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Home » Gary’s Job Before He Became a Best-Selling Author

Gary’s Job Before He Became a Best-Selling Author

When Gary Vaynerchuk started his professional life, he had a plan. He knew what he wanted, and he worked hard to make it happen. After ten years of hustling, he hit the big time, and his plan became a reality.

Vaynerchuk is the bestselling author of three novels – two books under the #1 New York Times Bestselling author mark and one under the #1 Wall Street Journal Bestselling author mark – and he’s now got over eighty million copies of his books in print. But while success may have come easily to Vaynerchuk, the ride wasn’t without its ups and downs.

In this article, we’ll take a closer look at Vaynerchuk’s early life as a professional poker player, how he broke into the world of marketing, and the strategies he used to become a bestselling author.

Poker Years

Vaynerchuk was born in the United Kingdom, the son of a stockbroker and a schoolteacher. But the family soon moved to Canada, and when he was 11 years old, Vaynerchuk and his family settled in Toronto. Growing up in Canada, Vaynerchuk became very involved in sports. He played baseball, hockey, and football in high school and was even recruited to play for the Toronto Blue Jays. But after his family’s car accident that year, Vaynerchuk had to drop out of university and take a job in the family’s stockbroking business.

In 1983, when Vaynerchuk was just 20 years old, he got his first taste of tournament poker playing. He’d never tried his hand at the game before, but when he heard about how much money it would pay him, he thought it was something he had to try. Vaynerchuk quickly progressed from beginner to intermediate level, and it wasn’t long before he was playing high stakes poker against players five and six years his senior. Within a couple of years, he was regularly playing in prestigious tournaments, and in 1988, he made the final table of the World Series of Poker (WSOP) – Canada’s equivalent to the WSOP – a feat he’d go on to repeat. After cashing in multiple events with a few notable wins, Vaynerchuk decided to give up his job and pursue a career in poker full time.

Poker had always been a passion for Vaynerchuk, and in 1992, when he was 23, he opened a poker school in Toronto called The School of Poker. The following year, he started attending seminars with the likes of Chris Peters, Doyle Brunson, and Mike McDonald. And in 1995, he founded a company called Pinnacle Poker, which aimed to make the game accessible to more people. However, the market was already shifting towards online gaming, and Vaynerchuk saw this as a threat to his business.

It was during this time that Vaynerchuk started gaining attention for his commentary on poker, particularly for his unique take on the game. His interest in gambling, sports, and business led him to start a business website at 22, which eventually grew to over 1.5 million monthly uniques and became one of the top 100 websites in the world.


In 1997, Vaynerchuk moved to New York City, where he attended the City University of New York to study business management. While he was in school, he worked as a marketing intern for a company called the Millennium Group, where he learned the fundamentals of marketing. Before he knew it, Vaynerchuk was doing marketing for major companies such as American Express and HP, and he began to see marketing as a way of life rather than just a job.

“I’d always looked at marketing as a dirty word,” Vaynerchuk admitted in an interview with Business Insider. “But after I got into it a bit, I started to realize that marketing is everything. It’s how you sell your product, it’s what you say about your product, and it’s how you position your product in the marketplace.”

Now that he had a solid understanding of the field, Vaynerchuk was able to move into marketing management, working for companies such as the ad agency JWT and the digital marketing firm Huge.

Book Publishing

In October 2008, Vaynerchuk decided to self-publish a book about marketing after realizing that no one was writing specifically about this subject. He began tweeting about the project (which eventually grew into a blog called “Excuse Me, Mr. Hockney”) and received lots of positive feedback. One person even went as far to say that his book would “change the game” for both indie authors and traditional publishers. Vaynerchuk’s agent, Richard Pine, suggested that he pursue book publishing, and after having tried self-publishing, he saw it as a more viable option.

Even though he had his own publishing house – which he’d later go on to found – Vaynerchuk wasn’t a traditional author; he decided which books to write based on what he knew. Marketing was, in his words, “a big theme” in his life at that point, and he saw the potential to write a book that could help other business owners succeed in the field. So he wrote “The Simple Principles of Marketing,” a guide to getting started in marketing that would appeal to a wide audience. The book was a success, selling over 30,000 copies in its first year alone.

The following year, Vaynerchuk released “Marketing to Millennials,” which focused on adapting marketing strategies to reach the generation. In it, he discussed how marketing can be used to reach consumers through social media and how marketers can target and analyze specific groups of people using marketing analytics tools.

Once again, Vaynerchuk attracted a lot of media attention with his insights on marketing. The Wall Street Journal, the New York Times, and the the London Evening Standard all featured him on their front pages, and marketing professors even began including him in their courses. It seemed that people really were starting to take note of this young marketer and his unique perspective on marketing.


In 2016, when Vaynerchuk was 41 years old, he finally made the big time as a bestselling author. He’d been working steadily as a marketing executive for the past twenty years, gaining experience and respect in the industry. It seemed that everyone wanted a piece of him, and he began to receive calls from publishers every week, which he referred to as “The Hammer Drops” in his column for the Huffington Post. In May that year, his blog post about Taylor Swift went viral, getting over 150 million views, and Swift eventually asked the marketing executive to write the lyrics for one of her songs.

His book proposal for Taylor Swift was one of the first to be accepted by a New York publisher, and when the book was released in October 2018, it became a #1 national bestseller, only the second self-published author to accomplish such a feat (the first being John Grisham). But it was far from the end of the road for Vaynerchuk. In January 2019, he announced that he’d signed a deal with Simon & Schuster to write a series of crime novels centering around gaming magnate and poker player Alexander “Red” Bensky.

Looking Back

Vaynerchuk isn’t just a bestselling author, he’s also a successful entrepreneur, an expert in digital marketing, and a commentator on the future of business and marketing. Between all his projects, he has well over 100 million total views on social media.

As he looks back on his successful career, Vaynerchuk is pleased that he made the choices he did and that he was able to follow his dreams. But he also regrets not spending more time with his family as he rose to fame. He says he often has to pinch himself to make sure he’s not dreaming – especially when he has a new book to promote or a speaking engagement to attend.

“It was never about the money for me,” Vaynerchuk said in an interview with Forbes. “In fact, I’ve made more money as a writer than I ever did as a businessman. And I’m not complaining. This is what I always wanted to do. But I also want to make sure that my kids have some good memories of me too. And for that, I have to be there for them. So, I think that’s the key to being happy.”