How to Scale Your Reselling Business with AI 

12 May 2026 · 49 min · 22 chapters

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In short

Scaling a reselling business using AI, and debating sneaker-reselling culture (celebrity negotiations, whether reselling is entrepreneurship, education vs “trenches,” and whether sneakers are “dead”). It also covers collectibles investing (comics, cards, vintage fictional character cards) and Nike strategy.

Guests

Gary Vaynerchuk (Gary Vee), entrepreneur/content creator and investor in reselling/collectibles; he discusses his “trenches” background and reputation-driven business. The other speaker is Joey (interviewer/host) and references “Gottsoul” and prior events; no detailed bio is given in the transcript.

Key claims

AI (“vibe coding,” tools like Claude) lets small operators act like “13 employees,” so learn it personally to judge quality. Celebrity/reseller price negotiation is normal in capitalism; both sides can say no. Reselling is entrepreneurship because it involves risk and running a business. College case studies can’t keep up with fast-changing markets; retail/real-world experience teaches better. Sneakers aren’t dead; they cycle and remain culturally important (e.g., 1985 Jordan 1 “Chicago” from ~$20–40k new to ~$10–15k now).

Notable examples

Meek Mill and Fat Joe negotiating for sneakers at Got Soul events; “Jordan 1 Chicago” pricing; Nike’s alleged mistake of damaging secondary markets and retailer relationships; Logan Paul’s Pokemon card sale; vintage Superman rookie-card speculation.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Importance of Learning AI Tools

0:30 to 0:58

Gary discusses the necessity of learning AI tools for scaling businesses.

“Every little kid now can sit and literally be in their room and have the power of 13 employees.”

Negotiation in Reselling: A Celebrity Perspective

0:58 to 2:30

Exploring the dynamics of negotiation between celebrities and resellers.

“The context on this one, you may have seen it on social.”

The Ethics of Capitalism and Negotiation

2:30 to 3:56

Gary details the ethics surrounding negotiation in a capitalist market.

“What two men or two women or a man and a guy do in a transaction deal is really ultimately none of our business.”

Understanding the Reselling Business Model

3:56 to 5:36

A deep dive into the business model of reselling and how it functions.

“But that needs to be pre-negotiated too.”

Resellers as Entrepreneurs

5:36 to 7:44

Gary argues for the classification of resellers as entrepreneurs.

“Yeah, I mean, again, other dealers are always worried that some precedent is being set that's gonna take away their money.”

Reselling vs. Traditional Education

7:44 to 11:14

Debating whether reselling provides better business education than college.

“I think I already know your answer to this, but people will definitely disagree, which I'm on your side.”

Leveraging Reputation in Business

11:14 to 14:01

The significance of personal reputation in gaining business opportunities.

“Let's keep going on this show but follow the podcast.”

The Evolution of Reselling: AI and New Tools

14:01 to 17:44

Learn how AI and modern tools have transformed the reselling landscape.

“you've been in the trenches you've done it all but you mentioned today's world is much different than we grew up especially when you grew up.”

Expanding into New Collectibles

17:45 to 21:47

Discover how resellers can diversify into various collectible markets.

“Like now with AI music, I'm like, I'm gonna have the number one rap album in the world.”

The Future of Sneakers and Collectibles

21:48 to 26:16

Examine the cultural significance and investment potential of sneakers.

“and people are putting together asset pools now.”
Show all 22 chapters

The Dynamics of Collecting and Flipping

26:17 to 28:00

Understand the interplay between collectors and flippers in the market.

“But you flip your way up to be able to go buy some things to invest in.”

The Landscape of Collecting and Flipping

28:00 to 29:20

Explore the dynamics between collectors and flippers in the resale market.

“Who am I to tell you that you see the world wrong?”

Nike's Current Challenges

29:20 to 30:40

Discuss the recent struggles of Nike and its market positioning.

“But that's okay because, like, you know, like, I'm surrounded by friends and family that are complainers.”

Potential Strategies for Nike's Recovery

30:40 to 34:20

Consider strategies that could lift Nike's stock and brand image.

“I think Nike got caught in a lot of different ways.”

Impact of Secondary Markets on Nike

34:20 to 36:00

Analyzing how Nike's actions have affected its secondary market and brand equity.

“They want to extract the value out of the secondary market which actually hurt them in the long term.”

The Evolution of Collectibles

36:00 to 38:10

Discuss the growth and potential of various collectible assets in the market.

“They have to rebuild that trust with both the retailers and with the collector community.”

Celebrity Influence on Collectibles

38:10 to 41:10

Examine how celebrity culture impacts the collectibles market today.

“I just did, where everyone was like, whoa, Gary V's not on, no, I'm not, like, I'm just still a human.”

The Importance of Hiring and Firing

42:00 to 42:50

Learn the significance of hiring quickly, firing as needed, and promoting top talent.

“We're seeing people be smarter and not just buy something because I tweeted it or Aoki or Logan Paul.”

Building Long-Term Success

42:50 to 44:10

Discover how prioritizing growth over immediate earnings can lead to lasting success.

“If you don't hire someone, you don't know if they're good or not.”

Impact and Gratitude

44:10 to 45:50

A heartfelt message expressing gratitude for mentorship and the positive impact on others.

“I want to say this, I mean this from the bottom of my heart, like someone who's looked up to you for a decade, right, and I remember we drove from Babson in a snowstorm just for you to sign those sneakers.”

A Message to the Fans

45:50 to 47:50

Gary shares a powerful message about the importance of kindness and optimism.

“That nothing you do professionally actually matters.”

Overcoming Challenges

47:50 to 49:16

Understand the need for practical optimism and the hard work involved in achieving success.

“because someone told you it's tough for your generation.”
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Transcript

Automatic transcript. May contain errors.

0:00Where is Daredevil? I'm right here. Don't miss the return of Marvel Television's Daredevil Born Again. So what's next? We're gonna take this city back. In an all new season, now streaming only on Disney+. They're hunting us. It's time we started hunting them. I can work with them. This should be tons of fun. Marvel Television's Daredevil Born Again, now streaming only on Disney+. Every little kid now can sit and literally be in their room and have the power of 13 employees. That's insane. So you have to become incredibly good at vibe coding or using AI tools to scale you to get better information.

0:44But what you would learn if you're 50 is like, I'm going to actually do it because I need to know it well enough because this is a skill that's going to be so important that if I always outsource it, I'll never really know it. So I'll never be able to judge it over the next 10 years. This is the Gary Vee Audio Experience.

1:28So don't hold back. I won't. The context on this one, you may have seen it on social. One of the most viral moments of all time at a Got Soul event is Meek Mill negotiating at our event and bartering for a pair of sneakers. The same thing's happened with Fat Joe. It's happened with other celebrities. And there's a huge discourse over should celebrities, rappers, famous people be negotiating with resellers for prices on their sneakers or should they just take the price? So should rappers and famous people be negotiating for their sneakers? It's none of my business. Here's what I mean by that answer.

1:56I obviously have seen that. In a negotiation, there's a two-way marketplace and there's an exchange happening. Some people, if they bought an expensive pair of rare Jordans, are gonna be as a reseller. And I've been, by the way, what's crazy is I've been on both sides of this. As a kid, there were people with clout and importance negotiating with me. And then I became someone who could do that. I don't I let me break this all down because I think everyone will agree with me that's watching. What two men or two women or a man and a guy do in a transaction deal is really ultimately none of our business.

2:37I understand we live in this world now where everyone thinks they should have an opinion about every fucking thing. I don't live that life. Here's why. The answer is yes or no. If I'm a reseller, if I'm selling something and Meek Mill is at my table and it's being filmed I may see that as an investment for marketing. Right. That was his argument. Is that his argument? Yeah. He's right. There are companies that pay Meek to wear stuff. Tons of money. The fuck is a reseller not doing it for his ability or her ability to clip it and run it for their business? On the flip side, if somebody in the comments of this said Gary, no, no, no.

3:19like I fucking worked hard. Fuck Meek Mill. Fuck Gary V. Fuck. I'm like bet. You're allowed to do that. On the flip side, Meek. He's allowed to be like yo give me this. He's allowed. Like in real life it's not like that's illegal. Now some people might have feelings about that. Why are you using your class? He might say well because I really think this person is getting value. It's also on the follow up. If I give Meek a free pair of sneakers, if Meek's then putting on seven emerging artists onto my shit and I become that dealer, well, that feels better. But that needs to be pre-negotiated too.

3:58I can't just assume Meek's gonna do that. In that negotiation, you can't be mad at Meek if you believe in capitalism. The dealer's allowed to say no. A lot of people have that. Do you know how many people on my come up ask me to do marketing for free because I needed them? everyone I said no every time because I knew I was going to become who I was going to become but in my pockets I've done stuff and a lot of times I'll do shit for free before the person even asks because in the micro I think it's worth it so long winded to your answer none of my business my opinion I'm agnostic I think it can and cannot work and I think every dealer and every celebrity or person with audience are allowed to do whatever they want.

4:48Got it. Okay. So no hard yes, no, it's okay. Well, because I don't think, I don't think, you know, I guess if you were like, Gary, I'm not letting you off the hook, I would say yes, everybody can do whatever the fuck they want. Okay. You know what I mean? Like, in essence, I think I am saying yes. You know, like, again, it's not like someone's punking him. Right. It's not like, Meek's not like, my bodyguards are gonna beat the fuck out of you if you don't give me this sneaker. Like, you know what I mean? like Meek's allowed to use his equity, which is his fame, to negotiate if he chooses to. Some people will look down on that and say that's not classy.

5:22I'm someone who puts out all of my marketing for free, like my best advice for free. Tons of people sell it. Close Discord, close Telegrams, fucking courses. Everyone's allowed. Right. So let him do what he needs to do. Yeah, I mean, again, other dealers are always worried that some precedent is being set that's gonna take away their money. Yeah. That's who's, right? I get that. And I think one other argument, and we can go on to the next. No, no, I'm interested in this. That was one part, was like, oh, don't use your fame, you know, it's bullying, you know, this, that. There's no bullying if the other person is willing to say no.

6:03Like, instead of bullying, how about, we're not talking about fourth graders in science class. We're talking about fucking people that's decided to buy a table and sell in a fucking commerce environment. Right. The other argument was Meek Mill's a multi-millionaire. He should just pay the price. I don't impose my opinions of what people should spend their money on. Right. I personally think he should. I think there's a lot of people that have that opinion that are dealers that make a million dollars a year that don't tip people. Right. Yeah. Like this concept of should, imposing your perspective on what is virtuous in the world on other people blows my mind.

6:38The same people that are Meeks a multi-millionaire that make$200 ,000 a year slinging jewelry, cards, sneakers and then fucking don't tip people at a restaurant are doing the same shit. It's all relative. It's all different scale. Again, I just, you know, unless someone's doing something illegal, I struggle to get into the virtues because virtues change. I believe in tipping. Not everyone does. They're allowed. They might have grown up in a different environment. I believe in charitable events. I'm very charitable. I don't publicize it but I write real checks. others don't others don't I do not think someone who's not into charity is lesser than me I don't want a peacock you notice I mean I bring it up now we're having a conversation but I don't make a lot of content about my charitable in fact I'm very quiet about it and I definitely won't judge another man or woman just because they have a hundred million I just I don't know when everyone decided they were God social media has done that no social media exposed that people sat in their kitchen tables and were God It couldn't be more true.

7:43Next one. I think I already know your answer to this, but people will definitely disagree, which I'm on your side. I know your answer. Are resellers entrepreneurs? Yes. A lot of people say no. They're just hustlers. They're just taking advantage of a market. They're not really an entrepreneur. They don't start a business. Well, I think it is a business. Like, if you buy and sell something, I mean, I think it's the actual depth. I don't know if anyone could argue, like, what's the, can someone like chat GBT or claw like what's the definition of an entrepreneur the official Webster let's play right now I mean in my mind it is to me it's you don't have a job you work for yourself you pay for your dinner and your rent through your money I view entrepreneurship as independent yes sir entrepreneur is someone who creates organizes and runs a business usually taking on financial risk in hope of making a profit that's it I mean how are you not taking on a risk you are not you know now Now, if you're saying I have a job and my side hustle is reselling, then you're both-ish.

8:43It's a side hustle. But anyone, in my opinion, if you listen to that definition, takes the risk. If your whole life, the way you pay for your roof over your head, the food on your table, is based on buying and selling product, if that's the definition of a reseller, well, I would argue that's an entrepreneur. Okay. And I would argue that it's an entrepreneurial venture if you have a job and it's your side hustle. anyone who's saying it's not first of all I don't think it means anything to debate I don't care if somebody thinks I'm an entrepreneur or not. There's also that for every reseller who actually cares if somebody else thinks they're an entrepreneur or not that's a whole other conversation for another day which is like who gives a fuck?

9:24Yeah I agree. Okay next one I think people will definitely disagree or agree with this one too you obviously have gotten in the trenches, you've done the garage sales, the whole thing, you've talked a lot about that hustle culture, reselling, you know, flipping world. Is reselling a better actually let me rephrase this. So is reselling a better business education than going to college? Yes. Because supply and demand and buying and selling and learning how to market and create sales and marketing DNA is a better education because you're doing and a classroom is listening. But I think working at a retail store as a cashier is a better education in business.

10:12And a lot of the business teachers now, I went to Babson, they say the number one entrepreneurship school in the world for 30 years, and I'm very happy that I went there, but a lot of those entrepreneurship teachers didn't even start a business or don't run a business themselves. Yeah, and I've spoken at Babson multiple times and other places. Listen, I love people learning finances. I think colleges do a good job. And by the way, it's not that I'm mad at college. I just think what you learn from college is very learnable in an AI back and forth today. And what you really need to learn is the trenches.

10:43Again, you can watch football film, you can read about football, but you have to get on the field and play football to be a football player. I really do believe entrepreneurship is like that. I'm not against the education. But you went to Babson. I go to all these schools and watch what they're learning. You're learning case studies and you're learning theories and you're learning good information of like this is what you should do but there is no should in entrepreneurship because the world changes. You were taught when AI did not exist. Right. Now what? Hey everybody, I hope you're enjoying the podcast right now.

11:15Make 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. Entrepreneurship is true sports. It's merit. The field changes. You can learn basketball but then Wemmy comes along and he's 7 '7 and he's got wing standing and you've got to play dip. I just believe in that when we talk about entrepreneurship and business. You have to adjust to the reality of the marketplace. I do not think college is built for creatives and entrepreneurs. I'm not against people going to college when their parents pay for it. I hate when creative or entrepreneurial kids go to college in today's environment and take on staggering debt.

11:53I do believe most real entrepreneurs will tell you they learned more in the trenches than they learned in school. It's not school's fault. you can't keep up with the market. Of course not. No, I completely agree. And I think it just boils down to just experience can't be taught. Correct. That's point and sound. Listen, I was destined to be a very successful entrepreneur. I had it. Fucking boy, I had it. The lemonade stands, the card shows. I learned in the trenches. But bro, Gary V, like me sitting here today against 25-year-old Gary who fucking built a monster business for his dad. I'm just better.

12:26You've been in it. I'm just too much inexperienced, too much pattern recognition. I figured out my kryptonites along the way like experience really fucking matters and unlike sports where your body breaks down like do you understand that if LeBron was still physically as talented as he was four years into the league what he'd be doing right now with his information but that's not how sports works out but it is how it works out in entrepreneur land you have no idea how much better you guys are going to be in a decade you're going to be like and I didn't really believe it when I sat in your seats meaning like I thought it was a natural talent like Kobe, like Serena, like, but it's very real.

13:03Well, I think everyone starts in a different point and then the time in is just gonna grow. Actually, let me stand on some business that I haven't historically. I've talked a lot about being a nice guy. You know, nice guys finish first, all that stuff I put out there, the propaganda that some of the players make fun of me for. It was funny, we were just talking, there's something else. Your reputation becomes your moat. One of the things that's going on with me now is just a lot of people in real life, not on social media, know how nice of a guy I am and that is giving me a lot of business opportunity.

13:35Right. Yeah. Cool. All right. Those are some of the hot topics. So that's another thing. I'm just saying it for all the kids. One of the reasons it's good to be a good person and not scam people and not fuck with people is when you get to 30, 40, 50, 60, 70, you're trading on your reputation. Right. That equity's enormous when you get to the big leagues. Yeah. At scale. At scale it matters. Cool. All right. You know? Yeah and you mentioned the kids and you also mentioned like tying all this in you know your past experience you've been in the trenches you've done it all but you mentioned today's world is much different than we grew up especially when you grew up.

14:08For sure. So I want to ask you how does someone become rich in today's world reselling? I mean it's easier than ever. Like I think about this every day. Like how dead I am that I didn't grow up in your guys' era. Like I would have fucked. Fuck man. I couldn't even imagine being 16 right now, vibe coding and using Claude and all these AI tools, using my insanity of passion, 15 hours a day being in the trenches, making relations, I mean, it's all the same shit. It's just super tools, right? Like I had flea markets and the malls of New Jersey. Then there was eBay, which I dreamed to wish I would have had.

14:48Then there was StockX and eBay. Then it was Discord and social and Telegram. And now it's AI. I mean, you've got to be AI usage. Like every little kid now can sit and literally be in their room and have the power of 13 employees. That's insane. So you have to become incredibly good at vibe coding or using AI tools to scale you, to get better information, to scale your relationship. I would sit down right now and create an app that automatically DM'd every person on earth. Oh, I'll pay for it. If you make it, hit me up. What you're still thinking, this is what's so crazy how old are you? 26. This is how fast the game moves.

15:2816 year old you listening to this would know you could build it. But because you're 26 you already are old enough to not think that I could build the app. No I know that I could build it. My focus isn't there. We're tunnel vision and what we want to do. But what you would learn if you're 50 is like I'm going to actually do it because I need to know it well enough because this is a skill that's going to be so important that if I always outsource it I'll never really know it so I'll never be able to judge it over the next 10 years. Did you see what I just said? Learning it is huge. But did you see what I said?

15:58Yeah, I get it. Because now you're gonna have 50 kids that are gonna DM you and be like, I can build it. You don't actually know enough to make the best decision. One of the things that's made me very dangerous is because I do the things, I can judge the kids. Right. So you start to realize it's worth your 100 hours even though you're busy as fuck. If it's worth my 100 hours, it's definitely worth your 100 hours and you start to prioritize the trenches. Right, okay. Makes sense? No, it makes sense. It makes sense. So how do you get rich reselling? You say lean into AI. Yeah, I think that's clearly one.

16:30I mean, like diversification. My big theory, and you guys know this, you watch me do it publicly, that the sneaker kids were gonna crush with cards, more inventory, less weight. It worked. I was right. I think there's more categories. Like if, and by the way, passions. Like I'll give you one. Getting into music. Physical music. Cassettes, DVDs, CDs. Like you see what's going on with, you know, So, you know, Ski's doing some stuff. I think Aoki did some stuff. Bit of everything. Like, I just think everything is gonna... That's essentially exactly what our expansion is. Like, we've talked... Correct.

17:01Started with just sneakers and now expanding into all these things because all these worlds now, and this is something we were gonna ask you later on, actually, they're all intersecting now more than ever. 100%. This was my theory. The person that is into sneakers... Yes, this was my theory. ...now enjoys trading cards. You guys see the video? This was my theory. So, I guess I would ask you then. You know, we've talked more extensively behind the scenes about the Gottsoul expansion. I'd love to hear, like, your candid thoughts on where Gottsoul's going, expansion to a culture festival? It's all gonna come down to execution.

17:24What do I think? I think everyone should do everything. That's what I'm trying to do. Right. I like really have my hands in everything. Like things that people don't, people don't know that I have a very successful hot TV production company. You guys don't even know that. I don't talk about VaynerWatt at all. Right. We're about to sell three major shows. Like there's gonna be a massive show on ABC and it's gonna be VaynerWatt. And you're gonna be like, you're gonna hit Tyler and be like, is that Gary? Like VaynerWatt? Like, so I'm in TV. Like now with AI music, I'm like, I'm gonna have the number one rap album in the world.

17:53What do I think? I think that your bravado and confidence and prior receipts give you a chance of pulling off what I think you're trying to pull off, which is like, why wouldn't you be the most important, you know, event covering all the genres of interest? Why wouldn't you? Right. Yeah, I mean, I think it's a no-brainer for us. I think God's Hall's positioned the brand in a unique way and already had all these other worlds prior that have come under our roof. So, yeah, it's almost a no-brainer, like you said. Yeah, like why wouldn't you add vintage clothing? Yeah, we have it. Correct. Why wouldn't you?

18:25Why wouldn't you add stamps and coins? Like you will when you eventually think it's worth your operational. I think everyone should achieve to as much TAM as possible. The addressable market, right? TAM. I'm obsessed with TAM. Like when I make things, like VFriends. I built VFriends not just to get like eight-year-olds that collect Pokemon. I'm also making gummies. I want to be General Mills, like Flintstone Vitamins, and Count Chocula fucking series. I always talk about VFriends. Three to 93. I want kids watching cartoons on YouTube kids and I want to fucking make adult fucking pampers. Depends with fucking a character on it.

19:09I don't give a fuck. Why wouldn't I want to sell to nine billion people? I think that's another piece of advice for the resellers though. Even for a lot of people who watch us, if you're just selling sneakers right now or you're just selling trading cards or you're just selling vintage clothes, like you should be exposed into all these worlds. And I would say if you do it based on passion, then you'll really crush. So there's people flipping sneakers, but they love music way more. They should spend 50 hours understanding what's happening with vintage music materials. DVDs, CDs, excuse me, CDs, cassettes, records.

19:40Like if you love music, like love it. Like you're hardcore and like you had an older sister that was into like Grateful Dead and Fish things, but you're a hip hop person. and your girl's fucking, you know, Hispanic and she's into rig a ton. It's your life. You love it. Like, why don't you spend 50 hours understanding how to flip music? Posters and tickets and memorabilia. Like, you like it more than sneakers. That's, by the way, the reason I knew sports cards was gonna work is the overlap of kids that were flipping sneakers that liked sports was high. The overlap of kids flipping sneakers that were gambling on sports apps was high.

20:16I knew sports cards was the mapping. Is sports cards a bubble? No. It's been around way longer than sneakers. True. It's been collected for 100 years. Do you think that there's any chance? No. Dude, I think the market could be frothy. A bubble to me is like something that bursts and dies. Right. Can it be frothy? Sure. So could the stock market. So could gold. So could Bitcoin. Art. Everything. I mean, sneakers were. Right. But they weren't. Like when sneakers were at their apex before the card movement, it wasn't that it was a bubble. it was that people didn't anticipate trading cards coming in and taking some of the market.

20:52Thus, once you take the market, if the demand goes elsewhere, all of a sudden, right? It changes. Can something come along and take away from the sports card market? Yes. I think comic books are under leveraged. I think toys are under leveraged. So that might, it might all grow, which is my theory. Just collectibles. Like, LeBuboos, vintage clothes, handbags. Like, the girls are in now. The girls are in now. More than ever. More than ever and gonna continue to grow. The 40 to 60 year old dude who grew up with it heavy in the 80s and 90s with me, more than ever. To this day, I'm getting pinged by very wealthy people saying I'm finally ready to, I just sold a piece of property to create liquidity.

21:35I've got 800 ,000. I'm going into collectibles. I collected cards and comics. Is there anything else I should be looking at, Gary? These are just friends, acquaintances. Right. Like we haven't even started. No, I agree. I mean, you're seeing people like Kevin O 'Leary who's spending all this money and people are putting together asset pools now. Of course. And investment funds. Of course. It's funny because you talked about that, what people call is a bubble of the sneaker market. And I agree that if something doesn't pop completely, it's not a bubble, right? It just has the - Corrections. But right, so I guess I would ask you now, going back to a hot topic, the number one narrative now that we see on social media in the world to the sneaker world, their sneakers are dead.

22:10That's crazy. In your opinion, are sneakers dead? Well, you know this because we actually had a regular business meeting the other day and I told you that I might be entering and buying some of the top stuff because my assumption, because I've not really been paying attention, my assumption is, well, it has to be a little softer than it was because all these new things have entered. I don't understand how people don't get, sneakers have been part of our pop culture forever. They haven't been collected forever. You know, sneakers looked more like trading cards. Trading cards really didn't get collected, collected, collected, collected as valuable until like the late 70s.

22:43by my subjective decision. People collected, some people got it, but you started seeing the late 70s, like shows, Beckett, like it started to happen and really popped in the mid 80s. Sneakers, they were unbranded, then we had the Converse and the Chucks and like nobody was buying Jordans on release being like, ooh, if Jordans ends up being really great all time, nobody was saving them, which is why they became valuable. But now it's a forever game. It will ebb and flow and I think it cycles. Like I, Don't like to predict, but I find it unlikely that sneakers aren't red hot, more so than cards or NFTs or comics or toys in some 20-year window.

23:25I don't know if it's three years from now. I don't know if it's seven years from now, but it's too culturally important. And it's on our feet. It's more functional. Like, I don't collect sneakers like that, but I buy sneakers to wear. So that's more functional than a trading card or a comic. You get to double play with sneakers. you get the collectability and you get the flex sitting courtside going out on a date you know your boys you know how it works like when I walk in the airport I'm looking at people's feet so that they got a proper like both me and some other guy was wearing the Ben and Jerry's Nike thing one day and we just fucking you know dapped it up like it's like a sports jersey correct it absolutely is so I know that it's not the red hot collectible right now in youth male culture the way it was five seven whatever the apex was it's definitely not dead and in fact if you're a long-term collector, investor, flipper like I am, you want to buy on down cycles.

24:18I think now's the best time. I mean, you literally heard it from me in real life off the record in our last meeting. I've never meaningfully collected sneakers. I'm like, oh, I should go and get three to five all-time pairs because I'm sure this is softer right now because of all the attention to the other asset classes. A thousand percent. Educate me. Give me an all-time top 10 sneaker that was red, red, red hot, let's say right before things started to move how much it was and how much you can get it for now. Give me one example. I would know right off the top of my head. A 1985 obviously the Jordan 1.

24:51The Chicago. Yeah the red and black. Chicago Jordan 1. The one that was banned. Yep. That's the bread. Okay got it. So the Chicago is the white and red one. Got it. Respect. Understood. Respect. Either way the 1985 model either the bread or the Chicago. No give the Chicago. Give it the real one. The Chicago would go anywhere from anywhere from 20 to 40 ,000 brand new. Which is obviously rare and all that. Yeah, of course. In the heyday. Yeah, in the heyday. In the peak of sneakers. Right now, you can get a pair for probably, if you can find it, $10 ,000 to$15 ,000. Yeah, it's awesome. I mean, if I heard that right, somebody on earth did pay$37 ,000 for a pair how many years ago?

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25:29That was five years ago. Not even. Yeah, not even. Right? And now that same pair could be had for$17 ,000? For example, at our last event, a pair was for sale brand new, in the box, 1985, for$15 ,000. Great. So to me, again, when I go and do my journey, because I haven't, and that will be tough for me because I hate Michael Jordan, so I may not buy that. But to me, that gets me excited because I'm like, okay, it got to 37. It's 15. That means it definitely, 37 has been established. There's gonna be inflation. I'm gonna catch it at a different time. Oh, that's a$55 ,000 sneaker. On the next red hot cycle, inflation, time, things change.

26:07Oh, that's good ARP. That's how I think about it. Oh, I think I can make 40K in a 10-year window. The problem is most people listening aren't playing with a big enough bank to make big investments and go to sleep. Everyone's flipping. Respect. But you flip your way up to be able to go buy some things to invest in. Right. That's how I think about it. Speaking of kind of analytics behind all this, right? Another thing when people talk about, oh, the sneaker game is dead, this is what's happened. Do you think that StockX is responsible for the sneaker game having the hit that it did? Absolutely not.

26:38A lot of people say yes because it made it a all about the money and less about the love. What do you think about that? I don't believe that's the case. I agree. I mean, Josh has been on the pod. Josh Louvre. It's not even about Josh or StockX. It's just about people blame things for things they've done. Right. Like, let's go back. For the love, with all due respect to the white heat moment of five or six years ago, the percentage of people that were in there for the love is now being romanticized. Right. The reason it's changed is not StockX, it's that those same people who didn't love it went to another thing because they're just chasing the arbitrage of math, of money.

27:15So that's actually the next question. It's like, in general, and I think this isn't even just for sneakers, this is for trading cards, collectibles, everything, right? Do you think that people who collect, collect for the love or do they just collect for the money? I think people that are collectors collect for the collecting. I just think they're a small percentage in every market. Right. Is that wrong to collect or be a part of this just for the money, you think? This isn't the Soviet Union. how is there a wrong? I don't think so either. Of course not because you're maturing. Right. And maybe you never did.

27:45No. I don't know. But I can tell you like how can I impose, this goes back to politics. Like if you grew up in a heavily Democrat or Republican family. Right. And like, and your family values were built around an ideology. Who am I to tell you that you see the world wrong? Now there's wrong and right and I think we can all agree on some things go a little too far. But the concept of convincing people to see the world exactly the way you see it is laughable. And so that's how I see collecting and flipping. Collectors that shit on people that are flipping and say they ruin it, I understand why. If you're a collector and you just want to own something, it sucks when it's red hot with flippers because now it's 40K instead of 4K.

28:31Right? But that's called capitalism. That's called the world. I agree, and I think going to your point you were saying a bit earlier. On the flip side, real quick, if I may. Like flippers who like get caught with the bag because everybody left to go flip something else, they were part of that whole ecosystem. They can't shit on the game they were exposing. Right. If you get caught with the bag, that's on you. I agree. And I mean, you knew that there was a risk. We talked about risk earlier. And I think one thing that you were saying earlier is a lot of people who are collectors, they say, oh, it's so expensive now.

29:02I hate the resellers. But now that everything's lower, they're not buying the things that they say they want. Well, this shit's expensive. Like, I don't blame someone not spending$15 ,000 on a pair. But yeah, yes, I think the most, like, if we want to get to the punchline, yes, I believe most people on Earth are bitches. Okay. But that's okay because, like, you know, like, I'm surrounded by friends and family that are complainers. Right. I get it. People are going to complain no matter what. That's right. Like, I just don't think about that shit. Right. Joe, I want you to ask the Nike thing because we're talking about complaining.

29:36If you go down a little bit. Oh, yeah. I like the format you guys are doing this. We're hitting a lot of stuff. This is fun. Go ahead. I don't mean to cut you off. I just want to get to it. I like what you're doing. Notice what I just said. And we mentioned, obviously, the whole Nike thing, right? Okay. And sneakers, and so obviously Nike being the leader in the sneaker world. I want to ask you, obviously Nike, you've probably seen online and throughout stocks. The stock price shows. Yeah, Nike is down right now. I don't need to look at, by the way, I'm not paying attention to the conversation.

30:04I actually have no idea of the stock price. I just know because I look at people's feet. Right. I mean, fucking five years ago, every single person had a fucking Nike Panda on, like, I just look at people's feet. Right. Like, the dominance of Nike six years ago, and it was dominance, has now been completely decentralized. With the running shoes, with the Reebok, with New Balance, like, it's just, it's incredibly obvious. But anyway. I'm gonna ask you about that specifically in a second. Go ahead. But my question is gonna be, obviously you just said everything about Nike. What would you do in today's world right now, what would you do as the CEO of Nike to bring the stock price back up?

30:43That's a great question. I think Nike got caught in a lot of different ways. I think Nike's positioning was always two things. Sports performance and then they had culture with Air Jordans and Air Force Ones. When they had the heat of the heat with Air Force Ones and culture, they stopped supporting the retailers. They started wanting to go direct. They wanted to keep and so they hurt a lot of relationships. Then they also got out innovated. Some of the running companies cloud all that like they started making shoes that people liked better. I think Nike needs a full reset. I'd probably do an M &A deal.

31:21If I was actually the CEO I'd probably want to go out and buy something. You know to give us a jolt. Buy what? I'm still not paying attention to apparel. I would go what would I buy? I actually want to answer this. I would buy If Gary Vee was the CEO of Nike Panini You'd buy Panini. You'd get in sports cars. Maybe. Well they don't have sports cars. They don't have the licenses. Oh right anymore. Like Panini's an interesting one because I could probably get it for a lot less than it was worth. I could get into another category. Maybe Funko. I would So you wouldn't buy in footwear. Like you wouldn't buy an on cloud or you wouldn't buy something like that.

31:57I wouldn't buy there because that's my core competency. as Nike they have enough money allocated to R &D I might fire my head of R &D and hire the head of R &D from Enclap right? But I would because I would have more and I don't know everything about Nike but I would have more confidence in my ability to innovate the next sneaker than I would creating net new categories for us. Okay. I would invest if I here is the problem if I was actually the CEO of Nike I wouldn't have enough time to do what I would want to do because I'd get fired first meaning I would invest in blockchain. Wow. You know, I would diversify the company to win in other areas.

32:35Again, I would have confidence that we could make better sneakers. I would probably hire somebody from Chanel or like whatever is the hottest fucking, you know, apparel business right now, the best creative director. I'd probably hire them, you know, to like bring in that culture a little bit into our, like we're in such a bad place with Air Force One. You know, I think they own Converse. Yeah, they do. I would probably try to use Converse to combat Reebok and New Balance and let them play like a challenger brand mindset. Okay. So you could see kind of where I'm starting to map out my plan. Okay, interesting.

33:14So you didn't even talk at all about Nike's footwear specifically because I think one thing I want to get your opinion on, and this is another hot topic, is Nike's brought back, like Joey talked about the Chicago one, they did a lost and found version of that, but they brought back a lot of these, you know, really grails. So like an undefeated Jordan 4. It was a really friends and family shoe. And Joey. It went from being a$40 ,000 shoe because it was so limited when it first came out years and years ago to now you can buy a pair on Sock X for$250. Because it wasn't released. So my question is this.

33:43Right, so what they did wrong there was they thought, because that's out there, let us get the short-term economics of everybody who wants to buy it. But what they killed was the secondary market which actually is driving a lot of their primary and so they thought short. I don't think Nike understands that either. that that secondary market is put drive the primary. Like Nike, there it is. You know, you're like, notice how weird I went. I went to Converse to act like challenger. Right. I believe that our R &D department definitely can compete with any other fucking company but let's get our shit together.

34:12Right. I went to the left field shit like another collectibles ecosystem because we have the money because we're a big company. Right. Yeah, I think they're too narrow. They want to extract the value out of the secondary market which actually hurt them in the long term. Yeah, I agree. So the punchline to that. So Nike bringing back all these crazy sneakers that were super exclusive. I would have never done that. That was the question. That's a really bad idea. I couldn't agree more. That's a really bad idea. Now, what they should have done was they should have bought up all the originals in the secondary and then created ways for people to get them through supporting their short-term business.

34:46Whoa. Got it? That is interesting. Right? So what if every new Nike, so they launch a new Kevin Durant and they tie it into legacy and they say in the Kevin Durant, they come up with a new seal on boxes so it's more like a trading card and there's golden tickets following legal sweepstakes laws and every one of us knew that we could get an actual$50 ,000 pair because we bought the KD. This is the Gary V effect. Well yeah, this is like, you have to think in those ways. Wow. And that would only work for a little while too but it's definitely smarter than it sounds like what they did. I agree. People say bring it back for, let people have access to it.

35:24I disagree. No, because what built Nike's great window five to seven years ago was the secondary market. Right, okay. When you're a company that tries to eat up all the oxygen of all the economics, they fucked, and if that's what they did, which it sounds like, did they do that with a lot of things? Yes. Okay, let me tell you what they then did, because I don't like talking when I'm not educated. I wasn't aware, now I'm a little bit aware. What they did wrong in this five-year window was they destroyed two markets. They destroyed their retail market. Third-party retailers weren't getting the allocation of the hardest stuff.

35:54they were controlling it and they killed the secondary market that was creating heat for their overall new stuff and now they're left with neither. They have to rebuild that trust with both the retailers and with the collector community. Okay. We don't have a ton of time and we love you for these long answers. I need like 15 second answers. I'm allowed to follow your lead. Go. All right. Faces of the sneaker world, we had Michael Jordan obviously retired, Virgil rest in peace, Kobe rest in peace, Kanye. Kanye, yep. All these people who are faces of the sneaker world who got it to this point are no longer the face of the sneaker world.

36:28Who's the next face of the sneaker world? No idea. Does the sneaker world need a face to grow up? It doesn't hurt. Okay. Doesn't hurt. Okay. Could Adidas overtake Nike? Everybody can overtake everybody. That's the coolest part of business. You know, it depends on what time frame and things of nature, but everyone can take over everybody. Okay. Is Supreme making a comeback? could it be ever what it was? 100 ,000%. Supreme represents one of the biggest theses I have. That once hot, always in play to be hot again. Got it. Could it be bigger than it ever was? Harder. Harder. Harder to be, you know how big it was.

37:09You guys probably were, yeah. Harder, but look what Crocs did. Crocs took over the world in a different way in the 90s. Way bigger. And had a really good run. I think it's starting to slow down a little bit, but like three years ago, you saw that you guys got to see that I mean no cool kid would wear a pair of Crocs for a decade right now no cool kid really wants to wear Supreme it'll be away for long enough and somebody's gonna reboot it okay my question to that is now my follow up to that is Supreme obviously it's come back what's your thoughts on Chrome Hearts come back right now I'm not educated enough okay I just don't know I don't like answering things I'm not educated about Chrome Hearts enough to really know 100 % okay by the way that's maybe the most important, everybody who's watching, like, that might have been the most important part of the whole interview.

37:57Like, I am very convicted with my takes and things of that nature but so many people are trying to build personal brands right now and talk about shit they don't know. The I don't know is so powerful. I hope that what I just did, where everyone was like, whoa, Gary V's not on, no, I'm not, like, I'm just still a human. I don't know everything. I know a lot because I watch pop culture enough, but But more of you should say I don't know, or I'm not sure, or I'm just starting to figure out. It will really benefit you. Got it, okay. Anyway, sorry about that. We saw Logan Paul's Pokemon card. Yes. It sold for over 16 million.

38:32What's the next collectible asset that could sell for that high of a figure or more? I'm very bullish comics. I haven't started buying, so I hate to put it out publicly because I'd like to get some, but I think comics are sitting in a really good spot. Also, the mix of comics and cards, something I have been buying that I'm obsessed with is vintage fictional character trading cards. 1940 Superman's highest graded rookie card could get crazy. It's in the hundreds of thousands. I think it'd be 20 million. I'm very bullish on that. I think cards and comics are really sitting pretty. I do think video games, toys, music, physical collectibles all have a shot and I do think clothes, including sneakers, all have like, all of these things are in play.

39:13They're all in play. Next one. So traditional assets like real estate and stocks or non-traditional newer assets like trading cards, sneakers, what are you investing your money into more today? Me personally? Yeah. The latter. Okay. Do you think that new age collectibles are a better investment than real estate, stocks, and traditional investments today? I actually think old collectibles are a better investment than, new age collectibles are dangerous. Okay, so collectibles in general, are collectibles a better investment than traditional investments like stocks and real estate? Yes or no? In a macro?

39:43Today. It's even. Let me explain what I'm gonna explain. In a macro, it's even. Stocks and real estate have the equal opportunity to be remarkable as collectibles. First, the fact that collectibles is even in this conversation is bonkers to everyone. Second, it's been proven over the last five years that there's a lot of exciting things that have happened in collectibles, but don't get it twisted. Like, people have made real money in playing Miami properly. People have made real money in playing NVIDIA. like you could have bought a fucking Michael Jordan rookie card or Charizard NVIDIA worked we make the mistake of saying everything in the macro here's the third part I get much more joy out of owning a collectible that goes from I bought it for 50k and it goes to 2 million than I do from owning 50 ,000 in a stock that goes to 2 million it's more of a gotcha essentially yeah it's just for me personally it's more enjoyable it's not more of a flex for every person but for me it's more enjoyable and that's why the fact that that was even a conversation is wild.

40:47But you can lose a fuckload of money in all three and you can make a lot of money in all three and know your shit. If you really know real estate and you don't know collectibles or if you know stocks, focus on what you know. Everyone watching right now that thinks oh you're cutting them off or we're going quick? We only have limited time. Yes, he's doing the right thing and I cut off everybody when I podcast so I'm good with this. Got it. Is celebrity dead when it comes to influencing collectibles? I don't know if it's dead, but I'm glad that it's more thoughtful. Okay. I don't think people blindly will, like I even feel comfortable starting to, I stop talking about specific things.

41:22Even the fact that I just brought up vintage fictional characters, Spider-Man, Thor. I wouldn't have done that for three, four years because I was scared that people would speculate on my words. Right. I'm starting to be a little more comfortable talking about things I believe in and like because I know people won't blindly follow me. Okay. That's good. Right, right. Okay. what's the one thing that the collectible culture is missing right now?

41:47Time. It's just a matter of time. Okay. It's gonna get so much bigger. I agree. So we're seeing that female thing I just referenced it. We're seeing some of those $800 ,000 OG guys and girls going in for the first time. We're seeing people be smarter and not just buy something because I tweeted it or Aoki or Logan Paul. Like everything's getting better. We're just getting started. Yeah, it's just time for it to mature and get cleaner, get rid of all the riffraff, have it more professional. Got it, okay. Keep going, keep going. I'll figure out what, like two minutes. Go, go, go, go. I'm in charge always.

42:22He's just keeping me educated. Okay, got it. We're getting pretty much to wrap up now. If you were Gottsoul's head advisor, what's the one piece of advice you would give us? Hire faster and fire faster and promote fastest. Okay. You've got a lot of ambition. I know you a little bit now. I think you got it. You need more people. People is what is gonna make you more successful. You have to hire them to even know who are your boys or girls. Like, right? If you don't hire someone, you don't know if they're good or not. Right. Right? You also, once you hire, you have to be able to make better decisions on if they're good or bad.

43:00Quickly. Quickly. You know, you gotta give people a chance. If you're like, oh, Jeremy sucks. It's not like, oh, Gary told me to fire. No, no. Hey, Jeremy, I think you might suck. let me tell you why I believe that you're fucking really I can see what you're doing you're really just hitting on the girls on the floor like whatever it is right like you're trying to steal our clients and do your own thing which is fine but you can't do that on my dime like you're just a pro okay hire fast fire faster that's the number of people and promote fastest if on the flip side you hire Jeremy and he's fucking 15 hours a day when he doesn't have to fucking you know yeah like we yeah like people make that mistake they try to keep people down yeah they're like oh I'll say oh this guy's awesome oh I got a whole year before I have to give him a promo or a raise.

43:42No, no. You show a fucking winner that you see them quickly you can change the calculus. They're there with you for four years instead of a year and a half. Got it. Right? So they've been seen. Last two things. And by the way all of that comes out of just how much money you take home. Right? Like the key is the reason I keep telling everyone to do what I'm saying is too many people want too much from their business early on. Both companies that I built up were massive. Wine Library and Vayner, I made literally$40 ,000,$50 ,000,$60 ,000 a year into my 30s. Yeah, okay, got it. We want to give you your flowers.

44:19I want to say this, I mean this from the bottom of my heart, like someone who's looked up to you for a decade, right, and I remember we drove from Babson in a snowstorm just for you to sign those sneakers. You signed like 20 pairs for us and we gave a bunch away with our nonprofit and me and my friends got stuck in a snowstorm and missed class the next day coming to see you. And I had never been so nervous meeting anybody in my life. And why I was nervous, not because there was this person on the camera that I was going to meet and, oh, okay, this is this big moment for the business. It's because, is this guy going to be who I expect him to be?

44:49And you've been that. We've talked off camera multiple times. We've had meetings, all these things. You've been that times a hundred. And I just want to give you your flowers to say that, you know, listen, we've had the pleasure to build something that means something to have these meetings. the vast majority aren't going to get to that point. What you give the world with no ask, with just give, is going to pay exponentially. You know it because you even say it is selfish in the long term because it's going to pay back to you 100 times. Of course. Karma is practical. The value that you've given to people like ourselves, off camera, on camera, is paying dividends to generations that you won't even see.

45:24And I just want to give you a thank you from myself, from Joey, from our team, from our family, the thousands of entrepreneurs who will never get to say thank you. I just want to say thank you for everything you give and that comes to my last question. You have literally millions of fans. People do this S tier, A tier. A lot of people now even say you're like the goat content entrepreneur, goat social entrepreneur, you name it. For all those millions of fans that are out there that love you, that have watched you for years, what's your one message for all the fans back at home? That's your camera right there.

45:54Don't even look at me, tell them. What's your one message? That nothing you do professionally actually matters. Which is bonkers, right? if you just listen to that setup, the part of that setup that meant the most to me is people knowing I'm a nice human being and that I've helped matter so much more to me than the zeros in my bank account. I know the cliche response, easy for you to say now that you have it. I got it because that's who I was. And like the people that really have known me the whole time know, you must live your life. Like you have to hear me on this. Notice even in this interview, I said if you love music more but you make more money in cards and comics, go all in and learning music because flipping music's gonna make you happier in your soul.

46:35What makes me happy in my soul was these flowers. There's no money I make that ever makes me feel better than the moment I just had. People knowing I'm a good guy and me knowing that then it affects them so that they'll be a good guy to the girl or guy that comes and sees them in 15 years that I'm setting the framework that I am literally one of the few people on the internet that's like, no, nice guys win, nice guys win, nice guys win, be nice. Like, I know. I mean, somebody left a comment to a post I did yesterday that got like a thousand likes on TikTok that said this is the king of toxic positivity.

47:12And I laughed. I laughed that we live in a world where people really believe there's something called toxic positivity. I'm not delusional. Does anybody listen to what I say? Toxic positivity is slang for delusion. I'm selling you all delusion that life can be good or that it's nice out there or it's not as bad as you think. That is insanity to me. It's the truth. But you've all believed the naysayers. You've believed the cynics, the politicians, the scared parents and teachers and bosses. You're allowed. But I'm telling you right now, fuck fear. Fuck fear and go get yours. And if you actually believe you can't because someone told you it's tough for your generation.

47:54Gen Z's fucked by the boomers and you'll never be as successful or sneakers are dead and you're fucked because you got a closet and a warehouse. If you believe you're dead, do you fucking understand you're dead?

48:09I'm not saying this is the secret. All of this is hard work. I've got two admins and a whole team behind me looking over my shoulder right now because I'm four minutes late. That's how valuable my time is. It's all fucking work. But I promise you, if you don't choose practical optimism, meaning you have to be optimistic that you can, because it's true, you can. You might have to go through therapy. You might have to cut all your fucking toxic friends out. You might have to stop popping pills and smoking weed. You might have to do a lot of shit, but you can. I know you can. I've been on the receiving end of thousands of you who weren't you, who were fucking already set up for winning and it just had to be a little truth of love.

48:47I didn't let you down and you kept listening. I've met thousands of not you. Fucking real drug use, abusing their girl, really fucked up, hating the world. only like trying to build out of fear and hate not out of love and optimism and I've watched my content and my interactions and many others that do what I do convert these people to straight gangsters and that's what I want for you. I don't want you to have a shit fucking life. That's my rant. I do not want you to have a shit fucking life and I promise you it's this. And that's that. Gary, we love you. We are so excited to do more with you.

49:22Can't wait. Thank you. Thanks everyone. 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.

From the publisher

In this episode of the GaryVee Audio Experience, I sit down with the team at the We Got Sole Podcast to discuss the evolving world of reselling and culture. I explain why I believe reselling is a better business education than college and why the current "soft" sneaker market is actually a massive investment opportunity. I also dive into the importance of your reputation as a moat and why being a "nice guy" is a long-term business strategy.

 

You’ll learn about:

  • My "hire fast, fire faster" management philosophy
  • Why I’m bullish on vintage comic books and fictional character cards
  • How to use AI tools to scale your business solo

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