A 95-minute sit-down where Gary Vaynerchuk walks through every company he runs, the content machine behind them, and why he thinks creators are the next Fortune 500.
Posted
2 days ago
Duration
Format
Interview
sincere
Views
67.3K
1.2K likes
57 · 43
Big Idea
The argument in one line.
Creators who keep posting at volume, staff up around themselves, and refuse to trade audience trust for a quick deal can grow personal brands into enterprise-scale companies.
Who This Is For
Read if. Skip if.
READ IF YOU ARE…
A founder or operator building a personal brand alongside a real company who keeps pausing content when the business gets busy.
Someone running or starting a social-first agency who wants to see how a $400M shop structures itself around production instead of decks.
A creator weighing equity or sponsorship deals who wants a clear rule for when promoting a partner breaks audience trust.
A podcaster or video creator deciding between lo-fi volume and premium polish.
Anyone curious about live shopping, alternative sports leagues or kids IP as the next places attention is moving.
SKIP IF…
You want a step-by-step tutorial; this is a wide-ranging interview with tactics scattered through it.
Heavy profanity bothers you; the guest swears constantly.
TL;DR
The full version, fast.
Gary Vaynerchuk argues the gap between companies that understand social and those that don't has never been wider, and that personalities with audiences are becoming the next generation of major companies. VaynerMedia wins by acting as a production company: make social content at scale, read the results, then push winners into ads or bigger campaigns. His own brand runs the same way, with a 20 to 30 person team chopping long-form conversations into a target of 1,000 posts a day. The lessons: never stop posting, hire more people instead of cutting content, reinvest rather than buy toys, put people you've known for years in charge, and never spend audience trust on a deal you don't believe in.
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Cold-open montage: the biggest-myth answer, the 1,000-posts-a-day line, and the Crush It to billion-dollar-creator thesis.
00:59 – 03:44
02 · Inside His $400M Media Empire
VaynerX explained: three agencies (VaynerMedia, Chuk Media, Tamara Group) plus VaynerSpeakers, near $400M a year, with Gary as active CEO.
03:44 – 06:24
03 · The Ad Agency Built Like a Production Company
Why VaynerMedia sells itself as a production company: make social content at scale, read the data, push winners down to performance or up into the big idea.
06:24 – 13:39
04 · Why Big Companies Are Losing to Creators
The haves-versus-have-nots thesis, inertia inside Fortune 500 marketing, clients who get it, word-of-mouth as the agency flywheel, and the barter-media side business.
13:39 – 17:14
05 · How He Plans to Post 1,000 Times a Day
The 20-30 person personal-brand team, the long-form-then-chop pyramid, and treating every podcast and speech as a production day.
17:14 – 20:54
06 · Quantity Is Not Debatable, Quality Is
Volume as the only objective variable, why most of his real strategy work stays private, and caring only about the 1% who actually know you.
20:54 – 23:35
07 · Why He Replies Kindly to Haters
Abundance over scarcity: why people who tear him down make him sad rather than angry, and why almost nothing is zero-sum.
23:35 – 26:54
08 · The Lost Story of How Twitter Built Gary Vee
The irreplaceable hire is the platform-native editor; 2007-2011 Twitter engagement built the brand; post natively everywhere; honesty to self is the personal-brand test.
26:54 – 28:47
09 · Why Operators Are About to Win Everything
AI removes the need to train others, so the thinker-doer wins; the host is told he is minutes in, not behind, and that quitting resets the clock.
28:47 – 31:53
10 · No $200K Salary Until His 40s
Hire more players instead of pausing content, reinvest instead of buying toys, and hold your breath longer than everyone else.
31:53 – 36:09
11 · Why He's Running Toward TV as Everyone Leaves
VaynerWatt, his quiet TV production company, how TV deals are structured, and why every new medium is an iteration of an old one.
36:09 – 41:25
12 · Why Alternative Sports Are About to Blow Up
Unlimited distribution killed the channel gatekeeper, so leagues like pickleball and wiffleball now compete on merit; go slow instead of raising big.
41:25 – 44:32
13 · The $1 Trillion Live Shopping Boom in China
Live shopping defined, why it is QVC on social, China's $1T GMV figure, and the coming era of salespeople becoming stars.
44:32 – 47:09
14 · Should You Post Lo-Fi or Premium Content
The answer is 'and': test concepts lo-fi at volume, then rebuild winners in premium; work is a variable nobody can skip.
47:09 – 50:25
15 · Why He Only Hires Family and Old Friends
Leaders across his 13 companies are family or decade-long colleagues because they know how he operates; his career weakness has been lack of candor.
50:25 – 51:22
16 · Why He's Not Scared of It All Falling Apart
Daily firefighting without taking it personally, because his identity is not tied to his career.
51:22 – 56:07
17 · His Early Bets on Facebook, Twitter and Uber
The angel portfolio (Facebook, Twitter, Uber, Snapchat, Venmo, Liquid Death), why mindset is what makes success sustainable, and backing proven founders.
56:07 – 57:59
18 · What People Get Wrong About VeeFriends
VeeFriends is not an NFT fad; the tech is sound, the bust looked like the 2000 dot-com crash, and physical collectibles were always part of it.
57:59 – 1:02:03
19 · His Plan to Become the Next Walt Disney
VeeFriends as a 20-year kids IP play built on character lessons like gratitude, with books, comics and Hollywood interest already arriving.
1:02:03 – 1:03:33
20 · The 5-Year Bet That Built VaynerSports
He expected five bad years starting with small deals and offensive linemen; it went exactly to plan and is now a top independent agency.
1:03:33 – 1:05:36
21 · Never Do a Deal With Your Favorite Athlete
Negotiate for more content output and whitelisting rights instead of access to a hero.
1:05:36 – 1:08:24
22 · Inside VCR Group, His Restaurant Company
The restaurant group's operators, the brands, and his origin story of restarting from zero at 34.
1:08:24 – 1:10:02
23 · Why He'll Never Compromise His Audience
Keeping the public persona separate from his business interests, and why trust is the whole game for anyone building around an audience.
1:10:02 – 1:14:03
24 · Why Creators Are the Next Fortune 500
The Individual Empire book thesis, his own 85% problem, and self-awareness as the zero-to-one starting point.
1:14:03 – 1:35:18
25 · Quickstrike Questions
Rapid-fire: the Airbnb pass, giving more than you take, the Jackie Robinson card, his parents, detachment as his edge, Disney, and how big the empire can get.
Atomic Insights
Lines worth screenshotting.
VaynerMedia calls itself a production company that happens to do creative, media and strategy, not an ideas agency.
Fortune 500 marketers lose to creators because of inertia and internal scorecards, not because they lack budget.
Quantity is objective and quality is subjective, so volume is the one content variable you can't argue with.
The hardest content hire to find is an editor who natively knows how each platform rewards different cuts.
Gary Vaynerchuk built his early brand on Twitter from 2007 to 2011 mostly by replying to people, not by posting.
His personal media team shrank from about 50 people to 20 or 30 by using AI tools, while output targets went up.
When the business gets hard, the fix is hiring more people, not stopping content; quitting resets your audience clock to zero.
He did not pay himself anything like $200,000 a year until well into his 40s.
A pickleball team he bought for $500,000 is now in a market where teams sell for around $20 million.
Live shopping in China was cited at about $1 trillion in gross merchandise value this year.
Test ideas with lo-fi content at volume, then rebuild the winners with premium production.
His biggest leadership weakness, by his own account, has been withholding candor from people he cares about.
VaynerSports was planned around five bad years, and it went exactly that way before it started winning.
Never do a sponsorship deal with your favorite athlete; you'll overpay for the chance to meet them.
Always negotiate whitelisting rights, so one piece of athlete content can run as ads indefinitely.
Care Bears was cited as doing over $500 million a year in licensing.
He passed on investing in Airbnb after the founders emailed him from an airbedandbreakfast.com address.
Asked for his unfair advantage in one word, he answered: detachment.
Takeaway
Volume, patience and trust build the empire.
OPERATOR LESSONS
Post relentlessly, staff up instead of pulling back, reinvest longer than feels comfortable, and treat audience trust as the one asset you never spend.
02Inside His $400M Media Empire
A holding company can run several near-identical agencies side by side so competing clients, like two airlines, can both be served without a conflict.
VaynerX does roughly $385M to $400M a year across three agencies and a speaking bureau, with each unit's leader reporting to one active CEO.
03The Ad Agency Built Like a Production Company
Traditional advertising splits ideas, production and media across separate firms; collapsing them into one content-production shop is the structural edge.
Make social content at volume, read both the numbers and the comments, then send winners down to performance ads or up as the brief for a bigger campaign.
Experiential activations and product sampling count as content when you film them, so one budget buys trial and footage at once.
04Why Big Companies Are Losing to Creators
Big companies lose to creators not from lack of money but from inertia, comfort and internal scorecards that reward the old way.
A new executive who does not understand social will often retreat to TV spend and call it brand equity, even when the results say otherwise.
After the founder-driven early years, a mature agency's growth engine is word-of-mouth results, not the founder's content.
Barter media trades unsellable inventory for media credits; doing it with creator and social content instead of late-night TV fixes a historically shady model.
05How He Plans to Post 1,000 Times a Day
Long-form interviews, talks and podcasts are raw material; the scaled output comes from chopping each one into dozens of platform-specific pieces.
Treat any long conversation as a production day, because the volume of content needed to dominate cannot come from posting alone.
A personal-brand media team of 20 to 30 people, trimmed from 50 using AI tools, can target 1,000 posts a day across 100 handles.
06Quantity Is Not Debatable, Quality Is
Volume is the only objective content variable; quality is subjective and only the audience's response settles it.
Most valuable strategic advice happens in private rooms and can never be published, so public content will always look more general than the person.
Optimizing for the 99% who do not know you can cost you the respect of the 1% whose opinion actually matters.
07Why He Replies Kindly to Haters
People who attack someone with a big platform are usually looking for a bump; pity is a more useful response than anger.
Treating another person's win as your loss is a scarcity mindset, and almost nothing in business is actually zero-sum.
08The Lost Story of How Twitter Built Gary Vee
The scarcest content hire is a post-production editor who natively knows what wins on LinkedIn versus Shorts versus Snapchat.
Senior content leaders should have done the work themselves, or they cannot manage the people doing it.
Early Twitter growth came mostly from engaging with others, not from posting more.
Post natively per platform; reuse something across platforms only when the results show it wins on both.
A strong personal brand comes from being honest about what you actually like, even when it confuses the people whose approval you just earned.
09Why Operators Are About to Win Everything
AI lets one person think and execute without training a team first, which favors operators who can do both.
Stopping content for years resets you to zero, so consistency beats occasional greatness and burnout is the real enemy.
10No $200K Salary Until His 40s
When the business struggles, the fix is hiring more people, not cutting the content that feeds the brand.
Money spent on toys, whether cars or vanity projects, is money not reinvested in the business.
Paying yourself little for a long time compounds; the guest took under $200K a year until well into his 40s.
11Why He's Running Toward TV as Everyone Leaves
Streaming has erased the line between broadcast and digital, so a TV show can be both a network deal and a marketing asset.
TV deals come in many shapes: sell outright, produce for a fee, fund and license, or co-produce, and leverage decides the terms.
Every 'death of a medium' is really an iteration; a filmed podcast is a 1950s radio-to-TV show again.
12Why Alternative Sports Are About to Blow Up
When distribution was limited to a few channels, gatekeepers decided which leagues existed; social made inventory unlimited and put sports on merit.
Judge a new league by whether it can win attention and keep it, not by whether you personally like the sport.
Leagues fail like startups do: raising and spending big too early, instead of growing slowly toward profit.
13The $1 Trillion Live Shopping Boom in China
The strong form of live shopping is one-swipe, in-stream checkout, not a stream with an affiliate link attached.
China's live shopping market was cited at about $1 trillion in GMV this year, covering cars and homes, not just trinkets.
Live shopping will make stars of natural salespeople who would never win as conventional entertainers.
14Should You Post Lo-Fi or Premium Content
Lo-fi and premium content can coexist; luxury fashion houses chase streetwear collabs because premium alone risks irrelevance.
Use lo-fi content at volume to test concepts, then remake the winners in your premium visual style.
Work volume is one of the biggest variables in success, and four hours a week will not build a media business.
15Why He Only Hires Family and Old Friends
Run many companies by putting people you have known for a decade or more at the top, because they already know how you think.
Speed, not loyalty, is the real benefit of long relationships: less explaining, faster decisions.
Withholding candor from people you care about is a leadership weakness; direct negative feedback, without passive aggression, is a skill to build.
16Why He's Not Scared of It All Falling Apart
Running many businesses means firefighting every day, which only works if problems are not taken personally.
Separating your identity from your professional career is what lets you stay calm when things break.
17His Early Bets on Facebook, Twitter and Uber
A long angel track record can disappear from public view once someone becomes known for content.
Businesses built on insecurity can grow fast but tend to crash; self-awareness is what makes success last.
Founders who have truly won before are safer bets, but check what their claimed 'exits' really were.
18What People Get Wrong About VeeFriends
Scams around a new technology do not make the technology a fad; the dot-com crash looked identical.
Pairing digital collectibles with physical goods like trading cards hedges a project against a market collapse.
19His Plan to Become the Next Walt Disney
Character IP can be worth enormous sums; Care Bears alone was cited at over $500M a year in licensing.
IP built around a founder's fame fails; it has to stand on characters and stories that work without them.
Relatable flawed heroes and aspirational ones both work, but pick one deliberately.
20The 5-Year Bet That Built VaynerSports
A new agency in a relationship-driven market should expect about five slow years and start with small, overlooked clients.
Founder fame does not transfer automatically; the first prospects still asked who the agency had represented.
21Never Do a Deal With Your Favorite Athlete
Deals with a favorite athlete usually overpay for access; negotiate on content output instead.
Push for more posts and secure whitelisting so one piece of athlete content can run as ads long after the deal.
22Inside VCR Group, His Restaurant Company
Kind operators are easy to underestimate; tenacity often only shows up once you are in the foxhole together.
A restaurant group needs a celebrity face, a business operator and a kitchen operator; they are different skills.
23Why He'll Never Compromise His Audience
Keep the public persona separate from your financial interests and never promote something without making the incentive clear.
Turning down paying clients or partners whose product you do not believe in protects the trust that every future deal depends on.
24Why Creators Are the Next Fortune 500
Personalities with real audiences can become Fortune 500-scale companies if they build true enterprise value and a team around themselves.
AI keeps startup costs low, but scaling still requires raising operating spend on people once revenue arrives.
Getting 85% to 90% of the way on many fronts is a common ceiling for people stretched across many platforms and businesses.
Pick your format from self-awareness: writers write, charismatic people make video, good listeners interview.
25Quickstrike Questions
Give more than you take; it compounds, but only if you wait long enough.
Saying yes to every random meeting costs time, though occasional serendipitous coffees pay off big.
Lack of tenacity, mostly fear of what others think, holds most people back; realizing no one cares is freeing.
Glossary
Terms worth knowing.
Holding company
A parent company that owns several separate operating businesses, each with its own leadership, and sets overall strategy across them.
Conflict shop
A second, near-identical agency created so one parent company can serve two competing clients without either feeling its rival gets the same team.
CAC and LTV
Customer acquisition cost and lifetime value: what it costs to win a customer versus how much revenue that customer brings in over time.
Barter media
A trade where a company swaps excess or expiring inventory for advertising credits instead of selling the goods at a discount.
Principal ad buying
When an agency buys media inventory itself and resells it to clients at a markup, rather than buying on the client's behalf at cost.
Whitelisting
Permission for a brand to run paid ads through a creator's or athlete's account, using their content and handle as the ad's face.
GMV
Gross merchandise value: the total dollar value of goods sold through a platform before fees, returns or costs are subtracted.
Live shopping
Live video where a host sells products in real time and viewers buy inside the stream, often in one tap, like QVC on a phone.
Phygital
A product that pairs a digital item, such as an NFT, with a physical one, such as trading cards or a book.
IRR
Internal rate of return: an annualized measure of how profitable an investment was, used to compare investments held for different lengths of time.
M&A
Mergers and acquisitions: one company buying or combining with another.
JV
Joint venture: two companies forming a shared business or partnership while staying separate otherwise.
26:54 – 31:53denseOperators, reinvestment and patience
31:53 – 44:32steadyTV, alternative sports, live shopping
44:32 – 50:25denseContent mix and hiring
50:25 – 1:02:03steadyInvesting, VeeFriends and IP
1:02:03 – 1:08:24steadyVaynerSports and VCR Group
1:08:24 – 1:14:03denseTrust and the Individual Empire
1:14:03 – 1:35:18steadyQuickstrike questions
The Script
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So what's the biggest myth about Gary Vee? I think people think I'm stressed and I'm hustle and I'm hardcore. They'd be shocked to realize how detached I am from my professional success.
I could give a fuck. Give a... Gary Vaynerchuk is the man behind VaynerX, a $400 million media company and one of the most misunderstood personalities on the internet today.
I compete with every creator on earth every day. I'm trying to put out 1 ,000 pieces of content a day across 10 platforms, across 100 handles. I'm going to build such a fucking monster.
Most people don't know what Gary actually does. And for the first time ever, we walk through all of his businesses, discuss the one rule he'll never break with his audience, and confront what most people get wrong. about him.
Crush It told the world in 2009 that you can make $100 ,000 a year on the internet and everyone laughed at me. The people that are making a million dollars a year right now can actually make a billion dollars a year. Everyone's confused.
Everyone.
Everybody knows Gary Vee as an iconic voice on the internet, 50 million plus followers, but he is an operator, not a content creator. He runs VaynerX, a $400 million -plus media company, and is involved with six to seven other eight - to nine -figure companies. Stay to the end, and we'll tell you how it's all possible.
So you're saving my phone as Yoda. That's fucking amazing. That's very humbling.
Especially because I like green. I'm a big Jets fan, so it's double humbling. But yeah, because I think one of your superpowers is the ability to get very little bit of context and then give...
granular, prescriptive advice to someone that's very, very impactful. So I want to kind of glaze over some of your companies and just talk about kind of what those companies do, general trends. And if somebody is in that space, just kind of how you see that space evolving over time, given the amount of time that you've been in the market.
So let's give people value. Yeah. Let's start with VaynerMedia.
So let's just talk about what is that actual business and how are you involved in that company? So VaynerMedia is a contemporary ad agency. What that means for everybody who's watching, especially this kind of audience is My brother AJ and I were the guys in 2009 who were like, hey, social media is going to win.
Not television, not print, not radio, not direct mail. Like over this next decade, this new format of marketing, YouTube, podcasting, but mainly social media, it's the winner. And it is just literally a Madison Avenue ad firm.
Now, there's VaynerX, which is the holding company that holds VaynerMedia. Chuck Media, the rest of my last name, a new brand that I rebranded the Sasha Group, named after my father, which was an agency for small businesses. We now have Chuck Media that's just like VaynerMedia, really just a conflict shop so that if JetBlue and American Airlines want to work with me, which is very common at this point, everyone kind of wants to work with us, which is like fucking humbling.
I needed a way to do more business. And I even set up a third agency that's similar with subtle differences called the Tamara Group, named after my mother. And that stands for the Attention and Media and Relevance Agency.
And so those are three agencies. Then we also have our speaking bureau, you know, VaynerSpeakers. And those four companies are VaynerX.
And that's the one that will do 385, 390. We'll see how this year. So I want to be real with everyone.
It's almost 400. And that's, I am the active CEO. of that holding company, VaynerX.
So Ryan Harwood, who does Gallery Media Group and PureWow and Covator and Tamar Group reports into me. Mark Rolland, who runs Chuck Media, reports to me. And I am the active CEO of VaynerMedia and the active CEO and chairman of VaynerMedia, the biggest of those agencies.
And that is... That business and what I do for it. And what does it look like if JetBlue comes in the door?
What does that engagement look like? Is it like, what are your core KPIs and you back into it and deploy it to a specific department? Yeah, we are, you know, we're very unique.
We're about to get loud about this. I'm glad I'm giving you the exclusive. This might help a bunch of kids build bigger agencies than they might.
We're a production company that happens to do creative media and strategy. For the kids under us that are all doing this, that makes sense. They don't even know how to live without making.
But for kids under 35 that are doing all the good shit, let me tell you about what's actually happening in advertising land. There are creative agencies that charge huge retainers $3 to $20 million a year just to come up with ideas and decks. And when the client says, yes, I want to do that big idea, you then pay a production company to make a 30 -second video.
You then spend $30 million in media to make everyone see the video. And everybody that watches this fucking podcast or is listening knows all that is dumb shit from yesteryear. We were the ones that came and said social first.
Make content at scale at social. Extract the insights, the quant and the qual. When something does well, send it down to performance to create CAC and LTV and conversion or send it up to be the brief to the bigger idea because we know that the grandma, granddaughter content's crushing.
Now let's go make a tearjerker fucking video that's a minute 20 seconds and let's put that on YouTube and Amazon Prime and social not buy fucking cable TV 30 second spots. And that's why we built a monster. So we're a production company that does production of social content, long form video.
We do Super Bowl ads. We did fucking William Shatner's Shat My Pants Super Bowl spot last year for Raisin Brand. But we also do live shopping.
which is a new thing we do because I'm a beast in that. Oh, we're going to get into this. I know you're deeply passionate about that.
Oh, I'm deeply passionate. Experiential. So, you know, some of our brands are going to show up at the Super Bowl or NBA All -Star with like a booth and doing stuff.
We're going to do that for them. We're also going to film it, make social content. Podcasting.
You know I've been in this game forever. Our spine is social content, but we do experiential, premium video. podcasting, filming, sampling.
I love for CPGs to give out shit, film it, then it's content, but you're also getting trial. We're really progressive in that world. Like many kids that were inspired by my content, I've built epic stuff.
I always get the flowers on DM in real life. Hey, I built an $8 million agency because of you. $7 million agency because of you.
We were the ones that did that for the Fortune 100. what direct to consumer brands are doing and what influencers and humans and you're doing right here. Like we were, I was crush it.
That book was it. Let's zoom out and expand because clearly you're three sixer. You're doing everything and you're going to keep iterating and probably creating new companies underneath this whole AR VR to just feed what the market wants.
That's right. What do you think is just like, what's your macro thesis on just marketing period right now? That the haves versus have nots have never been more.
Divided. What do you mean by that? That everyone that gets social and podcasting and YouTubing and streaming and live shopping and influencer is crushing.
And that big companies are getting their asses kicked without realizing it's going to get much worse. What blows my mind is a lot of people that are the haves that are winning, they can do it on a shoestring budget. And then you have these companies that have a billion dollars on their fucking balance sheet.
Why are they not just... I would imagine that you're telling them. Why are they not just signing with 200 ,000 creators and just being more efficient with their dollars?
How things are scored inside a Fortune 500 company. Comfort. We're about to lose a client.
I'm not going to call out names. We're about to lose a client because the guy that became the new CMO who we've worked with in the past, he just does not believe in social because he doesn't understand it. And he'd rather hire an agency to do a television campaign.
And he'll hide behind academia of brand equity versus living in real fucking life. Let's flip it. Who's a client that you've had that gets it?
Michael Rubin. You know, our impact on fanatics has been enormous. Outside of Will Marcus, who I think has made Rubin a cultural public icon through, you know, the white party and all that.
Like, I'm very proud of. what we helped Fanatics build internally. Much of Fanatics' internal agency right now is former VaynerMedia employees, ones that actually were, only one key person was at Vayner through this transition.
But, you know, Pepsi, Mark Kirkham, the CMO there, deserves a lot of credit. Over the last two years, we were there for 12 years. Greg Lyons before him and Mark Kirkham, they...
They intuitively, like, fuck, Gary's right. Like, we got to get there. Some of the stuff we've been able to do with Mug Root Beer, we're just cooking.
Soon to be Scott's Miracle Grow. Love that. You know, because Nick Moraitis was our chief client officer, just went to become the CMO there.
Of course he's going to bring that talent, and he's going to bring us along, and we're going to crush for that gardening company. I mean, there's a lot. Jim Malachi at Bose, you know, I think really, really.
Carla Hassan at Chase is pushing. But Chase is a monster. So I'm empathetic.
Almost most of my clients get it. They have a lot of bullshit and red tape to get us to be the big dog in the company because the big holding companies, the publicists, the Omnicoms, the WPP, if people look that up right now, the people that are billion dollar public companies that do marketing, they're selling. These people, fake reports, fake technology, principal ad buying, which is fucking fraud, all this bullshit, but it works for 60, 70, 80 -year -old board members and CEOs in these companies because they're comfortable with that.
And that is why you've seen things like Gruins and Liquid Death and all the fucking rise of the individual empires that are being built around creators and all these CPGs is because... Fortune 500 companies are lost and are playing school and corporate, and we are playing real life. Let's divide the haves and have -nots, and what's that one piece of first prescriptive advice you would give to the have -nots?
For people that aren't in the game and they should be in the game? Stop being a bitch. Like, live in real life.
Like, and it's funny, I'm obviously going at it because I've got clearly a lot of pent -up... on, you know, I care, bro. You know me.
Yeah, I do know you. Bro, you know me different than a lot of people know me. You do care.
I fucking care. So if somebody pays me money, I fucking want them to win. You think I like watching kids that follow my shit carefully and prescriptively for free because what I put out publicly are starting to take market share from companies that are paying me because they listen better than people that pay me?
It fucking pisses me off. The advice is like, hey man, hey lady, do you live in 2026? Do you actually believe a 30 second video that looks like a commercial is gonna get any human being to buy anything?
Like who the, bro, who the fuck believes that? Could you? Comprehend being comic.
I just can't understand. I mean, we're on the same boat that we think that you get the asymmetric benefit from like a Super Bowl ad, but anything that's right below that or down to the volume play makes absolutely no sense. And they just keep, you know, the creative directors, the Cannes Lion Awards.
It's a whole fucking racket. And that's why for a lot of kids watching, come in. Listen, I'm winning.
I'm going to build a massive company, but you can come in too. And like, the industry needs it. But on the flip side, if you're good enough, you'd rather just build your own CBG or media company because client services fucking suck shit.
I would love to know, just to double click on just like that flywheel. So is the flywheel kind of you at the top as a social content machine? They come in to VaynerMedia?
No, it's not. What does that flywheel look like? In 09, 10, 11, 12, it was.
The flywheel is fucking word of mouth results. At this point, we're grown. We're 15 years old.
So you don't think there's a key man risk anymore? I always think there's a key man risk. Yeah.
Like, when you're the greatest, like, player on a team, like, losing you, like, that's going to be a problem. Like, how could we possibly be as good with me if Wine Library has not done as well with me not being there? Even though I'm literally running that company through my friend Brandon Warnke.
Best friend. since 14. Contextually, people don't even know there too.
You brought that from four to 60. Yeah. And by the way, it also went all the way down to 30 and I brought it back to 60 because of wine text.
Everybody sign up for wine text .com. Like, you know, I'm, you know, back to my 15 minutes. Like it was literally my dad for the first time ever being like, so let me get this straight.
You help all these other companies and you won't help your dad. I'm like, I'll help you now that you recognize that I'm the fucking guy that built the company. That's fucking funny.
Um, I want to go into more of these companies. I've never even heard of some of them.
And I'm a big barter guy. My friends call me Barter Simpson, a big arb guy. Tingley Lane Trading, what is that?
It's, you know, Josh Smith, I'm sorry. It's actually one of the companies in VaynerX that I didn't name. It's small.
Like, it's actually probably a function that should be brought into the other three companies. But what is the thesis underneath that? Barter Media.
You take bad goods, like expiring inventory, like Tropicana has a fucking orange farm. that they want to get rid of and they trade it they give it to you it's all fucking financial arbitrage and you give them media credits it's historically been a shitty black box bad business in madison avenue we wanted to do like the white hat version of it and josh smith's like a dear friend does a good job and basically it's like you've got 10 000 units of bad electronics and you're like fuck we can't sell this and if we sell it's gonna fuck up our brand let's Give this to a barter company.
They'll give us media credits in return. What used to happen is you'd get two in the morning fucking bullshit television. So it wasn't good for the people.
What we do is we do creator content, social content, good media. So it's been a nice little niche. A strategic liquidator.
That's right. I like that. We'll dive more into the whole entire ecosystem.
I want to go all in on just the individual empire, your personal brand, Gary Vee. What's the team and how are you involved? There's a lot of people out here.
that are early stage operators that are seeing the arbitrage of creating content as a founder -first company. And I think the biggest thing, I'm seeing it, I had done it formerly with Iconic and obviously now with Open Residency. It is hard to navigate, like, who do you hire?
What does that kind of, you know, feedback back and forth look like? How do you keep your eyes on the prize of maybe the other company and also build a media company? What does it look like today?
Like the Gary Vee business, the personal media business? There's, what do you think, Sid, 30 people? Sid obviously ran it for a decade.
Right now, Raghav and Nareya run it. Sid's still kind of involved because he's like almost in special ops. We're just doing a ton of things.
What do you think they have, 30 right now? Yeah, and that used to be 50 because we were using so much AI internally, open claw, clawed. So it's a 20, 30 person team, ebbs and flows, with two co -leaders at the top who are really the executive producers.
and are making sure my content is being produced and distributed at a scale that is pretty different than almost anybody in the game. And what is the thesis on that? And I would be under the assumption that like, I feel like the tweets have to be you.
I'm like more new to Twitter and I feel like you have to be tweeting all day long. And that's something very hard. Tweets are extra.
So this is why I'm doing this podcast for only two reasons. I fuck with you and I love you and I want you to keep, I know you're on the precipice of exploding and I know that this episode will do good for you. And two, I need content.
You need long form content that you can chop up down to a zillion different others. So the tweets are me, but now it used to really be me. Now it's just extracting something I'm going to say out of here and timing it.
So why don't you give us that machine underneath now? Is it, let's create as much content as possible, as many actual minutes of dense value. And then it's just, how do we chop this into words and videos and optimize them?
That's right. And by the way, I've fucking given everybody the secret for 15 years. Yeah.
Like I put out a fucking peer. The whole industry runs on a fucking deck I put out a decade ago called the Gary V Pyramid thing where make long form, chop it up. Everyone's like clipping agencies.
I'm like, motherfucker, I'm the first clipping. That's what I did. That was my innovation.
I did YouTube. I did DailyVee and DRock for the content, not for the vlog. I speak and spoke publicly for years for the content, not for the speech.
I went on podcasts. I went on Rogan and every other. Not to be on Rogan, though that was a big platform, obviously.
I'm not here to siphon brand equity out of your audience. At this point, a lot of them know me. Now, they might like me a little bit more if they realize who the fuck I am in a deep interview, but it's more about this is a production day for my content.
If you're not streaming, if you're not live shopping, selling, if you're not vlogging, if you're not podcasting, you're not giving yourself. a production day for the amount of content you need to dominate. I'm trying to put out a thousand pieces of content a day across 10 platforms, across a hundred handles.
And you know this, I was the post, you know, 10 to 15 times a day guy. And everybody was like going crazy five years ago, like 30 pieces of content a day. That's fucked up.
I'm looking to do a thousand right now. You know what's so crazy is I would never charge for a guest to come on. We've had people actually offer money to come on.
But what we do now is we offer extended production days where if a team and or a founder wants organic content, paid content for the website, and then we can line up specific questions and they can shop it up for whitelisting or anything like that. Makes sense. There's so many mutations of the game.
Yeah. So with that being said, I would just love your thoughts on just quality versus quantity. Quantity is non -debatable.
Quality is debatable. The end.
What's your thoughts? If you make 900 pieces of content a day, you can't debate that. You made 900.
Quantity is not debatable. Quality, what's quality? Subjective to.
And on that realm, are you just looking at just at views, basically, on that side? When it's organic, you can only get views if it's relevant. Now, you may not want something to be relevant.
Like, that's not how you see yourself. But this is... How do you look at deep and narrow versus kind of a bit more wide?
Like I would - Do both. I do both. So you do some sort of split between, because that's like probably like, probably the biggest question I was going to wait till later to kind of ask you is like, dude, I feel like so much of your content is kind of happiness and motivation and you have that effect on people, but people don't know about how deep you can go on the business side.
Is that by design?
So much of my hours are spent on things I can't share. You know, like when you and I through the years of your company, like when we're having like real conversations about like people letting you down or like we're strategizing how to grow your business, like I can't put that out. That's your fucking business.
You know, when I'm in a room with the CEO of fucking eBay or Rubin or fucking like 90 % of my life, I can't show. And I feel like those conversations to you are very native to that individual situation versus kind of this macro. And it's secretive to them.
And it's strategic. And it's like the different like. People make lots of money talking to me.
And if everyone saw it, their competitor could do it. Most of my day is spent not on things I can talk about. I'm also not interested in impressing anyone, bro.
Anyone that needs to know knows who the fuck I am. I think you're underrated. We already know about that.
And that's how everyone that's a fucking player thinks. That has spent time with me. I haven't spent time with every player.
But there are very few people on Earth. that spend actual time with me, that leave and say, ah, damn, that was a disappointment. It's completely the other way, because to your point, so much of my content has to be more general, has to go in different directions.
That's why 4Ds was so good for me. 4Ds, when I was doing those sessions, when I could really go deep, I mean, that's where the clip from Savannah Banana, giving them the playbook, look what the fuck Savannah Banana came and became. That's why Caleb, before we started, he knows, he was there.
He knows that when he was filming me, 90 % of it has never seen the face of her. When I die and that shit goes out, people will be like, damn, that motherfucker. You were early on a lot of people as well, too.
Something you said to me that has resonated to me over the years, and I think it's one of the reasons, among others, why this podcast has been successful. I think it has to do down to kind of guest selection, backing into something that you told me a very long time ago that's always stuck with me, is you shouldn't give a fuck about the 99%.
You only should care about what the 1 % think about you. Because like you said, the real ones know that you have it. But doing tactics that appease the 99 % will basically annex you out of that 1 % forever.
That's right. I'm glad you remember. I remember where we were, not only that.
So like, yeah. And like, let's deep into that because people need to know I'm a human. Like, I don't love being underrated.
I don't like being misunderstood. I don't like when people think like VFriends is a scam or like, you know, like I don't like those things. I don't like when people try to.
build themselves up by tearing me down because i've got a big platform i don't like it but i don't not like it you know what i mean like the tweet replies will pop up a couple tweet replies they're funny you just kill them with kindness it's fucking funny i don't really kill them with kindness it's you again you know me yeah i'm just genuinely kind like if like if you need to shit on me because you're that small and you need my big to give you a little bump you're not good I agree.
Anyone that's bashing in the comments has a pathetic existence. I don't know about that. I don't know.
They have something wrong internally. Again, that energy is the normal energy. You know this.
I don't view it that way. I'm like, damn. Like, really, in my head, it's like, straight up, Gary V, fuck you.
You fucking suck. You feel bad for them. Literally, I'm like, literally, I'm like, that fucking suck, man.
I couldn't imagine seeing you, like, when I started seeing this going. Yeah. to live like the joy forget about that we know each other even when i see people starting to pop off when i don't know them the joy i have i'm like yeah you know without now you don't want to be bad people and use their platform to fuck people up but like the thought that you winning or someone else winning is taking away from me winning man that's a shitty way to live if you when you live in scarcity when you think the world is not abundant When you are that insecure.
Almost nothing is a zero -sum game. Almost nothing. Correct.
Yeah. I want to tie a bow on just the content machine under the notion that you're just like lightly saying that you want to post a thousand times a day. What is that one thing that you can't outsource?
And then what is that one key hire that's the glue to everything content on your side? I mean, there's a lot of key hires, post -production editors that understand how to take all this content and build it in a manner that allows it to organically win and understand how to post it on LinkedIn. and know how that will win there versus what you do on Shorts.
There are very few people that have millions of followers on every single platform besides me on Earth. There's almost no one that has over a million followers on Snapchat and LinkedIn and YouTube Shorts and YouTube and Facebook and Instagram and Twitter like me. And there's a reason I'm in post -production per platform at scale.
I think there's an epidemic for those actual practitioners that natively know the platforms. I think there's an epidemic of the actual editors on that side. That there's not enough?
There's not enough. I can't tell you how many people are hitting me up, like, give me an editor, give me an editor, give me a creative strategy that I can understand. That's right.
And then, to me, it's the people at the top who did it in their careers. All of us. Me, Sid, Andy K, Raghav, you know, Norea.
Anyone that ascends to a senior leader on my team did it so they know how to manage it. You have to do it. I'm like fairly new on Twitter.
I'm like 10 days in of just being, posting every single day, all day, engaging with stuff. It's like a full -time job, that one above. That's how I built Gary Vee.
The lost story of me is 2007 to 11, Gary Vee on Twitter is how I'm here. And all I did was engage. I didn't even post that much.
I wish I got in earlier there. I'm happy that we got into YouTube because YouTube, I think, actually is the most valuable platform, which guys will get into. They're all valuable.
By the way, Substack could be the most valuable if you're good. Like Beehive can. I'm a Beehive guy.
And you might like Beehive because you have a deal with them or an investment. I love the founder. So no shit.
But that's another thing that I think has made me me. I was an investor in Gowalla, which was a competitor of Foursquare. I told every client in the world to use Foursquare because Gowalla wasn't innovating.
I'd rather be right than co -sign my investments. In this case, I do think Beehive is iterating very, very fast. They are.
And he's a gangster. By the way, they're both going to win. I agree.
By the way, Threads, where are you at? Not really on there. You better fucking wake up.
Are you pushing through or are you natively posting natively, I imagine? Natively. Yeah.
Natively everything. No reconditioning to everywhere. I mean, I'm willing to if it makes sense, but it is what works on this platform.
If the same thing happens to work on Threads and Twitter for three months, then I don't mind doing the same thing. But it's always what will work on this platform, not what makes it easier for me to post. If all these dickfaces took some of the money they spend on jewelry and Lamborghinis and put it into more team and more process, they'd win everywhere.
Yeah, we're aggressively hiring. Just on the editor side, we just hired two more editors just to understand native to the platforms. Thinkers, producers, editors.
When you look at all this, you can just say at... face value, you're a great personal brand. How would you filter like the characteristics of a great personal brand right now?
Because I know that you've seen it. The truth to them at that moment. I think the thing I've done well and others do well when they're doing it well is like, you're just honest to your fucking self.
Like, like I started making garage sale videos at the height of my heat when I was really exploding. Yeah. And like a lot of real like Silicon Valley, Madison Avenue, private equity, Wall Street.
Very, like, elitist people were starting to kind of accept me, and they hated the garage sale stuff. Yeah, they were confused. They're like, why the fuck are you doing this?
You're just cracking into our elite world. We respect you finally after thinking you're an idiot. You're making garage sale video.
I'm like, yeah, motherfucker, it helps people. That was what was real to me. And it's native to what you love.
Yeah, I like garage selling. What do you want from me? Fuck you.
I do have questions on, like, Pickleball and Wiffleball and stuff like that. Yeah, Pickleball. I bought a team for $500 ,000, and they're selling for $20 million now.
It was a good deal. Did not know that was the case. Damn.
Yeah. Bro, I will forever be underrated.
So was it an OG team that started it? Was the league already started or was it a team? It was super early.
No, the league was like, no, it was, it was, they were just starting to sell their teams, which is why I got in for 500K. Can you make me a promise on camera? He was just on last episode.
He's a gangster, Paul Rabel, PLL. Yeah, I love Paul. When he sells teams, let me get a little slither.
You got it. Oh, our little slither. I know you're getting in on that.
I love him. That could be a big four, I think, over time. I hope so.
He's an absolute gangster. I love Paul. Where do you think the kind of the biggest arbitrage is for operators now with kind of this new attention economy?
AI. The operators are about to win everything. In what sense?
Just because they're more resourceful? I don't need to sit and train anymore. Damn, shots fired, boys.
I'm going to keep them because we're going to go to the fucking moon together. But the person that does has won. And if you're, God forbid me, you're the thinker and the doer, it's a wrap.
So I would agree that you're getting extra benefit because you've already built the lead on the personal brand side. Do you still think there's a window for people to... Bro, you're five minutes in.
I was in for like five to seven years and then I stopped, which was the biggest fuck. So bitch, you're five minutes in. You're in five minutes again because once you were gone, you had to reset.
It does really suck. This fucking... No, it doesn't suck, bro.
You're 40 seconds in. You didn't have hair the last time you were doing it. No, the hair transplant.
Oh, that's right. That's right. So like, what are we talking about, bro?
You had a hair transplant yet or no? But you were good enough. I'll just wear a hat.
Bro, in two seconds, you were, you've made some real noise. I'm proud as shit of you. For people out there listening, it's, they always say like consistently good versus occasionally great.
For content, find a way to not quit and not burn out. Because when you get off that wheel. It's out of sight, out of mind.
Yeah, and there's good years and bad years. Last year was a bad year for me. I talked about that a lot.
Like, I was just busy as fuck with fucking VaynerSports, VFriends, VaynerX, VCR, the restaurant group. Like, everything was popping, and I had to be a CEO and COO. And Brian Gary took a back seat in 2025.
And a lot of people took up that oxygen, and that made me happy because that's the merit of the game. But, like, 2027, I'm coming out so guns a -blazing. And we've been working all year for that.
Like, you know, I'm going to eat up a ton of oxygen in 27. How do you juggle all this? I think you are, there's some people that have come on here and they are absolute psychos and they're the focus guy.
I feel like you're a juggler a bit more like how I am. What do you say to those operators out there that this is what happened with me is we have the web series that we have the podcast. I remember when we cleared 10 million in revenue, I'm like amazing doing the podcast.
And then we hit. a pretty bad spot with the business. And I'm like, fuck, I have to stop creating content.
I need to focus on the business. I'm a CEO. And that actually was the biggest mistake.
So what advice do you give to operators out there that kind of want to do both? More hiring. You didn't have enough players on the field.
I'm very good at over hiring to not have that moment.
Make less money. That is what's great about this business is the margin profiles are so big that like right now we could just go on like. We're going to run this business on like an e -com EBITDA on this kind of scale phase to gain market share.
And then we can always kind of scale up or scale back. But that's kind of where my brain is at. You're either investing in your business or you're investing in your toys to try to impress people that don't like you.
I don't do the toys. Some toy. Yeah.
Do you know what I mean? Yeah. Like toys come in all shapes and sizes.
The toys that we all think about are Lamborghinis and watches and houses. But there's other toys, right? You're just taking money to do something.
To do something. My proudest thing is that I don't think I took a salary that even looked like $200 ,000 a year until I was well into my 40s. That's how Wine Library and VaynerMedia got built.
It all went back into the business. I was patient. The shit I say online is real.
I was patient. I was kind. I was good enough.
Yeah. I feel like not enough people wait long enough. I mean, it was the same with me.
I was probably seven or eight years in where I was always like leaders eat last. I think at some time, you know, at some point you have to cross the chasm and start paying yourself. Sure.
Of course you start family, get married. Like there's different things that happen. Little things like you get, you start to get resentful.
Like I was definitely like, wait a minute, maybe I should just like, why is everyone like, oh, wait a minute. You know, like there's definitely things, but I think too many people think the business is there to give you money to do the other things. And I do think it's the reverse.
The longer you hold your breath, the more you get to win the game. Most creators are just duct -taping together a bunch of different tools to run their podcast and their newsletter. Your audience, the analytics, the attention, it's all split.
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Stop renting your audience, start owning it. What about original content? So this VaynerWatt and I saw you just greenlit this limited time author.
I feel like everyone is running away. From kind of broadcast TV, and you're obviously running towards it in some sense. Well, it's not broadcast, right?
Like, yes, I mean, that one is ABC, but, like, it's also going to be Hulu. Like, there is no broadcast TV. It's just, you know, it's...
Everything's streaming, yeah. Yeah, everything's streaming and broadcast, and so, like, if you can get both, like, why not? Yeah, I have a TV production company that no one on Earth knows about called VaynerWatt.
Tell us more. The Watt part is Eric Wattenberg. I met him when I was repped for speaking at CAA, and I just loved him from day one.
I'm like, this guy gets where TV's going. This is 20 years ago. And I was just like, TV should be a marketing tool for business.
It's going to be more like YouTube, not more like TV. And I just kept courting him. And then I made a real hard pitch to have him join me 11 years ago.
And he went with someone else, which I will forever remember. And then that worked, but didn't work as awesome. And then I kept ascending.
And then there was an opportunity for him to come with me. And we started a company with Matt Higgins from RSC Ventures, who's always a partner in a lot of things I do. And we're off to a good start.
We did a Jets. which was the home team. It was on Amazon.
Well, the Jets season did not work out the way we thought it was going to work out. So not as many people watch that as much, but we've got a bunch of shows. We've got a Kevin Bacon history show coming out.
We have a ton of shows coming. Like, everyone listening here in three years is going to be watching Netflix, Hulu, Prime, Network, and they're just going to see the VaynerWatt logo pop up and they're going to be like, this motherfucker. We have a ton of shows hitting next year.
What does a deal like that look like? I mean, you just said right there it's about the flywheel and... Probably it's driving some other initiative, i .e.
licensing or maybe a consumer product company. But what does a deal like that actually look like? Because all I see is just some of the numbers on the podcast side, but I'm not really familiar on the TV and studio side.
Well, you either own it or the distributor pays you for it. They buy it from you outright. Now they own it.
They're paying you as a production company to produce the episodes. You're trying to make some margin on that. You've got talent deals.
You've got back -end deals. Sometimes you fund it, and then the Hulu or Prime distributes it. you have co -production, you work with others.
It's a really fast, it's actually a very deal -making world. As far as you can just skin it in a million different ways? Yeah.
And it just depends on who has the leverage, right? Sometimes the celebrity has the leverage. Kevin Hart and The Rock's deals got better for themselves and their production companies as they got more famous, right?
So that's kind of the deal. Under the notion that that could drive another, it could be an offline initiative, it could be in -store consumer products, where do you just think the future of media and TV is going on, whether it be like the content medium, the content structure, like where do you think it's going?
I think it's going great. Like people want to watch long form content for the rest of time. And whether that's on YouTube or YouTube TV or on Netflix or on, I mean, there's not a lot of people watch cable, but people watch cable.
Like, you know, people watch network. I think long form and short form and mid form. Content, content, content.
Like everybody wants to always say the death of something when it's always the iteration of something. What's a podcast? It's fucking radio, bro.
This is a fucking radio show from 1937. Visually radio. Yes, when you film it.
But like that's the 1950s television when they brought radio shows to television. This is a 1957 television show with Mike Wallace. Makes sense.
History repeats itself over and over. People make decisions. on where things are going based on their financial interests, not on the reality of the marketplace.
And that is where I really shine. I mean, I'm with you as well, too, that if at any point in time I don't believe in a product, I'll actually try and get my equity out and or I'm not going to keep promoting it. I'm with you on that for sure.
Yeah. And to me, it's more like. I Gary Vee is like completely separate from Gary Vaynerchuk.
Nothing I ever say publicly has anything to do with the vested interest I have in my businesses. I need to be historically correct and bring value and nothing else matters. Now, if that works, if I'm like alternative sports are going to like that, I feel comfortable with.
I believe alternative sports leagues is a good idea. I do invest in them, but I'm thrilled to talk about volleyball and softball leagues that I think are great that I have no equity in.
Why do you think those are going to blow up? I mean, you just mentioned $500 ,000 to $20 million. I had no idea.
It could be a 40x multiplier. Why do you think these alternative sports are going to blow up? Because media's changed.
In what context? There used to be 13 channels, and if you had a sports league and the 13 channels didn't want to put you on, you didn't have a sports league. And then there was 36 channels.
And if you had a sports league and none of the 36 channels wanted to put you on, then you didn't have a sports league. And then there was pay -per -view and Dish Network. And there was a thousand channels.
And if nobody wanted to put you on, you didn't have a sports league. Now there's unlimited real estate. Now there's social.
Now a clip from slapping or volleyball or pickleball can be the gateway drug to people tuning in on DAZN or CBS Sports or CBS or Peacock or there's just unlimited inventory. So now it's fucking merit. There's no gatekeeper saying, I like your slam ball or you're unrivaled or you're three on three.
There's unlimited inventory. Now we're on fucking merit. Do you know why I'm proud?
I compete with every creator on Earth every day.
Do you know why it's so much more fun to be a creator that wins than to be an actor that wins? Actors, Hollywood gatekeepers, gave you a chance. They said no to somebody who was better than Brad Pitt.
No gatekeepers. We're on merit shit now. What's the decision -making rubric, though, on that sports side, though?
Like, you're talking about merit. I would argue that, you know, it could just as much be about attention or entertainment versus the actual... Yes, but how do you get it?
Like, is Vince McMahon great because wrestling's great or because he figured out how to make wrestling great to millions? So you're just arbing everything towards just... Is baseball good?
No, and I don't know what my tricks look like. Millions think you're wrong. Is golf entertaining on TV for you?
Not for me, no. Well, AJ Vaynerchuk thinks you're a dick. Yeah.
He loves it. It's all subjective, and everybody has a fucking ego and doesn't understand their opinion doesn't matter. So is the decision -making rubric just all things lead to...
Who can get the most amount of attention, i .e. the most amount of views? And keep it.
And you're just arming. And keep it, right? You said something earlier, virality versus consistency.
Just because pickleball can have a moment, can pickleball be massive is how I think. Or it doesn't need to be massive. When you put 500K in and you can afford it, being a double is good enough.
I've already won on pickleball. But now I'm like, oh, shit, that's going to be wrong. You know, like, you know, it can get bigger than you think.
What are some of those? You're involved in tons of sports. I'd love for you to just rattle off.
What are all the sports teams? Big League Whiffle. Yeah.
So I just want to, I've had a crazy summer. Can you just win a World Series? I won the first World Series this year, the New York Green Apples.
By the way, naming sports teams is the best part. I called them the Green Apples because we're the New York team, the Big Apple, but I called them the Green Apples because of my Jets obsession. Can we get Cole to whip up a little style guy for one of these teams?
Let him be the creative director for one of them. I wish Cole could do all of it. He's the fucking most talented.
creative i know he's definitely gonna clip that um new york the wiffleball league i'm very into there's a lot of great owners too lazary who used to own the bucks blitzer who owns all these teams logan and jordan rose the mother's son combo that run the league that league has a real shot bro and people fuck with wiffleball bro yeah And everybody feels, and these games that you can play but then also watch.
I love when people are like, pickleball's so stupid. I know everyone's playing it, but who would watch it? I'm like, do you know the history of tennis and golf becoming big?
People played it and then they watched it when everyone said they wouldn't watch it. How important do you think it is to have underlying partners or owners that have distribution arbitrage to bring eyes to it? I wish my partners in every league were the Ellisons.
They just put on Paramount and we won. If it's good, again, like... Some of these leagues are not going to work.
The USFL, the World League. Like, there's been a ton of leagues that have failed that did have television. Vince McMahon, one of the best, in my opinion.
XFL, The Rock. You know, like, it's hard. Like, these are high -risk, high -reward opportunities, but I like going slow.
A lot of things I just mentioned, they went big, fast. They had big TV deals from Fox and CBS, the USFL. Like, I know my history of sports leagues.
They went, it's kind of like startups. We talked about it before we went on air. People raise too much money and then lose.
Instead of making money, they raise money and then burn money and lose instead of slowly making money and win. Same with leagues. Pickleball's just now getting like, we just had a great weekend.
Big ratings on CBS, like it's starting, but we're like five, six years into this. It's like, it's still a little pimple. We're going to pop up right here a bunch of videos.
Those were the best fucking videos when the Knicks were winning. Oh, my God. If you just middle of the night going fucking crazy with your hair going fucking nuts, dude.
Dude, I mean, when you're a diehard, like anyone who's listening right now, when you're a diehard and you've sucked forever, I mean, Knicks were bad for 20 years. You know, those Wednesday nights, staying up at 1030 while I'm working, watching us get fucking destroyed by the Clippers were not enjoyable. And you were in Poland for Tyler's wedding too, right?
Yeah. Tyler fucked me up. Tyler Schmidt, you're a bitch.
Fucking took me away from that Knicks -Spurs game, but I love him so much I had to go to Poland for his fucking wedding. We're going to get into that. My wife's in Poland right now, actually.
She's Polish as well, too. Oh, that's awesome. We got the Polish vibe.
You and Ty have got that thing. Me and Ty. And by the way, I'm Belarusian.
That's fucking Poland. Same shit. Same vibe.
I'd be remiss if we didn't talk about live shopping. So many eight, nine, even ten -figure operators have been on here, and not one person, outside a little bit of true classic, is cracking this live shopping. I have no fucking clue what goes on.
I don't know how to arbit. I don't know how you pay the creator and or you do it. Can you just tell us, like, what is it?
The term breaks up into two things. I use the term live shopping to describe the QVC elements on social, right? There's also the way TikTok refers to live shopping, which is both that part, you're in your FYP, and then there's just a guy, sometimes me, saying, buy this, buy that.
And then there's an affiliate version where people are making content and there's an affiliate deal. So they're making a content piece for Gruins or for Magic Spoon. And then if it leads to a sale, they're getting a cut.
So is this just streaming with affiliate layer labeled on? No, that's like the bad version of it. The good version is with TikTok and whatnot and eBay are doing, which is you're watching and it's one little swipe on a screen.
You bought shit. No friction. And how does that go from a frequency and cadence perspective?
I know it works well kind of in the collectible world where people are, like, breaking cards and such. But how does it work? Like, do you have, like...
I mean, the biggest items that are selling besides collectibles are makeup. There's a woman on here. I mean, like, it's...
Bro, it's QVC. Like, I love when people are like, nah. I'm like, what do you mean, nah?
There's fucking billions of dollars being sold on fucking network, on cable television. Who the fuck knows anyone that goes on Home Shopping Network and QVC and buys a little dog? Maybe my mom.
Billions. By the way, I love when people debate me on this one. Do you know what?
In China this year, in China this year, live shopping, not the affiliate shit, live shopping, person on screen is live and selling something and people are watching, talking to each other and buying shit. This year, we'll do $1 trillion in GMV. Gross merchandise value.
One trillion dollars worth of cars. China's advanced. They're selling fucking homes, cars, yachts, watches, trinkets.
How do you think Labubu happened? I know there's whole office buildings where some content creators like live out of these places and they're just churning. There's like hundreds and hundreds of them.
Bro, I wish I was in a point in my career where I could be live 24 -7 selling. That's how fun it is for me. There's a bunch of people that are meant to be content creators who can't sell shit, will never do it.
But this is going to be a huge era of people who are going to make fortunes because they were never good enough to be Alex Earl or Logan Paul, but they're going to be the Alex Earl and Logan Paul of live shopping because they're a salesman. This is one of the, I believe. And or it's the lowest lift type of content as well.
So you literally pop it on. It's just all about authenticity. It could be kind of low production value.
Yeah, it's definitely, but it's going to be high production value too. It's going to be both. It's like the internet.
What's social? There's high and there's low. Bro, once you get obsessed with and, the whole world opens up to you.
Every question you're going to ask me, the actual answer to your question is and. What's your thoughts? We're debating on upping our frequency and adding into our content mix a little bit more lo -fi content, but we think it's going to affect the brand value and our partners and advertisers are paying for the premium positioning.
And we actually hired someone, started doing it, and then we nixed it. I'd love to know what your thoughts are. You nixed it because you thought it was diluting?
Thought it was diluting, yeah. Because we want to be, you know, the Rolex of podcasts and just, it didn't have that premium aesthetic. I mean, I think you're allowed.
Like, LVMH works. Again, and there's a lot of ways to win it. I'm a fan of both.
But no question, all low or all high can work as well. And to your point, if you're trying to be Rolex and Louis Vuitton and LVMH and highbrow, one could argue that lo -fi could create some vulnerabilities. I'm a little bit skewed on that.
For example, LVMH, all these French and Italian fashion houses love to be like we're fancy, so why the fuck are you doing collabs with streetwear brands? They need relevance. They're going to do shit with Kith and Mad Happy and Siegelman Stables and all these brands because they need fucking...
Like, you're going to get to a place where your relevance might be a vulnerability, but you might not care because you're making so much on the premium plane. You'll just decide how you do that. Or you create a whole other channel and another brand that can lo -fi if you want to.
We're debating on doing lo -fi at volume to test concepts that work and then iterating them with the premium visual identity. That's kind of where we need it at. That is like a no -brainer.
I thought you were going to say that was too much work. No, no. I think that's what makes sense.
I will never say that's too much work to anything in the history of life. Work is one of the most significant variables of success and everyone's trying to figure out how it not to be. It's so funny, man.
So many people are starting podcasts and they're all saying, like, how do I do this but only do it for four hours on Friday? And I'm like, guys, good luck. The same way you do four push -ups and ask yourself, why don't you look like an Adonis?
The biggest learning lesson for me is when we started this, I was like, I didn't think this was kind of the means to the end. I thought this was a distribution channel that would feed into that. And now you know it's the thing.
But now it is the thing. This is the product. This is a real fucking business.
And that's the kick I've been on the whole time. The Gary V thing was a thing, but it was also a gateway drug to all the things because I knew I was psycho and I was going to do 13 real businesses, not one. Not because I thought that would make me the most money.
Because I knew that would bring me the most joy. In fact, it is not lost on me that if I went 100 % on any of these things. Oh my God, nuclear.
Yeah. But it's not what you want. No.
Yeah. What about hiring and firing under the notion that you have, you know, you just have 13 companies there. It may or may not even be more.
Obviously, you can't be in 13 places at once. So, A, what are you looking for in these people? Because I would imagine outside of VaynerX, you have like acting CEOs that report to you.
What does that kind of flywheel look like? And what are you looking for in these people? Family.
They're either. Actually family. My brother, Brandon Warnicke, who I've been best friends with for 36 years.
I love him actually like my brother. Sid was an intern. Sid, how long have we been together now?
12? 12. I do recognize that name from a long time ago.
Yeah, you were with Andy and Todd, but Sid was always like really there actually. So VaynerWatt, I just talked about it. I've known Watt for 20 years.
VaynerSports is run by AJ, my actual brother. VFriends, Andy. Uncle Chronic, what's up, baby?
You know, Andy and John Troutman, who both started with me 15 years ago, Trouty worked with me and then was my partner in Empathy Wines. People don't even know about my exits at Rezzy. Flex on them right now.
Flex on both of them right now. Yeah, Rezzy's a massive exit. I knew Ben Leventhal forever.
He was the act of like 10 years friendship and we were co -founders. We invented Rezzy together over dinner one day and we built a massive nine -figure exit to Amex. Empathy Wines, Nate Schroeder and John Troutman both started with me as interns, became my minority co -founders in Empathy Wines.
And in 18 months, we had a meaningful exit to Constellation Brands, one of the biggest three wine companies, family. Trouty's now back and me, Trouty and Andy and Tyler Schmidt are all like all in on VFriends. These are people, literally all three of them I've known for 15 years.
I started with, they started with me when they were children, all out of college, day one out of college. Family. Outside of loyalty, what are those big things for why it works?
Speed. I don't even care about the loyalty. How much is it that they know how you operate?
Everything. That is literally what we're going through. There is nothing else.
That is what we're going through right now. There is nothing else. Because we're hiring a right hand, like a chief of staff, and I'm just like, I know that there's a savage A player out there that will know how my ADD brain works.
When you interview, tell that person the truth.
What about firing? With all these companies, you have 2 ,000 plus employees on just the Vayner. My biggest weakness of my career.
My kryptonite, my scarlet letter, my vulnerability, my missteps have all been on lack of candor when I cared. I'm a lover boy. You work for me for two minutes.
You're family. Train, you've been with me now one year and a couple weeks, right? I like him too much already.
But he got lucky. Because I've given him some candor along the way. Like, Train, Patent is real talk.
Train got me in my 30s, might not be with me right now. But I got better and was able to give him candor, was able to get Raghav and Norea to give him candor. I was even able to give him candor, not through a passive -aggressive way.
I just struggled to give negative feedback because my father was very good at giving negative feedback and doing it very not nicely. And I think... I was naturally not a good feedback person.
Then that made me go even further to the left. And I just couldn't, it took me a while to see that it was my vulnerability. How do you keep this all going, this train going?
What does a day look like for you? Let's go there. It's random as fuck.
But I'll answer that, but I'll give you the real answer. By not being scared to all fall apart. No judgment daily.
When you're running truly this many businesses, I mean, my entire day is being a firefighter. There's just a problem everywhere.
But I don't take it personal, and I don't think it matters. And so I'm detached from myself. Detached from the outcome, and you're just living in the moment, not emotionally to, you know, bad shit's going to happen.
I'm just detached from all of it, bro. It's deeper than that. What is it?
I just don't think my identity has anything to do with my professional career. So what is the professional career about? My favorite thing to do with every ounce of my awakeness day to day.
The sport of business. The sport of business. What were some of those early investments?
That's another big thing is obviously you have the investor side, you have the operator side. I think on the investment side, people don't understand that you were early in a lot of these kind of tech plays. What were those?
I mean, the ones that people know is Facebook and Twitter, Uber. People know famously I passed in the Angel Angel, but I got in pretty quickly after that. Snapchat was good.
Venmo was remarkable. I didn't make as much as I should have because they sold in between the big exit. Liquid Death is going to be a big one.
Mike worked for me the day he resigned, started Liquid Death. There's so, so many. Mac Rachel just had a big exit.
That was a nice win. I mean, I have a very significant, successful IRR investment career part of my life, to your point, that no one even thinks about these days anymore because I've become known.
And a lot of what's being consumed is more of the stuff. By the way, I'm proud of the mindset and perspective content I make. I think it's the thing most people need.
I love going into tactics and getting real businessman here with you, but I think most people can achieve a lot more if they stop being insecure. So you think the mindset comes first before everything else, obviously. I think it's what's sustainable.
I know a lot of people build real companies through insecurity, but they crashed. You know, you've been around now. You know what's been sustainable and what's not.
You know what steak is versus sizzle now. I do. What's that big common theme across all of those companies?
I have my thoughts. I want to hear your thoughts on the people that have won and the people that haven't. There's a mix, bro.
I think the one common thing was they knew themselves well and they were willing to die for it. You know? I think self -awareness is a big one.
Ev Williams is one of my favorite entrepreneurs. He did Blogger and sold it to Google when blogging was the game, even before I popped off, before even Wine Library TV. Then he did Odeo podcast and got killed by an apple.
And then he came, like he deserves a lot of credit for Twitter that Jack Dorsey gets. Do you know who Ev Williams is? Ev's a dog.
He's like the secondary guy at Twitter. Everybody talks about Dorsey. Yeah, but I think he was the first.
How about that? And Jack's a genius and came up with the idea. But I was there in those first three, four years.
He was, he was. He was more 1A idea, Dorsey. Ev really did a lot of things that really made that company real.
Jack's insane. I think Jack has more superpowers, but at bare minimum, they co -deserve it. We're going to pop up a podcast with Jack Dorsey talking about the future of work and the one to three people you need to build an individual empire.
It's called Long Strange Trip or something. It's so fucking good. He is brilliant.
He's brilliant. Yeah. It's something that it's ironic because we got involved with my first company and now we're talking about kind of the second and third company.
I invest now in companies. Would you invest in a first -time founder? You would.
Sure. I made a lot of money investing in first -time founders. You don't think that there's just...
Oh, it's much more fun to invest in a second -time or third -time founder who's actually won. Do you see a direct... Not the fake winners.
Yeah. All these fuckers that say three -time exiting founder in their Instagram, and here's how the exits happened. One, the company was bought for a penny on the dollar.
One was an AccuHire. And one was like an M &A where you owned 1%. Like, you know what I mean?
Like, no, if you can invest in someone who's done it, that's fun. That's all I'm looking at now. I get it.
I get it. I also love those. But if some 23 -year -old comes and blows my mind that she gets it.
I'm going to roll that dice. What does the day look like? You didn't tell us.
Oh, we might have to pop up like your Google calendar and just blurt out something. Because I know you're on that 15 minute game, baby. Yeah, I'm on that 15 minute game.
A lot of 15 minute meetings, checking in. I mean, it's all over the place. It's where my moments are.
It's like, it's whack -a -mole. It's where I'm at right now. Like VCR group, my restaurant group that we haven't talked about yet.
David Rodolitz, Chef Capon, Chef Connor. We're hot. Flyfish hits.
Flyfish is a monster. Capon's Chop House is our Hillstone, our Ruth Chris. It could be huge.
Capon's Burgers is our elevated fucking Shake Shack. That could be a billion dollar company by itself. So I'm like in and out with them, right?
VaynerWatt's getting hot. Fucking VaynerSports is ripping. We're like crushing.
We just had $200 million deals in baseball. McGonigal and Chase Burns. We just had the seventh pick in the draft.
We have six kids going in this NFL draft that are going to be in the top 50. Like, we could have the number one pick. We have CJ Carr out of Notre Dame.
Like, that's buzzing. Like, fuck it. And Vayner's, I mean, Vayner's killing everything.
Like, I could literally build a crazy -ass marketing company, and then I just told you, like, Gary Vee's about to really come out. And this is without talking about the company that I'm most paying attention to. What's that?
Vee Friends. Tell us about that. What's the macro vision?
That I'm Walt Disney. How long do you think that's going to take? 20.
What's the misconception about VFriends? That it was an NFT fad. It's a hard space.
I still wholeheartedly think the underlying technology is brilliant. And I think the applications, you know. It's internet 2000 all over again.
So why do you think it hit? And now it's obviously it took a dip. It's greed.
People just scammed. People did a lot of bullshit. fucked up the brand.
Just like internet. Pets .com. I mean, this is deja vu.
I was there. I had winelibrary .com in 97 when 2000 April happened and newspaper articles all over the country wrote that internet was a fad. You kids don't know because you're too young.
He has an account. We're going to pop it up. It's called V Receipts.
And you have been... Crazy early, and we'll pop up some crazy psycho videos. And every time I put up a V receipt, there's comments saying, what about NFTs?
And they don't realize that literally this month, tens of millions of dollars of NFTs have been bought because digital collectibles are going to happen. The underlining tech of it being a... Backed by the blockchain.
The blockchain is insanely important. Now, whether Bitcoin or VFriends or CryptoPunks or Bored Apes or Solana win or not, that's execution. So is the additive layer here...
But that's like saying... You're pushing harder into the physical collectibles to... I was always fidgetal.
When I launched Series 2 in 2022, you bought the NFT and got a whole box of trading cards. Those trading cards are ripping. When you bought my book, 12 and a half, you got book games, NFTs.
Those book game NFTs are worth more than what people paid for books right now. Almost most of the people that bought it don't even know that because everyone walked away when NFTs got faded. I'm going to say something on the record and off the record, and I'm not going to say the number, but I'm not going to lie.
I was surprised. Obviously I'm close with Tyler. It's like a real business.
What's going on? I mean, he told me that. Yeah.
It's a real business. And I'm going to build such a fucking monster, bro. I'm going to Stan Lee, Vince McMahon, Dana White, Jim Henson, Walt Disney, this thing.
And I believe in my heart and soul that I'm going to make your future children. wear V -Friends character pajamas, and you're going to be like this motherfucker. I feel like of all the things, that's the biggest chip on your shoulder, and that's the one that you're going to...
I don't have a chip for the V -back. I'm empathetic to why people think NFTs were... There was a lot of bad behavior, but not for me.
Like, I feel unbelievable, and it's not a chip. It's just the biggest thing I can build. Do you understand Pokemon's worth $100 billion?
Maybe more now? I'm building a collectible and storytelling IP. That's who I am.
What needs to happen for that to go to the next level?
For the audio listeners, he's tapping to his watch right now. Which I don't have. It's just my wrist.
I don't wear a watch. But I am so excited. I enjoy it.
Bro, the other thing is, VFriends is Gary V. Gratitude Gorilla teaches people how to have more gratitude. You know?
That matters, man. Do you understand every person listening? If they took 10 % envy and jealousy out of their body, and added 10 % gratitude, their life would be dramatically better.
Do you know how excited I am to write? I have six kids' books coming out next year. I'm going to make it a monster.
Do you know how fun it is for a six -year -old to learn about accountability? Like, I'm being noble. Like, this is my most noble venture.
Jim Henson. Save the world. But it's also my most selfish.
I'm going to build a billion -dollar company, and I'm going to buy the Jets and win a Super Bowl and then go into the ground and feeling nice and fine. I would argue, too, from a quote -unquote author or creator perspective, you have the most amount of attention or distribution arbitrage of any of your competitors in the quote -unquote kids' IP space as well, too.
That's a huge advantage. Maybe, but VeeFriends will fail if it's about Gary Vee. And VeeFriends will win because Gary Vaynerchuk's good enough.
But when you say time, you're talking about basically incremental distribution is going to happen. You do the books, and then it gets into more people's hands. I mean, my comic books...
If people went to eBay right now and said completed items and saw what my comics sell for, I already have meaningful Hollywood distribution asking to option it for film, television, and animation already. And I'm like three years away from even considering it. And this goes back to the flywheel too.
Obviously you have all these other companies that could support it. Like you could do original IP with VaynerMod. I could do anything.
He says time, guys. Guys, quick break. We put together a free PDF outlining...
All of the learnings from Gary in this interview, link down below in the description. Enjoy the rest of the episode. I want to double click on VaynerSports.
Please. Biggest learning lesson out of that. I've dealt with CA, William Morris, UTA range.
I've dealt with all of them. I was very excited when you and your brother came in because I just think that you guys fundamentally think different than they do. What's the biggest learning lesson, I guess, from a macro perspective of that business?
not much. It's kind of going the way I thought. If you're asking for me, like I knew I wasn't going to be 1A.
So I knew AJ would be a little slower than me on top line revenue because I know who I am on that. B, I knew it would be as noble as anyone could ever do because my brother's the most noble dude ever. So we were excited that we were going to break the game by being better dudes.
We knew we were going to have to eat shit for five years. And we did. We couldn't get, I mean, I was like, I actually got a little surprised.
I thought I'd be able to get some people just on fucking Gary V. They were scared. They're like, who have you repped before?
And then I learned, I was like, people are scared. You start with the offensive lineman and get him like a $15 ,000 random deal. You start, I remember in the beginning.
Yeah, Matt Paradis. I mean, we crush now. I mean, Kirk Cousins has made more money playing football than Tom Brady.
Like, we are killing it. Just named starting QB, too. You know, we are killing it out there.
We're doing great. I'm very proud. And some of the biggest sports agencies, the ones you named privately, have said to me how impressed they are.
Because to go from zero, just me and AJ are like, let's do it, to now being one of the largest independent sports representation agencies in the world is humbling. We did it in a short period of time, less than 10 years. An interesting question for you would be, given that the operator is probably listening, if they want to engage with an athlete, and we could talk about someone that's on the high end versus someone that's kind of new into the league.
How do you best recommend working with these people? Don't get ripped off.
The best way to get ripped off is to do a deal with your favorite athlete. Because you're really doing the deal just to like meet them or have drinks. Where is the arb on the marketing deliverables?
More outcome, more output of content. They're going to try to beat you down. Only three posts for three months, you know, and you need to beat them up.
Whitelisting or no? Or is it just... Hell yeah.
Get whitelisting. Get one piece of content for a big athlete, and you can run ads against it forever? Hell yeah.
Who's been the most surprising person you have signed?
Off the field, not on the field, from an intelligence perspective and a deal perspective. I'm curious. Oh, you mean like a brand deal we've done?
Yeah, like what's one that... I don't think anything's been surprising. I knew they were going to be small deals, and then I knew they'd be big deals.
I wouldn't say there's... I don't know if there's a surprising... I don't want to bullshit you.
There's nothing been surprising. I mean, the day we started, I'm like, oh. We're going to do deals with little brands at first and big brands because I have some relationship.
Like it's been very, VaynerSports has probably been the most like out of every company potentially. More just, I just knew, don't forget me and AJ had just built VaynerMedia. Like it was like, talk about right down the fairway.
It's gone exactly like I thought. Shitty for the first five years -ish. And then it tips over.
He's Sauce Gardner, Aiden Hutchinson, Kirk Cousins, Boba Shett. You know, it just, Ian Machado, Gary, like you just start winning. What does the future look like with that?
Bigger athletes? Yeah. I mean, that's one company out of all of our empire that I could see us M &Aing.
Or JVing. Or JVing. Yeah.
Yeah. Out of all of them. Under the notion that someone is buying your existing roster and probably...
Yeah, and there just could be some strategic stuff, you know? You know, we'll see. Or we go the other way and triple down on it.
Let's go into VCR group. Biggest learning lesson there. Because this is a completely new.
That David Rodolitz was even better of an operator than I thought. What's his background? He was in the business.
You know, he ran MPO and he was in nightclub. He was a friend and he's such a nice guy. It's kind of like me a little bit.
Like he's so nice and such a good dude that probably subconsciously I didn't realize how much of a killer he was. Even though I invested in his last two restaurant groups and got to see it, he's been even better.
What is that DNA underneath there? We've had Grutman on there and Terzian on there. Grutman's amazing.
Grutman's on a planet of his own. Noah from Tao Group, those guys. David's a little less nightlife than those guys and a little more restaurant.
And he's such a good family. I mean, honestly, I say this a lot privately. I'm glad I get to give them these flowers.
Like, if my children married a spouse... That was like David Rodolitz. It'd be the best day of my life.
He's that quality of a human. And then professionally... What's his superpower?
Tenacity. And it's hard to see even when you know him until... You know, you never know what you have until you get to the foxhole.
Just works. But he works while still being able to be a good dad and still get his tennis in because he's a psycho. He's just got it down.
He's a good leader. Chef Capon is just a celebrity. He's a maniac.
He's hysterical. Great vibes. We're going to pop him up.
Great vibes. But a great chef and cares so fucking deeply. And then our secret weapon, Chef Connor, real fucking operator, can make any kitchen right.
I can make up a fucking Sloppy Joe fucking express in outer space idea and he can operate it and make the Sloppy Joe delicious. We just have a great team. Tony, we're going to build a very big restaurant group.
For the people out there that are listening and that are doing, let's just say they're starting to kind of quote unquote build their empire and they want to kind of dip their hands in these certain things. And I'm doing it on a way smaller level from an investment perspective. And I was too when I was 40, by the way.
Just 10 years ago, it's not like you're, I mean, don't forget like how at zero I was starting at 34. People sometimes when they want to fade me be like, don't listen to Gary. He inherited a winery.
Like they don't even know the fuck they're talking about. I built my dad's business for him and at 34 had to start over. We're going to pop you up in Buddy Media office.
All my buddies were working for Buddy Media when you started, by the way, too. That's so cool. I was sleeping on a couch on Bleeker Street, broke as like a 21 -year -old.
It was great. Most of our, Mike Boyd, our music guy, slept in the office. We were broke, all of us.
Me, AJ, Mike Boyd, David Zhang, you know, Matt Sinema, Marcus Krasastik, Kevin Statz, you know, Sam Taggart. This was me and AJ's friends getting a space for free for two years because we had so little money.
Let's get strategic here because I'm, uh, I'm obviously back a decade on you, but I'm starting to do it, and I'm basically bartering equity in companies. What does this look like when you have distribution, trust, and attention at scale, and you want to dive into these other businesses?
Is it like, are you doing - Step one. Step one, yeah. Do not compromise this audience, bro.
Bro, I'm telling you right now, the best thing I've ever done in my career is that Gary Vee and Gary Vaynerchuk are different.
I will never use my attention to - push something for my economic wants if it is not incredibly clear what's going on, period, end of story. And those startups I get equity in have to do a lot of work before they earn me even contemplating spitting it to my audience.
Yeah, I'll pop up that tweet. My first tweet that went off a week ago was just, this all comes down to one thing and one thing only, and it's trust. And for us talking to partners, you would be fucking mind blown, bro.
Where it's like, someone's going to cut me a check, but then I'm asking them not only questions about their business, but then like, what is the offer to my ICP? Does it deliver value? And or how is it positioned in the marketplace versus the other?
VaynerMedia, they doesn't take on clients that offer us millions of dollars because they think their product won't sell. Integrity matters, man. If you're trying to build an empire.
If you're just trying to make a couple bucks, 5 million, 10 million, 20 million. You can do anything you want. You can be a piece of shit.
But if you're trying to go for it. I think just all the money goes to that 1 % that builds the trust and won't break it for anything. Yep.
So under the notion that you do like what something looks like for someone that's just starting to cross that chasm, is it equity deals? Is it investing deals? Is it they can utilize your likeness?
Is it getting your strategic brain? Yep. Any and all of those things and you just dice it up.
I'm writing a new book called The Individual Empire that will come out next year. My thesis is that the personalities that are exploding on the internet right now are the actual next Fortune 500 companies if they're good enough to build around themselves true enterprise value. I'm doing it.
Bartlett, Hermosi, Cody Sanchez, Earl, Beast, right? Alex Cooper, Logan Paul, Jake Paul, and everybody else. And all of them that are coming up.
That's what's happening. When is Apple coming out? Probably March or April.
So you're saying the big thing... So the big thing there is Crush It told the world in 2009, I wrote it in 2008, that you could make $100 ,000 a year on the internet, and everyone laughed at me. This is ultimately the big boy version of Crush It, that the people that are making a million dollars a year right now can actually make a billion dollars a year.
If they quadruple down on their personal brand being the spine and then them building out the capabilities in a team around themselves and not compromising exactly what we just talked about. I think a big piece of that when you kind of dissect it is it's happened with Iconic and it's happening with this even to a bigger level is the ability to build a company with low OPEX if you can utilize AI.
So you could start companies right now for literally little to nothing. And then being smart enough. to get OpEx way up because you need people, otherwise it won't happen.
I'm on chapter two right now where the money is starting to come in, where we're like, okay, let's go on fucking savage offense. Higher. We started, I mean, it was literally just me and Jake.
Dude, it was just me and him for the first, what, nine months or a year? And then we brought on an editor and we had like a social media poster and a graphic designer, but now we're going, we're upping that velocity on the content side. What are those other big mistakes?
Because I think there's a lot of people out here, like I can think about so many operators that have been on, Greg Lav from Bloom, Dom from Raw, that are like, they're going all in on their personal brand. And I see them kind of extending into all of these different net new verticals. Outside of trust, what is that other kind of big red flag or mistake you see people make?
I can speak to my mistake. I'm very good at getting to 85 % there and then like not putting the final nail in the coffin. In what sense?
A lot of times when I do things ahead of everyone, like... Podcast, YouTube, like I don't like put the final nail in the coffin and like go to like the tippy top. It's like 90 % across the board.
And I think I can do 100 % across the board. So I'm trying to dissect and figure out like, how do I do that? I can speak for myself.
You know, when you're trying to win on every terrain. And that's maybe what comes along with trying to be the most followed person on every platform. have 13 businesses that are actually real.
Like I am truly stretched into a level that is insane and it's working. And so it's obvious to me where, but I feel like I've got another gear and I haven't, you're catching, you can see I'm very clear. This one's still a little blurry, but I'm glad to say it out loud because I hope it helps someone.
What about from a tactics perspective? If someone wants to get started, how do they go from zero to one? Is it just put out more content?
Self -awareness. Yes, but what and where and how? Are you a writer?
Beehive, Substack, LinkedIn, Twitter. Are you fucking gorgeous and charismatic? You better make video.
You know, are you a great listener and great interviewer? Get on this podcast shit. Like, self -awareness matters.
Do you think everyone could be a content creator? Yeah, but I think everyone can't be a Hall of Fame content creator. Can everyone play basketball?
I have four times this week. Am I LeBron fucking James? No.
Am I better at basketball, literally, than I would be if I never played? Yes, I watched John Morgenstern play basketball. He sucks.
Because he does quant math things for us. We're going to pop him up and embarrass the fuck out of him. Eat it, Jamo.
I have a zillion different questions under the notion that my 15 -minute meetings with Gary are fucking amazing. We're just going to have a bunch of 15 -minute meetings right now. I'm just going to fire away a zillion different questions here for you.
I'm going to start with little quotes from some of your team. I spoke to some people. So let's start with Dio.
He's been with them for 12 years. He said he's not driven by money. I watched him make hard calls that made zero fiscal sense because they were the right thing.
He sees people for what they are before he see it in themselves. And he's opened doors for more people than anyone I know. Tyler, 13 years, started with 200 employees, went to 2 ,500.
The best mentor anyone could ever have. Business strategy, confidence, reading people and trends, leading teams. He always gives you what you need to hear.
You never leave a conversation with Gary believing less. in yourself.
How's that make you feel, man? Really good. You know this.
I'm a rare individual and there's many others. I'm not like alone, but I'm one of those people that is adored more when you actually know me. And you know this, a lot of people are adored in public right now and they're a real zero in real life.
I say you're underrated all the time. And I think that people, I think a big thing is people don't understand that you are. who you are in real life as you are on the internet.
I think I'm better. Yeah, yeah. You know, again, you know what I'm talking about.
The D .O. quote is so uncomfortably real. I give a fuck about people.
For real, for real.
Do you think that's the secret that people have stayed with you that long? Of course. Why the fuck would 150 people who've been with me 10 plus years be with me if I wasn't everything and more than I am publicly?
Why on earth would they be here? Just giving a fuck. And these are real players that you know.
It's not like they're a fucking C - and have like, Sid can fucking do 900 things. The fuck's he doing here?
And I feel an incredible responsibility to start building, you know, and they suffer with my patience. They have their wants and needs financially, emotionally, but it teaches them and they become better men and women. And we're going to win so big, it's not even going to be funny.
I think there's also something to be said that I know a lot of people, i .e. Caleb Ralston, that's a good friend that not only has left and started something big, but you have actively encouraged them to do so and have been a cheerleader for them and helped them any way that you can. And I think that's not a lot of people.
I don't want to keep people. I want to build people. And if they happen to play with me as a teammate forever, great.
And if they happen to go on and do the Babin and D -Rock and Caleb thing, great. And what they know is who I am. That's a big learning lesson that I learned is just like, you know, if it's not right for that person and like setting them free is a huge fucking thing.
And then being for them once they leave. Not only do I have complete freedom of setting people free, I try to springboard them into their next thing and comma, take my biggest asset, which is my time to be there along the way as they build their thing. I'm going to airdrop you the videos that they all sent to me after for whenever you're not at a 10 energy level.
When you're at a 9, it'll make you feel real good. They said a lot more than that. Okay, random.
Tons of questions I'm going to ask for you. Best business you passed on? Airbnb.
What round? I got an email from Joe at airbreadandbreakfast .com saying, me and my co -founders think you're the coolest. We'd love for you to invest.
Ah, that one hurts. Most underrated business advice. Give more than you take.
And nice guys finish first. Everyone's confused. Everyone.
It's what drives me to do everything I'm doing right now. I must pound into the fucking skull of the youth that do not compromise your morals and who you are for the bag or the girl or the clout.
It compounds over time too. You just have to wait. You just have to wait.
One meeting you'd delete off your calendar forever. That I could? Yeah.
Man, I'm such an idiot. I'm such a yes man. I've got to start saying, I mean, a million of them.
I'm an idiot. I take so many random meetings just out of kindness, and I love it, and it goes contradiction to what I'm saying, but I've got to refine my time because I've got a lot to do, and so I just do a lot of weird random meetings. On the contrary, I've had this argument with Jeff and it's played out a million times where this random serendipitous 15 minute fucking coffee plays off and goes fucking crazy.
That's why it's all so tough. But like, you know what will happen? At 40, I was fully there.
At 50, I'm like, you know, and at 90, I'm going to be like, no. For sure. $20 million cash post -tax or your audience?
I mean, that's the stupidest question. What's the number, bro? How much to give up all my audience?
Yeah. Can I rebuild it with a different face? I mean, take that into account as well, too, because I know you're radically confident.
As, like, I have to rip my face off like Travolta and that movie and be a different person and start from zero? No, you got to be Mr. Flawless.
Greg, you and I can't get shut down. I'm gone. Just all of your accounts get wiped down to zero.
But you're still you. You're still you. Oh, then I'll take a dollar.
There you go. I can build it. I can build it back in a second.
Biggest check you've ever written?
Five?
Platform you'd bet on for the next five years. As long as Zucks is playing, he's the guy. Why?
He's adaptable.
Platform that's overrated. I love platforms. And they're nuanced.
I need an answer from you because I know you have a special place in your heart for each one.
Platform that I think is overrated.
Fuck, even the ones that I like to take shots at are starting to reprice. Are we talking about marketing energy? Either.
If I talk about marketing energy, by far the worst platform in the world is television commercials. I'm actually getting weirdly into print. I'm bullish print.
Because it's underpriced? Yeah. But it's still overpriced.
I want to start net new magazines that are underpriced for the consumer and the advertiser. I'm bullish analog.
One card you'd never sell? Trading card? Yep.
Probably my Jackie Robinson PSA 9. I just think, Jack, I don't think people understand how important that human being was to society. We're so far away from where America, even though we have unlimited racial issues, that 48 -leaf Jackie just means a lot to me.
What's the number on that? How much is that looking at? 50?
100? No, it's probably a million -dollar card now. Light flex there, Gus.
Screen time. Honest number. Mine?
Yeah. As much as humanly possible.
First app you look at in the morning. Text. You know, I have all these companies and different time zones.
Like, I gotta see if there's any fires. iMessage. What are you insecure about?
Being a good dad. Like, I feel good. Like, it's not what you think it is on paper, but it's fucking, like, fuck, what the fuck else, right?
So you just want to be as good as possible.
What does your mom teach you that still runs your life? All of it. She's, I'm nothing.
You know how much I talk about this. Do you know how easy it is for me to sit here, get those Dio and Tyler accolades, and know that's my mom? Like, do you know how fun it is when you have no belief in your own self that you know you're the proxy of someone greater than you?
When you've got that level of humility, everything's easy.
Shut up, mom or baby truck. And your dad. Your dad's fucking hysterical.
Dude, I love my dad. And my dad, honestly, real talk, I do believe my dad is underrated even by me. My dad is the one who sucked out all of my potential salesmanship bullshit.
He scared the fuck out of me at 1450 to embellish anything. and I still embellish because it's naturally on me, but he fucking scared me about lying. He's such an honorable man.
I do think that the people that think like, ah, is this guy real? I could have maybe become that without, because my mom was more like feelings. My mom is more of like a gab, like juice up the story to make it.
My dad is fucking like. I'll never forget it. I sold like 180 bottles of wine.
And I told him like over a couple hours, my dad was gone and we needed to sell. I crushed, right? I was like 16.
He's like, how many, what did you, I'm like, dad, I crushed. I sold, you know, like 200 bottles of wine. The next day, because he went back to the receipts the next day, he fucking reamed me.
Everybody else in the store sold eight bottles. I sold 180. I said I sold 200 bottles and he was mad at me.
So I. My dad, like, one could argue that that singular thing about my dad, about honor, be good, like, not that my mom is that too, but she's a juicy embellisher. And like, that's what gets you down the path of being bullshit.
So it took both of them, of course. And by the way, New Jersey, Martin Luther King Elementary School, being a bad student, being born in the Soviet Union, Grandma Esther, Uncle Misha, like all everything, your environment, the Jets. Immigrant energy, baby.
And being a fan of a shitty team. The Jets might be my secret weapon. When you're comfortable and enjoying that much losing, who can beat you?
Knicks fucked it all up for you, man. They kind of did. What do you do to relax?
I'm always relaxed. Real talk. My perspective on life.
I'm really curious. So I do like these monthly meetings with my wife and she thinks I have a problem where I always talk about business and it always just circles back to business. Yeah, it's the best.
Do you ever not talk about business? Yeah. I talk about the Jets.
And I do a lot of family talk. I love talking about my family being with my family. But no, business is my great love.
Why wouldn't I talk about it? I'm with you. Biggest myth about you?
I think people... do think I'm stressed and I'm hustle and I'm hardcore. I don't think people have any, I think people are completely confused about who I am because of my energy and public domain.
I'm with you too. People think that because you're always working, obviously you love business. I love business too.
And they think that they almost like feel bad because we're always working in a rush. Meanwhile, like that's pure bliss for me. I would tell you that people rightfully, I would, if I consumed me from afar and didn't really know, really consume me like that, just surface level, like most of the world.
I think they'd be shocked to realize how detached I am from my professional success and who Gary Vee is. I could give a fuck. Give a fuck.
I feel like it's both, though. You don't give a fuck, but you give a fuck. I give a fuck about what Dio and Tyler and you think because you know me.
It's bars right there. You've been in the game a long time. Since 2006, who blew up that people don't know that you talk too early?
I feel like you are the little whisperer. I mean, I was really, like, really there for Logan and Jake, you know? Alex Cooper sent DRock DMs to join Team Gary.
Wow. I mean, a lot of people. I mean, like, Stephen Bartlett.
I mean, I don't think it's fair to put it on blast, but, like, he said something to me that, like, I'll forever be grateful he said it over dinner about a couple months ago. He was just very kind. All of them.
A lot of people. Like, listen, but not because I'm special. My timing was fortunate.
I was me, but a lot of the people that have won, if they were there then, they would have been that person for me, right? Like, Zay Frank mattered for me on YouTube. You know what I mean?
Like, Michael Arrington from TechCrunch mattered to me. Kevin Rose from Dignation mattered to me. Like, you know, like, people mattered to me, you know, but I really did it.
Like, I really, that's one thing I went 11 out of 10 on. Social, content, the opportunities now. We can all do it.
It's not just about a job. College, the world's changing. Go.
You can do this. I'd love for you to just drop in like Dio and Tyler. I mean, they're at the forefront of this reaching out to people that are on like the precipice of blowing up the kind of state.
Really, Dio, for sure, yeah. What does that look like? And how has that strategy played out over years?
Yeah, I mean, everyone, a lot of people know this. Like I reach out to, like I love rooting for people. And if I'm in my fucking feed and I see a kid and I'm like, hmm, they might have something, like it's fun for me to DM them and be like, yo, keep going.
And when they're like, now, back in the day, like even 10 years ago, they'd be like, thanks, man. Now it's like, holy shit, because it's cooler because I'm bigger. And then it's like, yo, Dio, go meet this person and literally back to like giving, not taking, like find out what you can do for them.
That's the punchline. My great goal in life is to give as much as possible and hopefully never have to ask for anything in return.
The latter's where it's at, and you don't have to ask for anything. When you're good enough to get all your own food, you don't need someone else's.
Bars. Sports cards or the S &P? 10 -year period, from now on the next 10 years.
From this second, though, it could be close, because now sports cards are maturing. From when I was yelling about it in 2019, all of you, everyone who didn't is like, fuck, I wish I did. And honestly, I think sports cards are going to be massive.
But I think it depends. Because cards, collectibles are cyclical. Overall collectibles are here now.
And it's going to get bigger. But within it, cards, comics, coins, pins, toys, old music, there'll be cycles. And so, like, if we clip this in 2036, in that moment, cards could be on a down cycle and not an up cycle.
Because it's more like art and watches. They turn more. S &P is like...
You know, the S &P is basically... Tied in directly to our weapons. Who's going to fuck with America?
We'll blow you up. And we print cash in perpetuity. It's not grounded in anything.
How can we lose? Who do you think is the best marketer alive? Can't say you.
Then I can't answer.
We're going to do some shout outs at the end, but specifically marketer. I mean, Donald Trump's definitely way up there. You know, and that's politics and, you know, I hate that shit.
But by the way, Mondani, AOC, both sides, like the politicians, these politicians that are tricking people that they're going to actually help them, that's great marketing. They're all the same. They tell you to hate someone and be scared of someone and that they're going to save you.
Motherfuckers, if you think a politician's going to save you, you are the ultimate bitch in the world. Those are good marketers. Dana White, very good.
like, built a whole fucking league by making Ronda Rousey, you know, Vince McMahon. Vince McMahon might be the answer. Wild documentary.
Ever see that? Of course. The second it came out.
Insane. Vince McMahon may have, I mean, he took a local touring circus that no one gave a shit about. They did.
They had their fans. But he fucking turned it into a world, like, he's way up there. Rabel told me that Triple H is as impressive as McMahon.
Oh, he is. Paul's insane. And Nick Khan is part of that.
They're a group. They're a crew. Favorite V Friends character and why?
It ebbs and flows. Anyone who has more than two children knows that there's some ebb and flow when, you know, all 286 characters are my children. But lately, I'm very hot on Tenacious Termite.
I really think the answer to a lot of people's questions on this that are listening or watching is they lack tenacity. They're scared. Savage mode, guys.
Just go fucking savage mode. Yeah, like, because no one cares. Like, when you fuck up, what?
Like, and when you win, what? Like, when you realize no one cares and that's a good thing, your life gets good. The most dangerous people are the young people that truly do believe that.
I thought I believed that in my late 20s, early 30s. But you didn't. It took me until now where I really don't give a fuck.
I don't give a fuck, bro. Bro, I really knew you did. You really did when I met you.
Yeah. But you were on your way, which is why I was excited.
If you could own any company in the world, which would it be and why?
Disney. Because I just like it. I just like the intellectual.
If I could sit at the top of fucking Mickey Mouse and fucking Yoda and fucking Spider -Man, Marvel, Lucas, Disney, I would fucking cook. Bob Iger in his M &A deals of Lucas and Marvel. will forever be underrated.
They are literally, especially where AI is going, where the world's going, they will forever be some of the greatest M &A deals. Right there with Zucks with Instagram and WhatsApp. The greatest M &A deals of all time.
Super underpriced if you think about the world we're going into. Four to five billion, six billion for Marvel. This little punk is going to build V -Friends to those kind of numbers.
That's fucking Disney and Star Wars. I think people would be... Absolutely fucking mind blown.
I work with Authentic Brands Group and I have a very intimate understanding of that business. Do you know how much Care Bears does a year in licensing? No, but I know Jamie bought it.
Over $500 million. Care Bears. Makes sense.
Would you think that they're fucking relevant? I know. Trust me.
You think I'm building VFriends for fun? But I have a bigger purpose. I need both.
I need the Gary Vaynerchuk part. I'm going to build VFriends. But I need the Gary V part.
I need... the world to fall in love with Gratitude Gorilla more than Pikachu or Care Bear. Well, Care Bear's actually good.
It's very similar, actually. Care Bear has a lot of B -friends, like, tie -in. But, like, I want to make people...
Do you know why Spider -Man's so big? I don't. He's a normal, flawed kid.
Peter Parker's a normal, flawed kid. Relatability. Relatability matters.
Fucking Superman's fucking... Who the fuck can relate to Superman? Even though he's massive, which is the other play.
The complete opposite. Heroism. That's right.
Your unfair advantage in one word.
Detachment. Start over with nothing tomorrow. What's the first move?
Content. How do you know when it's time to quit something? Intuition.
Amazing. We're going to end with a little message from your brother. He said you're one of the best people he knows.
Passionate, kind, a visionary who makes everyone around him better. That's what everyone says, and I completely agree. And like I said before, exactly the same off camera as on.
Give me one sentence on him to describe your brother. He's the best guy. The fucking, he's a more, he's a better guy than I am.
I have a warmer element, but he's a better man than I am. He's that good. Shout out Uncle AJ.
All right. Last four questions I ask everybody. Favorite book or podcast right now and why?
Can't answer. Not consuming. Either.
I'm just not. It's been that way forever. Truly.
It's really been that way because I consume the net. Or the gross, you know? It's just the way...
You're a scroller, though. You're a scroller. I know a lot of shit.
Big time scroller. Think about this one. An entrepreneur or brand that you want to give flowers to and why?
There's a lot. An entrepreneur or brand. I'll try to come up with a really good one.
Because I've talked about Zucks and how I feel about him. I think he's wildly underrated. Just talked about Dana and that brand.
I think Ari Emanuel. I love what he's doing right now. He's won.
Obviously made a lot of money, WME, Endeavor, WWE, UFC. This thing he's doing, which is rolling up analog businesses, tennis tournament, he's got it. He's just going all in on love.
And he's right. The AI thing's going to push us to the real world. A creator you want to give flowers to and why?
There's a lot. I'm going to go left field. Oprah.
Because in a weird way, she kind of was the preview in the old medium to a lot of what can work in the new medium. She connected with that audience and went emotional in a different way that wasn't, it was rah -rah and real. I've got a lot of Oprah in me.
We're different in a lot of ways, but she was like, there was Oprah Winfrey, the executive that built that business, but then she was Oprah on air, and she brought a lot of women a lot of value for a long period of time. And some men. Per Chris Voss, she's a savage negotiator as well, too.
I don't know if you know that. Do I know that? She was a client.
The Oprah Winfrey Network. Wow. Oh, you want a good one?
Yeah, go. Go look at Oprah's Instagram as soon as we stop recording. Go to the single first Instagram post on Oprah Winfrey's Instagram.
Go. I'm leaving it at that. We'll pop that up.
Last question that I ask everybody. How big can the Vayner Empire be? Everything.
Let's put it all under the sun. A lot bigger than anyone on earth believes. I'm going to build something incredibly big.
If God... is interested in giving me the 40 years i want to 90 i will build something not only big but meaningful and and will be a blueprint for a lot of good people who want to build savagery empires but will be capable of building it in a manner that's a little bit different than the way people think it needs to be done right now especially right now i think a lot of people think you've really got to have sharp elbows and sliced throats to get to the tippy top Right now, we put a lot of that on a pedestal.
I think there's a different way. And I'm very motivated by that because that will be a legacy that I'm proud of when I'm wrapping it up. It's going to be a lot bigger than almost everyone thinks, including all of you that are giving me flowers.
We're going to end on that, man. I appreciate you, man. Thanks for having me.
The Hook
The bait, then the rug-pull.
Most people know Gary Vaynerchuk as a motivational voice with 50 million followers. Here he spends 95 minutes as the operator instead, walking company by company through VaynerX, VaynerSports, VeeFriends and a restaurant group, and explaining the content machine that feeds all of it.
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A two-hour sit-down with a creator running three seven-figure businesses, including a live screen-share where he builds a full content strategy from scratch.
Two hours with Ronnie Fieg on 15 years of Kith: no paid ads, no wholesale, no outside money, and $1,300-a-foot stores that his CFO still cannot explain.
A 2 hour 45 minute sit-down on how virality gets engineered: ideas as the ceiling, 100 ideas for every video made, 10 titles and 3 thumbnails minimum, and a 45-second intro formula.
Six lessons from six rooms — Hormozi, Sanchez, Itzler, Srivatsaa, Hatter, and McManus — distilled into a single throughline: the edge is not talent, it is decisions.
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