order Jay's upcoming book, *Stupider People Have Done It* [here](https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206).
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These notes capture the essential insights and discussions from the podcast episode, providing a structured overview for marketers and listeners interested in enhancing their automation strategies and personal connections.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOValentine's Day Planning
0:46 to 1:49
Discussion on how to plan for Valentine's Day with humor and personal anecdotes.
“But what is exciting, I'm curious, is not too far away is Valentine's Day.”
Personalizing Automations
1:50 to 4:12
Tips on making marketing automations feel personal and engaging.
“or something so you don't get these prefixed annoying menus that they have that are overpriced.”
Effective Email Strategies
4:13 to 7:40
Insights on how to make email marketing more effective and less predictable.
“you know, direct-to-consumer play, whatever, that they have the automation streams already all set up.”
Gift-Giving Advice
7:41 to 10:12
Sharing personal experiences and advice on how to choose meaningful gifts.
“And there's like tools out there that can have automations be more timely and more platform-based.”
Transcript
Automatic transcript. May contain errors.0:07Welcome 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. We are back for the bathroom break.
0:41I'm here with Daniel Murray, the marketing millennial. I'm Jay Schwedelson from Do This, Not That. And before we get it, 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 that know this about Daniel, extremely romantic guy. He's like Cyrano de Bergec. He writes poems and sings these songs to Ari. It's unbelievable. So Daniel, I know you must plan months in advance. So do you really plan seriously for Valentine's Day as it's approaching? I believe, like, that's what she's going to say, but, like, I think you should do, like, what you do on Valentine's Day, like, tons during the year anyway for your significant other.
1:22So I think there's the romantic of me, but I do, I do think that it's like a carved out date. So I like to like plan a dinner, get a little gift. This year I want to do like a gift from our son to her. So like, like something cute like that. So yeah, I do think that I, but I also do think like sometimes it's better to like celebrate it the day before or something so you don't get these prefixed annoying menus that they have that are overpriced. So that's an option as well. There you go. I love it. I love it. Well, there you go. You got the Valentine's advice from Daniel. So let's jump into it, though, about what we're talking about, automations.
2:11There's a lot of things out there that we all automate, whether you're a business market or a consumer market or whatever, nonprofit. You're automating people going to a landing page, filling out a form, an email goes out. You're automating certain social posts that 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? I think one thing is make your automations feel personal and you could do it in a generic way.
2:46So for example, i have this like dm automation in my community that i go say like i saw you scrolling and and i saw your name pop up and and i wanted to reach out and say like how like how are you doing blah blah and i say like i'm currently like enjoying the weather in whatever area where are you right now and i get like tons of replies like either like you're so lucky you're in warm weather or like oh i know this is automation but it's this is really good automation so like when you're doing automation always make it feel personal fun uh part of your brand i think another layer to add on is adding gifts or um multimedia stuff and to to make it feel like more fun so like in my welcome email, I have like a Yoda meme, like I'm in Yoda gif.
3:44So 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. 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.
4:21But 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? Wakes them up a little bit.
4:53So 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. 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 do come in your funnel, having that as a list in whatever tool you're using to collect emails and have an automation to funnel that as an audience to run educational stuff so you stay top of mind because now you've got them in one point of your funnel.
5:34Now 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 like 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 like 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 like a, a tool that can like get more information about, uh, enrich that data.
6:21So 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. Yeah, I love all of that. And there are also some simple things that you could do with your automations that I think people miss on. So, for example, if you're doing email automations, you've got all these different triggers based on what they did or haven't done or fallen off or this, that, or whatever.
6:54What you don't want to do is like, all right, all of our stuff is going to go out at 9 a.m. or 6 a.m. or 11 a.m. 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 8.07 p.m. 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, your company just automated, those posts are going to be dead on arrival.
7:40So treat automations like they're not automations. 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 i love that so all right back to the valentine's day thing Do you write poems?
8:32No, but I feel like you're a poem guy. What do you do about that? What is your move? You've been married for, what, 20 years now? I've been married for 22 years. See, exactly. So give me advice. Tell me what I need to do. 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's like, not really, don't love that. And I'm like, oh, crap. I don't even know the return policy.
9:07I'm like an idiot. So now I've come to this place in the last few years, which is great, where we shop together, where I am no longer surprising her. Exactly. 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. 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 I have notes in my phone of like things Ari wants. And then I slyly bring it up in conversations way before like, oh, like, oh, that looks nice. Like, and like see her reaction. And that's, that's one, one thing is like document.
9:52And second, some of the major 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 lists. 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. That's huge. I'm going to give you a login to my Amazon account. I'll add things in there so you can get it for me. That's my new choice. Oh, yeah. I'm going to start doing that. But salad with salmon is going to be sent to your office every day. I can't wait. This is amazing. Well, all right, everybody, now you're prepared for Valentine's Day.
10:29We'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 got to get back to work. Get out of there. 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 back from my bathroom break this is daniel go follow the mark and mille podcast but also tune into this series it's once a week the bathroom break we talk about marking tips that we just spew out and it could be anything from email subject line to any marketing tips in the world.
11:13We'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
Most marketers treat automation like a "set it and forget it" task, but that is exactly how you end up with low engagement and ignored emails. Jay Schwedelson connects with Daniel Murray to break down why the best automated sequences do not look automated at all. They also detour into some surprisingly practical relationship advice just in time for Valentine's Day.
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Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.
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Best Moments:
(01:52) Why celebrating Valentine's Day a day early might actually be the smarter move
(02:37) How to write automated DMs that actually get replies instead of eye rolls
(03:30) Using GIFs and multimedia to make welcome emails feel less robotic
(04:29) The "Over the Top" strategy of inserting manual emails into automated streams
(06:45) Why sending emails at standard times like 9:00 AM is a guaranteed way to be ignored
(07:15) The power of sending automations at odd hours like 8:07 PM to boost open rates
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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson
Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson
Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/
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Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out April 21, 2026). All net proceeds are donated to The V Foundation for Cancer Research—let’s kick cancer’s butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206




