Sometimes Jay Schwedelson skips the marketing hacks and just gets real. This time he shares a personal story about nearly missing out on the love of his life and the lesson it left him with: regret is far heavier than failure. It’s raw, funny, and surprisingly relevant if you’ve ever hesitated before taking your shot in business or in life.

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Best Moments:

(01:09) The biggest turning point in Jay’s life that reshaped how he thinks about work and risk

(02:42) The sting of seeing someone you care about happy with someone else

(05:16) The bold move at the bar that changed everything

(07:45) Why you only need 10 seconds of bravery, not a lifetime of courage

(08:32) The torture of living in the land of what ifs

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

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Not every business thinks it needs an event, but Jay Schwedelson and Tahira Endean make a strong case for why you do. From building trust faster than endless email threads to creating the kinds of moments people actually remember, Tahira shows how events—big or small—drive connection, loyalty, and growth. She also pulls back the curtain on what makes event submissions stand out and why joy should be part of every strategy.

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Tahira’s book Our KPI is Joy is available on Amazon. Connect with her on LinkedIn.

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Best Moments:

(03:43) Why 10 minutes at a live meeting can replace 64 emails

(05:15) The role of trust in why events matter for any size company

(08:30) Designing experiences that the “remembering self” won’t forget

(10:15) Why in-person events are the antidote to AI sameness

(13:30) How she curates sessions and avoids AI content overload

(17:12) The must-dos and never-dos when submitting to speak at events

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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/

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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.

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Google just dropped a curveball for anyone using Chrome: you can now type prompts straight into the address bar and get Gemini-powered answers without ever leaving your browser. Jay Schwedelson unpacks why this matters for marketers, why LinkedIn isn’t punishing you for adding links (despite the myths), and the seasonal email trick that quietly spikes open rates. Plus, he can’t resist dropping in some TV takes—from Love Is Blind to the sad end of Outrageous Pumpkins.

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Best Moments:

(01:00) Chrome’s address bar turns into an AI prompt box with Gemini

(01:30) Why Jay thinks Google might win the AI wars

(02:30) LinkedIn’s product director says links do not kill reach

(04:00) Starting October, “invitation” subject lines boost opens by 24 to 28 percent

(06:00) Jay’s fall TV lineup: The Girlfriend, Love Is Blind, and a canceled pumpkin show

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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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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).

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Parenting mishaps, exploding diapers, and even a surprise bird incident somehow all tie back to smart marketing takeaways in this Bathroom Break collab between Jay Schwedelson and Daniel Murray. From no-scroll forms that skyrocket conversions to why your CTA button text might be killing deals, this one is equal parts messy, funny, and surprisingly useful.

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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:

(01:00) Daniel’s first baby carrier experience turns into a poop explosion mid-call

(02:56) Jay reveals how a no-scroll form boosted conversions by 60 percent

(03:35) Daniel explains why two-step forms make capturing emails easier

(05:00) Why quantifiable testimonials beat generic praise every time

(06:45) The danger of weak offers like “Request a demo” and how to make them action-based

(07:12) Why your CTA button text should never just say “Submit”

(07:30) Small copy details that build trust, like time estimates and progress bars

(12:13) Jay shares his own “bathroom break” moment courtesy of a bird

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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).

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Sometimes the best insights come from the strangest questions, and this Ask Us Anything proves it. Jay Schwedelson riffs on AI tricks you probably aren’t using but should, why half your “official-sounding” stats might be totally fake, and the one detail that makes your prompts 10x better. And just when it seems like things can’t get weirder, a question about Guam leads to toilets, vending machines, and why Japan might secretly be the best place on Earth.

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Best Moments:

(01:04) Why half the stats you get from AI might be made up

(03:00) The simple phrase that forces AI to stop inferring fake numbers

(03:45) How to get ChatGPT to write the perfect prompt for you

(05:13) The one trick that keeps AI responses fresh and not a year out of date

(07:01) Guam vs San Francisco and the real problem with Scranton, PA

(08:45) Why Japanese vending machines, toilets, and portion sizes make life better

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

Turns out the fastest way to win trust isn’t a hack at all. It’s radical transparency, smart self-service, and meeting people where they already are. In this chat, Jay Schwedelson digs in with Marcus Sheridan on the four pillars that make brands truly known and trusted, why YouTube might matter more than your website, and how pricing estimators and honest comparisons become AI-era trust signals.

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Connect with Marcus on LinkedIn, check out marcussheridan.com, grab his book at endlesscustomers.com or on Amazon, and reach out if you want him to speak or train your team.

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Best Moments:

(02:00) Becoming the Wikipedia of pools saved a failing business by obsessively answering every buyer question.

(04:06) The four pillars of a known and trusted brand: say, show, sell, be more human.

(07:00) The Big Five topics that always move the needle: cost, problems, comparisons, reviews, best.

(10:13) Use Marcus’s custom GPT to spin up Big Five content titles tailored to your business.

(11:38) Your YouTube channel is quickly becoming more important than your website for discovery.

(16:19) Pricing estimators drive 3x to 5x more leads and set better sales conversations from the start.

(18:26) AI won’t recommend brands that hide pricing or shy away from negatives; transparency is a ranking signal.

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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

LinkedIn just added some sneaky-powerful analytics, Instagram is rolling out a surprisingly useful tweak, and Jay Schwedelson has a clever email test that could boost your open rates without writing a single extra word. He also throws in a few life notes, from collapsing toy fads to what’s actually worth streaming this week. Quick, punchy, and packed with the kind of tiny updates that can quietly change your marketing game.

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Best Moments:

(01:00) Why LinkedIn’s new save and send metrics matter for your content strategy

(02:00) Posting more often could unlock thousands of extra impressions on LinkedIn

(03:20) Instagram finally lets you pin your own comments

(04:00) The no-preheader email test that can increase opens by 15 percent

(05:26) Labubu toys are tanking in value, Beanie Baby dreams crushed

(06:15) The Girlfriend on Prime is worth your binge, unlike that wild Netflix catfish doc

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).

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Riding in a driverless car might not sound like the ideal place to kick off a marketing chat, but Jay Schwedelson and Daniel Murray made it work. Between sweating it out in a Waymo and figuring out how to breathe again, they got into why Reddit is one of the most powerful (and underused) platforms for marketers. From spotting trends before they hit the mainstream to actually listening in on real customer pain points, this episode shows why ignoring Reddit means missing big opportunities.

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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:

(00:45) Trapped in a Waymo, overheating, and questioning life choices

(02:15) Daniel explains why he always adds “Reddit” to his Google searches

(04:15) Jay shares how to use ChatGPT prompts to surface top Reddit threads

(06:15) Daniel points out that Reddit conversations move faster than any other platform

(07:00) Jay’s Google search hack for finding Reddit content directly

(08:45) Why Reddit forces marketers to earn credibility instead of faking it

(09:45) The surprising safety and social perks of choosing Waymo over Uber

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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