So here's a question for you. Did you know that
the guy who, you know, seems to be on every social
media feed screaming at you to stop watching
Netflix and start hustling? Oh, I know exactly
who you're talking about. Right. That guy actually
started his career like dusting bottles of Pinot
Noir in a pretty standard New Jersey liquor store.
It's a jarring image when you put it that way,
isn't it? It's a very strange trajectory. I mean,
you go from selling booze in the suburbs to becoming
this this global avatar for the grind. For hustle
culture. Yeah. And now he's advising Fortune
500 CEOs and, you know, selling NFTs for. millions
of dollars. It doesn't quite track. Well, that's
the paradox of Gary Vaynerchuk, right? Because
if you only know him from, say, a 30 second Instagram
reel where he's dropping F -bombs and telling
you to wake up at 5 a .m. Which is how most people
know. It is. And you get this caricature. You
see the hustle guy. But if you actually ignore
the volume and I mean the literal volume of his
voice and look at the P &L statements, you see
a very, very different operator. And that is
exactly why I wanted to do this deep dive today.
Because I'll be honest, sometimes I see his clips
and I just feel tired. Right. I feel a little
bit scolded. But then I look at the businesses,
VaynerMedia, Resi, Empathy Wines, and I realize
there's this massive engine under the hood. A
huge one. So I want to know how that engine was
built. I don't really want the motivational quotes
today. I want the mechanics. How did he actually
make the money before he started telling everyone
else how to make theirs? That is absolutely the
right question to ask because the whole motivational
speaking thing, that didn't come first. That
was, in a lot of ways, the victory lap. The byproduct.
The byproduct, exactly. To really understand
the Vaynerchuk machine, we have to strip away
the Gary V persona and look at Gary Vaynerchuk,
the merchant, the guy who sells stuff. Okay.
So today we're going to track his path all the
way from a Soviet. immigrant upbringing to building
a $60 million wine empire and then pivoting to
a media holding company that actually rivals
the legacy agencies on Madison Avenue. And we
have a ton of source material to get through.
We've got the biographies, the financial reports
from his big company exits, the timelines of
all his media properties. It's a lot. It is.
But before we get into the chronological story,
what's the through line? Is there like a grand
unified theory of Gary Vaynerchuk? What's the
one idea that connects it all? There is. And
it's surprisingly simple. If you look closely
at every single venture, and I mean everything,
from the liquor store to the ad agency to the
NFTs, it all comes down to one single concept.
Attention arbitrage. Okay, stop there. Attention
arbitrage. That sounds like some marketing jargon
that an agency invents so they can charge their
clients double. What does that actually mean
in the real world? It sounds fancy, I know. But
it's actually dirt simple. It just means spotting
where people are spending their time, their attention,
before the rest of the market realizes it. And
therefore, before the price of advertising on
that platform goes through the roof, it's buying
attention for pennies on the dollar. Can you
give me an example? Sure. In 1996, that underpriced
attention was email. In 2000, it was Google AdWords.
In 2006, it was YouTube. More recently, in 2020,
it was TikTok. He doesn't build the platforms
himself. He just exploits the fact that big companies
are always too slow to move their money to where
the eyeballs actually are. So he's basically
a day trader, but instead of trading stocks,
he's trading. Eyeballs. That is literally the
title of his 2024 book, Day Trading Attention.
But yes, that is the mechanic. That's the whole
game. And to see how he first learned that, we
have to go way, way back. Before the internet,
we have to go to Bobruisk. Which is in modern
-day Belarus. Correct. Born Gennady Alexandrovich
Vaynerchuk in 1975, Soviet Union. And this is
really not a silver spoon story. Not at all.
The family came to the U .S. in 1978 through
a refugee resettlement program. He was only three
years old. They arrived with basically nothing.
And I think we hear immigrant story so often
that we kind of glaze over. It becomes a bit
of a cliche in these business biographies. But
we need to contextualize this. We're talking
about a studio apartment in Queens with, what,
eight family members? Something like that. Right.
It was incredibly crowded. And then they moved
to Edison, New Jersey. And this part is key because
he wasn't insulated. He wasn't inside playing
video games. He was on the streets selling things.
The classic kid businesses. The classic cliches.
Yeah. Baseball cards, lemonade stands. But he
took them to an absolute extreme. There's a story
that's often told about him running multiple
lemonade stands at the same time across the neighborhood
and managing his friends as employees. So he
was franchising. He was franchising lemonade
at seven years old. He was learning about profit
margins and stuff. scaling before he was even
10. But the real business education, the one
that really sets the foundation, that starts
when he's 14. That's when he gets dragged into
the family business. Shoppers discount liquors.
Not exactly a branding masterpiece, is it? No,
it sounds like the place you go to buy the giant
plastic jugs of vodka. Exactly. And it was a
volume business. His dad, Sasha, ran a very tight
ship. Gary started out, and this is true, by
bagging ice in the basement for $2 an hour in
tips. Bagging ice. Bagging ice. It's pure manual
labor. But eventually, you know, he gets permeated.
He moves up to the sales floor. And this is where
that attention arbitrage instinct first kicks
in, even though he didn't have a name for it
yet. How so? Well, he started watching the customers.
And he realized that people weren't just buying
liquid in a bottle. They were buying a story.
They were buying prestige or recommendation or
feeling. So he started studying? He started devouring
information. He read every issue of Wine Spectator
magazine. He wasn't just reading it. He was memorizing
the ratings, the reviews, the scores. Learning
the data. Exactly, the data. So when a customer
would walk in looking for some... you know, specific
$100 bottle of Cabernet, he could walk up and
say, hey, I know you like that profile, but this
bottle over here got a 92 from Robert Parker
and it's half the price. Ah, so he's building
trust. He's not just upselling. He's building
immense trust. He's providing value first. But
the real explosion, the thing that changes everything,
that happens in 1998. He graduates from College
Mount Ida College with a management science degree,
and he takes over the day -to -day operations
of the store. And 1998. I mean, we have to put
ourselves in that time. The Internet is basically
a baby. Most people are still absolutely terrified
to put their credit card information into a computer.
And that right there is the arbitrage. That fear,
that slowness from everyone else, that's the
opportunity. He looked at that behavior and said,
people are going to buy wine this way. I'm sure
of it. So he made two big moves. Two huge moves.
First, he rebranded the store. He changed it
from Shoppers Discount Liquors to Wine Library.
Which immediately sounds more authoritative,
more premium. Instantly. And then he launched
WineLibrary .com. He took the local liquor store
online. Okay, let's unpack this growth here.
Because the numbers, they're frankly absurd.
The source notes all say he grew the business
from $3 million a year to $60 million a year.
60. A 20x return. Right. And you don't get that
just by, you know, putting up a website. Plenty
of people had websites in 1998 and went completely
bust. What was he doing differently? Okay, this
is where we get into the real weeds of the tactics.
And the first one, the one that built the foundation.
was email email yeah simple email back in 1998
spam filters weren't really a big thing if you
sent someone an email they almost always opened
it your open rates were like 80 or 90 percent
it was incredible unthinkable today completely
so he collected email addresses at the checkout
counter aggressively. And he started sending
out daily emails with offers that were actually
valuable, not just buy this, buy this. He'd write
tasting notes, tell stories. He treated that
email list like gold. So he had a direct line
to his customer that cost him basically zero
dollars to use. That's it. A free broadcast mechanism.
But the bigger play, the one that really scaled
the business nationally, was Google AdWords.
Ah, the early days of search ads. The very early
days. When Google first launched their ad platform,
basically nobody was bidding on keywords for
wine. The big established wine retailers were
still spending millions of dollars on full -page
ads in the New York Times and on billboards.
And Gary realized he could buy search terms.
He realized he could buy the term wine, or Cabernet
Sauvignon, for pennies a click. Pennies? Literal
pennies. For a nickel, maybe a dime. he could
get a highly qualified buyer, someone who was
actively at that very moment searching for wine
to land directly on his website. That's an incredible
arbitrage. He spent every single dollar he had
on it. He milked that margin for years until
the big guys, the big retailers finally caught
on and started bidding the price up. But by the
time they finally showed up to the party, he
had already built a loyal customer base of tens
of thousands of people from all over the country.
It's fascinating. It wasn't that he was necessarily
a better sommelier, though he was good. It was
that he was a better media buyer. That's it.
He just understood the plumbing of the Internet
better and earlier than his competitors. Precisely.
He was using the wine to fund his real education,
which was learning how the Internet worked. And
that, of course, naturally leads us to 2006.
YouTube. YouTube launches. It's new. It's weird.
Nobody knows what to make of it. And we get Wine
Library TV. Or as he always called it, the Thunder
Show. The Thunder Show, that's right. He starts
filming these episodes in the back of the store.
He's wearing a New York Jets jersey. He's got
a big plastic spit bucket. And he's just screaming
about tannins and tasting notes. It was completely,
totally unpolished. And that was the whole point,
right? Because wine culture before this was...
you know, ascots and classical music in the background.
It was designed to be exclusionary. It was incredibly
stuffy. He completely democratized it. He made
it okay to not know everything as long as you're
willing to taste and learn. He'd taste a wine
and say it tasted like grass clippings or a dirt
clod. Things people can actually relate to. Yes.
But look at the work ethic here. This is what's
really key. He didn't do, you know, a season
of 10 episodes and take a break. He did a thousand
episodes. Thousand. One thousand. Daily. For
five straight years. Before he finally retired
the show in 2011 to start a new one called The
Daily Grape. That level of consistency is just
it's staggering. It is. And that's what he means
when he talks about hustle. It wasn't just about
working late. It was the relentless consistency
of the output. He was building a relationship
with his audience every single day. And he was
in the comments. He was in every comment section
replying to everyone. This is really the community
manager phase of his career. He realized. way
before anyone else, that the brand wasn't your
logo or your slogan. The brand was the conversation
that was happening in the comments section. OK,
so he builds this absolute beast. He's the king
of wine on the Internet. The business is doing
$60 million a year. The family is set for life.
Most people, I mean, 99 .9 % of people would
just ride that wave until retirement. Right.
They'd buy a boat, maybe open a second location
in a different town and just, you know, chill
out. But Gary isn't driven by the wine. I think
that's what becomes clear. He's driven by the
game. He saw that selling wine was just one application
of his actual skill set. His real skill was generating
and monetizing attention. So in August of 2011
he does something incredible. He walks away.
That is a genuinely terrifying move. to walk
away from the cash cow that you personally built
from the ground up. He stepped away from the
day -to -day of the wine business to start VaynerMedia
with his brother, AJ. And he did it because he
saw the next great arbitrage opportunity. Which
was? Social media for corporations. Okay, let's
look at VaynerMedia. Because back in, what, 2009,
2011, the idea of a social media agency usually
just meant a couple of the 20 -year -old interns
posting on a company's Facebook page. It wasn't
a serious industry. How did he turn that into
a powerhouse? Well, he essentially applied the
Wine Library TV model to Fortune 500 brands.
He looked at the traditional agencies, the Ogilvys,
the McCanns, and saw that they were all built
on the TV commercial model. A Mad Men model.
The Mad Men model, exactly. They would spend
six months and $2 million. to create one single
perfect 30 -second video. And Gary looked at
that and just said, that's completely stupid.
Stupid. I mean, that's how the entire industry
had worked for 50 years. It's a proven model.
It was proven for a different medium. He argued
that on a scrolling Facebook feed, nobody cares
about your cinematic production value if the
content isn't relevant right now. He pushed for
volume and speed over perfection. So instead
of one $2 million video. Let's make $1 ,000 videos
or $210 ,000 videos. Let's test them all. Let's
see what people actually click on, what they
share, and then let's put the real money behind
the winner. It's the Google AdWords strategy
all over again. Test cheap, find the winner,
and then scale it. That's all it is. It was a
newsroom approach to advertising. If something
happened in pop culture that morning, say an
awards show or a big sports game, VaynerMedia
wanted their clients tweeting and posting about
it by noon. And the big agencies just couldn't
move that fast. They were buried in legal approvals
and endless meetings. VaynerMedia was built for
speed, for the pace of the Internet, not the
pace of television. And the growth was, again,
just massive. By 2016, what are the numbers?
They're grossing $100 million in revenue. $100
million. And they have 600 employees. Ad Age,
which is the industry bible, puts them on their
coveted A -list of top agencies. He had proven
that tweets and posts were actually a nine -figure
industry. Here's where it gets really interesting
for me, though. Beyond just the agency's success.
It's the structure he built around it. You're
talking about VaynerX. Exactly. VaynerMedia is
just the agency. It sits under this bigger holding
company called VaynerX. And this is where you
see his ambition to be more than just a guy who
provides a service. Right. Because at the end
of the day, an agency is a service business.
You have clients and clients can fire you. It's
a constant grind for a new business. So he started
building his own media properties. He didn't
want to just buy ads on other people's platforms.
He wanted to own the platforms. That's where
the gallery comes in, which later became Gallery
Media Group. And this is the part of the company
that houses publishers like PureWow. Which is
a huge women's lifestyle site. Huge. And 1E37PM,
which is more of a men's lifestyle and culture
brand focused on, you know, crypto sports cards,
that sort of thing. So why do that? why own the
magazine and the ad agency it seems like two
different businesses it's all about control And
data. If you own the media company like PureWow,
you own the audience data. You know exactly what
articles women age 25 to 45 are reading, what
products they are clicking on, what content they
are sharing with their friends. So you can then
take that real time data, walk it over to the
VaynerMedia side of the office and tell your
client, Pepsi or Toyota or whoever, hey, we know
with certainty what content works right now because
we see it performing on our own platform. It
creates this incredible feedback loop that other
agencies just didn't have. That is actually brilliant.
It's a vertical integration for the attention
economy. That's a perfect way to put it. And
having that machine, that confidence, it gave
him the platform to start spinning out other
businesses. This is where we get into the full
-blown serial entrepreneur phase of his career.
And let's start with Rezzy because I, like a
lot of people, use Rezzy to book dinner reservations
all the time. I remember when it launched, it
felt like this cool niche app for foodies in
New York and L .A. I had absolutely no idea.
Gary Vaynerchuk was a co -founder. It doesn't
seem like his world. He co -founded it with Ben
Leventhal, who was a founder of Eater. And again,
you have to ask the question, why? Why does a
social media guy care about the restaurant reservation
business? I'm going to guess it's about data.
It's always about data. And friction. He saw
that the simple act of booking a table at a good
restaurant was a major friction point for consumers.
You had to call, they'd put you on hold, they'd
say we're booked. OpenTable was the big giant
in the space, but their software felt clunky
and old. It was built for desktops, not phones.
Right. Resi was mobile first, it was slick, and
it specifically catered to the cool, high -demand
restaurants that didn't want to be on OpenTable.
So it was another arbitrage. It was an arbitrage
on the dining experience itself. And it paid
off. Big time. American Express acquired Rezzy
in 2019. The exact terms weren't disclosed, but
the deal was significant enough to really validate
him in the tech world. He wasn't just a marketer
anymore. He was a legitimate tech founder with
a major successful exit to a blue chip company.
And then almost immediately after that, he goes
full circle. He goes back to the bottle. Back
to wine. Yeah. With empathy wines. But this time
it was a totally different model. Totally different.
He looked at the wine industry and saw that the
core problem was still distribution. In the United
States, wine distribution is a complete nightmare.
It's a mandatory three -tier system that was
set up after Prohibition. Right. It goes from
the winery to a distributor to a retailer, and
then finally to you, the customer. And every
single one of them takes a big cut, a big margin.
Which is why a decent bottle of wine costs $20,
but often tastes like it should have cost $5.
That is exactly why. Empathy Wines was designed
to break that model. It was direct to consumer,
DTC. He sourced high quality grapes from top
farmers in California who often had excess supply
arbitrage again, and he sold the finished wine
directly to his followers online. Cutting out
the distributor and the retailer. Completely.
So he could sell what was essentially a $50 quality
wine for $20 and still make a better profit margin
than the traditional wineries. And the brilliant
part is because he already had this massive audience
from his social media presence, he didn't have
to pay for advertising. He just posted a video
saying, hey, guys, I made a new wine. And his
followers bought it. His customer acquisition
cost was basically zero. That is the absolute
holy grail for any DTC business. And, of course,
the big guys noticed. Constellation Brands, one
of the largest alcohol companies in the entire
world, they saw this incredibly efficient model
and they just bought the whole company in 2020.
Okay, so just to recap, he's conquered wine twice.
He's conquered the ad world. He's conquered restaurant
tech. So now we have to talk about the elephant
in the room, the JPEGs. Web 3. I'm going to play
the skeptic here for our listeners, because when
the whole NFT craze hit, it really felt like
a lot of smoke and mirrors, a lot of hype. And
then suddenly there's Gary drawing these little
stick figures, calling them V friends and selling
them for thousands, sometimes tens of thousands
of dollars. So was this just a cash grab? Because
from the outside, it looked like he was monetizing
his fan base's loyalty in a very, very aggressive
way. And that is a very fair criticism. A lot
of people made that exact point at the time.
But if you look at the actual structure of the
VFriends project, he was trying to do something
fundamentally different than just selling digital
art. He attached utility to every single token.
OK, explain utility in this context, because
that word was thrown around a lot. So if you
bought a VFriend NFT, it wasn't just a digital
picture of, say, an empathetic elephant. It was
a smart contract that also acted as a ticket.
A ticket to what? Holding that specific token
gave you a three -year admission pass to his
big super conference, VCon. So the art was a
collectible, but the token itself unlocked a
real -world experience. So it's basically a conference
ticket that you can hold as an asset and then
resell on an open market. Precisely. And because
it's all in the blockchain, if you sell your
NFT to someone else for a profit, the original
creator, in this case Gary, automatically gets
a small royalty percentage of that secondary
sale. Okay, so the argument is... Don't just
look at the cute drawing. Look at the mechanics
of the smart contract underneath it. Right. His
big bet was that smart contracts are the next
email, the next AdWords, the next big platform
shift. And he wanted to be first. He wanted to
learn by doing. And the market, at least for
a time, responded in a huge way. He did a collaboration
with another project called Doodles that ended
up selling at a Christie's auction. A real world
established auction house. Yes. we're talking
about serious institutional money coming in and
validating this new space but let's be honest
the market crashed hard a lot of people who bought
nfts maybe even v friends lost a lot of money
they absolutely did and that is the inherent
risk of following a futurist if you buy into
the arbitrage too early Or more likely, you buy
in at the absolute peak of the hype cycle, you
can get badly burned. Now, to his credit, Gary
has always been very vocal about this. He's on
record saying 99 % of all NFT projects are going
to go to zero. But that doesn't really comfort
the person who bought a token at the top of the
market and saw its value collapse. No. And this
is where that guru status he has gets really
tricky. Because when people start to follow your
financial moves, they share in your wins, but
they also have to share in your losses. That
transitions us perfectly then to the content
machine. Because none of these businesses, not
the wine, not the agency, not the NFTs, none
of it works without his unbelievable ability
to command attention. The man is everywhere.
I open LinkedIn. He's there. I open TikTok. He's
there. YouTube, Twitter. It's endless. How does
one human being produce this much stuff? He doesn't.
He has a big team. And more importantly, he has
a system. It's a system he calls the content
pyramid. And it's actually something that's really
actionable for anyone listening right now. OK,
please break it down for me, because I struggle
to post like one good tweet a week. It's pretty
simple conceptually. It all starts with one piece
of pillar content. Pillar content. Yeah, that's
the big thing at the top of the pyramid. It could
be a long -form keynote speech he gives or a
podcast interview he does or one of his long
vlogs. Let's say he gives a one -hour speech
on the future of marketing. That speech is the
pillar. Okay, so he does the heavy lifting just
once. Right. Then his content team takes that
one -hour video and they just chop it up. They'll
go through it and find the five funniest jokes
he told, the 10 smartest business insights, the
three most controversial statements. Then they
turn those little moments into 30 or 40 short
vertical clips for TikTok, Instagram reels and
YouTube shorts. Wow. So one hour of work becomes
what, 40 or 50 individual pieces of content?
Easily. And that's just the video. Then they
take the audio from the speech and they release
it as a podcast episode. Then they get the entire
speech transcribed and they turn the best parts
into LinkedIn articles or long form tweets. And
I've seen them take a single quote, put it over
a picture of his face and post that on Instagram.
Exactly. One single keynote speech can fuel all
of his social media channels for an entire week.
It's just maximum efficiency. It's the volume
strategy we talked about with VaynerMedia. He's
just applying it to his own personal brand. He
is practicing exactly what he preaches. And you
should notice, too, the distinct flavors of his
different content shows over the years. They
each served a purpose. DailyVee, for example,
was a documentary series. It was like reality
TV for entrepreneurs. It was. It showed the grinds,
sleeping on planes, eating bad airport food,
having stressful meetings at VaynerMedia. It
was specifically designed to show his audience
that he wasn't just some talking head who gives
advice. It showed the work. And then you had
hashtag AskGaryVee. Right. And that was a pure
Q &A show. That was all about community engagement.
He would source questions directly from his followers
on Twitter and Instagram and answer them on video.
That show actually became so popular that it
was turned into one of his bestselling books.
Let's talk about the books, because he's written
a whole shelf full of them. And I think the titles
themselves, if you look at them in order, they
tell a really interesting story about how his
own philosophy has shifted over time. They absolutely
do. The timeline of his books perfectly mirrors
the maturity of the Internet economy itself.
OK, so you start in 2009 with Crush It. Crush
It. That was the original manifesto. The subtitle
was Why Now Be Is the Time to Cash In on Your
Passion. And you have to remember the context.
It came out in 2009 right on the heels of the
massive financial crash. People were desperate.
They were losing their jobs. They were desperate.
And he was coming in with this message saying
the gatekeepers are gone. The Internet is here.
Start a blog about what you love, work harder
than everyone else, and you will win. It was
pure, raw, unapologetic aggression. Then you
get into the more tactical stuff, like Jab, Jab,
Jab, Right Hook. Which is still, in my personal
opinion, his best pure business book. The entire
thesis is right there in the title. Give value,
give value, give value. Those are the jab. And
only then do you ask for the sale, which is the
right hook. Most businesses just throw right
hooks all day. Buy my stuff, buy my stuff, here's
a coupon. He explained very clearly that on social
media you have to earn the right to sell to somebody.
But then more recently, the whole tone of the
books changed. It got softer. In 2021, he released
a book called Twelve and a Half. This was a massive
pivot, a huge one. The subtitle is Leveraging
the Emotional Ingredients Necessary for Business
Success. We are not talking about crushing it
anymore. We're talking about empathy, kindness,
self -awareness, curiosity, gratitude. So what
prompted the shift? Did he just get soft in his
older age? Or did he realize that hustle culture,
the very thing he helped create, was becoming
toxic? I think he absolutely read the room. The
whole hustle porn era, you know, where founders
would brag about sleeping only four hours a night,
that was facing a massive cultural backlash.
People were burning out. People were burning
out. And the Gary Vee character was, frankly,
becoming a bit of a villain in that narrative.
Twelve and a half was his direct attempt to add
nuance to his own message. He started arguing
that you can work incredibly hard without being
miserable or being a terrible boss. He started
talking about things like kind candor. Kind candor.
I like that phrase. It's a great phrase. It basically
means you have to be able to tell people the
hard truth Firing someone, giving critical feedback,
but you have to learn how to do it from a place
of kindness and respect without being a jerk.
It was an attempt to merge that hard -nosed businessman
persona with a more modern, emotionally intelligent
leader. But let's be real. The criticism has
not gone away. There are plenty of people, as
noted in our sources, who still view him as a
snake oil salesman. Yes. And it's important that
we really apply some critical thinking here and
analyze why. The term snake oil implies you're
selling a cure that doesn't actually work. Right.
The criticism of Gary usually fall into two main
buckets. The first one is what's called survivorship
bias. Okay, explain that. The critics will say,
okay, Gary, you made it. That's great for you.
But for every one of you, there are 10 ,000 kids
who listened to your advice, dropped out of college
to build their personal brand, and ended up completely
broke. That's a very valid point. The odds are
not in your favor. Not everyone can be a media
mogul. It's a totally fair point. The second
main criticism is about the productization of
self. And the question is this. Is he selling
actionable business advice or is he selling the
feeling of being successful? That's a good distinction.
Think about it. When you watch a Gary Vee video,
you get a little dopamine hit. You feel motivated.
You feel energized. But after that 10 minutes,
did you actually learn how to read a balance
sheet or did you just feel good for a little
while? It's the idea of entrepreneurship. People
who are addicted to consuming content about business
instead of actually doing the business. Exactly.
And to be fair, Gary would argue that he puts
out thousands of hours of free tactical content
so you can do the business. He would say, I gave
you the entire blueprint for free. Don't blame
me if you didn't build the house. But that critique
remains. Does his high energy style accidentally
attract people who are looking for a magic bullet,
even though he explicitly says over and over
that there are no shortcuts? And yet. Despite
the critics, his ambition hasn't slowed down
one bit. He still talks constantly about his
ultimate goal, buying the New York Jets. That
is the North Star. That's the end goal of all
of this. He's a diehard, lifelong Jets fan, and
he has said publicly for years that his entire
career, all of these businesses, they are just
a mechanism to accumulate enough capital to one
day buy the team. You know, it's almost a protective
mechanism, isn't it? As long as he hasn't bought
the Jets yet, he's still... on the journey. He
hasn't truly won the game yet. That's a great
psychological insight. I think you're right.
If he actually buys the Jets tomorrow, what's
left? The game is over. By keeping that goal
so impossibly high, he ensures that the hunger
never goes away. So we've covered a lot of ground.
The immigrant hustle, the wine empire, the ad
agency dominance, the tech exits, the NFTs, the
books, the philosophy. For the listener who is
maybe sitting in a cubicle right now or maybe
trying to run a small business, what is the actual
practical takeaway here beyond just the you can
do it cheerleading? If you strip everything else
away, the single biggest takeaway is adaptation.
Just look at the timeline one last time. Okay.
1998. Email is the new undervalued asset he goes
all in. 2006. YouTube is the new undervalued
asset. He goes all in. 2011, corporate social
media is the asset. He builds an entire agency
around it. 2021, Web3 and NFTs are the new frontier.
He builds VFriends. He never fell in love with
the medium. Never. He didn't say, I'm a newsletter
guy or I'm a YouTuber. He said, I am a trader
of attention. That's the key. Don't fall in love
with your tools because the tools always, always
change. The tools always change. The consumer
behavior changes. The platforms change. The only
thing that stays the same is that people are
paying attention to something. And your job,
whether you are selling wine or widgets or just
yourself, is to find out where those eyes are
going before the price of admission goes up.
And to not be afraid to look a little bit stupid
while you're doing it. I mean, he looked ridiculous
spitting wine into a bucket in 2006. He looked
ridiculous to a lot of people talking about cartoon
NFTs in 2020. Being willing to be misunderstood
for long periods of time is an absolute superpower
in business. He was willing to be the crazy wine
guy for years until suddenly he was the genius
marketing guy. Before we wrap this up, I want
to leave the listeners with a final thought.
Something for them to chew on that maybe isn't
in the books or the speeches. I have one. It's
a question really for you to consider. We've
established that Gary Vaynerchuk is an absolute
master of content. He meticulously documents
his life in order to sell his businesses and
his philosophy. But at this point in his career,
you have to ask yourself, is the business driving
the content or is the content now the actual
business? Wait, what do you mean by that? I mean,
does VaynerMedia primarily exist to serve clients
like PepsiCo? Or does it exist to provide the
perfect backdrop for Gary's content about being
a CEO? Has he productized his own life so effectively
that the story of him doing business has become
more valuable than the business itself? That
is a real inception level thought. Is he a businessman
who is playing a character on the Internet? Or
is he a character on the internet who is playing
a businessman? Or perhaps in the modern attention
economy, there really is no difference between
the two anymore. On that bombshell, we are going
to sign off. Thank you for taking this deep dive
with us. Now stop watching us and go spot some
arbitrage. See you next time.