Podcast Summary: “GARY VEE!! 🤯 Stupidest Marketing Move! ➕ Attribution is Garbage? ➕ How to WIN on Social!”
Podcast: Do This, NOT That: Marketing Tips with Jay Schwedelson
Host: Jay Schwedelson (A), Guest: Gary Vaynerchuk (B)
Episode: 398
Date: August 19, 2025
Episode Overview
In this high-energy episode, host Jay Schwedelson welcomes marketing legend Gary Vaynerchuk (“Gary Vee”) for a no-filter, rapid-fire masterclass on modern marketing, authenticity, and adapting to the latest shifts in attribution and social media strategy. The conversation is both practical and philosophical, balancing tactical marketing advice with big-picture commentary on industry mindsets. Jay’s quick wit and honest self-appraisal provide the perfect counterpoint to Gary’s trademark candor and enthusiasm.
Key Discussion Points & Insights
1. The Stupidest Marketing Move: Boosting Bad Content
- Jay admits boosting underperforming event ads, asking if it's “epically stupid” to amplify content that didn’t do well organically.
- Gary explodes with agreement:
- “The single stupidest thing in the world of marketing and business... is amplifying content that clearly did not do well because it didn't do well organically… You're literally taking money and throwing it into a garbage and then lighting a match and burning it to the ground. So, yes, you are doing the single worst thing on earth.” (03:14)
- Takeaway: Only amplify content that already works organically. Do not cover up weak creative with paid spend.
2. Jab, Jab, Jab, Right Hook — A Modern Interpretation
- Jay digs into Gary’s famed strategy of giving value (“jab”) before making the ask (“right hook”), but wrestles with the disconnect between high-performing value content and low sales conversion.
- Gary’s clarification:
- “You give, you give, you give, and then you ask. And when they do not deliver on your ask, you do not feel bad or sad or mad at them… The concept of give, give, give is brand. And then you're going to convert a certain part of that audience.” (05:12)
- Notable distinction: The "ask" is not entitlement. Brand-building comes first—conversions follow.
3. Turning Winning Content Into Sales Machines
- Real-time coaching from Gary:
- Take a “winner” jab (organic success), post-produce it, and sample your own hit by tweaking it for a direct call to action.
- Example: Add yourself in the bottom corner, reacting, and at the end deliver the direct pitch: “Hey, thanks for watching... our big event is on October 19th, there’s a link...” (07:02–09:19)
- Gary’s music analogy:
- “You're sampling your own hit… You're taking a jab and you're converting it into a right hook.” (09:19)
4. Attribution Is Garbage
- Jay and Gary rail against “last touch” attribution:
- Jay: “Attribution is total garbage... You're assigning value to crap.” (09:36)
- Gary: “For 20 years Google got credit for things that other mediums were doing because Google became the de facto place you would go... People over-invested in search.” (09:45)
- Gary’s logic: Most sales are triggered by brand and cultural relevance, not the last platform someone clicks before buying.
5. Sales vs Marketing & Brand’s Role
- Gary distinguishes: Email and search are closer to “sales DNA,” not pure marketing, while “organic social is what worked in the 50s and 60s on television.”
- Quote: “Sales is what you do when you're not good at branding and marketing.” (10:34)
6. Math vs Art in Marketing
- Gary’s critique: Corporate marketing has shifted excessively toward “math” and data, losing creativity.
- “We are too in the era of math right now. And the beauty is 50/50.” (12:12)
- A strong brand needs both data and culture attunement.
7. Interest Media vs Social Media: The Platform Shift
- Gary’s paradigm: Social platforms are now driven by “interest” rather than just follower count.
- “Anyone... if it's in [their] soul... Yes, that person will crush... The fact that when I post my third Bon Jovi video, it will find people that have a propensity to give a fuck about Bon Jovi because that's how deep the AI is now...” (16:44–18:54)
- Leveling the playing field:
- “Follower count... I do believe within a half decade the following count might not even be publicly seen.” (19:11–19:25)
8. Best Practices Are Obsolete
- Jay’s rant: “By the time it becomes a best practice, it's an antiquated piece of crap...”
- Gary’s agreement:
- “Best practices is makeup on the real word, which is you need to be strategic at all times... Once it hits that status in corporations, it's garbage often...” (20:31)
- True advantage lies in daily “day trading attention”–monitoring platforms, algorithms, and cultural currents.
9. Relevance, Culture, and Pop Culture Strategy
- Gary’s framework: Winning marketing comes down to understanding:
- Platforms: Where is the attention?
- Algorithms: How does the content surface?
- Culture: What is the cultural context right now?
- Prediction: “Brand strategists are going to get replaced by pop culture strategists.” (23:00–24:46)
10. The Importance of Cultural Fluency in Marketing
- Gary stresses:
- “If you don't know what's going on... then you don't know how to market to them.” (25:36–26:29)
- Example: Leveraging inside jokes on Love Island and understanding niche cultural moments to deeply engage audiences.
- “Leaving comments as a brand in certain places... was incredibly fruitful for business results.” (25:38)
11. Ride Micro and Macro Trends
- Gary’s analogy: You have to catch the small waves (“micro-trends”) to ever position yourself for the big wave (“macro-trends”).
- “Many get worried about chasing every trend; but those moments become the seed of an eight-year movement...” (27:23–29:14)
- “If a brand's scared... Well, what about when [a trend] becomes the trend?” (29:00–29:14)
Memorable Quotes & Moments
- On boosting bad content:
- “You are literally taking money and throwing it into a garbage and then lighting a match and burning it to the ground.” —Gary Vee (03:14)
- On modern content remix:
- “You're sampling your own hit.” —Gary Vee (09:00–09:19)
- On last-touch attribution:
- “Attribution is total garbage... You're assigning value to crap.” —Jay (09:36)
- On the role of brand:
- “Nobody's buying a Labubu right now... because they got cookied and we followed them around... They're buying it because of brand.” —Gary Vee (11:35)
- On being authentic on social:
- “If you're chasing money... you're vulnerable. When you triple down on what gets you going... that's the move.” —Gary Vee (16:46–18:54)
- On trend surfing:
- “How the fuck are you going to catch the big wave if you're not in the fucking water?” —Gary Vee (28:57)
Fun/Personal Segment: Knicks Nostalgia (30:32–33:42)
- Jay and Gary nerd out over their 1990s NYC sports fandom:
- Gary’s all-in love for Patrick Ewing, Anthony Mason, Xavier McDaniel; his devastation at the 1994 NBA Finals loss.
- “[Ewing] is [my Knicks guy]. I will die on this hill. I hate how much Nick fans did not appreciate him enough... I cried like a seven year old boy [after Game 7 loss].” —Gary Vee (32:18–32:43)
Timestamps for Key Segments
- Intro & Gary’s Background: 00:01–02:11
- Boosting Bad Content is the Worst: 03:14–04:38
- Jab, Jab, Jab, Right Hook Explained: 05:12–05:46
- How to Convert a Jab to a Right Hook: 07:02–09:19
- Attribution Is Garbage: 09:36–10:34
- Math vs. Art in Marketing: 12:12–13:03
- Rise of ‘Interest Media’ & Authenticity: 16:01–19:25
- Best Practices are Obsolete: 20:04–24:20
- Pop Culture Strategy: 24:20–26:29
- Micro vs. Macro Trends (Surf Metaphor): 27:23–29:55
- Knicks Fandom/Personal Moments: 30:32–33:42
Final Thoughts
This episode is a tour-de-force of contemporary marketing wisdom:
- Stop hiding weak creative with paid spend.
- Build brand first, ask for the sale second.
- Attribution is deeply flawed—invest in relevance.
- Authenticity and tapping into real, current culture are non-negotiable.
- Chase what excites you; follow pop culture not "best practices".
- The opportunity for new creators is greater than ever thanks to “interest media” dynamics.
Required listening (or reading) for any marketer eager to thrive in a rapidly evolving landscape.