What’s Up THIS WEEK: Email Fails, Taylor Swift Wedding News? Email TIP! 🎁 What's Up This Week | Ep. 461

Holiday gift snooping, F-bomb subject lines, and an AI country hit somehow all end up in the same conversation, and Jay Schwedelson has opinions. From Lowe's genius decoy gift boxes to a wildly misjudged suit sale email to a simple subject line trick that quietly spikes opens, this week is part marketing therapy, part pop culture catch-up. If you've ever wondered where the line is between clever and cringe, or how targeted your targeting should really be, this one will get you rethinking your next send.

Best Moments:

(00:20) Lowe's leans into holiday chaos with free decoy boxes so parents can hide gifts in plain sight from snooping kids.

(01:25) A suit brand fires off a Black Friday email with a "grow the f**k up and buy a suit" subject line that explodes into a full-blown PR apology tour.

(03:02) Double personalization in subject lines like "pet parents of anxious dogs" or "mid-market CMOs Q1 pipeline fix" quietly crushes with big open rate lifts and way better qualified clicks.

(04:18) Jay breaks down why narrowing your audience with ultra-specific segments may lower volume but massively upgrade intent and sales potential.

(06:05) An AI-generated country song hits number one on the Billboard charts, and Jay questions whether machine-made music should even be allowed on human charts.

(05:12) Streaming recs get personal as Jay walks back his early take on Netflix's The Beast in Me and admits he still cannot bring himself to care about Stranger Things or the Taylor and Travis wedding frenzy.

Partner with Jay! https://www.jayschwedelson.com/contact

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Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out June 9, 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

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