Sam and Shaan interview Gary Vaynerchuk about his deep dive into NFTs, covering his VFriends project, the long-term utility of smart contracts in real estate and ticketing, and why he thinks 98% of current NFT projects will go to zero. Gary also walks through how he managed cash flow while scaling VaynerMedia from 6 to 1,200 employees, explains the lesson he took from missing the Uber investment, and shares how his investing philosophy has shifted entirely to betting on the person over the idea.
Speakers: Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road), Gary Vaynerchuk (guest, CEO of VaynerX)
Post-Episode Wrap — Hosts React to Gary Vee [00:00:00]
Sam: That was intense. 45 minutes, dude. Sometimes you have high hopes for a guest and on this podcast I’ve been disappointed. Today was not that day, my friend. I loved that. I had a great time. Honestly, we didn’t even get to — we got to like 20% of the stuff I wanted to ask him about.
Sam: So we had Gary Vaynerchuk on the pod today. It was phenomenal. Whenever I leave — I’ve hung out with Gary maybe three times — whenever I leave his presence I do feel better. And a lot of people, and I’ll admit I was one of those people years ago, would be like, “Oh, this guy’s just some loud guy who’s selling nonsense.” He’s totally the real deal. And I went to — we talked about it — but I went to a dinner with him one time and he talked the entire time. Most people would be like, “Dude, what the hell, that was so rude.” And when I left I was like, I just want to continue listening to him. I want him to continue telling stories. I love his point of view. He’s entertaining.
Sam: That guy is intense. I love it. He does what we try to do — he’s been doing it for a long time — which is business entertainment. It’s the entertainment side of business where he’ll go to a garage sale, make content about buying things for a quarter and flipping them for $28 on eBay, and show you how that stacks up, how you can go from $42 to $14,000 in a year if you just did this. Obviously he doesn’t need to do that anymore — he’s got this agency with hundreds of employees, he’s got a bunch of stuff going on — but I like that he’s been able to do what I think the world needs more of. Business entertainment. Because why did I grow up wanting to be a basketball player? Because the NBA was so goddamn entertaining. When you have entertainment, it creates inspiration and aspiration. It ends up creating more founders in the world.
Shaan: Yeah, he was amazing, man. Whenever I’m with him off the air, by the way, he’s exactly the same. There’s no show here.
Sam: So we started off — we got right into it in the first 30 seconds. I asked him about something I had been tracking for a long time. When I was managing my business, I was trying to manage cash flow, trying to understand how hard to push it, and I made a document on Gary Vaynerchuk about VaynerMedia — they grew to 1,200 employees. I tracked revenue per head over hundreds of interviews, basically found where he said in a clip, “Oh, we have this many employees.” So I asked him how he managed cash flow. Then we got into a really interesting discussion about NFTs.
Sam: A lot of people talk about NFTs. I’m not like an NFT guy. Shaan, you are. This was the one time I’ve ever had a conversation where it interested me beyond just academic.
Shaan: Yeah, he does a good job making it tangible. He doesn’t make the big mistake, which is: “NFTs — let me tell you what it stands for and how it works under the hood.” It’s like, no, I don’t care how the engine works. I want to get in the car and go somewhere. And I think he did a pretty good job of that.
Sam: So we talked about NFTs, and we talked about the lessons he learned going from the dot-com boom — he was early in the game around 2000 — and then he was there for Twitter, Facebook, Uber. He got into Twitter but he missed Uber even though Travis was one of his best friends. So how did he take those learnings and apply them now? Good episode. He was super nice, wants to come back on. I think we should have him on again.
Shaan: You know, it’s when people say, “I’m always late to work because when I’m driving listening to MFM I gotta pull over and write things down — I can’t let this idea go.” That’s when we do it well. And I think we did it well on this one.
Sam: All right, that’s the episode. Gary Vee — enjoy.
Gary Vee Joins — Camera Setup, iPhone vs. DSLR [00:05:20]
Shaan: It’s nice to see you guys. I hope you’re well. It’s called Camo — I’ll give them a shout out. It’s called Camo. I think I paid $49 for it. It’s awesome, man. Hope everyone’s well.
Sam: We have a lot to get into. I’m pumped you’re here. Can I — and we’re recording now — something I’ve always wondered about: how many people work at VaynerMedia?
Gary: Somewhere between 1,050 and 1,300. Sorry — VaynerX. So VaynerMedia is the biggest company under VaynerX.
Managing Cash Flow While Scaling VaynerMedia [00:06:00]
Sam: I did some research based off a ton of interviews. I was going through the headcount of how fast you grew, and I believe between around years three and four, did you grow from like 30 people to 125 people?
Gary: Yes. In September of 2011 I kind of made the decision to go full-time Vayner — no longer what I would call full-time Wine Library. I made that switch and then the lighter fluid kind of went on.
Sam: How the hell do you manage cash flow for a company like that? I did research and I guesstimated off some interviews — around year one it’s like five people, then 20, then 30, then 125, then 300, 550, 600, 800. Is that a ballpark?
Gary: Yeah, like if I was spitballing — the first year was like we started in May of 2009, so that first half-year I think it was like six or seven, then maybe like 20 through all of 2010, and then until September 2011 it probably got to like 30. Then that’s when it went.
Gary: Look, what you’ll appreciate — there are certain people who are really, really good at top-line revenue-driving initiatives. What I think has been the balance of my life — and it’s very similar to what happened at Wine Library — is because I’m able to create so much top-line revenue, and because I’m playing forever, right? Wine Library was my dad’s family business. VaynerX for me is a forever business. I’m just able to hire a lot. And then you gotta calibrate. With retail it was really easy — I knew how to sell wine. With B2B it took me a little while to calibrate, like, “Oh, they didn’t pay us? Wait a minute, why didn’t you pay?” But overall it’s just staying in your business. I think when you stay in your business and you know what’s coming in and what’s going out — I’m not a CFO-oriented CEO, but I’m also not a schlemiel. I always have a good sense of like, “Are we gonna be dead? Will this hurt me? Will I be in trouble?” I try to stay within those confines. That’s it.
Sam: It’s just crazy. Did you have a line of credit from the bank?
Gary: No, we didn’t. And this is where my dad’s a psycho. I was so undereducated because I was such a poor student. My dad ran his business with no line of credit, which I love — old-school immigrant, pay with what you have. But it trained me, because that business went from $4 million to $25 million in like 30 months. Insane inventory and payroll. But I got so trained in playing within myself.
Gary: We definitely got a line of credit probably 2011, maybe 2013. But the first four or five years, in the pocket you’re talking about — which will resonate a lot more with people who are going to go through the 7 to 17 to 77 to 277 — it was more about just not spending what you don’t have. Very basic. Hey, we just landed this account, they’re paying us $480K a year — it’s Mondelez or Pepsi. You feel like they’re gonna pay you, you feel good. Okay, now I’ve got $480K. I’m gonna hire these six people at $40K a piece. It was very back-of-napkin.
Gary: What’s funny about it — and you know this — is mine can be like intuitive and back-of-napkin, and yet people who are all about learning, Excel sheets, doing it proper, SAP, cloud software — they get wrecked. It’s because they don’t have a good pulse of their actual business. They get ahead of themselves and lack patience.
Sam: It seems like you’re playing it maybe month by month, quarter by quarter. I would go to bed at night wondering: I hope this client doesn’t bail, otherwise I gotta lay off 20 people.
Gary: I think what was happening was we were selling so fast — and I think I had the answer — when you are selling at a level that people are not accustomed to, when you’re outpacing normality, just selling hides everything. When I’m landing a client week after week, you start getting into a place where you’re just outpacing vulnerability.
Shaan: Do you want to give an update on — I mean, I jumped right into that because I’ve always had that question. Sam’s been sitting on that for two years or something. He didn’t say hello, didn’t say what the podcast is about. He’s like, “Hey, when you scaled, how did you manage cash flow?”
Gary: I’ve gotten to know Sam through my podcast and a couple hangouts. It makes sense to me because I think Sam’s really good at what he does, and he lived that life, and he knows what the anxiety and the challenges are. I always say you can only — my favorite people to talk to are the people who know, because they’ve lived it, not because they read it. Same way I feel when I talk about sports — I love sports, but I fully know when I’m talking to an athlete, I don’t know what they know.
Shaan’s Viral Clubhouse Thread and Blab [00:13:00]
Shaan: I did this thread that went viral on Twitter. It was about Clubhouse — when Clubhouse was sort of peaking. I said it was unpopular, not my intention to be negative, but I said, “Everybody thinks Clubhouse is the next big thing and I think it’s going to fail, but here’s how I think it’s going to go.” I kind of wrote it like an episode of Silicon Valley — you’re the CEO, Chris Sacca is texting you, this is happening — and it went viral, ended up on CNBC, like tens of millions of impressions. And people were like, “Oh man, you’re a good writer.” And I was like, I’m not a good writer. I built this thing called Blab that was very similar to Clubhouse and I went through this exact run. I was just literally telling a story I knew of myself and exaggerating a little to make it funny. It has nothing to do with writing.
Gary: You know what’s so crazy about that — it’s kind of how I think about why I’m a good content producer. I literally stay in my lane. I may say the same thing 8,700 different ways, and that’s a little bit of my talent. I’m good at incorporating contemporary pop culture and the slang and nuances of the day. But the reason I think it works for me is similar to you — I have so much conviction because I’m not guessing. I’m not out here guessing.
Trash Talk Video and Listening to the Audience [00:15:30]
Sam: I was watching your Trash Talk video on the way here. I was driving, listening to it, and I was like, “God, this is good content. I bet this video hits.” And of course the views were pretty high.
Gary: By far my best show. It’s my best content. And do you know why I made it? Because I listen to my audience. I read my comments. What was super awesome — I started getting a lot of emails from people saying, “Yo, you’re awesome, I love you, but this whole ‘you put a $25,000 check into Twitter’ thing — that doesn’t work for me. I don’t have $25,000.” So I was like, cool, let me go even further back in my origin story. What did I do when I was digging? I went garage sailing on Saturdays and sold that stuff at baseball card shows or other flea markets on Sundays.
Gary: I just sold $3,500 worth of old computers and I got more joy having that $3,500 in my Venmo than I did with $20 million in my face.
Sam: This brother is everything that I believe. I believe the reason I like this stuff is I’m in it for the game.
Gary: In my last episode, I found a bunch of manga — for $270 I bought what ends up being about $6,400 in eBay post-fees sales. It’s crazy. It’s the thrill of the hunt. But the part I was blown away by was — I watched you go to 20 garage sales in a day, and I was thinking two things. Like, this channel, this show, is basically the most approachable version of entrepreneurship.
Sam: We do these segments on the show that people love — one’s called “Billion of the Week,” where we profile a billionaire, but sometimes we’ll do the “Hillbilly of the Week,” which is someone who owns 22 vending machines and we break down how much money they make.
Gary: That’s so smart. Another one we do is called the Blue Collar Side Hustle — here’s something you don’t need to be a genius for. Because sometimes I go off on my crypto stuff and I’ll be like, “Oh yeah, this is the future.” But then sometimes it’s like, “Hey, you know what you should do? Go door-to-door doing pest control leads.”
Sam: I love that.
Gary: That’s so smart. That’s what I’m living right now. I looked at my calendar today and I saw I had this podcast — and obviously you guys have done a great job and I’m fired up about it — but literally in the back of my brain I’m like, “Man, I hope they got cut short or something, because if I get back that 45 minutes I can go more on OpenSea and do a little more research.” I’m so enthralled right now in NFT life that every meeting I’m cutting five minutes short. But meanwhile, the only other thing that’s got me juiced is garage sale education, because I know it can help people and I love it. It’s the same game.
American Pickers and the T-Shirt Business Model [00:19:30]
Sam: Do you know American Pickers?
Gary: I know that show, yes.
Sam: I used to work on that show. I used to work for Mike Wolfe, the main guy. The way it worked is he would go from barn to barn — not garage sales, barns — and buy stuff. We’d buy some cheap stuff we could sell in the store for $50, then we’d buy some old motorcycle that doesn’t work but we could sell for $20 grand. All these people would come in from all over the country to the store, and we would probably sell $5,000 worth of items but we would sell probably $30K a day of t-shirts. That business crushed it.
Introducing NFTs — Shaan’s Kobe NFT Story [00:21:00]
Sam: Shaan, you want to talk about some NFT stuff? Because that excites both of you. It excites me too. Are you trying to get into it, Sam?
Sam: No, I’m into it. Shaan told me what it was like a year ago and he bought some really cool Kobe stuff, and I went and got something and thought it was badass. But Shaan’s really into it. He’s got a ticker behind him.
Shaan: Yeah, I have this programmed where it can tell me the price of Ethereum or whatever altcoin. In this case I met the founder of Nifty Gateway, and dude, first — this story is hilarious, I don’t know if you’ve met them — it’s two twins that built Nifty Gateway. They got bought by Gemini, which is amazing.
Shaan: So this was pretty early in the wave of NFTs getting hotter and hotter. What they did that was smart — they said, “Look, NFTs have value because they’re scarce, but the problem is anyone can mint an NFT tomorrow.” Which is fun, but there’s also an abundance of scarce objects. It’s a fascinating supply and demand game. What Nifty started doing was being like Christie’s — they curate. They find the best artists on Instagram, bring them on. These artists had been building a following for 10 years doing free art for the love of the game on Instagram, and now there’s a way to monetize that audience and that art.
Shaan: So I bought this Kobe — the Forever Mamba. I was telling Sam on the pod, “I just bought this thing for $800.” He goes through the cycle everybody goes through: “You bought a file? Why are you buying JPEGs? You spent $800 on this?” And I was like, “Yeah, actually I bought five.” He’s like, “You bought five copies of the same thing?” Those sell for $10 to $25K now.
Shaan: So that was my first flip — my version of the digital garage sale. That’s why I’m so addicted. Give us your simplified version of the thesis. Some people are in the weeds, some people eye-roll. The truth is there’s something really exciting going on and there’s also a bunch of stuff that’s going to go away. Give us your take.
Gary’s NFT Thesis: 98% Go to Zero, But the Utility Is Massive [00:24:30]
Gary: I think 98% of the current projects go to zero. To me, this is most similar to internet stocks in ‘99–2000. I remember being there. I was young, I didn’t have as many pattern recognitions and reps, but I had a lot of the good ingredients. I remember sitting there and saying, “Man, a lot of these businesses make no sense.” When March and April 2000 came and most things got smoked out, it was a monumental moment for me. The only stock I bought was Amazon, because I really thought it was a real business. It had actual revenue. The others didn’t have revenue. No customer gave a damn. And I’m always asking: does the customer care?
Gary: So what do I think overall? I think people are grossly underestimating NFTs. Right now people think of them as collectibles, art, and flip games. For a lot of us — the American Pickers, garage sale, sports cards people — that’s a big industry over the next 15 years. Big. Collecting, flipping. You’ve got an entire generation of kids who go on Fortnite and Madden and 2K and buy digital assets to flex. That’s going to play out. But I think that’s just a nuance of NFTs.
Gary: I think people misunderstand the utility nature of smart contracts. I believe in the next 15 years that nobody writes a book with a publisher — they do it through an NFT infrastructure. I believe in 15 years nobody launches a record by having a record label give them the bag — they’re going to get it from crowdfunding by selling NFTs and giving a percentage of royalties. I believe there’s not a single sporting event or concert in 10 years where the ticket is not an NFT, because there’s no incentive for that organization to launch it as anything but an NFT. A QR code or a piece of paper means nothing. But if Luka Doncic drops 100 points in that game, that ticket stub becomes a forever collectible. There’s a trillion dollars’ worth of ticket stubs that have sold over the last 25 years on eBay — all of that goes to royalties to the person who issued the ticket.
Gary: Here’s a weird one. If you own a home that is wildly unique — a $25 million home on a beach — you NFT that home right now. Put into the smart contract that you get 1% of every transaction of this home in perpetuity. The first person that buys it from you is gonna be fine with that. These things are long holds. You buy it, you sit on it for 13, 15 years. There’s so much that NFT blockchain realities are going to bring that I think people are underestimating.
Buying Michael Jordan’s House as an NFT [00:27:30]
Shaan: You want me to tell them the idea?
Sam: Yeah.
Shaan: A few months ago we were shooting the breeze before an episode. We don’t tell each other what we’re going to talk about — it’s like, “I’m bringing three pieces of heat, you’re going to react to it.” One of the ideas I brought on was that I noticed Michael Jordan’s house had been sitting on the market in Chicago. It’s got the 23 emblem on the gate, a basketball court inside — it’s been sitting there for years and the price has been dropping. I think it started at something like $20 million, went down to $14–15 million. So I came on the pod and I was like, “Dude, I think we could buy Michael Jordan’s house for $10 million.” And I was like, normally someone would do this by writing a $10 million check, or raising a fund in back-alley conversations at dinners with rich folks. Or — we could just use this podcast, crowdfund $10 million, and do fractions, either through an NFT or on Rally Road. Let’s buy Michael Jordan’s house.
Gary: That’s exactly what should happen. I don’t love that many ideas. I really bet when I love something and it’s worked for me. But when I tell you I love the idea of buying Michael Jordan’s house — I know you can arbitrage it in perpetuity. You’re people who can garner attention and promote, so it’s worth so much more to you than to someone else. I could see the entire entrepreneurial ecosystem renting out the basketball court. You can run a real business.
Gary: Now back to my big point about unique property — I think this is going to change the real estate industry. You’re young guys. You put a 2% royalty in perpetuity on that home. You sell it to the next person for $9 million, let alone $12 million. You and your great-great-great-grandchildren are getting an $80,000 check in the mail. I do think in the next five years there will be an “aha” moment for what NFT blockchain smart contracts mean for real estate. People will buy unique properties and make incredible in-perpetuity money.
Gary: Listen — if you’re listening to this right now, you are either there or you are aspiring to be there from a professional standpoint. We’re sitting in this weird moment because of crypto and NFT where there’s some people who’ve come into real money from making a very smart play. If you’re sitting with some money, these are the things you’re thinking about: what can I do that’s fun for me but also leaves generational wealth? The house is perfect, because it’ll be fun for you 16 or 20 weeks a year, but you’re also creating something that’s an asset in perpetuity.
The ABA Team from St. Louis: In-Perpetuity Money in Real Life [00:32:00]
Gary: There’s the ABA team from St. Louis. You know that story?
Sam: Yeah, yeah.
Gary: They merged the leagues and the St. Louis team was out. They fought and fought because they really loved basketball. At the end they said, “Okay, well if that’s the case, we have to be treated financially as the 22nd or 24th NBA franchise — and in perpetuity we get the economic split for that.” So they’re out of the league but economically they get it. The league — I think two brothers — made hundreds of millions. And I think the grandkids got bought out by the NBA before the last big TV deal. Unbelievable.
The Wallet as a New Social Identity [00:33:30]
Shaan: You were talking about NFTs — I think another use case that I like when talking about it with you versus with super-geniuses who are like biology PhDs: our audience is a guy who owns his own marketing agency in St. Louis. He’s like, “Okay, what does this mean for me? I don’t want the how. I want the what.” And to me, when I talk about NFTs, I think about the fashion industry. I think about why somebody owns a Rolex. I think about social media. Like — how about this: you know how everyone’s like, “Social media is full of fakery, everyone takes photos and fakes it”? You know what’s going to be a much better social identity? What tokens do you have in your wallet publicly.
Gary: Dude, I was thinking about this yesterday. My public wallet is going to represent me because it’s not only going to be my crypto punks, my VFriends collection — it’s also going to be all my Jets tickets. If this was going on for 30 years, every day on Twitter I’d probably get, “Gary, you went to Dave Matthews New Year’s ‘99 at Madison Square Garden.” I’m like, “Yeah, my friend Tokyo Joe, I love that night.” It’s a truth indicator.
Gary: And one last point — this is what really confuses people. Every one of you has an aunt, uncle, niece, nephew, friend, or grandma. When you go into their house, they collect marbles, or little miniature elephants, or magnets from every state they visit. Humans are inherently hoarding assets. We use them because we like them, we get caught up in the nostalgia and the story, and we use them to flex. Flexing a painting or your Winnie the Pooh collection is kind of hard except for the people who come through your house. The blockchain is going to accelerate that at scale the way I thought the internet would accelerate communication with social. That’s why I think people are underestimating it.
Gary: The first internet collected information. The second internet created the framework for communication. This third thing — web3, NFTs — it’s going to capture the consumerization of assets. And the stakes are high.
VFriends: Locking in True Fans, Building an IP Universe [00:36:30]
Sam: With VFriends — you offer a conference ticket for a year. Are you going to do that forever, or is there a timeline?
Gary: So, this is pretty interesting. For the hardest-core consumers of my content, VFriends made so much sense. The amount of times I’ve referenced Walt Disney and Vince McMahon — character creation. I’m building VaynerX to buy nostalgic IP, refurbish storytelling — Saturday morning cartoons, wrestling, Thundercats, Transformers. I wanted to buy Animal Crackers from Mondelez and turn it into Madagascar. I’ve been in this place forever.
Gary: Two years ago I was going to launch a toy line called Workplace Warriors — literal desk toys, with basically what became these characters. So for me I see NFTs — I’ve been kind of flirting, and I had my crazy eureka moment, my “no, no, this is it” moment. I bought ETH a long time ago. Aaron Battalion — shout out, former CTO of LivingSocial — got me in in 2015–16. I’ve been watching. But I wait for the consumer moment — the normal person, the marketing agency in St. Louis — not the hardcore infrastructure nerd. That’s just not my jam.
Gary: So the answer is it’s a three-year contract. VFriends Series 1 says you get a conference ticket to VCon 2022, 2023, 2024. I’ll figure it out after. But I knew that would have such inherent value that people would lock in. What I was trying to do — the word I’d use is “trick” — my hardest-core advocates into holding by giving them an asset. If I pull off what I think I can pull off — stuffed animals, toys, trading cards, movies, video games over the next 40 years — this original NFT has real potential. And I wanted to create a thing that wouldn’t make my biggest earliest supporters trade it.
Gary: Look at Bored Ape, look at Meebits — epic projects that are killing right now — people are trading. I wanted people to be locked in so that by the time the three years are over they’re like, “Wait a minute, I’m never selling this.” And the data backs this up. If you go on CryptoSlam — cryptoslam.io — VFriends is like number 12 over the last 30 days. About $12 million of transaction volume. The funny thing is, if you go through all the other projects — CryptoPunks, Meebits — they have somewhere between thousands and tens of thousands of buyers doing these numbers. VFriends has like 300 people with 580 transactions. What that tells me is there is a small group of hardcore people who are not looking to flip this for a quick buck, because they believe in me and in the utility value of the conference.
Gary: I like that. It’s different. I’ve been very aggressive with it — I’m like, “Do not bet against me. I’m going to build Transformers.” A lot of people are holding now. The conference is going to be epic and I’m going to come through. They’re betting on my propaganda right now, and I’m going to come through.
Gary: It’s like Bitcoin early days. The people who bought in were anarchist crypto nerds. You need the first people to buy in for one reason, then the speculators come, and then once everybody’s got the thing we can all just use it as a medium of exchange. Similarly, what’s interesting about NFTs right now is just functionality. VCon makes it functional — they’re about to get very functional — and the functionality is going to be extraordinary.
Shaan: I told my guy before this pod, “I’m going to talk to Gary today — let’s pick up a VFriend.” He’s like, “Cool, the floor price is $17 grand now.” I was like, oh, okay. That’s not what I expected. But it kind of opened my eyes.
Wallet as Profile — Privacy, Myspace, and the Coming Mass Adoption [00:41:30]
Gary: I want to bring back the wallet-as-profile point. The only reason I’m in that world is the right one — and YouTube is going the other way, where you can filter your face and do many things to get non-verifiable content. It’s interesting — the argument of controlling our own narrative versus the black-and-white public data of what we buy.
Gary: Now, for everyone who loves privacy — you don’t have to share your wallet. But I was there for Myspace in 2004 when everyone was saying, “People are going to get kidnapped at the mall.” And I was like, “Nah, I think it’s going to go this way.” And now it is. I think that’s what’s going to happen with NFTs. You’ve got the hardcore people I get on Zoom with, with voice distorters and screen scenes — I don’t know who they are. The masses are coming, and they’re in the public wallet, the Rainbow wallet, the .eth world. I think that’s where it’s going.
Why Hasn’t Gary Bought a Brand Yet? [00:43:30]
Sam: You’ve been talking about buying brands and putting them through VaynerMedia for like years three or four of the company. You’ve been saying that whole spiel for a long time. First of all, you haven’t done it yet. When are you going to do it? And second, I think putting them through the NFT thing is significantly better than the old model you were probably planning on — running them through the VaynerMedia machine.
Gary: You’ve got it. I would much rather buy an old ’90s brand and do this. I mean, I’m looking at who the biggest brands are on CryptoSlam — it’s sports companies. I think you can do brands even better. When are you finally going to execute and pull the trigger? You’ve been talking about it for a long time.
Gary: Well, it’s like — dude, why do you still need employees? You built that machine. It’s badass. Do the other thing now.
Sam: Yeah, you’ll appreciate it. I think that’s an incredibly strong observation from the outside. I just know how close I am to actually being a Death Star versus a really badass machine. I feel that like truly. I’m like, I got a better machine than the other 500 people I admire who think they have this down. But it’s so close to being two or four times better. And the way I’ve scratched my itch was Resy, the restaurant app — I had a major exit with that. Empathy Wines. And now VFriends. VFriends is really with me, because I’m like — by the way, I had Animal Crackers bought four years ago. Signed and they pulled out late. They had a clause in the contract that allowed them to. I had the master plan: it’s a cookie brand, I was going to make it healthier to be on trend, but what I was really going to do was turn it into an animated film. Build up Larry the Lion. It was kind of VFriends before VFriends.
Gary: Ultimately I think I’m young enough at 45 — have the leverage, have the infrastructure — that I’m going to do a whole bunch of everything. I can build a studio like Pixar with VFriends at the forefront, and I can buy Champion when it gets cold again and refurbish it in 13 years. I’m going to try both.
Sam: How much could you have bought Animal Crackers for?
Gary: I think the deal was at the time — I hate making up numbers, I genuinely don’t remember — I remember it was like nothing. They were like, just done. They didn’t give a damn. And we were going to use it as a proxy to teach them how to do it with their other brands. It was set up well.
Sam: You did it with Nilla Wafers from a marketing standpoint and crushed it.
Gary: And I really scratched my itch with K-Swiss. K-Swiss was finished — dead, done. We exploded it. Not only did we sell a load of GaryVee sneakers, the residual effect on the brand was very real. That’s the closest I’ve come to really testing my machine. The only difference was it was a fake test because I was so involved and was the face. My plan is not to be that. The best part of VFriends for me is that GaryVee has been the catalyst for all the stuff I’m passionate about — work ethic, patience. I’m so pumped that over the next three years I’m going to be able to go a little more in the backdrop and let these characters take over as I build that IP.
Building a Personal Brand — Is It a Treadmill? [00:48:00]
Sam: That’s the biggest thing that pisses off my bougie friends. Like, “Gary, what the are you doing?” And I’m like, “What are you doing?” You go play golf and go on a yacht. I’m in a garage sale. I’m not telling you what to do.
Sam: Even besides that — I know we’re new to the game, we’ve been doing this podcast for about 18 months. There are a lot of benefits to building up a personal brand. Boom: I want to raise a fund, I raise a fund. I launch a course, it sells out. You can make a lot of money when you build a personal brand. You build trust with an audience by giving, giving, giving — like you always say — and then you sort of have your leverage later. So the part I thought was interesting is: you’ve been on this treadmill of creating content. You’re in your car, in your Uber, you’ve got a camera guy with you, you’ve gotta put out a sound bite for Instagram Reels because that’s the hot thing now. Are you still enjoying it, or do you feel like you’re on a treadmill?
Gary: The answer is I only do what I like. As a matter of fact, I’m not hitting all my team’s content quotas right now these last two weeks because I can’t stop being on CryptoSlam and OpenSea and Discord. You’d be stunned how much I could shut it down or triple down. I understand the benefits and the leverage, and I always did. I always thought the community and brand was very underestimated in the last 10 years. I just feel like people are just getting around to, “Oh, this is the actual game.”
Gary: But I enjoy it. I really do. And I also did it a little differently — I did it by myself for seven years, but then I built out an infrastructure of a team. Like, I’m just living and everyone’s recording and then we’re post-producing at scale.
Sam: How many folks are on the team right now?
Gary: I think there’s 22.
Sam: And you’re the majority owner of VaynerX, so you’re able to use the same resources across all your stuff. You don’t have to worry about pleasing a board. You don’t have to worry about fiduciary duties to anyone but yourself.
Gary: Exactly. I’m in heavy control. It’s a long-term play. No board, not publicly traded. It’s very much just a very large family business. And what’s cool about that is I don’t have to justify to anyone but me and my brother. And more importantly, I’m delivering. You know what’s super awesome — when you’re putting the wins on the board, nobody even gives — nobody wants to touch it. Then keep going. Nobody wants to talk to me.
Sam: Did you pay yourself from the company, or do you take all your side wins and reinvest them back into the agency?
Gary: Originally I paid myself very, very, very little. I’ve started paying myself probably over the last four years, but I’m still wildly undercompensated compared to what — if the god of merit came down — they would say I should be, because it’s all cycling in the same game.
Lessons from Missing Uber: Bet on the Jockey [00:51:30]
Sam: You look back at web2, you’re excited about web3 — can you tell the story of missing Uber? What did you learn from the web2 wave that you’re better prepared for now?
Gary: I love you for that question, because the only thing I’ve been thinking about for the last nine months is, “Damn, this is the first time I felt like this since ‘06.” The thing I learned was that I was going to meet a lot of people who were technically stronger than me, who would teach me new things. Young thinkers on fire. The world is recalibrating. And I knew that I understood the consumer and the human being well enough that I would figure out my path within it.
Gary: The uber story — Travis is the only person I thank in “Crush It,” my first book, besides my family. We were incredibly close. I had passed twice. The full story: when I was asked to invest, Garrett and Travis were the inventors and Ryan Graves was the CEO who was going to run it. I had just failed in putting up a wine social network called Corked, and it was a distraction from my core. So I was affected by thinking — if this is their side hustle, it’s not really them. Reasonable, by the way. You’ll be right nine out of ten times.
Gary: The second one hurts. Travis came back to me. There’s this grassy knoll somewhere in San Francisco — I have no idea where it is, like a little park — I drove by it seven years ago and got the worst feelings. I’m like, “I have to go back here once a year for humbleness.”
Gary: I’ll tell you this — I really hope it helps a lot of people. I have completely gone the other way. I am now completely infatuated with investing only based on the person. I have to “hate” — that would be the word I’d use, and I don’t love that word — I would have to hate the person’s idea to not go, if I think the jockey is a gangster. There’s a company called MeMac where I just saw Rachel, had one meeting with her, and I said, “She’s one of us. That’s it. She’s one of us.” She’s pivoted four times but the company is a monster now. Between the Uber thing and the Rachel thing, that’s kind of how I’m navigating web3 right now. I’m really trying to pay attention to: is this person one of us? Because there’s something about a human’s ability to will their way to success even if they have to completely change the business model halfway through.
Wrapping Up — Gary Wants to Come Back [00:54:30]
Shaan: Well, you were supposed to bounce three minutes ago. We don’t want to go over your time. It looks like you’re in the Hamptons — and it sounds like someone is setting up infrastructure for the weekend.
Gary: Listen, it’s super fun for me to see this show pop from afar. It’s a very funny time in society where work ethic and the grind — I’m incredibly excited that we have a balanced conversation. The energy of entrepreneurship is just such an important variable, and I appreciate what you guys are doing in this space.
Gary: I’m not gonna — I’ll have to ask him if it’s cool if I blow up his spot a little bit. But me and Gary had dinner with eight or ten other people like two months ago, and I went back to this guy’s house about a month ago again for another dinner. We’re gonna have to tell the story about this guy’s house. It was like the craziest house I’ve ever been to.
Shaan: We’re gonna tell them, listen. I’d love to come back — whatever you guys feel is an appropriate time for recycling a guest, hit me up. I wish you nothing but good. And thank you for having me on.
Gary: I put my all in it. No days off. On the road. Let’s travel. Never looking back.