In short
How to build confidence through two extremes—“nothing to lose” creativity and “incredible depth of knowledge and conviction”—and how that mindset drives marketing innovation, brand-building, and adapting to AI.
Guests (and backgrounds)
- Gary Vaynerchuk (Gary Vee): wine-industry entrepreneur and marketer; ran Wine Library TV (first YouTube episode Feb 21, 2006); later built VaynerMedia; worked across direct-to-consumer wine, grape buying, restaurants, and “Wine Text.” Grew up in a New Jersey liquor store; became a wine collector at 15.
- John (host): ad/marketing professional; references working in advertising and agencies; discusses “oak monster” and brand/consumer humility.
Key claims
- Confidence comes from either removing fear (nothing to lose) or mastering substance (knowledge).
- Wine and marketing should “tear down the establishment”: teach people to know what they like, not feel intimidated.
- Great brands build community and culture, not just messaging; consumers aren’t stupid—Fortune 500 often disrespects them.
- Media “reach” is often fraud; creativity requires humility and execution.
- AI is an opportunity that still needs humans; the barbell shift is extreme digital vs extreme analog.
Notable examples
- “Oak Monster” (criticizing overly oaked Napa wines; “replicate for 30 bucks”).
- Cold email consulting ESPN via Twitter followers.
- Early e-commerce/email for his father’s liquor store (1997) and later social-platform shifts (Facebook/MySpace/Twitter/YouTube).
- Uber as “selling time” and perception of time.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Courage to be Creative
0:59 to 2:29
Exploration of the two extremes that can foster creativity: having nothing to lose and possessing deep knowledge.
“The thing I love is I got to know you obviously through when you were doing wine.”
Gary's Journey in the Wine Industry
2:29 to 4:34
Gary shares his background in the wine industry and how he revolutionized people's perception of wine.
“But I've literally secretly run that wine business every day since I've left.”
The Evolution of Wine Culture
4:34 to 6:02
Discussion on the evolution of wine culture and the shift towards non-alcoholic wines.
“and when I realized people collected wine when I was 15.”
Breaking Down Barriers in Wine
6:02 to 8:02
Gary discusses how he aimed to make wine accessible and less intimidating for new drinkers.
“Because that's what was great about it, because you had that depth.”
Marketing Evolution and Observations
8:02 to 9:40
Gary shares insights on his marketing strategies and the evolution of consumer behavior.
“You take this, there you are, hugely successful.”
Building Brands and Movements
9:40 to 13:32
The conversation shifts to the importance of brand building and creating movements beyond just selling.
“And so my sense in 2009 when I started VaynerMedia was that social, that Amazon, that Netflix, that these were going to have profound impacts on the biggest companies in the world from a marketing standpoint.”
Challenges in Marketing Products
13:32 to 14:00
Gary elaborates on the challenges faced in marketing products and the balance between perception and reality.
“This was, you know, again, I'm getting the goosebumps.”
The Role of Great Brands and Products
14:00 to 17:19
Discover how impactful branding and product quality contribute to success.
“It was bigger than, because the brand is great, absolutely.”
Consumer Disrespect in Fortune 500
17:20 to 21:00
Learn why many corporations may overlook consumer value and quality.
“Well, also the other thing, too, is corporations often, the first thing is profit.”
The Importance of Time as Value
21:01 to 23:08
Explore how saving time can be a significant selling point for products.
“I don't know if a lot of women slash men that are listening right now even realize why they love Dyson, but I'm about to point to something that they might be like, oh my God, that's why I love it.”
Show all 21 chapters
Gary's Journey to VaynerMedia
23:09 to 27:46
Trace the steps that led Gary to establish VaynerMedia and his approach to marketing.
“So then you decide, I'm going to start VaynerMedia.”
Creativity and Business Success
27:47 to 28:00
Understand how creativity can drive business growth and client engagement.
“I knew that I didn't have to go to Cannes.”
The Power of Creativity
28:00 to 30:00
Explore how creativity connects with business success and personal power.
“And that's the power of creativity, isn't it?”
The Advantage of Being an Outsider
30:00 to 34:10
Learn how being an outsider can provide unique insights and advantages in business.
“When you're an outsider, you can break things if you're right.”
Navigating Change with AI
34:10 to 38:40
Understand the impact of AI on industries and the necessary adaptation strategies.
“And so, you know, you now have to constantly innovate.”
Creativity and Commercial Success
38:40 to 41:40
Discover the balance between creativity and the commercial aspects of business.
“Because you've got this thing there that can help you.”
Lies in Marketing
41:40 to 42:00
Identify common misconceptions in marketing and media that affect businesses.
“Yeah, again, knowing that a lot of ad people listen, this is more inside baseball, so I apologize to the general public that's listening to this.”
The Lies of Media and Creativity
42:00 to 43:19
Explore the misconceptions in media reach and creative directors' perceptions of their skills.
“The biggest lie in marketing, very nerdy, is on the media side is that reach that we talk about.”
The Role of AI in Creativity
43:20 to 45:31
Discuss how AI creates opportunities rather than just reducing costs in creative fields.
“in every ad firm great ideas can come from everywhere or anywhere that's kind of, have you ever read Marxism?”
Fear and Job Security in the Age of AI
45:32 to 46:59
Understand the fear surrounding AI and how it impacts job security for humans.
“He said, you know, AI really needs humans.”
Reflection and Closing Thoughts
47:00 to 47:55
A final reflection on the conversation and the importance of understanding one's career path.
“Yeah, I think that's a wonderful observation.”
Transcript
Automatic transcript. May contain errors.0:00This is for everyone who's listening who wants to push the envelope. I believe that you have the courage to be creative in two very extreme places. One, nothing to lose. There's just nothing to lose, so why not invent punk rock or be a modern contemporary artist in Manhattan when you're living in a shithole and you're just splashing stuff. And then on the other side, which was where I came from, was incredible depth of knowledge and conviction. By the time I did my first episode of Wine Library TV on YouTube in February 21st, 2006, I was 31 years old. I had spent pretty much my entire life since I was 15, which at that point meant more than half my life on studying wine.
0:41Even though I was going to be silly and do this stuff, there was no one who was going to walk up on me and outclass me in knowledge. Even though I was silly, no one, not the poshest sommelier in England or France or Italy was going to be able to come in and expose me for not having substance. This is the Gary Vee Audio Experience. I'm going to go straight into it. Please, Gary. The thing I love is I got to know you obviously through when you were doing wine. Yes. And it went like wildfire all of a sudden. And I thought about it. Because obviously, I am one of those incredibly stupid people who owns a vineyard.
1:25You're one of the smart people who sell the wine. Yes. Well, actually, the people in between are the smartest. They're the smartest. The retailer and the producer take the biggest risks. The biggest risk. The distributors make the most margin. And they're just peeing out. You know, they're fulfillment people. But what I thought was brilliant about what you did is that you changed the way people thought about wine. and I've always thought that's a sort of fundamental in driving great ideas is that you don't operate in the world that's there you change the way people see it and feel about it and that way you gain huge attention and then you decided I've done that but I think you're going back to it aren't you?
2:12Yeah I mean it's always around the reason I was four minutes late which I apologize to everyone I was literally talking to my best friend, Brandon Warnicke, who's kind of taken the reign of running the wine business, my family wine business, since I started Vayner years ago. But I've literally secretly run that wine business every day since I've left. And then obviously I had the direct-to-consumer wine brand. I got a little more into your world of being a producer. I didn't own the vineyards, but I bought the grapes. And so that was a very successful venture. In less than three years, we sold it to Constellation.
2:49It was a substantial exit. And then over the last four years, I've been in the restaurant business in a significant way, which has dragged me a little bit into the wine world, which has been fun. And then several years ago, I innovated for my father's business something called Wine Text, which is a daily text for a really good wine deal that has really revolutionized my dad's business again. So wine is always very near and dear to me. Yeah. In fact, one of the things I'm spending a lot of time right now is on non-alcoholic wine. Oh, yeah. That's a huge growing market, isn't it? And for gentlemen like you and guys like me, it's getting scary.
3:28And I use scary as a great term, as a slang term for, oh, my God, I think we're within the next five years going to see really high quality non-alcoholic wine, which I think will be very attractive to many consumers. So, yes, it's definitely one of the pillars. So you're still there, you're still doing it, you're still engaged with it. And, of course, it was your background. Your family had a wine shop. Yeah, I mean, it was a liquor store. A liquor store, I love that. It really was. It was a liquor store. My dad's store was called Shoppers Discount Liquors. But we had a very interesting location in New Jersey.
4:06One side was, like, very blue-collar. one side was very white collar my dad had a liquor store before the one that I grew up in smaller in Clark, New Jersey very blue collar so my father was a blue collar you know, merchant beer, liquor, pints, cigarettes you know, wrapping papers when I didn't even know what the hell that was but I noticed as a teenager that people were asking for wine and I was a collector in trading cards and comic books and toys and when I realized people collected wine when I was 15. That changed everything for me and that's what I wanted to build. But it was funny when you were talking about creativity, breaking the rules.
4:49You have an incredible career in that. I'm building one. I was thinking as you were talking, what allowed me to do what I did in the wine world when I was so entrenched for being a very posh? I remember when Jancis Robinson flew from England to be on my wine show in New Jersey. I gotta go watch the clip it was a very watershed moment even Robert Parker even though he was American it was definitely an upper brow play the answer, and this is for everyone who's listening who wants to push the envelope I believe that you have the courage to be creative in two very extreme places one, nothing to lose there's nothing to lose so why not invent punk rock or you know or be a modern contemporary artist in Manhattan when you're living in a shithole and you're just splashing stuff and then on the other side which is where I came from was incredible depth of knowledge and conviction by the time I did my first episode of Wine Library TV on YouTube in February 21st 2006 I was 31 years old I had spent pretty much my entire life since I was 15 which at that point meant more than half my life on studying life even though I was going to be silly and do this stuff there was no one who was going to walk up on me and outclass me in knowledge even though I was silly no one not the poshest sommelier in England or France or Italy was going to be able to come in and expose me for not having substance.
6:37Because that's what was great about it, because you had that depth. You really did connect with that depth of knowledge. Yes. But you talked about it in a kind of such a different way that it actually, not only did you enjoy watching it, it was fun watching it. It was like a sort of entertainment. It was entertainment, wasn't it? You know this, and I think this translated well for me in the advertising industry. I wanted to create net new drinkers. I wanted more people to like wine. I was 31 years old and I had no friends in their 20s and 30s that liked it because it wasn't cool. And even if someone stumbled into it because they went on like a trip to Napa with their girlfriend, they're like, oh, I like this.
7:20As soon as they came back to New York or New Jersey or Chicago and started to try to go on a journey, everybody in the wine world made them feel like crap. Everyone's intimidated by wine. You know, when we go out to eat a nice meal, we're not scared to order salmon. We don't feel lesser than to order pork chops or scallops. But when the wine list gets handed, everyone shivers as if there's something you're supposed to know. And my point of view there, then and today, is you need to know what you like. And if you get into it, then you start studying a little bit and you learn stuff. Yeah, I wanted to tear down the establishment.
7:57man. That has been a consistent deal. And that's a kind of consistency, isn't it, to everything that you've done. You take this, there you are, hugely successful. I mean, literally, I mean, I had people, several people said, John, you've got to watch Gary Vaynerchuk, you've got to watch, which obviously I did. I always remember the wood monster. Yes. The wood monster. The oak monster. The oak monster. Thank you for remembering that. By the way, I'm getting goosebumps. I'm humbled by you knowing that. The oak monster was a great one. You'll love this because you're from Europe. America, you know, we sometimes like things too big, too ridiculous.
8:29And our wines in Napa got way out of control in that era. Everything had way too much oak. You could barely even taste the wine at some point. And so, yes, I needed to make a point about that, and I created the oak monster. And so I would taste the wine that would get a 96 points Parker and be$150 a bottle, and everyone loves it. And I would say, yeah, but, like, you could replicate this flavor for 30 bucks if you put enough oak in it. Enough oak in it, yeah. And so, yes, I made a big point about that. That was great. I always remember that. But anyway, so there you are. You have this phenomenal success.
9:03You say, right, I'm going to take that and I'm going to transfer that over into thinking about how the media works. Yes. So you could have gone to another industry. You could have gone to anything to sort of say I'm going to apply that. I think you'll appreciate this, Skiddy, your background. I knew even when I was doing White Library TV, and again, I was 31 years old. It was about eight years after I'd run the business truly day-to-day. Started running it in 98. I knew that at that point in my life that I was a marketer that happened to be a businessman and salesman. And that what had really transpired between 2006 and 2009 before I started VaynerMedia was in that 11 years that I was running my daddy's business, I was innovating marketing-wise in a way that was profound, not only by the liquor store and wine industry, but by the general population of 8 billion people.
10:02And I started to realize that the biggest companies in the world were underestimating aggressively what was about to happen, which was, and you definitely know what I'm about to say, we had this incredible era when the world transferred from the radio to the television and I was a really poor student but I was pretty good at history and I was interested in it at the time I didn't realize why now I do understand turning 50 you know another 15 years of my career I do use history to tell me the future I love pattern recognition I understand human you know trends. And so my sense in 2009 when I started VaynerMedia was that social, that Amazon, that Netflix, that these were going to have profound impacts on the biggest companies in the world from a marketing standpoint.
10:56And I wanted to go learn. I knew nothing. When I started the firm, I didn't know about legends like you. But the other thing, first of all, you didn't do a marketing course, did you? And I think that's interesting, but you You saw yourself as a marketeer. You kind of had a sense of what was going on. Well, I had something better than a sense. I had results. Yes. You've done it. Yes. It's much better to be a great football player than to go to university and learn how to become a good football player. So taking that learning. There was something else there that you said, which is look at the history of things and you see patterns.
11:34You see patterns. and I do think we're in a kind of world where people don't try and look back to learn I always say, I went to art school and when I went to art school we were told there's a Rubens exhibition, you've got to go and see it, not that they expected us to paint pictures like Rubens but they said just look at it, have a kind of and I feel so much today, people have lost that context so they don't reflect on something and then understand how to push it forward, so there you are So you look at that and you go, this is going to really change. And I grabbed that moment. Yeah, I just, I had a sense that, you know, again, let's take a step back for the listener.
12:16I'd launched an e-commerce website for my dad's store in 1997. And that was just so wild. You know, a liquor store in New Jersey launching the first e-commerce wine businesses in America. That was just so left field. And I felt the effects of email marketing. You may know this. it was happening in the UK with Berry Brothers and others catalogs ruled the day in the wine business and print full page ads in the New York Times and the Wall Street Journal in America catalogs and I was able to outflank the Sherry Lehmans the Morels, the Zachies the premier wine shops in America by sending emails in the late 90s instead of building catalogs and I built this big web business and this big email business for my father and then Facebook, MySpace Twitter and YouTube came along in this three-year window.
13:06And I just sensed that these platforms were going to have equally a huge paradigm shift in consumer behavior the same way that email and websites did. So I already had my own experienced pattern recognition of like paradigm shift. I'm going to do this again. And this one was different because this was about brand building, not about selling. right? This was, you know, again, I'm getting the goosebumps. This was about brand. I was building my brand. I was building the business's brand. This wasn't sales, you know, pamphlets. This was information. This was education. This was affinity. This was entertainment.
13:47And the economic impact was enormous. So yes, I had a feeling it was happening again. And I think the other thing about that, which I love, is that it wasn't just about brand movement, we talk about this. You were making it into a movement. It was bigger than, because the brand is great, absolutely. You've actually changed the way people approach it. I think people like brands, but they like them when they have a profound impact and they show people a different way of doing something. If you look at the history of the great brands, that's what they did. They have a great product a lot of times.
14:25I think product sometimes gets forgotten. I had a meeting last week, you'll love this as an ad man, where we had this meeting and I looked at the CMO directly in the face and said, look, I think we're in our prime. We're in our prime right now. We're a really good firm. I have bad news for you. I think we can do a really good job in marketing this. The problem is we're going to speed up everyone knowing about this and I think your product sticks. I love that. What I was saying, and I said it tongue in cheek, but I did say it. and then I kind of jumped in and said listen what I'm saying by that is not that your product stinks I think you're 24 months away from people actually buying this and I also think you need to fix this and this and at least debate this and they were stunned because you know we're in the business of getting clients but they heavily appreciated it but I do think you're right I think great brands also ride on the back of a great product but then the point you're talking to which I very much agree with you is when you build a community around where the brand is taking you, well, now you're going to Nirvana.
15:37Yeah, that's where they be. You've made it a part of culture, but just to go back to that again, but I think it's such an important point you're making. And I sat in so many meetings, who's the creative person, I had to sell the work and stay in the meeting. And they'd be talking about problems in the Northwest or Northeast and pack promotions. and I'd always be sitting there going, have you ever thought about making a better product? And it was very interesting. I was talking to Jeff Rayner at Mammoth Brands and that's the first thing they do. Can we make it better? And then at least, and that's in our control.
16:11Correct, and gives you a chance. Yeah, that gives you a better chance. Other things are going to affect what you do, but nobody, they don't really sit down and think about, is this really, really better? Do I genuinely believe in it? I think most Fortune 500 executives disrespect the consumer. Yeah. I really do. I say that. No, I don't even say it humbly. I say it actually angrily. I believe that most Fortune 500 executives disrespect the end consumer. You know what I mean? Yeah, absolutely. They just sit around and they're like, we're just going to pound this message into their head and they're going to go to Saintsbury and buy it.
16:48We're just going to spend so much media dollars against this big idea. Listen, you and I, when it's all said and done and we're hanging out in heaven, we will be looked fondly upon in the history of advertising. You and I, on our best day, are trying our damnedest to come up with the idea, right? But we're human beings, and the industry has not accepted that that is calculated guessing, grounded in talent and history, but it's still a high-risk maneuver. and everyone in Fortune 500 land just thinks we're going to push it and on a product, I mean, I think a lot about with food, like people are getting more educated of what's in their products people are being much more thoughtful back to the non-alcoholic wine, the chemicals in food, I mean you guys have it better in Europe than we do in the US but like, I don't, I just sit in meeting after meeting and I'm like you know that people are not stupid, right?
17:46and I think we need more humility in ad land and Fortune 500 land and by the way this is more broad every entrepreneur and creative person that's listening right now please think about this please do not have audacity that the world should like your stuff because it's your stuff it's like the analogy I use all the time is everyone thinks their child's the cutest on the record most people's child is not the cutest child on earth because there's somebody else that's cute you know we go very subjective and our subjectivity is often grounded in selfishness. Well, also the other thing, too, is corporations often, the first thing is profit.
18:28So if I can make this cheaper, then that is better, rather than, could I make this better? And in the long term, that will be better for me. You know, I will say, I do believe we're in the early stages of people starting to feel it. There's a supermarket, if you call it. There's a store in LA called Airwad. Are you familiar with it? No, no, no. It's a very bougie supermarket. They call it like a Whole Foods, but like 10 times more expensive, 10 times cooler. I mean, they're charging$40 for a shake. And they're selling the cleanest bread in America for$22 when you can go buy bread for$4. And it's highly successful.
19:10You look at LVMH, right? Yeah. You know, I think that in the business world, I'm starting to think that people are starting to see, you know what? maybe if I make it$2 more but it's better and I communicate that that's actually a better business than this era that we had to drive everything to the lowest possible cost this Tesco, Sainsbury, Walmart era that I think is fine and I'm a capitalist I'm all about it I get it but I do think the consumer evolution is real I think unfortunately there's separation of wealth in a lot of parts of the world that are probably leading to some of this But I do think there's huge, for everyone who's listening, there's huge optionality on price and quality.
19:53There's a lot of ways to win now. It's not just the lowest price. It's not just the highest price. It might be a unique value proposition to the left or to the right, not just to the up and the down. It's given more optionality for entrepreneurs and creatives. It's interesting that because, I mean, virtually everybody we've talked to has talked about, I mean, James Dyson was fantastic about how I wanted to make a vacuum cleaner. that really was better. Yes. Technology, engineering. And then it had to look better. Yes. It had to look like it. Yes. And charges$100 more than his competitor. And we all know it has a hugely successful business because he has not only put quality into it, he's put engineering into it, and he's actually made it look great.
20:40And suddenly he goes, if I can clean it normally in a cupboard, I'll pay a bit more for that. So that value is something I think a lot of corporations miss. There's also something else that I think Dyson does that I think is wildly not talked about, which is it saves time. I think when you sell time, you win. And I will tell you that my belief of why Dyson has done both incredibly well in vacuuming, but also in hair and blow drying, is subconsciously. I don't know if a lot of women slash men that are listening right now even realize why they love Dyson, but I'm about to point to something that they might be like, oh my God, that's why I love it.
21:20Because it saves her seven minutes in getting ready. Because it saves her or him four minutes in cleaning the floor. Time is an incredibly important one. I must go back. I must get back. It's a really fantastic one. I mean, I agree with you. The engineering. All those things. But I'm telling you, for many of us, you know, I was an early investor of Uber, but I really blew it. I could have been the first investor at Uber. Travis, the founder of, well, not the founder. Garrett Camp actually invented Uber. They were co-founders. But Travis and I were very friendly at that time. I could have invested.
21:55I do not invest. I was actually, I went against one of my biggest principles, you know, scared money doesn't make money. I had less savings than I was accustomed to because I just bought my first big boy apartment in Manhattan. Bad timing. Because in hindsight, if I had the liquid, it would have ended up being the greatest investment of my career. So I don't invest in Uber, but it's being run by one of my best buds. And they come to New York City. In fact, in my office next door is an email from Uber thanking my brother, AJ, for taking the first Uber in Manhattan. We were right there. And in fact, in that first day that Uber was here, I watched, like the first day it launched, which was about a week after AJ took the drive, and I watched people taking Ubers in Manhattan, and I would watch cabs drive by people with the light on.
22:50And they were still waiting for their Uber. And I realized that Uber was going to be massive because Uber was selling time. It was also selling the perception of time. Now it seems mundane, but the fact that somebody could sit in a skyscraper like this, order an Uber, go downstairs and have the Uber there, in 2011, whatever that time was, whatever year it was, was profound. It was profound. And so, yes, I think time's a big one. Yeah. There's only so much of it. Correct. So then you decide, I'm going to start VaynerMedia. I was going to take that thinking of how into a kind of world that is dominated by being, you know, skyscrapers the size of whatever.
23:36But you went in with this view of, I'm going to change the way people feel or think. And you focused on this new thing, social media, social media. So you start that, pitch it. How did you get to the clients? How did you get to people? I had a lot of Twitter followers. Yeah. You know, because of the blind business. And again, back to what I said earlier about football. One of the things that makes me very unique in the history of advertising is I'm truly the practitioner of the craft that my agency sells. Think about that. Yeah. You know, again, it's so fun to talk to you about this. Today. Yeah.
24:16Today. Forget about when I started the company. Today, I will do more social media marketing myself. I write the copy to the team I write the copy to the team that I post on my Instagram content I'm a practitioner of the craft so anyway I had a lot of followers on Twitter and Twitter was starting to get important it was starting to be known right it started to make it into the BBHs and BBDs people had heard of it at least which was much better than it was two years earlier when I started on it and I it was very interesting actually I got a cold email from ESPN. And they said, we've been doing our homework.
24:58We're thinking about getting on Twitter. You have like 500 ,000 followers. Like, can you come in and consult us about Twitter? I'm like, I didn't get paid for this. So I came in. Is it good? And like, I knew nothing. No deck, no presentation. I just showed up and started talking. And all these fancy executives in ESPN, I'm such a sports fan. And these were like, wow, ESPN executives in the C-suite. And I, you know, I do have the gift of gab. So I walk in and I go one hour straight of just insane knowledge. And at the time, again, it would be like somebody walking in two years ago talking about AI.
25:36Like nobody knew what the hell I was talking about in the room. But I also, for my wine days, I'm very good at being, breaking down complex things in an average Joe way. And I think that's helped my career as a communicator. and even though they didn't really know what I was saying they did know what I was saying because I was making it contextual and at the end I didn't even ask how much they were going to pay me at the end they were like okay thank you so much and the check is going to be in the mail I was like how much and they're like$5 ,000 brother I thought I made$40 million I go downstairs I'm like I can't believe I just got paid$5 ,000 for that you know I grew up very humbly I grew up in a studio apartment the size of this room we're in right now with family members.
26:26You don't even know I'm building my dad's business to a big business. He doesn't pay me shit, so I'm making no money. So this$5 ,000 was like, so I called my brother, who's still in college but about to graduate, and we're debating starting all these different businesses. One would have looked like Groupon. Ironically, one would have been about fantasy sports. and I called him and I said hey I think we should start a company consulting the Fortune 500 so I just started making content more and more about marketing not wine and that just was all lead biz dev Bon and Bao who went on to have a pretty big career in advertising was at PepsiCo at the time had us stand up their PepsiCo account the NHL became aware of some of the work I did for ESPN we started the company in a conference room like this in Columbus Circle at another company that got famous in that era called Buddy Media.
27:16That's sort of the sales force. They had some clients they introduced us to, and kind of away we went. But I think the other thing there is that because you were engaging with it, you were opening doors. And I think that's how I always kind of say to people, do interesting things, and interesting things will happen to you. I think that's right. And not enough people are out there engaging, bringing the outside world in, affecting what you're doing, and then people suddenly go, we need to talk to you. I also knew that something most people didn't know that seems common sense now, but I knew I didn't have to go through Ad Age or the New York Times or the industry.
27:52I knew that I didn't have to go to Cannes. I could make content and it would come to me. I was living my thesis. What I wanted my clients to do, I was doing for my own business. And that's the power of creativity, isn't it? Because there you were creating content that people were connecting to. and that gave you power. 100%. You're talking to people and they're responding. You know, it's funny. I'm a businessman, but when I get into long evenings or deep discussions, I always associate much more to my curiosity and creativity than I do to my salesmanship or operational capability. I agree with you.
28:31I think it's been the beacon of things that have worked for me and the others that I admire. I think it's a very big gift when you can see things differently. and if you then on top of that have the ability to execute, because you know this, we've met a lot of creative people, but they can't execute themselves into their own pants. I've always thought, which you were, I've always thought being an outsider gives you greater perception. And I think if you look at a lot of great creative people throughout history, they've been outsiders, and it's that sense of outside looking in gives you a perspective as opposed to being part of the group.
29:08The very senior executive at Publicis who's gone out to do something else ran into me literally at Madison Square Garden, ironically, right there, and grabbed me and said, hey, you don't know me. I'm like, hey, John, nice to meet you. His name was John as well. He said, I just want to say something to you. He said, you know, we used to really make fun of you. And we really thought you were kooky and an idiot and all this. And he goes, I had dinner with a bunch of my old pals, you know, many in the C-Streets of the biggest companies. Well, many outside the industry now. And somehow it got brought up.
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29:36He got brought up. And the punchline of that little 10-minute chat we all had was it makes sense in hindsight that it took a complete outsider to actually disrupt our industry. And that, again, a great lesson for you. If you're an outsider, you have an advantage. Use that advantage. Can I say one thing on that? Go on. But you must deploy common sense. Here's what I mean by that. When you're an outsider, you can break things if you're right. What I worry about is like, oh, I'm an outsider, and you're just kooky about it, and you just think you're going to win because you're different, and you're forcing the different.
30:15The reason it worked for me in this scenario in Adland was I knew the truth. It was that the industry was putting something on a pedestal that was subjective, not objective. And in business life, things have to get objective. So if you're an outsider and you can see that there's a flaw or something that's put on a pedestal or a romance from the industry that is not grounded in truth. Wine. I knew that the wine industry, you know this, would complain about wanting more people to be into wine. But then yet, they would spend all their time being douchebags to anyone who wanted to get into wine. I know.
30:56I know. Thank you. I gave a talk at the Bordeaux Symposium saying, you know, lose the mystery and keep the magic. And, you know, I always said, you know, no industry grows by making people look stupid. Which, of course, the wine industry is number one. Yeah. Number one. Make you look stupid. So there we are. And unlike high fashion, no one aspires. Like, high fashion are also a bunch of douchebags. but people still want to wear Prada or Louis Vuitton nobody really you want to look cool with a bottle of wine but it's a different thing you can't have audacity when your addressable market isn't big enough the difference between arrogance and confidence isn't it you have to understand you know what the difference is?
31:45humility another thing that you said there too which I thought was good it's not enough to be an outsider but also to trust your own judgment, to be able to relate to things. And then say, I think this could be better. I think, I believe genuinely this could be better. In fact, you're talking about something I love to think about, don't talk about often, so I'm glad you got us there. Do you know that I don't guess? Do you know that in my entire 30-year career, I've never guessed once? And yet I've innovated so much, done things that people are like, how did you see that? I just stay very narrow I don't have the audacity to jump into things that I don't understand you know again this one seems left field I remember the first article ever written or mention ever written about VaynerMedia and me in the ad world it was some blog post that said wine boy thinks he can win in Madison Avenue it was a real razz but I enjoyed it first of all yeah yeah because I'm deep down I'm an athlete in my mind meaning I like getting booed on the road.
32:52You know, like, I'm the kind of athlete that like wants the opposing team to hate it. That gets me going. So I enjoyed that but I remember laughing at it to myself. I snickered. Like that. Two seconds to myself. I'm like, oh, they don't realize my whole life has been marketing. I sold wine by being the best wine marketer of a generation. So it was interesting and so I don't guess. I trust myself because I don't guess. I don't go into real estate being like, oh, like you need to know stuff. It's a lot easier to trust your judgment or your intuition when it's grounded in some truth of knowledge or experience instead of like having reverse audacity and being like, I can just randomly do something better because I like golf and I can run this golf company better.
33:40But what do you know about the golf business? Well, there's a great lesson there too. So many businesses have been started by people who care, who obviously, who actually care about what they're doing and what they're making. It isn't just, I'm going to start a business. I really care about this. And I think I could do it better. So again, it's bringing yourself into what you're doing. Express yourself. This is what it's about. So this is, you know, we're now, you know, seeing another big change with AI coming along. And so, you know, you now have to constantly innovate. that's going to be crucial to your success.
34:19And how do you do that? Do you have a process? Do you have a kind of way that you're approaching that? Yes, my process is I want to put myself out of business before someone else does it. That's my North Star. You know, I can't have this great run in this last decade of disrupting the ad world on this social first approach and then just because now I'm big, be like, well, this AI thing's a bad. I don't have the hypocrisy. Thank God my parents don't have that in their body and didn't pass it on. I don't have the hypocrisy to do it. So yes, I have a very big approach, which is the only thing I really do, brother, in life is pay attention to the consumer.
35:01I don't do anything besides pay attention to what's going on in the world. What are people thinking about? What's the temperament? What's trending? Why are people wearing baggy jeans again, like the 90s, versus tight jeans? Why are mustaches doing well versus not? What's going on? like what are people wearing? Why did hats grow? Like, you know, why are people traveling to Portugal versus, you know, like I watch every, why is this music working? What's going on with Korean and Latino culture and not just black culture in America? And then you go into Europe and different parts and Asia because we have offices everywhere.
35:32And so, you know, obviously about three years ago, I'm like, uh-oh, here comes AI. You know, and I was aware of machine learning and I have some very nerdy friends because I do a lot of Silicon Valley investing and it's been in the air, but I was like, oh it's here and so you know I think from my standpoint I'll tell you what I'm doing in black and white Vayner X my company we've gone very big into analog so I think that the rise of AI is creating this barbell effect extreme digital like extreme digital like there's like extreme digital right yeah and then on the other side the rise of extreme analog music festivals, sporting events, going to restaurants and checking in your phone, detoxing, Shabbat, Sun Friday from digital.
36:25Like just the extremes. A very bullish real life. I believe over the next five to 10 years, let's use 10 years, it's 2026. I believe in 10 years, it's obviously 2036, but I think the world will look more like 2050. I think it's gonna speed up very aggressively. However, I think that's going to create the rise of 1950. I think you're already seeing vinyl sales are up. Kids are asking for non-smartphones for their first phone. They're asking, not their parents. Gen Alpha sees the anxiety of Gen Z, blames digital, which I don't think is fully true. It's modern parenting, but we'll talk about that in another show.
37:06and so I'm so for us for example I don't know if you know this but Vayner's very unique we are a creative and media and strength like we're more old school when you do everything under one roof right? in addition we are a fully integrated experiential agency live shopping production a big wave that I'm obsessed with podcast production so I had a meeting two days ago with all 2 ,000 plus global employees and said, we are no longer an agency. We're a production company that happens to do agency work. All under one roof. So you've changed the way people approach it. I want everyone in my company, you'll find this fascinating given what you did for a living.
37:52Everyone in the company has to make. Yes. So even someone who has great ideas, like if you were you, me and you were together back in the day and I did this, yes I need your great ideas and then you need to tell me what you can physically make, can you sing do you want to draw because we make$5 ads like sometimes it's just a$5 production to put on social, sometimes it's a$500 ,000 but just ideas to a deck, to present is over so you're saying that actually unless you can implement I keep talking about AI. People keep saying it's a tool. I say it's not a tool. It's something you collaborate with.
38:36And if you collaborate with it, and then everybody in a sense is now a creative director. For sure. Because you've got this thing there that can help you. Really, really help. Now, what's going to be exposed in that is that not everyone is creative. Everyone has to... I say everybody's creative, but not everybody can do it. I can sing. Everybody can sing, but you really might not be a manager. That's right. That's exact. And by the way, even more optimistic, everyone can get better at singing if they put in effort. I fully believe that. When I say not everyone's creative, a caveat, especially for this kind of audience, you're more right than I am.
39:15Everyone is creative. Not everyone has the ability to be creative and execute in a manner that is commercially successful. And that is important to understand. There's a very different thing. inherently you know there's so many people i know that i mean my mother comes to mind what a wildly creative person in in fashion in home design architecture she can draw she does a lot of things well she does not come from a commercial lens it's for her insular bubble but she's doing what she loves. And in a way, I think that's the first step, because if you don't love it, why should somebody else love it?
40:02I agree with that completely. So, you know, you've got to say... In fact, let me say something pretty, might seem counter to what I've just been saying. I don't, I personally, me, which may seem wild, but stick with me here, I do not put creative commercial capabilities on a pedestal. I just think it is. In fact, I find, and I'm sure everyone who's listening will agree with me. Often the things we most love is creative and has no commercial essence to it. But I think the important thing is to get people to understand that they are inherently creative. And actually setting up a business is a creative act.
40:43Well that's where you're more right. You have to have an idea, you have to have a product, you have to have a service, what are you going to call it, what's it going to look like. All these things are creative acts. and getting people to kind of understand that and then to keep it going because obviously innovation is core to the success of, continuing success of a business. And creativity is at its core. And now to your point even more so, I believe emotional intelligence and resilience is my favorite form of creativity. Yeah. I would argue my greatest accomplishment creatively has been the creative conversation I've had myself around my optimism and world perspective.
41:23Well, I think creative people have to be optimists. Pessimism destroys creativity. There's nothing I hate more on earth than cynicism. Truly, I mean it. You've got to get out of rooms where people are being like that. It will destroy you. So, you've talked about what's the biggest lie in marketing. Oh, so many. Oh, jeez. Have you got enough time? Yeah, again, knowing that a lot of ad people listen, this is more inside baseball, so I apologize to the general public that's listening to this. Let me just get on my soapbox here because, boy, there's a lot of them. I would say a couple things. The biggest lie in marketing, very nerdy, is on the media side is that reach that we talk about.
42:11Like, oh, this is reach when you buy it. It's not being actualized. like when you buy a GRP or you buy all these impressions people aren't actually seeing it so the biggest lie is on the media side principal ad buying, there's real fraud in ad land it's really, it's kind of disgusting I would say now the other side of the equation, creativity I think the biggest lie is the lie that the senior creative director tells themselves that their creative skills subjectively are better than others I think there's an extraordinary lack of humility at the creative director level in Atlanta. Well, I've said this a number of times.
42:49I have a theory, and I've said this to people at BBH, that most companies are triangles, and the bosses at the top need details. I said, if you come to BBH, the triangle is inverted. I'm at the bottom. You're at the top, because you can have an idea that could transform the fortunes of our clients, our business, and everything. My job is to recognize that and make sure nobody gets in the way. That's right on paper. you could have put that into practice correct and in the ad world 15 years in now I will tell you in the same way that people love to say in every ad firm great ideas can come from everywhere or anywhere that's kind of, have you ever read Marxism?
43:29no I haven't actually I obviously know who you are if you read Marxism, if you read the concept of socialism and communism, what I was born in it reads beautifully but in practicality In execution, it's been disastrous. I will say that great ideas can come from anywhere. Being written on the walls of adverbs is similar to Marxism. The other thing you have to do there is that you have to kind of select the kind of people you've got there. You just don't let anybody. Of course. But again, you know this better than I do. I'm a newbie to this truth. The amount of times, you know, and I'm empathetic.
44:07You start as a junior copywriter. you eat shit for 25 years to finally get to the place to be the person that decides it's kind of hard to have the humility and the patience to let the ideas come from elsewhere listen, of course you did it well that's why you're a fucking legend but 99 % of people don't and I remind all my creative directors at every ad firm if you're so god damn creative go do it in the real world I was lucky, I got to work with Charles actually very in our first year in Avatar. Charlie has all kinds of issues. One thing he was genius at is that he loved the idea more than anything else.
44:49And if somebody else had it, he would move aside and go with that. Because in the end, he worked out it would make him more famous. By the way, it sounds like it makes sense to why he pulled off what he pulled off. Yeah. Again, that's a rarity. So we've got this, the future is, I'm being told here. We can go for like four hours, it feels like. Thank you, because I do have a meeting. Go ahead, sir. I'm just sorry. The thing that really fascinates me is I think people get AI wrong because they look at it and they go, it can take cost out rather than this creates opportunity. That's right. And I think somebody said something very smart the other day.
45:33He said, you know, AI really needs humans. Because with humans, it can really do some amazing things. And I think that is the future of it. That's the current of it, by the way. Well, I think it's such a lovely observation. Again, it inverts the way people are thinking. Well, listen, it's the way people think on anything new and big is fear. Have you ever read the history of what people felt about electricity? No. It's profoundly interesting. The term demonization got popularized. The reason we all know what the word demonized is, is because of how popular that term became. It happened before the electricity, but it got really into the culture when electricity hit this town.
46:18And JP Morgan had it down there, but almost everyone else was scared of it. Because the word in the street was if you let electricity into your home, you would also be bringing in demons. People are scared. Let's call a spade a spade. the reason everyone's up in arms about AI is they're scared it's going to take their job. There is nothing else. There's nothing else. And so to your point, when people realize you're not going to lose your job to AI, you're going to lose your job to humans that use AI if you are not one of them, the second that happens, then they start thinking of it like the typewriter or a computer or the internet or a cell phone.
46:59And so I hope people get there soon. Yeah, I think that's a wonderful observation. And I think, Gary, that's a great way to end that. I think this actually should be series one, because obviously we've got about another three series we could go on about. Listen, anytime you ask, I'm interested. I'm going to just sneak in some flowers. Anyone, you know, I have a good feeling a lot of people are going to listen and watch this because they come from my audience. Please, please take an hour to understand this man's career, what he did publicly, how he did it privately. Give yourself an hour. It's a North Star that many of you should aspire to.
47:39And anytime you ask, the answer is yes. Oh, Gary. Well, I'm now feeling embarrassed, but that is just wonderful. Thank you very much. You are a great conversation. And let's hope the Oak Monster doesn't come back. The Oak Monster, I remember that. Thank you very much. That was so good. 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 journey. See you later.
From the publisher
In this episode of The GaryVee Audio Experience, I break down the two extreme places the courage to be creative actually comes from — having nothing to lose, or having incredible depth of knowledge and conviction. I go back to the first episode of Wine Library TV in February 2006, when I was 31 years old and had already spent more than half my life studying wine, and I explain why no sommelier in England or France or Italy was ever going to walk up on me and expose me for not knowing my sh*t.
You'll learn about:
• The Two Extremes That Produce Creative Courage
• Depth of Knowledge as the Other Path
• Why Silly Works When the Substance Is Real
• How to Build Conviction Before You Press Record
