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Do This, NOT That: Marketing Tips with Jay Schwedelson l Presented By Marigold

GARY VEE!! 🤯 Stupidest Marketing Move! ➕ How to WIN on Social! w/Gary Vaynerchuk | Ep. 398

Do This, NOT That: Marketing Tips with Jay Schwedelson l Presented By Marigold

GURU Media Hub

Growth, Education, Email, Business, Revenue, How To, Entrepreneurship, Marketing, Profit, B2b, B2c

5715 Ratings

🗓️ 19 August 2025

⏱️ 34 minutes

🧾️ Download transcript

Summary

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.

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.

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

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

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/

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

Transcript

Click on a timestamp to play from that location

0:00.0

Welcome to Do This, Not That, the podcast from marketers.

0:05.0

We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode.

0:11.0

We also keep it short, like this intro. Let's check it out.

0:15.0

Hey, just want to jump in here real quick on this super exciting episode with Gary Vee, Gary Vaynerchuk. He's awesome. But, you know, we try to keep this, not a family-friendly show, but slightly family-friendly. You won't find us using a lot of crazy words, but sometimes Gary Vee goes off and does his thing, which is great. That's his vibe. That's his style. And I'm all for it. But I just want to give you

0:37.8

a minute here in case you're in the car with kids or you have a certain chill vibe going on. And you're like, wait a minute. I wasn't ready for that. He's fantastic. But just wanted to give you a little bit of a moment here, pause before you get rolling and cannot wait. This is one of my favorite things I've recorded. So hopefully you enjoy it too.

0:37.1

We are back for the Do This, Not That Pod And not wait. This is one of my favorite things I've recorded. So hopefully you enjoy it too.

0:55.7

We are back for the Do This, Not That podcast. And I mean, I never been more excited about anything in my entire life, let alone this episode right here. So who's here? So we have Gary Vaynerchuk. Now, you probably know him as Gary, but you probably just know him, period. So doing an intro on him is super awkward and weird, but I'll do it anyway.

1:13.6

He's easily one of the most influential entrepreneurs and marketers on the planet.

1:17.6

New York Times best seller of this book, Day Trading Intention, which I will tell you, he didn't tell me to say this.

1:22.6

This thing is wild.

1:23.6

I'm writing a book right now, and this thing just ruined it for me because my book sucks. And this thing's phenomenal. And I have massive imposter syndrome. If you're in marketing and you haven't read Day Trade Attention, then you're not really in marketing. Greatest book of all time. But his background, he's not just some famous dude. He took a family liquor store from super small to the $60 million

1:44.8

e-commerce thing when people didn't even know what a Google ad was. Then he founded Vayner Media,

1:50.2

which is this incredible agency working with Pepsi and fanatics and Indeed and so many others.

1:55.7

And he's also chairman of Vayner X, which is this wild modern media company that has

2:00.6

NFT, V friends, and intellectual

2:03.0

property and speaker bureaus, all this stuff. And the dude's got 50 million followers. There's like

2:07.7

seven of him. He's Gary V. He's here. Gary, thanks for coming on, man.

2:11.8

Dude, honestly, I might audio clip that and make that my Chiron for everything I do.

2:16.1

You're very, no, I'm joking, but thank you. I you love it jay thank you so much for having me bro i'm i'm super stoked to have you here and i don't want to waste any time and do the whole what was your story and tell me about wine and all this stuff because i love that about you but i want to get into it i need to put a USB in your brain so i want to ask you lots of random, random stuff. So here, and I've been watching, I've been, I've been all in on all your content. So here's my first question. I have this events business. We put all events and we're doing something stupid. Okay, so what we do is we'll go out there and we'll put ads on social media on on Instagram or content on social media

2:51.6

Instagram LinkedIn whatever and the ones are trying to get people to register and stuff

2:55.6

and mostly when they're not doing well what we do is we put ad dollars we amplify we boost

3:02.5

them with ad dollars to try to almost hide this crappy creative that we've made.

...

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