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.

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.

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)

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.

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.

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.

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.”

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.

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)

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)

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.

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.