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Gary Vaynerchuk: Predicting Success in a Budding Empire



It’s 1994, and Gary Vaynerchuk is nineteen. He wraps up a game of “John Madden Football” and runs into the other room, where his ears are met with a cacophony of dial-up sounds. You know…pshhhkkkkkkrrrkakingkakingkakingtshchchchchchchchcchdingdingding. His friend is getting on the Internet, and, without so much as a pause, Gary has the realization that “he can sell shit on this thing.”

Vaynerchuk’s ability to understand consumer behavior better than the average person is very real, and he’s built an empire that’s a testament to his entrepreneurial mind and work ethic. Vaynerchuk and his siblings were raised by two Belarusian immigrants who instilled in them the conviction that self-esteem and entitlement are not the same thing. Self-touted as a “lemonade stand and baseball card collector kid,” Vaynerchuk’s entrepreneurial spirit began at a young age. He’s keeping many fingers in many pots, the contents of which keep turning into gold.


In May of 2018, Vaynerchuk purchased a 50 percent stake in the L.A.-based full-service creative house Green Street Agency, which works exclusively within the cannabis space. Upon hearing whispers of Gary’s cannonball into the cannabis pool, ears perked. As an early investor in Twitter, Tumblr and Facebook, his investment in the cannabis space feels very much like a prediction of the future success of this budding industry. But the reality is, Vaynerchuk admittedly knows very little about weed—for now. “My college friends are going to laugh their asses off that I am on the cover of your magazine, because their four-year quest in college was to get me to smoke a blunt with them,” Gary loudly states, his words punctuated by laughter. Mom and Dad? “My Mom was super-propaganda’d out by Nancy Reagan. I think right now, if you lie detector tested me, I would say my Mom would be like, ‘Mmmmmmmmm,’ and my Dad would be like, ‘He’s a genius—that’s gonna work out.’”

Cannabis Has an Image Problem

Insiders and outsiders alike agree that the cannabis industry has an image problem. When in 2006 Vaynerchuk launched Wine Library TV, a popular video blog in which he de-mystifies the beloved alcoholic beverage, his goal was to “break down the barriers, stereotypes and misperceptions that otherwise prevent people from exploring and enjoying the exciting and rewarding world of wine.” This sentiment rings eerily familiar to many of the concerns floating around the cannabis space. Can we look to Wine World TV as a model of what we could be doing in the cannabis space to not only normalize the plant, but remove barriers, stereotypes and misperceptions? Vaynerchuk states simply, “Cannabis is an obnoxiously young business—and industry.” He goes on to say that, unlike cannabis, wine has the luxury of having existed in the legal marketplace for centuries and a more mature footing as a consumer good, despite its bout of prohibition in the United States. “Among all of the strains and different flavors in the [cannabis] industry now, getting somebody who has actually tasted and tried them on that scale and can articulate the flavor profiles and nuances and the understanding of the subtleties needed to be that big voice . . . There are just not a lot of those animals running around at this point.” Vaynerchuk suggests that the arrival of that animal is inevitable, and will essentially just take some time. This sounds like a challenge: racers, start your engines.

Cannabis as an Entrepreneurial Incubator

When Gary and his brother AJ founded VaynerMedia, a modern-day ad agency, in 2009, they realized early on that corporate America was slow to pick up on content strategy trends. One of the numerous reasons why VaynerMedia is currently in the business of video production, social media and non-video content? VaynerMedia wanted to be able to support their clients outside of consulting. The ad agency’s household name clients include GE, Budweiser, Chase Bank and Toyota, to name a few. There is sincere curiosity as to whether or not the cannabis industry is making a similar mistake as corporate America. “No,” Vaynerchuk assures me. “I think cannabis, from my observation early on, is really good at [understanding content strategy trends], because there are such young entrepreneurs who are native to that communication.”

Gary Vaynerchuk on Stage

Gary Vaynerchuk on Stage

Unlike almost every other industry, cannabis is unable to advertise on platforms like Facebook, Instagram and Google in all the ways they wish they could. Vaynerchuk actually thinks that “the cannabis industry is going to be the teacher of innovation” as it pertains to the creation and curation of content. As an industry and as “pure bread entrepreneurs,” we won’t have a choice but to lead as innovators in a hotbed. Whether justified or not, cautious and antiquated positions continue to reign supreme when it comes to marketing barriers aimed at cannabis businesses, brands and media companies. Vaynerchuk states authoritatively, “I am comfortable making this prediction: In 2040, cannabis companies are going to be the ones influencing the way diapers, tires, soda and shampoo are being sold.” In his view, being forced into unorthodox advertising strategies may result in cannabis brands becoming leaders in the future of marketing tactics.

Why Are We Sprinting While Training for a Marathon?

Vaynerchuk often speaks to the importance of building one’s own brand. The average person gets so caught up in expansion, they fail to realize that they’re sprinting in the marathon that is life. “I would be lying if I didn’t tell you that I’m aware of a lot of people in the industry, and that my voice is uniquely beneficial to this industry because you have an enormous amount of people who are obnoxiously short-term,” Vaynerchuck states in a serious, take-my-advice tone. He spends an insane amount of time studying emerging markets. “I’m looking at the emerging gambling market, Supreme Court rulings, cryptocurrency and cannabis, and what’s happening in these markets is that, oftentimes, you get three to four percent pioneers and 96 percent hucksters, right? And there are an obnoxious [number] of hucksters in the cannabis industry now—because they like smoking weed, or they see it as a trend, and they want to cash in fast.”

Related – Buds in the Sun: Utilizing Nevada’s Rugget Terrain for Cannabis Marketing

So, the question really becomes: do you want to be a pioneer or someone who shills questionable, low-value goods? Many would choose the former, and this is where Vaynerchuk’s advice comes in handy. “To me, it’s very simple. Life is actually a marathon, so wouldn’t it be a good idea to train for a marathon? It’s the framework—let’s be patient. Don’t invest all of your money in something that seems like, ‘This is a new formation of cannabis or hemp.’” Vaynerchuk likens this “sprint” to people chasing a lottery ticket. If you are in the cannabis space, start thinking about how the hell you’re going to stick around for 20 or 30 years.

To me, it’s very simple. Life is actually a marathon, so wouldn’t it be a good idea to train for a marathon?

Vaynerchuk asserts this time and time again—that he’s constantly thinking about the long-term, the marathon. VaynerMedia secured its roots nine years ago, and now the company employs over 900 people and has made hundreds of millions in dollars. Vaynerchuk points to a few of his Silicon Valley colleagues, stating, “A lot of people started companies from 2009-2011, the same time I did—my homies in Silicon Valley who raised millions and millions of dollars . . . Those companies? They are now out of business. Too much short-term thinking.” Vaynerchuk’s advice if you’re in the cannabis space, or any space, for that matter: If you’re there for the lifestyle and not the business, then you shouldn’t be there at all.

Don’t Call GaryVee a Pundit, Guru or Motivational Speaker

Vaynerchuk wants to be viewed for what he is. “I spend 85 percent of my time being an executive of a 900-person, four-office company. I respect execution too much [to be called a pundit or guru], only being a speaker or an author or a pundit is pontificating, and not doing,” Vaynerchuck shares pointedly. By his own admission he enjoys sharing his insights and predicting the future, but he gets to talk the talk because he’s walked the walk.

“Very simply,” Vaynerchuk says, “I think it’s a lot better to take advice from someone that has done the thing they are fucking talking about . . . I have a lot of cynicism of someone who writes a business book who has [only] been a professor at Yale their whole lives.”

Gary Vaynerchuk

Despite hundreds of Vaynerchuk’s interviews and speeches that can be found on the web, he doesn’t often share or get asked what the hell he does for fun. Yes, he loves working. “You can’t imagine how fucking fun my professional life is to me. I lived the first 20 years of my life scrutinized, and was told that I wasn’t going to make it. That became my strength,” Vaynerchuk states, reflecting on his youth. Despite his numerous haters, Vaynerchuk appears to be a hell of a nice guy. When he isn’t at a New York Jets game or spending time with his family—which he says is his favorite thing to do—you’ll find Vaynerchuk watching a documentary, listening to a podcast, shooting hoops or picking through other people’s throwaway items at a garage sale. “No joke, the thing that is most fun to me in the world is garage sale-ing. I like to buy things for a dollar and flip them on eBay for nine,” he states seriously. Vaynerchuk is on a mission. That mission? To make people understand that the quickest way to be unhappy in life is to allow someone else to dictate your emotions.


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