GaryVee is ‘petrified’ of Slack

If you’ve spent more than two minutes somewhere on social media, you have come across Gary Vaynerchuk. 

And for years, I have wondered, is this just a character? Or is there a real Gary Vaynerchuk somewhere behind “GaryVee,” the social media entrepreneur and internet brand?

Vaynerchuk got his start working at his family’s liquor store, which he turned into an online wine shop. That’s where he started in social media, hosting a long-running YouTube show called “Wine Library TV.”

He parlayed that into the gigantic GaryVee brand, which, at its core, is about entrepreneurship. Gary himself co-founded the restaurant reservation platform Resy, which he sold to American Express in 2019, and Empathy Wines, which he sold in 2020. 

But the Vaynerchuk empire remains vast, and it’s structured in complicated ways. There’s a holding company VaynerX, which contains the ad agency VaynerMedia. There’s another company called Gallery Media, which owns lifestyle websites. Then there’s VeeFriends — Gary’s NFT and intellectual property business. VeeFriends NFTs came with tickets to VeeCon, Vaynerchuk’s business conference that just happened in May. Gary even co-founded a sports agency — VaynerSports, with pro athletes like the NFL’s Kirk Cousins and Sauce Gardner on the roster, as well as MLB shortstop Bo Bichette and a variety of combat athletes.

How does Gary manage all of this? He’s responsible for so many things — how does he make decisions? Is it all just a character? Or is that the real Gary Vaynerchuk? 

We got to talk about all this with Gary at his office in Hudson Yards in Manhattan, and he did not hold back. It was a ride, and I did my best to hang on. 

You can watch the video of our conversation in this post or on YouTube. There’s a cool graphic of Vaynerchuk’s org chart in there.

Okay, Gary Vaynerchuk, GaryVee. Here we go.

This transcript has been lightly edited for clarity.

Gary Vaynerchuk, also known as GaryVee, head of VaynerX, the advertising holding agency, and YouTuber. You have a lot of things. Welcome to Decoder.

Thanks for having me.

Decoder is a show about structure, process, and decision-making, and you have the most to tell us about that. Let’s start at the very beginning. How are your companies structured? How does that work?

VaynerX, which you just mentioned, a lot of people don’t know about. They see the GaryVee of it all, but they don’t realize that there’s a 1,500-1,600-person global company. In VaynerX, the main company is VaynerMedia, the company I started in 2009 with my brother AJ. That’s the advertising agency, the Mad Men, Madison Avenue thing. And then the next biggest companies in VaynerX are the Gallery Media Group, which houses purewow.com and One37pm, so that’s publishing.

There’s Vayner3, which is an innovation strategy company. AI, blockchain, VR, QR. That’s more like a Bain or McKinsey consulting company. Avery Akkineni runs that — that’s going well. VaynerSpeakers is a speaking bureau — Zach Nadler runs that. 

Then there’s VeeFriends. I’ve always wanted to buy intellectual property. I used to think I was going to buy the Flintstones or Gumby or the Smurfs. The NFT thing came, and I’m like, “Wait a minute — this is the place to launch it.” I launched VeeFriends a couple of years ago, so that’s my intellectual property business grounded in blockchain but also expanded to the real world. VeeCon, my big conference that’s coming up, is part of that.

And then there’s a little tiny room these days, though it’s been a big chapter of the last decade, of the GaryVee of it all, my content. I’m really not public speaking anymore. I am writing a new book, but it’s taking me a little while with how busy I am and all the content creation and the podcast. So yeah, I’m busy. 

You mentioned VaynerX, 1,600 people, that’s the big holding company.

That’s got the ad agency, a bunch of other stuff. Then you mentioned some companies that are not part of it. How do you make the decision on what’s in VaynerX and what’s out?

All the people listening that have two or more children know that you’re only as happy as your most unhappy child. Especially for the people watching who have five or six children, the reality is you’re ebbing and flowing. When you’re a captain of a boat, you don’t know where the holes are going to be. So the reality is I do view VeeFriends and VaynerX as the two cores, but there are moments when AJ needs me on VaynerSports. There’s going to be moments, as Eric Wattenberg builds out our production company, where I’m going to have to fly to LA and pitch a show for a big opportunity on Netflix. It’s going to happen. I decide based on two chiefs of staff and three admins, whose full-time job is to take all the inbound that comes in my texts and my Slack and my email and strategize.

We spend a lot of time during the week thinking about the three weeks ahead. We’re always having lots of 15-minute meetings instead of 30, trying to make a lot happen. It’s almost like being in the news business, — you have your editorial strategy, but then poof. In the sports media business, you have your strategy for the day, and then Aaron Rodgers gets traded to the Jets officially, and that’s going to change things up. And that’s what it is to be an operator at a high level with multiple things going on. I have my strategy for this week, but anything can happen in the next hour that blows out three hours, and then those three hours have to get back in the books because those are the top 5 percent of things in a world of a million things being thrown at you. It’s a constant flow.

How much do you delegate? 

An enormous amount.

You said you had what, five people? Are they actually in your Slack? Your admins have full Slack access to your DMs?

Scarier than that. My admins have access to everything. My iCloud, my email. I live a transparent life with my admins. They’re signed into all my socials. I keep it very transparent with them because I need to be able to navigate quickly, and they need all the data points. So I delegate tremendously. I would argue that for a lot of people listening or watching, all of their limitations on the growth of the things they’re operating — by the way, whether that’s a family that you’re operating and not delegating enough to the oldest child or to a friend or an aunt or a grandparent, or if you’re running a business or, like me, many, many, many businesses —  delegation, trust, the lack of ego of thinking you do everything the best is an incredible thing that I most look at when I’m trying to help a friend, family member, or an investment to figure out why they’re not scaling.

When you think about delegation, there are your admins, then you’ve got companies, and you’ve got people running your companies. How do you decide, “These are the people who are going to be in charge of this company inside of VaynerX, and this company needs to be outside of VaynerX with a different leadership structure”?

Outside of VaynerX has been easy. Stephen Ross, owner of the Dolphins, is a business partner of ours and couldn’t own a piece of this sports agency, so we spun that out. VaynerSports and VaynerWATT are the only things outside of the company. With VaynerWATT, because Eric needed to be such a significant partner, it needed to sit out of the structure. But most things will go into VaynerX if they’re in that service world. And the way I decide that is pretty simple. I either really know, or I really don’t know. 

Let me explain. Avery, who runs Vayner3, or Jeanny Ponce, who runs VaynerToronto, were executives that were here three, four, five years and doing great work that made me confident to send Avery to Asia Pacific, or Jeanny up to Toronto.

Then there’s guessing. I made a subjective guess on Gabby Fenton, who runs Latin America in Mexico City. I made a subjective guess on Daisy Domenghini, who’d been in for a couple of months, to take over AMEA [Asia, Middle East, Africa], UK, Europe. And then in those scenarios, you go in optimistic, you go in focused on trying to help them, and then in a 12, 18, 24, 36-month window, you’re making a final decision if you made the right call.

Are you telling them, “Here are the metrics I’m judging you on — make the number go up”?

Not really. Yes, they can’t go out of business, but I’m not a publicly held company. I’m not looking to exit. So I’d like them to be fiscally responsible. They can’t be completely aloof. But I would argue that what I most focus on is: if you do not have the people that work for you, and I mean all of them, not your direct reports, incredibly happy with you, feeling safe. I think when you have a people-based business, if you don’t understand how disproportionate culture is, I think you’ll lose. I really do. And what I mean by losing is, there’s unbelievable amounts of businesses out there that are winning financially that don’t have good cultures. It’s not good. It’s toxic. It’s anxious. It doesn’t even need to be toxic or that serious — it’s just not great. It’s like a job, whatever.

For me, those companies are missing out on top-line revenue and profit. I’m telling all of them, “Get everyone feeling safe,” because there’s so much fear in the world, and “Get everyone understanding how unique the marketing strategies we have are,” or in VeeFriends, “what we’re actually up to, or whatever company it is.”  VaynerSports, “how well we are in marketing off the field.”

Get the core messages down and understand them, but most importantly, build a safe, happy, accountable, but happy place. I call it “honey empire.” Honey over vinegar, but we’re trying to build an empire. This is not for fun. Those are the metrics, and that is a struggle for people on the outside. Everyone out here in big buildings is being trained to win on the P&L, not on the culture.

This is actually my next question.

You’ve got a big holding company. You’ve got lots of empowered executives.

We talk a lot on this show about divisional structures versus functional structures. A lot of tech companies are functional. Tim Cook runs marketing, and he runs product,. It all rolls up to him, and at the end of the day, they somehow produce an iPhone. Other companies are divisional. You’ve got just a stack, and you’ve got some redundant functions. How is VaynerX structured?

A little bit of a mix of the two. The reality is, I do a lot of casting on leaders. What’s interesting is we’re a 13-year-old company, VaynerMedia. VaynerX is even younger. That happened when I bought PureWow. We started building it six years ago. A lot of this has to do with HQ, the VaynerX of it all, has its leaders, but we keep that pretty thin, and we give a lot of power to the leaders of divisions and companies. But you are micromanaging and creating redundancy. It’s almost like a kid riding a bike. You’ve got to give them training wheels, especially if they’re from the outside.

When I bring in new leaders from the outside, I’m going to create some cushions, just because the reality is we do it very differently, both the craft and the culture. And so once someone is able to cross over the hill, then I think we can make it far more autonomy based. I like to be close to people that have enormous amounts of control, though I have no interest in micromanaging them. I’m in the business of Batphone. I’m in the business of making them feel safe.

Did you say Batphone?

So if there’s a crisis, you’ve got to call Gary? Do you have a special Batphone?

No. Everyone has the same number. But it’s funny. Yes [in a] crisis, [but] it’s more like, “Just keep me close. Use me.” Actually, ironically, we had a global offsite yesterday. So many of the leaders want to prove to me they can do it. And I keep telling them, “Hey, I know you can do it. The problem is, you’ve been doing it for 20 years on the outside. There’s 7,300 nuances here. Text me and ask. I’m not judging you. I’m here to help you. I work for you.” But outside executives struggle with that. They don’t believe me. And it sometimes takes three to five years for me to break through with, “I’m not kidding. You’re not going to get fired by missing your numbers, but you definitely become vulnerable if people aren’t happy.” And the quickest way for people to not be happy is for you to be scared of me and it, which then trickles down.

Do people use your name to get what they want? I feel like at a company that’s called VaynerX run by Gary Vaynerchuk—

You mean executives with each other?

“Gary wants this.” Does that happen a lot?

I’m sure that’s happening. The cool thing is, as a 13-year-old company, we have almost 100 people that have been here for nine years or longer. We have crazy retention. And I think what’s awesome about that, when I hear this… I would say six, seven years ago, probably a lot more than today, there’s too many people entrenched in too many places that know the truth of it all, that it’s almost like a double negative. There’s so many family members in so many different places that I think it’s harder to get away with that, but I’m sure that happens every day at scale.

Yeah, I’m always curious, especially when your name is on the door.

What’s cool is I have such an aggressive open door policy that, ironically, the junior people use me more than the senior people at times, and so a lot of people are comfortable, even a year in only meeting with me once but based on everything that they know, to email me and be like, “Hey, my boss’s boss’s boss said this. Is this true?” And I’m like, “No,” or, “Yes.” I couldn’t encourage leaders that are listening here more to find as many five- and 10-minute slots to say hello to a new employee. Just that breaking the ice of it all is massive.

This brings me to the Decoder question. You’re describing this process where you make big, long-term strategy, you have a vision, and then you’re very reactive to things that are happening to you and incoming information all day long. How do you make decisions?

I love how you put that. I literally operate on macro patience and micro speed. I make decisions based on a lot of things. One, my intuition. I really do believe [in] that. I think a lot about what we know today that people didn’t know 100 years ago. A ton. A ton about the body, the mind. I always ask myself, “What are people going to know 100 years from now that we don’t know today?” My favorite running thesis right now is that we don’t talk enough about the gut, the intuition, the operating system that this is. We know what this is, but we don’t talk enough about this, and so my big guess in 100 years is this is understood a lot more and is a normal part of life.

Intuition, you mean?

That’s right.

Not microbiome.

Both, by the way. Ironically. It’s funny I was about to say that, but that’s exactly right; both, actually. How much of an impact on your life this is. So intuition is very big. Pattern recognition is enormous. For the 23-year-olds, it’s harder. For everybody who’s 45 and older, massive. Experience matters. These gray hairs start to add up. They do have value, and so pattern recognition. Number three, a complete utter focus on intent and lack of fear. Every decision I make I know has good intent, truly, thus rendering me very confident that if there’s ramifications, or I made a misstep, that the apology is always there, that the correction is there, the vulnerability, the humility. I’m not scared of making a wrong call, and I think that’s a huge part of my decisions.

And then tons of data. The reason I want the Batphone, which is really more just so that we check in and keep talking, is that I can make fast decisions when I’m sitting on a lot of information, and so I’m talking to all my employees all the time, virtually, through text, or in person, mainly to make me have the ability to go fast in the future.

One of my biggest beliefs is that most CEOs don’t spend enough time judging the judgers. I am judging my 40, 50 most senior people on how much I value their word, blindly, like Marcus and Hannah, my chiefs of staff, who I’m looking at across the window right now, because they’ve been here for nine and 13 years, or less, but a road to it, for an executive that’s maybe running a company or an office that’s only been here for two or three years. I can’t be blind with them yet. I don’t have enough data, but that’s the framework I work in.

I’m just talking to you here in person. You’re very animated, you’re very charming, you’re very direct. I have discovered that when I’m very direct in digital communication, I come off like a huge jerk. How do you do all the things you do and communicate digitally with your team?

I don’t communicate digitally.

You don’t? You’re not Slacking?

I do, but I’m petrified of it. I tell everyone, “If it’s something real, get out of text.” The misinterpretation of the written word digitally is a monster. People will consume it based on their framework. When I do [send a Slack] and I have to give any level of direct [feedback], I’m coming with a heart emoji and a sun right behind it. I do that a lot because I’m petrified that someone’s losing the tone. Cole just joined our team, just joined our WhatsApp, where my team works. He doesn’t know me, and if I’ve got something to say right now, he might think on his first day, “Wait a minute. Gary’s actually full of shit. He’s not nice.” I need to put that heart emoji, I think people need the voice memo so they can hear my voice. I’m petrified to deliver even neutral to slightly candorous feedback in just written word. I think it’s a massive mistake. I have completely gotten my leadership team off of the long email. It’s crazy. You’re scaring people.

By the way, ironically, GaryVee in interviews, my content, is great at candor. Gary Vaynerchuk, the executive, has struggled historically with candor. I hate negativity. I’ve always seen candor as something that would scare people. I had it misunderstood for the majority of my career, so I call it “kind candor.” If you’re delivering candor, you need to be empathetic that the other person on the other side is not going to feel great. Even if it’s truly fair, they’re still going to feel bad about themselves, so why not have compassion and try to make them feel a little bit better by referencing something you’ve struggled with or just fixing the tone? I think about that a lot.

I always think about it like you can tell people it’s okay to feel bad, and then you can work through it together, but that first step is really hard.

Or you could really put it on yourself as a leader and try to make them feel less bad. There’s absolutely a way to make someone feel slightly less bad when you’re telling them that they’re not good at their job.

Let me talk about GaryVee with you. You brought up this other character, GaryVee, versus Gary Vaynerchuk, the executive. The business of GaryVee seems as complicated, as chaotic as anything, and it exists on social platforms, which are ever-changing. We were talking to your team just before you sat down about just how much video of you is logged every single day and what an enormous operation that is. Is GaryVee a character you’re playing?

No, no. It’s me fully. It’s just the context of the room is different. Right now, I know that we have a longform video and audio execution, and I do believe that being slightly entertained or engaged — and this was something I did subconsciously when I first started speaking — I have intuitive understanding that you’re more likely to get your message across if people actually pay attention.

Fair enough.

So no, there’s nothing that I’ve ever put out on the internet that is shtick or fake. It’s just that the context is different. If I’m having a company offsite that’s trying to navigate a $350 million a year business, you can imagine with 15 people that’s going to be a very different tone and tenor than me doing a podcast, which is one of my favorite media platforms out there. I’m just going to be more excited. I know that somebody’s running on the treadmill right now, walking their dog, driving in their car, and I want them to continue to hear the words, and if it’s super serious and mundane, that might not be the energy you’re looking for. I’m also aware that my energy might be too much for someone. This is too hyper, and that’s okay. This is just what naturally happens to me when there’s cameras going, and so no, it’s not character life; it’s just a slightly more animated version of myself, given that I get more excited when I think there’s more people involved.

But when you have this many people following you around with cameras, logging everything you say, ingesting it into what sounds like a very impressive Airtable system. I’m very jealous of it—

Thank you.

You’re a reality show, right? You’re kind of producing a daily reality show, and that naturally has to heighten whatever loudest characteristics you have.

I don’t know about that; I’ll explain. If you look, I would argue that YouTube is the platform that I do least well. Mainly because I’m not overly passionate from a reality TV show standpoint, meaning I’m not trying to rate. I don’t want the vlog to be overly successful from winning an Emmy or getting a lot of viewers — I’d be fine with it. I’m trying to document way more than I’m trying to entertain. A big part of the vlog was done because I lost both my grandfathers before I got to know them, and I thought it would be neat that one day in 67 years, this would exist. I also knew that it would bring awareness and demand, but I really wanted it as a blueprint for people to see this entrepreneur thing is not so fun. It’s not as easy or cool as it’s become. For example, there’s nothing that I do day to day that has anything to do with the vlog. It’s just a documenting framework.

I have to ask you, do you ever turn it off?

When you think about the image you put out into the universe… I watch your TikToks. I love your TikToks. You’re always talking to an audience.

It always seems like you’re addressing some room. That’s the majority of your content. Your audience does not see that you’re just walking on the treadmill, and you’re happy that it’s hot outside, that you’re quiet with your family. You have a very particular kind of image. Do you worry that you’re leading people to believe that you’re always on and that they should themselves always be on?

No, I don’t worry about that at all. For example, I think people find what they’re looking for. I’ve been very aggressive that I don’t want to share my personal life. I have tons of challenges. I speak about vulnerabilities. I’m a public figure. People know about my stuff. No, I really don’t.

I understand the question. I think that it’s time that we have a more thoughtful conversation around this, meaning I, as a human, when I consume content at scale, never believe that any of the people that I’m consuming are showing you every single thing of their life, nor do I believe it’s as good or as bad. I think that’s a very lazy intellectual point of view.

But don’t you have that point of view because you grew up with it? I mean, I grew up with the internet—

Well, I didn’t.

It grew up with you. It didn’t exist, and it slowly has gotten to where it is now, and you’ve seen that whole transition. I think about our young audience: they’re fish, and they don’t know about the water. They just grew up in a world where influencers exist, in a world where YouTubers exist, where being a YouTube star is a career path that you can tell your parents when you’re five years old. And so you have this view where this isn’t all real, and you’re making the reality show, all of us are making the reality show, and you have an audience that doesn’t know that it’s a show.

Well, I think the way you framed it up is a little awkward. Let me explain. I think everything I show is real, it’s just not the complete part of my life, and there’s certain things I decide not to share. I also think, when I think about this, when I was a kid, pre-internet, we looked up to stuff, too. My entire high school, all the girls were in the bathroom throwing up because they all wanted to be Kate Moss and weigh 80 pounds. My big question is, where is parenting in 2023? 

But you are that figure for a lot of people. Young men, in particular.

Yeah, but that is such an extraordinarily deep challenge. When I think of being someone that someone may look up to, I’m humbled by that, and so much of the way I create content understands that to be true. But I could never comprehend the complexity of actually being someone’s parent, or someone loses a parent and who replicates or fills that void. You look at that from a human journey, and there’s many inputs that fill that void. I think that’s right. I do think that there’s incredible intrigue that I have about the sheer volume of people that are putting out information in the world, but I feel like that has always been the game.

There’s an entire generation of boomers who lived their life like Mickey Mantle because he was the one that they looked up to, so it’s always existed. What I’m actually optimistic about is there’s way more ways to look at things today, and I think how people choose their paths is interesting.

You’re very good at using your experience to adapt to new platforms, in particular, from YouTube to Instagram to TikTok to NFTs, if that pans out. How do you think about that tension? “We’re doing well on YouTube, but I need to take everything I know and go find a new audience on TikTok.” Because this is something you talk about a lot: you have to jump when the time’s right.

You got to jump when the time’s right if that’s your ambition. One of the things I talk a lot about, back to people hearing what they want to hear, is you need to be self-aware over everything and understand the journey you’re on. So if you’re a business and you want to grow your business, you have to go where the consumer attention is.

That’s just a requirement. So the way I think about it is I am on my journey to try to build as much awareness as possible for the things that I’m passionate about. For me, I enjoy my craft, I enjoy my job, and I want to do that. On the flip side, I’m very empathetic and talk a lot to the audience. This happened three, four years ago. I’m like, “TikTok, TikTok, TikTok, TikTok, TikTok,” and everyone’s like, “Ugh, dude, I’m just getting Instagram down.” And I’m like, “Cool. You’re more than welcome to not do it. You have to understand the attention’s going to move there, and you need to understand where you are on your journey. You can’t be ideological about where you want the consumer attention to be. You need to be where the consumer attention is.”

With that constant change, that platform churn, I’m looking at the state of social media today, and there are a bunch of YouTubers worried about burnout culture, and they talk about it openly. I’m worried about a bunch of TikTokers who seem like they rose with a platform, got burned out, and they’ve receded. That first wave of really big TikTokers, they’ve kind of pulled back.

But that’s good, isn’t it?

It feels like being the most famous person on YouTube is no longer a great business. 

It was never a great business being the most famous person. Think about what we’re dealing with. You and I grew up in an era where we knew that, for child stars, it was tough. And so a lot of these kids get so much fame and money at such a young age; it’s really hard to calibrate that.

Are you coming at this from a marketing perspective when you talk about attention movement?

What I hear is a great marketer saying, “Okay, I need to go send a message, and we’ve got to move to the platform, be native to the platform.”

There is a generation of entrepreneurs who are like, “This is my business. My business is making content.” You know a bunch of them.

Of course.

And you go between those worlds, GaryVee is a brand that makes content as a business. I’m sure it’s monetized. If you’re the world’s best TikToker and you reach the peak, you’re not making as much money as you would if you turned around and launched a merch line and stopped making TikToks. That pattern makes it seem to me like we’re at the end of the road. Everyone’s realized the centralized social platforms are not stable foundations to build businesses.

Meaning if you’re just monetizing as an influencer?

If you’re monetizing as an influencer or even if it’s your core marketing platform.

That would be like saying running commercials on Seinfeld is not sustainable. No shit. Once it hasn’t got the attention, you have to move on. So as core marketing, I think it’s crazy to not extract awareness from where it’s actually being consumed.

Fair enough.

To your point on the human element, that’s a whole different game. That comes down to parenting and DNA, right? When I met the D’Amelios, I was like, “Oh, these girls are extremely fortunate. This is a real dad and mom.” It’s like my VaynerSports business. Do you know how many athletes grow up with nothing and then sign big contracts? And the ones that have self-awareness and stability do incredibly well with their money and their life, and the ones that don’t become quite vulnerable. To your point, when you’re a business, it’s easier to move ebb and flow. When you’re a human, there’s going to be a natural time where you can’t deal with the negative comments, the workload. But I knew that looking at the Madonnas and Michael Jacksons and all those people in the eighties — that we would see them ebb and flow.

It was funny, I was listening to a Bruno Mars song this morning, and it was just in rotation on my Alexa, and I was like, “Where is Bruno Mars?” And I was thinking, “Oh, he’s probably chilling right now and decompressing from world tours and all that fame.” We’ve seen that with every single famous person over the last 40 to 50 years. It’s impossible to stay white-hot forever because you’re a human, and you need to take a break. I did five years of a wine show every day from 2006 to 2011 and was really out and about. And then, from 2011–14, I made very little content, building the foundation of this business because this business was an opportunity and because I was like, “Eh, I don’t want to make wine content every day.”

My daily vlog, I did it every day for three, four years, filmed everything. The team will tell you right now with their head nods. We’ve been getting back into it. I don’t want to film half the stuff because I’m out of rotation, and I think every human should be comfortable when they want to go for it, when they don’t. They’re going to be hot at certain times. They’re not going to be hot. And what I mean by that is, they themselves are going to be into it at times, they’re not going to be into it at times. And I think the influencer business is incredibly sustainable. I just don’t think it’s sustainable for every person, every minute. And to your point, some of them have other entrepreneurial capabilities.

But that seems like the path out. 

But how many people are going to be able to be Emma Chamberlain, Logan Paul, and Mr. Beast? There’s a lot of brands that have been started by a lot of people. When I did Empathy Wines years ago as a DTC brand, I knew that I could do it because I was an operator. A lot of these people are not actual operators or won’t find a partner operator that’s good. I think that it’s an “and” conversation, not an “or” conversation. I think there’ll be plenty of people that will continue to be a personal brand in perpetuity, just like there are celebrities who get paid to be celebrities in perpetuity. To your point, some of those celebrities, like Jessica Alba, Reese Witherspoon, Ashton Kutcher, Ryan Reynolds, Kevin Hart, and the Rock, had that DNA. But I do think the long tail of influencer is a sustainable business model. I don’t think every human, nor most humans, can do it forever. They’ll ebb and flow.

Do you think it’s harder because the platforms have changed so much?

I think it’s easier.

What if you’re ebbing and flowing and in the middle of your down period, everyone’s attention moves from YouTube to YouTube Shorts?

What about when you ebbed and flowed as John Travolta, and then people decided they didn’t want to give you a chance again? He was out of the game for 15 years.

But his business was selling acting services. If you’re an influencer and you’re making branded integrations with your YouTube videos, and suddenly that market disappears because all the attention’s on TikTok, the core of your business is gone.

But you’re speaking to a world that I don’t think exists. Let’s talk it through. In the last 17 years, how many of the biggest platforms have disappeared off the face of the earth? Vine, which was only nine months old, right?

Dear sweet Vine.

I know. It was so fun. A lot of these people came from that. Actually, I think Vine will be historically looked at very interestingly because it’s what started shortform video at that level. But if you really look at the last 17 years — YouTube, Facebook, Twitter, Instagram, Snapchat, TikTok — it’s not like they’ve disappeared.

But it seems like the users are thinking about what’s next. Either way, you’re correct: we’ve rarely seen platforms disappear. We have seen them lose relevance, and in particular, I think the mid-form YouTube video, the vlog, used to be the gold standard — it’s what everyone wanted to build. And now everyone wants to build TikToks.

It’s so funny you say that because I actually have a slightly different take. It’s been crazy to me how many people are fired up that they’re going from TikTok to YouTube Shorts.

Interesting.

And using YouTube Shorts to get 2 million subscribers to their longer-form YouTube. Literally, my conversation with the TikTok emerging influencer shows their excitement to go long form on YouTube because YouTube Shorts has given them the subscribers they’ve always wanted because so many of them actually wanted to be YouTube stars, but it was easier to grow on TikTok. I think the old media landscape was much harder to navigate because you had to be chosen by humans subjectively, and now with these platforms, they’re empty pipes, and you, as a human, decide if you want to enter, if you want to be good at it, if you don’t, ebb and flow, in and out, and I think that’s good as long as the human is self-aware and doing the right things by themselves.

How do you bring all this to your clients? Again, we’re sitting at VaynerX. Its biggest company is VaynerMedia, the ad agency. For a lot of the clients now, the internet is not a foreign concept. Platforms are not a foreign concept. When you started, they were, this was a very new pitch. Now there are other great ad agencies that are native to the space. What’s your pitch now? How do you go and get business?

Our point of view is that we’re the best at today. We think the industry cares about yesterday way too much. Television commercials, programmatic banners, all the kind of old world. We think they’re also too bullish on tomorrow. Even though I was very bullish and continue to be on NFTs, the macro, we had clients who wanted to build million-dollar metaverses last year, and I was like, “Are you out of your mind? There’s like four people in the metaverse.” So they get excited about tomorrow. They’re way too religious about yesterday, and our pitch is that we’re the best of today. We do the media buying and the creative, the strategy behind that creative, for the 10 platforms — LinkedIn, Facebook, Twitter, Instagram, Snapchat, TikTok, Pinterest, et cetera. When we get the consumer insights out of that creative, the quantitative and qualitative data, the numbers and the comments, it allows us to have a better brief to then make the longer-form videos that are modern-day commercials.

We want to make the commercials that are going to be strong on Hulu, connected TV, fast channels, that’s our pitch. We’re an ad agency that just thinks that television ads are overpriced and bad, digital is overpriced, and you should do today’s best, and social happens to be that now. But if I started VaynerMedia in 1997, it would’ve been email, and then in 2000 we would’ve gone into search, and in 2041, we may be completely out of social, because maybe the attention is on virtual reality or metaverse.

I’m very agnostic. I’m not overly passionate where the attention is. Back to the TikTok thing, “Gary, what happens if TikTok’s banned?” I’m like, “We’ll go [wherever].” I have no emotion toward Twitter or TikTok or Facebook or Instagram. What I do have emotion toward is what you mentioned earlier — as long as I’m acting in my professional life, I understand that attention matters. I’d like to understand where the best price is to get that attention, and I’d like to be good at bringing value with the videos, words, and content because I know that providing value will always work for the business.

You talk about attention like a commodity like you can price it and sell it.

It’s pretty ruthless, actually, just from a business sense. You’re talking about it like you’re trading oil or gold or something. I am a news person. I think about attention in a very different way. I watched one of your TikToks the other day. You were telling people how to make great content, and you said something like, “If you’ve got a thought, just Google it, find an article, green screen yourself in front of the article. This is how you can capture attention on TikTok.” And I thought, one, “That’s brilliant,” and I told our team to start doing that with our articles. And then two, I thought, “This is the scariest shit I ever heard.” Because now we’re trading on other people’s trust — trust because of the news article — but we’re just doing it to harvest attention. I feel like there’s a danger there.

I think that’s what the news does. 

Do you feel like you have a responsibility to use the attention you harness positively, constructively?

In a massive way.

Because there are other people who don’t feel that way, who are just after it for traffic, for clicks, for attention.

And you’re right on the precipice where you talk about it like a commodity. But I know you, and I know you feel that responsibility. What is that responsibility for you?

I want to be historically correct. I want to feel good when I put my head on the pillow. I want to talk about the things I’m passionate about. I don’t monetize that attention directly the way the media does. I monetize that from awareness if people are interested in the things that I do. And then there’s secondary realities like, “Here’s a book.” Or people will come and see me speak, thus rendering my speaking fee high. Or I make a wine, and I’m like, “Hey, I think this is a better $20 wine.” And that attention gives me the opportunity to ask for an opportunity.

I do think attention is the most important commodity in the world. I don’t think of it like, “I bought it for a dollar and sold it for a $1.02.” I think of it like when you have your children, before they’re 18, that attention is everything in the framing of how they’re going to live their life, and you better take advantage of the attention. When you’re a business person, if you get attention, you get a chance to tell people about your products and services. It doesn’t mean they’re going to buy it.

I actually think one of the biggest issues of people who go [the] patient [route] with attention is they expect people to buy stuff from them after they’ve done a good job by getting the attention in a good way. And I always tell them, “You’re not entitled to them buying anything. You’re entitled to getting a chance for them to know about it.” So, that’s how I think about it.

Let’s end with VeeFriends. VeeFriends is maybe the ultimate example of you having a lot of attention on yourself, and you sold a product to consumers in a way that, apart from the wine, I don’t think you’ve sold a lot of products to consumers.

Correct. Those are the two moves. Sneakers a little bit, books a little bit.

And I hear you’ve always wanted to have IP, so you found a technological opening to create an IP franchise.

NFTs were pretty weird in that moment, right? They were pretty bubbly. People were buying them way too high. The market has crashed.

Do you have any regrets about that whole situation?

Not really, because… I mean, micro regret. I made a ton of videos saying that 99 percent of these NFTs were going to zero, and I made a ton of that at the height. So that’s why I’m able to answer “not really” because I was talking about it in a very macro way.

The other thing was that it was important for me to make my NFTs a part of something physical. So VeeFriends Series 1 came with three tickets to a super business conference called VeeCon. The price of the mint was worth the conference in itself, and then Series 2 came with trading cards that have created a lot of demand on eBay and things of that nature.

So I feel macro good. Of course, there’s a million things you want to do a little bit better after getting overly excited during moments along the way. Back to the responsibility I feel making content, when VeeFriends came out in May of 2021, it was a very young market, and then things went bananas. So in August, September, and October of that year, I started changing my content from, “Hey, this is something you need to learn about,” to “Hey, 99 percent of these are going to zero.”

To your point, NFTs are in the macro — pricing, not the technology. The products — the Beanie Babies of it all, not stuffed animals — are going to be here for a hundred years. The Beanie Babies and the Garbage Pail Kids of it all. Right? This was always about the macro technology, and there was unlimited content [where I said] 99 percent were going to zero, but people will hear what they want. 

Well, because they’re paying you money for a thing, right?

You have to understand, they paid money for a thing in May, which, again, came with physical items and the NFT was added.

That’s a reframing, right? So now the value is the physical items. 

It wasn’t a reframing. It really wasn’t. [I said], “There’s a collectible. I will spend 50 years trying to build this IP. Let’s see what happens and if I’m capable. [Also] here is the conference that comes with it, and this is how it’s priced.” One great thing about documenting everything and doing this all the time — it’s there.

I also have the benefit of genuinely believing that I’m going to make people fall in love with Optimistic Otter and Impatient Panda. And that becomes a Marvel and Pokémon journey over the next two decades. You really touched on something so important for me: what’s the person’s intent? You said, “Do you have a responsibility for your content?” Yes. That’s why I put out what I put out.

Do I have a responsibility to make this a big thing? I sure do. A lot of people want to believe that I’m going to be able to pull it off, and I believe I’m going to be able to pull it off. So I think it’s the intent, but you can’t just have intent — the actions are going to become what everyone is judged on. And I take that stuff seriously.

What do you think the timeline for VeeFriends and then, to use your word, macro for NFTs is to become serious, to become meaningful?

Series 1 is meaningful now. Even with an 80 percent, 90 percent decline, it’s dramatically, massively above what people paid for it. But to your point, 10, 12, eight—

Yeah. It’s just going to take time to get millions of people to care about Rare Robot… And I started a TV production company to do animation. I signed the kids’ book deal. We’ve done toys already with Macy’s and Toys “R” Us. It’s just a lot of work. It takes time.

But I think what’s cool about NFTs is when you bring utility in the smart contract, that was always what gave me peace of mind. To your point, Empathy [Wines] selling wine gives peace of mind. When you’re selling $40 wine for $20, people are going to like it. VeeFriends, what gave me peace of mind was the collectible cards, the access, and then the super conference — and then the access that comes along the way, like different mini events, Burn Island. I’m working on it every day.

Meaningful comes in a lot of different ways. For a far majority of the audience, it’s already been ROI meaningful, and now the collectible sits there as an added value. For others, to your point, that maybe bought it at higher prices when it was all hype, I still got a lot of work for them probably to be fulfilled. Because they didn’t buy at the mint price. And so, that’s something I need to work on forever.

I guess I meant meaningful in the sense that it’s an NFT, but NFTs are the technology that enabled you to introduce the IP.

You mean the macro NFT? Got it.

Right. But the idea that we’re out there buying and selling NFT collectibles is not a mainstream idea. Right?

It was a very bubbly idea, but it’s far from the mainstream. When do you think it goes mainstream?

10 or 12 years?

Yes, I think because they’re going to be about utilities. One of the analogies I used all the time was ticket stubs. You go on eBay right now, you will hit the ground [running]. Every Phish concert, every sporting event, just unlimited ticket stubs. Similar with NFTs. I think all tickets to Madison Square Garden in a decade are going to be NFTs. To me, nothing changes the way people collect. The reason I thought 99 percent would go to zero is because 99 percent of sports cards are zero, 99 percent of comic books are zero. The 1 percent get really interesting. Jordan rookie [card], Spider-Man number one. So I think 10 years.

AI is going to speed up a lot of the Web3 movement. Because I think right now, back to using other people’s IP, green screen, I think, is more of a media function of the way reporting works. But I think what’s happening with AI creative and information is: what’s the source? And a lot of big companies are starting to think about litigation with these AI companies. 

You got another hour?

That’s another show. We’ll be back for that show. 

Gary, you’ve given us way more time than anticipated. Thank you so much.

Thanks for having me.