What Gary Vaynerchuk Learned by Experimenting on Himself

Gary Vaynerchuk is half man, half brand, half digital experiment. And somehow, that all adds up.
What Gary Vaynerchuk Learned by Experimenting on Himself
Image credit: Photographs by Pieter Henket / Groomer, Blair Jaffer

Gary Vaynerchuk arrives at his Manhattan office at 8 a.m. There’s no slow ascent -- no sipping coffee while scrolling through emails, no idle chitchat to forestall the onslaught of responsibility. Instead, as he does every morning, he quickly huddles with the two people who will accompany him throughout the day: his personal assistant, which is typical of most executives, and his personal videographer, which is, let’s just say, a profoundly Gary Vaynerchuk kind of role.

The assistant, Tyler Schmitt, runs Vaynerchuk through the day’s schedule. There are 24 meetings, including check-ins with the staff and clients of his digital media agency, VaynerMedia, as well as a wild assortment of guests -- social media stars, athletes, actors, musicians, many with entourages in tow. As usual, the action will be captured by the videographer, David Rock, nicknamed D-Rock. When the time comes, D-Rock will raise his camera, train it on his boss and barely take it off him all day, except during sensitive client meetings.

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“All right, you guys ready?” the 41-year-old CEO says to Rock and Schmitt, who are now standing with a few other members of what, internally, is known as either Team Gary or Gary’s Team -- a 16-member group that also includes a brand director, designers, merchandisers, influencer marketers and business developers. “Let’s start the show.”

At 8:10, the guests start arriving. There’s an interview with a potential executive hire, a podcast recording with Digg founder Kevin Rose, a talk with a young Dallas entrepreneur who won face-to-face time with Vaynerchuk in a Twitter competition. Then another meeting, and another, in blocks of five minutes up to an hour, with Vaynerchuk gesturing, laughing, swearing freely, peppering each visitor with questions and offering assessments. “You need a teammate, so let the things you aren’t gravitating to yourself lead you to the partner you’re looking for,” he tells Daina Falk, creator of the Hungry Fan sports tailgating site and cookbook, who is working to manage her brand’s growth. “I really do think Facebook is Netflix’s biggest competitor, so listen -- write a TV show, but do it on Facebook,” he tells Greg Davis, Jr., a.k.a. Klarity, a 32-year-old actor who wants to expand his social following.

Gary Vaynerchuk

There’s a string of internal confabs. “If I’m the bottleneck, let’s try a meeting where everyone hurls questions at me and I can only say yes or no, just to clear up the things that get clogged,” he suggests to his management team. (They try it two days later. It doesn’t work; Vaynerchuk talks too much.) There’s the surprisingly businesslike crew from hit Instagram meme-machine FuckJerry, reps from the NHL, a Los Angeles style blogger and rapper Sean Combs’ social media team. “Diddy’s trying to reach a new audience,” says Deon Graham, the boss. Vaynerchuk is all over it. “Puff has energy, so let’s give your new team the reins on new ideas,” he says. The ideas themselves will come after a dinner meeting between Combs and Vaynerchuk, which Graham vows to set up. After a round of the requisite selfies, which almost every visitor takes with Vaynerchuk, they bounce. More meetings convene. Scheduled ones, impromptu ones, conference room drop-ins, Sorkin-esque walk-and-talks. I ask Schmitt, the personal assistant, what happens if someone cancels a meeting. He looks at me blankly. “He finds a meeting.”

Through it all, Rock is a persistent fly on the wall, training his DSLR on the action. Sometimes he’s in the room, sometimes he grabs scenes from outside the glass partition, moving the camera around for dramatic effect. Originally, Rock produced this reality show himself -- filming and editing the videos of Vaynerchuk and uploading them to social. Now he has a team of videographers, which speeds the turnaround. The meetings I witness today will be cut up, subtitled, set to a beat and released tomorrow as a show called DailyVee on YouTube (to Vaynerchuk’s 645,000 subscribers) or in quick hits on Twitter (nearly 1.4 million followers) and Instagram (1.7 million).

The clips tend to capture Vaynerchuk frenetically hammering home his favored themes -- focus on your strengths, work your ass off, spot the next big shift and get there first, stop obsessing over stuff that doesn’t matter, be the bigger person, give more than you get and above all, execute. All this output, plus his relentless social media engagement and videos where he answers viewers’ questions, has fostered an ever-growing group of fans who treat him as an all-knowing sensei, enamored with his ability to cut right to the heart of their problems. And that, in turn, has turned him into an entrepreneurial celebrity. In addition to the videos, he pumps out books, podcasts and many conference keynotes, and is now costarring in Apple’s first-ever original TV series -- a tech-based reality competition called Planet of the Apps -- alongside Jessica Alba, Gwyneth Paltrow and will.i.am. Last spring when he tweeted that he was in London and offered to meet with followers, 200 people converged on a city park, all hoping to pick his brain, #AskGaryVee-style. (That would be his YouTube Q&A show, of course.)

This high profile has also drawn a different, less flattering kind of attention. The world of entrepreneurship is, to be frank about it, full of hucksters -- people who had one business success, or maybe skipped that part entirely and went directly into wisdom-spouting mode. To the polished bosses of old business in their sepulchral C-suites, Vaynerchuk can look a lot like King Huckster himself. After all, who the hell is so sure of their golden word that they’d pay a videographer to tail them?

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Vaynerchuk insists this doesn’t bother him. “Underestimating me is what I fucking live for,” he says. And anyway, to dismiss Vaynerchuk is to overlook something important about how to build a brand today. He is the living, breathing version of what digital marketing can do -- because once he started mainlining himself into the internet, it helped him be a successful entrepreneur, which made him a celebrity, which helped him become an even more successful entrepreneur, which made him an even bigger celebrity, with each part feeding the other. His net worth has grown to $160 million, and his fast-growing agency now employs more than 700 people and pulled in $100 million last year.

Gary Vaynerchuk is, in other words, what every brand wants out of social media. He connects and excites and inspires loyalty. So, the thinking goes, if brands want all this -- to connect and excite and inspire loyalty -- they should be more like Gary Vaynerchuk.

Gary Vaynerchuk


If you’ve ever heard Vaynerchuk interviewed, you’ve likely heard him tell his origin story -- in which a small-time wine guy discovers the power of digital marketing. But the tale is really more than that; it’s about how a small-time wine guy realizes the power of personality. His father, Sasha, took over an anonymous New Jersey liquor store in the early 1980s, shortly after emigrating from the then Soviet Union, where his son was born in 1975. Vaynerchuk assumed operations after college in 1998 and began experimenting. He rebranded the store as the Wine Library, then initiated online sales and fired off weekly emails to customers with special deals -- both pioneering moves at the time. Sales grew from $4 million annually to $45 million in just five years.

Entrepreneurs will often say that constraints are valuable -- that they force people to be creative. Wine was Vaynerchuk’s constraint. Alcohol is hard to market; there are regulations about advertising, serving and transporting it. But, he realized, there were no restrictions on marketing himself talking about wine. In early 2006, barely a year after YouTube launched, Vaynerchuk created a daily show on the platform called Wine Library TV. He turned out to be a natural communicator, something he attributes to growing up trying to understand his father. “My dad doesn’t talk. He literally doesn’t talk. The human does not speak,” Vaynerchuk jokes. “So I’ve had to spend my life trying to extract from him what he was thinking and feeling.” This turned out to be a valuable skill, because marketing, by its very nature, requires the same sort of intuition. 

You must infer and analyze based on small, stray amounts of feedback. You listen, in effect, by speaking and listening for echoes.

Wine Library TV earned him coverage in Time, an appearance on Late Night with Conan O’Brien and a book deal. It also made him itch for a bigger platform. The YouTube show gradually evolved into conversations about business and entrepreneurship. His followers became more interested in marketing than merlot. At that point, wine became a constraint that was no longer valuable. “I had so many ideas but couldn’t execute them all at the Wine Library,” he says. 

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This, it seems, is where Vaynerchuk’s philosophy crystallized. Like every marketer, he originally thought he needed somebody’s product to sell. A marketer without a brand to manage seemed like a bricklayer with no bricks to lay. But the digital revolution changed that. It may be an old observation now, but what Wine Library TV taught Vaynerchuk back then was still a revelation: People could be brands. He could be a brand. And by treating himself like one, he could fashion himself into a walking, talking R&D lab, testing his more forward-thinking marketing theories on himself, without having to gain some client’s permission first. Then, if his personal brand took off, he could package those theories and strategies and sell them to clients, in effect helping them be more like Gary Vaynerchuk. “I never actually set out wanting to be a personal brand, leveraging that to sell my own stuff,” he says. “Instead it’s how I learned my craft, by being the plumber and the electrician and the general contractor. I got to test my beliefs.”

One of those beliefs became this: Provide value over and over again -- educate, entertain, enlighten -- and then present your “ask” to the audience. Subscribe to my channel. Buy some wine. Read my book. (He’d go on to spell this out in his 2013 book Jab, Jab, Jab, Right Hook. The jabs are the value; the right hooks are the asks.) So he handed control of the wine shop back to his father and began preparing for his biggest ask yet: If you like my social media insights so much, hire me to execute them on your behalf. In 2009, Vaynerchuk and his brother AJ launched VaynerMedia.

Gary Vaynerchuk


In its first few years, as Vaynerchuk transitioned away from the wine operation, VaynerMedia lingered in double-digit personnel and a few million per year in revenue. With time, however, came traction. The company opened offices in Los Angeles, Chattanooga and London. It signed bigger and bigger brands. Last year revenues were up 50 percent over the previous year, to $100 million. In 2016 it moved into shiny new digs in a massive Manhattan high-rise to house the agency, a newly launched investment fund (Vayner/RSE) and a two-year-old sports agency (VaynerSports).

The VaynerMedia office is a spectacle. It contains endless rows of open-space desks populated by more than 700 strategists, marketing experts and business-development personnel -- most of them young and few with typical agency backgrounds -- who manage clients’ digital marketing campaigns, influencer programs, e-commerce strategies and technology integration, as well as personal brand development for celebrities, CEOs, artists and athletes. The staff also includes 200 writers, designers, photographers and animators, all focused on helping large companies and huge stars act more like their boss.

Here, on a grand scale, is where Vaynerchuk’s philosophy that what works for a one-man brand can translate to the world’s largest companies -- including General Electric, Unilever, Diageo, Toyota and Chase -- is put to the test. Louis Colon III, director of the Heritage line at Fila North America, says Vaynerchuk’s strategic personal touch on social resonated immediately. “Gary understands firsthand what it is to be an underdog and an entrepreneur,” Colon says. “We’re in a highly competitive industry in footwear and apparel, and for us to stand out, he helped develop a cadence of interesting storytelling that keeps the consumers’ attention.” That’s meant a steady stream of product launches amplified through social media placements and collaborations with athletes, artists and retailers, on their channels and Fila’s. “We never ask for the sale, we just ask to be a part of the conversation and to have the consumers’ attention.”

And what does a brand do with all that attention? It engages. Through Vaynerchuk’s personal brand-building, he’s found that heavy engagement -- replying basically to everyone who reaches out -- boosts not just your following but also your reputation. Today, 85 percent of his 135,000 tweets are replies. He wrote a book about this, 2011’s The Thank You Economy, and the point is reproven on social all the time.

Sometimes his clients need more than content help; they need to be awakened to the breadth of digital possibility. When Toyota hired Vaynerchuk to help with social strategy, it wasn’t leveraging new social tools or platforms fast enough. “Gary’s point was that anyone marketing for today is a full day behind. That opened everyone’s mind up,” says Jack Hollis, a group vice president and general manager at Toyota Motor North America. Vaynerchuk pushed them to be in new places first. Facebook video could become as significant as TV ads, he said. Demographically appealing influencers should be hired to help market specific car models, rather than brand-wide. Toyota did so, and entered Twitter, Instagram and Snapchat in ways it hadn’t before -- even as Vaynerchuk warned that the clock was ticking fast on every new strategy.

But as VaynerMedia helps teach brands what it knows, Vaynerchuk is also creating a pipeline for ideas to come in -- so that he’s learning from the next generation of social stars. This is a big part of why he so happily meets non-clients in his office. During that endless-meeting day, for example, he sat down with Farokh Sarmad, the 22-year-old founder of a luxury lifestyle Instagram feed and website called Mr. Goodlife. The guy had racked up millions of followers, but he wanted Vaynerchuk’s advice on growing his business further. Vaynerchuk sensed a mutual opportunity, so he began a trade. First he provided value. Rely less on Instagram, he told Sarmad, because at any moment the platform could change its terms and screw him. “I’ll help you build infrastructure to be independent,” Vaynerchuk said. Then he made his ask. “I want to siphon off as much exposure as possible from your audience. When we meet again, be prepared to have that meeting.” 

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Once Mr. Goodlife departs, Vaynerchuk admits he may not get much out of that deal. Their two brands barely overlap. But that’s fine. “I don’t think equal trades are always necessary,” he says. “What I gain from these exchanges is the big-picture wisdom -- the psychology of how creators and followers view these new platforms, the nuances of how they’re used. I get people’s insights and make my own decisions for both my own brand and, yes, the brands that hire VaynerMedia.”

The man feeds the brand, and the brand feeds the man. The synchronicity has worked well for him so far. And he’s discovering that as both parts of his life grow bigger, the balancing act gets even more complicated.

Gary Vaynerchuk


Vaynerchuk hands me his cellphone and points to a text message he received earlier in the day. It’s from a client asking him to personally tweet about their promotion. He shakes his head. “There’s a bright line around that,” he says. “I’ve done maybe four posts in seven years that have promoted clients, and only because they were noble causes.”

These requests happen every few months. It’s wise to turn them down. If he sold access to his Twitter feed, it would devolve into spam and trigger a tailspin: He’d become less interesting to fans and brands alike. Yet it’s easy to understand why a client would expect otherwise. Vaynerchuk and VaynerMedia are ascendant, intertwined entities. Toyota, for example, also hired him to speak at a critical meeting with the company’s regional directors. And as he builds his sports agency, he’ll occasionally pitch himself as part of a deal. Sign his athlete, he might say, and you’ll also gain access to him, behind the scenes, advising on marketing. It can get confusing -- when he’s for sale, and when he’s not. 

To strike the balance, he’s building it into the very fabric of VaynerMedia. He’s clear up front with clients about what his role will -- and will not -- be. To make clients comfortable with a team of people who are not named Gary Vaynerchuk, he makes a big deal out of hiring top talent. He calls his company the honey empire -- as in, a powerful entity built to attract people -- and dubs his executive in charge of HR, Claude Silver, the chief heart officer, to emphasize the importance of treating workers well. “If we get the people part right,” Silver says, “you’ll see phenomenal results in the empire part.”

He’s also built what he calls the Office of the CEO, a team of four VaynerMedia veterans who serve as his proxies throughout the company. They’re stationed in the mission control center, right outside his glass-walled office -- alongside, rather symbolically, all the Team Gary personnel. The four Office of the CEO members consult continuously with division leaders, update Vaynerchuk, and then funnel his feedback back outward. That way everyone at this increasingly sprawling company can feel like they have a line in to the boss. “The goal is to build a bigger, scalable version of the chief of staff idea,” Vaynerchuk says, “to give me more operational eyes and ears in different pieces of the business. If I’m going a thousand miles per second and can’t keep up with everything, this gives me a way to see things through.”

Here’s one thing he won’t do, though: Pull back on the Gary Vaynerchuk show. “I get so much out of it. It allows you as a talker to listen and get feedback, on a vast scale,” he says. But in conversations with him, I can see him working through the distinction -- wanting to support both his personal brand and his business, but without one overlapping the other. “I don’t want anybody to hire us because of me,” he says. “It’s OK to be aware of us because of me, but that’s where it ends. Look, marketing and personal branding are important. It’s real. But it doesn’t trump what goes on behind it.”

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Instead, he’s come to think of his two brands as on divergent paths -- that one day, VaynerMedia can be a thriving media company that’s eventually fully separated from his own brand, in both appearance and practice. 
Because when he looks back at the world’s greatest companies, he sees that they succeeded not because of their leader’s public profile but because of their leader’s true skills as an entrepreneur. “If you’re good enough at what you do, the market plays itself out,” he says. “Steve Jobs was ridiculously great at self-promotion. Bill Gates wasn’t. They both won.”

In a digital world, yes, a person can become a brand. Vaynerchuk has done that. Building a brand that stands on its own? That’s harder. But do it right, and it lasts longer than any one man.

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