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

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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

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.

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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 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