Podcast Summary: The Marketing Millennials

Episode: Bathroom Break #93 – "How to Make Automated Marketing Feel Human"

Host: Daniel Murray
Guest Co-host: Jay Schwedelson
Date: February 2, 2026

Main Theme

In this Bathroom Break mini-episode, Daniel Murray and Jay Schwedelson dive into a central challenge in modern marketing: how to make automated marketing feel human and engaging. Through lively banter and practical stories, they discuss actionable tips to upgrade your automation game, share personal insights from their own communities, and offer some playful (and surprisingly sharp) advice for marketers looking to inject some personality into their workflows. The tone is candid, fun, and full of immediately usable nuggets, true to the promise of The Marketing Millennials.

Key Discussion Points & Insights

1. Personalization in Automation

• Make Automations Feel Personal:
  Daniel describes how he personalizes DM automations in his community to prompt real replies.

  “I have this DM automation…I saw your name pop up and wanted to reach out…I'm currently enjoying the weather in whatever area, where are you right now?”
  He notes that many community members respond, either believing it’s genuine or at least appreciating the effort.
  “Oh, I know this is automation, but this is really good automation.” (Daniel, 02:37)

• Add Personality & Multimedia:
  Use fun elements like GIFs or memes to reduce the ‘robotic’ feel—such as Daniel including a Yoda GIF in his welcome email, or playful images in text automations.

  “Do little things—like text messages, now you can add GIFs…make it more personal, more fun, more relevant to your audience.” (Daniel, 03:40)

2. Break the Pattern to Stand Out

• Timing & Triggers:
  Jay cautions against ‘set it and forget it’ scheduling, arguing that predictable timings flatten response rates.

  “What you don’t want to do is…everything goes out at 9am or 6am or 11am. That’s a fail…Have automations go at 8:07pm at night. Do things that are counter to what everyone else is doing.” (Jay, 06:42)

• Human ‘Over-the-Top’ Touches:
  Jay says layering a one-off, human-written message over an existing automation stream can ‘wake people up’. The response rate is often much higher than pure automated flows.

  “We looked at those scenarios…and the ones with over-the-top would do phenomenal. People are like, whoa, what's this?” (Jay, 03:55)

3. Omnichannel & Data-Driven Automation

• Retargeting & Segmenting:
  Don’t stop advertising to people once they’re in your funnel—keep educating with targeted ads and create exclusion lists for nuanced campaign delivery.

  “When they do come in your funnel…have an automation to funnel that as an audience…run educational stuff so you stay top of mind…create an exclusion list too.” (Daniel, 05:02)

• Data Enrichment for Personalization:
  Use tools to enhance the data you have and segment your outreach by how much you know about each lead.

  “Having an enrichment automation…so you can start getting more personalized data…have an email for unenriched versus enriched people.” (Daniel, 05:55)

• Platform-Specific Approaches:
  With AI-powered tools, you can tailor the medium—text, email, or social—to meet the habits of your audience for even more timely communication.

  “There’s tools out there that can have automations be more timely and more platform-based...if people are more a text message audience versus email versus social, you can more timely hit those people…” (Daniel, 07:43)

4. Social Posting & Real-Time Interaction

• Don’t Automate and Abandon:
  Jay emphasizes that automating social posts only works if you show up to interact when they go live—the “set and walk away” method leads to dead posts.

  “If you’re automating all your social posts…and you’re not taking the time when they post to actually interact…those posts are going to be dead on arrival.” (Jay, 06:42)

Notable Quotes & Memorable Moments

On Automation’s Human Side

“The more that you can make your automations not feel automated, the more people interact with them and you actually get business.”
(Jay, 03:55)

On Out-of-the-Box Timing

“Have automations do things that are so counter to what everything else is…that’s how your automation is not going to feel like an automation.”
(Jay, 06:42)

On Relationship Management (and Personal Life Advice)

“When your significant other is mentioning something that they want, document it…have notes in my phone of things Ari wants…and then slightly bring it up in conversation way before.”
(Daniel, 09:28)

Timestamps for Important Segments

• [02:37] – Daniel’s “personalized” DM automation technique
• [03:55] – Jay on layering manual emails over automated workflows
• [05:02] – Daniel on retargeting and data enrichment
• [06:42] – Jay on automation timing and live post engagement
• [07:43] – Daniel on AI and platform-tailored automation
• [09:28] – Daniel’s personal tip for Valentine’s Day—document your partner’s wishes

Episode Flow & Tone

• Conversational, light-hearted, filled with real stories and quick-wins
• Practical tips delivered with playful banter
• Occasional digressions into personal life (Valentine’s Day advice), always brought back to actionable marketing guidance

Summary

Daniel and Jay remind marketers that automation should not equal “robotic” or impersonal. From quirky DM intros to clever send times, using enriched data, and layering manual touches, the key is a blend of systematic efficiency with thoughtful, human elements. Add multimedia, embrace varied timing, and always be ready to offer extra value—even in your “automated” content.

“Treat automations like they’re not automations.” (Jay, 06:42)

This episode is a fast, idea-rich bathroom break for marketers ready to rethink their workflows and stand out simply by being more human—even when the machines are doing the heavy lifting.