How Gary Vaynerchuk Got His Start in Business and Became “Obsessed”

Gary Vaynerchuk, a businessman, Internet personality, and the CEO of VaynerX, unveils his humble beginnings.

Gary Vaynerchuk is an entrepreneur, speaker, Internet personality, and the CEO of VaynerX known for his work in digital media and his knowledge of wine. He sat down with the podcast HawkeTalk to talk about the steps he took to get to where he is now. Erik Huberman, host and CEO of Hawke Media, dives in detail with Vaynerchuk’s personal success story and how his curiosity, practical, and people skills became the crucial step for his now multimillion dollar company. Watch the full interview here.

On his family’s humble beginnings


Gary Vaynerchuk was born on Belarus in 1975. As his parents struggled to migrate to America, raising him on foreign ground, he became exposed to the business realm at an early age.

Erik Huberman: What drove you to be the person you are now?

Gary Vaynerchuk: 1975 – 1978 Belarus to 20 year-old parents is like 1930s America. It’s hard for Americans to understand that Russia was more like a third-world country back then. The way we got to America was through Austria and Italy. We lived with my great-grandparents, my aunt, and uncle. The first year was really rugged.

My dad had a very well-off great uncle, his grandmother’s brother, who was going to help us but while we were in Italy, he died.

Big credit to Arlene Newman and Bob Siegelman, though. They helped my dad buy a car, a job as a construction worker in their construction company, and ultimately got a job for my dad as a stock boy in the liquor store that the family owned. It was in Clark, New Jersey, and my dad started working there two to four bucks an hour.

My dad got promoted to be the manager of the store. What ended up happening was that New Jersey changed liquor laws. There was something called a regulation which meant that every liquor store in New Jersey had to mark up every product; 35% minimum as a baseline markup. Liquor stores thus became good businesses.

My dad teamed up with some other guys he met early on in the industry and they started a co-op called Shoppers Discount Liquors and they began selling liquor and beer at a very low cost. They all chipped in money and started running ads in the newspaper.

Huberman: So where did that come from? Where did your dad get his entrepreneurial spirit?

Vaynerchuk: DNA game. My grandfather, my dad’s grandmother, and my grandfather’s mother were very entrepreneurial by the legends and stories I’ve heard.

On his first entrepreneurial endeavors


Gary was not like the usual kid who was playful and plainly curious. The hustle is in his blood and it showed early on.

Vaynerchuk: In hindsight, I spent a staggering amount of time doing business. When it snowed, you could count on me at least half the day shoveling snow.

I went between lemonades, snow shoveling, and the one I’m least proud of, picking flowers in people’s yards and then ringing their own doorbells to sell back the flowers. One of my friends’ favorite one, given my Jewish roots, was the Christmas carol business I started. A big, big one was washing the cars.

Gary Vaynerchuk at the World Travel & Tourism Council, CC BY 2.0, via Wikimedia Commons

Huberman: How old were you when you started all this?

Vaynerchuk: Seven to ten years old.

Huberman: Was there something you wanted money for or was it just that you love the chase?

Vaynerchuk: I love the chase.

Basically from 10 years old to 17, 80% of my energy and mentality was around sports cards, buying them, and selling them. I was obsessed. In my dad’s liquor store, I would stand behind a table at a card show in a mall and basically spend 10 hours a day watching people. I learned by observing people.

On starting a company from scratch


Despite involving himself in the family business at a young age, Gary left the company to start his own with not much money.

Vaynerchuk: In family businesses, if you’re the COO or CEO of a business that you drove from 3 to 65 million over a seven-year period, it’s unlikely that you’ll still be paid sixty thousand dollars a year. But that was the truth of my life.

At 34, I had to start all over again when I founded Vayner. Luckily, I was a saver and didn’t spend money so I had some money to invest in Facebook and Twitter.

We actually had to start Vaynermedia in Buddy Media’s conference room.

Huberman: Do you know those guys? What’s the relationship?

Vaynerchuk: Somebody connected us. Lazerow, being the mensch that he is, not only gave me free conference room to start Vaynermedia, but also gave me equity in Buddy Media in exchange for a quote on their website.

On starting a family and new beginnings


Despite everything that he went through, Gary thrived in many aspects. As his businesses grew and more people started to recognize him, he was able to stumble upon the woman who would later be his wife.

Huberman: When did you meet your wife? When did that part of your life start?

Vaynerchuk: That happened in 2003. I got married in 2004. I had a kid in 2009, right when we started Vaynermedia.

About then, I also wrote a book, Crush It!, which completely exploded and was a massive New York Times best selling book. It changed my profile from wine guy to social media guy.

On his vision, dreams, and future goals


As a believer and a businessman, Gary always had his hopes on the future that he’s building right now.

Huberman: Vision for the next 10, 20 years?

Vaynerchuk: I want to build VaynerX to be the greatest communications machine of all time: live events, VR and AR media, Alexa skill building. I would like it to be a death star.

Huberman: You’ve said before that you’re not a big business book reader. Where do you gain all this? Where does your knowledge come from?

Vaynerchuk: I am basically reading people 24 hours a day. If I’m taking a flight to San Francisco, I just don’t want to do actual work. I’m not watching a movie. I go on Twitter, Instagram explorer, reading current events.

Huberman: One piece of advice for someone that’s starting out?

Vaynerchuk: Everyone’s got their own path. I would gravitate towards the grandparents in the playground as a child. What I did learn from those is that old people have a lot of regrets.

So my piece of advice for somebody that’s starting out is spend as much time as possible trying to figure out the cross-section of what you love and what you’re good at. It’s worth wasting your 20s and 30s because it’s not a waste.

Watch the full interview here.

Erik Huberman is the Founder & CEO of Hawke Media, a full-service Outsourced CMO based in Santa Monica, CA that launched in 2014 and has been valued at $60 million.