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The Success Story of Gary Vaynerchuk- The Most Pragmatic Entrepreneur

Gary Vaynerchuk
Gary Vaynerchuk (Picture credit: ChristopherMichel from flickr

Welcome to Youth Motivator. I would like to tell you the inspiring success story of Gary Vaynerchuk.
He is the CEO and co-founder of VaynerMedia and an early investor in several technology start-ups like Facebook, Snapchat, Twitter, Tumblr, Uber and Venmo.

Gary is also a best-selling author, venture capitalist, consultant, wine connoisseur, digital media mogul, web show host and a YouTube influencer.
He is well acclaimed for his hustle, entrepreneurial spirit and effective digital advertising.
This article is the biography of Gary Vaynerchuk.


Gary Vaynerchuk (Gennady Vaynerchuk) was born on November 14, 1975 to Sasha Vaynerchuk and Tamara Vaynerchuk in Babruysk, Belarus, Soviet Union.
In hopes for a greener pasture, the three year old Gary and his family immigrated to the United States in 1978.

Due to lack of sufficient money and options, they faced numerous difficulties in their initial days in America.
Gary along with his eight other family members lived in a very confined studio apartment in Queens, New York.

At that time, his family was so poor that it cannot afford a baby seat for Gary’s sister, Liz and so, his parents utilised a car seat found in the garbage as baby seat.
Both his parents Sasha Vaynerchuk and Tamara Vaynerchuk worked very hard and lived the American dream.

To make the ends meet, Sasha Vaynerchuk worked for long hours as a stock boy in a liquor store in Clark, New Jersey.
He used to daily commute to work from Queens to the liquor store in New Jersey.

Eventually, Sasha Vaynerchuk was promoted to the position of the assistant manager and then, the manager in that liquor store.

Starting his own business-

A few years later, Sasha Vaynerchuk moved his immediate family to Edison, New Jersey and started a liquor store.
Like majority of the immigrants, Gary’s family did a wise thing of saving up the earned money for many long years and this enabled them to start their own business.

Gary considers his father and mother as his real heroes and credits his success to their meticulous upbringing.
He is very inspired by his father because he immigrated to America with nothing and set up a huge wine business all by himself.

Realising his strength-

In school, Gary was notorious for being a terrible student and consistently received poor grades.
Fortunately, he and his mother were quick to realise that education is not his cup of tea but business and hustling is.

Since Gary‘s childhood, he possessed the traits of a successful businessman like keenly observing the human behaviour and possessing the intuitiveness on the factors which motivated the individuals to buy or sell.

Like many successful entrepreneurs, he started his business endeavours early in life.
Gary started his entrepreneurial journey in Edison, New Jersey by plucking the flowers in his neighbour’s garden and then, selling them back to them at a profit.

Starting his lemonade stand franchise-

When he was 6 years old, he set up lemonade stand franchise around New Jersey and made his friends to work for him at the lemonade stands.
At that young age, Gary realised the importance of branding and so, he named all his eight lemonade stands as Gary’s lemonade stand.

Later, he used to travel by a big-wheel around the town to collect the profits.
In his high school, at the age of 11, during the weekends Gary started selling baseball cards, toys and Blow Pops.

As at that time, the baseball cards were very popular in the US, he also conducted baseball card shows in the malls of New Jersey.
This gave Gary an opportunity to better understand the demand and supply model and thus enabled him to earn around one to two thousand dollars every weekend.

Soon, he became a rich young kid and a very efficient salesman with the potential to successfully convince the people to buy his baseball cards.
Gary’s life transformed when his father converted him from being a good salesman to a really potent entrepreneur.

Sasha Vaynerchuk utilised his savings to buy a liquor store in Springfield, New Jersey and named it as Shoppers Discount Liquors.

Getting dragged into his family’s business-

Once, the 14 year old Gary was collecting his cards together for attending one of the biggest baseball card shows in New Jersey but his father suddenly ordered him to come to the store.
His father forcefully took him to the store because he was not convinced with Gary attending the show.

This made him to cry and he couldn’t stop his tears until he neared his father’s store.
Gary also grew very disappointed on knowing that he would be paid a meagre two bucks an hour for working at the store.

This made all his previous business ventures to come to a screeching halt.
For the next year and half, as Gary was the eldest son, he worked on every weekend and holiday in his dad’s basement of the liquor store bagging ice and stocking shelves for 10 hours a day.

He did not stop working even though he hated that experience.
Gary was not allowed upstairs until the age of 16 due to the legality issues and was made to work only in the basement.

Later, he was allowed to work on the upstairs and here he got an opportunity to learn to deal with people by observing how his father interacted with the customers.

Making the connection-

On one fine day, many people visited the store for purchasing the 1990 Caymus Vineyards Special Selection Cabernet Sauvignon because it was the Wine Spectator's Wine of the Year.

As the stock was unavailable, many customers left the store without making any purchase and this disappointed Gary.

So, even though the store did not have any back order system, he took the back orders by noting the name of the customers, their addresses and the quantity of the wine required.
When Gary was 17 years old, he came across a wine collector who backordered six cases of Caymus wine and this incident changed his life forever.

By this incident, he made the connection and realised that he can sell wines to the wine collectors in the similar manner in which he sold baseball cards to the baseball card collectors.

Falling in love with wine-

At that point, Gary fell in love with wine collectors and gained confidence in his capabilities and also decided to help his family.
Later, he determined to become the greatest wine expert and build a large wine business and open up 4,000 liquor stores across America.

Gary’s plan was to sell the wine franchise one day and buy The New York Jets football team.
This determination sparked an interest in him to perform research on the wines and converted him into an oenophile (an oenophile is an expert of wines).

As Gary developed interest in the wines, he did not hesitate to work every single Saturday while in his 20s.
He never took an off on Saturday and worked 52 Saturdays a year, every year until the age of 29 and this consistency differentiated him from the other 20 year olds.

Thankfully, Gary’s expertise of selling the baseball cards helped him in selling wine and contributed immensely in the success of the Shoppers Discount Liquors store.
He exhaustively spent 15 years of his life (from the age of 15 to 30) for researching the wine and this made him a wine expert.

Also, as Gary was a poor student at school, he understood that he had only one asset to succeed in life, that is to work hard and so, he worked for 15 hours every single day for more than 20 years.
Only when he met his wife, he started working on having a better work-life balance.

Realising the power of internet-

In 1994, in Gary’s freshman year of college while hanging out with some of his nerd friends in the dorm room, he was accidentally introduced to the internet (information superhighway).
As he was very excited by the internet, he stood in front of a computer and watched the people on the internet for five straight hours.

Within a few seconds after spending his time on the AOL bulletin board, Gary observed that the people were trading the baseball cards and he quickly realised that he can sell things by using the power of internet.

In the next year, he started learning about the e-commerce platforms like eBay, amazon and also about the internet culture.
In 1996, Gary started, one of the first e-commerce wine businesses in the United States.

In 1997, he started an email newsletter and at the time most of his customers even did not know about email.
Gary collected thousands of emails and by the next year, he had a two hundred thousand email newsletter which had a whopping 91 per cent open rate.

In 1998, he graduated with a bachelor's degree from Mount Ida College and started expanding his father’s offline liquor store into an online wine business and in the same year he took over daily operations.

Later, Gary re-branded the Shoppers Discount Liquors into Wine Library and started selling the wines online through

Marketing effectively-

In 1998, his family was running a 3 million dollar business which made only a 10 per cent gross profit, so there was not much money left for the marketing.
So, Gary spent whatever the money he had on the meagre marketing and formulated a strategy of day trading attention.

He advertised mainly by attracting the attention of consumers and by finding the marketing models which were under-priced.
Gary also took a great care to not overspend money on the traditional marketing techniques.

He leveraged the power of e-commerce to turn his family’s wine business from $3 million a year to $60 million a year.
Gary accomplished this revenue by 2003 and it took him seven years to achieve this.

He also utilised the power of email marketing, banner advertising, Google Adwords, print, radio, etc.
Gary’s favourite entrepreneurs include Jeff Bezos, Steve Jobs, Mark Zuckerberg and Evan Spiegel and he believes that the internet helped most of them to become very successful in a short span of time.

Getting married-

In addition to helping Gary to exponentially grow his business, internet also helped him to find the love of his life.
In 2003, he met his wife Lizzie on Jdate, an online dating service meant for Jewish singles.

Thanks to his intuition, on the very first day, Gary knew that she was his perfect life partner.
On 13 November 2004, he married Lizzie and this couple is blessed with a son Xander Avi Vaynerchuk and a daughter Misha Ava Vaynerchuk.

Gary’s intuitiveness also helped him to become a judge in the Miss America 2015.
Prior to this, in 1980s, while watching the Miss America pageant with his mother and sister, he correctly predicted the Miss America winner.

Gary’s instincts also served him very well in his investment business and he credits his success more to his EQ (emotional quotient) than to his IQ (intelligence quotient).

His YouTube journey-

Gary entered the YouTube extremely early.
On May 16, 2006, he started a YouTube channel by name, WineLibraryTV and produced a video almost every day continuously for 5 years.

Now, WineLibraryTV has thousands of videos on different wines.
Even though Gary built a decent following on his YouTube channel; he got his major break only in July 2007, when he was invited to the Conan O'Brien show.

A video in which he made Conan to eat dirt and grass went viral on YouTube and this made him a top 50 followed person on Twitter.
He is also famous for his YouTube channel, GaryVee (has more than 2.4 million subscribers) and also runs #AskGaryVee shows.

Gary also inspires millions around the globe with his YouTube show, DailyVee.
He provides the motivational and educational content for the entrepreneurs and also inspires us to hustle and focus on our goals.

As Gary’s popularity skyrocketed after the Conan O'Brien show, he got invited to the Today show and The Ellen DeGeneres Show.
In 2009, while he was brainstorming for business ideas with his brother, he received an email from ESPN, an American cable sports channel, in that email ESPN asked him to walk to their office and teach them about Twitter.

ESPN was also curious to learn why Gary had more followers than all of the Disney properties combined.
As he was busy, he was unable to check it and by the time he checked his mail at night, he received another email from ESPN, in which ESPN offered to pay him $5,000 for his services.

This earned Gary his first consulting job and he realised that he could start a profitable consulting business.

A great offering from Mark Zuckerberg-

In 2008, Gary published a video on YouTube in which he explained why Facebook should be worried about Twitter.
Thanks to this video, he got invited to give a speech regarding the same topic in Palo Alto.
Later, when Gary completed giving his speech, Mark Zuckerberg popped up from the audience and invited him to the dinner.

In response, he cancelled his flight tonight and accepted Mark Zuckerberg’s invitation.
This helped to cement their relationship and later, when the Mark Zuckerberg’s family was selling the Facebook shares, Mark and his sister Randi emailed Gary to purchase some of them.

Luckily, he saw the potential in Facebook and brought the shares before the Facebook’s IPO (held on May 18, 2012).

The social media mogul-

Gary’s huge social media following made him a social media celebrity and he has over 2.1 million Twitter followers, over 7.3 million Instagram followers and over 3.4 million Facebook fans.
His first investment was in Twitter followed by Tumblr and Facebook.

Later, Gary also invested in Snapchat and Uber.
Whoever invested in Twitter before it went public made a fortune.

Also, Gary’s other early investments in other start-ups reaped him huge profits.
His success can be attributed to his great understanding of the marketing techniques and evolution of the marketing trends.

Gary also knows the important of content and context because only the best story tellers can sell their products in the current times.

Founding VaynerMedia-

In April 2009, Gary co-founded VaynerMedia, a digital marketing agency along with his brother AJ Vaynerchuk.

VaynerMedia is a creative full service digital agency present is different locations like New York, Los Angeles, Chattanooga, London and Singapore and utilises the power of influencer marketing, storytelling and branding.
It is involved with many B2B businesses and extends social media and strategy services to many globally well-renowned companies like Shell, Johnson's, Unilever, Toyota, PepsiCo, General Electric, Hulu, etc.

These brands employ his instinctive knowledge of social media to expand their social media presence and reach to more customers.
Gary’s emotional intelligence and experience with the projects like and Wine Library TV enabled him to take VaynerMedia to great heights.

In 2014, he was ranked number one on Forbes Top 40 Social Selling Market Masters and a year later, he has been titled to Fortune magazine’s 40 under 40 list of the Most Influential Business Leaders.
In 2014, Gary started Vayner/RSE, a venture capital firm by forming a partnership with RSE Ventures Matt Higgins and raised a $25 million investment fund.

In 2016, he founded VaynerSports; it provides full-service athlete representation for the professional players and is located at New York and Sherman Oaks.
In November 2017, Gary also launched his signature sneakers by name The GaryVee 001 & 002s in partnership with K-Swiss, an athletic shoe brand.   

Later, on July 2018, the GaryVee 003s sneakers were launched.
Gary is a 5 time New York Times bestselling author for the books Crush It!: Why NOW Is the Time to Cash In on Your Passion, #AskGaryVee: One Entrepreneur's Take on Leadership, Social Media, and Self-Awareness, Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy Social World and The Thank You Economy.

Now, his current net worth is more than $160 million.

Managing the time efficiently-

Like many successful entrepreneurs, Gary understands the importance of time management and so, he plans his day down to the second.
He makes it sure to not waste even a single minute in his day and so, he even schedules three and four minute meetings.

Almost every day, Gary religiously wakes up early in the morning at 6 a.m.
In his life, he is successful in almost everything but school.

In one of Gary’s talks, he opined that as the school system is built only for the workers, this system is failing the entrepreneurs every single day.

Recognise your strengths and be up to date-

You can only be successful in your career if you make a living on your strengths that is making a career on your strengths but not on weaknesses.
So, you must take time to identify your strengths and if you are unable to do so, you should ask the people closest to you to tell you your strengths and weaknesses.

By doing this, you can save enormous amounts of time by not futilely working forever on your weak spots.
In order to succeed in the current times, we must keep a tab on the evolution of the technologies.

Now, mobile phones are abruptly replacing the televisions in a similar manner in which the televisions replaced the radios.
As many people surf internet on their mobile phones, we must be the best storytellers on this platform in order to attract the attention of the mobile phone users.

This evolution of technology has also changed the face of advertising.
The traditional advertising which bombards us to purchase the products without providing us any real value is now being replaced by the smart advertising which provides us with some value before asking for our money.

In his book, Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy Social World, Gary described the importance of building relationships and providing value before asking for the money.
Essentially, Jab, Jab, Jab, Right Hook refers to give, give, give and ask.

This book also describes the importance of tailoring the content with context for different social media platforms like Facebook, Instagram, Pinterest, Twitter, Tumblr, etc.

His dream-

Gary works very hard and hustles every day to fulfill the dream of owning the New York Jets.
When he first came to America, he struggled to adapt to the American culture and could only speak Russian but not English in Queens and Dover.

Later, when Gary moved to Edison, New Jersey, he became a fan of the New York Jets football team and this was his first ever American thing or connection.
He and his childhood friend Brandon Warnke loved the 1990 Leaf Frank Thomas baseball card.

As everyone around Gary had a New York Jets football team jersey, he too wanted one but unfortunately, his family was too poor to afford an official jersey.
So, his mother knitted one for him with the number 5 on it and it still remains his prized possession and reminds him of his roots.

Later, in his second or third grade, Gary determined that he will grow up from not being able to afford a jersey to owing the whole jets team.
Currently, the New York Jets football team is worth $2.85 billion and is owned by Woody Johnson.
Even today, Gary’s determination drives him every day towards his goal.

He teaches us a very important lesson that we should set ourselves huge goals in order to move forward in our lives.

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