📌 Pinned Comments Are BACK and Your Old Posts Just Got a Second Shot at Getting Seen | Ep. 5

Somewhere between a perfectly timed accidental auto-reply and a restaurant exit nobody wants to relive, there’s real strategy hiding in this one. Jay Schwedelson and Daniel Murray make the case that AI agents are about to change how emails get opened, and that the automation tools everyone trusts can turn on you without warning. Quick, a little gross, and more useful than it has any right to be.ㅤBest Moments:(00:21) An auto-DM answers a listicles joke with “Boom, check your inbox,” and Jay refuses to delete it(01:16) Overlooked holidays in the subject line can lift open rates over 20%(02:05) Why smaller holidays mean far less ad spend to fight through(04:19) Why the subject line could lose its power to AI summaries within a year(04:59) A popular automation tool gets Jay blocked, and the native fix that got him back in(07:07) A family dinner ends with a projectile vomit trail out the front door

Marketers keep finding out that the platforms they depend on change the rules without telling anyone. Jay Schwedelson pushes back hard on Daniel Murray’s view that impressions don’t matter as long as the right people engage. The two end up agreeing on where email is heading now that AI assistants are sorting inboxes. Plus, a small existential crisis about every millennial now being over 30.ㅤBest Moments:(01:01) Is bottle service an instant tool move at any age?(02:58) Jay stopped liking his own posts from company pages, and reach went up(06:09) Why Instagram may be a much easier growth play than YouTube(06:49) How brands can tease a launch and keep viewers on-platform for the full reveal(07:49) The first 200 characters of live text are email’s new North Star(08:50) Image-heavy emails are invisible to AI summaries

Somewhere between a Halloween costume debate and a truly shaky grasp of Harry Potter, Jay Schwedelson and Daniel Murray land some seriously useful marketing advice. The thread running through it all is money: your buyers are watching every dollar, and you’re probably being pitched AI fixes that can’t prove they work. It’s fast, funny, and worth it for the reality check alone.ㅤBest Moments:(03:29) Why “this costs as much as two lattes” can outsell a straight 20% off(04:26) How to pitch your product as a must-buy wishlist item, or a 2027 budget line for B2B(06:46) Why your pinned comment should keep changing long after the post goes live(08:59) What an Ahrefs study on schema markup says about paid AI visibility promises(10:37) The incognito browser test to run before trusting anyone’s AI visibility results(12:31) A Masked Singer segment for Marketingland gets pitched, with Ken Jeong as the dream judge

Google is punishing sites that pump out lazy AI content, yet the AI tools themselves still reward cheesy listicles and quietly ignore any page you haven’t touched in a year. Jay Schwedelson calls it the 1995 version of the internet, and Daniel Murray explains why a retargeting text with a real deadline got him to click. Plus a Halloween rant about parents using babies as candy spokespeople, and a skincare mishap that had Instagram genuinely worried.ㅤBest Moments:(02:43) Google’s spam crackdown targets AI content, scraped posts, and spammy backlinks(03:38) Pages that haven’t been updated in a year are two times less likely to get cited by AI(05:35) Listicles beat every other content format in AI results, cheesy or not(06:04) Adding schema to your site code did nothing for AI visibility(06:46) A retargeting offer with a 2:00 PM deadline that really expired, and why that matters(08:09) Retargeting is still one of the cheapest channels if you treat it as its own program

There’s a brand new segment on the show, and it ranks email metrics by how they rate in the toilet world. Daniel Murray puts open rate, click-through rate, and reply rate in front of Jay Schwedelson, and the verdicts aren’t what most marketers would guess. The metric everyone loves to dunk on survives, and the one everyone trusts gets a serious warning label.ㅤBest Moments:(00:46) Why open rate is inflated but still too useful to flush(01:11) The reporting mistake of lumping newsletters, transactional, and promotional sends together(01:29) Jay’s airport stall-scouting strategy and the metric that matches the feeling(02:02) What a single reply tells the inbox about whether your email belongs there(02:23) The invisible link trick that exposes bot clicks in your reports(02:49) Jay almost announces a bathroom break on The Bathroom Break

Handing AI all your data might be the least risky move you make this year, at least according to one very worked-up host.ㅤDaniel Murray and Jay Schwedelson dig into the content that only works this time of year and the AI tools they’d genuinely hate to lose. They also share an in-flight coffee order that has to be heard to be believed.ㅤBest Moments:(00:51) The real reason long voice notes beat every read receipt(02:17) Gated calendar content sees over a 75% lift from October through January(04:04) The four words your subject lines need until the end of January(06:02) Getting one AI tool to write the prompt for another(08:58) An AI agent catches a double NBA League Pass charge without being asked(12:17) Why black coffee drinkers might just be flexing

The Bathroom Break is officially its own show, a Pardon the Interruption-style rapid-fire on what's working in marketing right now, short enough to finish before your legs go numb. Jay Schwedelson and Daniel Murray can't agree on where emojis belong, but they do agree that posting whatever an algorithm tells you might be the fastest way to look like everyone else. And yes, there's a two-second grocery store shot that somehow took eight takes.ㅤBest Moments:(02:35) Why odd numbers like 7 and 5 beat round numbers at the front of a subject line(03:33) The all-caps first word trick that works for B2B and B2C without hitting junk(03:53) Leading emojis create an accessibility problem, so here's where to move them(04:37) LinkedIn collaborative posts let one post land in up to five feeds at once(07:52) Use Instagram trial reels to test ideas on non-followers before your main feed(08:56) The spaghetti aisle was chosen very carefully, and the reason is hilarious