Gary Vaynerchuk bets on analog revival: drive-ins, vinyl, and physical retail as the counterweight to AI

sort of what the future of generative UI might look like. Jordy, why are you laughing?

Because the chat is doing a bunch of wombos.

Oh, okay. We got to work on womos. Uh, we will be integrating those more in the near future. But we have our next guest in the waiting room, Gary Vaynerchuk from Vayner Media. Gary, how are you doing? Welcome back to the show.

Do you know about womos?

I do not, my friend.

You got to learn about womb.

You got to learn about womos. They are the next meta. They are the next meta. If you're not doing womos in 2026, you're getting left behind. Womos are word combos. So the example would be uh a quich is quirky and niche. You put it together and that's quish or lorraine. Lore

is a that's a that was a risky start for the first word.

Yeah, that's a risky one. Lorraine. Lorraine is a better is a better one. Give me if I say Lorraine

boys first first and foremost

congratulations.

Thank you.

Thank you.

I really mean thank you. Uh, I remember I remember our very first call. I think it was in Q1 of 2025. So, we were just maybe

like a little a little just a few months into the show and you

even at that point we were very very very small. I think we had maybe just gone live a few times and you told us you guys you you said go harder. We were already going pretty hard but you said go harder

and uh we certainly did. So, um

and go multiplatform. That was really huge too. you you you were you were very early in like why don't you have a newsletter right now? Why aren't you on YouTube in multiple ways? Why aren't you on Instagram yet? And so we did the uncomfortable thing of posting pretty subpar content for a while but it started the compounding very very early and now stuff's really much better. everything stop starts subpar, right? Like when you start working out or when you start singing or draw like you know like

I for everybody who's watching right now every business every personal brand

every B2B every B TOC the to not take advantage of the attention media landscape that's in place right now.

Um it it's really uncomprehendable to me. There's never been a time in the history of humanity or business where the cost of distribution is zero for the distribution. It's there's costs in the content

and the way you do it but the upside is so extraordinary against the investment

and when you frame it up properly multi- channelannel multiformat

the uh the business outcomes can be extraordinary and um I'm happy to see you guys get one.

Yeah. Well, are you is it is it is it funny that uh is it funny to you that that it feels like

it feels like in some ways we're like a decade into live streaming and yet

two decades by some measures.

Well, yeah, two decades by some measures. But like Twitch has been big for a long time. There's been so much attention there.

I mean I mean I wrote I wrote this book in 2008. It came out in09. Crush it. In the back of the book I talk about Ustream and live streaming.

Yeah.

Yeah. I mean, you know, it es and flows and to your point, like I mean, I can't even comprehend the economic impact live social shopping is going to do over the next 10 years for humans and consumer businesses. Um, yeah, it's all the same stuff, brother. It's always

been around forever and it's always the beginning, right? Like it's just kind of the way consumer behavior and human behavior works. Um yeah it does it does surprise me how many more people have not replicated the very you know basic strategic framework that you guys executed in this genre that's available

well the interesting the interesting thing is we there's there's easily been a hundred a hundred shows that have like taken some level of inspiration from what we're doing it's still very very hard it's still very very hard to break through right there's it's not just it's not just the overlay and the format but I have been surp I I've been very confident and I've said this on podcasts for you know we've talked about this going back probably six six to eight months ago. You should take this format of a live stream and you just add a extra level of production beyond you just have a laptop there and you're hanging out and you apply that. The example we'd always talk about is like cooking where all you need is like a cool kitchen. You that's your set. You have a couple of cameras, so you have different angles, and then you just say, "Hey, every day at 3 p.m. I'm going to cook dinner. This is what I'm going to cook. Here's the schedule. You can make dinner with me." And I think that that's like an entire niche that you could build around. You could in integrate guests into something like that, too. So, you have different, you know, content creators coming through every day. And then I think you can apply that to a bunch of other things. Sports has honestly been the most advanced in terms of live streaming.

Um, so credit credit to them. Yeah.

Yeah. I mean it's it's it's there for the taking. A lot of things are there for the taking.

Yeah. Uh how are you thinking about uh how branding and marketing will evolve? I had this interesting moment this week with the uh GBT images to launch where suddenly any brand like basically fully democratized highquality product photography. Now, there's still categories where like I don't want you to AI generate the the product photography. Like even apparel is actually interesting where like fit matters a lot. And so if you generate a bunch of AI images of your shirt and then I buy it and it doesn't fit well, like I'm not going to be happy about it. But for a bunch of categories, it's cool. And I always kind of have this like kind of strange moment where uh it used to be you could identify an entrepreneur's ability by their product photography in some way. Because even if somebody's like bootstrapped and scrappy, like they would find that friend and say like, "Hey, do me a favor. Help me get some great images." And you could kind of categorize like a company that you're seeing online like, "Okay, could this person figure out how to get great product photography or not?" But now the bar is just so much lower. You're you're like a couple prompts away from it. And so it feels like it's going to be harder than ever to stand out online.

Well, I mean, there's a lot there. I mean, it's all we just got done talking about how hard it is to stand out online,

right? Like like the the cost of entry is zero, but you know, this is a competition. Like you know, everyone's trying and so everyone will make content, video, picture, audio at a level that is uncomprehendable to all of us that were born prior to 5 minutes ago. and this won't be another transition. I think, you know, there's there's always going to be um a timing game to this, right? So, right now, you know, like this open claw,

you know, allows me to do things that a lot of people aren't thinking about right now. And me knowing that and me playing with that and then even more interestingly, how creative or strategic am I with the Agentic agents and what are they doing for me? How do I understand blah blah blah blah blah? So, I think it's kind of always going to be the same thing like whether it was electricity and some people put electricity in your home and other people were scared to because there was demons in it or you know the car or the the you know the typewriter is one that I've like been fascinated by the competitive advantages of the companies that actually brought typewriters in versus you know putting penmanship on a pedestal you know like it's just and computers and the internet and mobile devices and open source versus closed source and social media Now AI, you know, look, this AI thing is no joke. We all know that it's big stakes. There's a lot to it. But, you know, I still think whatever that human was to being scrappy to find their friend for the photography, you know, that scrainess is going to be deployed into something else.

Totally. Totally.

And so I also think

Right. And I also think that we're about to see the explosion of analog, right? Like I think this barbell that I keep thinking of. Totally. I I've been thinking like, okay, you want to start an apparel brand, you want to go on Instagram or Tik Tok and duke it out with like 10,000 other brands or why don't you like find somebody that has a retail store that they can't rent out and like do a deal with them and just try to get big in your hometown again, you know?

And and my argument would be would be and

Yeah.

Right. Like to me this bar like I just extreme AI is creating extreme analog. I really do think it's a barbell. I think in the next 10 years, obviously it's 2036, but I feel like it's going to feel like 2050, which actually is bringing the rise of 1950. I couldn't be more impressed with what Ari Emanuel and others are doing that are investing in all these analog businesses. I I could not be more interested in physical retail, in event- driven businesses, in concerts and venues. And I I think the the rise of Analog. I have a restaurant business uh part of a restaurant group. I keep pushing my partners who are really operating. Let's open a restaurant that makes people check in their phone as soon as they walk in. Let's put people in group tables. Like I think there's, you know, you see what's happening with flip phones.

Yeah.

Genet Alpha buying them. We see vinyl sales. You know, I've been very at the forefront of collectibles. I felt collectibles was something tangible and was a gateway drug to community. if you've never been to San Diego Comic- Con or the Sports Card National or Fanatics Fest. So, I think there's a lot of interesting nondigital realities that are coming as a counter move to the insanity of AI advancements. We're literally within a half decade not believing a single video, not a single [ __ ] video that's on the internet. Like,

in five years, if we're having this video, this interview right now,

yeah,

most of the audience is trying to figure out if we're real or not. that is that is very real and has real substantial counter opportunities. So

yeah,

you know, the photographer who's sad when I hear that, I'm like, no, no, no, you might actually crush in a different way. And so I'm curious to see what the counter uh scaled moves are going to be of the next decade. And I think for any real entrepreneur, they're not crying about AI killing them. They're curious about what AI at scale is going to create opportunity for them.

Okay.

Totally.

Uh let's go deeper on analog. I want your reaction to this headline that for the first time this century, vinyl music sales eclipsed $1 billion in a calendar year. Sales vinyl records are up something like 10% in 2025. Yeah, they're effectively like 10% of like global streaming revenue is just vinyl still.

It's bigger than CDs. It's making a bigger comeback than other formats. Uh what what is your what is your reaction? Is it people looking for wall decorations? Are they actually listening to the vinyl? Do you have any idea of like what we should read into that idea of this nostalgic format?

Are you and your I mean do you see my shelves here? Like only thing I've been thinking about for the last seven, eight years or not only but like very hot on this. Yeah. I mean the answer is yes to both. Some of it's happening with decorative. A lot of it's happening with collectibles.

Even more is happening with subconscious counter push to extreme digitalization.

Sure.

Yeah. There are people, this is, by the way, one of the reasons we're not going to see unlimited television commercials and social media content that's just pure AI from the biggest companies in the world is every time they try to go there, you probably have touched on your show, McDonald's, others, they get such backlash because the whole world is so scared that AI is going to take their job that the consumer is pushing against it. And then that's one part and then the second part is yeah, people are starting to do counter behavior consciously and unconsciously. And um and and then there's just swings of swings of trends like you know like music sounds great in a great record player and like people like oh this is kind of cool too and like it becomes behavioral. It it you know it starts in the same stuff you know this. It's like the Brooklyn extremists are like let's go you know hippie cool culture and they get their little thing in a little subpocket. It bleeds out a little bit. Then the Manhattanites feel like they're not cool anymore. So they do it to keep up with the Brooklyn Knits. And then we have that version everywhere in California and Texas and Florida and everywhere in the world. And so it's just it's normal consumer behavior, but I it is clearly a counterpoint to extreme in feed in digital consumption. And I think that's great. It's it speaks to the thing I most believe in, which is humans correct themselves at a level that we are unbelievably underestimating. the the sheer adaptability of the human race is extraordinary.

Let's give it up for us. Uh

sports well said.

I want to talk about sports.

Yeah, I mean sports are a good example. We were talking earlier, a friend of the show, Josh Kushner, is looking to acquire a stake in in the Giants and out of his new eternal fund, which is

uh basically a will seemingly be a collection of like, you know, evergreen bets that aren't that can't be disrupted by AI because I don't want to watch

simulation of the Giants. The sphere is another good example.

Crazy. Everyone was thinking that that was not going to go well. They were worried about the debt and the stock is up like 3x. it's done very well. Uh, how are you thinking about both opportunities in new physical locations like the Sphere and then also in the the the the more legacy brands like the San Francisco Giants, the New York Mets, the different uh sports franchises out there?

Yes.

I I you know, it's really interesting. Tie a couple things together. this distribution channel that you and I are on right now, right? The fact that there are people watching.

Yeah.

In in a way that 40 years ago, somebody would had to say, "You guys are good faces and you look good and you're charismatic and you might get a shot on this distribution." This decentralization of distribution along with with this analog and not disrupted by AI thing is why six or seven years ago, I started investing very heavily in alternative sports. So, made a big bet on pickle ball that I think is going to work out quite well.

Uh, you know, unrivaled, the threeon-ree basketball league, AJ and I, my brother, early investors in that,

the whipple ball league,

the sailing league, um, Slam Ball. I So, I've been very aggressive on alternative sport investing, Padell. Yeah.

Uh, so I'm very bullish on it. I think Josh obviously plays at at a very heavy economic level with his funds and that nature and everyone like him and others especially him I have so much pride in his building because he's done such a great job and New York City basin we were always like envious of best so it's been great to see his him thrive shine I think all anyone who does not realize how substantial the analog opportunities are is really missing the plot of what's happening and so it gets exciting it's exciting to think that you can invest and vote something that could get as big as, you know, anthropic in an extreme digital world. But also, forget about the obvious ones like the Giants or the Spear. I'm talking about people rolling up 900 local restaurants and building up a huge like like it it compounds 2x what anyone in PE would have thought because people want to go physically out and eat instead of just do seamless you know uh somebody buying up shopping malls not to make them data centers but because they think they can make a half experiential half old mall shopping environment that people are going to be yearning for. Um, here here's a left field one. Like uh the the drive-in movie theater, right? The stuff that dominated the 50s and 60s. When I say that out loud of like do you think a modern drive-in movie theater which has done really well and executed super well, do you think that a lot of people would be about that life? I think we can all agree that yes,

100%. Yeah.

And then what happens to the person that does 39 of those and has a real business and flips it? So I I think it's a really cool time for a lot of us that are watch this show where like oh crap we can play on either side of extreme digitalization or analog be creative.

Well yeah the beauty you know give the example of somebody making like a a modern chain of drive-in movie theaters is like you get all the benefits of AI still. You get to you get to use it for to instantly respond to any customer message and help solve problems.

Now we're nerding out. What if you have 40 of them and now this is seven years from now and you start showing your own films that you make in AI and build your own IP through your own analog distribution.

Yeah. Oh, that's a good thing.

I could see I could see doing that for kids, you know, like maybe slightly lower bar, but you create your own kind of kids kids content. That's again a lot of things I do. Yeah.

Get more obvious later. I got made fun of writing that book. Anyone can personal brand on Twitter. Now it doesn't look so funny. I mean,

who's laughing now? Who's laughing now?

Yeah.

But when I started building V friends and like building this Pokemon Sesame Street thing, yes, there was a lot of blockchain in it, but it was a lot of my smartest friends in Silicon Valley 5 years ago like this AI thing is percolating. you know, was a little more slang for machine learning and then it obviously got accelerated real quick, but like

yeah, I believe in a lot of this stuff.

Well, speaking of people that are watching the show, there is an army of people named Ryan in the chat and they want to be acknowledged by us. So, I'll ask you a question about a Ryan from your life. Can you tell me something you learned from Ryan Sirant or Ryan Holiday or maybe Ryan Harwood? Do any of these names conjure any interesting stories or life lessons?

Yeah, the Ryan Mafia is good. I mean, Ryan Hartwood I've learned nothing from. Zero. Absolutely nothing. So, I just put that on the desk.

Uh, you know, Ryan Holidayiday was definitely the individual that I was like, finally put a word to kind of how I was living my life, right? I my mother's my hero. She taught me just how to be a really happy human. You know, I thought it was immigrant and I thought it was simplicity and I thought it was, you know, love and health over everything and truly truly not just cliche [ __ ] but live your life that way. Even if you're an entrepreneur and a capitalist and want to compete, but when Ryan Holidayiday started talking about being a stoic and stom, I was like, "Oh, like, you know, like I was like, oh [ __ ] that sounds LIKE OH THAT THAT that's interesting." Yeah.

Um, and so I think that uh that's one for him. Uh, Siran, you know, was a fun one for me because a lot, you know, he's obviously playing at such a big personal brand level now and it was he had that TV show on Bravo and then it was off the air. You know, his curiosity and humility was amazing. Like he was always around our ecosystem and he really learned to play the playbook. I've lived, you've lived, he's lived so much of, you know, now he's back on Netflix, but he had a really great era in between his television moments of really winning on social and going all in. And I'm really proud of him. And Harwood is uh is just a dear actual friend. He's family, not a friend. And so I uh he's taught me that. Uh

I'm glad you c I'm glad you circled back because I was like, damn, he's taking shots.

You know, in you know, he's a Long Island boy. I'm a Jersey boy. I think anyone from our part of the world knows like taking shots to your brothers is like the ultimate form of I love you more than anything. I I think literally from from 1985 to 2000

98% of the words out of my best friend's mouths was highly disrespectful in my direction.

Of course, that's the best. That's the only way to do it. Uh Ryan Holidayiday wrote, "Trust me, I'm lying. Confessions of a media manipulator at 25. Should more young people write books? I talk to some brilliant young people every day on the show. A lot of them fantasize about writing a book, but it always feels like it's something that needs to come with wisdom, needs to come with being 40, 50, 60.

You get a lot of wisd but but part of it's like you're generating wisdom through writing, thinking deeply. Do you feel like

I I think of it this way, man. I think of it as weirdly back to my barbell. I think people that have something to say will probably be best at the barbell, you know, meaning it's kind of like someone's first album. You had your whole life to write it,

right?

Yeah. Yeah. And then so I don't know for me speaking for myself like again back to the books like when I look back at that I'm like how like and I'm pretty like kind of feel good about myself and we me and me have a good relationship with each other but even I like I look at it and I'm like how the hell did you write that in 2008 and then and then to your point I think my ne next best piece of work will be when I'm wrapping it up and I can synthesize all the good stuff. So, I would wildly encourage, especially the kind of characters you guys hang out with, they have a lot to say because much like I had in my youth, I saw things others couldn't see because I wasn't playing by yesterday's rules. I always say fresh eyes are dangerous eyes. You know, nothing. It makes you dangerous. You can really innovate. And then I think those people that, you know, have sustained careers and can have years of wisdom and chapters have a lot to say that can really wrap up and bring value. So, I I think most people, if they're going to be in that game, are probably going to write their best book first and last.

Uh, you partnered up with MasterClass.

Yeah.

Tell us about it.

Tell us about it.

You know, I 15 years ago, anything that looked like Masterclass, like selling stuff was really scammy. Like I grew up in the web 10 era and like I stayed away from a lot of subscription Patreon only fans master like selling information was really dirty in 9798 $150 ebook that was straight garbage. Yeah,

I I want to give Masterclass some flowers. Like when they first kind of hit the scene around that era, we were just getting into the earliest stage of where we are now where premium content, you know, Substack, Beehive, like now it now it's respected, which is amazing and I think is great for a lot of individual writers and contributors. Um, you know, it was really good company. Like I like who they had for this class. It's addressing something I believe is real, which is like getting an MBA in real life and AI at, you know, pennies versus taking on extreme debt and getting an MBA from a high class university that you think that logo is going to get you financial opportunity in a way that I believe has passed us by. Um, you know, just feels like I want to be part of things that are historically correct or, you know, are just a little more practical and common sense. And so, um, yeah, I mean, they've come to me a whole bunch of times. This was the first time I was like, you know what, I can join this crew. I have something to say about AI marketing and and production and and the strategies of that. And and I hope that, you know, me or Cuban or any of the other people they threw at it might get someone to stop and not take on $300,000 in debt that's not going to be ROI positive.

Yeah. uh what are you hearing from sort of like Fortune 500 CMOS uh like larger company marketers around how if anything they should change in the world of AI around their marketing mix?

Um giggling because we're going to wrap up here and I'm actually gonna

take your question but try to give an extraordinary amount of value to everyone that I know listens to this epic show. It's not what they're saying, it's how they're acting. Which leads me to the following sentence.

Everybody who's watching who's highly invested in big companies that spend a lot of money on marketing, your marketing department is wasting 93 cents of every dollar they spend.

Okay.

We are living in such a radical transformation of the midfunnel dominating not the upper funnel and the lower funnel.

Sure.

Us three right now are on midfunnel.

Yeah. We are producing content

born in the midfunnel.

I mean look I mean this is what's going on in my right this is a production day.

Yeah.

This will be post-p produced into creative that will go into midfunnel organic social. Yep.

And the things that do well will go up for brand and down for performance. Mhm.

Every brand on earth should be spending 20% of their entire marketing budget just on social media organic production because the midfunnel on Tik Tokification of social has eaten up the world and we should spend no media dollars

against creative that were guessing for the big campaign.

And then when I tell you every Fortune 5000 company is still doing guessing on the upper funnel, sponsorships, ridiculous [ __ ] And in the lower funnel, 2016 AB testing beta frameworks when the midfunnel ate up the whole world and you guys are winning, Bruins is winning and any personal brand and many other businesses.

And so that doesn't even get into the AI of it all. That to me is tooling and infrastructure to be great at what I just said.

Yeah.

Um but Jesus, there's a lot of money being wasted by the companies representing the eyeballs that are watching this show right now. That makes me sad.

Yeah, makes a lot of sense.

I I I can't stand

wasted marketing spend.

Yeah, blood makes my blood boil. Well, thank you so much for taking to come chat with us. Congrats.

We didn't even We barely got to talk about live commerce.

Yeah, there's a lot. We'll get that update next time.

Yeah, we you need everybody here. Anybody selling to the consumer needs to understand that China's going to do a trillion in GMV, a trillion in GMV this year in stuff sold

and and Tik Tok shop and whatnot are doing real numbers in in the US

and Meta's clearly going to be popping off any second with what they're going to do, which will lead YouTube to do what they're going to do. Sorry, I know you got to leave, but give me your 30 secondond outlook on Tik Tok post kind of acquisition change in ownership. How's the platform changing and what's your outlook?

There's I felt nothing. I haven't done any real homework on any like corporate structure. What is going to be the vibe?

I know, but will the new owner will the new owners be willing to like subsidize Tik Tok shop is kind of what I'm getting at.

Um, they they don't need to. It actually works on merit.

Okay.

You only need to subsidize shitty [ __ ]

Always a good time.

Thank you so much for coming on. We'll