GARY VAYNERCHUK: The ability to understand yourself leads to incredible happiness.

KATE: Get ready for this high octane, serial entrepreneur with a gift for getting attention.

GARY: Subscribe.

(making noises) KATE: A marketing mogul who has achieved success beyond his wildest dreams.

An immigrant from Belarus who started small, at his family's liquor store.

And with spot on gut instincts, converted his humble beginnings to staggering success.

GARY: I, even at 22, thought I had something special.

KATE: You did?

GARY: I did.

KATE: And what was it that you thought was special?

GARY: That I saw things differently.

KATE: Today, Gary Vaynerchuk is taking me to his favorite restaurant.

One of the oldest running taverns in New York City.

White Horse Tavern, huh?

GARY: Iconic.

KATE: We're hearing the full story of how Gary Vaynerchuk, now known simple as GaryVee, has become one of the most intriguing entrepreneurs of our time.

A visionary who helms his own media empire.

And who works tirelessly to promote empathy and self-awareness as the ultimate keys to the American dream.

GARY: I believe, very deeply, that it is not how much money you make.

It's how you make it.

♪ KATE: What's better in life than a bottle of wine, great food and an amazing conversation?

My name is Kate Sullivan and I am the host of To Dine For .

I'm a journalist, a foodie, a traveler, with an appetite for the stories of people who are hungry for more.

Dreamers.

Visionaries.

Artists.

Those who hustle hard in the direction they love.

I travel with them to their favorite restaurant, to hear how they did it.

This show is a toast to them and their American dream.

KATE: To Dine For with Kate Sullivan is made possible by... ♪ ANNOUNCER: There are people in your life who count on you for what matters most.

American National agents are close to home and committed to our communities.

They'll help you find the right coverage for you, your family, even your farm and business.

You can learn more at americannational.com.

KATE SULLIVAN: Today I'm in Greenwich Village on my way into the iconic White Horse Tavern.

I'm meeting one of the most successful and dynamic businessmen of our time.

He chose the White Horse Tavern as his favorite spot in New York City, and I can't wait to find out why.

Gary!

How are you?

Can I give you a hug?

GARY VAYNERCHUK: I'm in, I'm in.

How are you?

KATE: Thanks for doing this.

GARY VAYNERCHUK: I'm happy to do it.

[classical music] KATE: Walking into the White Horse Tavern is like taking a step back into history.

With the spirit of old New York greeting you at the door.

EYTAN SUGARMAN: The design, the bar, this is the same bar that's existed since 1880 and these are important things.

KATE: The original tin ceiling, the wood of the bar, and the legends that linger in the air all contribute to the tavern's status as a registered historical landmark.

[ice shaking] What was it about this place that you said, I want to take this place over?

EYTAN SUGARMAN: My fear was somebody would take this and turn it into some bastardized version of what this should be and what it has been since 1880.

So.

Uh, I jumped in, I paid too much.

I'm the proud new owner, and, I'm in love with the place.

KATE: In its 140 year history, many others have loved this tavern too.

Starting with longshoreman from the nearby piers, who saddled up to sip in the spirit of New York before heading back to sea.

Then in the early 1950's, it lured a list of literary giants and artistic legends like Norman Mailer, James Baldwin, Bob Dylan, and Jim Morrison.

In fact, legend has it that regular Jack Kerouac was often kicked out for bad behavior.

And the most renowned guest, the poet Dylan Thomas died shortly after a hard night of drinking.

His photo still remains to mark his usual seat.

Ah.

Have you ever been in this room?

GARY VAYNERCHUK: Yes.

Of course.

I've been in all of them.

KATE: It's famed back room brought in beatniks, seekers, writers, and philosophers who gathered to discuss, debate, and of course intoxicate.

Bonding over a brotherhood of booze, bar talk, and the occasional brawl.

EYTAN: I'm in love with what it represents.

It's truly, it's a portal to old New York.

I'm very sentimental about that.

KATE: For Sugarman, the quest to keep this tavern's long standing tradition alive means being open to reinvention.

When I think of White House Tavern, I think of a great place and a place with character to go and drink.

(Laughs) KATE: But it really, I think, one of the things that you are trying to kind of put your stamp on is also making it a culinary destination.

SUGARMAN: Yeah.

I, I agree with you.

I think what it has been, at least for the last 50, 60 years, is like a hard drinkers bar.

And it's certainly a place that is, is cocktail forward.

But you know, I think we stepped it up a little bit.

We have a great wine program.

We have a great cocktail program.

We have a diverse beer program.

In addition, the menu I think has something for most people.

ANDRE: Welcome to White House Tavern.

KATE: Thank you.

ANDRE: My name is Andre.

I'll be your server for today.

KATE: Today we feast on upscale tavern fare.

Starting with shrimp cocktail along with the amazing tuna tartar made with yellow fin tuna and topped with a piece of fresh uni.

Followed by two entrees, the select cut aged burger served with charred onion mayo, crinkle cut fries and the house steak cooked to perfection and served with a generous helping of Bearnaise sauce.

As well as a glass of vino.

GARY: Thank you.

To good health.

KATE: Cheers.

Thank you for being here and being on To Dine For .

GARY: Thanks for having me.

KATE: Oh wow.

That's great.

That is really good.

There really couldn't be a more perfect place to sit down with Gary Vaynerchuk, a sky's the limit thinker who remains deeply rooted in old school values and traditions of the past.

An entrepreneur who is constantly reinventing on the cutting edge, leveraging the latest technology to take his businesses forward.

From launching one of the very first online wine catalogs to then building his own media empire, he is an author, an early investor, prominent speaker, and passionate mentor to millions of social media followers.

Focused on helping others find their own success.

A giant in American entrepreneurship, and he's just getting started.

KATE: I actually had, uh, my very first drink in New York at this place.

GARY: Is that right?

KATE: Yes.

Can you believe it?

GARY: You know, I can.

Which is probably the ultimate reason why I picked it.

I mean, I think this is truly one of the most historic spots in New York.

KATE: Yeah.

Because there's nothing like it.

The history, the age of it.

It's kind of going through a renaissance now because it was, you know, a place where you really just had a pint.

And that was it.

GARY: Very much.

KATE: And now, they're, they're really trying to make it more of a food destination.

GARY: Which I think is really neat.

Right?

Like, you know, so much of what I think about is reinvention.

I'm very fascinated by that.

That probably is what, what draws me here as well.

Which is, after all this time you can still decide we're going to up the food program.

KATE: You can reinvent at any point.

Gary's own story begins with the ultimate reinvention.

Immigrating from Belarus with his family in 1978 at the age of three years old and landing in Queens, New York.

Later, Edison, New Jersey.

Where he grew up watching his father work tirelessly building a liquor store business.

It is here where young Gary first begins to understand his own hustle.

Opening lemonade stands, washing neighbor's cars, selling baseball cards.

At the age of 14, he went to work with his dad at the family liquor store.

Where his sales skills soared and so did profits.

At 14, you start working at the liquor store.

GARY: Yes.

KATE: What in those early years, before you did wine library- GARY: Yes.

KATE: But in those early years, you're obviously picking up on the hard work ethic of your dad.

GARY: Yes.

KATE: But what else are you learning in that moment?

GARY: I learned that watching people walk through a retail store... has ended up being one of my greatest advantages.

KATE: What do you mean?

GARY: I've been able to observe things and see things a little bit earlier than others.

KATE: Mm-hmm.

GARY: Act on them and create success.

KATE: Mm-hmm (affirmative).

GARY: I believe that a lot of that comes from the liquor store.

I would sit and watch people walk through the liquor store.

D Rock would walk in, he would walk, he would shoot straight for the, like, the beer box, open up, get his Coors, come.

And then at the register, he would pick up the peanuts.

Why?

Why did he pick up those peanuts?

I would watch and watch and watch and watch.

KATE: You were watching consumer behavior before you even knew what you were doing?

GARY: Yes.

And I was doing that even before the liquor store.

I was doing that with the signs on trees for lemonade.

GARY: I definitely did it at baseball card shows.

I realized, oh my table location matters.

KATE: Yeah.

GARY: Oh, if I put a big statue of, of Jose Canseco they may stop at my table.

KATE: What was it about you that noticed all that?

No one told you to do that.

That was something innate.

GARY: It was innate.

You know, I was a pretty terrible student.

(Kate laughs) Uh, but the one class I over indexeded in was history.

KATE: Oh.

GARY: And I never really understood at the time, but now I do.

I think it's very clear to me that I work off of history, off of pattern recognition, over certain things change but humans activities stay pretty similar.

KATE: In the mid 90's when the tech revolution began to take hold, Gary took notice.

In 1996, at the onset of YouTube, he launched the wine library.

GARY: Hello everybody and welcome to wine library TV.

KATE: A catalog of wine videos that dramatically accelerated sales at the family liquor store.

You were making these, uh, wine videos.

Introducing people to different types of wine and really having your own little wine TV show way back before people were doing this.

You personally saw an opportunity there and where did that come from, and why did you do it?

[breathes out] GARY: Blogging was a devastating thing for me.

I saw the internet happen.

Search, website.

I'm doing my thing.

And now 2002, 2003, 2004 this blogging thing is taking over.

GARY: And I'm not good at writing.

KATE: Mm.

GARY: And I'm seeing this happen and I'm like, God darn it.

Like... KATE: You're missing out.

GARY: I'm missing out.

KATE: Yeah.

GARY: These people are gaining the number one asset that I care about in the world, attention.

For their businesses, for their practices.

And then all of a sudden, Eric Caster my lead developer at wine library says to me, have you seen- you know, three years earlier I said what if I make a wine video and we put it on the website.

Can I do that?

And he ran the numbers, and this is early internet.

The server costs were enormous.

He was like if 100 people come to the site, it's gonna cost this much.

I said forget it.

KATE: Right.

GARY: So three years later when he saw YouTube, very early on, 'cause it was very teched out and new and knew things were happening.

He said did you see this?

And he goes, that video thing you wanted to do, you can put on this.

You can embed the video, put it on our site and you don't have to pay anything.

They're hosting it.

That was it.

I said... Like, literally immediately.

Let's go film on this.

This going to be an integral part of the way people buy wine and, and everything in the world.

What made me do that?

I know that video killed the radio star.

KATE: Mm-hmm, it worked.

GARY: It works.

Video works.

The business went from a 4 to a 60 million dollar business.

KATE: That's incredible.

After you had that enormous success with your family's liquor store, how did you get from that success to then realizing I could do this in other arenas?

I could really be an entrepreneur, a serial entrepreneur and a business man.

GARY: I built my parent's business for them.

KATE: So you built it, but you didn't own it.

GARY: Listen.

My dad started and built it, but I accelerated it dramatically.

Had this big accomplishment and kind of had to start over financially.

Which was grounded in my love for my parents and my own humility.

I was okay being 34, not having the amount of money in my bank account that I deserved based on my 12 years of work.

Which is... You can imagine why I have so much passion telling kids be patient.

KATE: Yes.

GARY: You know, my dad has a funny trait where he was very competitive with me.

Like we would debate who was a better businessman.

GARY: And people would- And in the liquor business, in the wine business people would razz my dad.

You shouldn't compete with your son.

You should want him to be better.

And I remember sitting in the seat, in this conversation, in a, in a restaurant like this.

And actually understanding my dad.

I wouldn't agree with the person.

I wouldn't be like yeah.

I actually would stay quiet.

Because I'm like I get him.

KATE: Yeah.

GARY: 'Cause I'm going to compete with my kids too.

(laughs) GARY: I just get it.

KATE: Yeah.

GARY: And so I actually always really admired my dad's competitiveness.

KATE: In 2011, Gary left the family business and went out on his own.

Working out of a conference room in his friend's office to build VaynerMedia a modern day full service ad agency for social and digital platforms.

Today that company makes over 100 million dollars annually and employs 1000 people worldwide.

Along the way, he trusted his gut and made early bets on tech companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, and Uber.

GARY: Everybody told me YouTube was stupid.

Everybody told me not to put all my money into Facebook.

Every good thing that has ever happened to me, everybody told me was stupid.

KATE: And then, he launched VaynerX a media holding company with arms in production and talent management.

Most recently, he co-founded Resy an online reservation service for restaurants.

Then he created Empathy wines which sold to Constellation brands.

A torrid run that has cemented his status as a serial entrepreneur.

GARY: When people are like, Gary don't you get burnt out or are you ever anxious?

I'm like, no it's a game.

KATE: Yeah.

GARY: I have an incredible relationship with work.

I don't value my notoriety.

I don't even value the money that's associated with it.

I value that I'm lucky enough to play it.

The luck of the DNA draw and the luck of which parents I was given and the luck of being in America at the time and the luck of the internet coming along at that- you know, there's a, you know, I think people that work hard and really do things struggle with the word luck.

I do.

Like forget- Like I want to fight you if you say I'm lucky.

KATE: Yeah.

'Cause you've worked so hard.

And very few people would use the word luck.

GARY: But I was born in communist Soviet Union.

Five years before I was born, 16 people tried to hijack a plane and go from Soviet Union to Sweden.

There was an international event that put pressure on the Russian Premier Brezhnev who then decided to change the immigration policy and actually let some people out.

And I was one of those people.

KATE: So there's your luck.

There's that tension between people who are really competitive and at the top of their game.

That moment where you can let that will to win and that competitiveness just eclipse your humanity or your care of others, and, everyone has to make that decision, right?

And I feel like one of the things that you love to talk about is kindness and empathy.

And it's not something you hear or see businessmen talk about very often.

Why do you do it?

GARY: I do it 'cause it's my truth.

My mom is the best, and so much of everything, I give her so much credit.

I'm such a byproduct of her parenting.

She was strict.

Strict about things that I pride myself in today.

She was very passionate around kindness.

And she always celebrated good behavior, which was very powerful.

The affirmation of opening the door for a lady or being nice and empathetic to a friend, little stuff.

Like my friend would trip and get hurt and we were all playing and I would come over and be like are you okay.

She would observe it and say that was good.

You know, like- KATE: She would reward that.

GARY: She would reward compassion and empathy and things that come natural to me today.

And so, one of the reasons I think I've evolved in business to a place of kindness and compassion is it is not winner take all.

I think people live in scarcity.

I think people live in other people are taking away from them.

I just don't believe that.

KATE: And that's how you see the world.

That is your POV.

That it's not worth it if you're going to win at all costs.

It's all, it's only worth it if you can win but also do it in a spirit of kindness.

GARY: I believe, very deeply, that it is not how much money you make, it's how you make it.

I believe in that very deeply.

And I live my life that way.

I think empathy is the- It's why I named my wine that.

I think it is the most important word in business.

I really do.

Because when you have it for the consumer, you'll always bring them the most value.

When you have it for your partners, you'll always have good relationships.

When you have it for your employees.

Doesn't mean you don't lose your way, doesn't mean sometimes you're confused, doesn't mean sometimes you don't see it.

But the intent of empathy is a religion that I would like to see grow immensely in business.

KATE: In addition to running his media empire, Gary pays it forward.

Publishing an enormous amount of content to reach millions of followers on social media.

Through his platforms Ask GaryVee, Tea with GaryVee, and the GaryVee video experience.

Providing advice, mentoring, and answering questions for an upcoming generation of entrepreneurs.

KATE: You have such a heart for young people who are struggling and having a hard time finding their way.

GARY: You can't let your self esteem or self worth be wrapped up into metrics on YouTube because it's one tiny proxy in the reality of what you're up to.

You understand?

AUDIENCE SPEAKER: Thank you.

[sniffling] GARY: You're welcome.

KATE: I guess I'm just curious as to where that came from.

Because that's not related to your Resy business, that's not related to Empathy wines, but that is really one of your calling cards on social media is a deep care for young people who are trying to figure their way in the world.

GARY: I'm incredibly connected to them.

You know, I have this incredible relationship with the youth.

I like them.

I like them.

And I want them to be happy.

And they can do so much.

You know, it's funny, there's a level of selfishness in my selflessness.

I wonder to myself... who's the best entrepreneur?

Who?

And what defines her or him?

KATE: Mm-hmm.

GARY: Is it how much money they make?

I think...

I had never had a relationship with money the way a lot of entrepreneurs do.

I don't love it.

I don't- KATE: You never had it.

GARY: I never had it.

I don't really want stuff.

It just- You know.

KATE: You do talk a lot about how money doesn't bring happiness.

GARY: It doesn't.

KATE: And that, you know, you, you have to define success for yourself.

GARY: I write checks plenty.

But the time and effort I put into actually bringing people value that might change things, that takes a lot of energy and time.

And money.

And then number two, I do want to be, back to winning and competition, I'd like to be one of the most significant entrepreneurs of all time.

Why not?

Why not?

KATE: Put it out there.

GARY: Yeah, why not?

I laugh when I say that and sometimes people are like, oh.

I'm like why?

Why not try to be the best person of all time?

Why not try to be the best in your craft?

Why not?

And I- The way I define that is, yes, I do believe I'll have to achieve a certain level of, of wealth creation to even be in the conversation.

But I'd like to think in 45 years that the conversation will look, something like yeah, you know, Bezos did make more money.

Right?

But Gary gave the most back to all the other entrepreneurs.

KATE: Impact and contribution.

GARY: Yeah.

KATE: As people recreate themselves out of this pandemic and restore what they had and redefine it and recreate it, what advice would you have?

Not only for business but for individuals as they reimagine their world?

GARY: That self-awareness and patience are the ingredients to put you in a position to succeed.

Do, how much time have you spent actually being honest with yourself about you?

KATE: Mm-hmm.

GARY: Not trying to trick people around you.

And how much humility and patience do you have to put yourself in a position to succeed?

Do you have the humility to quit your job and do something else that you like more even though you know that that means you have to trade in your leased BMW and get a lesser car?

I believe that most people's unhappiness is grounded in the fact that they care about other people's opinions about them.

KATE: More than they do what would actually make them happy.

GARY: Correct.

Which really drives me to a very unhappy place because usually it's trying to impress people you don't even like.

KATE: Right.

How sad is that?

GARY: It, it's sad to me.

KATE: Yeah.

GARY: And so I want to create an alternative conversation.

KATE: Another conversation he's trying to change is in hospitality.

When you look at your work with wine library and your dad's liquor store and then Resy and then Empathy Wines, the common theme is the hospitality business.

Tell me a little bit about that new venture and kind of how you see hospitality moving forward.

GARY: Started a group called the VCR group.

With David Rodolitz and Josh Capon and, and our fourth partner Conor.

KATE: This is phenomenal.

This burger.

GARY: Yeah.

They are- This place, I'm telling you.

This is now- KATE: It's really, really good.

GARY: Uni on top of tartar, are you kidding me?

KATE: Yeah.

GARY: Um.

VCR group, we- KATE: So this is a new venture?

GARY: This is brand new I mean, the timing of this couldn't be better.

We just announced it.

KATE: So what is VCR?

GARY: We will be a restaurant, hospitality group.

We will open up restaurants, but we're going to be remarkably innovative.

KATE: Mm-hmm.

GARY: We may start concepts on delivery only, before we open... a place.

We may... start a concept that's only on the third floor of buildings in Manhattan.

We may, uh...

I was telling the guys, I was like let's start a restaurant where ice cream is the first thing, that is served.

You sit down, you have to have ice cream.

Then you eat like- KATE: New innovative things you haven't seen or done.

GARY: Correct.

So it's been really fun.

That's why I signed up.

KATE: Right.

A life long, die hard Jets fan.

There is one big dream he will always be chasing.

So what your gut feeling, will you own the New York Jets?

GARY: Yes.

(Kate laughs) It would just... just bananas.

KATE: Yeah.

You've kind of made that, a big audacious goal of yours.

And you've said it out loud and you talk about it and you, you're almost bringing it into being.

GARY: I mean, think about how crazy that is.

Forget about the ridiculous level of wealth creation I have to do.

Here's the punch line.

It's back to the way this conversation, this little piece of the conversation started.

The greatest thing that ever happened to me was trying to buy the New York Jets.

It's like pulling up to a driveway at a garage sale.

It's irrelevant what I buy at the garage sale.

And whether I buy for two dollars and it's worth 80.

It's the moment right before that.

This is what I dream for everybody who's watching.

The ability to understand yourself leads to incredible happiness.

Because once you really know yourself, you start to have a compassion for yourself of the things you aren't.

GARY: And you start really trying to scratch the things you are.

KATE: I can't tell you how much I enjoyed my time at the White Horse Tavern with Gary V. He is the personification of the American dream.

An immigrant who hustled hard and is breathing new life into the term entrepreneur.

Debunking the myths that have made this word trendy lately.

You know, we all learn from our parents.

But for Gary and his insanely special work ethic he got from his father, the kindness and empathy his mother showed him daily, few people try to carry the flag of what their parents taught them more proudly and more distinctly than this guy.

And I say this guy because I get the feeling that's how he wants to be thought of.

Just a guy who worked really hard and with luck and favor, hued out his own version of the American dream.

KATE: Gary this has been wonderful.

Thank you so much for joining me.

GARY: Cheers.

KATE: Cheers.

GARY: Thanks for having me.

KATE: If you would like to know more about the guests, the restaurants, and the inspiring stories of success, please visit todinefortv.com or follow us on Facebook and Instagram at To Dine For TV.

We also have a podcast, To Dine For the podcast is available on apple podcasts, Stitcher, or wherever you get your podcasts.

To Dine For with Kate Sullivan is made possible by... ANNOUNCER: There are people in your life who count on you for what matters most.

American National agents are close to home and committed to our communities.

They'll help you find the right coverage for you, your family, even your farm and business.

You can learn more at americannational.com.

♪