“Gary, awesome segment with Seth Meyers.” Lisa asks, “With all this
talk about Snapcash, what is the one thing you’ll
teach your kids about money?” – Thanks for the love, Lisa. That’s an interesting question. You know, my parents taught, my mom, actually, really
taught me to respect money. You know, my dad, for an immigrant, was a big thinker with
money in the business. He really let me splurge and take chances. I give him a lot of credit for that. You know, it’s funny. I have a
weird relationship with money. I want it. I’m aware of its benefits. But I’m much more into the PR legacy. You know, where’s my place in history. Much more so about the dollars. I think if you try to
put yourself in history, the money finds you very quickly. You know, I don’t know. My biggest fear is my
kids are going to be rich versus what I grew up with and so I’m trying to figure out some level of creating respect around it. I guess the only thing that’s
defaulting into my mind is I’m going to make those two work. They’re going to work so they earn their own cash and then they can figure out
what their relationship is with their cash. – Hey GV, it’s TF.

She’s two and a half. And I was wondering in the
future, how are you going to treat social media with your children? Oh no, don’t hide. Say hi. Can you wave? – Oh, cute. – Hi. – Hi. – Hey. Kyle, Ruby, you know
it’s been interesting. Lizzie and I, look it’s hard
to find pictures of Lizzie on the internet. Let alone, you know, all full blast. And Misha and Xander are even more of a rare commodity. I’m not sure. I mean, obviously, I have a
partner in crime in this answer. Lizzie, is very much the
CEO of the household. I’d like to think I’m the COO. Sometimes I’m just like, you
know, the maintenance man. No, I mean, the truth is, we
communicate a lot about this. You know, I’m a counter puncher. I talk a lot about that. I react to the time. For me to predict where
social is gonna be or the technology. But what I do know is one thing. It’s amazing to watch 13
year old girl behavior where their spending 45
minutes on the lighting and the angle on a Instagram photo. And then if it doesn’t get
enough likes in the first three minutes, they take it down. So clearly self esteem is very
wrapped up in these things. And every parent loves
their child so much that you want to keep them away
from bullying and being made fun of or getting into
things too early in their lives. I have the extra pressure,
in my opinion, of deciding to raise my children in
Manhattan where an 8 year old maps more like a 17 year old in many other parts of the country. And so, it’s a challenge. And it’s something that
I think a lot about. And something I care a lot about. I’m not sure exactly how
we’re going to handle it. I think we’re going to
handle it by instilling an enormous amount of love into our children. It’s very important to us
to establish a foundation of who they are. We’ve been spending a lot of time of like, mission statements, and
like key pillars that we want to instill of how we
want them to act, how we want them to treat others
is very important to me. Imposing enormous self esteem into them is important to me.
And I think that to me, there’s new dynamics, but
it’s still always the same and what I mean by that is
the core pillars of good parenting haven’t changed
since the beginning of time. There’s new dynamics.
Those things are probably more important than ever. Having more self esteem,
more perseverance, better manners, all those
things probably matter more than ever. And so, I’m gonna just try
to deliver tried and true things to my kids, much
like I do with business. The world changes, but the
principles of patience, and believing your
people, and establishing infrastructure and playing the long game. I’ve said it before in this show, you know, a tortoise in a
hare’s costume, you know, I believe in old school things like that. So I’m just gonna instill
really good, core fundamentals and let the outside world evolve
because I can’t control it. And just instill my
children into that world, most prepared and best
positioned to succeed. – [Voiceover] Everybody
asks, “What do you think

which is gonna be amazing. You’re gonna be busy as crap, and you’re gonna run out of this time, you’re only 21 once. – [Voiceover] Tiger
asks, “If your dad Sasha “would of ended up in construction, “how do you think it would
have affected your life “without Wine Library?” – Tiger, great question, and by the way, this is a big shout out episode 40 for everybody who’s asking for
a little bit more condensed, we’re keeping it tight on the four oh. I wish I said to the 21 year
old self to drink more 40s. That would have tied in the. Anyway, Tiger, you know what? I think about this a lot. And I’m gonna, I promised myself, and you guys have heard
me talk about this, to be honest on this show, and this is tough for me to say. There is a big part of me that
thinks I’d be more successful if I didn’t go into the family business. I wouldn’t have had the head start that many people can say
I had, and I respect that, but my intuition tells
me that I would have been even a little more hustler, right? Maybe, maybe to a bad degree. But I could see myself, my intuition, and I’ve thought about
this a lot by the way, is that I would have head out west during the internet boom, I probably would have had a company worth $800 million going public in 1999,
that would have went to $1 in stock value, but I
would have learned things in that that might’ve
made me bet even harder on Facebook and Twitter
and Uber than I did, and so, you know, my intuition, maybe cause I have ego,
maybe because I have bravado, is if my dad didn’t have
an amazing set up for me to go in to, if I didn’t
fall in love with the family business and
want to be a part of it, and don’t forget, I was
making a lot of money selling baseball cards. I could’ve went down that route. There’s just, I feel
like I would’ve really found my way, and I feel that my dad taught me honor and a
lot of conservativeness that has helped me not
veer off or have losses, but I think sucked out
a little bit of my speed and aggressiveness, and that
may sound weird to you guys, but I do believe that, and I do wonder if man, I might have been
more financially along. However, and let me put
this stake in the ground, it’s the best thing that
ever happened to me, because forget about the monies, those 10 years specifically
when I was full time of spending that many hours with my dad, when I’m on my last breath,
when I’m laying there and I’m dying, there’s
no question in my mind that those will be one of
the two or three things, obviously all the things I’ve
about to have with my kids, probably a selfish thing about how many Superbowls I won, but like, you know, those, that, those 10 years with my dad will definitely 100% be one
of the final five thoughts as I die, and to me that is an incredible accomplishment and
something I’m grateful for, and very thankful for. My friends, thank you for
watching episode four oh.

“in a time machine, travel back to speak “to your 21 year old self,
and only have one minute, “what do you say?” – Z, I would tell that person
to hook up with more chicks, and not work as many hours. And I know that can be crass, and obviously, you know,
what that crass statement is really saying is have
a little more fun, right? You’re gonna accomplish your things. You’re gonna pull it off, you know. I appreciate that you do
have business patience, but you need to spend
a little bit more time with your friends. You can
go on one more vacation. You can go do a keg stand,
need to live a little bit because you’re gonna have a family, which is gonna be amazing. You’re gonna be busy as crap, and you’re gonna run out of this time, you’re only 21 once. – [Voiceover] Tiger
asks, “If your dad Sasha

Sorry Stunwin. – Always changing the rules. So my question for you– – What, what? – Okay, hi Gary. I’m Emily. – I know, not for me, for them. – I’m Emily McDonough, I
work in HR, Gary’s team. – How long have you been at Vayner? – About three and a half years, and I’ve had some different
roles in the building. – OG
– So. – Really opposite play there. – Yeah, OG. – Okay, see my order was better. For the story of OG, new beat, thank you. – So legend has it that one
your first date with your wife you told her that you
we’re going to marry her. – That’s not exactly true,
but I’ll get into the details. – I wanna hear that story,
and then I also wanna know what dating advice you have for women in their 20’s in New York City. (laughter) – Oh, god, this is great. – We’ve never talked about this. – Listen, you’re absolutely right. I’ve never talked about this. Um, so, the legend is, and it’s true, that after Lizzie and I’s first date, which was a three hour date on a Sunday night in New York City. Which, little fun fact, the Jets happened to win that Sunday, and had they lost the date
would have not happened. So that just– – You would have cancelled? – It’s, I would have cancelled. – Because you would have been upset, okay. – Yeah, that’s exactly right, – Okay. (laughter) – It went extremely well. I lived in Jersey by the Wine Library, she lived on the Upper East Side. I drove her home, and I dropped her off and two minutes after I dropped her off I called her on her cell phone, she wasn’t even in her apartment and my opening line was,
can you believe this is it? And that was it. And we talked from that moment all the way to my 45 minute drive home, and until like four
o’clock in the morning. And we we’re married within
the year of our first date. So, that’s the legend of that story. Little tears from the ladies
in the audience. I love it. Ah, advice, so you know I think about. It’s really funny, having a daughter changes so much in a man’s life, I think. And so, though I know she’s gonna grow up in a very different world, I sometimes project what, and having so many
amazing 20 year old girls that work at VaynerMedia,
it’s an interesting thing. Look, I think we’re living through a really interesting time, right. For example, girls are always in a place where they’re judged by other girls. That’s the psychology that’s
most fascinating to me. What would women do in a world where that wasn’t such an
overwhelming kind of pillar to the way they have to
navigate through their lives. You know, you can look at
how girls dress on Halloween, and like watching all the
comments on Instagram. Because these are the
kinda things I look into. I would say this, I would say, I’m gonna give advice the way
I like to give business advice which is think about legacy, meaning, I think the world’s
changing quite a bit, right. Like, you know, there’s a lot of talk about women in the work place
and the lean in moverment and all these things. Women are clearly closing the gap. You know, the world’s changing so much, especially in the context of the U.S. that I would be more
aggressive, believe it or not. That would be my advice, and I know it’s a little bit of a, kinda a left turn, and maybe it’s a guy
giving advice to a girl. But, like, for me I think it’s never been more appropriate to be on the offense, you know because of just
what’s going on in the world. And so I think, you
know, I think that women are in a much better place than they were 20 or 30 or 40 years ago to say I’m attracted or intrigued
by that gentleman and go on the offense. You got it Alex. And, ah, and that’s what I would say. I think one of the biggest
mistakes guys and girls make is they’re just scared
to go in for the move because they wanna protect and
hedge against their feelings. And I will tell you this, your feelings could hurt for a little bit, but the long term regret, the amount of people who
are watching this right now, maybe even in this room that are sad, men and women, that they didn’t go for it and didn’t make the move, and didn’t try that regret is a hell of a
lot longer and more painful and more drawn out than
the instant rejection of going for it. And so I would say a
little bit more aggression. – Okay.

“What do you is a bigger
obstacle to success, “a lack of time or a lack of capital?” – Roberto, this is a tremendous question. I think the biggest obstacle to success is a lack of optimism. That question in itself
is the problem, my friend. Right? You’re looking at two things
that are both negatives, and guess what? Both of ’em are obstacles. When I started winelibrary.com, transformation for my business, I had time, I worked my
face off every minute, but we didn’t have a whole lot
of money in our profit center so it took more time, right? It’s just the way it is. Today, I have more money,
but boy, don’t I have time. But neither, ever, ever, will be an excuse for me. And so, just to drill
this through the throat of the VaynerNation, that’s
right, I went that graphic, don’t smile DRock,
here’s the bottom line: I refuse to allow you to get
an answer to that question because both of them are firmly square in the excuse column, and I
have no patience for that. There will always be problems. Let’s talk about a million other things that are a way to stop success. The health and well-being
of your family members so it takes your mind away from execution. The country you live in’s government and political concepts in these moments, a la, startups in China that I’ve invested in that got traction, but then people that were
wired in to the government decided to not allow it to happen and then the start up disappeared. Not as easy to be an entrepreneur there, it’s still a communist country. Sorry, it just is. And so all these things
can be problems, right? There’s a competitor
with a billion dollars who’s also skilled and
punches you in the mouth and knocks you out in
the first round, right? The world changing. I mean, there’s just a
million obstacles, right? The media, one bad coverage of you. A moment in time. You know what I think about a lot? You know what I think about a lot? Let’s get really real here,
this is why we did this show. I always, I’m a human being, and I always think about a moment in time. What if I just say the wrong
thing at the wrong time? Right? What if I call out China for
being a communist country in an episode while I’m on a rant, and somebody who’s watching
doesn’t like the way that tastes and that takes away a business opportunity for me in China in seven years? Even though I’m not trying to zing, it’s just things that I saw. What if, you know, what if what if I look down on my phone while I’m driving even though
I’ve really not done that, and I hit somebody and I kill them? And that becomes the story, and then like forget about the story, about what you think about me, I will never recover from that because I killed somebody because
I needed to check a Tweet. These are moments in time. So there are so many things that can keep you from
being successful, right? The people that you invested in having something bad happen to them so it slows you down. My friends, there are a
million reasons why not, but there’s one great reason why, which is, you just gotta persevere, no matter what it is. It’s just the way it is. It’s hard being an entrepreneur. It’s hard building a business. Everybody thinks it’s so easy, that there’s an entitlement. There’s a disaster, zinging China? Here comes my U.S. zing right now: there is an insane generation
of 18 to 25 year olds that think they’re entitled
to having a business because they saw the
social networking movie and everybody’s decided
that if you’re a kid and you know what tech is. Because you used Instagram early on, you’re entitled to
actually build a business. Building a business is hard. And you know what makes it really hard? Everything that happens
every day of every moment. So, you can pick time, you can pick money as the one or two things
that you think stop you from winning your game, but the truth is, there’s a million reasons. 99% of businesses go out
of business for a reason. And that reason is, it’s hard. And so, if you’re watching this show, I’ve got a sense of who you are, and you need to start
creating layers and layers and layers of skin to
be able to get through. Because the glamour of
being an entrepreneur, the goodness, you know you get
very confused by my optimism. Because it’s my optimism, I can’t help it, it’s just how I roll. It’s probably one of
the variable 1% reasons why I’m successful. But please, don’t get it twisted. This is hard. Every day is hard. And if you don’t have the
stomach to weather the storm, you will not be successful. And by the way, let me throw you a real weird curveball, and that’s okay. People have to look
themselves in the mirror and understand if they’re
number two, three, four, five, six, seven in an organization, That has differences
of being a number one, but maybe that’s where
your skill set sits. Maybe that’s how you make
your fortunes and happiness and all the things that
you’re looking for, and so. That question got me
goin’ a little bit, Steve. Because it’s under the context of excuses. And I will never make an excuse. Everything that’s a problem with me, everything I don’t achieve, everything that’s a
problem at VaynerMedia, and everything is my fault. And I succumb to that, and I respect that. And I actually think that’s
the way it should be. And so, um, no excuses my friends.

– Kahlil this was a great question. I’m actually going to
take more sup questions, so if you want to sneak you’re way into the #AskGaryVee show,
the next couple of months I want to do way more sup, so I would highly recommend
tweeting that out. Here’s what sup. I’m going to be leaving shortly, just got back from Cleveland, had a great moment me and AJ have decided not buying stuff is the way to go we don’t want stuff, we want experiences so we decided to go
see Lebron’s first game because we expected the Cleveland stadium to explode pregame and
when he got announced. Did not happen. I’m just saying Cleveland. And so we want to buy experiences, so we made that decision
then the fact that the Knicks ended up
playing them made it so much more awesome, AJ surprised his assistant, Tyler, let’s go see Tyler. People for example, here’s a good moment, I wasn’t even thinking about Tyler, I wasn’t even thinking about Tyler, but because a lot of you are saying we want you to leave the office more often and go show everybody,
what do they all do, I’ve decided to do it. So I’m going to go see Tyler really quick. Just real quick. Tyler. – Looks good. – Speak the the VaynerNation. – Let’s go baby! – Were you surprised? I like how you went for the high five and I dissed him, make
a comment about that. Were you excited when AJ surprised you to go to the game? – Oh (beep) yeah! But DeMayo… – DeMayo’s right here. Let’s show DeMayo. A selfless fact, DeMayo, what we decided to do is we were going to take one of them and flip a coin, but DeMayo said Tyler did most of the legwork, let him go. A selfless act. – He’s the man! – Go Knicks! – He’s waiting for his
Yankees World Series. – Yeah, let’s go. – Yeah, I know what you’re doing. So that’s it, right? So you wanted more of the office, you got more of the office. You know what one thing we haven’t done is we haven’t gone downstairs. What people don’t know is, and the other thing is we haven’t
shown them the other side, so we can show them one
thing we haven’t done is shown you how deep it really goes, so like it goes further, you can give them a little there. So, look, and there’s a downstairs, and we’ll get to the downstairs. Oh Nick, you want to be on the show? – Hi! It’s the #AskGaryVee Show! – So, that’s that. That’s what’s up. You know, Knick’s, we surprised Tyler. We’re doing the show, leaving in a couple hours to go, go ahead DRock. We’re leaving in a couple hours, in about an hour to take the, take the kids trick or treating, so that should be exciting. Leaving early, you know, it’s exciting, I’m in that chapter of my life now where not only am I leaving
earlier to go trick or treating, when I would never do
that, even like in my mind, three years ago when, don’t
forget Misha was already born but not only am I leaving,
I don’t even think twice and that’s a nice place to be. So that’s what’s up, where like the health and family have clearly
in the last 24 months on family, 3 months on health, they have now trumped my work life, so that my work life is stronger, that’s an evolution within my world. But I’m working harder probably than ever. Like it’s insane the
hustles so that’s sup. Jets suck, that sup. That’s pissing me off. Winelibrary.com, Steve is
doing an incredible job I mean, I would say
basically at this point we’re like still hacking at it but editor like, if we go that route. We’re really excited about the content we’re putting out there. Check that out. Wine is starting to
creep back into the DNA, that sup. We’re excited about the show man, I’m really enjoying this guys. Like, by the way, it’s
insane how much I’m enjoying

“happiest in life?” – Tyler, I took this question
for a very specific reason because I think one of
the interesting things about the #AskGaryVee Show is this content and actual infrastructure has forced me to go deeper than I have in any other platform and it’s been interesting
to watch what a lot of you in the VaynerNation have
been responding well too, which is a little bit more
insight to my psychology and I think this question
gave me the opportunity to answer it, and I’m
going to really throw you for an interesting curve ball, and this is 100% the answer. I am the happiest in my life of all time right this second. It’s just the truth, and what I mean by that is, is this moment with these
characters, show them, you know, you know, do they know drock? Excuse me, do they know AlexDS? (mumbles) – A couple of episodes ago. (laughter) – [Voiceover] He’s a regular. – He’s been sick for a couple days, that’s why he looks terrible. (laughter) Is this moment with these characters the best moment? Of course not! Last night beating the
Cavilers going to Cleveland from Lebron’s homecoming and dominating and stunning the world was an amazing, by the way, Cleveland you’re
going to hate me for this. I’ve been giving Cleveland a lot of love, I was disappointed with the fans. This was Lebron, the
prodigal son coming home and it wasn’t enough. Like a random second round
Knicks home game energy in the Garden was better. I was very disappointed. I’m not dissing and I know Cleveland fans
are awesome and their tough. I respect Cleveland, it’s a tough town, not a lot of championships
for a long time. Was disappointed, I had
to throw that rub in there because that’s how I roll. Children being born. Jets beating the Patriots in New England in the second round of the playoffs after losing 45 to three
in a Monday night game just a couple weeks earlier. Way up there, probably my happiest moment, my wife and kids know, but if you ask me happiness, I’m a collector, I’m a momentum guy, I’m a chugger, and so, you know, everyday that goes by that good things keep happening and no death, and that’s how I look at it, is happening in my family or sickness, or terminal conclusions to anybody I care about, feels like the next best day. It feels like it’s always getting better. I don’t know if one day– Look, I’m going to be
very honest with you guys. In my deepest fear, because I’m positive I don’t talk about negativity, I’m deepest fear is that
eventually I become bitter. Right? That I pushed the long game too long and I didn’t capitalize
and I missed moments, but right now I still
think I’m on the climb, I don’t think I’m on the
other side of the hill and so, hopefully I always
have that psychology even to the last breath that I take, but to me, the happiest
moment is right now because everything is
collectively always getting better even when it’s not. You know, there’s always
going to be challenges. It still is. I just, that’s how I see it. – [Voiceover] Chase asks,
“How can you stand out

– [Voiceover] Michael asks,
“How do you define hustle?” – Michael, this is funny
because show his face. ‘Cause I can see him grinning. This was the first question– What are we 35 in five? This was the first question
of 150 questions that I can see from the corner of
my eye he literally said, “How do you define hustle?” ‘Cause he could see this (laughter) I mean this is a challenging question. So first of all, it’s
different for everybody, right, but I would say hustle is to me, is that when you have
passion around something, that you were squeezing
every last bit of the juice out of the orange, right. To me, hustle is maximizing
the energy you’re putting into somebody. I’m blown away by people
saying that they’re hustling and they wanna achieve these great things, and then their actions don’t match. It’s like saying you
really wanna lose weight, while eating a Big Mac, right? So to me, hustle would be
putting all your effort into achieving the goal at hand, and for me, that means
making every minute count. Hiring a full time assistant who is… Friday night didn’t happen because I was hustling every minute, like if I miss my 15
minutes to tape this show, I’ve missed my 15 minutes
because there’s so much hustle in my day there’s no, you know, there’s no like… There’s no hanging out. There’s no time we’re like,
if I could do like one joke with you guys as I’m
walking in between meetings, we find that to be a rare
acquaintance situation, like occurrence, not acquantance. Hustle is putting it all in a line. Hustle is waking up one
day, the day before you die, and you realizing you gave it your all until the parenting of your children, the building of your businesses, the philanthropy you wanted to do, whatever you define, it’s just, you know, all in, emotionally
and executionally. In theory and strategy, and in execution. – Hey, Bridget Willard here
from you too can be a guru

– [Voiceover] Darren asks, “How much sleep “should you get on average? “Do you work seven days a week? “Do you have set days off
to spend time with family?” – Darren, you know this
is a great question, I get it asked a lot. I talk so much about hustle
and people don’t think I sleep. You know, I try to get six
or seven hours of sleep. I think sleep is massively
important for the body. Right now I’m working out a
lot, as you guys can tell. And that’s affecting my sleeping patterns. Not that I sleep better, by
the way, everybody thought. I was so exhausted before that I was just sleeping like a rock, I’m
lucky with the sleeping, but I sleep quite a bit. Weekends are for the family. No this on the weekend, anymore
for the last couple years. Lot more vacation time. Going from maybe a week or two, even as early as four or
five years ago to now, then three or four, now even like five. So sleep’s important, rest is important, recharging’s important. It’s not about 365 days
of complete insanity. It’s about 265 days of complete insanity, and a hundred days of really resting and giving you the energy
to have that insanity. I think hustle is about when you’re in it, versus every day doing it, right. So for me, it’s this
Tuesday, uh Wednesday, see? This Wednesday is all in, right? Like I’m gonna go all in
the whole way, every minute. A lot of the people that
are around my life now, even you guys probably,
get very caught off guard of how I have zero minutes in
play for 15 hours in a day. Like there is no, Zak needs
like two minutes to like, hey look at this new
design for Wine Library, and DeMayo, my assistant’s
like, yeah next Thursday. And he’s like, two minutes, right? So I go all in on the days I’m in, but boy, do I rest when I rest. And boy, do I check out when I check out. I don’t even like travel. I don’t want the pyramids
of the Eiffel Tower, I don’t care about the coral reefs. When I vacation, I need
to sleep on a beach. And don’t talk to me. That’s how much recharging. When I sleep, if you walked into my home, punched me directly in the face, and stabbed me with a knife in my left arm while I was sleeping, and
robbed everything in my home, I’d still not wake up. That’s how all in I am when I’m resting. So I’m just an all in character, regardless of what I’m doing.