– So, (chuckles) my mum started a clothing business a few years ago. – Okay. – A kids’ clothing goods business.
– Okay. – So, she wants help building our brand, but then, the selfish part of
me is focusing on my business, viewing myself as a
entrepreneur and whosoever. – Yes. – How do I balance my
self-desire with my real desire to help my family and help
my mum do what she’s doing. – That’s a great goddamn question. So, a couple quick questions. Is your mom, since she just
started, so, small business? – Yes, quite small business, quite small. – So, I would tell you, Danny, that you got something really going for you. Here it comes, guys, get ready. How old are you? – 21.
– 21, perfect. Kinda thought that’s where we were going. Danny, most people, so,
one thing that’s really pissed me off about London so far, is I’ve been running around to meetings, starting at 4 PM, there’s been
millions of people at pubs, and, I’m like, are these people working? If you follow me on Snapchat, you’ve already seen what, I’m angry. So, anyway, taking a step back, you’re 21. You can stay up 18 hours a day. I know that you ran out
of, like, class right now to be here, so I guess you
gotta balance some school hours. But, how many, how many,
I mean, you got hours. – Yeah, hours.
– Right? So, I work two full-time jobs every day. I work 18 hours a day,
that’s nine hours every day. That’s more than a lot
of you work, in half. A lot of people who are watching right now don’t even work nine hours. I work 18, that’s two. So, I think you can do both. – Cool. – You just hafta go to less
pubs, go watch less football, as you call it, soccer, you
just hafta to less shit, like, stop chasing the girls, or whatever. You just gotta, you gotta
work, if you want it. And, if you don’t, what
you gotta do is figure out what balance you gotta do, and
whether it’s 60/40 or 50/50 or 90/10, for your mom, for you, whatever you break it down
to, the way to really fix it is by more, having more hours. You know what I mean?
– Yeah. – And so, I’ve been able to
solve a lot of my concerns, my ambition, my work-life balance, on just doing more hours to a net score.

“What is your biggest goal heading into “the homestretch of 2015?” – My biggest goal, professionally, is where I’m gonna go with
this, is to set up VaynerMedia for it’s biggest year, get
all my venture capital, and investing world in
order, a lot of transition, a lot of exciting stuff coming
that you’ll be hearing about, wrap up the book, very much focus on Resy and BRaVe and FaithBox, the businesses that I’m, and Grape Story, the businesses that I’m
deeper involved with, get deeper into the HR of 100 employees at VaynerMedia that I
haven’t gone as far with I wanna have that
personal connection with, dismantle the #AskGaryVee
Show through the winter and put out better and
better and better content, work closely with DRock to make a couple of killer, original videos,
work with you, Steve, to make WineDeals really
powerful, and I think we can, so those are some of the
things off the top of my head. Hopefully have my first really
exciting football season in five years, four years, I really am very optimistic, or maybe not, you’ll find out Friday on
my football preview show, and start the process, and most of all, number one, now put a
little personal in there, continue the workout regimen. I don’t know if you
noticed, but I’m starting to go into muscle gaining mode, and start the process of
hacking more time with the kids from a Monday through Friday standpoint than I have, whether
that’s walking to school, whether that’s coming home early. It’s not built into the infastructure this September, the way I wanted it to be, maybe because I got so much time in August that that didn’t populate,
but I’m definitely, in the same way that if
this show was going on the year before I started working out, I know it started right
when I started working out, you would’ve heard me talk a lot about working out, working out, working out. I’m a very smoke then
fire kind of individual, so I’m starting this smoke
on this kids hack thing, because the extremes are working, but I’m trying to find a little more time.

be four teachers this year I you know
you know I’m cynical and tough on the traditional education system in the USO
I would say that a goal for teacher this year would be to find one to three
students that are clearly not predisposition to be successful in the
machine that is the education system you know the one that’s been built you know
78 years ago and is being crammed down our society’s throats here as the world
is fundamentally shifted cool so teachers playing within the rules of the
game that you play like all of us I do it you know I’m a wild entrepreneur you
know we all do it we all play in the confines of the rules that we set for
ourselves try to find more than three of those
kids and it’s not going through the cliche things like worrying about you
know hitting the market within the game or
medication all the other stuff that is being pounded me take a step back and
open up your eyes pushing for watching the show and you’re seeing this advice
line right if you’re watching more than to these episodes you’ve gotten through
the stuff that I’m throwin and you’re catching and vice versa and so we’re trying to find the one to
three of the kids that look like me they look like so many of the other people
that couldn’t win those dynamics but are so we’re so lucky and so many other ways
to win in the actual world that we live in and try to give a boost try to me
that teacher I wish I could sit here besides senior Kennedy my Spanish
teacher in high school I would sit here and read aloud two or three teachers
that set that saw me for me I could give them down right now so yeah
you’re right I was gonna be ok be that teacher for those 123 students
so that they can and seven to 12 15 20 to 49 years from now say missus Boston
she was the one that new 143 it that I wasn’t me for that but that I would be
special at my part for my singing for my pitching a nice telling you that Joe
asked do you think a company staff by fifty of your clothes will be less or
more successful entertainer media I love

– Yes. – And how you map that. I heard you say recently
that for your 30th birthday, you freaked out and
started Wine Library TV. – I did. – And I thought that was interesting thing to map back, was that the
start of a hockey stick that you kinda went on? I know you talk about turning 40, and how that’s very exciting. – Couple months away. Exciting. A la, I might just disappear. – I’m excited, yeah. How do you see, sort of
like, milestones like that, like, an age or something like that, and sort of like, career,
and comparing yourself to sort of like, where you should be or… – I don’t know if I’ll
ever have anything like 30 because 30 was a real kind
of interesting moment for me because I really, really felt
for the first time in my life, on my 30th birthday, that I
would not buy the New York Jets, or that my, you know, and I think, look, this is a good time to
talk about it if like, if it’s confusing to
anybody, I’d be very okay if I don’t buy the New York Jets. I want to buy the New York Jets, but more importantly, I want the process of buying the New York
Jets, and what hit me was my behavior wasn’t
acting towards a process of buying the New York Jets. That I was starting to become complacent, which was very weird for me,
and it scared me a little bit. Like, I had made it, right? And by everybody else’s definition, and I allowed, in a
world where I very much, we talked about it in Sid’s question, live in my little world, for some reason, you know, obviously I got married at, the day before my 29th birthday, so Lizzie was new in my life, like,
whatever had happened in those two, or three, or
four years from 26 to 30, it was the most complacent
version of myself. I mean, I am a, dramatically,
more of a hustler today than I was at 26, which is
tough because I have children and a marriage, and
I’m like, damn, I mean, this would have been a
much, I’d much rather have worked it out, which
is why I push that objective so much in people’s 20s,
that’s when you don’t go for the cash, that’s
when you sleep on the floor. Right? Like, with 19 people, and like, this room. Like, Jerome Jarre slept at VaynerMedia. Right, like, he hustled,
and now he makes millions of dollars being Jerome
Jarre, freakin’ slept here. Like, I know what it takes, and I, so, anyway, I don’t know why
I’m going left field, birthdays are interesting. You’ve had some big birthdays recently. Birthdays are interesting for me. I’m definitely freaking
out about my 40th birthday. Like, because what’s happening
in my brain right now is like, 40 to 50 is the
foundational decade of like, you know, like, if I don’t
really crush that decade, and there’s a part of
me that laughs at me, because then I’m like, hm. Then I’m gonna come to 50
and be like, all right, 50 or 60 is, like, this is
where you really go to moguls. Like, I know my, I’m
self aware enough to know that’s how I’m driven. I have this equal push
to like massive ambition and equal understanding
of myself knowing that the goals that, you know, it’s funny, I can’t wait to be a
public figure in my 60s, 70s, and 80s, and talk about,
there’s a weird part of me, and it’s an emerging weird part that says, wow, I can make a bigger
impact on the world if I don’t buy the Jets
because I could talk about, you know, the satisfaction
that I have in that I gave it my all, and I, you
know, there’s serendipity, and there’s other variables,
or that, you know, this, you know, I’m a weird
dude, this tragic event happened, and I adjusted my
priorities for, this incredible thing happened, let’s look
at the bright side, and I, you know, my son was a whiz
kid violinist, and I decided to deploy against that. You know, so, I think that
the way I think about it is for me, birthdays are weird, I, definitely milestone birthdays. 30 and, 40 is ripping me right now, and like, 30 did, and so 50 will, and so, and I don’t know if I’m
forcing that narrative or not, but they’re real, but I think
that they definitely make me think about things and readjust, like, I’m sure that, it’s a
cliche thing that I’m sure happens to everybody, but
I didn’t have them at 18, or 21, or 25, it started at 30 for me. And probably speaks to
what I’m ambitious about. I wasn’t as much worried
about my childhood, or things that of that nature. My career has been the beacon of my life outside of my family, and that’s what, I don’t associate myself
with, you know, like, being a party dude, or
like, getting the most out of my 20s, it was
more career oriented. And so, I think it’s
different for everybody. And I think, you know, it also speaks to, you know, these big birthdays are also a tremendously important time to reflect around family and health. Obviously, I took care of my health, and in spending a
disproportionate amount of time on my family hacking, as happy as I am with the extremism of
weekends and vacation time, I’m starting to bubble
up some other thoughts. And so, I think, you know, I
think it’s fun being a human, like, it’s fun to hang
out with the interns here who are like, starting to
go to that next chapter where like, the game they’ve
played their entire lives of school infrastructure’s gonna go away, and they go into a different game. And that’s interesting to watch, and that’s interesting that my parents are interesting to watch to me. You know, there was
something I read that said, you know, when you save
money your whole life, you don’t know how to spend it. So, I’m watching my
parents struggle to relax and enjoy this next
chapter of their lives. And so, like, I’m very
observant as a business person around psychology, but
also as like, a human, I’m interested in how people roll, and I think the best thing
I can say is, you know, go with what feels right. Attach yourself to a couple
principles that matter the most, and let the cards play out as they will.

“When you’re business
is successfully growing, “when do you start another? “And how much time do you devote to it?” – I think it comes down to who you want to be as an operator. Travis Kalanick, CEO of Uber, really taught me a lesson
a couple years ago. When Uber was starting to
take off, he became the CEO. We did angel deals together, and i was pinging him
about this hot angel deal. And he said, “No, I don’t
do angel deals anymore.” And then I pinged him about a talk. And he says, “No, no I’m not gonna talk.” And it was just very focused. And then he’s basically in that Bezos, Steve Jobs, Zucks mold, which is, this is it. This is it. This is the job I’m gonna
do for the rest of my life, and this is my career. I already, clearly, am on my second oofy business. I think I’ve got two
more, three more in me. And so, I’m gonna be an
entrepreneur that has, you know, four or five businesses, is my intuition, India. Clintus. And so, I think it comes
down to who you are, right? And what you want. Like, what’s the size level of a business that gets you to go
into a different place? I mean, VaynerMedia
next year, revenue wise, is going to substantially, probably pass Wine Library’s
biggest year of revenue. So I’ll be going into new territory. Am I an entrepreneur that likes that 50-100 million dollar revenue place, then I go away? Or am gonna see? It really just comes down to a lot of different circumstances. I do think that you need
to question, the question. Which means, if you’re already
asking me this question and thinking about going
on to the next thing, you need to figure out how much you love the
current thing at all. Are you just trying to pass it away? I think there’s a more
interesting insight to that. I think everybody who’s watching the show, needs to think about, are they happy with their business? There’s businesses that you could be making $200,000 a year in, that could be holding you back. ‘Cause it’s a ton of money,
you might just not like it. And so, I think there’s the like factor. For me, I will run this
business, VaynerMedia, as CEO, as long as I love it. That’s really the answer. I mean, I’m glad I got to stick here, because I kind of used a financial proxy as the justification. But to me, as long as I
love it, I mean it could be. But my intuition tells me
I’ve got a couple more. So, I think it comes down to you. And I think it also comes
down to infrastructure. If Brandon Warnke and Justin
Novello and Bobby Shifrin and John Kassimatis and Bryan
Delatorre and Geoff Thurose, if they weren’t in place at Wine Library, along with my dad, I would still be there. VaynerMedia, I mean, some of
you have been here for awhile. VaynerMedia is a helluva
lot better shape today for me not be around, than it was a year ago. I mean, a helluva lot. We’ve gotten dramatically more senior. People have grown. But, I think it’s still
maybe a couple of years away before I feel like it can
sustain and grow without me. And so, the practicality of
this decision matters as well. India, wait a minute, how
did we not talk about this?

“What are your goals for VaynerMedia? “Is there an end game?” – There is an end game. I want to build the greatest
marketing company of all time that is an evergreen business for me that I can deploy all my
future activities around. AKA, when I own the New
York Jets, VaynerMedia will be the marketing company
that re-designs the logo, that does the marketing
plan to take more of the New York market share from
the Giants back to the Jets. To sell tickets while
everybody’s living in a virtual reality world and feel
like they’re playing, and why would they go to a stadium? I think what will end up
being one of the great pillars of my business career, the
decision four years ago, really six years ago, but
really four years ago, to build an agency that
scales my skill set to build infrastructure around me to
then enhance all my future. Take one step backwards,
’cause that’s what VaynerMedia was, to build a client
service business that was taking away from all my other behavior. One step backwards, for two steps forward, DRock, you’re too slow.

“you get asked all the time
that you can’t stand answering?” – What’s one question I
get asked all the time that I don’t, that I
can’t stand answering? Which one is that Dad? The Valdez? Great Pinot, right? – And I’m not, you know? – I know you’re not a big Pinot guy. Alright DRock, over here. This is not a wine show. – I think I’m going to finish it. – You can finish it. – I don’t know if there’s
any question that bothers me that people– – He’s so chill. (laughter) Nothing, nothing, you know. Really, doesn’t take it personally, uh. – [Andy] What’s a question
you always get asked– – You know, Dad, I’m gonna take
advantage of having you here you know, obviously we’re the
same but we’re very different. – But you’ve got a lot of me. – Yes, I know. – The better– – The competitive thing. – Yeah. – But, were you interested in the fact that I’m so unphased? You, listen, there’s a
lot of people watching. Tell the truth, you get upset. – Eh, about? – A lot of things. (laughter) – Uh, yes of course. I’m human, I have yeah. – But, you agree, in
business I’m kind of weird. I go into this weird state where I’m not– – He’s different and he’s very different. No no no, I have to hand it to him not because he’s sitting here, and I really want to give
him compliments, you know, while he’s here. – Guys, just so you know, I’m fishing here because I don’t get this so I’m
using advantage of the show. – But he’s very different here. He made a statement, and I
can’t even repeat the statement, because, to me it’s against my religion– – (laughs) I don’t even know. – He will do business with– – Anybody. Hitler? – You know it rubs me the wrong way, but it’s true, its been proven fact. And I’m a principled guy. – I’m a principled guy! – You are, but, you put
what’s good for the business before your own– – My own feelings. – Yeah, and I can’t, and
I’m exactly reversed. You know, I’m, I don’t know. And probably that’s
what was holding me back listen, I’m not complaining,
I did pretty okay– – Yes you did, mister. – With no language, no, you know. – 100 bucks, poor. – Yeah, I can write a book and my book would be better than his,
but that’s beside the point. (laughter) He’s making a face. – Because it wouldn’t be better. That’s why I’m making a face. Let’s play one on one. Show the basket. We’re gonna play one
on one to settle this. – Listen, we just had my
younger son get married. – AJ, they know AJ. – Everybody knows him. And you would not believe what
took place at the wedding. Gary gave a speech, I gave a speech. My daughter jumped in, and it became– – We’re a very competitive family. – Yeah, it’s healthy. – Slightly unhealthy, but
I’m pumped we’re unhealthy. – What do you mean unhealthy? – Well, we’re very– – End of the day– – We love each other. – Even in the business, never left upset. – What, within a year? (laughter) We never left upset in a day? – We kiss each other– – Well we love each other, yeah. So, I don’t remember the question. But I think ultimately,
Andy, there’s no question that really bothers me. I think most people know the
answer to most of the questions that they ask me, I just don’t think they
want to put in the work. And one thing that, I will say this. I think one of the best
days of my life, my life,

how do you keep your people motivated? – Tommy, thanks for the great question. Obviously, being one of the
great managers of all time this answer’s gonna come
very easy to you and very natural, I think you’ll get it. I spend a lot of time
thinking about motivation and I think the key for me is I try to motivate in a couple of ways. Number one by example,
I think my actions will always speak louder than my words so how I carry myself, how I interact
with everybody, how I live my life as a man I
think really matters as an executive, as a person, I think
everyone’s always watching. But I also think I equally
try to reverse engineer every single individual person, right. They’re just all different,
they all have different KPIs, different objectives,
they’re in different parts of their lives, some are married
some just had kids, some are trying to make more
money, some don’t want to have four roommates in
Brooklyn, so they’re grinding. So everybody’s got a
different thing and I think what’s important for me to
motivate is to do a great job listening to what makes
them tick, both when I have the few moments with them in person. Alex, get over here for a second. Let’s do a real life example
on the #AskGaryVee Show. Alex, what motivates you,
what are you excited about? – What am I excited about? In life? – Yeah, what motivates you in life? – I just like doing cool
(beep), that’s it pretty much. I want to be successful
and just do cool (beep), that’s basically why I’m here so you know. – Cool man, alright, get out of here. So, Alex is easy, he just
wants to do cool (beep). So that’s easy, we do tons of cool (beep). He’s check, he’s good, he’s motivated. And you go on and on and on and you try to figure out, was he
scared that he was on camera and is that the real
answer, like are they really gonna tell me the truth,
they never tell me the truth usually upfront, few and
far between and so it’s a constant behavioral HR driven reverse engineering what they care about. India and I had a pretty
intense conversation about her future ambitions,
remember you wanted to be the head of social
media for museums. I take that very seriously,
like I know these things about my peeps, this is
even before India was on the inner circle of this team, like I I remembered it
better than you did. – Yeah, that’s true, you did it’s true. – So I take enormous, you don’t get to be a great all time leader without being
a great all time leader. There’s a lot of work that
gets put into being good at what I do and I’m very,
very up to the challenge and so it’s predicated on an
enormous amount of listening which is why I’m such a
paradox because boy do I (beep) love to talk but the amount
of listening that I’m actually doing always surprises
people when they start going a couple of layers deeper so
the answer to your question is I motivate, Tommy, by
figuring out what every single person is ticked and wired like and what makes them roll and I also recognize that that changes every
single day and they have four to seven, twelve
milestone things that happen in their lives,
which will change the trajectory of their
ambitions, wants, hopes, and dreams and I need to be prepared for every single one of those
for all of them forever. – [Voiceover] Dylan asks “Do you
still believe that there’s

“your website’s landing
page be a jab like a blog, “or a right hook?” – Paul, you’re welcome for all I do. The answer to your question is, you know, I think it depends
on what your business is doing, and so to me, if
you’re selling something you need to have some level of right hook, ’cause you just have such infinite amounts of time when people land. But if you’re selling information, or you’re looking to
bring a brand awareness, or you’ve been so sell-y
as an organization for such a long time
you need a counter-move to soften your right hooks, and that’s it. That’s the theme of 106 episodes which is that every answer’s different. It’s a reason I can give
away my best advice here, have all my competitors at other agencies and other things come here. I mean I had a bunch of
competitors, literally, small VaynerMedias
asking me for advice over the weekend in email,
which I was answering because at the end of the day, I can give my best advice
because it’s all in theory, right, it’s all in theory. I can give this kind of detail,
which is pretty significant, but then you’ve still got
to get into one extra layer, the clients of Vayner,
the things that I work on have to get to one extra layer
of detail to be successful. And so to me, I’d have to audit what the business or organization
was doing for the last 12, 24, 36 months, if it existed. And then I’d need to understand
what it needs to achieve. But once you understand what
you’re trying to achieve, all your behavior has to match that. And that’s why a strategy,
a religion, a belief system is so imperative in what you do. The amount of people that
are watching this show right now, that are
wishy-washy on what they’re trying to achieve, caring about dumb shit, like oh, I want a nice watch or a car. Like, you’re gonna lose. If you understand how to level that up, I can get any watch and
any car I want because I leveled up, and I still
don’t want that bullshit. And so, I’m not judging you, you do you, you do what you want, but I promise you, push yourself to understanding
what you’re doing at one, two, three levels higher, and you’ll amass that
success along the way that are beneath you. If you want that thing
right in front of you, if you go above it, that
thing is a by-product of you shooting for a higher plane. So, I think it comes down to the details. – [Voiceover] Matthew asks,
“Why is it that people

“Gary Vee, as a successful
solo entrepreneur, “do I have to grow my business bigger “than I can handle alone?” – Q Studios Inc, that’s a great question. I think the answer to that
question is completely predicated on what you want in life. I mean, you’ve set up
the question by saying you’re a successful solo entrepreneur. Are you making the monies
and are you fulfilled enough to keep it at a one woman/one man show? I mean, to me, I can’t
answer that for you. I just had an interesting
conversation with AJ. Our professional ambitions
are in a different place. Everyone’s are. If you wanna build a bigger business, you need to build it
outside of one person. You can only be so big, but maybe what you’re
getting and what you’ve got and how it goes appeals to you. I find a lot of people not
being able to be good managers. They love to micro-manage, they’re romantic and
obsessive about what they do, they don’t allow other people
to come into their ecosystem, and they struggle with the growth curve and they get just as
little exponential growth, they go from making $73,000 a year to 113, but it comes with a lot of pain because they don’t like it, you know? They’re introverted, they’re solo acts, they’re flawed in building
out a big business, but incredibly good and
happy at doing their thing. So it’s not about making more,
there’s really a fine line of making more money
but giving up too much of your happiness for
that bigger money amounts, and then there’s probably
a place where that monies justifies what you want. But to me, doing what you love and doing it the way you love to do it is really, really, really important. I happen to be lucky that that also creates wealth and big dollars, but for the people that it
doesn’t, they need to reconcile. And look, what I don’t get
is a lot of other things, which is kind of the relaxation or the lack of pressure
that comes along with some of the smaller plays, but, I can’t answer this question for you, you need to know yourself. This goes back to all
the self-awareness stuff that I’m trying to put out. This goes back to
yesterday’s video about, or a couple days ago
video of a day in the life where a lot of people
critique my work-life balance, my family time, this, that, and the reason that video
ends with, you know, that’s me, now do you.
That’s a perfect way, actually, DRock, link up there. Give me like a, give me 13 seconds of the day in the life video. – Gary Vanderchuk. – You know I’m a hundred percent right. (laughter) You just do. (laughs) Like, I’m super glad
we’re connected, brother. Alright, now I’m back, and so, you know, I think um, I think it’s on you. – [Voiceover] Adam asks,