Gary Vee Says the Smartest Investors Are Going Analog

Gary Vaynerchuk from VaynerMedia. Gary, how are you doing? Welcome back to the show.

Do you know about Wombos?

I do not, my friend.

You got to learn about Wombos.

You got to learn about Wombos. They are the next meta. They are the next meta. If you're not doing Wombos in 2026, you're getting left behind.

So Wombos are word combos. So the example would be, uh, a quiche is quirky and niche. You put it together and that's quiche. Or Lorraine. Lore plus explain.

That was a risky start for the first word.

Yeah, that's a risky one.

Lorraine is a better one. Give me if I say Lorraine.

Boys, first and foremost, congratulations.

Thank you.

Thank you.

I really mean that.

Thank you.

Thank you.

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 said go harder. We were already going pretty hard, but you said go harder. And we certainly did. So.

And go multiplatform. That was really huge too. 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 starts subpar, right? Like when you start working out or when you start singing or drawing, like, you know, like I, for everybody who's watching right now, every business, every personal brand, every B2B, every B2C, the— to not take advantage of the attention media landscape that's in place right now, um, it's really incomprehensible 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, multichannel, multi-format, the business outcomes can be extraordinary. And I'm happy to see you guys get one.

Yeah.

Thank you. Is it funny to you that 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.

And yet I wrote this book in 2008. It came out in '09, Crush It. In the back of the book, I talk about Ustream and live streaming. Yeah, I mean, you know, it ebbs 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 DJ framework that you guys executed in this genre.

Well, the, well, the interesting, the interesting thing is we've— there's, there's easily been 100, 100 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 surprised. I've been very confident. I've said this on podcasts for, you know, we've talked about this going back probably 6, 6 to 8 months ago. You should take this format of a livestream and you just add an 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. That's your set. You have a couple of cameras, so you have different angles, and then you just say, hey, every day at 3:00 PM, I'm gonna cook dinner. This is what I'm gonna 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 integrate guests into something like that too. So you have different conversations, 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 like, 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, GPT Images 2 launch where suddenly any brand, like basically fully democratized high quality product photography. Now there's still categories where like, I don't want you to AI generate 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 gonna 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 it used to be you could identify an entrepreneur's ability by their product photography in some way. 'Cause even if somebody's like bootstrapped 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 like a couple prompts away from it. And so it feels like it's gonna be harder than ever to stand out online.

Well, I mean, there's a lot there. I mean, It's— oh, we just got done talking about how hard it is to stand out online, right? Like, like, 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 incomprehensible to all of us that were born prior to 5 minutes ago, and This will be another transition. I think there's always going to be a timing game to this. Right? So right now, this open claw 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? And 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 their home, and other people were scared to because there was demons in it. Or, you know, the car, or 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, I, you know, look, this 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 scrappiness 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—

Totally. I, I've been thinking like, okay, you want to start an apparel brand, you want to go on Instagram or TikTok 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?

And my argument would be, and.

Yeah.

Right?

Yeah.

Like to me, this bar— like I just— extreme AI, I think, 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 could not be more interested in physical retail, in event-driven businesses, in concerts and venues. And I think the rise of analog— I have a restaurant business, 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. I like that. You see what's happening with flip phones. Gen 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 non-digital realities that are coming as a countermove to the insanity of AI advancements. We're literally within a half decade not believing a single video Not a single fucking video on the internet. Like, in 5 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 they hear that, I'm like, 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 of sales.

Yeah, they're effectively—

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. 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 coming back?

Are you and your— I mean, do you see my shelves here? Like, only thing I've been thinking about for the last 7, 8 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 counterpush to extreme digitalization.

[Speaker:JORDI HAYS] Sure. Yeah.

[Speaker:ADAM GRANT] 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, 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 go, this is kind of cool too. And like, it becomes behavioral. 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 sub pocket, 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 Brooklynites. And then we have that version everywhere in California, Texas, and Florida, and everywhere in the world. And so it's just, it's normal consumer behavior, but it is clearly a counterpoint to extreme in-feed, in-digital consumption. And I think that's great. It speaks to the thing I most believe in, which is humans correct themselves at a level that we are unbelievably underestimating. The sheer adaptability of the human race is extraordinary.

Let's give it up for us. 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 the Giants out of his new Eternal Fund, which is basically— 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 And then the 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. How are you thinking about both opportunities in new physical locations like the Sphere and then also in the, the, the more legacy brands like the San Francisco Giants, the New York Mets, the different sports franchises out there?

Yes. I, I, you know, it's really interesting to tie a couple things together. This distribution channel that you and I are on right now, right, the fact that people watching, yeah, in a way that 40 years ago somebody would have 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 this analog and not disrupted by AI thing, is why 6 or 7 years ago, I started investing very heavily in alternative sports. I made a big bet on pickleball that I think is going to work out quite well. Unrivaled, the 3-on-3 basketball league, AJ and I, my brother, early investors in that. The wiffleball league, the sailing league. Slam ball. I've been very aggressive on alternative sport investing, padel. I'm very bullish on it. I think Josh obviously plays at a very heavy economic level with his funds of 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. New York City-based, when we were always like, NBA is the best, Seth, so it's been great to see 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 in both 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 Sphere. I'm talking about people rolling up 900 local restaurants and building up a huge like, like 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, 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. Here's a left field one, like 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 think it's a really cool time for a lot of us that are watching this show. We're like, oh crap, we can play on either side of extreme digitalization or analog. Be creative.

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

What about this? Now we're nerding out. What if you have 40 of them and now this is 7 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 interesting.

Yeah, I could see doing that for kids, maybe slightly lower bar, but you create your own kind of kids' content.

Again, a lot of things I do get more obvious later. I got made fun of writing that book, Anyone Can Be a 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 VeeFriends and like building this Pokémon 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, it 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 Serhant 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 Harwood, I've learned nothing from. Zero. Absolutely nothing. So let's just put that on the desk. Uh, you know, Ryan Holiday was definitely the individual that I was like, finally put word to kind of how I was living my life, right? My mother's my hero. She taught me just how to be a really happy human. You know, I thought it was immigrants, and I thought it was simplicity, and I thought it was, you know, love and health over everything. And truly, truly, not just cliché bullshit, but live your life that way, even if you're an entrepreneur and a capitalist and want to compete. But when Ryan Holiday started talking about being a Stoic, and Stoics them. I was like, oh, like, you know, like, I was like, oh, shit, that sounds like— oh, that, that, that's interesting. Yeah. And so I think that that's one for him. Sirhan, you know, is 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— yeah, 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 Hartwood is, uh, is just a dear actual friend. He's family, not even friend. And so I, uh, he's taught me that, uh, I'm glad you cir—

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

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 think literally 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. Ryan Holiday 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.

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

I think of it this way, man. I think it is— it's 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 I don't feel good about myself. And we have— me and me have a good relationship with each other. But even I would— like, I look at it and I'm like, how the hell did you write that in 2008? And then to your point, I think my 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 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 1.0 era, and like, I stayed away from a lot of subscription— Patreon, OnlyFans, MasterClass— like, selling information was really dirty. In '97, '98, $150 ebook that was straight garbage. 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, BeHive, like, now it's respected, which is amazing. And I think is great for a lot of individual writers and contributors. 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 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. 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 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 production and the strategies of that. And I hope that 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. What are you hearing from sort of like Fortune 500 CMOs, like larger company marketers around how, if anything, they should change in the world of AI around their marketing mix?

I'm giggling 'cause we're gonna 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 is 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 mid-funnel dominating, not the upper funnel and the lower funnel. Sure. Us three right now, we're on mid-funnel.

Yeah.

We are producing content.

I was born in the mid-funnel.

I mean, look, I mean, this is what's going on in my room. I'm filming, right? This is a production day.

Yeah.

This will be post-produced into creative that will go in the mid-funnel organic social. And the things that do well will go up for brand and down for performance. Every brand on earth should be spending 20% of their entire marketing budget just on social media organic production because the mid-funnel TikTokification of social eaten up the world, that we should spend no media dollars against creative that we're 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 shit, and then the lower funnel, 2016 A/B testing beta frameworks, when the mid funnel ate up the whole world and you guys are winning, Ruins 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. But Jesus, there's a lot of money being wasted by the companies representing the eyeballs that are watching this show right now. And that makes me sad.

Yeah. Makes a lot of sense.

I can't stand—

Wasted marketing spend. Yeah, it makes my blood boil. Well, thank you so much for taking time to come chat with us.

Congratulations. We barely got to talk about live commerce.

Yeah, there's a lot.

We'll get that next time.

Yeah, we— you need everybody here. Anybody selling to the consumer needs to understand that China is going to do a trillion in GMV, a trillion in GMV this year in stuff sold. And TikTok Shop and Whatnot are doing real numbers 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-second outlook on TikTok 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.

But will the new owner— will the new owners be willing to like subsidize TikTok Shop is kind of what I'm getting at.

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

Okay.

You only need to subsidize shitty shit. Mm-hmm.

Ah, always a good time. Thank you so much for coming on the show.

Great to see you.

We'll talk to you soon, Gary. Goodbye. Uh, later in the show, we'll be telling you about a local man who grew a 900-pound pumpkin in his backyard and will tell you what it means for AI scaling laws. But up next we have Humble Robotics. The founder and CEO is in the waiting room. Let's bring in Eyal Cohen to the TVP and UltraDome. How are you doing?

What's going on?

Great.