Gary Vaynerchuk | Climbing the Ladder (Episode 448)

Gary Vaynerchuk | Climbing the Ladder (Episode 448)

Gary Vaynerchuk | Climbing the Ladder (Episode 448)

Do you think of people who pursue their passions and make good money doing it as lucky? Chances are that Gary Vaynerchuk works a lot harder than you.

“Let me just clarify one thing — I’m not lucky!” -Gary Vaynerchuk

The Cheat Sheet:

  • How did a kid from the Cold War era communist Soviet Union manage to escape in the late ’70s and become one of the hardest-working capitalists alive today? (06:03)
  • For all of its flaws, the US is still a better place to seize opportunity than most of the rest of the world. (09:41)
  • You may think you’re a hard-working hustler, but how do you compare to a hard-working hustler from Belarus? (13:54)
  • If you’re comfortable living in a world that’s convenient for your mindset, you’re poised perfectly to lose. (18:40)
  • Learn why Gary Vaynerchuk chose to open an office in Chattanooga, Tennessee. (25:31)
  • And so much more…


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From selling baseball cards as a kid to transforming his family’s three-million-dollar liquor store business into a 60-million-dollar wine shop to starting VaynerMedia — a 600-person social/digital agency — while running investment fund Vayner/RSE, Gary Vaynerchuk outworks all of us, and he shows no signs of stopping.

Oh, and he writes books, makes videos, and speaks to large groups of people. Frankly, we’re kind of surprised we got him to sit still long enough to talk to us! In this episode of The Art of Charm, we seize the opportunity to field what we think is a very unique interview with this Belarusian immigrant kid who teaches us a thing or two about chasing the American Dream.

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More About This Show

You may know him as “that wine guy,” but Gary Vaynerchuk keeps himself occupied on so many fronts that it’s a little hard to keep track of everything he does. Before talking to us for this episode of The Art of Charm, Gary told us he’d been working on his latest book for about 12 hours. (He’s already written four that we know of, and most of ’em were New York Times bestsellers.) What’s been taking up 70-80 percent of his time of late is his social/digital agency VaynerMedia (think Mad Men 2015), but he also runs investment fund Vayner/RSE, which strives to “build tomorrow’s companies today.” He also dispenses wisdom about marketing, social media, and entrepreneurship on his #AskGaryVee Show (currently up to episode 155 as of this writing).

Realizing all of these projects would be considered an ambitious day’s work by any bachelor’s standards, but this is where we mention that Gary is also a family man with a wife and kids — and if his Twitter byline is any indication (“Family 1st! but after that, Businessman.”), he takes this job more seriously than a lot of self-described workaholics in his situation would.

Gary’s story began back in 1975 when there was still a USSR and Belarus was still called Babruysk. Even though his family moved to the USA when he was just three, the Soviet way of life must have made an impression — of what to avoid at all costs.

“I’m a straight capitalist entrepreneur meritocricist — everything against the Soviet point of view — that is me,” says Gary. “I’m actually completely driven by gratitude; I’m so thankful that the place where I was born was not the place that I grew up!”

Through a fluke of policy that tended to restrict emigration, Gary’s family was allowed to leave the country based purely on ethnic distinction.

“We left in ’78 when Israel and the US teamed up…and made a trade with the Soviet Union to let Jews in Russia out. And so basically, as weird as it sounds, I was traded for wheat!”

When asked if he ever wonders how much wheat he was worth, Gary has a quick answer.

“I swear to God,” says Gary, “based on how many taxes I pay in this country, I do think about how awesome of a trade that was for the US!”

Gary’s future was further directed when his father, unable to continue a career in construction because of a fortuitous housing market collapse, was forced to become a stock boy in a liquor store in New Jersey — which eventually led to business ownership that Gary would successfully build upon. It may not have been the path he would have chosen, but he worked with the tools he was given and it gave him the opportunity to launch into the various ventures he pursues today.

“I talk about how much I hate complainers,” says Gary, “and I think it stems from the fact that I don’t think people understand how good we have it. You could talk about the shrinking middle class, which is real. I hate the separation of wealth in the US; I do think it’s too disproportionate. There’s plenty of racism. There’s sexism. There’s a lot of crap, right? A ton. Unlimited amount. Greed. There’s enormous crap. By comparison to the rest of the world’s crap, it’s remarkable.”

“If you’re listening right now and you live in America,” he continues, “I highly recommend you just pinch yourself out of happiness, because I think that people are completely flabbergasted and lost and just don’t have a good context on how much opportunity there really is in the scheme of things by comparison.”

Listen to this episode of The Art of Charm in its entirety to learn how Gary responds to high school friends who call him “lucky,” the dangers of living in a world that’s convenient for your mindset, and some choice tidbits of the Gary Vaynerchuk story that he assures us he’s never shared with anyone else! Enjoy!


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