Gary Vee’s 2026 Marketing Playbook

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0:49Gary Vaynerchuk:Instagram and TikTok look nothing like television. Let me explain. If Entrepreneur Magazine right now on its Instagram or TikTok posted, you are not reaching your followers on Instagram completely like email. You are putting content into the interest graph. And there will be hundreds, hopefully for you millions, of humans who will see the content based on what we have shown the platform we tend to be interested in. You are eliminating the potential of consideration by not making content that will find its potential audience. We are no longer in social media, Jason. Interest media is here. Social media is dead.

1:22Jason:Running a business means solving problems. I tell you how the smartest entrepreneurs do it. Hi, I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine, and this is Problem Solvers.

1:36Jason:If you want to master marketing in a social media era, this conversation is for you. I am talking with Gary Vaynerchuk. Of course, you know Gary Vaynerchuk. What you might not know is how deeply sophisticated he is as a marketer. Today, we are talking about some news at his company, some shifts that they're making. But after that, we get into the incredible weeds, get really geeky on how to think about the funnel today and how to structure a team for maximum nimbleness, maximum responsiveness, so that no matter what kind of brand you are, you are able to communicate to exactly who you need to reach at the moment in which they are most likely to be listening.

2:26Jason:Fascinating, super detailed conversation. Really excited for you to hear it. Here's Gary. Gary Vaynerchuk, a man who needs no introduction when talking in the world of entrepreneurship. You bring me news today, don't you? I do have some news.

2:39Gary Vaynerchuk:It's funny. A lot of people see me as a public figure or speaker, or motivational speaker, author, content creator, but I've been very feverishly building a very large marketing agency holding company, and we're growing up over here.

2:55Jason:Yeah, you sure are. And I know that there's some big news. Actually, wait, you know what? Before we even get to it, can I just pick up on that thing that you just said there? Because people know you for your personality. They know you for your influence, let's say, and they don't necessarily know that you've built this incredible marketing agency. Something that I have noticed about the people who succeed the most in the world of content and ideas, and I want to say this to you to hear you react to it, they're not actually often content first people like me. I came up making content in magazines.

3:29Jason:They're actually marketing people. They're people who understand how to connect with audiences and then figured out how to build great content.

3:35Gary Vaynerchuk:And I would say for me personally I'm also an operator right before anyone who knew who I was on earth I was a child literally a teenager who started the process of building the largest wine store in the country that's like real life that happened you know and and and then obviously you know Vayner X my holding company started with Vayner Media we're about to talk about my beloved small business agency Sasha Group being rebranded to Chuck Media you know we're talking about hundreds and hundreds and hundreds I mean it's not gonna be long before I ping you and say hey do you want to talk about VaynerX doing a half a billion in revenue we're on the doorstep and you know that's that's humbling to be to be very frank for a guy who has a lot of ambitions and bravado like we built one of the largest independent advertising agencies in the history of the industry Matt mad men in the history of the industry from like the most improbable angle like literally here comes a kid I was 34 so I don't know I think I was a kid but I'll be respectful that not everyone thinks that here comes a guy who's making wine videos on the internet and he puts a flag in the ground that he's going to build a big advertising agency Jason I you know I caught a lot of flack on Twitter, you know, and the ad magazines were not kind about Wine Boy, Madison Avenue.

5:03Gary Vaynerchuk:And yet here we are 15 years later, and it happened.

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5:43Gary Vaynerchuk:Yes, comma. I built Wine Library because I was such a good marketer, and I was a good operator and salesman, and like a good guy and had good retention of employees, all things that I used for Vayner. But what VaynerMedia is, is that you had a human that was out flanking everyone in contemporary marketing in the 90s and early 2000s when it was website, email, Google search, blogging. I built a firm that did contemporary marketing. Madison Avenue still does not do contemporary marketing. I've been doing this for 15 years. And now the day of reckoning is here. The people that are television commercial first, classic marketing, traditional first, the ones that are yesterday's digital marketing first are being upended, feeling the pain to the social first agencies and we're the largest of that.

6:40Jason:Well, then that's a good tee up for the actual news. So you said it a moment ago, but really unpack it here. So you've had this company, the Sasha Group, which has been focused on small business marketing and it's being rebranded and also refocused. So tell me what's going on and tell me why.

6:56Gary Vaynerchuk:There's so much demand for VaynerMedia. It starts to get too big where it becomes not mad. There's a lot of corporate, this is just very nerdy, but luckily this is why I think you're the right. We can nerd out right here, right now. This is business nerdy. Look, we're operators and we're strategizing and you know get keeping so many brands under one roof is like challenging and has all different dynamics it's kind of like sometimes you need to lose 15 pounds to get like tight like the the concept of chuck media being another agency that's going to be just as big as vayner media look i'm no i'm no genius this was done a long time ago wpp and omnicom and ipg and publicis they have many agencies that look similar-ish with subtle different strategies and they've built very large holding companies and are all publicly traded and we're building the next great big large massive holding company and Chuck Media is the next piece of that puzzle.

8:00Gary Vaynerchuk:A place where Fortune 500 brands can get the best contemporary marketing and a place where I can elevate a lot of my great talent there's a lot of kids in vader media that i think are ready for the prime time but we're big and so it gets a little corporate and it gets a little slower to get promoted and so a lot of opportunity for people to flourish and chuck media and just allows us to go to where i want to go to i want to have the advertising agency that does billions and billions and billions in revenue as a holding company and you need more than one or two agencies to do that

8:33Jason:and so here we are all right so we've got the sasha group which used to focus on small business is being rebranded as Chuck Media and it's going enterprise. So now you're going large. And there are two things that I want to understand from you. Number one is why the move away from small business there. And then number two is you keep saying the word scrappy. And in the announcement that came out from your company about this, it emphasizes over and over again, nimbleness that we're going to bring a startup attitude to these enterprise brands. So that tells me that there's something, even though you're moving away from small business, there's something about the nimbleness and scrappiness of small business that you think large brands are missing right now that you want to bring to them?

9:15Jason:Can you unpack that?

9:16Gary Vaynerchuk:I can, sir. Number one, I'm a small business guy. So, you know, stay by for another text or email from us. Like, you might have another exclusive soon because I am strategically doing this because it's what I need to do. I have more deal flow and opportunity in SMB than I do in enterprise. So this is a strategic move to set up my next chess move. So we'll see how that plays out. And honestly, because I really do adore you and I just want to give it to you, I actually have three different things I'm working on that could scratch the itch of the SMB world. I'll have to figure out here over the next six to 12 months what I want to do.

10:02Jason:So that's that. All right, well, you know who to call.

10:04Gary Vaynerchuk:On the scrapping part, brother, I would say that, yeah, it's just, you know, you know, I'm even laughing because whatever the comms team wrote you, A, I don't even know what it is. B, it's just so in our ether. Even, you know, VaynerMedia itself has more of an entrepreneurial spirit than your average Fortune 500 massive company. This is not lost on you. every company takes the DNA of their his or hers founder right like I am who I am like you know it is what it is you know I'm wearing a I'm wearing a sweatshirt right now of that has a picture of the sweater my mom knitted me because my family couldn't afford a$25 Jets jersey and my mom didn't want me to feel left out when I was playing football outside in Edison New Jersey I am who I M.

10:53Gary Vaynerchuk:And yeah, I mean, look, don't forget, I'm sure not lost on you, Vayner Chuck, right? Like this is, this is the extension of my last name that I'm very proud of and want to honor. And these are, at some level, they're identical twins. And in some levels, they're twins that don't look identical. What is that called again? Fraternal? So, you know, I think, I think that's how I think about it and i'm excited about it yeah but let's go a little deeper there because even though that

11:24Jason:is your dna and so that is the natural thing that someone is going to expect for and seek when they're going to be working with you and your companies you're also making a statement here about what large brands need now and i'll give you some context i remember i'm sure you do too when the lights went out at Super Bowl, whatever that was, and Oreo turned around that really fast, funny thing, everyone's minds exploded. Because at the time, it was very hard for large brands to move fast with marketing. Anybody who's been in a large brand understands there's layers and layers of review, and the lawyers have to see it, and it just slows things down.

12:05Jason:In a world in which if you're one beat behind by the time you speak, everyone else has moved on. So there's something here that you're saying that brands need, that there may be missing. And I'd love to hear you articulate that for anybody who works at a large brand or frankly, anybody who's building a brand and wants to be mindful of how scale could possibly slow them down.

12:26Gary Vaynerchuk:I cannot believe you brought that up. I brought it up last night at dinner with a bunch of CMOs. when that happened I think that was 13 I within 3 minutes of the tweet not the aftermath 3 minutes after the tweet I could already see it moving A, I wanted to find out if we did it because we were working with Mondelez and I was like whoa whoa whoa and it wasn't us but we were in the mix of the war room 2, I sent a company wide email remember this so the company wide email three minutes after the oreo thing happened all in my entire email like i often do all in the headline and it said our company has changed forever wow that was it we had been preaching for four years about speed volume relevance at scale social first attention contemporaneous relevance leads to consideration leads to purchase things are changing.

13:29Gary Vaynerchuk:I will tell you that that dream, that moment has been realized at scale. What I would tell everyone is this. I'm going to go very, very nerdy. Here we go.

13:38Jason:Please.

13:39Gary Vaynerchuk:There's something called the mid funnel now in marketing. It's existed. We're redefining it. It's organic social media, Jason. Every company listening needs to invest as much money as humanly possible, cutting from every aspect of their business to funnel into a production capability to make scaled social media content that is contextual to the distribution channel it's posting on whether that's linkedin or youtube shorts facebook or snapchat spotlight even extending into things like pinterest podcasting and sub stack they must make that content contextual to the platform both from a relevant standpoint but also from a format standpoint understanding what gives you the highest propensity to create organic reach which is predicated only these days on relevance the ai algorithms of these news feeds are written to understand if it is relevant to people and to continue to feed people at scale if it is and not feed it if it is not what i would call the interest media era not the social media era and that in the mid funnel when you are fortunate to have something perform then requires companies to send it down to the lower funnel performance and have media amplify that asset with a slight tweak to create cac and ltv and roas but also take it from the mid funnel what's successful and send it up to brand land and consider running it millions of dollars amplifying an organic successful piece of content as if you would do a TV and or my friend use it as the brief to do a campaign or something bigger this my friend in two minutes I just articulated actual real life 2026 marketing that the next influencer like Alex Earl or Cooper or Beast and every fortune 5 ,000 not even 500 the private equity or brands must understand cold because demand creation is one of the last things that's going to be left in an AI universe as a competitive advantage.

15:51Gary Vaynerchuk:And whoever knows it best and whoever executes that best will win.

15:57Jason:Now tell me how to structure a team so that that can actually happen. How do you make sure that you can go from idea to execution fast enough that you're still playing at the speed of

16:08Gary Vaynerchuk:culture whether you have a internal or external or jv structure so we at vayner media are obviously the agency of record for many people on this there are some teams that take it internal there are some teams that work in vayner collab a jv with us pepsico famously with pepsi we we are many of the employees there are many of the employees here's how you do it you have a creative captain the you know they used to say the throat to choke i don't know if that's politically correct anymore but the person the person in charge right there's a human on your logo who is in charge she or he is the one you need to build a production team not a creative team not people pontificating ideas jason in a room slow and then outsourcing the making no no you're a production team that happens to do creative media strategy you need a relevance strategist something that that we have that nobody else has.

17:04Gary Vaynerchuk:Humans that are paying attention and using AI and research and everything to understand what is popping, what matters, what is relevant to the consumers we're trying to reach, and how does our brand interact, inject, play with, jam on that. You need paid team, strategy team, creative team, all on the same team, not separated like every company does. You need a legal, if you're a Fortune 500 person, as a brand, part of the full team, in case you are a financial service, an alcohol, a fashion brand, lighter. They're worried about brand. You need a KPI, organic views achieved. Everybody judges everything on did it get views?

17:48Gary Vaynerchuk:The end. Not Jason saying that that's not the right color for entrepreneur, like that's off brand. Not me pontificating, I got a big, no, no. Doesn't matter. Post it, understand it. this structure that we you know to your point i'm glad you asked and you can see my passion for it's maybe even bigger than the thesis we won chuck media will win because we know how to operationalize our teams and how to give feedback to the clients we have something called elephant meetings internally where the leaders of our account must bring a client into a meeting to address the elephant in the room because jason almost all of our clients after hiring us to be vayner media ask us to be widening Kennedy.

18:33Gary Vaynerchuk:They don't even realize they're doing it. It's in your subconscious. It's in the inertia of corporation. You saw what I just did here. We do that for 25 hours before we start with clients over and over different ways. And by the third week, they want to debate if the color is on brand. We're like, what are we doing here?

18:53Jason:Right there. They naturally slow down, which means that you naturally need to be either pushing or setting those expectations.

18:59Gary Vaynerchuk:They naturally go to television subconsciousness. Got it?

19:03Jason:Yeah.

19:04Gary Vaynerchuk:They don't realize that debating something in the conference room is more expensive than the content cost to make. And we can get insights from it if we actually post it.

19:12Jason:I got to go back maybe two minutes in that really excellent outlay of strategy there and ask you to unpack strategy. No, sorry. Relevance strategist. I have never heard the term relevant strategist. I did not know relevant strategist was a job. It's a job in one place on earth so far. Right where you're sitting.

19:36Gary Vaynerchuk:Yes, sir. we believe that brand strategy which is what strategy has been has been commoditized with with ai with llms and just has lost its value over time we still value it but we think it's done pretty quickly and easily and then the next day happens like it's not hard to sit down and say you know what does toyota represent or what is you know kmart i don't think they're in business

20:00Jason:but like you know like what did they represent what did they represent or what does marvel