Boston accents, tariff talk, and some surprisingly solid dating advice all in one shot. Jay Schwedelson keeps it real on this quick-hit episode, breaking down why tariffs still matter for your marketing strategy (even if the headlines have moved on) and sharing a sneaky email tactic that’s crushing right now. Then, things take a hilarious turn as he tackles a stack of dating questions with zero filter—because why not?

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Best Moments:

(01:15) Jay cracks up over Boston’s official accent dictionary and his new favorite word, “donkeys.”

(02:01) Why tariff concerns aren’t as “over” as marketers think—and what it means for your promos.

(04:20) The value-per-use marketing trick that’s driving double-digit email engagement boosts.

(07:15) Why mentioning tariffs in your subject lines could give you a 19% lift in opens.

(08:30) Jay’s blunt take on what to do when someone says “we should hang out sometime” but never picks a date.

(09:45) The Instagram ex-following debate—fine or full red flag?

(10:36) When “I need space” actually means “this relationship is toast.”

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

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

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

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Templates may save time, but do they kill your creativity? That’s the debate Jay Schwedelson and Daniel Murray dive into during this Bathroom Break collab. They get real about why marketers rely on templates, how they backfire, and when it actually makes sense to break the rules. Plus, a tangent about AI glasses you didn’t know you needed.

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Best Moments:

(01:45) Jay compares buying the same shirt to marketers clinging to templates.

(02:30) Daniel explains why canned templates make brands invisible on social feeds.

(03:36) Jay reveals the “new template” trap that lures teams into stale content.

(05:15) Daniel shares how custom styles keep newsletters consistent without blending in.

(06:00) Jay points out how copying common webinar formats leads straight to “nowheresville.”

(06:18) Daniel highlights why unpolished, text-based emails often outperform slick designs.

(07:09) The two riff on AI glasses and the future of wearable tech.

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Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights.

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Check out our 100% FREE + VIRTUAL EVENTS! ->

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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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Your company doesn’t matter as much as who you connect with through your content. Jay Schwedelson explains why building real relationships through podcasts, newsletters, or any content platform beats chasing vanity metrics like downloads or clicks. It’s a fresh way to think about your brand’s storytelling and networking—less about audience size, more about the right people you actually meet and collaborate with.

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Best Moments:

(00 00) Why your business needs content that forces interaction with important people

(02 00) How inviting guests to your podcast breaks down cold-call barriers

(03 00) Jay’s secret behind landing high-profile guests like Gary Vaynerchuk

(04 30) Reimagining content as a tool for building strategic relationships, not just audience growth

(06 00) It’s never really about downloads—focus on who you want to meet instead

(07 00) Jay’s hilarious story about battling a fly that took over his house

(09 30) Don’t miss Guru Conference, a free virtual email marketing event with big names

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Check out our 100% FREE + VIRTUAL EVENTS! ->

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Anne Handley is not here to bash AI—she actually uses it—but she is here to warn us about what happens when we use it too early, too often, and for the wrong reasons. Jay Schwedelson gets into it with Ann Handley about how to stay creative when AI wants to take over your brain, what’s really at stake for writers, and why being a good marketer still means sounding like an actual person (even if it’s a sweaty, messy one).

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Subscribe to Total Annarchy—Ann’s free newsletter on writing and marketing that’s actually worth reading.

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Best Moments:

(01:31) Why she’s more afraid of humans becoming robots than robots becoming human

(04:00) The biggest mistake creators make when using AI

(05:15) A smart rule of thumb for where AI should save time

(07:15) How we’re being trained to accept boring content—and how to fight back

(08:08) The rise of AI trigger words like “unlock” and “discover” (and why they’re ruining copy)

(09:00) Are marketers avoiding copywriting as a career now?

(11:18) The case for “thoughtstipation” and why prompt engineering is not the future

(14:00) The very human way Ann used AI to review her book draft

(17:30) Her 30-minutes-a-day reading challenge and why it rewires your brain

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Check out our 100% FREE + VIRTUAL EVENTS! ->

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Ever trusted an AI-generated stat only to get called out? Jay Schwedelson drops the one prompt that keeps bogus numbers out of your deck:

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Then he swaps analytics for dice as he relives a wild Vegas trip where his crew turned pennies into payouts. Short, sharp, and surprisingly useful, this one saves your credibility and maybe your next casino night.

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Best Moments:

(01:01) Ben’s meeting nightmare proves blind trust in AI can burn you

(03:00) ChatGPT admits 40-50 percent of its numbers are flat-out wrong

(03:32) Jay shares the exact prompt to separate sourced stats from AI guesses

(08:15) Blackjack drains wallets, but craps turns into a money-making marathon

(09:55) A stranger flips a $100 chip to Jay’s friend after a legendary 25-minute roll

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Check out our 100% FREE + VIRTUAL EVENTS! ->

Guru Conference - The World's Largest Virtual EMAIL MARKETING Conference - Nov 6-7!

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Not gonna lie, this one gets real. Jay Schwedelson and Daniel Murray go beyond the usual follower-count talk to break down what really matters when it comes to audience size—and what doesn’t. Social proof, ad credibility, platform strategies, and how to avoid looking like a ghost town brand all come into play. Whether you’re trying to grow a brand or just not embarrass yourself online, this one’s got some gems.

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Best Moments:

(00:40) The real reason Jay preps for Q4 months in advance—even if he procrastinates holiday shopping

(01:55) Why followers still matter when it comes to legitimacy and social proof

(02:54) Jay checks business credibility by LinkedIn followers, not websites

(03:49) YouTube Shorts outperforming subscriber-heavy accounts—and why that proves the algorithm has changed

(04:30) Why big brands run multiple burner accounts on social to maximize reach

(05:15) Running ads? People will click your profile—and your follower count influences their trust

(05:45) Followers unlock newsletter and broadcast features you can’t fake

(06:00) Set a baseline number to avoid looking sketchy—and stop chasing vanity metrics

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Check out our 100% FREE + VIRTUAL EVENTS! ->

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Instagram just changed the game by making posts searchable on Google—and Jay Schwedelson is here to tell you why it matters way more than you think. Plus, he breaks down the most overlooked, no-cost growth move on LinkedIn that could double your visibility with zero effort. If you’ve been sleeping on newsletters or just vibing your way through captions, this episode will wake you up.

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Best Moments:

(00:45) Instagram posts are now fully searchable on Google—even without logging in

(02:15) Why “weekend vibes” captions are killing your search visibility

(03:15) Tagging a location helps your post rank better in search—even if it’s generic

(04:30) The wild reason launching a LinkedIn newsletter beats the algorithm

(05:45) On average, 20–30% of your audience will subscribe to your LinkedIn newsletter

(07:30) LinkedIn now lets you use video as the header image for newsletters

(08:15) The first two words of your newsletter title are make-or-break

(09:45) Jay’s friend deleted Instagram and gave a TED Talk no one asked for

(10:55) The group text etiquette violation that made Jay nearly disown a friend

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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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Jay Schwedelson finally found someone who might just have the answer to his time struggles: Rebecca Shaddix. She’s not only a Forbes contributor and the force behind UCLA's Women in Tech research, but she’s also on a mission to rescue your day—90 seconds at a time. This episode isn’t about productivity hacks that require color-coded calendars or waking up at 4 a.m. It’s about the tiny gaps you already have and how to reclaim them with purpose.

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Listen to Rebecca’s podcast Time Billionaires for short, actionable ways to reclaim your day. Learn more at timebillionaires.org and follow her on LinkedIn.

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Best Moments:

(01:00) Why a car accident at 15 forced Rebecca to rethink how she used time

(02:45) The connection between micro moments and COVID-era burnout

(04:45) How filling short gaps with email and doomscrolling backfires

(06:02) The simplest shifts to stop draining your brain between meetings

(07:30) Rebecca’s favorite 2-minute actions that actually reset your energy

(09:35) Why we check email too often—and what to do instead

(12:04) Rebecca’s exact daily structure, from no-phone mornings to energy-aligned gaps

(14:00) The six categories she uses to decide how to fill her micro moments

(17:00) Why we spend time on things we’d never spend money on

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Check out our 100% FREE + VIRTUAL EVENTS! ->

Guru Conference - The World's Largest Virtual EMAIL MARKETING Conference - Nov 6-7!

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Trying to get attention for a new product or newsletter and hearing crickets? Jay Schwedelson drops a simple mindset shift that can actually double or triple conversions—without changing your offer. It’s all about how fast you get people to act, and Jay has a playbook for doing it that works across email, social, popups, and even SMS. Plus, he weighs in on the Coldplay kiss cam scandal, where tech execs and brand marketers collided in the weirdest, most viral way.

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Best Moments:

(01:01) Why even your most exciting announcement is likely to flop

(02:14) The psychology trick that creates urgency instantly

(03:15) How to “fake limit” a webinar and still give everyone access

(04:30) Smart ways to reward the first few buyers, subscribers, or registrants

(05:45) The exact tactic that got 1,000 signups in under 30 minutes

(06:16) Jay’s take on the viral Coldplay kiss cam mess—and the wild data behind it

(07:45) Over $250K was bet on whether the CEO would be fired

(08:15) A fast food chain’s promo code response: Coldplay

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Check out our 100% FREE + VIRTUAL EVENTS! ->

Guru Conference - The World's Largest Virtual EMAIL MARKETING Conference - Nov 6-7!

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma

Memes aren’t just for Gen Z or internet junkies—they’re a real-deal marketing tool, and Jay Schwedelson teams up with Daniel Murray to break down exactly why. From condiment debates to viral ad strategies, they get into how memes can signal audience empathy, drive shares, and even outperform traditional ad formats. If you’ve ever wondered whether your “serious” brand could pull one off—yep, you probably can.

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Best Moments:

(02:05) Jay's traumatic first Florida burger with surprise mustard and ketchup

(03:00) Daniel explains why memes are the language of the internet

(03:45) How to safely create memes without copyright issues or creative risk

(04:20) Memes as powerful ad formats that prove you understand your audience

(05:26) Why you shouldn’t keep using the same carousel over and over

(07:15) Jay’s trick for finding viral meme formats to recaption for your niche

(08:30) How platforms punish watermarked or reposted content

(09:05) Want to reuse a hit meme? Resize it first or risk getting throttled

(09:57) Daniel’s hot take: skip Taco Bell, hit the local burrito joint

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Follow Daniel on The Marketing Millennials and let him know what you want future bathroom breaks to cover.

ㅤ

Check out our 100% FREE + VIRTUAL EVENTS! ->

Guru Conference - The World's Largest Virtual EMAIL MARKETING Conference - Nov 6-7!

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ㅤ

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/

ㅤ

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma