Live Shopping in 2026 is Social Media in 2011

Summary

The GaryVee Audio Experience

Episode: Live Shopping in 2026 is Social Media in 2011
Date: June 26, 2026
Host: Gary Vaynerchuk
Summary by Podcast Summarizer AI

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Episode Overview

In this lively, reflective, and humor-filled episode, Gary Vaynerchuk sits down over wine and pasta with an interviewer and guests to dive into the future of business, live shopping, the evolution of entrepreneurship, personal philosophy on love and success, technology, mental health, and life lessons. The episode is themed around the idea that live shopping in 2026 is at the same disruptive early stage social media was in 2011, with Gary drawing wide arcs from childhood business ventures to his current outlooks, sharing candid stories, tactical business advice, and personal vulnerabilities.

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Key Discussion Points & Insights

Gary’s Entrepreneurial Beginnings & Philosophy

• Childhood Hustle and School Experience

  • Gary recounts being both a class clown and a teacher’s pet, always selling things from candy to baseball cards ([01:22]-[02:32]).
  • Early recognition that entrepreneurship was undervalued in the 80s/90s compared to present day.
  • “My brain was always entrepreneurial. ... I was playing against the current in the 80s and 90s, but I was locked into what is now known as entrepreneurship.” ([03:22])

• Parental Influence and Love

  • Gary credits his mother with instilling deep love and positivity:
    • “I am only motivated by that because I was instilled with so much love for my mom. ... I don’t even fucking know how to see the world another way.” ([00:06], [68:05])

• Early Business Lessons

  • Discusses the stigma of not following traditional routes and how his model would be celebrated today ([04:22]-[05:33]).
  • “I was just doing what the fuck I wanted to be doing, and that was business.” ([05:14])

Building Wine Library & First forays into Digital

• Gary tells the story of taking over and rebranding his father’s liquor business, shifting focus to wine and collections based on his passion for collectibles. ([08:26]-[09:33])
• By the time he started Wine Library TV (2006), he had grown the business massively, and his father trusted his unusual, forward-looking moves. ([10:10]-[11:24])
• Early adoption and risk-taking in the digital era:
  • “Everything I was doing was so progressive and didn’t make sense at the time.” ([10:17])
  • “It would be like me saying: We need an AI robot to do X, Y, and Z. ... It was in the ether, but so far-fetched.” ([10:34])

Entrepreneurial Role Models

• Gary’s "Mount Rushmore" is filled not with classic business titans but with entrepreneurial storytellers and creative moguls:
  • Dana White, Vince McMahon, David Stern, Walt Disney, Jim Henson, Stan Lee ([11:32]-[14:26])
  • “I’m very fascinated by that entrepreneur that you have both creativity and salesmanship. And I fall into that category to some degree.” ([14:03])

The American Dream: 2026 Perspective

• The American Dream hasn’t changed, but belief in it has eroded due to fear-driven narratives and social pessimism. ([14:44]-[16:58])

• Gary pushes back hard on generational pessimism—asserts that gatekeepers are gone, opportunity is unprecedented, but negativity creates self-fulfilling defeat.

  “The American Dream, on its merit and opportunity, has never been greater. ... However, more don’t believe in it. And that is a sad affair ... preying on their insecurity.” ([15:45]-[16:58])

Live Shopping as the Next Social Media (Key Theme)

• Advice for Early-Stage Brands
  • Gary emphatically states live shopping is the under-the-radar gold rush (compared to China’s $1T GMV):

    “Where live shopping is right now ... is where social was probably in 2011. ... The masses don’t know it. ... For a fashion brand, live shopping is at the tippy-top of the list.” ([17:48]-[18:40])

  • Encourages a mix of tactics—content, influencer deals, pop-ups, and especially live experiences ([19:39])
  • Analogy: “The modern MMA fighter is the comp to the modern entrepreneur. You gotta do it all.” ([19:58])

NFTs, Digital Collectibles, and Cyclical Markets

• Gary corrects misconceptions:

  • “Most people think NFTs are beanie babies. ... Projects within stuffed animals come and go. ... But digital collectibles on the blockchain is a guarantee and inevitable.” ([21:15]-[22:33])

• History lesson: Internet bubbles/busts always wash out greedy players, but foundational innovations (like NFTs) persist.

Management Reflections: Firing & Candor

• Shares vulnerable story on poor candor when firing employees.
  • For years, avoided direct conversations; led to resentment and confusion.
  • Learned the power of “kind candor” and how critical it is to leadership.

  “My kryptonite was lack of candor when it came to someone underperforming ... Your biggest vulnerability is what you can’t see. When you see it, you at least know and you’re navigating. When it’s your blind spot, that’s fucking tough.” ([23:46]-[30:06])

Gary’s Business Ls & Regrets

• Turned down early investment opportunities, most notably Airbnb and Uber, even with personal connections.
  • “I passed on Uber twice in the angel round ... my inability to dwell, cry about spilled fucking milk, is one of my greatest strengths. ... There is no time machines.” ([30:13]-[31:58])

Personal Philosophy: Love, Purpose, and Accountability

• On Love:

  “People think hate’s winning. But fucking, bro, in the end, love is gonna win. ... I root for people. I root for the extremes of people ... I love love so much that I can’t wait for it to become clear to a lot of people in the world that it always defeats hate.” ([00:06], major callback at [68:05])

• Sports/Star Wars analogies: “Hate is leading love by 18 going into the fourth quarter. But I know love’s gonna win when it hits triple zero.” ([68:39])
• On Accountability:
  • “When it’s they, you’re fucked. Cause you’re not in control of they, but you’re very fucking in control of me and I.” ([83:29])
  • “I had to bite my cheeks, bite my tongue, not cry, and start figuring it out ... point thumbs, not fingers.” ([55:42]-[56:07])

Technology, AI & The Future

• Sees AI-enabled live shopping and generative AI as inevitable, with smartphones likely giving way to smart glasses in the next decade. ([81:09]-[81:18])
• Jokes about starting businesses around AI-generated food, highlighting the blurring lines between human and artificial creation. ([58:06]-[61:27])

Mental Health, Dependency, and Motivation

• Distinguishes between real mental health struggles and those who weaponize it for excuses ([73:18]-[74:39]).
• Sheds light on his own behavioral triggers (e.g., needing an external accountability partner to change health habits) ([75:12]-[76:03]).

Parenting, Family, and Friendship

• Gary cherishes his family, especially the growing friendship with his now-teenage son ([65:43]-[66:38]).
• Believes having children transforms perspective; maintains close ties with childhood friends but work comes first ([64:43]-[65:29]).

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Notable Quotes & Memorable Moments

• “That might be the question I’ve been waiting for someone to ask me.”

  • On being motivated by love ([68:05], [83:29])

• “Live shopping is where social media was in 2011. The masses don’t know it yet. ... That is fucking insanity.” ([18:40])

• “People think that if you shit on someone, some way miraculously your life’s better.” ([17:06])

• “Your biggest vulnerability is what you can’t see. When you see it, you at least know and you’re navigating. When it’s your blind spot, that’s fucking tough.” ([30:06])

• “Point thumbs not fingers ... When the fuck is it your fault that you fucking suck?” ([55:42]-[56:07])

• “There’s no content out there of me being pumped about four hours of sleep.” ([46:45]-[47:35])

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Timestamps for Key Segments

• Gary’s Love Philosophy: [00:04], [68:05], [83:29]
• Entrepreneurial Beginnings: [01:22] – [05:33]
• Wine Library/YouTube: [08:26] – [11:24]
• Role Models & Storytelling Entrepreneurs: [11:32] – [14:26]
• American Dream 2026: [14:44] – [16:58]
• Live Shopping Advice: [17:48] – [19:58]
• NFTs/Digital Collectibles: [21:15] – [22:33]
• Firing & Candor: [23:46] – [30:06]
• Biggest Regrets: [30:13] – [31:58]
• Family, Children, Friendship: [64:43] – [66:38]
• AI and Future Tech: [58:06], [81:09]
• Mental Health Discussion: [73:18] – [74:39]
• Personal Setbacks & Accountability: [53:34] – [56:07], [83:17]

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Recap: The GaryVee Mindset

Gary’s blend of practical wisdom, personal vulnerability, relentless entrepreneurship, and undaunted optimism sets the tone. His core messages:

• Love over hate is not only a personal value but a foundational business and life principle.
• The window for innovative digital businesses—especially live shopping—is wide open.
• Accountability, candor, and starting with “I” are crucial for progress.
• Nostalgia and emotional connection are underutilized business levers.
• Don’t dwell. Look forward, own your mistakes, and act.
• Simplicity, self-awareness, and humor go a long way in both life and business.

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Recommended for anyone seeking candid entrepreneurial truth, strategic digital insight, and heartfelt life perspective—delivered with Gary’s trademark energy and rawness.

Transcript

[Gary Vaynerchuk]

That was one of the best questions I've ever been asked in a podcast or interview in my career.

[Interviewer]

How motivated are you by love?

[Gary Vaynerchuk]

Very. It is my biggest truth right now. People think hate's winning. But fucking, bro, in the end, love is gonna win. I'm blown away by watching other winners shit on other winners. Cause they're jealous because that winner made a little more. The girl's a little hotter, and I'm like, why? Like, why don't you have the capacity to know that you're fucking amazing? I really root for people. I root for the extremes of people. People really struggling really motivate me. I want to get them the fuck out that darkness. I love love so much that I can't wait for it to become clear to a lot of people in the world that it always defeats hate. I'll always be there for people. I always want to step up if I can. I want people to win. I am only motivated by that because I was instilled with so much love for my mom. I'm not cool. My mom's cool for putting that so deep in me that I don't even fucking know how to see the world another way. This is the GaryVee audio experience.

[Interviewer]

What'd you do today?

[Gary Vaynerchuk]

What'd I do today?

[Interviewer]

Yeah.

[Gary Vaynerchuk]

Clowned on some of my Philly fan friends.

[Interviewer]

Okay.

[Gary Vaynerchuk]

Got some work done.

[Interviewer]

Yep.

[Gary Vaynerchuk]

Typical day.

[Interviewer]

As you should.

[Gary Vaynerchuk]

As I should.

[Interviewer]

As you should.

[Gary Vaynerchuk]

How about you?

[Interviewer]

Nothing.

[Gary Vaynerchuk]

Zero. Nothing yet.

[Interviewer]

Okay. Just had some wine. It's early.

[Gary Vaynerchuk]

That's always a good.

[Interviewer]

So, growing up, I always wonder about you when you were a kid.

[Gary Vaynerchuk]

Okay.

[Interviewer]

Were you a class clown?

[Gary Vaynerchuk]

I was teacher's pet. I was a rare breed that was. I wasn't a teacher's pet because I got D's and F's and I'd always fucked with them. But I was the kind of class clown that the teacher liked because I didn't disrespect them. I was just trying to eliminate as many minutes from the class as humanly possible. And I think some of them appreciated the creativity.

[Interviewer]

They saw value.

[Gary Vaynerchuk]

Yeah, I think they saw value. And I think they also saw that my intent wasn't that negative. It was just my brain was not interested in what they were saying.

[Interviewer]

Yeah. What was your brain thinking about at

[Gary Vaynerchuk]

that time in grammar school? It was selling candy.

[Interviewer]

You sell cheese and crackers?

[Gary Vaynerchuk]

Really?

[Interviewer]

Yeah. Thanksgiving, Halloween, candy to my hungry cousins?

[Gary Vaynerchuk]

Yes, stuff like that. I wish I sold cheese. That would have been smart. Cheese for cheese. You know what I'm saying? In middle school, it was. We couldn't get real wine here. Grape juice?

[Interviewer]

Yeah.

[Gary Vaynerchuk]

Later it was baseball cards, and then later it was learning about real wine. So the wine is not to your liking? Well, it smells like grape juice. And I thought this was an evening establishment, you know, and distribution on the modern web. This is not on Netflix or anything, right? No. So we can do real wine, sir? Yes, we can.

[Interviewer]

I think he cheaped out. You placed order for this?

[Gary Vaynerchuk]

I'm sorry, I thought just. There's nothing to be sorry about. But, you know, I grew up in the wine game and I can smell grape juice.

[Interviewer]

Quick, you see that photo of him up on the wall?

[Gary Vaynerchuk]

Look at that. I'll get you a bottle of wine. Real wine? Yes, if that's what you would like.

[Interviewer]

Yeah, you know, that'd be nice.

[Gary Vaynerchuk]

Yeah, that'd be good.

[Interviewer]

All right, I'll be right back. Thanks, Luigio. So you like flipping stuff? You were flipping cards, garage sales, stuff like that?

[Gary Vaynerchuk]

Yeah, I was. My brain was always entrepreneurial. You know, I'm older than this crew behind the camera, and a lot of people that are watching meaning Today, everyone under 35 understands that entrepreneurship is a viable out, is a viable way. For all the great people behind the cameras that are 50 and older like myself, we were taught that school was the only way and going to a great college was the only way. And so it was really interesting because I wasn't getting the support today. I would get support today. If I was in seventh grade and I'm killing it in business, my teachers would view that as good for you. That's viable. When I was killing it in seventh grade, my teachers were telling me that I would never amass to anything. So, yeah, I mean, I was playing against the current in the 80s and 90s, but I was locked into what is now known as entrepreneurship. At the time. I thought of it as like, I'm gonna be a businessman.

[Interviewer]

Yeah. Did you spend a lot of years people telling you you're crazy beyond school, or was everyone kind of like, this is Gary, he knows what he's doing?

[Gary Vaynerchuk]

I think it was a mix. I think my friend's parents in Jersey thought it was a little crazy. They were worried that I was gonna rub off on their kid and they would get worse grades. They knew I wasn't a bad kid. So it wasn't like my friend's parents didn't want them hanging out with me because I was gonna get them into bad shit. But I'm telling you, and I'm gonna say it again. Cause how old are you 28? Jesus, you look great. Thank you. You know, you didn't grow up with the same framework. It was different. It was like, if you do not get good grades, you cannot achieve. It's almost like the reverse now. And so. And so the parents thought it was crazy. My friends didn't give a fuck. My friends were like kids. They were 12, 19, 17, 13. They were worried about hooking up or their football, you know, practice. So it was misunderstood, for sure. I'm not sure I even thought about it in any real significant way either. I was just doing what the fuck I wanted to be doing, and that was business.

[Interviewer]

On the come up, were you dating a lot, giving any attention to the ladies, or. Not really.

[Gary Vaynerchuk]

I liked girls. And, you know, I mean, in fifth grade, I dominated. I was really cute and so, like, you know. Yeah. You got a good face. Thank you. Not even low key. I would say high key for you.

[Interviewer]

High key.

[Gary Vaynerchuk]

Mine's harder to decode now, but, like, fifth grade. I dated a girl named Rocky in fifth grade. Rocky Marie? Yes, sir. This establishment does not have a liquor license. I wasn't able to get you wine. I respect that. So I am ready to take your water, though.

[Interviewer]

You want to eat something?

[Gary Vaynerchuk]

Yeah, I think we should.

[Interviewer]

I Recommend the pasta 10. The 10 on there, it says pasta 10. It's pretty good.

[Gary Vaynerchuk]

What kind of pasta is it?

[Interviewer]

Can you explain Pasta 10 to him?

[Gary Vaynerchuk]

We have white or red pasta?

[Interviewer]

It's red.

[Gary Vaynerchuk]

The sauce.

[Interviewer]

I believe it's red.

[Gary Vaynerchuk]

The sauce that's on pasta. They're both very good.

[Interviewer]

You like red?

[Gary Vaynerchuk]

I like red.

[Interviewer]

Red, white.

[Gary Vaynerchuk]

I'll be right back.

[Interviewer]

Thanks.

[Gary Vaynerchuk]

Why'd you take white?

[Interviewer]

You want white?

[Gary Vaynerchuk]

Well, no, I'm just curious what you were doing.

[Interviewer]

Share it?

[Gary Vaynerchuk]

Yeah, I do like to share, yeah. One red, one white.

[Sponsor/Ad Voice]

All right.

[Gary Vaynerchuk]

Thank you, sir.

[Interviewer]

What was the last thing we were saying?

[Gary Vaynerchuk]

I was saying that I dated Rocky Marie, who, you know, now, in hindsight, like her. I wonder if her grandpa owns this place. She was really Italian. She was also twice my height.

[Interviewer]

Wow.

[Gary Vaynerchuk]

Yeah, she was a beast.

[Interviewer]

What'd you guys do?

[Gary Vaynerchuk]

We held hands while running in gym.

[Interviewer]

Okay.

[Gary Vaynerchuk]

Which was like second base, back in 1984.

[Interviewer]

Were the teachers jealous?

[Gary Vaynerchuk]

I don't know. She just moved in and she was instantly popular, so that was a big win for me. And then I moved in eighth grade to Hunterdon County, New Jersey, from Edison, New Jersey. And those kids went to school. I only had 40 kids in my class. I went from 40 kids in my homeroom in Edison to 40 kids in my grade in eighth grade. And those kids spent all of kindergarten through eighth grade together. So anyone that didn't look, like, completely broken and moved into town dominated. So Stacy Johnson, the prettiest girl, liked me in eighth grade. That was huge. She tried to kiss me under the pool table at a Halloween party, but I was scared. Yeah, you're just nervous. Yeah, it's one of the great Ls of my life.

[Interviewer]

Stacy's mom.

[Gary Vaynerchuk]

Stacy's mom's got it going on. And this wasn't even Stacey's mom. She was, like, the fresher version. Yeah, she was a beast, too. Fucking beast. So a little bit, like. But I was really, really A, slow to mature with girls, and B, just completely obsessed with work and business, and that was kind of where I was at in my youth.

[Interviewer]

Yeah. Cool. And your dad with the wine shop you started the wine library.

[Gary Vaynerchuk]

I rebranded. I executed the wine library. My dad's store. You know, my dad's such a hero to me. He came to this country with no money. Went from being a stock boy making two bucks an hour to owning this small corner liquor store in New Jersey. But it was a real business, and it was called Shoppers Discount Liquors.

[Interviewer]

I looked it up, man.

[Gary Vaynerchuk]

Yeah. So it was a real liquor store. Right. It was really booze and beer. But I saw that people were into wine, and I was interested in this concept that people collected wine. That was huge for me because I was so into collecting cards, and I didn't like the beer and liquor thing. My mom was very Nancy Reagan doubt. Do you know what that means? Nancy Reagan was Ronald Reagan's wife.

[Interviewer]

Okay.

[Gary Vaynerchuk]

And she had a big campaign. Just say no to drugs and alcohol and all this. And so my mom was really focused on me being a good boy. Uh. Oh, yes. The red and the white. Thank you so much, sir. Thank you. And so when I realized that people collected, that was a huge, huge factor for me.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

And. And that's really what got me into wine. Right.

[Sponsor/Ad Voice]

Mm.

[Interviewer]

So when you started filming the videos. Right. Because you went QVC kind of style with it.

[Gary Vaynerchuk]

This grape juice sucks.

[Interviewer]

Yeah, it's disgusting. Yeah.

[Gary Vaynerchuk]

That was a huge.

[Interviewer]

Luigi, next time, forget the license.

[Gary Vaynerchuk]

Luigi, do you have What? I know. You have red and white, you know, pasta. Do you have red and white juice? Do you have white grape. White. White grape. Apple juice or juice? Excuse me. I will go and look in the back, see if we have. Okay. In the back. Thank you, sir.

[Interviewer]

Anything, really. What'd your dad think when you started saying, hey, look, I'm Gonna film, I'm gonna do it this way.

[Gary Vaynerchuk]

Oh, that happened much later. So I built that business from a 3 to a $60 million business before I even started doing wine library TV. So by the time I'm like, dad, I'm gonna make these videos and do it on YouTube. He blindly believed that I could do anything.

[Interviewer]

He just said, you got it.

[Gary Vaynerchuk]

Yeah. Because everything I was doing, having a website again, just so fun to have all the kids behind the camera and knowing a bunch of kids are watching kids, 20, 30, 40 year olds. The Internet was brand new. That'd be like me saying like, we need an AI robot, you and I to do X, Y and Z. It was so far fetched. It was in the ether, but it was so far fetched. So email marketing, spending all our money on Google, this new site instead of direct mail. Everything I was doing was so progressive and didn't make sense at the time. But by the time I did Wine Library TV in February of 2006, I'd already been running the business day to day for eight years. I'd already won a lot of credibility and the confidence my dad had in my decisions was high. He didn't understand it, but he understood me at that point.

[Interviewer]

Yeah, who's on your millionaires, billionaires, multimillionaires, Mount Rushmore. Who'd you look up to in business?

[Gary Vaynerchuk]

That's a good question. I don't tend to look up. Not out of audacity or I think I'm cool. It's just not how my brain thinks. I will say I'm very into entrepreneurial storytellers. So what I mean by that is when I think of this group, Dana White, Vince McMahon, David Stern, who was the NBA commissioner during the Jordan Byrd years, Walt Disney, Jim Henson maybe the most because he had built a huge world and made a lot of money. Entrepreneur. But he also, you know, Sesame street, the Muppets, they have good intent.

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[Interviewer]

Spider.

[Gary Vaynerchuk]

Yeah, and really X Men mutants. They're different than us, but let's accept them. So my favorite entrepreneur. It's why I'm building veefriends.

[Interviewer]

Oh, we're talking. I can't wait.

[Gary Vaynerchuk]

Thank you. It's probably, you know, I think in 20 years when I'm doing something like this, that will be what I'm known for. More than the wine stuff or the marketing stuff, I would say. My Mount Rushmore apparently has the people that were able to create characters that the world fell in love with. Vince McMahon did it with Hulk Hogan. Dana White did it with Conor McGregor and Ronda Rousey. David Stern did it with Magic Johnson, Larry Bird, Michael Jordan. And then obviously Stan Lee and Kirby and those guys did it with all the incredible Marvel characters. And Jim Henson did it with Kermit the Frog and Big Bird. And Walt obviously did it with Mickey and others. I'm very fascinated by that entrepreneur that you have both creativity and salesmanship. And I fall into that category to some degree. Subjectively. I think so. And so I think that's why that person, more than a Bezos or an Elon Musk or an Oprah Winfrey, that person resonates to me because that's how my brain sees the world.

[Interviewer]

Building an ip.

[Gary Vaynerchuk]

Building an ip, whether that's human, right, King Kong Bundy or Magic Johnson or. Or whether it's a fictional character. Fred Flintstone, Scooby Doo Doug from Nickelodeon for you youngsters.

[Sponsor/Ad Voice]

Hmm.

[Interviewer]

What is the 2026 version? What is the 2026 version of the American dream?

[Gary Vaynerchuk]

That's a really complicated and good question. Personally, I think it's exactly the same. We live in a country that, compared to other countries, has a remarkable amount of infrastructure in place, including our cultural DNA, to allow people to go from dirt to penthouse. I believe currently all of you are consuming way too much negative bullshit that is predicated on, let me be a politician, a business, a parent, a teacher, a pontificating podcaster. I'm gonna deploy hate on you. I'm gonna deploy fear on you so that you think I can help you. I'm gonna scare you so that you think I can help you.

[Interviewer]

I can save you.

[Gary Vaynerchuk]

Correct. And I think so many people have bought into that, which makes a Lot of people currently believe that the American dream is not valid. For example, an ungodly amount of kids under 30 will see a TikTok or Instagram that tells them you're fucked. Your generation's the worst, you the first generation to have it worse. Meanwhile, there's unlimited 20 and 30 year old fuckers making money that was uncomprehendable in my era. The Internet, social media created an unbelievable AI, an unbelievable amount of opportunity. But because everyone has believed that it's worse, people think the American dream is dead. The American dream on its merit. And opportunity has never been greater. There's no gatekeepers in Hollywood and Madison Avenue, like and Wall street the way there used to be. However, more don't believe in it. And that is a sad affair of a group of individuals, both on the left and the right, up and down, who have figured out that most people are insecure and they're preying on their insecurity.

[Interviewer]

What are these kids wasting their time with today?

[Gary Vaynerchuk]

Putting too much energy into fear and hate.

[Interviewer]

A lot of hate online.

[Gary Vaynerchuk]

Yeah, man. People think that if you shit on someone, some way miraculously your life's better.

[Interviewer]

That's what my dad thinks.

[Gary Vaynerchuk]

Yeah, bro, I get it.

[Interviewer]

My grandfather, every day he would be puking sick. Hey, this is my cousin right here, Gary. Nice to meet you.

[Gary Vaynerchuk]

What's up, man? How are you?

[Interviewer]

Pull a chair up for a minute. He's an entrepreneur.

[Gary Vaynerchuk]

Oh, is this the cousin on your dad's side?

[Interviewer]

He's on my dad's side.

[Sponsor/Ad Voice]

Oh, great.

[Gary Vaynerchuk]

So we're talking about grandpa.

[Interviewer]

We've done some business, we're in business together.

[Gary Vaynerchuk]

I love that.

[Interviewer]

But Gary, how can I take my business to the next level?

[Gary Vaynerchuk]

What is your business?

[Interviewer]

I sell clothes. I'm a designer artist.

[Gary Vaynerchuk]

Yep. How do you sell it now? Wholesale or direct to consumer or both?

[Interviewer]

Just my website, online post on Instagram live.

[Gary Vaynerchuk]

Now that, brother, I'm telling you right now, like, first of all, that's incredible. I might have to do that. Second of all, where live shopping is right now, TikTok, shop, whatnot, soon to be meta and YouTube and all the rest, is where social was probably in 2011. Yeah, in 2011, social with the social we all know was probably six, seven years old.

[Interviewer]

Six, seven.

[Gary Vaynerchuk]

Yeah, six, seven. I knew it. Others knew it, but the world didn't know it. Not everyone knew it. Live shopping right now. There are a lot of people that are gonna leave comments in this video that are like, yeah, I've been making money. Like it's happened. I'm a TikTok affiliate. I'm making bank. But you know this. The masses don't know it. Yeah, I would say for a fashion brand, live shopping is at the tippy top of the list.

[Interviewer]

Selling on a live stream like this

[Gary Vaynerchuk]

shirt right now, 100% now. What's that? They bid on it or they buy it now. There's a shitty way to do it. It's kind of like just QVC and like. And then there's entertaining way. Look what's going on here. There's a shitty way to do a interview and a podcast and a video blog. And then it's y' all doing this proper so you can elevate the experience of live shopping. But to put into context China this year, $1 trillion of GMV, which stands for Gross Merchandise Value. $1 trillion of stuff will sell in China through live shopping. That is fucking insanity. That is for you for sure. Obviously making content. Obviously. Influencer, micro influencer deals, pop ups. Yeah, yeah. Three, four weeks in the right place, doing something proper at cultural events. Rolling loud, Coachella. Yeah.

[Interviewer]

I mean, you got to do it all.

[Gary Vaynerchuk]

It's always. And people think it's one move. It's like fighting, right? Why did UFC emerge? It's not just boxing. It's not just jujitsu, it's not just wrestling. You have to have it all. I would argue the modern MMA fighter is the comp to the modern entrepreneur. You gotta do it all.

[Interviewer]

Yeah. It's the Rhinos.

[Gary Vaynerchuk]

You like that, right? That hit. Bring it. That hit, right? I do like that analogy.

[Interviewer]

Well, I appreciate it.

[Gary Vaynerchuk]

Oh, good to see you, brother. You gotta run. You outta here. Where are you going tonight?

[Interviewer]

I gotta get some work done, so.

[Gary Vaynerchuk]

I appreciate that. I respect that.

[Interviewer]

Are NFTs coming back?

[Gary Vaynerchuk]

NFTs are still here. What most people don't understand about NFTs. And if you look back at my videos and please, Cole, edit it in here. I want the receipts like. This is not an edit. I'm just talking to you while I'm talking to them. When I made the video saying 99% of NFTs were going to go to zero in August of 2021, it's because NFTs are just like trading cards and comic books. 99% of comics are worthless. 99% of trading cards are worthless. For you kids, 99% of sneakers are worthless, but 1% are worth money. So what blows people away when I talk about it now is go look at OpenSea right now and see the millions of dollars in NFT sales last Week. But the whole world thinks it was a scam and it's shit. Most people think NFTs are beanie babies. NFTs are stuffed animals. Projects within stuffed animals come and go right now. Jelly Cats are good.

[Interviewer]

Love those.

[Gary Vaynerchuk]

You do love those, right? Yeah. You got a couple?

[Interviewer]

I have a few.

[Gary Vaynerchuk]

Nice. Squishmallows are solid, but Cabbage Patch Kids used to be. There's just ebb and flow. It's like fashion. All you fuckers were wearing skinny ass jeans nine years ago. Now you're baggy as fuck. Goes back and forth, back and forth. And so that's kind of where NFTs are. It will take three to five years for the stink to get off that brand. But that's what happened with the Internet. Here's a history lesson for all of you. In April of 2000, I think, I think it's 2000, all the Internet stocks crashed. EBay, Amazon, PayPal, they went from a buck 50 to $3. $4. Pets.com went to zero. A million others went to zero. And all the articles and everybody running around town in 2000 was like the Internet was a fad. Literal articles written. See, the web was a fad. What happened was greed took over in Wall street and Silicon Valley and tipped it. What happened with NFTs is greed took over. Everybody was trying to make a quick buck, but digital collectibles on the blockchain is a guarantee and inevitable. And there'll be five to 10 to 15 projects from that 20, 21 hysteria that will make it to the other side.

[Interviewer]

Yeah, look. What Louisiana.

[Gary Vaynerchuk]

Luigi.

[Interviewer]

You made a miracle happen. Look at that.

[Gary Vaynerchuk]

You like this brand? I do like this brand. Who'd you hit up? Tell me, Luigi, who's the plug? I found it hidden in the cellar. Little Pinot Noir stash?

[Interviewer]

Yeah, little Noir. How do you go about firing somebody?

[Gary Vaynerchuk]

Me?

[Interviewer]

Yeah. I think you have to.

[Gary Vaynerchuk]

Thank you, sir. I just. I think he needs me to sniffy sniff this. One second. I will answer that very important question in a little. Good stuff, Lloyd. Thank you. 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. Me personally, I want to be a little bit vulnerable here. Cause I think it'll bring value to everyone. I would argue from 22 to 45, a 23 year window. Thank you, my friend.

[Interviewer]

You're very welcome.

[Gary Vaynerchuk]

Appreciate that.

[Interviewer]

Thank you very much.

[Gary Vaynerchuk]

We aim to please at this establishment. Well, clearly you've accomplished it, pleasing me. To good health.

[Interviewer]

To great health. Enjoy.

[Gary Vaynerchuk]

Thank you, sir.

[Interviewer]

Thank you.

[Gary Vaynerchuk]

From 22 to 45, I would tell you it was by far the thing I did most poorly as a businessman, operator.

[Interviewer]

Was it emotional?

[Gary Vaynerchuk]

It still is. Okay, I was sloppy, I wasn't canderous. In my 20s, I would hide behind my cousin and father even though I was running the business. When it was time to fire someone, I did everything, made every decision. But when it came to firing, even though I made the decision, I was a puss and I would need my cousin to do it. And I would tell you, and this is like. Like, I know we're doing a really nice production here, but I hope this really helps someone because this was by far my kryptonite. I was very, very gifted with DNA and my mother and father and my circumstances, I was gifted. It worked out for me. My circumstances worked for me, timing worked for me. I was given so many talents naturally because my mom and dad had sex at the right second best. The best. I was born nine months to the day, my parents wedding night. That's how they did it back in the day in the Soviet Union. I was Superman entrepreneurially in a lot of ways, my kryptonite was lack of candor when it came to someone underperforming. So to answer you directly and not long winded, how did I fire? Poorly, mistakenly, embarrassingly bad. When I had this moment where I saw a Facebook group of former employees of VaynerMedia talking shit about me and I read every comment and these were people that I really like, like now. And it worked for me for four, five, seven years. It was a small group of the. At this point, 10,000 people that have probably come through the business plus in the last 15 years and you know, such a high percentage still here, feeling great, used it as a launching pad. But this small group really bothered me because they were part of the original core and forever here's how it would go down, somebody would be underperforming. And I didn't have the ability to tell them because I didn't want to scare them. Back to you saw how I reacted to fear. I fucking brought. I fucking hate fear. You have no idea how much. I think most people that are online right now that have audiences are straight fucking losers. Because I know exactly what the fuck they're doing. They're just scaring people on both sides. They're doing the same shit. Both fuckers. Left, right, blue, red. They're all fucking losers. Because they're tearing down people to build themselves up. So I hated fear. And I thought telling you, hey, you're not doing a great job. We need to. I thought you would leave my office and be scared and start looking for another job. I didn't know the value of kind candor yet. I had to develop that. And so I just sit on it. And actually what would happen is I became passive aggressive. I called it razzing with my inner circle, but it was passive aggressiveness. I would tell you, I'm not happy with you through a comment or a snark or this. And it's really challenging to even talk about out loud because it sucks. Because here's what would happen. Somebody would suck at their job. I would carry them for two years, brother. These are nice shoulder pads.

[Interviewer]

Thank you. Balenciaga.

[Gary Vaynerchuk]

Got it.

[Interviewer]

Thank you.

[Gary Vaynerchuk]

I would carry them for two years, and then finally, I would have the courage to call them in on a Monday, by the way, mind you, on Friday, I'm like, johnny, have the best weekend. You're the fucking best. And then Monday come in. So Johnny thinks he's getting a fucking prank promo. Because I fucking, you know, hit me on the shoulder.

[Interviewer]

I'm smash myself.

[Gary Vaynerchuk]

But, like, you know, like on Friday, like, I go to Johnny and be like, sorry, sorry, you right?

[Sponsor/Ad Voice]

I'm fine, bro.

[Gary Vaynerchuk]

I've been really. Yeah, yeah, I get it. So Friday, I'd be like, johnny, you're the fucking best. Have the best weekend. Be careful, be careful. Best weekend. One sip, shit, keep going. And then Monday, I'd finally build up the courage. Cause on the weekend, I'd be like, fucking Johnny's. And I'd fucking be, you know, johnny, I'm sorry, you know, it's the end of the road. And he'd be pissed. And I'd be pissed, like, Johnny, everybody in the company. How the. You know, I would blame him. How the fuck don't you know? You suck shit. Yeah, I've been ca. You're mad at me. I've been pinned you for a year to do nothing.

[Interviewer]

Johnny's sucking shit.

[Gary Vaynerchuk]

Sucking shit. And do you guys have shit here?

[Interviewer]

Luigi, can you take a shit

[Gary Vaynerchuk]

and serve it? You know, and so they'd be sucking shit. No, really, I get it, brother. But on real, like. I know. You know, it's funny, but, like, he would suck at his job. He would get mad. I get mad back. And I didn't take on accountability, that I did not put Johnny. Everybody who was average and good, I would put in a position to succeed. I would build up anyone who was a poor performer. I was not giving them a chance to fix it. And how would they know if I didn't tell them? And that was a dark day for me professionally when I had to look in the mirror and just say, fuck, this is my fault. It's not. Johnny's wrong. And I would say over the last five years, kind candor having the strength to be able, like, hey, Susan. Hey, Rashawn. Hey, Johnny. Hey, Sally. You know, hey, this. We subjectively think this is not going well. Can we fix this? It's been remarkable. It's changed everything in our company. You know, it's real. This is really. This actually makes me a little bit emotional. I had this great dream for 20 plus years of my career that no one was scared of my company because it was all rainbow and sunshine. Only to find out people were scared because they didn't know where they really stood with me. Because if they were around long enough, they're like, fuck, Johnny was good. And then Johnny's dead. Sally was good, and I was. That was. That was the most challenging emotional recognition of my professional career so far. Because that's the thing you're gonna learn as a youngster. And everybody's watching. Your biggest vulnerability is what you can't see.

[Interviewer]

True.

[Gary Vaynerchuk]

When you see it, you at least know and you're kind of navigating when you can't fucking see it. When it's your blind spot, that's fucking tough.

[Interviewer]

Yeah. What's an opportunity you just, like, really regret turning down? You're like, oh, shit.

[Gary Vaynerchuk]

I mean, I have an unanswered email from jorebedandbreakfast.com Airbnb. Yes, sir. Hey, Gary. Me and my two partners think you're the greatest. We'd be honored for you to be an investor. Missed it. Don't even know if I saw it or it got archived or I did see it and archived it. I've talked at nausea. We don't need to go into it. But if I can put a real number on it. I passed on Uber twice in the angel round. It doesn't sting because Travis is such a buddy, and I'm so happy he crushed. And two, I got in a little bit later and did incredibly well. But fuck, man, if I wrote a $50,000 check, $25,000 check, like I was writing at that time, fucking would have been 3 to $500 million. And he was my guy. It's not like it was a random startup person, you know, call Mike. I'm looking Right. Like, I know them. And when you say no to someone, you know, And I knew Trav better, and I know them, and I know them pretty solid. Like, that was. My God. I mean, in fact, crush it. My first book. This is my first book. The acknowledgments, my family and one random person, Travis, because he actually read it multiple times before it came out and gave me feedback that was a really big L and really crazy to think about because my life would be so substantially different because the financial impact of that decision would have completely butterfly affected my career. I mean, there's. You know what's crazy? And I hope this helps someone. I think most people spend a stunning percentage of their life dwelling on what they missed. The girl, the guy, the business, the investment, all this shit. You know what I'm talking about? I see you shaking your head. I think it's complete and utter waste of time. I answer it here because I don't want to dodge it. And I hope people can learn from it. And it's also great to see, like, no matter how good you are at something, you're making constant mistakes. But brother, I will tell you, my inability to dwell, cry about spilled fucking milk, look back and hurt my fucking neck is one of my greatest strengths. And I wish it on everyone. Because there is no time machines. There is no going back. And rolling in the mud of your missteps is literally one of the least productive fucking things a person can do. And it gets you into bitterness, which then starts to deploy envy and jealousy. And then you're fucking doom scrolling on your fucking couch, leaving negative comments to people that are actually building while you're fucking jerking off to OnlyFans. Exactly. I love jerking off to OnlyFans. Everything good. Like what? Besides OnlyFans, what is your top five? Jerking off. Listen, the.

[Interviewer]

I like to jerk off too people.

[Gary Vaynerchuk]

Eating. Yeah, I knew that's why you ordered it.

[Interviewer]

Punch me again. You know, I don't know, like.

[Gary Vaynerchuk]

Like eating. Eating.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

I knew you. That's why you were

[Interviewer]

kind of strong fingers, man. Do you like using AI?

[Gary Vaynerchuk]

Yeah, it's inevitable.

[Interviewer]

If you could. If you could automate your business, step away as a CEO and just take on a passion, you know, I'm sure you're passionate about the business, but let's pretend you're not. Well, no, let's pretend you are, but you move forward on some other new way. Let me read this question.

[Gary Vaynerchuk]

No worries.

[Interviewer]

Do you like using AI?

[Gary Vaynerchuk]

Yeah, of course it's inevitable.

[Interviewer]

If you could pursue a passion project, what would it be besides the business.

[Gary Vaynerchuk]

Besides the business. You know, business and work is my hobby. It's my passion. I have so many friends who are very passionate about their business, but they use their business to fund their real passions. Skiing, you know, music, traveling, partying. Like lots of different cool things. For me, it's like I use a business to fund my next business. It's really my hobby. But if you're. I want to answer you. I believe that if I. If there was a way to suck out my ambition and entrepreneurial DNA, I think I would be a therapist. So if I could fund a passion project, I would build a non profit mental health ecosystem where I could sit and be like fucking. I always dream about being like fucking Yoda. Like all fucking old as shit. Yeah, I just want to be old as shit in like some weird mountain that's kind of hard to get to because I want people to put in the work. And like you have to climb up this fucking mountain in like Peru and there I am. And if you like made it, then it's like, fuck it, I'll sit down with you and like chat about life. So I would say something like that.

[Interviewer]

Cool.

[Gary Vaynerchuk]

Like, to me, if I ever take a hard turn, this is just good for all of you to know. Like, if I disappear, I'm on some Dave Chappelle shit. But the good version, like, I'm off the. I'm gone, but I'm findable, but it's gonna be somewhere. Like, there's no, like, I'm either dying at the desk 97, building my empire, or to the full extreme, I'm on a weird chicken farm in Kenya that you have to like go under a tunnel. And then you could talk to me. Like something super left field to me, it's like either side of the pillow, nothing in between. The middle is not interesting.

[Interviewer]

Who's a random person you met, whether it be at a dinner dance party that really altered everything for you, changed your life in business or personal, whatever it is.

[Gary Vaynerchuk]

I would say the person that most had an impact on me randomly was Scott Harrison, the founder of Charity Water. I had dinner in New York one night, one of these classic, I'm always working, 10:30pm Starting dinners with a gentleman by the name of Chris Sacca, who was a very successful entrepreneur, excuse me, investor. And he brought Scott and Scott and I, we were having dinner, all just chopping it up. This was these golden days of 2009, 10, 11, 12. The world was changing. I was in the mix with all these incredible people and we're having this dinner just like this. And eat, by the way, please.

[Interviewer]

I'm kind of enamored.

[Gary Vaynerchuk]

Okay, respect. And Scott said something to me and you know, it's fun because I live a life where I say something and I get emails. Six years later, that one sentence changed your life. That's what I'm trying to do right now. How do I bring value? Scott looked me in the face about an hour into the dinner and said, gary, I have a good read on you. Which I was like, it was an interesting start. I think that way I'm pretty intuitive. So I thought it was interesting because I'd never really been on the receiving end of such an aggressive opening line. He goes, let me get this straight. You're going to go rags to riches, you're going to be very successful and in your older age, you're going to do good, you're going to like, do good stuff, you're going to give a lot of your money away, you're going to do this stuff. And I was like, yeah. And he goes, why don't you start doing that now? And it like, shook me. He was like, why wouldn't you start giving away some of your money now? So that you can impact your children, so you can feel the impact of it. And most of all, fuck that shit. Cause that's selfish. So that you can impact people now, not 40 years from now. And like, I don't know if you see these goosebumps, but I'm getting them right now.

[Interviewer]

Yeah, you are.

[Gary Vaynerchuk]

It just changed the way I looked at the world. And within a couple months I joined the board of charity Water. A few months later, I joined the board of Pencils of Promise. And you know, I don't talk. I don't. I'm very. I'm a little old school. Like, talking about your nonprofit work feels. I don't mind self promoting my businesses, but those frivolous things feel easy. Buy this wine, buy this beef, friend. But the real stuff I do is a little bit more behind the scenes. But joining those two boards, being involved in many different things has been incredibly impactful. And that is one moment in my life where I met someone randomly the first time I met them. And they changed the course of how I saw life.

[Interviewer]

What's a prediction you made that you were just totally wrong on? That you really believed I'm right?

[Gary Vaynerchuk]

That I thought that. I thought in 1997 with winelibrary.com that by the year 2000 all of you would buy everything on the Internet just

[Interviewer]

because of the number.

[Gary Vaynerchuk]

Yeah, I mean, 2000 was like, you know, again, it was a big number for all of us in society. What I didn't know in my 20s that I always push all of you that are trying to win is I didn't know timing of how long it took people to do the thing. That was obvious to me. Notice today with AI, I'll say it's inevitable. I won't say next year. Everyone's going to. I don't put years on it. Or if I do, if you look at some of my content, I'm like, live shopping like your cousin, right? You got it. You watched in a decade, in nine years. I did not know my. I don't really predict things. I only talk about things that are happening. In 97, people were buying on the Internet. Amazon was working. EBay was working. When I talked about TikTok, it already happened. It was called musical ly. I was all over it. Like, I don't really predict. It's. It's more that I know when things cross the chasm from going to a small group of nerds or a small group of cool kids and that it's going to go mainstream. And I try to figure out when that timing is. And so all my. If I was making content about business in my 20s, a lot of those receipts would be wrong because I was more emphatic of when. And all of my belief back then was fast. Got it.

[Interviewer]

Got it.

[Gary Vaynerchuk]

I would think that in a year or two this. In a year or two this now, I think in decades, not years.

[Interviewer]

What made you start v Friends? What was the moment where you said, I'm going to make the cards, I'm going to make the coins, I'm going to make, you know, the comics.

[Gary Vaynerchuk]

It was. It was the. It was Covid was what, 19 or 20?

[Interviewer]

19. But we.

[Gary Vaynerchuk]

I think officially we felt it in 20, right? So it was early 20 that I was seeing like NBA top shot, like seeing digital stuff. I'd heard about NFTs, not in that term. I heard about Moon Cats years ago. But I started doing homework in January. I was full pledged. And some of you remember this. I was full pledged a year before that. Trading cards were coming back, which made everyone like. Some of my smartest friends were like, hey, I think you're losing it. Because I'm like really yelling out of left field, by the way. I'm business marketing, investment, starting to get a little bougie cnbc. And out of nowhere I'm like, sports cards. And everyone was like, what and so I was watching sports cards, and I was like, fuck, I think this might happen. This might be the contemporary art of this generation. I was watching what was happening with sneakers. I could see that it was moving into sports cards. And I started talking about that. That led to people reaching out to me in early 20s, saying, hey, do you see this NFT thing? So in January of 20, and because it was Covid and I had more time at home to do more research than I'm accustomed to when I'm busy, I had the ability to really dig in. And very quickly, it became obvious to me that CryptoPunks was gonna be the NFT and I was gonna collect them. Like, I collect a lot of things. And then I was like, you know, for a long time, I've always wanted to be in intellectual property. I wanted to buy, like, Scooby Doo or Casper the Friendly Ghost and refurbish it. Right? Like, yeah. Like, you know what just happened the last four years, five years with Crocs. Yeah.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

Where for the 10 years, 15 years prior, it was corny as hell. And then they just got cool again four years ago, and now they're starting to dip again, but everyone was rocking them. Cole would rock, you know, like, cool kids would rock them. Well, that was cool in the 90s. Then it was dead for 15 years, and then it became cool again. I'm obsessed with that. Like, for example, this will land with a lot of you. I can't wait for supreme to come back. Like, it needs to be dead for another five to seven years. But in seven years, when it comes back, everyone's like, of your. Your era, even a little older than you is gonna be like, yeah, because that's just how shit works. So I

[Interviewer]

can.

[Gary Vaynerchuk]

Really soon, it might. It might Everything.

[Interviewer]

People wearing it.

[Gary Vaynerchuk]

Yeah. Respect it. You know, it. It kind of can be faster these days. Nonetheless, I always thought about that from characters I still believe about Popeye, Felix the Cat, Betty Boop, the Flintstones. I think all of. I mean, you see it happening, right? He Man Masters the Universe is about to come out as a movie. Like, it's nostalgia is wildly underpriced and misunderstood. It makes you feel. It makes you remember when you were a little fucker and life was simple. And that's something us grownups need. So anyway, I've always thought about that. When I saw the NFT thing in early 2020, I was like, wait a minute. I think I can build a world from scratch, not buy one using this infrastructure. And at that point, the Gary Vee brand. The content I was putting out was really working. But I knew that I couldn't reach all 8 billion people because I'm not everyone's cup of tea, right? Like no human can be everyone's cup of tea. But I wanted to push patience, accountability, tenacity, competitiveness. Be a fucking gangster, but don't be a fucking dick face, right? That's like the framework. And so I created these characters because I think Patient Panda and Empathy Elephant and Entrepreneurial Elf and Tenacious Termite and Competitive Clown can get to people and parents that I could never get to. And so it was just a mix, like a meal. It was my ambition to Selfish and selfless at the highest level. Befriends is selfish and selfless. It's selfless because I want to use these 250 characters to actually make the world better. Cause I think I'm talented enough to do that.

[Interviewer]

Who is Competitive Clown?

[Gary Vaynerchuk]

Who is he? Yeah, I can't tell you cause I haven't launched the comic book origin story yet.

[Interviewer]

Okay.

[Gary Vaynerchuk]

But Competitive Clown is a befriend and a popular one. He has a crazy origin story, but I can't disclose that yet.

[Interviewer]

Okay, that's fine.

[Gary Vaynerchuk]

So anyway, it's selfless because I do want these characters to actually bring. And this is why I realized I was more Jim Henson than Walt Disney. I think Jim Henson's universe, especially Sesame street with inclusion had really good agenda and really did a good job on us and like made us better kids, especially that era. But it was selfish because he was building a multi hundred million dollar ip. That's how Befriends is gonna work out for me. It's gonna be a very positive impact on society over the next half century. But it's gonna make me a lot of money.

[Sponsor/Ad Voice]

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[Gary Vaynerchuk]

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[Gary Vaynerchuk]

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[Interviewer]

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[Gary Vaynerchuk]

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[Gary Vaynerchuk]

Yeah, I mean, I'm very pro capitalism as long as it's not out of whack. How important is sleep for me personally?

[Interviewer]

What is your sleep schedule? How has it been your whole life?

[Gary Vaynerchuk]

I've slept seven to eight hours my whole life with a lot of sixes and fives when I travel. But it was funny when I was blowing up, a lot of people thought I was all about like just hustle. I was always fascinated. I'm like, do people listen to my words? Like, to me it's passion which leads to you wanting to do it and you gotta work extra if you're in a shit situation to get out. But I was never. There's no content out there of like me being pumped about four hours of sleep. Yeah. I mean, for me personally, the reason I'm such a maniac and such a gangster is cause I have so much energy when I'm on the field. I can only have that energy when I have at least seven. I'm a seven.

[Interviewer]

Get to bed.

[Gary Vaynerchuk]

I'm an 11. I'm usually an 11 to 1am Guy, but more 11 and 12s.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

And six. Seven. Wake up.

[Interviewer]

Six, seven.

[Gary Vaynerchuk]

Six, seven. How much do you splurge?

[Interviewer]

What do you splurge on?

[Gary Vaynerchuk]

Weird. Weird jerseys of esoteric athletes of my favorite teams.

[Interviewer]

Okay. That's what you collect.

[Gary Vaynerchuk]

I don't collect it even. It's like my splurge when I. I spend a lot of money on collectibles, but I don't think I'm splurging. I think I'm investing.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

Like when I buy a $50,000 Spider man card, I think it's gonna be worth 200,000. I don't view that as splurge. Splurge is when the New York jets take a seventh round running back and I get a custom jersey for 250 bucks when the kid might get cut before I even get to wear the jersey to the first game. So my. I don't splurge. I mean, I. I splurge on time.

[Interviewer]

What about jumping into the jets hot seat? If you owned it.

[Gary Vaynerchuk]

Yes, you do.

[Interviewer]

To make them better.

[Gary Vaynerchuk]

I think running anything is based about people. So I'm actually very happy with who the jets have right now, both on the business side. President and on the general manager. So ironically, like, literally, if there was a magic thing and I own the jets right now, it wouldn't change much. I actually think they have the right business side team and sports side team. I think Mooj has been unbelievable. So I think the best owners focus on what they can control, which in my opinion is who do you hire to be your direct reports? I think the one thing sports teams are not doing well enough is investing in their fans. So I think I would probably create a chief fan officer cfo. Cfo whose job she or his job would be to be psycho about actually giving a fuck about the fans, not fuck the fans. They have no say anyway. And I think that would really go a long way when things are not going well. Yeah, but I'm obsessed right now with Moj, our gm. I think he's doing a really good job. And that to me is how you fix it. The general manager is the linchpin because he or she is making the decisions on your coach and your players. And that's the fucking punchline.

[Interviewer]

Do you ever get sad, Gary? You ever get blue?

[Gary Vaynerchuk]

Yeah, of course. I'm a human, I'm not a robot. I mean, I think my perspective is really solid and I keep shit basic and that makes me happier by percentage. I get upset when I'm very concerned about the health and well being of people around me. I'll share something vulnerable. We had a leader in my company, one of the healthiest guys in our company. Worked out every day, had a stroke, a bad one, and has not been able to come back to work. He has young children and just like it shakes you, you know, Such a good man. Like, you know, it's the things that all of us go like, why would God do this? Right? I worry about my parents health, my children's health for sure. So I get blue if I let my brain go into fear, which I try not to, but if I do around the health and wellness of my family, that can get me cooking. I also don't like, I just don't like negativity and darkness. So like when I see somebody gaining popularity around selling a negative agenda, I get a little concerned, miffed. But overall I'm pretty optimistic that things will flush out. I'm incredibly optimistic about human beings, even though right now I'm disappointed that I think a lot of us are getting tricked around fear and selfishness. I actually think that there's a real light at the end of the tunnel. And so, yeah, I mean I keep my blues for very important, which is primarily the health and wellness of my family. And I will tell you, I'm glad you paused on that. Yes, sir. Gentlemen, how is your meal?

[Interviewer]

Oh, it's one.

[Gary Vaynerchuk]

Very good.

[Interviewer]

I couldn't even get into it. But look, Luigo, about the wine.

[Gary Vaynerchuk]

The wine was great, brother.

[Interviewer]

Amazing.

[Gary Vaynerchuk]

You want to join us in a glass, brother? No, I. I don't think I should. I have other customers. Okay, respect. And I don't want to get fired also. Is that the policy?

[Interviewer]

I don't know. You can have a drink.

[Gary Vaynerchuk]

The boss doesn't like me.

[Sponsor/Ad Voice]

You never know.

[Interviewer]

Here, Luigo, have a little sip.

[Gary Vaynerchuk]

No, I don't think I should.

[Interviewer]

All right. It's good.

[Gary Vaynerchuk]

Enjoy your meal. Pass the test. Thank you, sir. I'm glad you paused on that. Just to go back on that, I will say this. And it's like, real fucking talk for everybody who's watching. If you're able to simplify, it just changes everything. Because to me, it's been very simple. Money made, money lost, notoriety gained, being in a slump, people talking shit, people praising you. If none of that is really meaningful, when you compare it to, think of your highest high or your lowest low, professionally or reputationally, how does that feel in comparison to something really actually happening to someone you really love? Even though things are going well? And that's basically how I've trained my brain. I think in life, you find what you're looking for. I like the way you pause. Because you're young, and I have a real passion. If I can get the youngsters to understand, like, all the shit you're crying about as you're watching this right now, it really doesn't fucking matter. Not in the scheme of things and life, you know this. It could fucking change in a heartbeat. I think everyone just takes themselves so serious. Did you watch the Kevin Hart roast?

[Interviewer]

I love Kevin Hart.

[Gary Vaynerchuk]

Me too.

[Interviewer]

I didn't see it.

[Gary Vaynerchuk]

Okay. Like, something. I watched it the other night. Something really struck me, which is, like, those who can laugh at themselves for real, are fucking winning. And just. I don't know, everyone just thinks they're fucking too cool, which just means they're too insecure. And I just wish the world can get a little more simplified.

[Interviewer]

What was the darkest moment that you pulled yourself out of, where you were, like, really stuck in it? You couldn't really move, and you were like, okay, I gotta stop.

[Gary Vaynerchuk]

That's a really good fucking question. I would say, being transparent about something I haven't talked a lot about. I would say that there was a moment where I started to resent my father, because I built a very big business for him, and I wasn't getting any of the money. And, like, I was young and so And I'm an immigrant and I signed up for running the business, not with him. He didn't ask me myself. I decided to join the business because I thought I was Kobe and LeBron and could do it as a kid and wanted to build a big business for my parents as a thank you and knew later on I could go do my thing. The reason I keep telling all you fuckers, be patient, you know, all the jokes people make of me, like, when I'm like, you're young, you're young. At 34 years old, I didn't have a fucking penny. So of course I believe that, that you have time. So anyway, in my late 20s, early 30s, I had started a family and I had no financial means of any kind of sort of. Especially compared to the impact I had created. And so it was a challenge, a child's inner challenge of how am I gonna do multiple things? How am I gonna get myself out of resentment? Because that's fucking garbage. How am I gonna get myself out of this and go do something else? I'm the whole fucking company. I can't fuck my dad. What do I do? And so, you know, I really built up the team around me. Huge shout out to my best friend, Brandon Warnecke. I elevated his skill set to be able to me to start doing more with my brother and vaynermedia. And, you know, I just kind of. It's kind of why I talk so much about lack of complaining and accountability. Let me tell you what I didn't do. I didn't do what so many people are doing right now, which is fucking bitch and cry like a. I didn't complain. I just fucking went in my cocoon and decided what moves I had to do. Knew I was gonna have to eat shit.

[Interviewer]

You're about to look.

[Gary Vaynerchuk]

Oh, I see it. The cake. Chocolate.

[Interviewer]

Yeah, chocolate.

[Gary Vaynerchuk]

And, you know, worked for two, three years to set myself up to be able to give me the flexibility. And I pointed thumbs instead of fingers. I didn't blame my dad, my mom, the world, capitalism, the president.

[Interviewer]

I don't even fucking like pointing thumbs instead of fingers. I like that because it's like, yeah,

[Gary Vaynerchuk]

bro, it's pretty good. Do you understand what's going on out there?

[Interviewer]

No.

[Gary Vaynerchuk]

It's Trump's fault, it's Biden's fault, it's Republicans fault, It's Democrats fault, it's capitalism's fault, it's socialism's fault, it's immigrants fault, it's. It's white dudes fault. When the fuck is it your fault? That you fucking suck. I know. And so I was in this shitty spot. It wasn't my dad's fault. He didn't make me. It wasn't North Korea, it wasn't slavery. I wanted to be a noble man and build this thing for my parents. Now I'd done it. Now I had the circumstances and the ramifications of being in an immigrant business.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

And so I had a fucking bite my cheeks, bite my tongue, not cry, and start figuring it out. And the way I did that was build up everyone around me that I felt good enough that I could step to the side and do something else. For the first two years of VaynerMedia, I was double CEOing. I was running the wine store and running Vaynermedia. Those were long 15 hour days for a couple years. But there was no way out of my perceived. There was no way out of doing right by my dad and mom and doing right by me other than going through. You know, I think about, you know, Rocky IV when he's in the snow. Yeah. The fucking log. I think about that fucking scene in Russia. Like, no pain, no gain, that stuff. Like, I really believe that. I don't understand why everyone has decided life should be a piece of cake. Speaking of cake, what a set, right, bro, I set you up. I didn't even think of that. All right, Luigi, let's do it.

[Interviewer]

So these two slices of cake look identical. Correct.

[Gary Vaynerchuk]

Is one cake and one's not.

[Interviewer]

Okay.

[Gary Vaynerchuk]

Is it that game show?

[Interviewer]

It's kind of like that. So one is cake and one is completely made ingredients as well, using generative AI.

[Gary Vaynerchuk]

Amazing.

[Interviewer]

So one is made by a chef, classic baker style, and one is just truly made 100% on the computer.

[Gary Vaynerchuk]

Okay.

[Interviewer]

Using Claude code and using. I don't know what the other system was.

[Gary Vaynerchuk]

Open claw. I think probably a harness.

[Interviewer]

So I want you to try both. Are you allergic to anything?

[Gary Vaynerchuk]

Nothing.

[Interviewer]

Amazing. So. And we have another one too.

[Gary Vaynerchuk]

That's a whole nother thing. Being allergic. I'm kidding.

[Interviewer]

So I want you to try a bite.

[Gary Vaynerchuk]

You got it?

[Interviewer]

And you say which one is. Yeah. Bakery. Which one is generative AI.

[Gary Vaynerchuk]

Should I use my hands or is Luigi gonna hook us up with a spoon?

[Interviewer]

We have a knife. There's no fork.

[Gary Vaynerchuk]

Luigi is coming.

[Interviewer]

Luigi. Let's see what he's doing. There he goes.

[Gary Vaynerchuk]

There we go.

[Interviewer]

He made these. Wait, let's do it again.

[Gary Vaynerchuk]

I'll take the pasta fork. I am not fucking fancy.

[Sponsor/Ad Voice]

Wait, can we do that one?

[Gary Vaynerchuk]

I will eat the pasta fork with the cake. I'm immigrant. We only had one fork back in the day.

[Interviewer]

Thank you.

[Gary Vaynerchuk]

These are your forks.

[Interviewer]

Oh, okay.

[Gary Vaynerchuk]

Only one fork in the house. Yeah.

[Interviewer]

We can't find.

[Gary Vaynerchuk]

You're lucky I'm an immigrant. This is how we did it. All right, tell me how you like the cake. The AI cake or the regular cake?

[Interviewer]

I don't know.

[Gary Vaynerchuk]

Do you want to taste each one? Yes, sir.

[Interviewer]

Taste each one and decide which one is made with AI.

[Gary Vaynerchuk]

Yep.

[Interviewer]

And it's not the recipe is which made with AI. All the ingredients, everything was generated. Okay, now try this one. It's an explosive. Don't worry about it.

[Gary Vaynerchuk]

That's the microwave. I feel like that was the A.I.

[Interviewer]

this one's the A.I.

[Gary Vaynerchuk]

this is the A.I.

[Interviewer]

you're correct. See, we're getting there, but it's very close.

[Gary Vaynerchuk]

Yeah, I actually prefer it. I'll keep the AI cake. You can have the regular. You got it.

[Interviewer]

Actually, Luigio, can we take these cakes and swap it out for the AI apples? Sure.

[Gary Vaynerchuk]

Oh, you have AI apples.

[Interviewer]

So we made. We've been training this model on trees from Brazil.

[Gary Vaynerchuk]

Okay.

[Interviewer]

And they make fruits that are pretty much identical. And we're gonna have the same thing again where you try two apples. One is real, one is completely AI Incredible.

[Gary Vaynerchuk]

Are we going to start a business around the answer?

[Interviewer]

The plan is. It's just seeing if it's realistic.

[Gary Vaynerchuk]

What are you going to call the business? I got one.

[Interviewer]

What is it?

[Gary Vaynerchuk]

How do you like them apples?

[Interviewer]

This guy's the best. That's why he does this.

[Gary Vaynerchuk]

It's brand new.

[Interviewer]

You know, I went to your office. I couldn't believe we got to talk about VaynerMedia.

[Gary Vaynerchuk]

We will. These are the apples that you requested. So you're telling me one of these is a real apple? A real boy?

[Interviewer]

One is a real boy and one

[Gary Vaynerchuk]

is AI One's completely AI down to

[Interviewer]

the stem and the seeds. And the seeds work okay. They don't grow big apples.

[Gary Vaynerchuk]

Fun fact. I really ate a fuckload of apples as a kid. Yeah, it was my mom's favorite fruit.

[Sponsor/Ad Voice]

Mm.

[Interviewer]

Take another bite of each, see what you like.

[Gary Vaynerchuk]

This is the AI apple. And this is the real apple.

[Interviewer]

You're wrong.

[Gary Vaynerchuk]

What?

[Interviewer]

You're wrong.

[Gary Vaynerchuk]

Get the fuck out of here. This is the A.I.

[Interviewer]

yeah.

[Gary Vaynerchuk]

Dude. Get the fuck outta here. That is the most insane apple I've ever had in my life.

[Interviewer]

Bro.

[Gary Vaynerchuk]

You're sitting on a billion dollar company.

[Interviewer]

So let's work on it. Okay?

[Gary Vaynerchuk]

Okay. Sorry. You all right?

[Interviewer]

This is Uber part two.

[Gary Vaynerchuk]

I'm not passing on this one.

[Interviewer]

Part two. Man, you went to a coin flip for half a million dollars?

[Gary Vaynerchuk]

Yes. Heads.

[Interviewer]

I hope I win this. You called heads for me.

[Gary Vaynerchuk]

No, I did not. You owe me half a million dollars.

[Interviewer]

Call.

[Gary Vaynerchuk]

I'm making you pay.

[Interviewer]

All right.

[Gary Vaynerchuk]

All right. Yeah.

[Interviewer]

Handshake agreement. You're gonna actually take that up with

[Gary Vaynerchuk]

legal and cause me problems?

[Interviewer]

We'll talk about it.

[Gary Vaynerchuk]

So you Rob Vayner's office?

[Interviewer]

Yeah, it was just I. You know, I know you from the Internet. Yep. I didn't realize the mass of the company, all the employees.

[Gary Vaynerchuk]

This is the funniest thing going on in my life right now. Like, all my friends make fun of me. They're like, you accomplished this business. Insane Empire. Vayner X, Vayner Sports, Vayner want my TV production company, VCR Group with the restaurants, v friends. All these things going on in my world, and no one knows about it because you're just the motivational speaker on social. And I tell them all the time. I'm like, that's fine.

[Interviewer]

I think it's fine.

[Gary Vaynerchuk]

You know, Like, I'm not building my companies for the accolades. I'm building them for myself, for my family, for my teammates that work with me. And so it is enjoyable when people come through and they're like, what the fuck is this? I'm like, my company.

[Interviewer]

Oh, it wraps around.

[Gary Vaynerchuk]

Yeah. I mean, we have Spiral. I mean, Vayner X, which is Vaynermedia, Chuck Media and Tamara Group, and Vayner Speakers. The four companies and the holding company, tingly Lane the Fifth. We've got 2,500 employees. It's, you know, it's a real business.

[Interviewer]

Real deal.

[Gary Vaynerchuk]

It's a real deal.

[Interviewer]

You started with your brother?

[Gary Vaynerchuk]

I did.

[Interviewer]

So what was. Tell me.

[Gary Vaynerchuk]

My brother was graduating college. He's 11 years younger than me. I was at that point that I just talked about where I was like, shit, I gotta do something else.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

My brother and I originally were going to do a fantasy sports business because we love that world. But then I started getting asked by big companies to come in and speak or consult because I had a lot of followers on Twitter. In 2009, I couldn't believe that I could walk into a big company that I loved, by the way, at the time, and still ESPN spend an hour pontificating about what I knew, consulting and get that kind of money. And so I walked out of Midtown office and called my brother. He was still at BU wrapping up. And I said, bro, I think we should start a consultancy is what I called it. Not even an agency. For big brands, because I think they're all starting to realize this social thing is going to go. And I think it's our easiest way, quickest way to getting some revenue versus a startup. And that's how VaynerMedia was born.

[Interviewer]

That's amazing. What was your first car?

[Gary Vaynerchuk]

My first car was a 1976 Monte Carlo with a huge dent in it, cherry red, that I bought at a garage sale for $550.

[Interviewer]

Wow. Did you flip it?

[Gary Vaynerchuk]

I did. I actually did. I actually made some money on that. Probably maybe like three years later for like 2,000 bucks because it was starting to get a little more classic. I should have probably held on to it.

[Interviewer]

Have you maintained friendships from college and childhood? You still talk to people?

[Gary Vaynerchuk]

That is my core friend group, yeah. The kids I grew up with. Yeah, I'm one of those.

[Interviewer]

And how often do you see them casually? How often do you get a call, you say, hey, let's eat some food and hang out?

[Gary Vaynerchuk]

Not a lot. I work too much. And then that means that my time then goes to family and then friends. My college friends live all over the country. My high school friends I see a little bit more. And then my jets and Knicks friends I see the most because I go to sporting events. And those are kids that are either from my childhood or I picked up along the way in our insanity of sports fandom. But for example, my college friends I probably speak to every day on the group thread.

[Interviewer]

Yeah. WhatsApp. IMessage.

[Gary Vaynerchuk]

IMessage. My friends are not very international. They're pretty ghetto kids.

[Interviewer]

Good.

[Gary Vaynerchuk]

Yeah. That's how we like it.

[Interviewer]

How important is starting a family for me personally?

[Gary Vaynerchuk]

Massively. You know, for the masses. I think everyone has to make their own decisions. But like, you know, I have two children. Anyone who has children can tell you, like, it's challenging and all the things, but like, it's crazy. Especially now. My 13 year old son is my best friend and he's like, it's so crazy to have someone you love that way, you know? And I'm very weird, in a good way. I'm in the small group of people who love their parents so much that the delta between loving their parents and children is not very great. You know, a lot of people unfortunately did not have the best parent situation. So when they have children, it's like this outlet. Right. For that love. For me, I'm sorry, fortunate that I have it on both sides, but there's just something. Do you want to have children one day? I would love to, yeah. I'm Trying actively.

[Interviewer]

Mm.

[Gary Vaynerchuk]

In a good way.

[Interviewer]

I don't know how you define good. Well, freaky as much as I can.

[Gary Vaynerchuk]

Yeah. And how's that going for you?

[Interviewer]

Not good.

[Sponsor/Ad Voice]

Why?

[Gary Vaynerchuk]

You have a great face.

[Interviewer]

Thank you.

[Gary Vaynerchuk]

We established that. Well, you know, might be this show might become this platform for you of real opportunity.

[Interviewer]

Yeah. I got. I got a woman I think is very special.

[Gary Vaynerchuk]

Oh, you're locked in. Ish. Locked.

[Interviewer]

Yeah. Like Paris style.

[Gary Vaynerchuk]

Yeah, I know. I'm proud of you. Anyway, when you have children, this part of the segment will make a lot more sense. It's truly, truly the a thing in life that you can think about it. You can think you're one of six siblings. You think you understand that you're the oldest of four other siblings. You're mature for your age, but until you have a child, you have no idea what that feels like. And then for me, I'm in this really cool chapter where when your child becomes your friend too. And you gotta be careful because I think one of the issues with modern parenting is trying to make your kids friends instead of being friendly with them and be their parent. But when your child has similar interests and you're hanging, it's fucking different, bro.

[Interviewer]

How motivated are you by love?

[Gary Vaynerchuk]

Very. I. In fact, if you break down this interview, I think most of what I've been talking about is I love love so much that I can't wait for it to become clear to a lot of people in the world that it always defeats hate. Cause right now people think hate's winning. You like sports? Not really. That's weird.

[Interviewer]

Sorry.

[Gary Vaynerchuk]

That's right. Let me explain to you sports, please. Sports is amazing because. Let's just use basketball. You could be down 18 going into the fourth quarter and you can win that game.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

Right now I think hate is leading love by 18 going into the fourth quarter. But I know love's gonna win when it hits triple zero. I'm very. Yeah, you know. You like Star Wars?

[Interviewer]

No.

[Gary Vaynerchuk]

What the fuck is going on here? What are you into?

[Interviewer]

I wasn't allowed to watch TV as a kid.

[Gary Vaynerchuk]

Is that true?

[Interviewer]

Yeah.

[Gary Vaynerchuk]

What were your parents thinking?

[Interviewer]

Nothing.

[Gary Vaynerchuk]

Hippie shit.

[Interviewer]

No, my dad works for FedEx.

[Gary Vaynerchuk]

Okay.

[Interviewer]

He loved shipping packages, stuff like that. My mom's a typist.

[Gary Vaynerchuk]

But why weren't you not allowed to watch tv?

[Interviewer]

I just didn't watch it.

[Gary Vaynerchuk]

Oh, you weren't. You were allowed to. You weren't interested in it?

[Interviewer]

Yeah.

[Gary Vaynerchuk]

What did you do? Well, I watched tv.

[Interviewer]

I didn't watch movies.

[Gary Vaynerchuk]

Okay. Respect. You were a TV show guy.

[Interviewer]

Yeah, Cartoons.

[Gary Vaynerchuk]

Cartoons. What was your favorite cartoon?

[Interviewer]

Ed.

[Gary Vaynerchuk]

Edd.

[Interviewer]

N. Eddy.

[Gary Vaynerchuk]

Yeah, of course. Classic. Anyway, sports love. Buzzer beater. I was about to say Star Wars. I think Star wars has it framed. Right? Which is the Jedi's versus the dark side. It's a thin line. They're both very powerful. Love and hate are both very fucking powerful. But fucking, bro, in the end, love is going to win and always does. I'm incredibly motivated by love. I would argue that I've put fucking 15, 20 years on wax on digital receipts of pure love, often packaged as motivation or business advice. But I'm who I am. I root for people. I'm even more of a lover behind the scenes of my content. Meaning I'll always be there for people. I always want to step up if I can. I want people to win. Even though I'm competitive as fuck, when I see other entrepreneurs, Mike, you know this. This is what's so interesting about the 1%. I'm blown away by watching other winners shit on other winners. Cause they're jealous because that winner made a little more. The girl's a little hotter. And I'm like, why? Why don't you have the capacity to know that you're fucking amazing and it's okay. And by the way, it's also a long game. Just cause someone's winning right now. Like somebody might invent some shit tomorrow or start a new business. I don't know. I just. I really root for people. I root for people heavy. I root for the extremes of people. People really struggling really motivate me. I want to get them the fuck out of that darkness. And then even what you may not know, Brother, is this 1%, 2% of winners, they're fucking unhappy too, man. There's a lot of envy, a lot of jealousy, a lot of like, am I washed up? Do I not like all this stuff? And so, yeah, I'm very motivated. Honestly, that was one of the best questions I've ever been asked in a podcast or interview in my career. I do not believe anyone has ever asked me that before. And I could argue it is my biggest truth. And by the way, I take no flowers for that. I am only motivated by that because I was instilled with so much love for my mom. Right? Like, I am just a carrier. I want anybody who just watched, I'd be like, that guy's cool. I'm not cool. My mom's cool. For putting that so deep in me that I don't even fucking know how to see the World another way.

[Interviewer]

You ever feel misunderstood?

[Gary Vaynerchuk]

Yeah.

[Interviewer]

What is something that you're like, come on, guys, hustle.

[Gary Vaynerchuk]

Like, we talked about it. There's just a lot of fucking people that think I'm like, hustle, hustle. I just never understood. That was always. That was because my energy of making my cut, like, I get it. Hey, mother. Like, I get it. But I was always fascinated at people's inability to see the words I was saying versus the energy. Because I'm like, do you like wrestling, my brother?

[Interviewer]

Did I know the references. Go ahead.

[Gary Vaynerchuk]

Okay. Like, most of the fucking content I make is like a fucking macho man, Randy Savage, fucking WWF promo cut. You know, like, what you gonna do? Like, you know, he's the bro. I'm proud of you. There we go with the pop. Yeah. That was unbelievable. He literally had a cup, Literally the plat. And then he had one that was even crazier when it was Mean Gene. And he was like, mean Gene, There's a plane going by and I'm not on it. I will say, I don't know why I thought that was so funny. Anyway. I think I'm misunderstood about that. I also talk predominantly about business and entrepreneurship. I am the most detached from my financial success and my notoriety success. And yet if I'm from the outside and I've spent no time knowing me, I would think that Gary Vee and how I do in business is my whole life that I understand. That's easy for me to understand. The Hustle, like, burn out at all cost to make money. That has been baffling to me that people take that from what you're saying. Yeah, yeah.

[Interviewer]

What do you think about depression as an excuse or.

[Gary Vaynerchuk]

No, no, no. I think many people weaponize mental health and depression because they're entitled and lazy, but I think there's an extraordinary amount of people that are actually struggling with chemical imbalances and real issues. In fact, this is not talked enough about in society, and I will use this massive platform to say it. I think one of the most alarming things going on in the world, and I think people should be ashamed of this, is people that are absolutely weaponizing mental health and depression and anxiety to be lazy are actually making it cloudy for all of us in society and making it harder for us to know who to help that's actually dealing with something.

[Interviewer]

You think medication's good or get through it in other ways.

[Gary Vaynerchuk]

I'm not educated enough to pontificate on the balance between spiritual work, meditation, food. I find it unlikely that some level of Medication doesn't work for some people. I think like anything, everything in balance is at its best. I think there's millions that are probably properly micro medicating and it's working wonders for them. And I'm so happy for them. And then I'm devastated to know that many are wildly over medicated and are probably double struggling because of that.

[Interviewer]

You struggled with drinking too much soda?

[Gary Vaynerchuk]

Yes.

[Interviewer]

Right?

[Gary Vaynerchuk]

Yes.

[Interviewer]

So what do you think pushed you in your life to. To pick up the cup?

[Gary Vaynerchuk]

That's a great question. I did drink in a shock. Do you know how weird my soda again? I'm immigrant. I used to when I was like 11, by my bed at night would be a warm 2 liter bottle of Coca Cola. And I would, you know, like when you wake up and like normal people might have a glass of water, all of us, I would literally swig from a 2 liter plastic. I mean it was fucking crazy.

[Interviewer]

Squeeze it at the.

[Gary Vaynerchuk]

Yeah, bro, the 80s were wild. Anyway, I will tell you exactly what made it happen. I was 38 and a half. I'm talking like I'm six and a half. I was 38 and a half. I was 38. Halfway through my 30 going on to 39. I was flying from Houston back to New York. I was just gave a keynote. I flew in that morning, spoke and left. Which is why I respect the people that fly in and fly out for work. And my head was on the window and I just decided that, holy shit, I'm not healthy. Like I don't work out, I don't eat well, and now I'm 40s right around the corner, I'm like, you know what? Fuck. And by the way, this has been brewing in my head, but this was the moment. I'm like, you know what? Fuck it, I'm gonna. On my 40th birthday, I'm gonna change everything.

[Interviewer]

On that flight you ordered two or three sodas.

[Gary Vaynerchuk]

It gets more interesting. I did not. And by the time I landed, three hour flight or so to New York, I decided halfway through the flight, I'm like, why the fuck am I waiting to 40? I'll do it at 39. And by the time I landed, I just talked to myself. I remember I was listening, I was listening. God, what was I listening? I was listening to something. I think it was little, I think it was Carter 30, I don't know. I was listening to an album over and over on repeat so that I could just think. And I just remember thinking when I landed, fuck it, I'm gonna start now. I called A former trainer, Mike Vacante, and said, hey, do you know anyone? Because I figured something out. I finally got to a financial place where I could hire somebody to travel with me. And I realized on that flight that I was not accountable to myself with health and wellness, But I'm very accountable to people. I love being a leader. I love being a leader for my employees. What if a trainer was my employee? I wouldn't want to let him down. That was my hack. I figured it out and it ended up. What happened? I called him. I said, do you know? Because he had trained me, like, I skipped like 30 out of 35 sessions with him, but he had a lot of clients. So I said, do you know anybody, a young kid like you that might want to be with me full time? And he said, what about me? I said, of course. So we got together the next day, and literally a week later, I started. And literally, for the last 12 years, I've had a babysitter. And the first thing that he wanted me to cut was soda. And the only thing I thought I was not gonna cut, I thought I was gonna be able to cut candy, baked goods, carbs. I thought pizza, fries. I thought I was gonna be able to cut everything but soda. And it was the reverse. The only thing I've been able to completely cut for sure has been soda. And I still like, when I break, I break for. I'm obsessed with soft carbs.

[Interviewer]

I love soft serve.

[Gary Vaynerchuk]

No soft carbs.

[Interviewer]

Have you ever seen a flying saucer?

[Gary Vaynerchuk]

Yeah, everyone has.

[Interviewer]

What are you eating a day now?

[Gary Vaynerchuk]

You know, this was weird. I tend not to eat until dinner. I grew up in a retail store, so I don't eat during the day, but I eat. You know, I try to have my protein. My wife is a very clean eater. Like, no oils. Like, everything's like, grass fed. No seed oils for her. No chemical. Like. So I've become very educated in the last five years. So I try to eat protein and veggies and the good shit.

[Interviewer]

Good. Let me see.

[Gary Vaynerchuk]

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[Interviewer]

The app lets you filter hotels by

[Gary Vaynerchuk]

neighborhood vibe, star level, and amenities like pools and spas and beach fronts and. Wait, I'm not done. Stop cutting me Off Priceline.

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[Interviewer]

And Austin, if any moment you want to do that knock and ask a question, I like the idea of, I mean, probably you feel comfortable doing, but like, it's just like a slow knock and you're looking forward and then you slowly turn around. But when you knock, the can't signal my feet. If at any moment when that does happen, just slide the paper across. What is your death row meal choice?

[Gary Vaynerchuk]

I just got done pontificating about clean. I think it's the last one. I think it's either Wingstop or White castle. Sliders.

[Interviewer]

Crave case 30.

[Gary Vaynerchuk]

Yeah, bro. I can crush that thing.

[Interviewer]

That's good. I love those.

[Gary Vaynerchuk]

They're so good, man.

[Interviewer]

Let's see.

[Gary Vaynerchuk]

They're so greasy. One second.

[Interviewer]

Okay, this is the last question. This question something and then. Yeah, or you want to ask it first? I'm just going to ask this. This question makes no sense at all, but answer it with such, like, seriousness, like, such intensity.

[Sponsor/Ad Voice]

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[Interviewer]

Okay. You know, I would argue today that the kids are much younger than they were when you were growing up and they got AI, smartphones, computers at home, computers in their bags. Laptops. Is it even possible?

[Gary Vaynerchuk]

Oh, it's very possible. They're the youngest we've ever seen their level of immaturity and they're like, wah, wah. Is. I don't know, like the 15 year olds of 30, 40 years ago were fucking 15.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

The 15 year olds of today are six.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

One plus five. You understand? Can you understand what I did there?

[Interviewer]

Yes.

[Gary Vaynerchuk]

One plus five, six.

[Interviewer]

So do you think that it's important to have a smartphone?

[Gary Vaynerchuk]

No.

[Interviewer]

Do you think smartphones are going to be here in 10 years? Are we going glasses?

[Gary Vaynerchuk]

I think we're going glasses within, I think the decade. That's the right number. Ten years. That's going to be huge for you.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

Because it's on brand. You've already locked in that you wear glasses.

[Interviewer]

Yes.

[Gary Vaynerchuk]

This is a huge competitive advantage.

[Interviewer]

And what should I ask Gary now?

[Gary Vaynerchuk]

A hundred percent, you know.

[Interviewer]

All right, Austin's gonna ask something. And then I think too, I think if you were looking for like straightforward, kind of like when you're doing that, like mysterious. Yeah. Like a knock, like a slow knock, and then you'll slowly turn all right. Should I be mid question? You cut me off.

[Gary Vaynerchuk]

I think it's a good. I think it's a good idea. Oh, he can edit.

[Interviewer]

Okay. Yeah.

[Gary Vaynerchuk]

Interrupt you.

[Interviewer]

All right. So I should knock still, right? I'll just be drinking wine. Slow knock.

[Gary Vaynerchuk]

Wait, wait one second.

[Interviewer]

Mic. That should start on. Okay, copy it. What's the point of it all?

[Gary Vaynerchuk]

That's a very.

[Interviewer]

No one appreciates anything at the end of the day.

[Gary Vaynerchuk]

Well, even you saying no one is you missing the point of it all.

[Interviewer]

And what's the point?

[Gary Vaynerchuk]

The point is making yourself happy with the ease and simplicity of life. If you're looking for outside validation, you'll always be stuck.

[Interviewer]

That's my cousin.

[Gary Vaynerchuk]

He's a good kid.

[Interviewer]

He's a great kid. I mean, he's here all the time. I try to tell him, hey, look, pursue it. He's a fashion designer. He's amazing. Did you know they don't appreciate all the hard work? They don't know all the hours it takes, all the days you don't want to wake up. You want to lay in bed, you know?

[Gary Vaynerchuk]

Yeah, but I think brother and I love you, and I think you're onto something. I'm telling you, once you get your sentences to not start with day and you start focusing your sentences on I, a lot can happen. Like when you make the design for you, when you create the hoodie or the socks or the scarf for you. Right. When you work for you.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

When you have. You understand.

[Interviewer]

I needed to hear that.

[Gary Vaynerchuk]

I'm glad, brother, because that's real shit.

[Interviewer]

It's the passion. I need to fall in love with it, creating, you know?

[Gary Vaynerchuk]

Yeah, bro.

[Interviewer]

That's what it started.

[Gary Vaynerchuk]

It oozes out of you, but where you're caught, and this whole generation's caught on, and by the way boomers are caught in it, too, is when it's they, you're fucked. Cause you're not in control of they, but you're very fucking in control of me. And I. You understand. You're welcome, brother. When you asked me that question, it, like, shook me. I was like, holy fuck. Like a part of me while I was answering you. I don't know how many of you have, like, two sides of your brain, but I was answering him, and another part of my brain was like, fuck. That might be the question that I've always asked someone to ask me, always wanted someone to ask me. I get asked a lot, actually, in podcasts and interviews like this. What's the one question you wish someone would ask you? And I never know. It's. I've never felt it. I'm always like, oh, I don't care about that. I just care about answering the questions for the audience. But when you fucking ask that question, I was like, fuck. That might be the question I've been waiting for someone to ask me. Because this whole love hate thing, this whole Star wars framework, you all know we're all living in society right now. Like, people are fucking angry and scared, and it's all been put in people's heads by a small group of people that are using it to control people. And it. And love is fucking liberating, bro.

[Interviewer]

Yeah, good. I'm glad. I'm glad.

[Gary Vaynerchuk]

I'm proud of you.

[Interviewer]

Proud of you.

[Gary Vaynerchuk]

I'm proud of you.

[Interviewer]

I love you.

[Gary Vaynerchuk]

I love you a lot.

[Interviewer]

I love you so much.

[Gary Vaynerchuk]

I love you much more than that.

[Interviewer]

I'm looking at this menu here. See if there's any dessert I want. But I was thinking, has anyone ever, you know, got. Have you ever gotten the feeling that someone tried to intentionally guide you into the wrong direction?

[Gary Vaynerchuk]

Yeah.

[Interviewer]

And you were like that, mother.

[Gary Vaynerchuk]

I mean, I would argue. I would argue. A lot of people have done that. Not in, like, some awful way, you know, when I got it a lot, actually. When I started in the wine business, there's a really famous. The first time I got real press, the Star Ledger in New Jersey, the Jersey paper. You know what I'm saying, Luigi? The Jersey paper, like, this is the New York Times and the Wall Street Journal of New Jersey, the Star Ledger. And they do a huge piece on me. It's a big fucking deal to me. I made it. I'm like 25, 24. And they asked me an interesting question. I told a story about a year earlier when I started running the wine store, the biggest distributor, the people we buy from came and met with me.

[Interviewer]

Me.

[Gary Vaynerchuk]

And he was like, the guy. Everyone thought he was the most brilliant guy in the liquor business. And he sat down with me over lunch just like this, and he said, kid, I think you got it. Like, he was gassing me.

[Interviewer]

Yeah.

[Gary Vaynerchuk]

He said, but you got to remember one thing. In a liquor store, there's service, there's selection, and there's price, right? How do you service the company? How many different incredible selections do you have in your store and what do you sell it for? And he said, remember, if you want to be successful, you got to be good at a two out of three of them. And he, like, left. And he was trying to make some big, profound statement. I was fucking 22. I'm sitting there, this guy's like, 60 at the time, legend, at least in the liquor business in New Jersey. And he walks away. I'm there by myself, just in my own thoughts for one second, and I'm like, the fuck's the matter with him? Yeah, I'm going to do all three. The fuck would I only do two out of three for? I told that story in the Star Ledger. They asked me, I think, what's the worst advice you ever got? And I told that story. He sent me a handwritten note a week later after the article hit. And he's like, I know that's me. And like, you were right. It wasn't that he was guiding me in the wrong. He just didn't want me to become very big because then I would have more power in the industry. It was selfish, but it wasn't like, catastrophic. It wasn't like, come over here, kid, and do drugs. A lot of people, most people try to guide you into a place that's better for them. Keep you at bay, maybe. Or they have a hole in their heart and they need something from you or a million other things. I actually never get upset about that. I'm actually deeply empathetic to that. That is the flight of man. Like, people do worry about themselves. I don't judge that, but it never tricks me.

[Interviewer]

I love it. Thank you, man.

[Gary Vaynerchuk]

Thank you. Hey, everybody. 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.