Sometimes Jay Schwedelson gets into consultant mode, and with Gary Vaynerchuk in the hot seat, it turns into pure gold. This conversation is part marketing therapy session, part culture playbook, and part Knicks nostalgia trip. From why boosting bad creative is like lighting money on fire, to how brands should actually ride viral waves without getting lost in them, Gary breaks it all down with his trademark intensity. If you’ve ever wondered where branding ends and sales begins, or how to play the long game in the new era of “interest media,” this is one you’ll want to hear all the way through.

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Check out Gary Vaynerchuk’s book Day Trading Attention for a practical breakdown of today’s most effective content formats, explore more of his work at garyvaynerchuk.com, or follow him on Instagram for his latest insights.

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Best Moments:

(03:14) Gary calls boosting underperforming posts the single stupidest thing in marketing

(05:11) The nuance of “jab, jab, jab, right hook” and why entitlement ruins the ask

(07:12) How to sample your own winning content and turn it into conversion gold

(09:45) Why last-touch attribution is total garbage and branding gets lost in the math

(15:22) Gary imagines going full suit-and-tie just to flip culture on its head

(18:00) Why niche passion beats follower count in today’s “interest media”

(23:03) The PAC framework: platforms, algorithms, culture as the real marketing playbook

(28:12) The difference between viral micro-moments and long-term cultural movements

(30:54) Knicks heartbreak in ’94 and why Ewing and Mason still matter

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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!!

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