Gary Vaynerchuk sat alone in a basement with a camera pointed at him, three bottles on the table, and a spit bucket sitting beside them. No lighting. No script. Just Gary talking about wine like it was baseball cards and sports teams, cuss words and all.

The wine world thought it was a joke.

Gary used that basement show to grow a $3 million family liquor store to a $60 million brand, while building one of the biggest independent ad agencies in the world.

In today's newsletter, I share Gary's basement story as well as:

Enjoy riding Gary V's Big Wheel to the big time…LG

P.S. And if you want to be a better storyteller, Gary is one of the best to study

Gary Vaynerchuk (Gary V) and his parents emigrated to America from the Soviet Union when he was 3 years old.

Nine of them shared a studio apartment in Queens. Aunts, uncles, grandparents, kids all living in one room. His father took a job as a stock boy in a New Jersey liquor store and saved every dollar he did not have to spend.

Then the family made it to Edison, New Jersey. A yard. A street with other kids on it. They were still ridiculously poor, but to Gary, this was arrival. He was becoming Americanized.

Gary wanted what every kid in Edison had. An official New York Jets jersey. His family could not afford the $40.

So his mother made him one by hand. She stitched his name across the back and gave him the number '5'.

Gary wore it every day. The real one was out of reach, but the one his mother made lit a decision. He was going to own the entire team someday. Not a ticket. Not a seat. The franchise.

THE PUREBRED

Now on a mission, Gary launched his first venture in elementary school, picking flowers from neighbors' yards and selling them to strangers on the street.

He soon turned his sights to something with more potential. Lemonade. Not a stand. A network. He franchised out as many as 8 of them across Edison, recruited his friends to work them, and rode his Big Wheels from corner to corner collecting the cash.

By 12 he had moved into higher margins. Baseball cards, G.I. Joes, Garbage Pail Kids. He worked the mall trade shows on weekends and pulled $2,000 to $3,000 in a single weekend. He set his sights on becoming the biggest baseball card seller of all time and had $10,000 stashed under his bed as his seed fund.

A DREAM CRUSHED

His grades had already collapsed, by choice. School was never a game he planned to win so he just succomed to the working all the time.

THE SWITCH FLIPS

At 16 they let him upstairs to work the floor.

He was not into wine. He had no passion for it. It was the thing that had replaced the thing he loved.

Then the wine of the year, the Caymus Special Select, sold out. Customer after customer walked in asking for it, and walked back out when they heard it was gone. Gary watched the sales leave through the front door.

The store had no back-order system. Gary decided to build one on the spot so that the next customer asked for the Caymus, Gary could say they were sold out, but he could take a back order.

The first time this happened a man said he wanted six cases.

Gary figured the guy was an alcoholic and asked, “Are you having a party?”

“No,” the man said. “I collect wine.”

Something clicked.

Gary knew collectors. He had been one, and he had sold to a thousand of them at card shows. The scarcity. The obsession. The willingness to pay a premium. The thrill of the hunt.

Baseball cards and wine were the same behavior wearing different clothes.

In that moment, Gary's perspective on wine completely changed as did his passion for it. He read everything. Vintages, regions, winemakers. He started selling wine the way he had sold cards.

THE ADULT THEME PARK

The summer he finished college, Gary took over the store. At the time, it was doing about $3 million a year.

He renamed the store from “Shoppers Discount Liquors” to “Wine Library.” He nixed the discount positioning by expanding the assortment and improving the in-store experience.

His idea centered on framing it as an adult theme park for wine.

Next he looked at the internet and saw what almost no one selling wine had seen yet. He built one of the first liquor e-commerce sites in the country and was among the first handful of stores to run email marketing.

Then he started telling stories to help move the wines. When a winemaker left a prestigious label such as Opus One and started their own brand, those wines had no ratings and did not sell well because the whole industry ran on numbers.

“This is a winemaker from the wine that is getting the best scores in the world that's a $100. He has just left and started his own brand with his name on it and is selling it for half the price! Buy it now before it becomes this.”

That was the edge. As he put it:

“My ability to tell a better story than my competitors became the reason we had a successful company.”

He grew the store from $3M to $60M in roughly 7 years.

A CAMERA, SPIT BUCKET & JETS JERSEY

The year he turned 30, Gary sent someone on his team to Best Buy to grab a Canon video camera. He picked 3 bottles, set them on a table, hit record, and reviewed them. The first episode covered 3 wines from a small California label called Verite.

He called the show Wine Library TV and posted it on YouTube.

IIt was the exact opposite of every wine expert alive.

For the first 18 months he shot the show 5 days a week, and almost no one watched. No viral moment. No overnight audience. A guy in a basement, a camera, and 3 bottles, over and over.

He kept going anyway. The reps were the strategy. He was betting that video was where wine was headed even though no one else in the wine industry felt the same.

THE EPISODE THAT CHANGED EVERYTHING

Then came episode 58. Before it, Gary was a business operator trying to host a wine show. This time he leaned all the way into the anti-gatekeeper posture.

He pushed viewers to trust their own palate, talked like a sports fan rather than a sommelier, and made wine feel like something regular people could enjoy without asking permission from critics.

Around the same time, he turned down 2 network TV offers. He was done performing a polished business version of himself.

Within about a year, 25,000 people a day were watching. Soon it was 100,000.

They were not only wine drinkers. Tech people. College kids. Senior executives, including a wave of them from companies like Hewlett-Packard, drawn to the fact that he was not selling them anything but the truth.

They gave themselves a name. Vayniacs. They commented, shared, showed up, and bought. He had not built an audience. He had built a community with his name on it.

A BORROWED CONFERENCE ROOM

Then he took it to a stage. A keynote at a big web conference in New York, where he put his immigrant story, his wine numbers, and his conviction about social media in one place. One outlet called him the most animated and lively speaker of the day.

That talk became a 7-figure, 10-book deal with a major publisher. His first business book, Crush It!, followed. A New York Times bestseller.

He was betting his whole future on the internet while the advertising industry rolled its eyes.

The year after the keynote, Gary started VaynerMedia with his younger brother AJ.

They had no outside funding. They had no office. Gary had no money for rent, so they ran the company out of a borrowed conference room at another company.

The pitch was simple. Do for other brands what he had done for Wine Library.

30 people the first year. Then the client list started reading like the Fortune 500: PepsiCo, GE, Johnson & Johnson, Chase, AB InBev.

FROM THE BASEMENT TO MADISON AVENUE

5 years and 1,000 episodes after that first video made in the basement, he shot the last one (🍷 has since been reborn).

He stepped back from running Wine Library day to day and pointed everything at the agency. The wine show that started in a basement had done its job. It built the audience, the voice, and the proof that the whole thesis worked.

By now the brand was bigger than the store. A second book, The Thank You Economy, landed on the bestseller list. The keynotes kept coming.

The wine chapter was closed. Now it was about building the Gary V brand.

Today Gary is Chairman of VaynerX and CEO of VaynerMedia, a global operation with offices that have spanned New York, Los Angeles, London, Tokyo, Singapore, and Mexico City. His companies pull in over $200M in annual revenue. He has 50 million followers, has authored 8 books, 6 of them New York Times bestsellers, and ships roughly 100 pieces of content a day.

Gary treats his own life like inventory. The parts that looked worthless (the poverty, the failing grades, the homemade jersey, the $2 an hour) turned out to be the parts that sell. He found the value in his story where no one else was looking, and he told it before it got expensive.

#1. Embrace the Underdog

Gary never tried to make Wine Library TV look bigger than it was. He leaned into the basement, the cheap camera, the spit bucket, and the Jets energy. The rough setup became part of the charm. Same thing with his poor upbringing and homemade jersey.

ACTION: Find the least impressive fact about where you started. The apartment, the rejection, the job you hated. Put it in the first ten seconds of your founder story instead of hiding it in the middle.

#2. Be the Opposite of the Room

Every wine expert was formal, careful, and intimidating. Gary wore a Jets jersey, spit into a football bucket, and told people to trust their own palate. He did not try to out-expert the experts. He became their opposite.

ACTION: Write down how everyone in your category tells their story: the tone, the words, the uniform. Then build yours as the deliberate opposite, so a stranger can spot you in one sentence.

#3. Turn Customers Into Champions

Gary did not just build an audience. He built the Vayniacs, a community that felt like the inner circle and spread his message for free. He answered them by name, showed up for them daily, and did unscalable things that made people feel seen. They carried his story further than any ad could.

ACTION: Pick one customer and do something for them that does not scale and that no one would expect. Build a moment worth retelling, and let them carry your story further than you can.

Bonus Tip: Gary V's #1 Storytelling Skill

Belief. Not in wine, in himself. Gary stepped to the mic before anyone was listening and said the internet was the future, and kept at it over and over. 1,000 basement episodes, no scripts, no polish, just a guy certain enough about his own story to keep telling it until the world caught up. That self-belief gave his content its pull. It sold more than wine. It sold Gary.

ACTION: Before you worry about how to tell your story, get certain that you believe in it, and in yourself telling it. The conviction is what people actually feel, and it is what makes them lean in.

From followers to exits, Gary V's footprint is enormous:

The wine world thought it was a joke.

Gary used that basement show to grow a $3 million family liquor store to a $60 million brand, while building one of the biggest independent ad agencies in the world.

In today's newsletter, I share Gary's basement story as well as:

Enjoy riding Gary V's Big Wheel to the big time…LG

Gary Vaynerchuk (Gary V) and his parents emigrated to America from the Soviet Union when he was 3 years old.

Nine of them shared a studio apartment in Queens. Aunts, uncles, grandparents, kids all living in one room. His father took a job as a stock boy in a New Jersey liquor store and saved every dollar he did not have to spend.

Then the family made it to Edison, New Jersey. A yard. A street with other kids on it. They were still ridiculously poor, but to Gary, this was arrival. He was becoming Americanized.

Gary wanted what every kid in Edison had. An official New York Jets jersey. His family could not afford the $40.

So his mother made him one by hand. She stitched his name across the back and gave him the number '5'.

Gary wore it every day. The real one was out of reach, but the one his mother made lit a decision. He was going to own the entire team someday. Not a ticket. Not a seat. The franchise.

THE PUREBRED

Now on a mission, Gary launched his first venture in elementary school, picking flowers from neighbors' yards and selling them to strangers on the street.

He soon turned his sights to something with more potential. Lemonade. Not a stand. A network. He franchised out as many as 8 of them across Edison, recruited his friends to work them, and rode his Big Wheels from corner to corner collecting the cash.

By 12 he had moved into higher margins. Baseball cards, G.I. Joes, Garbage Pail Kids. He worked the mall trade shows on weekends and pulled $2,000 to $3,000 in a single weekend. He set his sights on becoming the biggest baseball card seller of all time and had $10,000 stashed under his bed as his seed fund.

A DREAM CRUSHED

His grades had already collapsed, by choice. School was never a game he planned to win so he just succomed to the working all the time.

THE SWITCH FLIPS

At 16 they let him upstairs to work the floor.

He was not into wine. He had no passion for it. It was the thing that had replaced the thing he loved.

Then the wine of the year, the Caymus Special Select, sold out. Customer after customer walked in asking for it, and walked back out when they heard it was gone. Gary watched the sales leave through the front door.

The store had no back-order system. Gary decided to build one on the spot so that the next customer asked for the Caymus, Gary could say they were sold out, but he could take a back order.

The first time this happened a man said he wanted six cases.

Gary figured the guy was an alcoholic and asked, “Are you having a party?”

“No,” the man said. “I collect wine.”

Something clicked.

Gary knew collectors. He had been one, and he had sold to a thousand of them at card shows. The scarcity. The obsession. The willingness to pay a premium. The thrill of the hunt.

Baseball cards and wine were the same behavior wearing different clothes.

In that moment, Gary's perspective on wine completely changed as did his passion for it. He read everything. Vintages, regions, winemakers. He started selling wine the way he had sold cards.

THE ADULT THEME PARK

The summer he finished college, Gary took over the store. At the time, it was doing about $3 million a year.

He renamed the store from “Shoppers Discount Liquors” to “Wine Library.” He nixed the discount positioning by expanding the assortment and improving the in-store experience.

His idea centered on framing it as an adult theme park for wine.

Next he looked at the internet and saw what almost no one selling wine had seen yet. He built one of the first liquor e-commerce sites in the country and was among the first handful of stores to run email marketing.

Then he started telling stories to help move the wines. When a winemaker left a prestigious label such as Opus One and started their own brand, those wines had no ratings and did not sell well because the whole industry ran on numbers.

“This is a winemaker from the wine that is getting the best scores in the world that's a $100. He has just left and started his own brand with his name on it and is selling it for half the price! Buy it now before it becomes this.”

That was the edge. As he put it:

“My ability to tell a better story than my competitors became the reason we had a successful company.”

He grew the store from $3M to $60M in roughly 7 years.

A CAMERA, SPIT BUCKET & JETS JERSEY

The year he turned 30, Gary sent someone on his team to Best Buy to grab a Canon video camera. He picked 3 bottles, set them on a table, hit record, and reviewed them. The first episode covered 3 wines from a small California label called Verite.

He called the show Wine Library TV and posted it on YouTube.

IIt was the exact opposite of every wine expert alive.

For the first 18 months he shot the show 5 days a week, and almost no one watched. No viral moment. No overnight audience. A guy in a basement, a camera, and 3 bottles, over and over.

He kept going anyway. The reps were the strategy. He was betting that video was where wine was headed even though no one else in the wine industry felt the same.

THE EPISODE THAT CHANGED EVERYTHING

Then came episode 58. Before it, Gary was a business operator trying to host a wine show. This time he leaned all the way into the anti-gatekeeper posture.

He pushed viewers to trust their own palate, talked like a sports fan rather than a sommelier, and made wine feel like something regular people could enjoy without asking permission from critics.

Around the same time, he turned down 2 network TV offers. He was done performing a polished business version of himself.

Within about a year, 25,000 people a day were watching. Soon it was 100,000.

They were not only wine drinkers. Tech people. College kids. Senior executives, including a wave of them from companies like Hewlett-Packard, drawn to the fact that he was not selling them anything but the truth.

They gave themselves a name. Vayniacs. They commented, shared, showed up, and bought. He had not built an audience. He had built a community with his name on it.

A BORROWED CONFERENCE ROOM

Then he took it to a stage. A keynote at a big web conference in New York, where he put his immigrant story, his wine numbers, and his conviction about social media in one place. One outlet called him the most animated and lively speaker of the day.

That talk became a 7-figure, 10-book deal with a major publisher. His first business book, Crush It!, followed. A New York Times bestseller.

He was betting his whole future on the internet while the advertising industry rolled its eyes.

The year after the keynote, Gary started VaynerMedia with his younger brother AJ.

They had no outside funding. They had no office. Gary had no money for rent, so they ran the company out of a borrowed conference room at another company.

The pitch was simple. Do for other brands what he had done for Wine Library.

30 people the first year. Then the client list started reading like the Fortune 500: PepsiCo, GE, Johnson & Johnson, Chase, AB InBev.

FROM THE BASEMENT TO MADISON AVENUE

5 years and 1,000 episodes after that first video made in the basement, he shot the last one (🍷 has since been reborn).

He stepped back from running Wine Library day to day and pointed everything at the agency. The wine show that started in a basement had done its job. It built the audience, the voice, and the proof that the whole thesis worked.

By now the brand was bigger than the store. A second book, The Thank You Economy, landed on the bestseller list. The keynotes kept coming.

The wine chapter was closed. Now it was about building the Gary V brand.

Today Gary is Chairman of VaynerX and CEO of VaynerMedia, a global operation with offices that have spanned New York, Los Angeles, London, Tokyo, Singapore, and Mexico City. His companies pull in over $200M in annual revenue. He has 50 million followers, has authored 8 books, 6 of them New York Times bestsellers, and ships roughly 100 pieces of content a day.

Gary treats his own life like inventory. The parts that looked worthless (the poverty, the failing grades, the homemade jersey, the $2 an hour) turned out to be the parts that sell. He found the value in his story where no one else was looking, and he told it before it got expensive.

#1. Embrace the Underdog

Gary never tried to make Wine Library TV look bigger than it was. He leaned into the basement, the cheap camera, the spit bucket, and the Jets energy. The rough setup became part of the charm. Same thing with his poor upbringing and homemade jersey.

ACTION: Find the least impressive fact about where you started. The apartment, the rejection, the job you hated. Put it in the first ten seconds of your founder story instead of hiding it in the middle.

#2. Be the Opposite of the Room

Every wine expert was formal, careful, and intimidating. Gary wore a Jets jersey, spit into a football bucket, and told people to trust their own palate. He did not try to out-expert the experts. He became their opposite.

ACTION: Write down how everyone in your category tells their story: the tone, the words, the uniform. Then build yours as the deliberate opposite, so a stranger can spot you in one sentence.

#3. Turn Customers Into Champions

Gary did not just build an audience. He built the Vayniacs, a community that felt like the inner circle and spread his message for free. He answered them by name, showed up for them daily, and did unscalable things that made people feel seen. They carried his story further than any ad could.

ACTION: Pick one customer and do something for them that does not scale and that no one would expect. Build a moment worth retelling, and let them carry your story further than you can.

Bonus Tip: Gary V's #1 Storytelling Skill

Belief. Not in wine, in himself. Gary stepped to the mic before anyone was listening and said the internet was the future, and kept at it over and over. 1,000 basement episodes, no scripts, no polish, just a guy certain enough about his own story to keep telling it until the world caught up. That self-belief gave his content its pull. It sold more than wine. It sold Gary.

ACTION: Before you worry about how to tell your story, get certain that you believe in it, and in yourself telling it. The conviction is what people actually feel, and it is what makes them lean in.

From followers to exits, Gary V's footprint is enormous:

The best way to understand Gary's storytelling is to watch him work. These 3 clips show three different sides of his skill: how he turns customer service into a story, how he uses one childhood object to explain his ambition, and how he delivers motivation with speed and force.

#1. “The Jay Cutler Story”. Gary turns a small customer order into a story people remember. The lesson is not the jersey. It is how he makes customer care feel personal, specific, and worth repeating.

Watch here😀

#2. “Gary Vaynerchuk and the New York Jets”. Gary uses one homemade jersey to explain his whole life arc. Watch how a small childhood object becomes the symbol for his drive, identity, and long-term ambition.

Watch here: 

#3. “Give me 58 sec..I'll CHANGE your life FOREVER”. In less than a minute, Gary shows why urgency is part of his brand. Fast, blunt, emotional, and built to move people.

Watch here: 

Gary is a walking storytelling workshop because he understands what it takes to pull people inside his convictions and make them feel what he believes.

Need help with your story? I got you.

Send an email to [email protected] and someone from my team will circle back with you.