Podcast Summary: Do This, NOT That: Marketing Tips with Jay Schwedelson

Episode: What’s Up THIS WEEK: Email Fails, Taylor Swift Wedding News? Email TIP! 🎁 What's Up This Week | Ep. 461
Date: December 9, 2025
Host: Guru Media Hub

Episode Overview

This episode delivers Jay Schwedelson’s signature blend of quick marketing insights, practical email marketing tips, and a dash of pop culture analysis. The host dives into inventive holiday marketing tactics, a cautionary email marketing fail, cutting-edge email personalization strategies, and weighs in on trending pop culture—from Netflix picks to the surprise of an AI-generated country hit topping the charts.

Key Discussion Points & Insights

1. Creative Holiday Marketing from Lowe’s

[00:16–01:45]

• Snooping and Gift Discoveries: Jay opens with an amusing anecdote about holiday gift snooping, referencing a Lowe’s survey that found 57% of kids found or opened their presents early.

• Lowe’s Loyalty Campaign: Lowe’s responded by creating “giant boxes” for their loyalty members that feature misleading labels (e.g., “coffee maker”) to stash real presents, keeping gifts hidden from curious family members.

  • Insight: Tying quirky consumer behaviors into branded solutions can boost loyalty and engagement.
  • Quote:
    “So what they did … they made these giant boxes for loyalty members only … and you shove your presents in these boxes so nobody wants to open those.” (01:00)

• Gen Alpha Gift Obsession: The survey hilariously reported that kids ask about holiday presents an average of 51 times per season.

2. Email Marketing Fail: When Edgy Goes Wrong

[01:45–03:08]

• Suit Company Blunder:
  Jay recounts a notorious email subject line used by a suit company striving for an “edgy” Black Friday campaign:
  “Grow the f--k up and buy a suit.”
• Public Fallout:
  The email went viral for the wrong reasons, with backlash reaching the New York Post and resulting in a company-wide apology from the CEO by that evening.
• Lesson:
  Edgy humor and strong language in subject lines often backfire and can alienate rather than attract.
  • Quote:
    “Why don’t we put the F word in our subject line and insult everybody? Because that’s gonna get people to want to buy a suit. What is wrong with people?” (02:46)

3. Actionable Email Tip: Double Personalization in Subject Lines

[03:08–04:34]

• What is “Double Personalization?”
  Jay introduces “double personalization”—combining two relevant attributes in the subject line to target recipients more specifically (e.g., “Pet parents of anxious dogs,” “Mid-market CMOs Q1 pipeline fix”).
• Examples:
  • “Home cooks who meal prep”
  • “Beauty fans with sensitive skin”
  • “Finance teams at high growth startups”
• Proven Results:
  • Consumer open rates ↑ 29%
  • B2B open rates ↑ 24%
• Strategic Advantage:
  More granular targeting leads not only to higher open rates but also to more qualified, conversion-ready leads.
  • Quote:
    “The sooner you tell somebody who they are, the faster they want to engage. … With double personalization, [the recipient thinks] wow, this is really for me.” (04:08)
  • Pro Tip:
    Even if click-through rates are lower overall, those who do engage are highly relevant prospects.

4. Pop Culture Check-in

[04:34–06:48]

a. Netflix & TV Picks

• Jay revisits his review of The Beast in Me (Netflix, Claire Danes), confessing he’s changed his mind after bailing early and receiving flak.
  • Quote:
    “I need to undo what I said. I was wrong … It’s very good. The Beast in Me is very good with Claire Danes.” (05:20)
• Admits he has yet to get into Stranger Things.

b. Taylor Swift & Travis Kelce’s Rumored Wedding

• Acknowledges swirling rumors (wedding date set for June 13, 2026, in Rhode Island), but is unimpressed.
  • Quote:
    “Do I care about this yet? No, I don’t. Hit me up June 12th. We’ll see what’s going on.” (05:53)

c. Music Industry Shake-Up: AI Hits #1

• AI Song Topping Country Charts:
  • “Walk My Walk” by Breaking Rust, an AI-generated artist, hit #1 on the Billboard US Country Singles Chart.
  • Jay questions the fairness and future of AI music on traditional charts.
    • Quote:
      “This was not made by a human … I think we gotta do something. … I don’t think we should allow AI generated songs to be factored in to the charts.” (06:23)
    • Concern:
      AI music can “take jobs away from people.”

Notable Quotes & Memorable Moments

• “If you are [a holiday gift snooper], you stink.” (00:20)
• “[The suit company’s email] blew up sideways. The New York Post picked it up. … What is the meeting that goes on there?” (02:09)
• “This idea is great … Double personalization … you may get a lower open rate, lower click-through rate by doing this, but anybody that reacts … is so much further down the funnel.” (04:27)
• “I hope you’re having a great start to the holiday time of year. … I kind of grind right until about the 20th. That’s really when I try to push as hard as I can.” (07:00)

Timestamps for Key Segments

• 00:16–01:45 — Lowe’s clever holiday marketing (survey & loyalty campaign)
• 01:45–03:08 — Email marketing fail: suit company’s offensive subject line
• 03:08–04:34 — Email tip: Double personalization in subject lines (with stats & examples)
• 04:34–05:53 — Streaming TV: “The Beast in Me” & “Stranger Things” talk
• 05:53–06:23 — Taylor Swift & Travis Kelce’s wedding rumors
• 06:23–06:48 — Billboard charts: AI-generated country song controversy

Tone & Style

Jay maintains a witty, conversational, and slightly irreverent tone—mixing genuine marketing advice with personal anecdotes and cultural commentary. The guidance is practical and up-to-date, balanced by humor and the occasional (self-)roast.

Takeaways

• Creative campaign ideas (see Lowe’s) can earn goodwill and engagement if they tap into real behaviors.
• “Edgy” does not always equal effective: push the boundaries with caution, especially in public-facing marketing collateral.
• Leveraging double personalization in email subject lines can substantially increase open and conversion rates.
• The rise of AI-generated content is becoming a major disruptor—especially for music and entertainment.
• Showing flexibility and admitting when you’re wrong (as with TV recommendations) builds credibility and connection with your audience.

For listeners (and marketers) who want sharp, actionable ideas with a dash of culture: this episode delivers value, laughs, and plenty of “don’ts” to save you from your next campaign blunder.