our special guest is Gary Vaynerchuk,

the self-proclaimed hustler,

is a digital media mogul, author, web show host,

and venture capitalist among many other things.

As the CEO and co-founder of VaynerMedia,

Gary hosts the hugely popular YouTube show,

#AskGaryVee.

And has penned three New York Times best selling books.

Gary has been named to Fortune Magazine's 40 Under 40 list,

of the most influential business leaders,

and holds the number one ranking

on Forbes top 40 social selling market masters.

His newest book, #AskGaryVee, is available now.

How did this all start, you, wine?

(laughs)

What, what happened with you?

- What happened with me is,

I had the great benefit of being an immigrant.

I was born in Belarus, in the former Soviet Union.

- [Larry] My mother was from Belarus.

- I didn't know that.

- Minsk I think.

- Yeah, I was born 40 minutes from Minsk.

And came to the states in '78,

when they let some Jews out of there.

And, we set up in Queens.

And my parents lived the American dream,

they worked very hard.

My dad was a stock boy in a liquor store

in Clark, New Jersey.

And eventually became the manager of that store,

and eventually saved up enough money

to buy a store in Springfield, New Jersey.

I was lemonade stands, baseball cards, real hustler kid,

Blow Pops, anything to make a buck.

And at 14, I got dragged into the store.

You know, oldest son, immigrant family.

I always tell people, Larry,

that I lived their grandparent's life

more than theirs, right?

I'm couple generations behind most.

I did it in the 70's, and 80's, and 90's,

when most people did in the 30's, 40's, and 50's.

- You're a legal immigrant?

- I am, thank God.

- [Larry] Okay.

- Otherwise I probably wouldn't do the show--

- Donald?

Okay. (laughs)

- And, I fell in love with people collecting wine

when I was 17,

because I was into collecting sports cards.

That was my connection point.

I wanted--

- Collecting? - Collecting.

I wanted to build 4,000 wine shops.

That was, I was gonna build a Toys "R" Us of wine,

sell the franchise, buy the New York Jets.

That's what the plan was.

Heard the internet my freshman year of college,

heard that sound,

cuh, cuh, chee, cuh.

Knew that it was special.

And in 1996, I launched one of the first

e-commerce wine businesses in America.

Called WineLibrary.com.

Took over my dad's business,

kind of running it day to day in 1998,

alongside with him.

And from '98 to 2003, helped grow that business

from a three to a $60 million business.

That became the foundation.

Built that on e-commerce, email marketing,

banner advertising, Google AdWords,

things that the marketing world didn't believe yet.

And then, YouTube came out.

And I started a wine show four months after YouTube started.

And that--

- You are not a wine expert?

- I grew up a wine expert.

You know, from 15 to 30,

in those 15 years, my whole life was wine.

- Were you always successful?

- In everything but school.

- Didn't do well in school?

- Poor.

Terrible actually.

Punted it.

You know, it was funny.

And this is where I give my parents enormous credit,

and I've, you know it's funny,

it's a business book that says self-awareness.

My parents grew up, and I give them so much credit,

in a world where all their contemporaries,

as, and you know this,

education's the way out for immigrants.

- Sure is.

- My mom recognized that I was a merchant,

an entrepreneur, a promoter.

- So did school fail you, or you failed school?

- School failed me.

School's failing entrepreneurs every single day.

- Because?

- Because it's not built for entrepreneurship.

It's built for workers.

You know, if, you're being taught to play within the lines.

And there's nothing being taught that maps

to the entrepreneurial market.

As a matter of fact, my biggest cynicism when I sit across

an entrepreneur today,

is if they are too successful at school.

I probably look at Ivy League grads

starting startups right now

with more of a negative light,

than I do somebody who wasn't as good.

- Because?

- Because what I've learned

over the last five to seven years,

and by the way, in the last two, three years,

I've taken a step back on this,

because there's too many entrepreneurial friends

who've gone to great schools that have been successful,

so this is not a blanket statement.

But I will tell you that in a world of private schools,

in a world of mommy and daddy having a lot of connections,

that when you go from 12, 15, 18 years of that ecosystem,

and you go into a market, and you create an app,

the market doesn't give a crap who your dad is.

The market responds to your product,

and a lot of these kids have not been able

to take the punch in the mouth

that comes along with entrepreneurship.

- You're big on self-awareness, right?

- [Gary] Huge.

- How does one get to be self-aware?

- I don't know.

- So how do you teach it?

- I don't know.

But I know it's damn important.

And so, I know where I start and where I stop, Larry.

And I wish,

honestly I'm curious to see

over the next 40, 50 years of my career,

if I figure it out.

I think that,

the things that I've been pushing people to do is,

one, create an ecosystem where you make the people

closest to you feel comfortable to tell you the truth.

So, one of the things I've been asking for people to do

is tell your mom and dad and spouse,

best friend, coworker,

hey, tell me the truth.

What am I good at, what am I bad at?

And spend a month or two to get them comfortable

to actually tell you the truth.

Cause the people that love you

sure don't want to tell you.

- How did the website thing come about?

- Way back when?

- I mean, you, your web show.

- [Gary] Or the web show now?

- What is the biggest thing you do, is your web show?

- The biggest thing I do right now

is I run a 650 person social media digital agency

that works with the brands like Toyota, and Pepsi--

- [Larry] That's called?

- And that's called VaynerMedia.

- And what does VaynerMedia do?

- We're a modern day Mad Man.

We're a Madison Avenue agency,

the same people that used to sell commercial time

on anything you ever did in radio and television,

we now do that on Facebook, Snapchat, Instagram.

And we produce the creative for the brands

to sell stuff, through the phone.

Because Larry, and I'd love to get,

I'd almost want to,

I know we're doing a show here,

but I'd love to get your thoughts,

maybe after, maybe right now, who knows.

I think we're living through a very interesting moment.

I believe that the telephone is becoming the television.

And the television is becoming the radio.

And I've been spending a lot of time studying

the transition, in the late 50's, from radio to television.

Because this is the first time

we've had a platform shift in our society

in a half a century.

And I think it's a very big deal.

And I've been spending an enormous amount of time,

the last five years,

trying to be the best storyteller for that platform.

- Next, utilizing the digital world

for your entrepreneurial benefit.

How social media can transform your business.

Stay with us.

- We're back with the incredible Gary Vaynerchuk.

Is that a Jewish name?

- You know it's funny,

I know it always confuses people.

People don't think it, but I am.

- [Larry] Okay.

(laughter)

The book, #AskGaryVee is out now.

An entrepreneurs take on leadership,

social media and self-awareness.

Okay, how do we use social media

to help our business?

- Well I think we first understand

that social media is a slang term

for the current state of the internet.

And when you position social media that way,

you take it a lot more seriously.

So step one Larry,

for 97% of the people that are watching,

is to actually take it serious.

That's number one.

And again, we were talking as we were getting ready,

a lot of radio people didn't take television

serious when the transition happened.

That was their loss.

- Correct.

- [Gary] Right?

That's what's happening right now, Larry,

this is historics,

that history always tells you the future.

And so that's what's happening.

So first take it serious.

Two, understand that Facebook,

and Instagram, and Snapchat,

and YouTube these are different channels.

It's the difference between CNN and Fox,

and ABC and Sports ESPN.

You've gotta understand the context

of the medium that you're on.

So when you're story telling

about your business on YouTube,

you've gotta produce different content

than when you're putting a picture on Facebook.

So again, sitting in your presence,

I almost wanna ask questions more than do this interview.

I think that people

underestimate context of the medium.

I would assume that when you interviewed somebody on radio

versus when you did it on television,

there's slight differences

'cause they're different mediums.

- Slight.

- Slight and it's slight, but it's real.

And in that slightness is all the magic.

Number three, it's understanding

that you have to provide value.

Too many businesses right now on Facebook

and Twitter and Instagram,

every post they put out is buy my stuff,

buy my stuff, buy my stuff,

here's where I'm gonna be, check me out,

buy my book, check out my experience,

watch me on my show,

and nobody's providing values.

So the prior book I wrote to this was called,

Jab, Jab, Jab, Right Hook.

Give, Give, Give, Ask.

And it gave people a formula

of how to put out content

that actually gave people enough value

that you then had them in a consideration