Subject lines that tap into who your audience wants to be, a bathroom emergency at a Nashville hot chicken spot, and a minus-200 degree cryotherapy experiment all show up in this Ask Us Anything with Jay Schwedelson. Jay riffs on a listener's challenge to share a subject line test they probably have not tried yet, breaking down the idea of aspirational personalization that speaks a level above your current audience. Then he answers a not-so-serious question about his health that turns into a ridiculous story involving Boca Raton, Brass Monkey, and a frosty recovery chamber.

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Best Moments:

(00:16) Jay explains the Ask Us Anything format and how to send him your own work and ridiculous questions through his site.

(01:15) Hattie B's "shut the cluck up" hot chicken story ends with a bathroom line so long he swears they need 74 restrooms.

(02:15) Jamie's challenge for a subject line test they have never tried sets Jay up to go beyond basic personalization.

(03:38) Jay introduces aspirational subject lines that speak to the C level or lifestyle people want instead of the role they have now.

(05:30) He shares data from 50 million sends showing aspirational subject lines lifting open rates by roughly 24-28 percent in both B2B and consumer campaigns.

(06:30) Bill's jab about Jay's health leads to a cryotherapy adventure in Boca Raton, complete with Brass Monkey and dancing in a minus-200 degree box.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

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.

Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

December might feel slow for B2B, but Jay Schwedelson and Daniel Murray are using it to double down on what actually worked in their email programs this year. They trade five real world email lessons headed into 2026 - from reply worthy CTAs and smarter list metrics to domain reports and AI powered repurposing - while calling out the bad hot takes about what does and does not matter in your metrics. You get practical tweaks you can ship immediately, plus a little peek into their real lives as humans who occasionally leave their inboxes.

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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.

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Best Moments:

(03:04) Daniel shares why every email now includes a simple, low lift reply question so he can spark real conversations and keep deliverability strong.

(04:07) Jay explains why the idea of a single "best send time" is garbage and why he tracks weekly unique humans engaging instead.

(05:11) Daniel breaks down his "verified subscriber" metrics to see how true ICP subscribers are opening, clicking, and shaping future email content.

(06:07) Jay walks through running a domain frequency report to spot deliverability bottlenecks and hidden account opportunities inside your list.

(07:21) Daniel shows how to repurpose talks, webinars, and podcasts into tactical emails using AI so you can add sends without adding burnout.

(08:23) Jay and Daniel rant about why open rates and preheaders still matter, how rage bait content confuses marketers, and why cleaning your list is still non negotiable.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

Think your B2B world is doomed to be dry and boring? Kathryn Frankson sits down with Jay Schwedelson to prove the opposite, pulling stories from massive fintech stages, tiny city libraries, and even her own tea obsession to show how human your marketing could be. From last touch attribution myths to three year event strategies that actually leave room for creativity, this conversation is basically a permission slip to stop hiding behind spreadsheets and start telling real stories. If you have ever been told to just “stick to the numbers,” you are going to feel very seen.

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Connect with Kathryn on LinkedIn and explore Money20/20 to see how she brings human first storytelling into massive global fintech events.

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Best Moments:

(01:20) Kathryn shares how years as a quota carrying B2B sales rep shaped her obsession with human centered marketing and real storytelling.

(03:40) Why she loves so called boring B2B industries and hires people with zero events background to keep perspectives fresh and curious.

(07:30) The New Berlin library trust fall video, a renamed Minnesota town, and a car dealership spoof show how wildly creative “unsexy” sectors can be.

(10:05) Kathryn breaks down how Money20/20 uses three year strategy, data, and clear guardrails so creativity and storytelling are baked into the plan, not random one offs.

(12:05) A takedown of last touch attribution and the gap between how humans actually discover brands and how most marketing teams try to measure it.

(15:05) Kathryn sells Jay on switching from coffee to tea with a mini masterclass on polyphenols, calmer energy, and her “I like my marketing hot, but my tea hotter” tagline.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

December might feel like a throwaway month, but Jay Schwedelson is here with a simple shift that turns the end of the year into a lead and revenue spike by using intent signals as your actual offer. He walks through how to spot and capture real buying intent across B2B, consumer, and nonprofit campaigns, then finishes with some very honest (and funny) thoughts on holiday cards and those ridiculous surprise-car commercials. Expect specific copy ideas you can steal right away while everyone else is mentally on vacation.

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Best Moments:

(00:20) Why December is secretly a goldmine if you stop mailing it in and lead with intent-based offers.

(01:45) B2B examples like Q1 readiness audits, vendor comparison checklists, and RFP kickstart kits that instantly reveal who is in market.

(03:05) Consumer plays such as last-minute hero finder and VIP early access for sellout items to target shoppers who are still actively buying.

(04:15) Nonprofit hooks like donation impact calculators and sponsor a need selectors that surface serious year-end donors.

(04:55) How intent signal campaigns in December and early January crush for pipeline, platform switches, and tax-motivated giving.

(05:40) Jay’s rant on random family holiday cards and unrealistic holiday car gift commercials you never see in real life.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

From under-16 social media bans in Australia to the sneaky reason your email should never go out exactly on the hour, this weekly rundown packs in plenty of usable takeaways and a little chaos. Jay Schwedelson connects policy shifts, inbox strategy, influencer math, and the latest AI land grab so you can keep your marketing sharp without living in a news feed. He even throws in some wild traffic stats and a Stranger Things rant that might make you question how old you feel right now.

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Best Moments:

(00:16) Jay riffs on Australia's under 16 social media bans, Snapchat's behavioral signals, and why age gating is about to spread to the EU and US.

(01:57) A dead-simple holiday email trick where not sending on the hour helps you dodge inbox clutter and lift open rates by around 15%.

(03:15) Holiday influencer rate reality check for micro creators and why follower count means nothing without real engagement.

(04:15) Jay makes the case for Team Gemini, breaking down fresh usage numbers and how it is catching up fast to ChatGPT.

(05:09) Wild traffic stats reveal Yahoo and even Bing pulling more visits than ChatGPT, leaving Jay stunned at what people still type into their browsers.

(06:34) From Wicked vs Zootopia 2 box office surprises to the very grown up Stranger Things cast still riding bikes, Jay wonders when nostalgia finally goes too far.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

A quick-hit Bathroom Break with Jay Schwedelson and Daniel Murray that actually makes social feel manageable again — from tiny boost budgets that move mountains to a commenting play that beats mindless posting. You’ll also hear why short video still wins, how to turn email into a social flywheel, and a sneaky Stories tactic Daniel swears by.

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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.

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Best Moments:

(03:00) LinkedIn’s new comment impressions make thoughtful replies a growth channel, not an afterthought.

(04:31) Micro budgets work: toss $5 on YouTube or under $50 on IG/LinkedIn to amplify content that’s already winning.

(05:41) Treat short video like share fuel for DMs, Slack, and group chats with a tight first three seconds and a clean loop.

(07:00) Stop propping up losers and only boost winners, plus link newsletter hero images straight to your social posts.

(08:00) Balance rented and owned audiences so people see you wherever they actually pay attention.

(08:45) Use IG Stories with DM keywords and simple automation to spark replies that lift your story distribution.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

Most people cranking out content feel like they’re on a hamster wheel, and this one is Jay Schwedelson basically turning his own burnout into a live strategy session with Caleb Ralston. They get into why copying 400-post-a-week creators is wrecking your brain, how to reverse engineer a cadence that actually fits your life, and what it really means for a personal brand to “work.” If you care more about leads, trust, and reputation than vanity metrics, this convo will mess with how you think about content in a good way.

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Check out Caleb’s free 6-hour-and-22-minute YouTube course on how to build your personal brand, grab the companion workbook by dropping your email, and use it to level up before you ever think about hiring a media team.

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Best Moments:

(00:16) Jay admits he “got the guy” behind some of the biggest personality-led brands because he wants to reverse engineer what actually works for personal brands.

(03:00) Caleb explains why copying top creators’ insane content routines is like trying to train like the greatest athlete on day one and guarantees you will quit.

(04:15) The low-volume, high-effort strategy that grew Caleb’s YouTube to over 50,000 subscribers from just seven videos by focusing on depth over constant posting.

(08:58) Breaking down the Brand Journey Framework so you finally define why you are building a personal brand and what success is supposed to look like.

(13:23) A behind-the-scenes example of a video designed with one job only: get talented creatives to DM Caleb so he can place them on client media teams.

(16:01) Why views and followers are useful signals but become dangerous distractions when sales, conversions, and cost to acquire a customer are going the wrong way.

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

AI sounds like a shortcut until your “great” ideas flop in the wild, and that is exactly what Jay Schwedelson digs into here. He breaks down a simple 100,000 person prompt that quietly flips AI out of generic creative mode and into deeper statistical thinking, then shares what happened when he A/B tested it on subject lines and CTAs. Plus, a surprisingly relatable question about hating phone calls turns into a legit strategy for staying connected without awkward calls or endless text threads.

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Best Moments:

(01:00) Alyssa from Denver asks why AI generated ideas keep underperforming, and Jay flags the hidden problem with how most of us prompt these tools.

(01:47) Jay introduces the 100,000 person prompt and shows how to ask AI to simulate huge audiences reacting to subject lines, landing pages, and offers.

(03:05) Jay explains how framing prompts around 100,000 real people forces AI out of pure creativity and into deeper statistical mode for sharper recommendations.

(03:45) Jay shares A/B test results where 100,000 person prompts beat generic AI suggestions over 70 percent of the time and even double click throughs on CTA buttons.

(05:15) Jared from Dallas admits he hates phone calls and finds texting shallow, and Jay gets real about how easy it is to drift into isolation.

(06:00) Jay reveals his go to solution of voice memos as a low pressure, high connection way to maintain relationships without live calls or walls of text.

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Prompts mentioned:

• Predict how 100,000 real subscribers would respond to each of these subject lines, rank them by expected open rate, and explain the psychology.
• Evaluate this hero section as if 100,000 new visitors landed on this landing page. Identify confusion points and drop-off risks.
• How would 100,000 consumer buyers or 100,000 B2B buyers interpret this offer? What is confusing, what is strong, and what is missing?
• We want you to simulate 100,000 people interacting with this call-to-action button. What should the language be?

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

Getting ready for Thanksgiving has nothing on the chaos swirling around AI, privacy rules, and even Instagram trying to make you watch 20-minute reels. Before the turkey coma hits, Jay Schwedelson digs into everything from the death of the em dash to Google’s sneaky new flight deal superpower, plus a few very strong opinions on Netflix holiday movies. Somehow it all ties together in a way that’ll make your week a little smarter and a lot funnier.

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Best Moments:

(00:00) ChatGPT finally admits the M dash problem and promises to stop abusing it

(01:41) Europe’s Digital Omnibus plan could loosen GDPR and ease cookie consent madness

(03:28) Instagram quietly tests 20-minute reels, and Jay cannot handle it

(04:00) Google’s AI-powered flight deals tool is officially rolled out and wildly useful

(05:17) Three preheader words that just boosted email open rates by 19 percent

(06:44) Jay’s brutally honest reviews of The Beast in Me and Merry Little Ex Christmas

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

Holiday email engagement is somehow both nerdy and genuinely fun here, as Jay Schwedelson and Daniel Murray use Thanksgiving food opinions, Hallmark movies, and Bathroom-Break banter to get into why replies matter way more than most marketers think. They dig into how to engineer responses in your emails and stories, why reply rate is a killer signal for both humans and algorithms, and how AI plus simple prompts like “Reply GUIDE” can quietly blow up your results. It’s basically a playbook for turning “one-way” campaigns into conversations people actually want to have.

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.

Best Moments:

(00:50) Daniel shares his not-so-traditional Thanksgiving background and why dry turkey is an instant no.

(02:06) Jay’s hard rule for Thanksgiving dinner: mac and cheese is required, salad is banned.

(02:49) Jay explains why the reply rate on promotional emails is about to explode thanks to AI and better follow-up.

(03:28) Daniel’s tricks for prompting real human replies, from light personal questions to hidden Easter eggs in the middle of an email.

(05:20) Jay’s “just reply GUIDE” tactic for content and discounts that crushes landing page forms and boosts inbox placement.

(07:14) Daniel shows how the same reply mindset on Instagram Stories boosts distribution while keeping interactions feeling human.

(09:28) They break down how replies become a goldmine of first-party data and even shape future content topics like reality TV.

(09:49) A rapid-fire holiday movie riff that goes from Die Hard and Home Alone to The Grinch, romcoms, and why Hallmark is secretly elite.

(11:15) Jay and Daniel pitch their very on-brand Thanksgiving “gain 5 pounds, then lose it” logic as the ultimate holiday hack.

Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/