that’s high praise
coming from you? – My parents.
– Your parents? – My parents
worked their faces off. My mom never and have
a nanny, we didn’t have a babysitter ever. She had three kids. My mom did everything for us. She regrets raising, I’m not
even capable doing my laundry. I’m a slob. My mom picked up
everything after me. Things that she
liked to joke about. That’s what she wanted to do. She did all the
work, no vacations. We took no vacations. Guys I took three,
three vacations in my life. We worked all the time. My dad worked every minute. My parents it’s learned
behavior by watching them and probably my own DNA. I respect my parents’ work
ethic and I respect all the single moms and
single dads out there. You know life is complicated.
Been thinking a lot about as I’m starting to build momentum as
somebody who’s advice is being taken seriously that I’m trying
to be very careful because I’m starting feel a bigger
sense of responsibility. – Yeah. – I’m starting to get nervous
to be very frank with you. Here giving advice and
tomorrow somebody’s spouse is going to die. Die. I had a distant
relative it hurts very bad. He was diagnosed at 65 or
55 as you can tell distant. Trying just to remember. 65 with cancer and
was gone a month. Gone. Now that kid, I know the kid
met him a couple times. Met him at some family
functions his advice is different now than
it was yesterday. – It’s just perspective. – There’s just all these
different variables, right? Who I respect? My parents because
I know that truth. Who else do I respect? Millions of people who work
really hard to provide because life gave them a curveball. You can do everything right
and your wife and kids can go get killed tomorrow by a
truck falling over on them. – Yeah, yeah.
– And so what? You’re gonna go
hustle the next day? You’re going to grieve. You’re gonna
adjust so I don’t know. I respect anybody who’s
trying as hard as they can, trying to live the
best life they can, trying to do the right things but no question my work ethic
only comes from two people and I think you guys know this about
me I don’t have any role models. I don’t care Richard Branson and
Steve Jobs and Mark Zuckerberg and Albert Einstein and
Bill Gates none of these people inspire me.
They just don’t. My parents do and then it
flipped into my responsibility to my friends that worked for
me, my brother worked with me, the DRock’s of the world and
most importantly what’s given me unbelievable scale
is the community. I get inspired by people
wanting to take selfies with me. I get inspired with two guys who
are working their butt off in Ireland who really
really wanted me on the show. Because it would be good for
them to use my name to get other guests and I like that. – [Both] Yeah, yeah.
– I like that. Or appreciated my work or
a percentage of both that. Do you know what I mean?
– 100% yeah. – There’s a lot of ways
to get motivated outside. I love that I motivate people
but I don’t think we need the big names at the top of the
heap to be the motivators. – Yeah, that’s we decided
as well with start ups. We’re going to look after every
startup that we can interview from somebody who’s
opened from five days ago rather than two or three years. – We got a guy at the end of
January who literally came into van and he had quit his
full-time job that day. – Yeah. – And you could see the look
on his face was fear– – Sure.
– but it was good. – There is good fear.
– And we could sense. – He knew what he wanted and
went out for it which is great. – That’s awesome.
– Great to see. – [DRock] Let’s do
one more question. – Just one more question
on that, if you owned

Pat from Smart Passive
Income, quick question, when you get a new idea, when a new idea pops into your head, how
do you, do you have a validation process before
actually taking action on that idea to make sure
it’s worth it or not? Do you have a vetting process,
does your team help you? I’m curious because a
lot of us entrepreneurs, we have a ton of ideas, how do you know which ones are going to work or not. And to follow it up,
do you have an example? – That’s a great, great, great, great, great, great, great question. I’ve two processes. One is completely emotional, the other one is completely rational. There have been ideas,
a la, the #AskGaryVee Show where literally in one shot, though it’s perculated a little bit, in one moment I go, I execute against
the idea and I let the results speak for themselves
and I can stop it. For everytime I look like
a hero, where I make the first episode of Wine Library TV
or #AskGaryVee and I say we’re gonna look back at
this and this was right. There’s seven other things
that I have done like that which are floating
in the internets, and I’m gonna be, we’re gonna look
back at this and be like merr. My first picture from Flickr,
my first picture for Flickr. – [India] I have it somewhere. – Do you have it somewhere? My first picture from Flickr I drew out gourmetlibrary.com. Drew it and I said one day
this will be one of the most iconic pictures in my
life or something like that. And it was because at
that time I thought I was gonna launch gourmetlibrary.com
and I knew that I was gonna build $100 million gourmet business. What happened was I
started Wine Library TV two months later as well
and that became the thing and I never got around to
really doing gourmet library. So, I think I got that intuitive part. The other part is like Wine Library TV, since February, since
really like March or April of 2005 I knew that I
wanted to do a Youtube show. That it was gonna be
big, but it took me until February ’06 to start Wine Library TV. I knew that I wanted
to do an ecommerce site in ’94 but I really didn’t launch it until ’96 but really run it until ’98. I know that I’m going
to buy a brand one day. Puma, Snickers, you know
Pabst Blue Ribbon but I’m perculating and learning for
10 years before that moment. So, I’ve both, but Pat
really the answer is it’s very internal, I don’t go
to my dad or to Brittany and be like hey Britt what do you think. Like, I don’t give a shit
what Brittany thinks. Now that is either a strength
or a weakness, sorry Brit. That’s either a strength
or a weakness but I want to give you the truth which
is I go very internal, I feel it with myself, I
care, you know what’s funny? I don’t care what Brittany
says as my consultant or teammate, I care what
Brittany does as a consumer. I respect the market over
my friends, my family, the people I respect and even myself. And so I think the way to find out what the market’s gonna feel and do is by giving them a chance to react to it. So, I let the things that
I feel the most bubble up and then I execute against those things and then I let the chips
fall where they may. – [India] I found it.
– You found the picture? – The caption is so
funny, one day everyone will know why this pic is so amazing. – Oh my God, see this
is so cool because look, I mean obviously you’re
gonna put the subs on, the so is very similar to show. – Yeah. – That’s unbelievable, one
day, December 30, 2005, oh my God, this is
literally, what’s today? – [India and man] The 16th. – This is literally,
literally a decade ago. Like, two weeks short of a decade ago. There’s a picture of the
pasta I ate while I drew out gourmetlibrary.com
and one day everyone will know why this pic is so amazing. And I’m gonna tell you why
this pic is so amazing, though I didn’t execute on
gourmet library ten years ago, and big shout out to
Eric Caster and John Kay who were there with me that day. Even though I didn’t, this
date was the two week period, this was the height of the
holidays, this date represents the day that I knew that
I wasn’t gonna be in the wine business the rest of my life. This picture really
represents the transformation into what all of you have known me to become over the last ten years. – The dirty bowl is so significant though. – I told you that one day everyone would understand why this pic is so. – I even bookmarked it
cause we were eating. – Cause it’s so amazing, that’s cool. – [India] That is cool. – I’m a little bit emotional about that.

“important decisions do
you trust your own gut “and experience or do you
count on some advisor as well?” – Who’s your go-to person
on a real decision? Do you have one? – You know, it used to be my Dad, but he had a pretty extreme car
accident about 10 years ago, so he can’t really
comprehend certain things at that level anymore. But I go to a guy named Stewart Jenkins. Who works at a big brand called Deckers, a billion dollar shoe company that owns Ugg and Timba,
and some of those brands. And he’s just like a straight
shooter, tells me how it is, great family guy. – Doesn’t try to pander to what you want to hear?
– [Lewis] He doesn’t deal with my ego he just tells me. He’s got such good integrity and morals. – That’s why I don’t speak to anybody, I don’t want anybody touching my ego. – (laughs) Exactly. So I talk to him with real
issues that speak to the heart. – What percentage of decisions
do you make on your gut? – A lot. – Like what percentage? – Probably 100%. – OK, so you really don’t
give a shit what Stewart says. – No, I advise with
everyone on tough decisions but I always know the answer. – Got it. – You know what I mean,
it’s like I know the answer, but I feel like I have to make sure.
– [Gary] Has anybody wavered you from the answer? – People have given me different opinions but I always know, yes, they have. They have, they waver
me, and then I realize I shouldn’t have taken that advice. – So at times, where you
haven’t gone with your gut and you’ve gone with people
that you think have made it or other things, it hasn’t paid off, so you’re now defaulting
as you’re maturing into your own place.
– [Lewis] Yes. – [Gary] I mean for me,
I’ve always been that way. And I think that what happened,
it’s interesting to hear your perspective, it’s fun
to have guests a little bit because you would’ve gotten my answer of you know, no! I respect my Mom and Dad
and things of that nature, but I don’t even, I love them with all of my heart, I just make my own decisions. I don’t know what else to say about this. But it’s interesting that– – I come from an athlete background, so I was constantly coached,
constantly getting feedback. So I like to have the coaching, – That makes sense. – in an environment so
I can just take action and apply the information. But a lot of the times, I know the answer, it’s just trusting
myself a hundred percent. – That makes a lot of sense. I think the one thing that is
an actual item of this show taking the theme from your book and we’ll continue to act on it. I think you should really try,
if you’re watching the show, to try the opposite on the
next decent sized decision. As long as it’s not a top
three decision in your life, then do you. If it’s a fourth biggest
decision type of thing, try the other way as context. I may even try this, no I can’t. But (laughs) that didn’t even last a sentence. But, I think that would be interesting. Because I’m intrigued by
you ending up in this place. My intuition is a lot of
people end up in that place as they get older and older,
because at some level, you’d rather, for me, I’d
rather go down my way. That to me is probably the thing. When you’re making real decisions there’s upside and there’s downside. That’s why they’re big decisions. If I’m gonna go down, I wanna go down because I screwed up. Not because somebody else gave me advice and it just didn’t work out. That’s just, yeah, alright India. – I think that segues really
well into the next question. – [Gary] Oh, a lot of segueing going on.

“Who do you ask when you have
life or business questions?” – Jason, this is my
strength and my weakness, and so I want to set that up immediately. I ask absolutely nobody. It is insane, I think about this all the time, and I truly, and you know what, it’s funny, subconsciously
I said it’s my strength and my weakness, I guess
maybe that answer’s my 51/49 question of, is it a strength or a weakness? I do think about it a lot. I do wonder why I’m not
really mentored out, even with the most amazing
dad who’s in the business, you know, I was mentored, you know, and maybe this
is just the way I roll, maybe I’m being mentored by example. You know, I think my parents, my parents, you know, it’s funny, I’m gonna be a different parent I think, and sit down with my kids, and do my spiel, I mean I love doing this, imagine me as a dad, I’d be like, kid, when the wind blows, you know, I’m just gonna like you know, do shit like that. You know, like, I never really went that route, I watched my parents, and maybe I watch other people. And I, you know, Steve Ross, who’s my LP and investor partner now, one of the most successful businessmen of the last hundred years in the US. You know, I have full access to
him at a scary level, and I don’t hit him up for, like, what do you think? And this is a guy who
owns a football team, you know, 5 billion dollar man, and I never sit down and ask him, I’m like, let me tell you. It’s in me, again, it’s either a
strength or a weakness, but the true answer to the
question is absolutely nobody. I’m a big believer that people should see a psychiatrist, and
vent, and like do that, I don’t do that, even though
I believe in it tremendously, I don’t think I’m a hypocrite, because the truth is, it’s stunning, and by the way, if I ever go through a, if I ever went through a sustained 36 hour period
of being really upset, I would do it in a heartbeat, I would change my behavior, but I am so scared, and so blessed and so thankful, and so grateful for the perspective that
I have as a human being, which is, you just can’t
wrap your head, my friends, VaynerNation, you just
cannot wrap your head around the excitement that I would have in my body, if all the things on paper that seemed like my successes would disappear tomorrow. Obviously I want to take care of my family and put a roof over their heads, and those kinds of things. But you do not understand
my lack of taste for caviar like I just don’t give a shit. Like I love the game. You know why I love the
Jets and the Knicks? Because they don’t win. Do you understand? And so for me, the fear of
failure is not a fear at all, as a matter of fact I would argue that I have more a fear for success than I have fear for failure, and so, because of that, I don’t know, it puts me in a very happy place. I don’t look for advice,
because the truth is, I don’t want to screw anything up. I don’t want to speak to somebody to vent, because I don’t want to
screw anything up, like, I feel like the chemicals
are aligned right now, and I’m very happy. I’m super duper duper happy. – [India] Cool, that’s good.

– [Voiceover] N asks, “Any
tips on how to get a mentor?” – This is an interesting question for me because I’ve never, like
even when I had a mentor in my amazing dad, I like
pushed against it because… My mom and dad like, made jokes, like, that I want to be claimed and like I’m a Cabbage Patch kid and I came from nowhere. My dad always like to rouse
me when he thinks he deserves more credit because I
never wanted to have that. It’s actually probably one
of my biggest weaknesses is my lack of mentorship
or learning from others, like I don’t know, I like
being self contained. So I’m not the best person
to ask this question. As a matter of fact, I’m pretty
sucky to ask this question but I have answered it in the past, and I think we’ve touched on
this theme on the show before which is I think you just
got to go and get it, right? Like, and there’s some people
doing it right now like that one dude that wants
to get you fired, Steve. I like that dude’s bravado, he’s like how do I get Steve’s job? And like he e-mailed me, you see what I’m talking about these
last couple of days? – [Steve] Oh yeah.
– Yeah, what’s his name? – [Steve] Did you see my Tweet storm? – Yeah, and so like, you
know, that’s interesting to me because it keeps pounding
me and eventually I’m going to know his name because he’s like I want to be mentored. Now the truth is I’m not
looking for that right now. I don’t feel like I can deliver. I can only deliver a mentorship
through osmosis, right? We as a collective, had
a meeting earlier today and I think the youngsters all
picked up a little something that they’ll use and they’ll
like learn of like how to scale but I don’t want like a
hey, come here Johnny, I going to… I don’t want that. There’s people that do,
and I think the best way to get one is just to keep
asking the 5 to 7 people that you think can
deliver on that for you. Basically get to the point
of a restraining order without going over that line. Sorry Steve, but like
I really believe that. Steve just did this. I really, really believe that. You know, if you’re
listening on the podcast, like you know, Steve
just put palm to head. But I believe that, I think
you have to go and get yours but freak a girl out, you know. You can’t be, like, a stalker. You got to go and ask that
person and you ask them, and the other way to do it is to provide that person value first. The amount of people that
hit me up for mentorship where they hit me up, DRock! Right behind the camera right now. Hey, I want to make a
long form piece of content for you, on me, you know,
Cloud and Dirt, link it up. You know, what that led
to is what we have now. I mean, I’m baffled by
people’s lack of pains. You want something so
amazing from somebody which is their time and their energy and your opening question
to that person is hey, can you give it to me? That is insanity, how do
you provide value, Alex. I mean this whole room is full of… Alex takes a step in a different direction in his entrepreneurial
career, willing to come in as a community manager, show his face! Show this man’s face when this happens. Willing to come in at
entry-level job with the hope that hey, I hope that
I get noticed and then I can get into that inner
circle that Gary has. And when he was noticed and brought in, he said, you know I don’t
want to put you out here, but like, man I can’t
believe this happened so much sooner which, it happened
what, 4 or 5 months in? 3 months in, when he says so much sooner, he was in the, I don’t
want to speak for you, 18 months, 25, when were you going to give up at not getting noticed? – I was never giving up but
a year’s time was my focus. – So he would have gave up after a year. (laughter) But that’s the key, right? Like, he came in and he
wanted to pay it forward and his version of paying it forward and being in my ecosystem
was coming to Vayner, start at the bottom, work
it to the top, you know. And so, you know, you want a mentor? Why don’t you provide
that mentor with so much upfront value that you guilt her or him into mentoring you. – Hey Gary, Sean Bruce here.
– My boy!

and I was actually born in
Russia like you were as a baby. I’m 14 years old, and here’s my question. I wanna be an entrepreneur
when I get older, but I don’t know where to start. Like, what actions should I
be taking right now as a kid? Thanks. – B, listen to me. First and foremost, by
asking this question and knowing what The #AskGaryVee Show is, you’re putting yourself in a
position to be an entrepreneur. I like that. What I don’t like is the question because what you should know if you’re a purebred entrepreneur, so wanting to be an entrepreneur versus being an entrepreneur are
two very different things, and I have no interest
in giving the medicine to a 14-year-old, especially
’cause I gave the medicine to a 14-year-old Steeler’s fan yesterday, and it wasn’t pretty
and I’m not proud of it. On this show is probably the
second most competitive place I live in, and so what I
want to tell you is this. Look, if I were you, I would sell that Under Armour sweatshirt
that you’re wearing in the video to some other
kid in the neighborhood. I would go back in the woods
in the video that you just had and find some rocks and sell
’em to some nine-year-old girl. That’s what I did. I was that raw. Now, we’re not all the same. What I’m trying to tell you is the best way to become something
is to act like something. So, you wanna be an entrepreneur? Start acting like one, meaning start a business,
start selling things. Both will work, or find a mentor. Find the 18, 19, 20,
21-year-old kind of entrepreneur in your neighborhood and
start helping her or him out for free just to learn the
hustle, to taste the game. You’ve gotta put yourself in the position. There’s no reading about entrepreneurship. There was a question today that
came through for #AskGaryVee that said, “Gary, name the first, “name the four best business
books you’ve read this year.” And I laughed my ass off because I don’t think I’ve read
four books in my life, and definitely not four business books, and so there’s no reading, my man. There’s doing, and so sell
the shirt off your back. – [Voiceover] TJ asks, “As
a fellow son of immigrants,

I work on new business and all things. I’m an account director here. I’ve been here, I don’t
know, about eight months now. Feels like a year almost. I’m really excited for my Vaynerversary. (laughter) So I wanted to ask you a question which I think is going to help some of the entrepreneur viewers but also just the future
leaders of VaynerMedia. When you’re transitioning
from that doer to a leader knowing what your priorities are and where to put your
focus, so that it counts. – Yeah. – Can you talk a little bit about that? – Yeah I can. And you know this is
something that I have a lot. And to put a little more
color for everybody listening, at Vayner and a lot of other
places you get into a place where you, I think you said it right, you’re in execution mode and then all of a sudden you’re managing a team. And those are two very different things. And it’s the thing that I most fear in the organization, period, end of story. Because you have incredible
executors who yearn for the financial upside and the title to then lead a team and boy are those two very, very, very, very,
very, very, very, very, very, very, very, very, very
different skill sets. And so I think the biggest
thing people struggle with, there are so many things people struggle with with the transition. Number one, the thing I hate
more than anything in the world which is micromanagment. I wanna kick micromanagment in the face. I hate it. And, you know, it’s something I just despise and it’s a major struggle
because if you are a great executor you know how to cross those T’s and dot those I’s. And you know, when you see the person on your team whose not
as strong at executing you can’t help it, it
goes against the grain. So that’s number one thing. Facing yourself in the
mirror and understanding, and I’ve talked to you about this, and I’ve talked to so many leaders in this company about this. This is where people get pissed at me. Most things don’t matter. And that’s a very tough mental transition to somebody that manages a team. The other thing that a lot of
people will struggle with, and I talk about this quite a bit in this organization as well, is when you’re a leader you have to be the bigger man and woman
in every situation. And a lot of times people,
especially when they make that first transition, and it’s the first time
that they’re the leader, they look at it wrongfully
because of society, as I’m the boss and they
try to impose their will instead of what I think
the real skill set is. Which is become a full time listener, a full time empowerer,
a full time eat crap and have humility and
empathy and self awareness. So you go from, what I
believe is I.Q to E. Q. and a lot of people can’t
make that transition. I think the reason this
organization has grown so much is that’s all I focus on
when that transition happens. And don’t try to put pressure on people for new business and client services and all the normal things
one has to worry about. Now I’m the leader, now this
client has to respect me. I need to make Steve happy. I don’t care about that. I can take care of that
at the highest levels. It’s about really empowering
people to become leaders. And leaders, you know I love this. This is obviously a subject matter I love. We talked about it even
in yesterday’s episode. It takes so much more motherly, historically, stereotypically
motherly skills to be a leader and I
think people are confused. I think by default people
think it’s fatherly stuff and I think it’s motherly stuff. It’s emotional skills that allow somebody to make that transition. And really one of the biggest factors in this whole thing is self esteem. If you’re not able to believe in yourself nobody else is gonna believe in you. So I think one of the things is, look I got fortunate, I
got a mother that instilled so much self esteem in me that I’m still trying to get some of it out of me so that I don’t come across
as an egotistical crap head. But I think a lot of
people don’t have that. A lot of people in my family
don’t have that, and I see it and one of the weird
little tidbits that I think can make this episode valuable is if you get into a leadership spot and if your self aware enough to know that your mom or dad put you
down your whole life, or society did, or you
grew up as a minority, or whatever took self
esteem out of your body. Or if you never instilled
in the first place. I think you need to find
an outlet to create it. I think you need to find
an outlet to create it. I think one of the things I
focus on here is I instill it. You know, I instill it. I do talk 90% of the
time about the positives. I just can’t help it. I’m optimistic and I just see it. I see the good, it’s what I do. There’s always bad, but I
think you need to seek it out. And it might come in the form
of extracurricular activities. You might be a great soccer
player, or an improv actor. Or maybe the person you date, maybe you look for somebody
who, instills that. I think that’s a very
attractive characteristic. I can tell you the reason
I married Lizzie so quickly was ’cause she was my mom. And so I like coming home
and having a cheerleader. Like, you’re great. I love that. I want that. And so, I think those are
the things that come to mind. – Thanks Gary.

or the people that inspire you? Did you ever have a mentor? – Mark, you know, for people that watch me or have followed me over the
last seven or eight years, this is a very easy answer. I’ve been hard-core about this. I’ve never really been a big
fan of any business idols, including the before-mentioned Mark Cuban, or you know, really the two entrepreneurs, or people that have ever
kind of over-indexed to me were Walt Disney and Vince McMahon, because they were heavy storytellers and turned businesses out of that. I like that, but to say
they were my mentors or I looked up to them,
there is no Steve Jobs or Donalds Trumps, or Carnegies, there is nothing like that in my life. My life is really focused
on two individuals: Tamara and Sasha Vaynerchuk. Tamara from the HR
people skill foundation, Sasha from the work ethic, (spits in hand) you know, we mentioned that
in episode three or four. So, you know, they’re
really my only mentors,