How Gary Vee Escaped The Soviet Union to Conquer The American Dream

From Belarus to the Big Apple: A legendary journey of heart, hustle and hunger

AuthorAuthor

Nigel Thomas & Daniel Bell
March 28, 2024

How Gary Vee Escaped The Soviet Union To Conquer The American Dream

Born in Belarus, Made In New York

“While everybody is hoping and dreaming, I am going to be executing.”

The American Dream used to be the golden ticket to freedom.

Gary Vee is a throwback to the core essence of everything it stands for.

Equality of opportunity available to anyone who puts in the work, regardless of their start in life.

From Belarus to the Big Apple he took life by the horns and conquered the American Dream one gruelling day at a time.

A self-starter who harnessed the power of the internet in its early days to catapult his family's wine business into a $60 million empire.

He is a prestigious keynote speaker and podcast host, as well as the author of a multitude of bestselling books. 

He's also Chairman of VaynerX, the CEO of VaynerMedia, host of #AskGaryVee, and even the creator of VeeFriends, an NFT project. 

Gary's track record speaks volumes about his ability to spot opportunities and turn them into gold.

And how did he reach the upper echelon of entrepreneurship and business development? He hustles and grinds - like a true underdog. 

He uses every waking moment that he can to build his companies and continually search for new investment opportunities.

He earns every inch of ground that he gains and encourages new entrepreneurs to do the same.

But what truly sets Gary apart isn't just his entrepreneurial acumen; it's his unwavering commitment to giving back.

Whether it's through his philanthropic initiatives or his advocacy for aspiring entrepreneurs, he embodies the ethos of lifting others as you climb.

As we delve into the depths of Gary's journey, we'll uncover the secrets behind his meteoric rise, dissect the strategies that propelled him to the summit of success, and glean invaluable lessons that can shape our own entrepreneurial endeavours.

In Gary's world, the entrepreneurial journey is a perpetual adventure, where the only limit is the extent of your ambition.

Proving that in the battle of David versus Goliath, it's not the size of the dog in the fight, but the size of the fight in the dog that matters most.

Today on David to Goliath:

The American Dream

Gary’s story didn't start with silver spoons or trust funds.

It began in 1975 in a world besieged by the shadows of the Soviet Union, where his family faced the unforgiving grip of socialism in Babruysk (now Belarus).

His family bore witness to the struggles of true poverty, their aspirations shackled by the chains of destitution.

At 3 years old, Gary’s family escaped and emigrated to Queens, New York.

Eight souls packed into a cramped studio apartment, facing the harsh reality of immigrant life.

But from these humble beginnings, within that confined space, the family’s spirit burned brightly represented by the torch clutched within the hands of the lady of liberty, just a stone’s throw away.

They’d made it to the land of freedom.

The ideal by which equality of opportunity is available to anyone.

It was time for the Vaynerchuk’s to build the American dream.

His parents epitomized the essence of the underdog, toiling tirelessly to carve out a future from rock bottom.

They showed Gary that dreams weren't made of stardust but of sweat and sacrifice.

What Gary learnt from a young age is that it's not about the hand you're dealt; it's about how you play the cards.

His dad took a job as a stock boy in a liquor store and saved up just enough money to buy his own store in Springfield, New Jersey.

And his mother? A mountain of unwavering confidence.

Instilling in him the deep conviction that dreams were worth chasing, no matter the odds.

“Because of my mother, I’m obsessed with driving self-esteem into my children”.

His childhood became the foundation of his entrepreneurial tendencies.

He was involved in all the activities that any other kid is into – playing sports, and playing outside with friends.

Like many entrepreneurs, school didn't cater to his needs or inspire his creativity.

Instead of feeling fulfilled or motivated, he often found himself suffocated by the rigid structure and outdated curriculum.

He was branded a failure, scoring D’s and F’s on every assignment.

But he wasn't just another face in the crowd. He refused to bow to the allure of empty accolades, rejecting the vanity of a trophy culture.

Instead, he embraced his flaws, wearing them like a badge of honor.

He owned his uniqueness, his DNA pulsating with the rhythm of a young rule breaker.

Outworking his peers with sheer perseverance.

For example: He used to cut the flowers in his neighbours’ yard and sell them back to them for a profit.

Sometimes in life, the man just gotta do what the mans gotta do.

By 7, he would watch as the drivers passed by his lemonade stand on the streets of Queens, not taking any notice.

But getting 95 rejections for every 5 yes’s, he just kept pushing, learning how to deal with rejection head-on.

Then he started a baseball card collector business, earning himself thousands of dollars in just one weekend.

“I was fortunate – I was a failure my whole life,” Vaynerchuk said for The Jakarta Post during the Forward 2019 convention. “When I knocked on doors and asked to wash somebody’s car, 90 out of 95 people said no. When I was still at the lemonade stand, 100 cars would drive by for one that would stop. I was used to failure; it was my foundation, which is why I succeeded.”

By 14, he was drawn into his father’s wine business, assigned to bag ice for $2 an hour.

At 18, a new chapter awaited at Mount Ida College in Newton, Massachusetts.

Here, he discovered the large community of people collecting wines, which ignited a bigger vision.

It was time to step up and put his family's name on the map.

Discovering the Power of The Internet

Fresh out of college in 1998, Gary returned to his hometown, rolled up his sleeves and got to work.

“To me, it’s just binary. You’re either in or you’re out. Every day between seven years-old and 18 years-old I was told that I had already lost, that I was a loser because I failed school. But I knew inside that this was not the game that I was going to play. I was ultimately patient. I made it work.”

Taking the reins of his father's liquor store, Shoppers Discount Liquors, he dove in headfirst.

College taught him to think bigger. 

He took it upon himself to transform this local liquor store into an industry Goliath.

He envisioned a nationwide empire – a network of brick-and-mortar stores that would redefine retail as we knew it.

But amidst the clinking of glasses and the whispers of success, with street smarts far beyond his years, he observed a huge untapped opportunity.

The internet - he saw something others did not and he was ready to go all-in.

One egg. One basket.

He renamed the business to Wine Library and launched WineLibrary.com.

“I launched a website [and in] 1996-97 -- launching a website was like me telling you right now I am going to Mars and starting a virtual reality studio. It was very far-fetched for a single store liquor store to have a need for a website. I launched an email newsletter in 1997. In ‘97, email was novel. people were not getting emails to buy stuff, I was doing that.”

This pioneered online sales in the realm of alcohol - the first of it’s kind.

Long before email marketing was common place, Gary found creative ways to market Wine Library and draw audiences to his site.

He would email weekly discounts and share his favourite wine recommendations - what today we know as Newsletters.

Within the span of five years, sales skyrocketed from $3 million to a staggering $60 million annually.

There were sleepless nights, moments of doubt, and hurdles that seemed insurmountable.

But there was one thing that made all this possible.

With a stroke of genius, he went against the grain and unleashed his best idea yet.

For the very first time, the face and voice of Gary Vaynerchuk were about to become synonymous with a new era of business.

Wine Library TV – YouTube

Gary has never been one to let the noise of other people's opinions drown out his own inner voice.

“For 18 months, I did my show five days a week and nobody gave a shit. I had 30 to 75 views on every video for an entire year.”

At the time YouTube was the place people escaped their work day to watch funny cat videos, parodies and it certainly wasn’t a place to do business.

Gary had other ideas though…

In 2006, he went against the grain and married entertainment and education into a new show called Wine Library TV.

He leveraged his:

  • Unmatched knowledge of wines

  • His energetic personality

  • His consistent daily hustle

To create a show which was the first of its kind.

Publishing over 1000 episodes he skyrocketed the show’s viewership over five grueling years.

“You’re going to look for that one move that’s going to change your career and you’re going to continue to search, and search and search and never do. You’ll be looking for the hacks, and the shortcuts and the easy way out and I’ll just keep putting in the work, the hours, the long term value, the strategy and the patience.”

Gary didn't just preach to the choir either; he listened.

Probably his greatest strength.

Every episode was a chance to hone his craft.  

He paid attention to what his audience craved, adapted and then delivered.

The show became so popular that he even appeared on NBC’s “Late Night With Conan O’Brien,” teaching the host about wine.

His sheer perseverance and self belief turned Wine Library from a local liquor store into a $60 million a year Goliath.

But above all else, it showed him the power of monetizing social media, at a time when everyone else was laughing at the very concept.

“I said, ‘My God, I am a 33-year-old businessman, I have only been in the wine business, I used the internet to build my wine business, but now people are driving four hours to Wine Library just to shake my hand because they like my show, and they are buying wine -- this is weird.'"

Today we all have someone to model off for building a personal brand. But back then Gary only had himself. A true trailblazer, pioneering the path for others to follow.

Silencing the doubters one episode at a time he took a huge risk and got first movers advantage.

He didn’t just focus on YouTube though. He spent hours and hours engaging with his audience through Twitter and became one of the most followed accounts at the time.

Then, in 2008, his big moment arrived. 

He brought greatness into the light during a show-stopping keynote at Web 2.0 in New York City, and solidified his position in the mainstream.

As people started copying his strategies he knew he had to adapt.

“You always squeeze the f*ck out of an orange that’s full. And when it’s empty, you find a pear, which is harder to squeeze but you hope a grapefruit comes along. Email used to be 90% opening rates for me. It’s not anymore. Google adwords used to be 5 cents a click. It’s not anymore.”

So in 2011, after airing 1,000 episodes of Wine Library TV, Gary ended both the show and his engagement with the family business to move in a new direction.

It was time to utilize his unique understanding of the digital landscape to help other businesses migrate into the online world.

A new age of marketing agencies was about to begin.

Once again, Gary pioneered the path for others to follow.

VaynerMedia

After dramatically growing Wine Library online, Gary knew it was time to cash in on this media wave.

This time though, by helping other companies through a digital marketing agency that he started with his brother AJ.

VaynerMedia was born.

“8 years ago no one would even talk to me about social media and marketing. About building a creative agency. About building a personal brand. It doesn’t matter if you come from non-profit, or art or philanthropy or selling sneakers, the market can’t deny your results. And so even though I started my career in wine, no one could dispute my success when I started to win. You’ve got one life, forget about where you came from and focus on where you want to be.”

He positioned himself at the forefront of the digital revolution and began offering services including:

  • Strategy

  • Creative

  • Paid media 

  • Production

  • Influencer programs

Producing content for the brands to ‘sell stuff through the phone’, revolutionising the way they connect with their audience.

“What Vaynermedia does is, we are just a modern day Madison Avenue agency. We make videos and pictures, we are running media dollars for the biggest brands in the world, helping them storytell and make business results on Facebook, on Instagram, on Snapchat, YouTube, podcasting, Alexa.”

Gary wasn't just the face of the agency; he always got stuck in the trenches.

Being the driving force behind every strategy, every campaign, and every success story.

The VaynerMedia story wasn't paved with gold from the start, however.

A series of poor financial decisions meant Gary and AJ had no financial backing to get VaynerMedia off the ground.

“I was worthless to the bank”.

They had no choice but to set up shop in a borrowed conference room where they’d regularly manifest their dreams. Taking raw action to force them into existence.

However what they did know from the Wine Library days is that attention is the currency of the digital age, and they relentlessly pursued it across every platform imaginable.

First, it was Google AdWords, then it was Facebook Ads, then Twitter, then Instagram, Snapchat, YouTube, and the list goes on and on.

In 6 years, the agency grossed $100 million in revenue, had five offices worldwide, and grew from 30 employees to total of 1000 employees in 2019.

They were also named one of Ad Age's A-List agencies.

One of their biggest success stories the iconic Budweiser ad,"Harry Caray's Last Call". 

A marketing masterpiece that captured the hearts of millions and won YouTube Ad of the Year.

The advertisement showed Chicago Cubs fans who were anxiously watching on to see if their team would win the World Series, a legendary throwback from sportscaster Harry Caray’s who predicted back in 1991: “Someday the Chicago Cubs are going to be in the World Series."

The company, born from nothing, became a hotbed of innovation.

Through his unique personality, Gary actively empowers his employees to be themselves. He champions the weird and wacky ways of each and every person in his tribe.

It became a sanctuary for dreamers, a playground for pioneers, a canvas for creators.

As word spread their A-list client roster gained more and more household names.

From General Electric to Pepsi-Co, Fortune 500 clients to this day entrust their dreams to VaynerMedia, knowing that here, magic happens.

But Gary was still yet to see the full power of his personal brand.

The Power of Personal Branding

As you probably know by now Gary champions the internet and social media as the greatest land grab of opportunity in human history.

“I am thinking about content 24/7 the same way that someone is deeply religious.”

Whilst many businesses still frown upon creating content on platforms their kids use, the tide is starting to turn - and we’re not going back.

Gary stands as a titan of content creation, wielding his platforms to churn out daily doses of motivation that cut through the noise like a sharpened blade.

From the trenches of entrepreneurship to the peaks of happiness, he fearlessly tackles every subject under the sun.

“30 was the year I decided that I was going to become GaryVee. That I was going to live my life in the pursuit of my ambition. That I would not waste another moment on anything but my dream.”

Whilst some critique the perfection of his work what cannot be argued is the sheer amount of volume and feedback he amasses by just taking raw relentless action.

Others wait around for the perfect moment - Gary on the other hand just holds up the camera, talks, and posts.

A great example of this is TikTok. Whilst seasoned business owners laughed at funny dances and viral clips for teenagers Gary jumped on the train early doors and has now amassed over 15 million followers.

To take things to the next level back In 2014, he built his own personal content production team and started a daily YouTube show called The #AskGaryVee Show.

With each episode, he tackles questions from the masses, infusing his responses with raw authenticity and boundless insight about everything from business to life hacks to figuring out success.

Through his relentless pursuit of truth, he has ignited a fire within countless souls, compelling them to rise from the ashes of complacency and embrace their uniqueness.

“I’ve always credited the success of that venture to my hustle and single-minded dedication to engaging with my fans and customers by answering every email or blog comment I received and going overboard to show my appreciation for their business.” 

He also runs DailyVee, an online documentary series. 

Here, he invites us into the inner sanctum of his life, blurring the lines between CEO and internet personality with grace.

Through the lens of his camera, we witness the uncut life of an entrepreneur in its naked entirety – from the boardrooms of power to the quiet solitude of introspection. And EVERYTHING in between.

Whether it's navigating client meetings, fostering employee camaraderie, or imparting financial advice, Gary's authenticity shines through as a beacon of authenticity.

A few examples of his viral YouTube videos include “My 5 Biggest Failures in Business” and “How to Find Your Path to Happiness.”

His content centres around 4 pillars:

1. Authenticity and Relatability: Through raw vulnerability and unabashed honesty in a world inundated with polished facades, Gary's authenticity is a timely reminder that true success is born from the crucible of hard work and determination.

2. Focus on Taking Action: This isn't just a mantra for Gary; it's a way of life. He urges his audience to push beyond their limits, to embrace discomfort, and to pursue their dreams with the underdog spirit.

3. Emphasis on Customer Experience: By placing the customer at the heart of his endeavours, he has cultivated a loyal following that transcends transactions, forging bonds that withstand the test of time. 

4. Free Thinking: For Gary, content is his way of seeing the world through a lens of endless possibility. He challenges us to think differently, to question the status quo, and to explore new horizons with curiosity.

And now videographers, social media specialists, and graphic designers help amplify his voice on multiple social media platforms with a 30 person team.

He’s tapping into all 4 forms of leverage (people, finance, software and media) to have a huge competitive advantage.

Yet, living so publicly online comes with its own set of challenges.

Every comment, every critique, every whisper of doubt becomes magnified in the echo chamber of social media.

But Gary, undeterred by the haters accepts it’s a sacrifice he’s willing to make and leads with empathy.

“The game is my life. There will never be a moment to quit. There’s no dollar amount. Nothing you can do to make me stop. The process, the journey and the hustle is the drug that drives me. It’s my oxygen. It’s what I love, and so every day is going to be the same. 24/7–365.”

He’s potentially the first person to document his life to this degree, which has prompted many other entrepreneurs to follow his lead to promote their own companies.

Then there’s The Gary Vee Audio Experience – a podcast where he’s maximizing the art of repurposing content.

In over 300 episodes, he’s weaved together #AskGaryVee segments, keynote speeches, entrepreneurial advice, and intimate fireside chats.

Ensuring that whether his audience prefers to watch, listen or read, he’s got a medium just for them.

And maximizing the reach of every piece of content produced.

To show just how powerful all this online attention is, he’s been presented with huge opportunities that others would not.

As the face of K-Swiss in 2017, his partnership contributed to a $200 million-plus exit in 2019.

And a sought-after speaker, he now commands fees as high as $100,000 per presentation.

Not bad for an hours work!

But just how lucrative is the influencer economy? 

According to Captiv8, a data-driven influencer marketplace, a person with 100,000 followers could earn an average of $5,000 per Instagram post, and $12,000 on YouTube. If you bump the follower count up to 500,000, the prices for Instagram rises to an average of $10,000 per post and potentially $25,000 on YouTube.

And remember: Half the world isn’t even online yet.

Although the competition is getting more fierce by the day.

So to stand out here are Gary’s 5 key tips to help make it as an influencer today:

1. Love your content: “Make content that you are passionate about because you need to make a lot of it and if you do not love what you are doing, you will quit.”

2. Hashtagging is key: “Hashtags. If I want to talk about wine, when I post my wine post, in my comments I leave hashtags for cabernet, merlot, chardonnay, Napa Valley, Duckhorn ... do the whole thing.”

3. Engage: “Dollar 80 strategy. Leave your two cents on 90 posts a day on Instagram -- which means you have deposited a $1.80.”

4. Collaborate: “Spend an hour DMing and saying, ‘How can I bring you value?’”

5. Be patient: “The most important ingredient is patience ... either you are unbelievably charismatic and talented, which is .001 percent ... or you out-will and outwork and are strategic and put in the patience.”

Today Gary’s presence is undeniable across all the main social platforms and a true testament to the mindset of not just showing up for one day but everyday - for years on end.

But behind all the success, there’s one thing that keeps his fire burning.

Kindness.

Before we get to that we need to confront the elephant in the room.

The Misunderstood Pursuit of Buying The New York Jets

This is the long, long game. I’m driven by the climb. It could be because I’m an immigrant and I just have this chip on my shoulder. Or Maybe it’s in my DNA. I don’t like winning. I like losing. I like the struggle. I like people telling me that I can’t.

Gary’s net worth is estimated to be around $200 million.

He has become an angel investor, grabbing stakes in big tech companies such as Facebook, SnapChat, Tumblr, and Twitter early on.

Those investments didn't fall into his lap. He spotted opportunities, he took risks, and he seized the moment when others hesitated.

Common knowledge is that he aspires to one day own the New York Jets.

But that’s a huge misconception.

He’s already achieved his bucket list dream. That bucket list dream was to be in pursuit of buying the NY Jets, not just owning them.

“The reason I am a happy person is because I know I was happy with nothing.”

It’s about the journey, not the destination.

Too often, we get caught up in thinking that success is a finish line we'll cross one day.

Success isn't a final; it's constant.

It's about waking up every day and giving it everything you've got. It's about loving the climb, not just reaching the summit.

Forget about the endgame. Forget about the Jets. What matters is that fire in your belly, that drive pushing you forward, day after day.

“I can see why it’s easy to think like that after listening to business success stories, but you have to understand that picking out these pivotal moments is all hindsight, not foresight. Sure, it’s cool to hear successful business speakers recount how they “made it” and it may even be a little helpful if you can relate. But the truth is, having the mindset that the “made it” moment is the finish line to your goal, will only prevent you from pushing yourself further.”

That is winning the game - being able to play it until the day you die.

To Gary, what matters is that he’s on the path, that he’s hustling every single day to be the best version of himself.

Even if he does buy the New York Jets someday, it doesn’t mean he’s cashing in on his retirement plan.

What it means is that there’s a whole lot more work to be done, and that’s the part that excites him most.

Amidst the millions flowing into his ventures, he champions an underestimated currency: kindness.

The pursuit of kindness is the golden thread weaving through the tapestry of his life.

It inspires him to pursue his passions endlessly, keeping the flame of entrepreneurship ablaze within him.

Despite now rubbing shoulders with A-listers, he remains tethered to his origin story, honoring the gifts bestowed upon him by his mum and dad, and sharing them generously with the world.

His experience demonstrates that the American Dream still exists for those who choose execution over excuses.

“I’m just getting started. It doesn’t matter who you are, where you’re from or what you did before now. Each day is an opportunity to deploy your time and energy toward your dream. Think about what you want, reverse engineer that, and then execute.”

It's a reminder that greatness isn't reserved for the chosen few; it's there for anyone willing to bleed for it.

In essence, Gary’s journey is now about inspiring others to find joy in their passions, to cultivate kindness amidst success, and to embrace the pursuit of excellence as a way of life.

We hope his story inspires you to believe that anything is achievable with the right mindset.

And who knows? The next lemonade stand might just be your ticket to your destiny.

David to Goliath Action Items:

Personal Branding: If Gary’s story isn’t a big enough reason to show the power of personal brands online I don’t know what is. If you think you’re too late to the party, you’re wrong. Only half the world is online and for the half that is, only 1% consistently post content. The best time to start was 10 years ago but the next best time is now!

Listen and Watch: Whilst most people associate Gary Vee with just taking action his best skill is arguably listening and watching - so he can capitalize on gaps in the market. You have 2 ears and 1 mouth for a reason - use it to your advantage!

Understand Attention: It doesn’t matter what platform you use, the foundation of getting attention is always the same. It’s about understanding the core underlying principles of human psychology. If you want to learn more I just wrote a huge article on how to get attention filled with examples and action items.

Repurpose Content: You only have 24 hours in the day so you must be strategic. The reason why big creators like Gary pump out so much content is that they create one piece and then distribute it using systems across other platforms. So for every 1 piece of content, they’re in fact creating 20.

Win The Game by Playing: Time and time again you see Olympians get their gold and then fall into a deep state of depression. Luckily, business is one of the only sports you can play for your entire life and the way to win is by playing longer than everyone else. Remember: Success is the journey, not the destination.

I was born in the UK but luckily got the chance to work and live in the U.S. (and hopefully I’ll be back soon!).

Researching and writing about Gary’s story reminded me again of just what an incredible country the United States of America is.

So whilst people complain and the country is divided in yet another political campaign let’s remind ourselves of what made this country great.

The American Dream.

The land of opportunity.

The chance for anyone despite their background to make something out of nothing.

That in my humble opinion is a cause worth fighting for.

So keep dreaming like a Giant.

But fight and believe in your dreams like a God damn Underdog baby!

Yours truly,

-Nigel Thomas

P.S. Whenever you're ready, there are 4 ways I can help you:

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