Why Adaptability is Essential in Business

Summary

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The GaryVee Audio Experience

Episode: "Why Adaptability is Essential in Business"

Release Date: July 3, 2026

Host: Gary Vaynerchuk | Guest: Kurt Montgomery

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Episode Overview

In this dynamic and candid episode, Gary Vaynerchuk sits down with radio personality Kurt Montgomery for an intergenerational conversation about business, adaptability, and the ever-shifting landscape of technology and culture. With stories ranging from humble beginnings to insight on the future of media, Gary emphasizes why adaptability is the ultimate edge in business—and how those who resist change risk irrelevance. The conversation covers personal grit, the rise of digital (and a return to analog), social media's true impact, and predictions for emerging trends.

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Key Discussion Points & Insights

Early Signals and Adaptability

• Gary on Predicting Technological Shifts

  • He recalls immediately seeing the iPhone as a world-changing device—"the remote control of our lives"—and identifies those pivotal moments where adaptability shapes winners in business.
  • Quote [00:09]:

    "The day the iPhone came out... within an hour I'm like, okay, that was it." – Gary Vaynerchuk

• Adaptability over Nostalgia

  • Gary discusses the trap of clinging to outdated frameworks, whether in business or culture—“There is almost guaranteed defeat when you resist [change].”
  • Quote [30:11]:

    "There's just so much opportunity when you embrace change and there is almost guaranteed defeat when you resist it." – Gary Vaynerchuk

Humble Beginnings & Work Ethic

• Immigrant Story and Drive

  • Gary recounts growing up as an immigrant, coming from the USSR, and being “traded for wheat” in the late 70s—a humble start instilling gratitude and relentless work ethic.
  • He connects childhood hustle (lemonade stands, car washing, shoveling snow) directly to his confidence about financial success.
  • Quote [04:36]:

    “The United States traded wheat to the Soviet Union to let some people become refugees... We were part of that small group.” – Gary Vaynerchuk

• Family, Love, and Motivation

  • Both host and guest discuss the impact of a loving but financially strapped upbringing—how internal validation, not external, fuels unstoppable ambition.

Reframing Failure

• Failing Forward

  • Both reflect on failing frequently but using setbacks to learn, adapt, and iterate. Kurt highlights how people only see the “wins on the wall,” not the failures that outnumber them.
  • Quote [18:44]:

    "I have more fails. There's more L's in my chat than W's in my chat... All these fucking things, these darts [that missed]." – Kurt

• Gary’s Artistic Approach to Business

  • Compared entrepreneurship to being a creative in the studio:

    "I just want to cook up the next invention... I'm not scared to fail like a scientist..." – Gary Vaynerchuk [17:01]

Technology, Trends & the Next Big Things

• Technological Cycles & Pattern Recognition

  • Gary draws parallels between eras:
    • MTV in the 80s, social platforms like YouTube and TikTok, and the skepticism about new genres of music or tech (EDM, K-pop, AI, etc.).
    • Emphasizes pattern recognition and intuition: seeing nascent opportunities before others do.
  • Quote [25:46]:

    “So for me, YouTube was easy. I'm like, oh, this is television.” – Gary Vaynerchuk

• Embracing and Respecting Youth Culture

  • Not shaming new trends—"respect them first" to gain relevance and collaboration with younger generations.
  • Quote [28:03]:

    "The number one way to get the kids to respect or be interested in the shit we came up with is not by shitting on their shit, it's by trying to understand their shit." – Gary Vaynerchuk

Analog Revival & Digital Fatigue

• Return to “Analog” Experiences

  • Gary predicts the next wave in business will involve analog experiences—flip phones, vinyl, drive-in theaters—in response to digital overload and rising anxiety.
  • Quote [44:43]:

    “I'm thinking about starting a drive-in movie theater... We just are looking for different experiences.” – Gary Vaynerchuk

• Balance Between Digital and Human Touch

  • Suggests society will swing to extremes before finding balance. Predicts digital detoxes, community experiences, and new rituals (like putting away phones at restaurants) will gain popularity.

The Tools of Our Era: Social Media & Content

• Social Media: Tool or Weapon?

  • Gary compares social media to alcohol—we decide how to use it. The platforms themselves amplify our own tendencies.
  • Quote [47:41]:

    “I think of social media like alcohol... It's no different than a screwdriver or a hammer or a knife. It's how you use it.” – Gary Vaynerchuk

• Content is Everything

  • Content creation and attention are the currencies of this era.
  • Distribution always changes—books, TV, now social—so those who master new channels thrive.
  • Quote [53:05]:

    “The world is only about content... Content is life.” – Gary Vaynerchuk

• Algorithm Exposure: The Mirror Metaphor

  • The real impact of algorithms is that they “expose you” – your preferences, biases, and interests, not manipulate them.
  • Notable Exchange [61:05]:

    "We're me up. It's not China. They don't care about you. It's you." – Gary Vaynerchuk

Future-Pacing

• AI, New Devices, and Commerce

  • Predicts AI will become central, with some future generations even marrying AI.
  • Smartphones will be replaced by AR glasses within a decade; the digital/analog divide will spark new forms of commerce like live shopping.
  • Quote [55:26]:

    “When I tell you...the cell phone, the most important device in society right now, will look like an artifact.” – Gary Vaynerchuk

• E-Commerce Evolution

  • Highlights “live shopping” as the next wave, superseding static online stores with real-time, interactive video experiences.
  • Quote [65:06]:

    “Live shopping is going to change the way we know e-commerce... that sell on live shopping.” – Gary Vaynerchuk

Education, Jobs & Being Left Behind

• Adapting or Getting Left Behind
  • Those digging in their heels, resisting new tech, or relying on outdated education models will lose ground.
  • AI won't take jobs—people using AI will.
  • Quote [64:01]:

    “People that dig in their heels to yesterday... AI is not taking your job. Someone that uses AI is going to take your job.” – Gary Vaynerchuk

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Notable Quotes & Memorable Moments by Timestamp

• [00:09] “The day the iPhone came out... within an hour I'm like, okay, that was it.” – Gary
• [04:36] “The United States traded wheat to the Soviet Union to let some people become refugees... We were part of that small group.” – Gary
• [18:44] “I have more fails. There's more L's in my chat than W's in my chat...” – Kurt
• [30:11] “There's so much opportunity when you embrace change and there is almost guaranteed defeat when you resist it.” – Gary
• [44:43] “I'm thinking about starting a drive-in movie theater...” – Gary
• [47:41] “I think of social media like alcohol... It's how you use it.” – Gary
• [53:05] “The world is only about content... Content is life.” – Gary
• [55:26] “...the cell phone, the most important device in society right now, will look like an artifact.” – Gary
• [61:05] "We're me up. It's not China. They don't care about you. It's you." – Gary
• [64:01] “AI is not taking your job. Someone that uses AI is going to take your job.” – Gary
• [65:06] “Live shopping is going to change the way we know e-commerce...” – Gary

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Important Segments & Timestamps

• 0:09–1:21: Gary’s early vision for iPhone, why seeing patterns matters
• 3:40–8:45: Humble beginnings, work ethic, and internal validation
• 15:24–17:01: Mission-driven ambition and insular motivation
• 27:54–30:27: Adapting to technology shifts, advice for “old heads”
• 41:10–45:53: Analog revival, predictions for post-digital fatigue society
• 47:41–49:26: Social media as a tool—how to use, parental boundaries
• 53:05–55:26: Content as currency, historical perspective on distribution
• 64:01–64:59: Who gets left behind, the real threat of non-adaptation
• 65:01–65:57: Live shopping—the future of interactive commerce

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Closing Thoughts

GaryVee’s perspective boils down to a challenge: stay intellectually nimble, immune to nostalgia, and always observe what’s next. Whether it’s the shift from cash to tap-to-pay, TV to AR glasses, or static e-commerce to livestream retail, adaptability means survival—and thriving—in business. Those prepared to reinvent and empathetically embrace new generations’ values hold the keys to the future.

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Transcript

[Kurt]

What did you see early on with the Ubers and the Facebooks? And what did you see early on that others didn't see?

[Gary Vaynerchuk]

This I'm doing show and tell that this was about to become the remote control of our lives. What I. What I predicted for myself properly was when this was invented. And I would tell you, besides the day I saw the Internet and the day that I really played with ChatGPT, that first day when my brother AJ called me, the only other moment where I was like, oh, shit's really about to change was the day the iPhone came out. I went and got it, I turned it on, and within an hour I'm like, okay, that was it. Because, you know, and the kids, you don't know this up until that point. Yes, BlackBerry, but not the same way on your computer. The Internet was now on your. With you at all times, literally until that point. You could do some browsing on the BlackBerry, but it was janky. This was a screen that looked good. And I was on winelibrary.com and it was just like I was at home. And I realized that the iPhone was gonna change the world. And that meant everything that was building on top of it was gonna win. This is the GaryVee audio experience.

[Kurt]

Alrighty, big boy off air. I've been waiting on this one right here. Gary, Vee, my man. Welcome, brother.

[Gary Vaynerchuk]

Thank you for having me. It's a real pleasure.

[Kurt]

Okay, I'm gonna offer you some. Some dumb to start with, you know, so I can chew it and swallow.

[Gary Vaynerchuk]

You saw that, Gary.

[Kurt]

You really swallow all your gum, bro?

[Gary Vaynerchuk]

Every single piece. My sister's with me. She knows the real truth. I have swallowed 99 of every piece of gum I've ever chewed. And I chewed a lot of gum in the 80s.

[Kurt]

So the Mint isn't true.

[Gary Vaynerchuk]

What's that? The myth. I mean, I don't know what it's really doing, but so far I'm good.

[Kurt]

Well, let me tell you, man, if swallowing gum gets me in a position

[Gary Vaynerchuk]

that you start eating it.

[Kurt]

Oh, God, yeah. You're talking about. Yeah, but I really just wanted to sit down with you, man, because, for one, I'm a fan first. I really look at what you do.

[Gary Vaynerchuk]

Thank you, man.

[Kurt]

Not only do I look at it, I need to start applying it because it's different when you look at something.

[Gary Vaynerchuk]

Yeah, of course.

[Kurt]

Not applying it. And if you're not doing an execution, then that's a problem.

[Gary Vaynerchuk]

Yeah, I mean, you know, this, you know, let me give flowers back. You're such a true Legend of like the era that, you know, so many of us grew in, grew up in. And you know this, you've had so many of the artists and others that we admire come through, and the ones that came through only once versus the ones that came through multiple times. That word execution was a part of it.

[Ad]

Yes, sir.

[Gary Vaynerchuk]

Right. Both mentally and actually physically. And so I appreciate that. And you know, longevity is earned, you know, and I'm humbled by it. But again, you've been in the front row seat and you yourself have done it. You know, there's a lot of people have done your game as well. And to be relevant that long, you know, wasn't just luck or the great looks that we were gifted.

[Kurt]

Right, Right. Yeah. I take that. Obviously, besides chewing that gun, you need some fucking buns. But that's not what we're here for. Now there's a lot of beautiful, broke people.

[Gary Vaynerchuk]

Yes. That is facts.

[Kurt]

But you come from very humble beginnings.

[Gary Vaynerchuk]

Yes.

[Kurt]

And we've had a chance to kind of dive into that. And I come from humble beginners as well, bro. But yours, everybody have their story, for sure. And for those that probably don't know.

[Gary Vaynerchuk]

Yeah.

[Kurt]

Story, take me down that humble.

[Gary Vaynerchuk]

You know, I. I'm the byproduct of the American dream. I was born in the Soviet Union, the ussr. And for a lot of people, you know, I was a bad student except for history, but a lot of people struggle with their grades in history. When I was born in the ussr, it was like being born in North Korea today, like, you can't leave. So the odds were very stacked against me of where I started. Got very fortunate that my family was able to get out. In the late 70s, the USSR was running out of money and they were starting to sell people for. I was actually traded for wheat.

[Ad]

Wheat.

[Gary Vaynerchuk]

Cause the country was investing all of its money into weapons to keep up with the US and it was running out of money. You know, when people are scared of communism and socialism, there's a reason it hasn't worked in the last hundred years. And so we got out. Please.

[Kurt]

You say you were traded for wheat?

[Gary Vaynerchuk]

Wheat. The United States traded wheat to the Soviet Union to let some people become refugees to get out. And we were part of that small group of a couple hundred thousand. So from the get, I've been completely driven by gratitude because my odds are so unlikely. My family immigrated to Queens, New York, and that's where I spent the first couple years in the United States. And then we moved to Edison first. Dover, New Jersey.

[Kurt]

What is that like when you first get here, New York, and especially at that time, New York was a different, fast pace.

[Gary Vaynerchuk]

It was also a very tough era. New York City was bankrupt. It was. It was not pretty. I was very young. I was four or five years old when we were there.

[Kurt]

Those are sponge years.

[Gary Vaynerchuk]

They are. And I remember it pretty well. In fact, you know, it's a very. I look back on it very fondly because my great grandfather Shia, so my, my grandmother's father, my dad's grandfather, him and I spent a lot of time together at that time because my mom had just had my sister and she was obviously with me at all times. But when she was taking care of my baby sister, I remember going to the park with him. It's very funny. My whole life I felt like an old soul. And I wonder how much of that was DNA. And then I wonder how much of that was just my environment. Because I would spend a lot of time. My mom tells me stories that I don't remember, that I would go outside and I would go and like call all the 70 and 80 year old old men by their first name and speak Russian to them and chop it up with the old. The OGs, you know, and, you know, this, you know, and I thought it when I first walked in here. It ran through my mind, like coming up in anything. And then when you're in a position to be the og, there's a lot of wisdom, right, that we can spit on. The kids, you know, are they listening?

[Kurt]

Sometimes?

[Gary Vaynerchuk]

Yeah. Not always. You know, this. We were kids too, right?

[Kurt]

Definitely.

[Gary Vaynerchuk]

There was OGs trying to tell us shit that we thought we were too cool for, what have you. But I think I absorbed a lot of that, of that wisdom. And, you know, when you're young, you don't know any better. It wasn't that I knew that we were struggling. We lived very humbly. You know, this is studio apartment, one bedroom. You know, my sister's. My sister's like bassinet or whatever she sat in was literally a car seat that my cousin Bobby found in the trash. We come from real humble beginnings, but we were also fortunate. My father worked his face off. We moved to New Jersey first. Over then, we grew up in Edison, New Jersey, and we moved there in 82 when I was about to turn 7. And, you know, I'm straight out of like wonder years, right? Meaning like everybody outside playing sports, you know, I was always hustling from the beginning. Lemonade stand different, though, because there's a

[Kurt]

different kind of hustle muscle when you Come from very humble beginnings.

[Ad]

Yeah.

[Gary Vaynerchuk]

You know this. When you're not fed, you've got to go get your own food, you know. And so not only did we grow up with humble beginnings, but even when we went from poor to middle class, our mom was frugal. So we didn't. We didn't have, like, at some point. Old. When I was older, I was like, wait a minute. We kind of got somewhere, but we were still living as if we had nothing. Cause my mom didn't spend money on anything.

[Kurt]

Live like that a little bit.

[Gary Vaynerchuk]

Now I don't, and I do. Let me explain.

[Kurt]

I think someone would challenge that.

[Gary Vaynerchuk]

Yeah, yeah. Yes, I do. And I don't. Let me explain. I value time so much and have my whole life. I also genetically was given the gift of generosity. I also, from the time I was 10 or 11 years old, kind of knew that I would never have a money problem like that. Young. Even as a child, I'm like, oh, money's not going to be my problem.

[Kurt]

How did you know that?

[Gary Vaynerchuk]

Because I was making it.

[Kurt]

When did you first started making money? Because, you know, when you do a kind of a deep dive, and I don't like going into deep dive.

[Gary Vaynerchuk]

Yeah.

[Kurt]

I have these conversations. Right. But first job. How are you gonna learn?

[Gary Vaynerchuk]

I'm selling lemonade, I'm washing cars, I'm shoveling Snow. When I'm 7, 8, 9. Really early. Really early.

[Kurt]

Afraid of work. Not afraid to roll your sleeves up.

[Gary Vaynerchuk]

No.

[Kurt]

And not afraid to go out and get your own. No.

[Gary Vaynerchuk]

Our whole fam is work ethic oriented, you know, like, our parents had no choice. It came down to us. Like, you know, it's. In fact, it's put on a pedestal. In the household that I grew up in, there was a couple of things that were just unsaid or said, but working hard was kind of like oxygen, you know, it was like there was no other way to even think about it. There was really no choice. And then we also saw it. Our father worked every minute we, you know, every minute. We didn't see our dad when we were young, he was working and our mom worked her face off. She cooked every meal. She cleaned up after all of us. She, like, did everything. And so we didn't even know any. And again, when you grow up in a neighborhood where everyone's kind of working and it's just like everyone's working. It's like, you know, when we first moved to Edison, I would say it was lower middle class, you know, on its way to middle class. We had the wrong side of the tracks. A lot of, you know, we went to Martin Luther King elementary School. That's all y' all need to know, you know what I mean? Like, you know, we went to MLK

[Kurt]

down here in Beverly Hills.

[Ad]

Yeah.

[Gary Vaynerchuk]

You know, like we went to MLK and like there was, you know, we were far from living it up and there was people that had it worse than us. I don't know if you even remember this, but like Eric Godfrey's dad wore the same clothes every day. Like, like, like, like when I like humor his dad, you know. But like, like we had friends whose parent wore the same clothes every day. You don't think about it at the time. Cause it's your environment now. As I'm older, I'm like, and it, what I just said to her, I don't think I've ever even said to her, it's my sister off camera. Like things are coming clearer to me as I get older. And I'm like, it's, listen, if you were born, everybody who's watching this is something. I will die on this hill. If you were born into a family that does not have much pool table, doesn't have much by today's standards of everybody needs something but you have love in the home. You're fuck, you're unstoppable.

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[Gary Vaynerchuk]

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[Kurt]

Let me tell you, please, you know this. I'm from a family of eight, a single mom, seven kids.

[Gary Vaynerchuk]

And what number are you?

[Kurt]

I'm six. I'm second to the youngest and it's wild because I tell people the same thing. We didn't have money at all but we were very affluent in I love you and family bond and, and being tight, you know what I'm saying? And it's wild when I ask you, how did you know we had bouts of homelessness growing up, right. So. And it wasn't that my mom had any drug problems that she was.

[Gary Vaynerchuk]

She just had seven kids. It's a lot to take care of. Yeah.

[Kurt]

And you get into this slippery slope. So we had a couple bouts of homelessness, right? And I remember we were living in a motel, not a hotel, all eight of us in, you know, a standing motel. What, 395 square feet, 420 square feet, whatever that is, and we're living there. And I remember I told my mom, like how you say you knew money wasn't going to.

[Gary Vaynerchuk]

You knew.

[Kurt]

I always knew that I was going to be famous.

[Gary Vaynerchuk]

You just knew.

[Kurt]

Five years of age, eight. I used to write autographs to people and for some reason all my autographs said, best witches, best wishes.

[Gary Vaynerchuk]

Best.

[Kurt]

You know, to Gary, best wishes. Kurt.

[Gary Vaynerchuk]

Kurt Montgomery. Yeah, of course.

[Kurt]

And so I remember one time we were in the motel and I told my mom, I said, mama said one day. Because I always told people I was going to be famous. I said, one day, I want to be famous, I want to be rich and I want to buy you a house so we'll never be evicted and you never have to move again.

[Gary Vaynerchuk]

Yeah.

[Kurt]

And it's wild because even like what, like with you and your mom in the church, the New York Jazz Church, there's just some things that you.

[Gary Vaynerchuk]

It's real. No, it's just real.

[Kurt]

And so with me, when my mom, when I told her, mom, you know, one day I'm going to be rich, I'm going to buy you a house, we'll never be evicted again, she told me she could have said anything in the world, Gary. She said, I know you will now to a 10 year old key, everything. My mom could have said anything. She could have said, kurt, please, you know, yeah, of course I got to get this rent. Like, you know, she could have said anything that could have on a 10 year old's dream. So at that time, not that it was a burden or I had to, but I always had this drive that I got to do this for my mom. My mom worked hard. I never like what you saying that your parents worked hard. There was a lot of love. You probably didn't have to go outside

[Gary Vaynerchuk]

of your household for validation.

[Kurt]

Yeah, validation.

[Gary Vaynerchuk]

Ever.

[Kurt]

My mom was right there.

[Gary Vaynerchuk]

It's the toughest question that I get asked in interviews. They're like, which business? Like, what do you look up to? And I'm like, I hate it. Because there is no answer besides my parents. But when you say no. 1, you come off like you're audacious or you think you're special. And I know that most people. We had it and there's. And we had it, and that's why we're sitting here. When your role models are your parents, you're in a very advantageous position. Like, I just. I never needed validation from the outside world. Cause I had so much of it in my four walls. And it's really an unstoppable feeling. And when you.

[Kurt]

It's a different drive.

[Gary Vaynerchuk]

It's a different drive. And when you want to do it, you know, I was very motivated to do right by my parents my whole life. And clearly you were as well. And, you know, our stories are common. There's so many people. Like. It is one of the great stories in our society of the kid that says, mama, I'm going to buy you a home. It's like, you know, I'm in the sports business. My brother and I have a sports agency. And you know, a lot of athletes.

[Kurt]

You're in a lot.

[Gary Vaynerchuk]

I'm in a lot of businesses. I'm in a lot of businesses.

[Kurt]

I say dot, dot, dot. Like, oh, I do this, I do that.

[Gary Vaynerchuk]

It's another tough question, like, what do you do? I'm like a lot of things. A lot I'm juggling. Yeah, man, it's really great. And it's like, you know, it's so you just chopping it up like that. Reinforce it. I always like to hear the other versions. Cause it reinforces. Because you never want to be a focus group of one. One thing that I always promised myself when I started to realize, oh shit, I'm gonna be talking a lot in my life is like, never say anything. Just from my situation, observe everyone else's. What are the common themes? You know, because you wanna bring value to everybody on the other side of this camera. And I think a focus group of one is dangerous. Cause it might be too circumstantial. But what is very clear is if you grow up in that home, it makes you unstoppable.

[Kurt]

Did you know that and not. Did you know that early on? But is that. Did you take it as a burden or you took it as a mission?

[Gary Vaynerchuk]

I took it as a mission.

[Kurt]

Yeah. Same.

[Gary Vaynerchuk]

I took it as a mission. I, you know, probably a mission that

[Kurt]

you didn't know that you were. I knew I was on some kind of journey. But mission is probably a word that's like. But I knew that I wanted something different.

[Gary Vaynerchuk]

You know what's interesting with me is that. And you've got. You got me. I appreciate what you're doing right now. You're putting me down. An interesting. I opened an interesting door right now. That's why I'm kind of looking down. My game's interesting to me because my shit has always been. I'm gonna use a music reference because I admire you so much. My great joy is to just be in the studio. If I was a musician, y', all, I just like being in the studio. I never needed to prove to anyone. Yes, I wanted to make my family proud, but if I'm being incredibly raw, I just want to be in my kitchen cooking for me, with me, my game. I'm in a cocoon. It's just insular. I never needed to prove it to anyone that didn't believe in me. I just. It, yeah, came. That's where I'm a little different. A lot of people get to the top because they have energy that they need to prove something, often to their mom or dad, sometimes to others. Opposite sex. No girl liked me. I'm going to get rich and get all the girl. I didn't have any of that fuel for me. I just want to be in the studio and I want to do my art. I didn't have musical ability. I had entrepreneurial ability. For me, some of my best moments or just me with myself on a long flight. Sometimes even when I'm dreaming, I'm thinking, I can feel it. I just want to cook up the next invention. I want to execute it. I want to create my meal, all these ingredients, all this opportunity. And I'm not scared to fail like a scientist, right? When shit doesn't, I'm like, here it is, this potion. Watch this. And it doesn't work. That's almost equally as exciting as if it does work. I'm in it for my craft.

[Kurt]

I say the same thing, and people have it in different versions, very verse. But I always tell people they can look at certain things with me, right? And say, oh, certain things I do on radio. I love your phone tabs. Oh, I love this, I love that, right? And there's certain things that people will say, man, you're always winning. I'm like, no, not really. And I always tell people, I say, I have more fails. There's more L's in my chat than W's in my chat. I have way more feel because I threw so many things up against the wall. Now you could look at the wal and you Will see the things that stuck. But if you drop your eyes just a little bit, it's all these fucking things, these darts.

[Gary Vaynerchuk]

The other thing that you did, and I think we all do it because the world's been around for a while. Thing I always admired from afar that you did, is we all have our games and we're all playing in our lanes. But you have plenty of bells. I do as well. We all do. But the thing that I really like is that you were able to. And I think I do this as well and many others do. Is in your game, whether it was Z100 doing it in the. You know, like in New York or something you caught in dc. What I think the best players in the world today do is it's hard to invent something. You know, it's not like we're here in 1649 and we can invent it from the scratch. I think your iterations in your genre were authentically you and the audience can smell it, right?

[Kurt]

Yeah. When I first got hired, Gary, for one, Are you familiar with people called the Far side?

[Gary Vaynerchuk]

Of course.

[Kurt]

I was a bodyguard for the Far side.

[Gary Vaynerchuk]

I knew that as well.

[Kurt]

So before I got into radio, I was a bodyguard for the Far side. And that was just one of those things where I kind of stepped out on faith, even though I couldn't see the whole staircase. Of course, this is the opportunity that was presented to me. And at first, I wasn't going to take it literally. I had this hip hop line that if you called it, it was my way of getting into the clubs for free. You'll call it Tuesday night. Hey, Guadalaender is going on. You know, you'll call a regular line and I'll tell you about the club life. Someone heard that by the name of Rick Cummings and the Baker Boys, who did the morning show and Friday night flavors at Power106 in LA. They called and said, hey, you know, we got this guy that want to talk.

[Gary Vaynerchuk]

What year was this?

[Kurt]

This is 1994. This year, Memorial Day would be 33. By closing on my 32nd year, closing my 33rd. It was supposed to be one night. And it was just one of those things, man, where I got in and I said, I gotta.

[Gary Vaynerchuk]

And you tasted it the first night? Yeah.

[Kurt]

And when I. Then the second night, he called me back, said, would you like to try for another night? And I'm thinking $35 an hour times four, because I'm ready to go on Lollapalooza tour with Far side and Wu Tang and All this stuff, right? And I said, well, let me just try. I stepped out on fate, even if I couldn't see it.

[Gary Vaynerchuk]

And you knew it. You knew it. It's just something that, by the way, I lived it. A few months later, ironically, just talking about hip hop, I went into my friend Big Dave's. He was from Staten island, so he was banging Wu Tang all day back then. And in that moment in that dorm room was the first time I saw the Internet. And the first. Just like you felt. You know, it's like I always say this. It's like there's sharks in the world, and you give a shark one bleep of blood from a mile away, and they're shooting at it. You felt that that night you were on. You're like, right, Same for me on the Internet, literally. I didn't grow up with computer. Like, we. I didn't. We didn't grow up that way. Like, I'd never been on the Internet. And I was on the Internet in 94 in that dorm room. And in one second, and I mean one second, I'm like, this is it.

[Kurt]

And whose dorm were you in?

[Gary Vaynerchuk]

Big Dave's.

[Kurt]

Where's Big Dave at?

[Gary Vaynerchuk]

I don't know. But Big Dave, I know this is a good story for you. And it was. It was actually. It wasn't even big. It was Big Dave's room. Cause he was the alpha of the room. They had four roommates. It was actually Pete from Maine who had the computer with the Internet on it. And it just completely. I just knew. And I know what you're saying. When you were on that night, by the way. That's what happened to me. The first time I took the stage, I was 31 years old. The first time I ever gave a public speech.

[Kurt]

Were you a public speaker?

[Gary Vaynerchuk]

No, I was a wine retailer. And then I started this wine show on the Internet. And then I started making business content.

[Kurt]

You see the wine show, like, he's like, I started this one, you know, but that. That's very innovative.

[Gary Vaynerchuk]

Yeah, I mean, I. I started a YouTube show 20 years ago February. A daily YouTube show.

[Kurt]

What made you understand that I'm gonna

[Gary Vaynerchuk]

use music as my comp? Given your incredible career, I, by nature, am an A and R. Hey, everybody. Hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy. I, by nature, when I see things happening in society, I'm like that.

[Kurt]

That.

[Gary Vaynerchuk]

Yeah, just like the best A&Rs of all time. You know, I watched the documentaries and the music stuff. I always loved the A and R's. Like, I went into this dive bar and I saw fucking, you know, Motley Crue. And I knew it. And I'm like, fuck. I understand that feeling. Cause that's how I feel about TikTok or live shopping or the Internet or YouTube. I understand. And by the way, you might know this. Cause this is what you do. Like, whether it was Gunna or Dochi. Like, I do it in music sometimes too. Cause it's all the same game. I don't think I have the same ear in music that I do in technology and. And consumer behavior. But it's all the same game. Like, you know, it's all the same game. It's like, do you feel and do you understand where things are going? And with YouTube, it was very simple. I was doing Internet stuff, selling wine on the Internet. And then this YouTube thing hit and it was video on the Internet. It wasn't complicated, people.

[Kurt]

It sounds genius now because when we look in the rearview mirror, everything sounds genius. But when you're looking through the windshield, you know, that's like different kind of shit.

[Gary Vaynerchuk]

But you know what's funny? I. I look at pop culture historically. I think about MTV all the time. All the time. Right. So I don't know if you all know this. Who are watching. Many of the biggest acts in music in the early 80s said no to making a music video for MTV because they thought they were giving away their music for free.

[Kurt]

Yes.

[Gary Vaynerchuk]

You know this. So they thought it was giving away their music for free. What the Princes and Madonnas and Michael Jacksons and Twisted Sister and Duran Duran understood was. It was free promotion. So life is simple. You find what you're looking for. This is why so many people eventually get money and then go on defense. So many people go from zero and get to a level and then they stop because they're scared to lose it instead of realizing it's the foundation to build on top of it. So for me, YouTube was easy. I'm like, oh, this is television.

[Kurt]

Who was watching?

[Gary Vaynerchuk]

No one, right? No one.

[Ad]

But.

[Gary Vaynerchuk]

But again, let's just use like, you know, obviously.

[Kurt]

But you knew something.

[Gary Vaynerchuk]

Yes.

[Kurt]

Was there.

[Gary Vaynerchuk]

But it goes back to like, you know, my favorite music genre that you touch on a lot, Hip hop. No one was listening. And then. And eventually everyone was listening. Everything has to start at something. I always laugh when the rock again, going back to history, all those rock and roll. People that were shitting on hip hop. I always laugh cause I'm like, but rock and roll was new too. It wasn't like when rock and roll hit all the jazz people were like that's bullshit, not music. And by the way, you know when edm, when that started popping, I watched my hip hop friends saying that's bullshit. I'm like don't do that, don't do that. You know, you see it now with Korean pop or reggaeton, like, like, like shit's always going to be moving. And as the great poet said, never get high in your own supply. And so I, I, a lot of people interpret Biggie's line a lot of different ways. My point of view is whatever makes you money might be the vulnerability of the next chapter. And too many people get locked in. Like our era, we may shit on mumble rap, but the kids like it. And so like who are we?

[Kurt]

Yeah, you understand because I know my radar. I have a 19 year old son and I have a 17 year old daughter. So I use them a lot for radar of course.

[Gary Vaynerchuk]

And it's the greatest, it's the reason to have kids 100.

[Kurt]

Thank you for adding to my career. Career now pay me back. But yeah, so I always kind of check the radar. When I first got into radio, Gary, like if I had been, I always used to say I'm on change resistant. I'm change resistant. But I know how to change. When I first got into radio, my first commercial was on reel to real. I suppose I'm playing albums and I'm playing CDs and carts. And that world started to evolve.

[Gary Vaynerchuk]

Can become digital and you can fight

[Kurt]

it, but the more you fight it and the way that we see things now, some people are fighting.

[Gary Vaynerchuk]

I tell the old heads all the time the number one way to get the kids to respect or be interested in the shit we came up with is not by shitting on their shit, it's by trying to understand their shit which then you'll get respect if you respect them first. And then you can introduce Big Daddy Kane to a kid that's all about, you know, the Migos at the time.

[Kurt]

I remember never given a history lesson, I said oh, that's just not music.

[Gary Vaynerchuk]

It's crazy.

[Kurt]

They don't want to hear that. Of course they see that. Even more so because now things are going even fast. So fast to make you a dinosaur. I remember sitting in the station and talking about AI and it felt like we went from zero to a billion in a heartbeat. And now I question everything I look at.

[Gary Vaynerchuk]

Well, I question every year, every single person in three years will not believe a single thing on the Internet. That's a crazy concept that is going to be foreign to all of us. But again, back to music. I was there on day one Napster, and that was crazy. Like, again, bunch of kids in here, you have no idea what it felt like to, to be like yesterday. The only way you would have access to music is if you went to the fucking mall and bought the CD or your friend had it. And now you press a couple of buttons and you have it. You didn't even fucking understand.

[Kurt]

And it felt like it would just like it appeared.

[Gary Vaynerchuk]

It always does. Yeah, it always does. But you know this. It feels at the moment that it appeared, but then when you understand it and look back, it was a step of a million little things. And then. And the question becomes, when do you find goes back to people A and rs? You know how people like hate on the band that they loved when no one knew them, right? That's such a cliche thing. You loved it when no one knew. Now they're, you know, when they were a dive bar band or somebody, you loved them. Now that they're selling out, you know, arenas, you hate them, they sold out. You know, I, I just don't understand that framework. I understand why people do it. But the reality is, is that there's just so much opportunity when you embrace change. And there is almost guaranteed defeat when you resist it.

[Kurt]

Have you always been that guy?

[Gary Vaynerchuk]

Yeah, because something. And I finally have a good analogy for it. I use Star wars for it. Like, and I use like the jungle. Like, Like, I feel like if you love the jungle, you can't just love it when you're a young lion and you're killing everyone. If you actually love the jungle, then you have to be prepared to be an old lion and let the young lion kill you. I love entrepreneurship so much that it has been the foundation of what has built my life. But I'm equally prepared for it to kill me. If AI is the technology that kills me, I'm okay with that. Because you can't love the game. This is why I fuck with athletes. Athletes go from being like watching LeBron right now is so poetic for me. He's still crazy. He's still doing shit that makes no fucking sense. But like going OG like I remember when Kareem was getting older or when Larry Bird's back went out, or even Kobe, even though ain't crazy in his last game, rip like What I love about sports is even the best you can watch in your eyes deteriorate. And we all see it in life. Too many people try to hold on. What they do is they start to demonize and shit on the game that built them everything, right? So how could you be a hip hop head that grew up in the era when we had the Fat Boys and Beastie Boys and you know, all this crazy shit when everyone was shitting on it and you had to live just for yo, MTV Raps and now it's the biggest genre in the world. Well, if you grew up with that and you benefited from it, you can't shit on K Pop or on a new version of hip hop because then you're disrespecting the game that put you on. And so for me, I've always been that guy. And I'm even more of that guy than I realized. Because when I got older, five, ten years ago, and I said, wait a minute, you got all these people that love entrepreneurship and capitalism in the game. But then I started to meet the 70 and 80 year olds that were ahead of me and I was like, wait a minute, they're using their money to pay off politicians to keep their money. I'm like, that's cheating. I'm like, that ain't the game. You're not good enough to compete with me anymore. So you want to change the rules of entrepreneurship because you're the old lion and you don't have that 19 hours a day energy in the summer. You want to be in Ibiza and Santa Tropez on your yacht while I'm in the fucking office cooking. The fuck are you trying to change the rules for? And I promised myself I would never become that guy and I will not be that guy. And I'm not that guy right now. And when I watch people on the come up that make content that gets more views than me, that start companies that are bigger than me, I don't have jealousy or envy. I have fucking hat tip and respect.

[Kurt]

I get the same thing when I look at certain, like even podcasters, I'll look at it. And at one point people used to say, oh, podcasting, man, that's the graveyard. Podcasters used to be people that so called couldn't get a radio job.

[Gary Vaynerchuk]

That's right.

[Kurt]

Oh, they can't get a radio job.

[Gary Vaynerchuk]

That's exactly right.

[Kurt]

Now you look at podcasters and you look at content creators or you look at influencers, whatever those may be, and they're running the game and I can sit here and say, man, I've been in here 32 years and there's some people that's lapping me. But I look at what my next moves are, that part, and what I'm going to do that part, you know, for longevity or even to walk out the way that I want to walk out that part. But there's so many more opportunities.

[Gary Vaynerchuk]

In 08, when I wrote Crush it, my argument was that the influencers, there wasn't a word for it at the time that the Internet people were going to win. And I got so much shit from my Hollywood. I used to come here and they're like, that's so stupid. This is Hollywood. And they were like, movie stars, TV stars. And I'm like, your history. You don't understand your history. When the television was invented, if you had a TV show, you were lesser than the radio. The radio was the fucking apec. You were lesser than like, how about the silver screen movies? You know, we're of the age where a movie star now, now if you're a star on a Netflix show, fuck that. If you're with Kaiser, if you're a streamer on Twitch or Kick, you're more famous than fucking starring in a feature film. Distribution changes. Fame changes. When before us, if you were a pilot, an airplane pilot, you were famous as fuck. If you were a pilot. Do you know that athletes, professional baseball players for the Yankees in the 50s would get jobs in hardware stores in the off season because that's how little they got paid. Fame changes. Shit changes. That's just the way it is. How about chefs? When we were kids, if you were a. If, what do you do for a living? I'm a chef. Oh, you're the help, right?

[Kurt]

Right.

[Gary Vaynerchuk]

Right now you're fucking famous as. So I, I don't understand how people don't understand that Shit changes. And you're more than welcome to hold on to your romance, say that you're keeping it real, that you're an og, you can say what the fuck you want, but the market doesn't give a about your opinions grounded in, in your self interest, my man. The market does not give a fuck about you holding your opinions based on your self interest.

[Kurt]

What did you see early on with the Ubers and the Facebooks and what did you see early on that others didn't see?

[Gary Vaynerchuk]

This, I'm. I'm doing show and tell. That this was about to become the remote control of our lives. What I, what I predicted for myself properly was when this was invented. And I would tell you besides the day I saw the Internet and the day that I really played with chat GPT that first day when my brother AJ called me, the only other moment where I was like, oh, shit's really about to change was the day the iPhone came out. I went and got it, I turned it on, and within an hour I'm like, okay, that was it. Because, you know, and the kids, you don't know this up until that point. Yes, BlackBerry, but not the same way on your computer. The Internet was now on your. With you at all times. Like literally until that point. You could do some browsing on the BlackBerry, but it was janky. This was a screen that looked good. And I was on ylibrary.com and. And it was just like I was at home. And I realized that the iPhone was gonna change the world. And that meant everything that was building on top of it was gonna win. So I didn't know Facebook or Uber or Instagram or Snapchat or TikTok, but I knew that the platform, whoever was winning there, was really gonna win. And again, it seems crazy to say now, but at the time a lot of people thought the iPhone was going to be a flop.

[Kurt]

Remember what year was that?

[Gary Vaynerchuk]

What year was that? Can someone look at. It was. Oh, hold on, I'm going to guess 2000. Before you say ma, let me get. You said it 0908. Yeah, it was, it was after Wine Library TV, but before I started Vayner 7. That's what I thought. Yeah. Yeah. So that was a monumental day. That was a big bet. And then I just. You could just feel, you know, I was in the game since 96 people,

[Kurt]

that this is a game changer.

[Gary Vaynerchuk]

Yeah, but those people at the time were like my sister and my dad, like nine people. I had no platform to tell anyone anything, even friends.

[Kurt]

Did anybody think, like, you were crazy?

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[Gary Vaynerchuk]

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[Gary Vaynerchuk]

I, at that point in my life, I think I was creating enough success. I think When I launched winelibrary.com in 1997, people thought I was crazy. When I told people that people were gonna buy wine on the Internet. My father's friends that were in the liquor business. This is crazy. I'm excited. There's some kids here. Here was the normal conversation for me in 2007, yo, I'm gonna launch this website, you know, the Internet, World Wide Web. We didn't call it the Internet yet. The World Wide Web. I'm gonna put dad's store on it, and we're gonna sell wine on it. And literally, the liquor salesman and the people I knew would say things like, why would I buy it on the web? I'll just go to the store. It was just like, not in people's

[Kurt]

heads at that time. That is a very realistic question.

[Gary Vaynerchuk]

Well, let me give you one right now. I believe some of the kids in here, grandkids are gonna marry an AI robot. I believe there are people in this room right now whose grandkids are gonna marry. Marry their significant other in life is going to be an AI robot. Thoughts, right? So like, she said, that's Ani. An is ready. She's like, ready.

[Kurt]

Ana can do another hour with you,

[Gary Vaynerchuk]

you know, so you know, to me, when I said, I'm gonna sell wine on the world wide Web, it seemed foreign right now. I said this, and people might giggle, people might fuck that. But, like, for real, though, you know, as if we don't have enough problems with race and religion marriages. You think it's been tough with race and religion, Wait till your granddaughter brings home 887494. This is my husband. You know, like, like, shit's about. And that's just the way it is

[Kurt]

because I love my wife, right?

[Gary Vaynerchuk]

Yes.

[Kurt]

Oh, my God. Always. Sometimes I did have a robot. And the reason why I say that, because I could tell my wife, like, oh, baby, you know, yeah, I'll see you with the robot tonight, bro.

[Gary Vaynerchuk]

Some real shit, though. Like, people, like, giggle now because it seems so. But we're not going to be giggling in 25 years, and we're going to be dealing with that. You know, people don't, like, change. It's why people struggle with race and religion. People don't understand, don't have enough empathy, compassion, sympathy for something different people are not ready for their child to be dating a robot and it's going to happen.

[Kurt]

And you know what's great? People could probably look at this and if we put this in a vault to people say, oh, they were right on point, 100%. And think about it. I remember when people said, oh, we're going to have electric cars. I'm like, electric cars. Because the Jetsons, everything that I saw in the Jetsons, I'm living now. Food being cooked, talking to people.

[Gary Vaynerchuk]

Let me use that bar to set up another convo that I hope helps people listening. We're now going into full Jetsons and I think one of the biggest opportunities in the world is to go Flintstones like go back. Let me explain. I believe we're in a very interesting moment, which is why I'm putting it on wax right now. Because I think I'm going to be very right about the next decade. We are about to go into an extreme digital. This AI thing hasn't even started cooking, friends. This hasn't even started cooking. Because of that, I'm seeing analog explode. Gen Alpha. The under 15 year olds are the first crew that are like, nah. Did you see, did you all see this weekend? All the commencement speeches at college and anybody that brought up AI, all the kids booed, booed.

[Kurt]

You saw that Arizona. What was the Schmidt?

[Gary Vaynerchuk]

Yeah, Eric Schmidt from Google.

[Kurt]

Oh my.

[Gary Vaynerchuk]

So 15 years ago when any of the tech people went to these colleges and talked about the new technology, social, mobile, all that, they got cheered. They were the heroes. This is because people are starting to struggle with how much digital there is. People are anxious. So I think some of the biggest opportunities in business. This is the only reason I'm saying it. Hopefully somebody runs with it.

[Kurt]

Let's not say it.

[Gary Vaynerchuk]

No, no, no, give me a chance. But you know what? If you know this, it's all execution. I'm, I'm ready for this. I'm about to say it. None of you are going to do anything about it. Do you? People ask me all the time why I give away all my best stuff. I'm like, cuz no one's going to do.

[Kurt]

You're not going to use it.

[Gary Vaynerchuk]

No one's going to do. You ain't doing. You'll be like, yeah, yeah. But people don't do. Anyway, before I got on that rat. Back to this analog. This was this, this was the holiday season that the Most kids under 15 asked for flip phones, not smartphones. If literally 12 year olds, 13 year olds, if you have nieces Nephew kids you'll know. Others don't if they don't have a kid in that age. You're starting to see that crew ask for stuff.

[Kurt]

My daughters, she asked for like film cameras, Polaroids, like things like that.

[Gary Vaynerchuk]

Vinyl.

[Kurt]

Yes. You saw she got vinyl, she got a turntable.

[Gary Vaynerchuk]

People are starting to really check out. I think you're gonna start seeing like I think there's gonna be a digital detox. I think much like Shabbat, like Friday, I think there's gonna be one day a week where people completely. It's gonna happen. Cause there's just so much and we're humans, we adapt. For example. Let me give you an example. I'm just gonna share one of my best business ideas that I'm thinking through. I'm thinking about starting a drive in movie theater.

[Kurt]

Yeah, I would.

[Gary Vaynerchuk]

And you see, you see, right? Look at the reaction. Like we just are looking for different experiences. I have a restaurant group that I'm very proud of that's doing very well. I'm not the act, I'm a partner, but I'm not the operator day to day. But I'm pitching my partners to open a new restaurant where when you walk into the restaurant you have to put your cell phone into a locker and the tables are community tables. People are just start, uh huh. I just see it, I see it, I see it, I smell it. And I think it's gonna be wonderful. But it's gonna be both. While we check out for a day and while we go to drive in movie theaters, we're also gonna be so digitaled out, everyone here is gonna have an open claw running 45 different agentic AI agents shopping for them and analyzing. Like we're going into this very extreme world. And I think I'm actually very optimistic about this. I think as we pull very digital and we start the beginnings of pulling very analog in there. Just like a bridge is going to come some strength and we're going to reconcile and in our extremes we're going to find balance. And I'm excited about it.

[Ad]

I hope so.

[Kurt]

Is a high gifting a curse?

[Gary Vaynerchuk]

Of course. Everything is, everything's a gift and a curse. Every big technology, the Internet was a gift and a curse. Like by the way, electricity, you know, was demonized when it first came out. Like of course. And people are going to lose their jobs.

[Kurt]

Atomic bomb.

[Gary Vaynerchuk]

Yeah. When the atomic bomb came out, everyone thought it was the end of civilization. We found. Why do you think America and China are chummy chummy? Because they both have it it's like a fight. Like, you know, notice, like, when both people have a gun, everyone's like, all right, chill, chill, chill. Right, like, right, because. Because, right, like, everyone's laughing. That's been around in a little bit. When somebody has one thing and the other doesn't, shit goes bad. When only one person has a knife and the other one just has their fists, it's a problem. But when both people pull out a fucking gat, everyone's like, chill, chill. And that's what happened. And at the time when the atomic bomb was dropped in Japan in the 40s, nobody would have guessed. If I sat here on video and said, let me tell you what 70 years from now is gonna look like. 12 countries are gonna have an atomic bomb. Who would have ever guessed it would have never been dropped again? It's because it's balance. It's balance. And I just think that that's what's about to happen. Everyone's scared. Everyone's all fucked up. I already see anal, and I think analog is going to. You see what's happening with music festivals, sporting events, they're all popping off more and more and more. And so I think we're going to get to this extreme place. And then you as a human can decide when you want to go crazy digital or when you want to go analog. And that, I think, is going to be a very good societal moment.

[Kurt]

Talk to me about what you've learned and what we're missing when it comes to social media.

[Gary Vaynerchuk]

That it's like, it's a weapon, it's a tool, but you have to know how to use it. I think of social media like alcohol, so everyone's all fucking mad at social media right now. I don't know if you know this, kids, but alcohol was banned in America for a period of time. It was called prohibition. We decided that alcohol was so bad that we had to ban it in America. Banned that shit didn't work because humans are humans and we're going to find our way. And it created the rise of organized crime and all sorts of up. There was all sorts of that got up because of it. It's no different than a screwdriver or a hammer or a knife. It's how you use it. What I know about social media is, is it is one of the greatest tools for good. If you have loved to share with the world, you have a platform that is free and you can literally reach the whole world on the flip. If you've got hate and negativity, you can do the Same. But what I've learned about social media is it's the great exposure of human beings. If you want to point to it and say it fucked up everything, well then you got to start thinking about this. It fucked up everything for you. And you've decided that. And so how you use it if you don't know, for example, parents always come at me like, Gary Vee, though it's fucking up the kids. I'm like, good, be a parent. If you think social media fucks up your kids and you're a parent and you have a 12 year old, then fucking man up and be a dad and take it off their phone. I have a funny right, like, right.

[Kurt]

And the reason why that hit me different is because I have a daughter and my daughter has anxiety. And I always said, man, we didn't get her that phone. But then there's times I'm like, we got her the phone, you know, and. And by the way, I'm like, oh, you know, we got to put our phone. Because I find myself on the device way more.

[Gary Vaynerchuk]

It's discipline. Like again, sitting around and saying alcohol fucked everything up versus my relationship with alcohol. And by the way, for every parent that's watching, people had anxiety before the Internet, right? We used to cover it up. Everyone's like, what's going on with like depression and suicide. I'm like, let me tell you how depression and suicide were handled in 1939, in 1954, in 1962, when your uncle committed suicide, you all thought he had a heart attack,

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bro.

[Gary Vaynerchuk]

Shit doesn't change as much as people think. What people don't understand is the world has been cons.

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What?

[Gary Vaynerchuk]

You know, like, like people used to cover shit up. People used to cover shit up. My guy. Like, it's just the world change now everyone's sharing everything, which is fine. But like, we didn't just get Anxi. I love how people are like, there's so much anxiety. You know what was anxious when you were a kid in 1954 in America and you had to do an atomic bomb drill in class every day in case there's an atomic bomb go underneath your desk. You don't think that gave. Could you? Yeah, exactly. You imagine being 11 years old and being in class and you have to do a drill, not a fire drill. You had to go under your desk. There's also other things. Kids go to school now and worry about having a school shooting. You don't think that's adding to stress? There's just, we are so one dimensional. We Always blame the new thing in a world where we're way more in control than people realize. The big issue, my guy, is that these politicians got everyone believing that you're not in control on both sides. Friends, I'm just going to take a public service announcement. You have to listen for a second. They're both doing the same thing. Be scared of this, and I can help you. Be scared of this, but I can help you. Be scared of the billionaires, I can help you. Be scared of the immigrants, but I can help you. That, my friend, is the problem. These politicians have everyone thinking they can help. Meanwhile, I'm always putting out content, saying the truth, love, not hate, which is the following. Yo, y', all, I can't help you. You can help you. And that is where we're at right now, my man.

[Kurt]

You say you put out content?

[Gary Vaynerchuk]

Yes, sir.

[Kurt]

How important is content? Because I'm in a content war.

[Gary Vaynerchuk]

Yes.

[Kurt]

Wow. Because I remember when you waited for a commercial to come on TV or you waited for a trader to show in the theater.

[Ad]

Yes.

[Kurt]

Even when you think about the super bowl, people pay for super bowl ads for prestige, the 6 million, $8 million. But I see the super bowl commercial in my phone and the 30 seconds that they could play on the TV, there's probably a minute, minute and a half that they'll release on social media. I get everything from social media or right there on my screen. How important do you feel that is? That you can go directly to the consumer?

[Gary Vaynerchuk]

Now, to answer your first question, the world is only about content. When the printing press was invented, content, the printing press. We now have books. Before we did it. Now we do. The first institutions to print the most books were religious institutions. Today, all these years later, the world is highly based on religion because the religious institutions were first to move on the printing press. The world is content. There is nothing else. Before then, it was stories around the campfire, the philosophers that were under a fucking tree. And you go see fucking the philosopher and chop it up. This is what it's always been. So content is life. It is even your family's stories. Everything is content. It's how humans live. Where content is relevant, how content gets distributed, which is what you're talking about. That shit changes forever. That will always change. You know, back in the day, you would have to go to a wall and carve it. I got one. Here's my favorite one. Do you know that when the canvas for art was invented that the word on the street was, that's not real art. Real art is Only when it's etched into buildings. So you know what's real. What's this like, you know, Distribution will change forever, my man. Distribution of content will change forever. There will be a day where the Internet is not the primary source of distribution. I for sure don't know what it's going to be, but I know that nothing lasts forever. I know that it changed. I'll give you one that I know is coming. This. This is coming. This is gonna look just like a beeper and a. And a pager one day. This. The glasses, bro. The glasses are coming and they're going to completely change

[Kurt]

now.

[Gary Vaynerchuk]

No, no, it's gonna be AR at first with a mix of VR, but, like, the glasses are coming. It's so obvious. It might be six to nine years, but when I tell you we will clip this and post it in 15 years, the phone, the cell phone, the most important device in society right now, will look like an artifact.

[Kurt]

What do you feel when you say the glasses? Like, what are we.

[Gary Vaynerchuk]

So I. I've worn some of the glasses that are coming in years to come. I don't even know how to explain it. It's so crazy. It's so intuitive. The one version that I played it, you have a wristband. Facebook has put this out. Orion. It's just so intuitive. It's kind of like the phone. You just know, like, you're not going to need the phone. Like, it's all going to be there. Voice, the audio. Even now, the basic Facebook glasses, the meta glasses. The audio is crazy. It's better than the AirPods. I don't know how many of you have worn the Meta glasses, but if you listen to music right now, forget about six years from now, if you're into music, go get an AirPods pair of the latest Meta, Ray Ban or Oakley or whatever they got out there glasses and put music on it. It's better than AirPods right now. So you see the screen, you see everything. I played Pong in the beta test that I did. I played Pong with a guy that was in Japan or China. I don't remember. It said, call Ray. He showed up, I'm wearing glasses, and he's like, you ready to play? I'm like, yeah. And he goes, bloop. And then I go, bloop. And it was, like, dramatically more entertaining than 90% of the things I do now. Like, it's just here. And again, when people hear me talk about this and be like, nah, this, I remind them, if your great grandparent saw what the world looked like right now. They'd be like, what the fuck happened? Shit changes. It's just the way it is.

[Kurt]

I want to zoom through some of these, please. I saw when you said the no. 1 asset in the world is teach.

[Gary Vaynerchuk]

What else is there, right? Can't change the world if no one's listening. When Martin Luther King gave that speech, do you see how many were on the lawn, let alone television, airing it? Let me ask you a question. If MLK gave that speech in the woods and no one was there, what the do you think would have happened? Nothing. Attention is when you're teaching your child to be a better person, when you're sitting with them and teaching them a life lesson. The framework of attention dictates everything. It is the number one asset.

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[Kurt]

It's no longer social media. Interest media.

[Gary Vaynerchuk]

Everybody who's watching knows this. Fifteen years ago, you would get content from the people you followed. Now, if I open up everyone's phone, I will know what you're into currently. So soccer, cooking, bikini clad girls. Like, you know, whatever you're currently into is going to be in your feed. And so you now get things you're interested in served up to you, not content from the people you follow. And that's a big deal. It's a big deal. You should double click into it if you're watching.

[Kurt]

I did a full digital detox. I unfollowed everyone and I was like, well, maybe nothing will pop up now. All the suggestions pop up. That's right.

[Gary Vaynerchuk]

And by the way, you don't even need to like and follow if you sit for an extra second on that UFC video. More than sitting when you're going. If you just sit on it for three seconds, and the next one's cooking, and it's one second, and then another one's boxing, and you sit on it for four seconds. Next week, you're getting fighting contact.

[Kurt]

Something that you. You suggest it, Right?

[Gary Vaynerchuk]

Oh, you searched and did, like.

[Kurt]

And puppies started coming up. So I can literally turn on my phone right now. And I. I had. I didn't follow any puppy. And literally, bro, I went in. I did puppies, I did rainbows.

[Gary Vaynerchuk]

Yep.

[Kurt]

And then I did health.

[Gary Vaynerchuk]

Yes.

[Kurt]

Generic.

[Gary Vaynerchuk]

Yep.

[Kurt]

I can go to my phone right now and I guarantee you.

[Ad]

Yeah.

[Kurt]

And this. But it's. You say, oh. The next day, it started kind of immediate. Yeah.

[Gary Vaynerchuk]

Everybody. Because we're out of context. Let me tell you what my man here did. Everyone's like, oh, the algorithm, me up. Facebook, me up. China and TikTok me up. We're me up. I'm up. It's not China. They don't care about you. It's you. It's you. Like, it's you. So I said to people, you. You don't believe me? Let me show you. And this is for all y', all, literally, right now. Go into TikTok and Instagram and search. Go into Search and search. World cup sneakers, puppies, rainbows. Just search it like a couple of posts. Follow an account and tell me what your account looks like tomorrow. Because the reason you're getting all this politics and negativity and conspiracy theory is. Cause you're rubbernecking. You're looking for negativity. It's you. Algorithms didn't change you. They exposed you, motherfucker. They exposed you.

[Kurt]

Right.

[Gary Vaynerchuk]

Facebook didn't make you a racist. You're a racist.

[Kurt]

You racist mother. All right.

[Gary Vaynerchuk]

But it's real, bro.

[Kurt]

Plastic is the new vhs.

[Gary Vaynerchuk]

Plastic is the new vhs. Yeah.

[Kurt]

And that came from, like, say, for instance, cash. Oh, oh, oh. Cash is king. Cash is king. I would walk around, I would always say, man, I got to have cash in my pocket. My kids could have a dollar, and it could be Halloween, and they'll still have that fucking dollar in their pocket, bro.

[Gary Vaynerchuk]

I grew up. My sister knows this. I used to really roll with cash. Like, my entire net worth was in my pocket my whole life.

[Kurt]

Gotta see it.

[Gary Vaynerchuk]

Forget about plastic. Ain't even it. Like, I don't even carry credit cards. It's all food. Tap, tap, tap, tap.

[Kurt]

Conversation this morning. Like, literally, I can go into my kitchen, and my daughter's credit card is sitting. Sitting in the kitchen.

[Gary Vaynerchuk]

Yeah. Because she doesn't need it, cuz her credit card's right there.

[Kurt]

Yeah, yeah. Trust me, I know it. I pay the bill. I love when I go out with my daughter and she'll be, oh, Dad, I got it. And she. I'm like, no, you don't.

[Gary Vaynerchuk]

I paid for it on the back end. Thank you.

[Kurt]

But yet it's that thin.

[Ad]

Yeah.

[Gary Vaynerchuk]

And bro, that, that's just minor leagues. Wait till the glass. Wait till your retina is paying.

[Kurt]

Oh, my God.

[Gary Vaynerchuk]

Yeah, bro, like all that is, is it's less friction. Less friction, less. You already know it. Amazon already did it right in the airport. I think even in la, right, you can go grab the food and walk out and you're paid, right? Like no cashiers with AI now, shit's gonna go so fast.

[Kurt]

We losing that human touch.

[Gary Vaynerchuk]

Yes, but, but if this was 1939, people would say the television lost a human touch, the telephone lost a human touch. The typewriter. Do you know how many people had feedback about the typewriter?

[Kurt]

Yeah, and I took all that fucking typing class.

[Gary Vaynerchuk]

Me too. And I got an F. But, but, but every generation says, people said the car, the car was gonna ruin us. Like everything's ruining us. And nothing ruined us. People need to stop sleeping on humans. On some real talk, people need to stop sleeping on humans. Everything was gonna ruin us. And, and everything advanced us. You can be upset about everything. There is no debate that the world has never been in a better place. People are healthier than ever. There's like all the conflict you feel, it's still less shit used to be really fucked up. My guy. Like, I don't think people understand. Like, we've made a lot of progress in the macro. In the micro, there's always fucked up shit. In the micro, there's always fucked up shit. Somebody's watching this podcast and tonight they're going to get punched in the face because they're on the wrong side of the tracks in San Francisco, New York. And I know, see, see, garyvee, you're wrong. On an individual level, there's always opportunities for anything. But in a macro, things get better with technology, not worse. That's been proven for 3, 400 years. What do you want from me? What do you want from me?

[Kurt]

Who's going to get left behind?

[Gary Vaynerchuk]

People that fucking dig in their heels to yesterday. People that ready, AI is not taking your job. Someone that uses AI is going to take your job. Like what? Like what, what?

[Kurt]

Like the person that's in school now and that degree, by the time they

[Gary Vaynerchuk]

graduate, don't get me started. This was some shit that I was very historically correct about. People thought I was on college because I was bad at school. I was shitting on college because I would talk to unlimited people, getting messages from them. They're $150,000 in debt and their University of Indiana degree wasn't getting them a job like it was 1984 anymore. Education's all twisted. It's all twisted. What are we? How can we possibly, with all the technology we have, still be rewarding kids to memorize something and then spit it out and then forget it? We gotta change all that. We gotta change all that.

[Kurt]

My son just started his online store.

[Gary Vaynerchuk]

Yes.

[Kurt]

For anyone that's doing that. Drop shipments and what?

[Gary Vaynerchuk]

Live Shopping.

[Kurt]

Live Shop.

[Gary Vaynerchuk]

QVC of social media, TikTok shop whatnot. It's about to eat up the world. This is e. This is 1996 all over for me. In 1996. I knew that E Commerce was going to change the way stores worked in 2026. I know that Live shopping is going to change the way we know E Commerce. What's better? Going to a website and looking at a picture of a dress or watching a human being in video form explain the fuck out of that dress, potentially charismatically. What's better? Everyone's like, oh, I like real life. Cause I like going to the store and having someone talk. Good. That's that. Live shopping is the biggest for everybody who's watching. If you sell something, you got a fashion brand because you like made 10t shirts like so you know that one Sell on Live Shopping.

[Kurt]

Thank you, bro.

[Gary Vaynerchuk]

Thank you for having me. Legend, really. It was a real pleasure on my ship. It's a real honor for me too, man.

[Kurt]

You did so many of these. I had to go and ice my.

[Gary Vaynerchuk]

I'm very Eastern European. Touchy. I'm very touchy.

[Kurt]

Almost feel like. Jerry V. All fair. I love it, man. Now you've been given the tools. Go build it 100%. Thank you, bro. My man. Thank you everybody.

[Gary Vaynerchuk]

If you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this.

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[Gary Vaynerchuk]

See you later.