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Seated inside Gary’s office in Manhattan, Andrew could get a sense of what it was like to be a part of Gary Vee’s world firsthand. Assistants and staff everywhere, all with phones or devices in their hands, all needing Gary to see something or record a quick video or…just craziness! Knowing that Gary was about to sit down and give an hour of his undivided attention- or as undivided as Gary’s attention can get- to him, Andrew took a deep breath and gathered his thoughts about the conversation to come.

Of course, Gary Vaynerchuk, or simply Gary Vee, needs no real introduction to anyone with either an Instagram, Tik Tok, YouTube, or Facebook account. His ubiquitous content that he shares on all platforms in a seemingly endless stream reaches millions every day. Tapping into the power of association, Andrew was hoping that this exposure with Gary would bring his message to an even greater audience than his already considerable following. Knowing that Gary was somewhat reticent to talk outright about money, Andrew would need to utilize all of his skills as an interviewer during their conversation. The following is that conversation.

“I’d like to get your thoughts on this idea I have, that certain things, you know when we’re growing up, we’re not supposed to talk about. Money, religion, and politics, right? Those are taboo subjects. Why do you think that is?”

“And sex. We don’t talk about sex in America. But yeah,” Gary answered in his signature mile-a-minute cadence, “we don’t talk about that stuff. It’s sad but that’s how it was for so many of us.” Gary explained how his parents immigrated to the U.S. from Belarus and settled in northern New Jersey. As a young teenager, Gary began working in his father’s wine and liquor store stocking shelves, mopping floors, and doing anything generally nobody else wanted to do. Like so many other immigrant families, Gary’s family held onto their ethnic roots and traditions firmly but embraced the culture of America and the opportunities of their new home. Learning business at such a young age proved to be the only education Gary valued, he was never a great student at school, and his entrepreneurial spirit blossomed.

Flipping baseball cards and other side hustles filled Gary’s days as a youngster growing up in the shadow of New York City, and he became a passionate Jets fan as well as a wine connoisseur as he assumed a larger role in the wine shop business. Always adept at sensing opportunities for business and expansion, Gary identified that the internet would be a huge vehicle for growth. In the early part of the dotcom era, Gary rebranded his father’s liquor store as the “Wine Library” and opened a website for the business. He also was an early adopter of YouTube and hosted a wine-themed YouTube channel. Gary’s efforts grew his father’s business from a $6 million per year business to over $30 million per year. He would work 14 to 16 hour days and never paid himself more than a modest salary even as the business more than quadrupled.

Through all that success, Gary developed his core ideas about business and money before he began to build his digital marketing and advertising media empire. He expressed some of his ideas in response to Andrew’s own articulation of his law of money- money must move or it dies. “Look I agree a thousand percent,” Gary spoke in that rapid-fire manner, “Moving money is crucial to what the wealthy do to create more money. But the average, you know, Joe Blow on the street doesn’t have two nickels to rub together, so what is he gonna move? The major problem with money is that people spend money.”

That statement came and went as fast as a lightning flash, and Andrew knew he’d have to jump in to get a follow-up. “Wait, so you’re saying that people spend too much money? Or just spending at all?”

“I’d say spending at all, really!” Gary laughed at his extreme position, but only half-heartedly because he really believed that many people should be spending much less. “Look, spending is necessary, right? But people buy dumb shit. People will go and buy the dumbest shit to wear twice to impress, you know, their friend that they hate. It’s pointless. I have people come to me and ask me, ‘Gary, how did you have $50 grand to invest in Facebook when you were just starting out in business?’. And they’re standing there wearing Louis Vuitton and Supreme and they just got back from Coachella! I didn’t buy dumb shit. If you make 50 grand live as if you make 30, and save the rest. Most people’s house is too big, their apartment is too nice, and they buy $7 coffees. There’s your answer.”

Gary had just passionately made his case for frugality and Andrew agreed. Andrew knew that many people made the poor decisions they made because of a lack of education about money. He asked Gary what his thoughts were concerning the rules of money- creating it, keeping it, and protecting it. “So what do you feel is a way that the average person can start to make better decisions? Because I’ve come across the same people. When I teach a class of people about money, I’ll have someone come up to me and tell me everything would be fine if they just made 60 grand instead of 40 grand or 200 grand instead of 175 grand, and it’s a perspective issue I think.”

“Totally. See, I believe it’s not how much money you make, it’s how much you spend. You can create all the money you want, but if you don’t keep any of it and set it aside or invest it to grow it and protect it, then you lose. You’re right back at broke. And I know people who make 300 grand who are as broke as a guy making 35 grand, or even more broke because they went into debt to sustain a lifestyle.