Gary Vaynerchuk – My Take & Learnings

I have gone toe-to-toe with Gary Vee not once, but three times. When most meet him, they get 15 minutes in the sun – that’s really what it feels like, when you have the attention of the man who collects Attention (more on this later). Those lucky enough to sit before the king of modern advertising ask their question, bask in whatever manic dogma ensues, and depart. But I challenged him. I looked right in the sun and didn’t blink. 

After the below video (my first meeting of three with him) I left with a ‘high’ I have never experienced prior or since. It felt like a lightning bolt hit my spine. It felt like someone really saw me for the first time in my life.

For 25 minutes I took the drug he seems to main-line, daily, and it was transcendent. But, like most drugs like that, it left me empty afterwards. The questions that seemed answered in moments revealed themselves to be puzzles that required years. Regarding my business, and myself, too (more on that below, too).

Before our second meeting, he told me “I don’t take second meetings, it either means you’re special or I’ve misread you and you’re wasting my time.” Now I just meet with his Chief of Staff and Head of Growth who relay him messages like he’s the god damn Wizard of Oz.

Gary is riddled with flaws. But, his critics seem to pick at the wrong seams. They miss the point and completely overlook his genius. There were months (years, maybe) where I was completely disgusted by him. After surviving three bouts in his ring, instead of his anointment, I received his shoulder – his promises dissipated, and his attention moved to the shinier, faster moving objects that fill his office dozens of times daily.

I was bitter then. But I’m not now. So, I’m penning a blog post to explain what I saw when I looked in the sun.

Most of what’s next sounds like I kept taking the drug he served me during that first meeting back in 2016. I assure you, it’s with clarity of thought and the textured and profound experience of 5 years of building a business in his domain that I dole the heaping praise in the ensuing paragraphs. 

First, his flaws: without a doubt, he’s gone too wide. He does much too much. He doesn’t follow through. It’s not just me. He misses things. He doesn’t double click. His mind went from “impossibly fast yet accurate” to “definitely manic and sporadic”. He barely has time for his own family. And though he repeats the mantra “go deep, not wide” to others, he doesn’t follow it. My indignation to one side, he is, without a doubt, the most formidable marketer of our time. Here’s why:

Gary Vaynerchuk is a perfect personification of modern advertising. He doesn’t just “practice” advertising as a profession, he has become it. He dog foods himself. He has built a sleeping, expansive empire beneath the much more visible media empire for which he is known. That’s the crux of it – most people are in awe of him for what he’s built, but they only see the bit sticking out 25 floors above Hudson Yards, not the twisted ball of yarn in his mind

Gary spends most waking hours concocting a kingdom that most of those who respect (or criticize) him entirely miss. Underneath the media conglomerate that bares his name, he has land-grabbed a secret kingdom of what is quickly becoming the scarcest resource on planet earth – Attention. Most people only see the surface of what he’s built – the companies, the angel investments, the sports agencies – not the kinetic well which quietly sits beneath his feet waiting to be tapped when the world is most thirsty for the very commodity he has in spades.

By day, Gary, runs 5 businesses, the largest of which is a media holding company called Vayner X. Inside Vayner X, among other things, is an ad agency (Vayner Media) with 900 employees that clears $125MM in revenue a year while the rest of “Madison Avenue” (old school Ad Agencies) are crumbling into the ocean. Not bad. This is all while running 4 other businesses – sports agencies, restaurant apps, wine companies – and investing (very early) in things like Uber, Snap, Twitter, Tumblr, Birchbox and dozens more.

Around his business dealings – before them, after them, and sometimes even during them, Gary Vaynerchuk is building the empire he actually cares about. Vayner X is the path of least resistance. It keeps the lights on, gets him access to important people, and is red meat for the peasants that occupy most of his schedule. His 50 year plan though – the would-be crown jewel of his legacy (something he cares a LOT about), and the thing that will give him the cash to buy his beloved NY Jets – is capturing the hearts and minds of young up-and-comers and stock piling their Attention. His holding vessel in this evil scheme is called “Gary Vee”. 

Gary Vee, Gary Vaynerchuk's online persona, often quips that he “day trades attention”. Translation? While doing what he ‘does’ in any conventional sense (marketing, investing, speaking) he documents the process, expounds on the journey, and creates an elaborate public persona which he blasts from a digital fire hose to over 10MM people more than 35 times per day (that’s a lot, even by 2020 standards).

His stream-of-consciousness is neatly packaged, and then repackaged, and then repackaged. It’s lacquered and emitted across over 8 different social platforms in small clips (or fractions of clips) where he has millions of followers – from TikTok to LinkedIn, from 12 year olds to 72 year olds. He spoon feeds his wisdom to throngs of ravenous, insecure up-and-comers for free. How very giving.

Drug dealers in 1980s New York were giving too. They would often flood the market with their most potent product and then charge more, later. Gary follows the same playbook. The knees of those he helps (his victims) are wobbling with youthful ignorance, digital loneliness, and fear of the ascent that lies before them if they are to succeed (many don’t know how). Gary lattices his advice, his wisdom, and his leading-by-example, to shine as a beacon of what could be. And he’s in your feed 35 times, daily, so you don’t forget.

Most of Gary Vee’s followers only have some vague understanding of his (other) business dealings. Instead they revere him as a guru; a self-help genius who holds the answers to self actualization, career fulfillment, and happiness. The bi-product? Gary has amassed a cult of >15MM young people who worship the ground he walks on and they don’t even know what he really does for a living.

At first, second or even third glance, Gary Vee is a malignant narcissist. He literally has a team of 16 full-time-employees (called “Team Gary Vee”) who’s sole purpose is flawlessly crafting his personal brand. They film every moment of his waking life, post to all social channels, and generally present him as an “everywhere-at-once” digital demagogue. Which he is, by the way.

Gary Vee is like crack to young, insecure viewers (the author of this post among them). And they can’t get enough even though he is brash, bombastic, and obsessed. Why then all the love? What about him is so compelling?

I learned at my first job (an even BIGGER agency than Vayner Media, called Y&R, which consequently will be dead in 10 years) that only those brands that adopt two diametrically opposed attributes can be great and separate themselves from their competitors. Y&R calls it “Brand tension”. It’s the only 2% of what Y&R makes inside their walls that isn’t commoditized sludge. Brand tension put more simply: to succeed as a brand (or person) you must be two (very different) things at once so you are unlike all the other people or brands that aspire to be like you. Being two things at once creates texture and intrigue for your audience. It makes you different and unpredictable.

Example 1: Target emerged from the big-box-space by being simultaneously “cheap” (as was Walmart, Kmart etc) and “chic” by investing in marquee designers and offering down-market-pricing for their elevated aesthetic. Example 2: Land Rover touts the rugged 4x4, off-road capability of their vehicles, but they sell most of their products for >$80k to suburban housewives who drive on paved roads. They are both “durable” and “luxurious”. Batman is a “dark hero”. Marilyn Monroe was “innocently seductive”. Jim Morrison (of the Doors) was a “badass poet”. You get it.

Gary, in one breath, is completely self-obsessed while also being completely self aware. He is selfish and empathic. A brilliant practitioner and a vague, predatory self-help guru who amasses loyalty by spewing truisms. It’s brilliant, unpredictable, and consequently intoxicating.

He knows he’s a manic megalomaniac. He knows he bites off more than he can chew. He knows he might lose one day (he claims to LOVE this fact and fancies himself a perennial underdog) because he wants to win too badly. But he knows … so it’s becoming. He leads with his vulnerability and his self awareness. He says the would-be criticisms of others before they can say them.

Above anything else, Gary heightens the understanding of self as the single most worthwhile exercise. If you understand yourself, and accept yourself, you can “quadruple down on your strengths” and “abandon your weaknesses”. Gary has practiced this principle wholesale – the very secret sauce he doles out to the hungry mouths that gawk at him – and it’s vaulted him to unprecedented success. He practices what he preaches, and it works, at least for him. The trick here is that his authentic self is a megalomaniac. So…it works(?).

Others – Tai Lopez, Grant Cardone, Dan Lok – appear to follow the same playbook. They have the same hallmark bravado. The same film-everything-and-flaunt-it protocols. They violently emit confidence and (way too) sleekly packaged answers to wealth, fulfillment, and even happiness. But, behind the digital firehose (replete with $20,000 suits, Lambos, private jets, and sold out arenas of people listening to their nonsense) sits empty guidance. They are modern day con-artists. Their kingdoms are self-fulfilling prophecies – they monetize the secrets to becoming successful – which in turn makes them successful. They start their journey with nothing – a lie – and build empires on the credit cards of suckers; only gaining power from the power they take. People say this of Gary but people that say this don’t understand the game he’s playing nor how he’s playing it. Gary, though brash, self-congratulatory, and even predatory at times, is accomplished, formidable, and…dare I say it, real. What he preaches is helpful even if (especially if) by following his advice you end up nothing like him.

Gary’s is, by my estimation, the most powerful personal band of our time. Yes, I live and breathe this industry. The point stands. His brand is more powerful than Floyd Mayweather, more powerful than Oprah, more powerful than Taylor Swift. Why? Floyd boxes. Taylor sings. That’s it. Gary clocks-in twice a day, every day. Once as a practitioner and once as as documentarian. A two-way-mirror to society. A vacuum for the very eyeballs that will become exponentially valuable in the next 20 years.

Gary understands what many intuitively know but don’t act on. Attention is by far the most valuable commodity of our time. And increasingly so. Gary floods the market with free content, attracts (extremely loyal) viewers and holds them (and plans to, for decades). Between his Twitter (2.1MM), TikTok (4.3MM), IG (8.1MM), and LinkedIn (4.1MM) he has the eyes and ears (and souls) of >10MM young people. His name (Gary Vaynerchuk + Gary Vee) is Googled 124,000 times per month. He speaks over 100 times per year (often for more than $100,000 an appearance – but it’s not about the money, it’s about the eyeballs – and the videos he gets from the speeches which he can later repackage). The ever valuable powder – our attention and loyalty – is bone dry. Waiting.

Unlike his look-alike peers who cash in on any eye ball they come across, Gary is collecting. It’s insidious and brilliant. No seminars. No quick-rich-schemes. He publishes a book here and there (though you could argue that’s “giving” more than it’s “taking”) sure, but that’s it. Mostly, he’s lying in wait, letting his stockpiled commodity-of-choice appreciate in value. And…just watch, as far as I am concerned, the attentional winter is coming, and every ounce of attention Gary has captured will be worth 10x what it is today when it’s harnessed into action (or traded in, in some form or another, for dollars).

Gary’s third book – the best selling “Jab, Jab, Jab, Right Hook” – has one message: provide value to your customers. Ask for nothing. Wait. Then wait some more. When the time is right, strike and ask for something back. Gary says “he who holds his breath the longest, wins”. In other words, hold out on monetizing the attention you command until you can’t breathe. He told me, in our second meeting, that if he could retroactively change the title (and correlated advice) it would be “Jab, Jab, Jab, Jab, Jab, Jab, Jab, Right Hook”. Translation: figure out a way to need less oxygen and wait even longer.

Others monetize what they do. They hit right hooks as soon as they can. Men try to seduce women two sips into the drink they bought them. Grant Cardone tries to sell you three separate courses if you so much as glance at one of his many ads online. People take. They cultivate value and as soon as it sprouts something edible, they harvest it, terrified it will rot on the vine otherwise.

Taylor Swift can’t tour forever. Floyd Maywhether certainly can’t box forever (in fact he retired two years ago). So, when Floyd boxes, he rakes in $$ from pay-per-view tickets and endorsements and…that’s that. Sorry, probably a confusing example, but he literally and metaphorically “Right Hooks”. He fights and makes money instantly. Sure, his likeness (like many famous boxers before him) will pay dividends until the day he dies. But both his boxing talent and his likeness are depreciating assets and every backpack or shoe or boxing glove he makes, sells, and benefits from, the less water there is in the well. Gary monetizes what he does (professionally) to pay the bills – marketing, investing, speaking – but his brilliance lies in his patience – what he really does is gather attention, slowly. The resulting Attentional empire is 100x bigger than the office in the sky at Hudson yards – trust me, I’ve seen it up close, three times.

———

When you meet Gary it’s like meeting your favorite 10 film actors all at once – if you’re in the industry then you’ve seen 100s of hours of his ever flowing stream of consciousness, and then suddenly, there he is, one man in a corner office.

His perch sits on the 25th floor of Hudson Yards atop midtown Manhattan – other buildings all but coming up through your shoes via floor to ceiling windows. It feels like you’re dangling in a cage in the sky. At his feet, and the feet of his revolving door of guests – the city over which he rules. At his back – “tombstones” of deals, gifts from iconic clients and friends and NY Jets paraphernalia (he famously boasts that his ultimate goal is buying them one day). The man surrounds himself with surrogates of his greatness. Still, I stand by what I said. It feels more like a cage than an ivory tower. Almost like seeing a powerful tiger at the zoo – trapped and sad.

Gary’s day starts at 6AM and goes until 11PM. The majority of his meetings are 15 minutes. That’s it. And he holds to that. In each meeting he listens until he doesn’t need to. For him, that’s about 14 seconds. In our meeting (below) he repeatedly and forcefully interrupts me “NEXT!”, “AGREE!”. As soon as he’s sized up your position (and he’s heard them all) he dives in, finds the crux, and shoots from the hip. To say he’s a finely tuned machine is such an understatement you wouldn’t understand unless you sat with him. The “value” most people derive from an hour meeting, Gary distills into 5 minutes. His whole day a compressed, fully saturated barrage. It’s unclear if his seemingly endless energy fuels his busy day or if the never ending meetings he schedules fuel his energy. I think it’s a loop. And, either way, he fucking LOVES what he does.

Other than certain family members and girlfriends, Gary has elicited the most intense emotional reactions out of me during my entrepreneurial endeavors. His endorsements, his absence, his advice, punchy and bold. He moves so fast. His empire is so vast. It seems to defy the laws of physics – or, at least, entrepreneurship – as I’ve come to know them. It’s hard to remedy your own failings. Your own pace. Your own existence, even, when you’re in a room with him. He reminds me of Mohammad Ali in his prime – the unlikely nexus of speed and power. You never know where the punches are coming from, and when they hit, they are crushing. When I find myself resting my tired entrepreneurial bones on platitudes of balance (things like: “no one can be ‘on' all the time”), Gary Vee stands as a gleaming exception to the rule(s). He is everywhere, always.

Also like a caged tiger, Gary doesn’t pay much heed to the people at the glass. He asserts frequently that he doesn’t care what anyone thinks. I think he does, actually, and that it’s a big part of what fuels him. Gary doesn’t listen to any one voice, that’s true. No one criticism. Instead he blends them together and chokes down the mixture like an overzealous smoothie every morning, filled with a bit too much green stuff. He protects and perpetuates the chip on his shoulder for it is his secret weapon – his modest immigrant upbringing, how he almost failed out of high school and college, how he built (10x) his dad’s humble liquor business well into his 30s without recognition nor financial recompense. The world didn’t see it. They overlooked him. Silly world.

It’s what makes Gary’s master plan all the more exceptional. Most people who are governed by the chip on their shoulder grab hastily at validation and reassurance wherever they can find it. Their insecurity demands it. Gary, while fundamentally insecure, is at peace with his insecurity. He can “sit with the feeling” to quote a San Franciscan maxim. 

Gary is comfortable in the shadows. That’s the thing people miss – most people think he’s loudly and brashly at the top of his game – really, though, most of what he’s building is modestly below the surface needing neither your approval nor awareness. One day, it will swallow this industry whole with you inside.

In our meetings, Gary promised me mentorship. And I wanted it, badly. Though his promises rang hollow, he was able to provide value in his 15 minute flybys – it’s sort of his ‘thing’. His wisdom which he ejects in the video below rings truer the more I age as an entrepreneur. Most of all, this sentiment:

“You’ve already won. Just shut the door and get on the hamster-wheel. Once you do, though, you can never get off.”

In the past few months, thanks to how COVID has simplified my life, those words ring daily in my ears. 

The door he speaks of is the door to the outside world. COVID has taken so much of that away. Now, for example, I don’t socialize, I don’t date, it’s just me and my goals – entrepreneurial and personal in nature. The door he speaks of is the door which separates where I am from the perceptions of where I ought to be. Sometimes the judgements come from my parents. Sometimes a girlfriend. Most, they come from my own fear my own demons. Closing the door is hard even if it means silence from those voices. It almost feels like the same door that shuts out fear also shuts out support and love, too. And that’s mind numbingly lonely.

The hamster wheel he speaks of is how repetitive tasks are. Particularly the small tasks that make up large goals. Anything worth doing takes decades. And anything that takes decades has so many small repetitive tasks inside. Building something glamorous isn’t glamorous for the people who actually build it. Hardly ever. So, if you’re too focused on the outcome you can’t tolerate that the system isn’t moving. It can feel like you’re stuck and not progressing. But, if you can find solace in the repetition, you win. A few days, lately, I’ve said out loud on my daily walks “if every day could be like today, I would be truly happy”. Sometimes I am walking by myself, even.

I used to feel trapped by my existence. The idea of getting on something (a hamster wheel, say) and never getting off sounded like torture beyond anything I could bare. My brain, ever moving and so self doubting, would feast on itself. “Being you must be exhausting”, my therapist likes to say. Lately though, I don’t want to get off and the spinning bothers me less. I realize that the motion in my brain, the output of my soul, and the repetition of it all, is all part of my progress, too. In fact, it’s even a prerequisite to my fulfillment. A circuitous gateway to my potential. It’s hard to imagine that potential could be reached when you’re spinning, seemingly motionless, on a hamster wheel. Potential sounds like a destination. An outcome. Not a process or consistent way of being. But, sometimes the running, itself, is all that matters. Where you are (the hamster wheel) is also, consequently, where you need to end up (also the hamster wheel). When the foil stays the same, the only thing that will change is you.