Marketing doesn’t always have to be sunshine and sparkle—sometimes a little “doom” drives way more clicks. Jay Schwedelson digs into fresh data showing that negative words, emojis, and angles can outperform the classic “win-win” tone we’re all told to use. So if you’ve ever wanted to tell your boss that positivity is tanking your subject lines, now’s your moment. Plus, Jay gets fired up about weird moviegoers and horror trailers in a classic ridiculous question rant.

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Best Moments:

(01:30) Why "positive vibes only" might actually kill your marketing results

(02:44) Negative words in headlines generate 63% more clicks than positive ones

(03:31) Using “mistake” in your subject line can double CTRs

(04:48) Negative emojis outperform positive ones in email subject lines

(05:56) The “nope” subject line trick that boosts open rates by 17%

(07:45) Jay rants about people bringing blankets to the movies (and taking off their shoes)

(08:48) The battle of the trailers: Jay loves them, his wife hates them

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

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

Register here: www.GuruConference.com

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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/

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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

If you’re ignoring weekends in your marketing plan, you might be sleeping on gold. Jay Schwedelson and Daniel Murray are teaming up for “Bathroom Break” — a quick-hit series where they trade data-backed tips while pretending we’re not all scrolling on the toilet. This one’s all about why Saturday and Sunday might be your secret weapon for better engagement, higher intent, and less crowded inboxes.

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Best Moments:

(01:52) Jay admits to having no work-life balance — and why that matters for weekend strategy

(02:30) Daniel makes the case for less competition and more attention on weekends

(04:34) Sunday night sends are outperforming weekday ones for Daniel’s list

(05:30) Jay explains why weekend send times should never match your weekday schedule

(06:14) Open rate isn’t everything — high-intent opens matter more

(07:03) Jay’s weird morning habit: two minutes of direct sun to the eyeballs

(08:00) Daniel’s morning walk is less about coffee and more about mindset

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Follow Daniel on LinkedIn, leave a review for The Marketing Millennials, and tag them on Instagram to get reshared in their stories.

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

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

Register here: www.GuruConference.com

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

Most people don’t love their jobs—and that’s not only normal, it might be healthier. Jay Schwedelson unpacks the toxic myth that everyone should “do what they love” and explains why chasing passion often backfires. He shares why he doesn’t love his own job (and why that’s fine), what actually matters more than love, and how redefining career fulfillment might be the smarter move.

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Best Moments:

(00:30) Jay admits he doesn’t love his job—and that’s more than okay

(02:00) Why “do what you love and you’ll never work a day” is terrible advice

(02:45) Chasing passion can ruin the thing you once loved

(04:00) What really matters more than loving your job

(04:45) The quote from Eat, Pray, Love that nails it

(08:00) Jay’s gym rant: mirror flexing, water jugs, and the unholy sin of not wiping machines

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

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

Register here: www.GuruConference.com

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

Jay Schwedelson gets the truth about LinkedIn company pages from Michelle J. Raymond—and it’s not what you'd expect. Turns out those dusty, forgotten pages could be your brand’s biggest missed opportunity. They dig into what’s actually working now, why impressions are dropping for everyone, and how you can build a company presence that doesn’t feel like a corporate ghost town. Plus, Michelle reveals what happened when she stopped posting for two weeks straight.

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Subscribe to Michelle’s newsletter: https://b2bgrowthco.com/newsletter/

Check out her podcast, Social Media for B2B Growth: https://podcasts.apple.com/us/podcast/social-media-for-b2b-growth-linkedin-strategies-and-tips/id1603908569

Follow Michelle on LinkedIn: https://www.linkedin.com/in/michellejraymond/

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Best Moments:

(01:09) Michelle’s accidental journey from B2B sales to LinkedIn company page expert

(03:15) Why she doubled down on company pages when everyone else ignored them

(04:44) The quick page audit you should do today

(06:20) What kinds of content actually work on company pages (and what to avoid)

(09:00) Why follower count matters—just not the way you think

(10:56) Yes, your page looking dead is sending a message

(14:00) Michelle’s two-week LinkedIn break—what happened and why she did it

(19:00) The algorithm actually wants you to come back

(20:15) What platform Michelle would bet on if LinkedIn disappeared tomorrow

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

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

Register here: www.GuruConference.com

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

If your email performance is slipping even though you're using that classic “letter format” style, there’s a reason—and it’s not what you think. Jay Schwedelson breaks down why hybrid-looking plain text emails are quietly tanking results, and what real 1:1 messaging actually looks like. Also: laser planetariums, shoe policies at TSA, and the weird airport loophole that makes Jack & Coke at 8:30 a.m. seem totally fine.

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Best Moments:

(02:01) Why everyone’s using letter format emails—and what they’re getting wrong

(03:02) The sneaky visual signals that make your “personal” emails feel automated

(04:30) 600% higher reply rates when your email looks truly human

(05:15) Why your “plain text” email is still HTML—and why that’s okay

(06:15) The email strategy mistake of living in both the graphic and plain text worlds

(08:13) Jack & Coke at 8:30 a.m.? Only acceptable in airports, apparently

ㅤ

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

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

Register here: www.GuruConference.com

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

Waitlists might sound boring, but Jay Schwedelson and Daniel Murray make them feel like a secret weapon you’re probably underusing. They break down why waitlists aren't just for trendy DTC brands and how you can use them to test demand, gather leads, and build buzz—without sounding like a scammy giveaway. Plus, you’ll hear some strong opinions on self-checkout, impulse buys, and why Jay owns too many Lululemon hats.

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Best Moments:

(01:10) Jay confesses he’s never used self-checkout without needing help

(02:28) Daniel explains why waitlists matter even if you’re not launching a product

(03:35) Jay shares how he turns a free event waitlist into a hype machine

(04:42) Daniel drops the “rolling thunder” strategy for smarter launches

(06:44) Limited quantity launches aren’t just hype—they’re insight gold

(08:05) Jay admits he keeps buying hats he’ll never wear at Lululemon

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Follow The Marketing Millennials podcast and connect with Daniel on LinkedIn to share marketing topics you want to hear in future episodes.

ㅤ

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

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

Register here: www.GuruConference.com

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

Jay got a rare chance to dig into exactly how Amy Porterfield gets such ridiculously high value—and sky-high conversions—from her webinars, bootcamps, and intimate in-person events. And she doesn’t hold back. From rethinking your promo timing to why “masterclass” beats “webinar,” she shares the specific tactics she uses to drive results without burning out her audience. Jay Schwedelson is all in on her playbook, and after this, you might be too.

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Subscribe to Amy’s newsletter for weekly marketing tips that actually move the needle: https://www.amyporterfield.com/newsletter

Listen to The Amy Porterfield Show for deep dives on webinars, course creation, and smarter digital strategies: https://podcasts.apple.com/us/podcast/the-amy-porterfield-show/id594703545

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Best Moments:

(02:43) Why “webinar” is killing your sign-ups—and what to call it instead

(05:30) The simple live bonus that gets people to actually show up

(07:01) How often you should email between sign-up and go-live

(08:00) Why 7 days (not 2 weeks) is the sweet spot for promotions

(09:45) How to create “pre-launch breadcrumbs” that boost conversions

(14:15) What to do with all the people who don’t show up live

(17:15) Why she charges $37 for bootcamps—and gets 25% conversions

(20:45) How small events with specific goals outperform big ones

(23:10) Shrinking her audience on purpose (and making more money doing it)

(27:00) The one event mistake she keeps making—and how to fix it

ㅤ

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

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

Register here: www.GuruConference.com

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

If you want to watch this YouTube failure unfold give me a 'subscribe' RIGHT HERE!

https://www.youtube.com/@schwedelson/shorts

appreciate you!

J

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Best Moments:

(00:34) The real reason it’s powerful to admit when something isn’t working

(01:45) Why YouTube Shorts will rule the internet in the next three years

(03:00) Most marketers are dumping content on YouTube and calling it a day

(04:55) What having only 600 subscribers taught Jay about perspective and growth

(06:23) You don’t need to be great—just willing to be in it and learn

(07:45) If you’re not hands-on, your feedback and decisions are worthless

ㅤ

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

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

Register here: www.GuruConference.com

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