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 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

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! ->

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

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

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