GaryVee x Stephen A. Smith: Adversity, Culture and the Future of Business

7 Sep 2025 · 22 min

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Podcast Summary: GaryVee x Stephen A. Smith - Adversity, Culture, and the Future of Business

Podcast Overview Podcast Title: The GaryVee Audio Experience Host: Gary Vaynerchuk Episode Title: GaryVee x Stephen A. Smith: Adversity, Culture and the Future of Business Episode Description: In this episode, Gary Vaynerchuk engages in a conversation with Stephen A. Smith about adversity, serendipity, and the essential elements to achieve success in the contemporary business landscape.

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Key Themes

  1. Adversity and Success
  2. Gary discusses how his background in the Soviet Union and upbringing in Queens, New York, instilled a sense of resilience and hard work.
  3. Emphasizes the importance of serendipity in his journey, attributing some of his success to fortunate circumstances.
  1. Points on the Board
  2. Gary defines "points on the board" as real achievements recognized by peers, not just accolades.
  3. Lists key accomplishments:
  4. Early investments in companies like Facebook and Uber.
  5. Transforming his father’s liquor store into a substantial internet business.
  6. Establishing VaynerMedia as a $350 million business.
  1. Cultural Relevance and Attention
  2. Gary elaborates on the evolving nature of attention and influence in marketing.
  3. Highlights the shift from traditional advertising (e.g., costly Super Bowl ads) to digital platforms like TikTok.
  4. Argues that many big brands waste advertising dollars, with only a small portion effectively capturing consumer attention.
  1. The Future of Business and Advertising
  2. Discussion on the changing landscape of media and advertising with the rise of digital platforms.
  3. Gary asserts:
  4. Traditional methods are losing relevance.
  5. There is an opportunity for innovators to capture attention and monetize effectively in the digital space.
  1. Substance vs. Numbers
  2. Emphasizes the importance of authenticity in content creation.
  3. Encourages creators to prioritize meaningful engagement over merely chasing numbers for short-term fame.
  1. Personal Ambitions
  2. Gary expresses his long-term goal of owning the New York Jets, mentioning the desire to influence positively and drive success within the organization.
  1. Collecting and Cultural Trends
  2. Predicts a rising trend in collecting (e.g., sneakers, sports cards) that will become a crucial aspect of cultural conversations in the future.

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Key Takeaways

  • Humility: Acknowledge your success but remain grounded and hungry for more.
  • Patience: Real success and recognition take time; quick fame may not be sustainable.
  • Substance Matters: Authentic engagement and belief in your message are crucial for lasting presence.
  • Change is Constant: Be prepared for rapid changes in business and media landscapes, adapting your strategy accordingly.
  • Positivity: A positive mindset can lead to innovation and success in a challenging world.

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Conclusion This episode of The GaryVee Audio Experience highlights the interplay between adversity, culture, and the future of business as Gary Vaynerchuk and Stephen A. Smith delve into the nuances of success in today's rapidly evolving landscape. Through their conversation, they emphasize the significance of authenticity, the value of patience, and the necessity of being adaptable in a world dominated by digital influence.

Final Thought: Embrace positivity and remain open to change; doing so may lead to unexpected opportunities and greater achievements.

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Transcript

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0:00This is the Gary Vee Audio Experience. When I'm out, whether it's on a lecture circuit or any place else, I got this famous saying, I'm brilliant because I know I'm not. I simply learn from those who are and I take notes and I do it from there. And that's a perfect segue into talking to my next guest, because this is a man described as one of the most forward thinkers in the world of business. He's a serial entrepreneur, a strategist, and is considered one of the leading global minds on what's next in culture, relevance, and dare I say, even the internet. The one and only Gary Vee, as in Gary Vaynerchuk.

0:42My man. What's up, my man? It's good to see you. It's such a pleasure. How you doing? Too good. When you hear yourself described in that fashion, tell me what comes across your mind. Similar to your opening line, deep humility. I'm detached from it a little bit. I'm detached a little bit from it. I get that I've worked really hard and I've earned and I got into a place where I can get some roses and some flowers because I've put some points on the board. But I think a lot about serendipity. Why was I born with intuition that led to me being right about a lot of things? Why was I fortunate to be born in the Soviet Union, come to Queens, New York with nothing and have the foundation of adversity.

1:25Adversity leads to success. I didn't pick when I was born. So there's a lot of serendipity that went into it. A lot of hard work. I'm not, you know, I don't think you just get there on vision boards. You got to do it. When you say points on the board, highlight and illuminate for folks what that means to you. What do you qualify or quantify as points on the board in your mind? Well, in my mind, points on the board is like what people talk about me behind my back that actually know me. That's the actual answer. Okay. And the way that I used it there, why do people look at me in a business world?

1:57I did invest in Facebook before people knew. I did invest in Uber before people knew. My brother took the first Uber in New York. I was early in this game. I did build my dad's local liquor store to an internet company in 1997 when people weren't even thinking that way. Grew from 3 million a year to 60 million a year in four years. Is that accurate? in seven. I did start VaynerMedia in an office of another company because I had so little money in the last 14 years. It is a$350 million a year business. So I've amassed my following. I've done work. I am a five-time New York Times selling best author.

2:33I am a very prolific public speaker that gets comped properly. So I put in the work, but when I hear that, it's nice, but I always want to not get high on my own supply. I'm still in the game. I'm trying to buy the New York jets. Okay. I'm far away from that. Right. So what I'm really doing when I hear that is nice. Thank you. Grateful to my mom and dad, really God, all that stuff. But, but still in pocket, still focused, putting nice wins on the board for my own self like this. You know, I I'm honored to be on this show. I'm a fan. Thank you so much. But then, you know, knowing that I want so much more.

3:13And being grateful if the God of life dropped down now and it's like, this is it, you cap in here. You're going to flat out, actually decline. I'm like, okay, that's disappointing. But I'm grateful for what I have, but I'm hungry for more. You've already made me a bigger, even bigger fan of yours than I already was because you talked about never getting high on your own supply. So you love Biggie. I appreciate that. You love the notorious B.I.G. Way to go with that. Way to go with that. Somebody just asked me what my, literally an interview I just did. They're like, what would you be your ideal real halftime show.

3:42I said, Bone Thugs and Harmony and a hologram of Biggie. That's the halftime show I want. Bone and Biggie is forever. I see you and people talk about the inordinate number of followers. I think it's like 45 million followers at the very least on social media. Why do you believe people follow Gary Vee? What are they looking for from you at this particular juncture in your life in terms of your interpretation? I think it's been ebb and flow. You know, my early base was because I was talking about wine and a lot of people were interested in it and I wasn't talking snooty about it So that was my early based when I really popped off in 2006 789 The economy was bad and I was talking like yo You can make money on YouTube and Twitter and people were confused by that And so early on it was for someone that was showing the way I think now it runs a lot of gamut I have a lot of people that follow me because I talk about modern parenting I think parenting is in a weird place in the world You know, I think a lot of people follow me for what's next because i've got that track record You know, it's funny.

4:41I think as a public figure, I'm very good at finding purple. I like that you wear purple a lot, by the way. I like purple. I think America's gotten too red and too blue. I agree with that. And I think purple is the magic. And so I think today, if I analyze why there's traction, I'm in love with purple. And I think people appreciate that because I think we're a little tired of the extremes. I'm looking at right now, just looking at some of your current companies, VaynerMedia, you're the CEO, global advertising agency that creates a lot of content for tweets, Facebook posts, Pinterest, Instagram, and others.

5:12Very next, you're the chairman, a combination of several media companies. Of course, Bain of Sports, all right? Full service talent representation and brand consulting. We might need to talk. We might need to talk one more. Okay, I say Empathy Wines, of course, direct-to-consumer winery. And that caught my eye because of the world that we're living in, moving from linear to digital, in television, in my world, which obviously everything is your world with what you're connected to right now. So as we sit here today and you're a visionary, how are you feeling about where we are as a nation, as a world, from an advertising perspective, from a global reach perspective, in terms of being an influencer?

5:49How are you feeling about this right now? Very happy. Why? Because I'm going to be historically correct. Okay. But what if you're historically correct about something very, very bad that you predicted? What about that? Well, I'm not predicting anything bad. Okay. In the context you asked the question, I'm the person in advertising right now that's saying 90 % of the money that big brands are spending is going in the garbage. I'm the one that's saying a$7 million Super Bowl ad is a bargain because 165 million people will actually watch your commercial. But during even the biggest sport, the AFC and NFC championship game, nobody was sitting around excited to watch the commercials in between the game.

6:29I'm the one that's saying TikTok this or streaming that. So what I'm trying to do is day trade attention. That's what I do for a living. And by the way, it's why I've watched your career for so long. I mean, we're going way back. I'm like, oh, this kid's got something. You know? Oh, this influencer. There's a reason Logan Paul or Charlie D 'Amelio or all these things that happened in my career. I'm watching underpriced culture, underpriced distribution, underpriced executors. And so in the way that you asked in the media landscape, I'm excited because things are about to change heavy. Okay. I was getting ready to ask you about that because I'm thinking about the merger that ESPN-Fox, the joint venture, I should say, not a merger, that ESPN-Fox along with Discovery, Warner Brothers Discovery got into.

7:14I'm looking at stuff like that. I'm looking at what their collective worth is compared to Amazon, which is in the trillions, Apple, which is in the trillions. The rest of those folks are in the billions. I'm wondering how you're feeling about stuff like that when you see it as a visionary. What's very clear is, and this is something I've been talking about for about seven or eight years, Apple and Amazon were not coming to fool around. These traditional media companies, including my favorites, ESPNs, all that, there's always a bigger fish. And the reality is the internet is the big dog. And so what happened was, there was all these people that held on to the radio when we finally had television in the 50s and 60s.

8:00I was a really poor student, Stephen A., but the one class I was good at was history. And I never understood until I got to my mid-30s. I'm like, damn, that's because I believe in pattern recognition and history repeating itself. And so what's happening is, what do I think? I think the world's going to change quite a bit. Apple has the MLS. Amazon's going to own this football thing. It's going to play out. And the NBA, and you know this because you're very close to it, they're not fooling around with this next deal. And there's a lot going on. And Ryan Smith with Utah Jazz is doing different stuff.

8:29And Matt Ishpia with the Suns is like, things are changing. And the way people are going to consume content and how they consume and where, you know this, a kid that's got talent, 15-year-old you, 19-year-old you, 23-year-old you, he now has TikTok and YouTube. He can build his audience. He didn't need people to put him on. People had to pick you along the way. People had to subjectively say you're a talent. And a lot, you know this, you came up with a lot of guys and gals. Some of them just didn't have the political luck of the draw. They didn't get picked, but there is no pickers anymore. Everyone goes direct to consumer now.

9:07Social media is not a ha ha ha joke. It is the foundation of everything. But is it just about numbers or it is about substance? I'm talking to Gary Vee and every word, every syllable that comes out of your mouth is about substance. And then I earn numbers. All right, and then you earn numbers. Now, numbers are important. Numbers are matter. I pay attention to them every day, make numbers think about it. But I also see people that are getting an exorbitant amount of numbers and they're getting it in a fashion distributing and disseminating content that I might not necessarily vibe with. Do I go for the numbers and throw that aside and throw everything else aside because I want those numbers?

9:39Or do I attach myself to the substance thinking that that's the long game that will ultimately reap the fruits of my labor? What's the mentality that somebody with that dilemma, what's the mentality they should grab? I believe, especially watching you from afar, it's an easy question. I understand even why you're asking me this question. It just depends on how you read the tortoise versus the hare. You know, to your point, I tell people all the time, you need to be out there. But if you're saying things you don't believe, it's not going to play out. Never. The end. It's a very simple game. the it all so in my content one of the things that annoys all these kids that gave me daps on the way to walk in here the one thing they'll tell you if you really talk to them the thing that annoys them is that i push patients so heavy and they hate it you know this the kids they want everything now when we grew up we were like maybe at 40 some things would click in they want everything now and but i don't blame world's fast i get it right but you can't do five push-ups and look like a g right you got to put in the work and so you know from my standpoint what would I say?

10:43If you want a couple of years of enjoyment and some fake fame and accolades, then attach yourself to anything and not be about real life. If you want legendary status, if you want it forever, and most of all, if you want to be able to put your head on your pillow at night, you better spit things you actually believe. Listen, in your business, I see these people all the time come and go, and you know they're in trouble because you know they don't believe what they're saying on right you know it yeah i can't i have no patience for the phoniness and so for me too like i can't do you know in advertising how disliked i am i'm sitting there and poking sacred cows i'm saying every television commercial is a waste of money besides super bowl i'm sure you can imagine that a lot of people in that 80 billion dollar industry per year in america they have feelings about their feelings that's right absolutely and so but i'm too scared to be wrong right how can you say things you don't believe but if 80 billion let's just say for example 80 90 percent of it is wasted time yes it's advertised yes right and we all understand that these are the kind of things that fuel the system i mean you can look at the criminal justices you don't even get me started with that you know you know police officers the lawyers the judges the prison system except the system itself we know all of this so anywhere you look anywhere you go there's always something systemic that has some level of influence right so when you say what you say do you ever find yourself looking at society and saying to yourself there's an abundance of people out there that are not equipped to handle the change that ultimately has come forward and how as a society you're going to adjust to that especially when in this scenario it's predicated on their own greed big companies go out of business because they care about the short term founders tend not to go out of business Mr.

12:34Old School Toyota isn't going to be the reason Toyota failed It's some executive that got paid and just wants to make their money on the stock price And so they'll milk it because they know they're retiring next year. Whoever gets left with the bag That's right. So in this scenario, the reason people keep spending money on Television commercials is because the four media companies that buy those commercials are publicly traded and they make money on buying TV upfronts and they don't care. So I get that. But the reality is it doesn't mean that these consumers are acting that way. And that's why there's always opportunities for kids and people on the come up because big companies play short.

13:13Humans, the right ones, play long. As we sit here right now, so many people in the business has looked at the transition from linear to digital. Yes. Not just in television, but in anything. Everything. And their mentality is that most people haven't learned how to monetize digital. Do you agree that that has been the case? No, I think big companies don't want to give up the big bags that they've figured out in traditional. Right. There's plenty of people that have monetized digital. As a matter of fact, there's way more humans that have figured out monetizing digital. But I'm saying those big companies that were making money in traditional, you can make money in digital.

13:51Why aren't you prioritizing really mastering how to make money in digital the way you did in tradition? Because at that level, those are nickels and pennies and dimes to the dollars they made in these big up front monster deals. And so they're secondary. Plus, you know this because you pay attention. The big dogs in these companies, they're not about that life. And so they make decisions based on themselves. It's the naivete of the game. They just don't see it. So your brilliance is obvious and it's well recorded and well documented. Riddle me this. Why the hell do you want to own the New York Jets?

14:30What is that about? Why would a winner such as yourself associate yourself and your fandom, your love, your emotions and everything else in between with the New York Jets? By the way, I haven't won a Super Bowl since 1969. January 12th, 1969. 68 season. January 12th, 1969. Best day ever. I was negative six. That's right. Negative six. Go ahead. Because I want to be driving the car. The most guaranteed way that I know I'm going to get a Super Bowl is for me to do it. Okay. And they say that you say you're not worth enough to purchase the New York Jet Shows. May I ask how much you're worth, sir?

15:12i mean if i liquidated everything and somebody thought that i would stay with the companies that i sold it to i could get into some real numbers hundreds of millions okay i mean hundreds of millions is very vague sir i like specifics i mean can i get like i'm trying to be a little bit more private with my life these days okay no problem but at least i asked look the jets are growing i'm i'm building too the problem is that these nfl teams are building fast too so look i I think I need a good 10, 15 years of real execution to put me in pocket to make a play. But here's the thing. And again, looking from afar, we don't know each other like that yet, but hope we do over the next decades.

15:52Absolutely. When you're ambitious, you're kind of just, you know, this is probably why you associate with athletes too. This is my assumption from afar. You know, when you're in your zone, I'm in my zone. Like I know I'm trying to get there. I also know there's a lot of serendipity that goes into it. I'm not in full control The johnsons may want to sell next year and it's over. I would have never thought if let's say my goal was to buy the Mavericks, okay I would have been cooling because i'm like mark's young Cubans not selling this for another two decades. I'm good. Boom It transacts So I need a lot of things that I don't control to happen to go my way I'm, just focused on building an empire to give me a shot sports.

16:33Yes, that's the jets but in your line of work, sports and culture are equally important. It matters to you. That's your future audience. That's what you're doing and whatever. How do you think they intertwine in this day and age? How comfortable are you with it? Oh, I think sports is one of the four to five pillars of popular culture. Like sports and music, fashion and food have had a good decade or two. Fashion, food, sports, music, and what else? You know what's the five? One of the five pillars. I got one that's really emerging. It's not there yet. Okay. I'm going to make a prediction because I want to look at this in 15 years and be like, okay, something crazy is going on with collecting.

17:08And I grew up with it, sports cards, all that. But then all of a sudden, man, if I knew all those sneakers were going to be worth this kind of money when I was coming up and then contemporary art. And just as, even if you look at the Taylor Swift effect in the Superbowl, here's a fun fact that a lot of people aren't paying attention to that I am. I'm watching little girls post Travis Kelsey rookie cards on TikTok. Yes. So collecting is starting. And I think in 20 years, when you go out to dinner, you'll just ask everybody the same way. What are you listening to? Oh, that new Kendrick Lamar. What do you, oh, Rasheed Johnson.

17:40When you're talking like collecting, I think people are just going to talk. They're collecting something. Got it. Two more questions before I let you get on out of here. Which clients of yours are running ads this year at the Super Bowl? We've got one, Starry. Okay. And we're really excited about it. It's proper. It's a good one. Best Super Bowl commercial you've seen in the last five years? let me give you my favorite one of all time. And then last five years, favorite one's very personal. Cindy Crawford, diet Pepsi and her Daisy Dukes. That was the day that I went from being a boy to a man. So that will always be number one for me.

18:19I was like, what are these feelings? I was like, I was like watching football, Redskins, Broncos, just chilling, being a boy. I was like, why am I feeling different things? So that was a quintessential moment of my coming of age. Last five years, you know, coinbase two or three years ago did that bouncing qr code okay i think super bowl isn't selling enough or being transactional if they want to put celebrities in they want to make us laugh if i keep telling my clients and i and they're still not there yet but i think in super bowl spots you should be getting people to download your app you should be getting them to buy stuff i still think this is super bowl 58 right that's right yeah if i'm a company that sells 150 item a sneaker, a technology piece.

19:02I'm saying my Super Bowl commercials like for the rest of this game, until the game ends, triple zero on the scoreboard. This$150 item is$58. I don't think we're collecting first party data. If you're paying seven mil and then you got to make something for some money, get that data because first party data, that's the game. Got you. Back to direct to consumer. I know we're wrapping up. Yep. When you, you are fully direct to consumer because you will be because it's an inevitable chess game. Something like that. You're going to want that first party data. It's nice to have 10 million followers on Instagram.

19:35It's a lot better if you had 10 million phone numbers and emails. I'm with you. Last question, real quick. I need a one minute answer on this. Gotcha. You leave here today because this will not be the last time you and I talk. Can't wait. I promise you that. What message do you want my viewers and listeners to get from this conversation that we just sparked with one another as we look forward? In life, you find what you're looking for. If you want negativity, you can find negativity on the news and social media all day. But let me throw you the curveball, Curtis Martin, my perfect guy to walk by, perfect guy to walk by.

20:12But if you are looking for positivity, it's all out there. And so your viewers, and I know your audience because I'm part of it and I watch how we all chop up of the things you say and things you get into, you need to start looking for positivity because you actually can. There's systematic things that are broken. Maybe your mom or dad was this. There was adversity everywhere, but you are actually capable in this internet world to do things. You just have to choose to. That gives, you know what? That gives us all hope for the future because if people choose to be positive, then the world will be a better place and we'll all be in a better position.

20:43That's basically what you're saying. And I'll really go one last notch because I know we're out. When you were met with positivity, you do not have to act that way in return. And I'm not even saying Michelle Obama go higher. I'm saying feel bad for people that come with heat. for somebody walk around and spend their time to tell you you suck do you know suck of a life that is yeah that so be happy you're not the one doing it my man one and only gary v right here with stephen a right here on the stephen a smith show over the digital airways of youtube lessons pearls dropped on everybody this will not be the last time i have a conversation with this man on this show i can promise you that because i love to entertain but i also love to educate and i just received an education i really appreciate it for gary v this is stephen a signing off until next time everybody peace and love

From the publisher

In this 2024 episode of the Stephen A. Smith Podcast, Stephen sits down with GaryVee to talk about adversity, serendipity, and what it really takes to succeed in business today. They explore Gary’s journey from humble beginnings to becoming one of the most forward thinkers in marketing and culture, while also digging into how attention, intuition, and hard work shape the future of business. A rare crossover conversation between two powerful voices in sports and entrepreneurship.


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