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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

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Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Connect with Alexandra Conners on LinkedIn, and see what her team is building at wunderkind.co.

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Every martech platform seems to be buying up every other one right now, each promising to become the single tool that finally does everything. Jay Schwedelson gets Alex Conners of Wunderkind to pressure-test that idea, and her take is refreshingly blunt: the all-in-one promise is mostly a mirage, and your real edge was never sitting in the stack to begin with. What she says is actually driving results now might change how you look at your next renewal.

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Best Moments:

(02:20) Most brands use only about 30 percent of what their marketing tools can actually do

(03:46) Why a platform's new acquisition is really just negotiation leverage with your CFO

(06:04) The right martech pick has less to do with your industry than your team's skill set

(07:17) Customer acquisition costs jumped 222 percent and the buying journey keeps getting longer

(10:30) The average enterprise is quietly running 91 marketing tools, and the risk that creates

(12:05) A plain-English breakdown of what Wunderkind actually does with your anonymous site visitors

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Turns out one of the email "best practices" you have probably been told to follow for years might be quietly working against your list. Recording from the road this week, Jay Schwedelson makes the case that confirmed opt-in is more than halfway to dead, and that the spam-complaint logic everyone repeats about it is actually backward. If you have ever asked a new subscriber to click a confirmation link, this one is worth a few minutes.

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Best Moments:

(00:33) LinkedIn rolled out free in-network versus out-of-network reach data on every post, no premium account required

(02:00) Confirmed opt-in is fading fast, with usage down more than 45 percent year over year

(03:33) The myth gets busted: lists built on double opt-in actually draw higher spam complaints, not fewer

(04:15) Reddit just added video replies, opening a fresh way to reach its billion-plus monthly users

(05:00) Jay's new book "Stupider People Have Done It" is out, with all author proceeds going to cancer research

Most teams roll out the VIP treatment for anyone who already swiped a card, then quietly ignore the people circling the website five times in a week. Jay Schwedelson and Daniel Murray make the case that your loudest buying signals are sitting in segments you probably never bothered to build, hiding in plain sight while you fuss over the folks who already converted. There is also a detour into bikini-store career advice and the structural horrors of the Rhode Island accent, so adjust your expectations accordingly.

ㅤ

Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.

ㅤ

Best Moments:

(02:00) The VIP segments already sitting in your database that you keep sleeping on

(02:40) Why pain-point segmentation beats another round of lead scoring

(03:19) The argument for in-person events being the strongest intent signal you have

(04:00) Five site visits or eight email clicks is nobody's accident

(05:27) Lifetime value of audience deserves as much love as lifetime value of customers

(06:37) How brands quietly torch loyalty by only reaching out at renewal time

(07:15) The dedicated send you owe subscribers who have stuck around five years

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Most of us figure we've already tried every subject line trick worth trying, which is exactly what makes this batch so annoying. Jay Schwedelson runs through a pile of tactics that sound too dumb to work, like dropping a period after every word or dressing up a subject line as a calendar invite, except the open rates keep climbing anyway. Stick around for the strangely strong hill he's willing to die on involving coworkers, swimming pools, and dance floors.

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Best Moments:

(01:20) Why a subject line that reads like a calendar invite is lifting opens by 28%.

(02:15) The bracketed newsletter trick everyone abandoned, back from the dead and working again.

(03:43) Opening a subject line with And or But to trigger a different kind of curiosity.

(04:15) A period. After. Every. Word. And the quiet drama it stirs up.

(04:46) Dropping next month into your subject line two weeks early, and why people bite.

(06:00) Jay's deeply held refusal to see work people in bathing suits or on a dance floor.

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Ever asked an AI tool to explain your own company and cringed at how wrong it got things? This week there's a genuinely simple fix for that, and Jay Schwedelson lays it out in a way that turns those AI answers into a ready-made content plan. He somehow gets there by way of a hospital collab and a four-dollar Instagram upgrade he's weirdly excited about, which tells you everything about how this one flows.

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Best Moments:

(00:16) Disney teams up with Philips to surround kids with ambient Disney characters during their MRIs

(01:36) The gut-punch stat, 88 percent of CMOs are getting grilled on AI visibility while most have no plan

(02:06) Most marketers have already caught AI describing their company completely wrong

(03:40) Ask all four AI tools the same question, then build content around the answers they all share

(04:52) Meta's new Instagram add-on lets your stories outlive the 24-hour cutoff, and Jay thinks it's worth it

(06:45) The Eventastic pitch arrives with DJs, a cannonball guy, and a Taylor Swift dance contest

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Ever caught yourself snapping at ChatGPT when it just won't get something right? Jay Schwedelson and Daniel Murray get into exactly how (un)kind they are to their AI tools, then swing into the small webinar habits quietly tanking everyone's show-up rates. It's equal parts petty and practical, and the live-only advice alone earns the ten minutes.

ㅤ

Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.

ㅤ

Best Moments:

(01:53) Jay confesses he's relentlessly rude to AI and explains why yelling never actually helps

(02:47) The hidden environmental cost of being polite to ChatGPT

(03:48) The webinar title mistake that kills curiosity before anyone signs up

(06:51) Why a serialized, same-time webinar turns it into a show people come back to

(07:16) Two day-of reminder emails and the 400% jump that comes from live attendanceㅤ

(09:06) Holding on-demand hostage for 30 days to force people to show up live

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Connect with Kristen on LinkedIn and visit ringcentral.com to see what they're building with AI across voice, video, and messaging.

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Most marketers are using AI to shout louder. Kristen Koenig, who leads AI and Collaboration go-to-market at RingCentral, thinks the smarter move is using it to listen better. She's back with Jay Schwedelson to unpack what most marketers are getting wrong about AI, why voice is having a renaissance, and what meetings will actually feel like three years from now.

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Best Moments:

(01:46) Why right now is a renaissance moment for marketers and communicators

(02:39) The fix for AI that sounds like a robot starts with feeding it your real voice

(04:35) The biggest thing most marketers are getting wrong with AI

(06:49) More content, worse quality, and why chasing volume is a trap

(11:43) Why companies are so AI-obsessed, they're forgetting to improve the actual mothership product

(13:39) What voice and video will actually feel like in the next three years

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Ever wonder why your slick, AI-polished marketing content gets crickets while someone's shaky phone clip from a hallway racks up engagement? Jay Schwedelson breaks down the lo-fi content formats actually winning right now, with hard numbers on why behind-the-scenes videos, walking selfies, and even airport rants outperform the polished stuff. Stick around for the chaos of prepping Eventastic, which somehow involves a Taylor Swift impersonator, a mouth guard game, and a guy being shot out of a cannon.

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Best Moments:

(00:16) Why expensive, AI-perfect marketing now reads as more boring than wallpaper

(01:30) Behind-the-scenes video drives 200% higher engagement on LinkedIn than any other format

(02:45) The red play button trick that lifts email click-through rates by 34%

(03:30) Walking selfies pull 49% higher completion on LinkedIn and 57% on Instagram

(04:14) Desk drive-bys and one-take mistake clips that beat any polished asset

(05:15) Why airport walk-and-talks turn boring B2B content into something humans actually watch

(06:30) The behind-the-scenes panic of dry-running the Fate of Ophelia dance for Eventastic

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

MASSIVE thank you to our Sponsor, CallRail!

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Meta just quietly dropped a standalone app built to swipe users straight from Reddit, and that's only the start of what Jay Schwedelson is digging into this week. There's also a new LinkedIn tool that exposes which AI models people are actually using by industry, plus some fresh data showing that one tiny tweak to your promotional emails can triple engagement and seriously boost your inbox placement.

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Best Moments:

(00:16) Meta launches Forum, a standalone app built to go straight at Reddit

(01:36) LinkedIn Cross Check reveals which AI models are dominating by industry

(03:30) Why reply-driven promotional emails are pulling 3X the engagement

(04:25) The 90-day inbox placement lift B2B brands are seeing from reply CTAs

(05:18) Reply rate is now the number one signal for Outlook, Gmail, and Yahoo

(06:30) Love Island USA returns June 2nd with ad demand up 73% year over year

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

ㅤ

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!

ㅤ

Memorial Day weekend brings up the eternal marketer's debate: do you keep the emails flowing or pump the brakes for the holiday? Jay Schwedelson and Daniel Murray make a strong case for sticking with consistency, plus share a surprisingly clever trick for turning all those out-of-office auto replies into retargeting fuel. Stick around for a housewarming gift confession that'll either make you laugh or quietly question your own friendships.

ㅤ

Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.

ㅤ

Best Moments:

(01:46) The Irish goodbye strategy for surviving networking events you didn't want to attend

(02:49) Why breaking consistency for a holiday is a bigger mistake than the lost opens

(03:47) Turning out-of-office auto replies into a retargeting goldmine with one AI tool

(05:38) The subject line trick for speaking to the exact moment your audience is living in

(08:34) How LinkedIn's new 24 to 48 hour algorithm window is changing what a "flop post" looks like

(10:37) The unopened housewarming gift sitting on a counter for six months that says everything about adult friendships

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

ㅤ

Connect with Laura Morton on LinkedIn and explore Lasega Books at lasegabooks.com to learn about her hybrid publishing imprint.

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Imagine writing your first book, hitting a wall, and then learning the person guiding you through it has 23 New York Times bestsellers on her shelf and 60-plus titles with names like Justin Bieber, the Jonas Brothers, and Al Roker.

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That's the call Jay Schwedelson made when he started writing Stupider People Have Done It, and the person he kept hearing about was Laura Morton.

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She's the publisher behind his book, the founder of Lasega Books, and she joins to pull back the curtain on what really sells, what AI can't fake, and why pre-orders quietly decide everything.

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Best Moments:

(02:45) Four million books were published last year, and the average one sells just 300 copies

(06:00) The three boxes a book has to check before Laura agrees to publish it

(07:05) Why even billionaire founders walk in feeling like total impostors

(09:38) How Laura spots an AI-written manuscript in under a minute

(14:30) The word "intimacy" broken down into "into me you see," and why that's what readers really come for

(17:00) The real reason pre-orders matter more than the launch week itself

(22:15) Writing the book is only ten percent of the work, the other ninety is what most authors miss

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

ㅤ

Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

ㅤ

Register for Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

ㅤ

Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com

ㅤ

Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

ㅤ

Leave a comment and follow the show, it really helps us out!