If you want to know how to change your marketing strategy in the age of AI, Gary Vaynerchuk has a blunt answer: stop guessing on upper funnel campaigns, stop running outdated A/B tests on the lower funnel, and start pouring at least 20% of your entire marketing budget into organic social media production. According to Gary, the midfunnel has eaten the entire marketing world — and almost nobody in a big company has noticed yet. He dropped that and a lot more in one of the most wide-ranging conversations we've had on the show.
Why 93% of Your Marketing Budget Is Being Wasted
Gary didn't ease into this one. When asked what Fortune 500 CMOs are saying about AI and their marketing mix, he pivoted immediately to what they're doing — which, in his view, is mostly the wrong thing.
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Gary Vee breaking down the midfunnel marketing framework live on air
Watch at 18:45 →
"Your marketing department is wasting 93 cents of every dollar they spend." That's the quote. And he wasn't being hyperbolic for effect.
His argument is that we are living through a radical transformation driven by what he calls the midfunnel. The upper funnel — big brand sponsorships, TV spots, guessing games with expensive campaigns — is largely a relic. The lower funnel — the 2016-era A/B testing beta frameworks most performance marketers are still running — is also broken. What's taken over the middle is organic social content: the kind of content that builds trust, creates community, and converts at scale without a massive media buy behind it.
His prescription is simple but uncomfortable for large organizations: every brand on earth should be spending at least 20% of their total marketing budget purely on social media organic content production. Not paid. Not boosted. Produced, published, and optimized based on what actually performs. Then and only then do you take the content that's working organically and push dollars behind it — up for brand, down for performance.
The reason most big companies aren't doing this? The structure of their marketing departments was built for a different era. And nobody wants to be the person who tells the CMO that the $10 million sponsorship deal is dead money.
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Gary reacting to vinyl sales hitting $1 billion for the first time this century
Watch at 09:22 →
Why Vinyl Sales Just Hit $1 Billion (And What It Means)
For the first time this century, vinyl music sales eclipsed $1 billion in a single calendar year. Sales records are up roughly 10% in 2025. That's not a blip — that's a trend with real cultural momentum behind it.
Gary's take? It's both decorative and deeply behavioral. Some people are buying records to hang on walls. A lot are buying them as collectibles. But the more interesting explanation is what he calls a subconscious counter push to extreme digitalization.
People are quietly, sometimes without even realizing it, reaching for things that feel physical, real, and human. Vinyl sounds different. It requires intention. You have to get up and flip it. That friction, which the streaming era tried to eliminate, is now the feature.
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Gary laying out his analog barbell theory and the businesses he's investing in
Watch at 12:10 →
He also walked through how cultural trends like this spread: it starts with the Brooklyn creative types who want something authentic and underground. Then the Manhattanites pick it up to stay cool. Then it bleeds out to California, Texas, Florida, and eventually everywhere. By the time it's mainstream, it's a billion-dollar market.
The deeper signal Gary is reading here is that humans correct themselves at a level we consistently underestimate. The more overwhelming digital life becomes, the harder people reach for something tangible.
What Analog Businesses Will Explode as AI Takes Over
This is where the conversation got genuinely exciting. Gary's framework is a barbell: on one end, extreme AI and digital automation; on the other, extreme analog and physical experience. He believes the two ends of that barbell will both grow dramatically over the next decade, while the middle gets hollowed out.
His list of analog opportunities he's bullish on:
- Restaurants — He's part of a restaurant group and is pushing his partners to open a concept where guests check their phones at the door and sit at communal tables. He thinks people are hungry for that.
- Physical retail — Not the dying mall model, but a reimagined half-experiential, half-shopping environment that people will actively seek out.
- Live events, concerts, and venues — The Sphere in Las Vegas is a perfect example. Everyone thought it would fail under its debt load. The stock is up 3x.
- Alternative sports — He's made significant bets on pickleball, Unrivaled (the 3-on-3 basketball league), padel, slam ball, a wiffle ball league, and sailing. His thesis is that decentralized distribution and the AI-proof nature of live sport make these uniquely valuable.
- Drive-in movie theaters — He floated this as a left-field idea and immediately acknowledged that most people watching would say yes, they'd go. His question: what happens to the person who builds 39 of them and creates a real chain? Especially when, seven years from now, you can produce your own AI-generated films and show them through your own analog distribution network.
The through-line across all of these: AI at scale creates analog opportunity at scale. The entrepreneur who understands both sides of the barbell is the one who wins the next decade.
What Is Midfunnel Marketing and Why Does It Matter Now
Gary used this conversation itself as the clearest possible example of midfunnel marketing. The show, the production, the organic social clips that get made from it — all of it lives in the midfunnel. It's not a billboard. It's not a retargeting pixel. It's content that builds a relationship with an audience over time.
The TikTokification of social media — his phrase — has made this layer of the funnel the most powerful one available. Attention lives there now. Trust is built there. Purchases increasingly follow from there.
His framework for how brands should execute it:
- Produce a high volume of organic social content consistently
- Let the market tell you what works by watching what performs
- Take the winners and amplify them with paid spend — up into brand awareness, down into direct response
- Never spend media dollars guessing on a campaign that hasn't been validated organically first
It sounds obvious when laid out this way. The fact that most Fortune 500 companies still aren't doing it is, in Gary's words, incomprehensible.
Should You Write a Book Young or Wait Until You're Older
Ryan Holiday wrote Trust Me, I'm Lying at 25. Should more young people write books instead of waiting for some imagined threshold of wisdom?
Gary's answer was nuanced and honest. He pointed to his own first book, Crush It, published in 2009, and admitted he still looks back at it and thinks: how did I write that? His argument is that young people with genuine insight have a specific advantage — they see things others can't because they're not playing by yesterday's rules. Fresh eyes are dangerous eyes.
But he also believes the best books tend to come at the beginning or the end of a career. Your first book is written with the energy of someone who has their whole life of accumulated observations ready to pour out. Your last book synthesizes decades of hard-won wisdom. The middle books, in his view, are often the weakest.
His encouragement to young writers: if you have something to say, say it now. Don't wait for permission or a credential. The people who win are the ones who start before they're ready.
What Gary Vee Is Betting Big Money On Right Now
Beyond the analog businesses listed above, Gary touched on his investment in collectibles as a long-running thesis. His argument has always been that physical, tangible objects with community attached to them — sports cards, comics, collectible toys — are a gateway drug to belonging. That thesis has only gotten stronger as digital everything has made physical community feel more rare and therefore more valuable.
He also talked about his MasterClass partnership, which he took specifically because it addresses something he genuinely believes: that a real-world AI and marketing education at a fraction of the cost is more valuable than a traditional MBA right now. The MBA model, in his view, no longer delivers the ROI it once promised.
Is TikTok Shop Actually Worth It for Brands in 2025
The conversation ended with a quick but punchy exchange on live commerce. Gary's view: China is going to do a trillion dollars in GMV this year through live social shopping. TikTok Shop is doing real numbers in the US. Meta is clearly preparing a major push. YouTube will follow.
On TikTok post-ownership-change: he said he's felt nothing different on the platform and isn't losing sleep over the corporate structure. His more important point was about the underlying mechanism. You only need to subsidize a platform that doesn't work on merit. TikTok Shop works. The engagement is real. The commerce is real. Brands that aren't taking it seriously are going to look back on this moment the same way companies that ignored Instagram in 2013 look back now.
The window to build before it's crowded is always shorter than it looks. That's probably the most consistent thing Gary has been saying for 15 years — and he's been right about it more often than not.
