– [Voiceover] Evan asks, “If
you could clone yourself, “would you?” – Evan, this is a tremendous question, and a great one to end the year. Especially ’cause I
announced that I’m going away with my family for two weeks. This is as easy a
question as they’ve come. I would 100%, I mean this is the best, I really wish this technology existed because I would take
that person, Gary Two. Who is actually Gary Two? The clone version, or? Anyway, I would take the clone version and I would make that person spend every waking moment with my family. They’d sit at home, you guys, what’s that? (laughs) Why is that funny? – [Steve] I thought it was a nice answer. – [DRock] I would send
the first one first. – What’s that? – [DRock] I would send yourself. – Oh, I don’t care. Keep this rolling by
the way, first of all. No editing here. No, no, I don’t think you understand. The fact of the matter is
is they’re the same person. Are you saying that, no but listen, maybe that was
an insight that we didn’t, maybe I love my business
more than my family. Sorry, this is a tough way
to end the show and the year. The bottom line is, sorry
that DRock has become the cynical one, but, Steve, the torch has been passed, I would take the equal version of it and have that person
sit at home every minute and be with my family because then I would be able to accomplish the
two things that I want at one time, and so that
would be the answer. (laughs)

– [Voiceover] Antoine asks,
“What keeps you up at night?” – Antoine, that’s a very
quick and easy question, literally, and I think
at some level the reason I took this question ’cause it’s not– I’ve probably even addressed
this before with VaynerNation, but every so often it’s a worthwhile venture to bring it up again, which is the only thing that keeps me up at night is the things that I can’t control and the only thing that I can’t control that really cripples me is
the health of my family. The health of my family is
what keeps me up at night, which is just something I can’t control. I can do everything right, but an accident or something unfortunate or a disease that we all hate so much can come along and change the course of my life. When it comes to business, when it comes to my relationships, I
feel in utter control and I really, really recommend
to a lot of people here… It’s amazing to me in
the stress-filled world that I live in, by outside
standards, my calendar, what I’m trying to achieve,
my own stress on that, all the things that are pulling at me, none of it stresses me because it’s gonna be what it’s gonna be. I’m gonna execute
against my skill and some of the serendipity that
comes along with the game and I’m very comfortable
and zen in that game. But the thing that does bother me, the thing that makes me
upset or I’m concerned about is 100 percent the
well-being of my family. – Gary Vaynerchuk, I have
an #AskGaryVee question.

– [Voiceover] Michael asks, “Hope you had “a great time at last
night’s holiday bash. “What’s your favorite holiday tradition?” – Michael, hands down, my
favorite holiday tradition is Thanksgiving, just
goin’ to my parents’ house in Hunterdon County. It’s just somethin’, I
don’t know, I just love it. Obviously, we talked about
it a couple episodes ago, but it’s really just you know,
I think you get the theme, it’s happened twice here,
I’m a people person, I’m a family guy, that’s the one that’s almost like the non-debatable. My dad screwed up birthdays
a couple years ago by taking my mom to Italy on the birthday and breaking up the family dynamics, and now I always razz him for that, because then I had a really
dear friend get married during my mom’s birthday,
and we went away, and so now it’s broken up a little bit. Birthdays used to be pretty sacred. The family shifted a
little bit on that one, but Thanksgiving is like,
“We’ve got to be together, “we’ve got to be at mom’s.” And it means a lot to me, I get to see everybody I love so much,
and there’s so, you know. The football games, and the me and AJ doing something crazy like we bought expensive basketball cards this year. You know, just, it’s always a lot of fun, my sister’s kids, blah
blah blah blah blah. So, Thanksgiving, getting together, nothing too crazy, nothing
too, you know, wild, but that’s the scoop.

– [Voiceover] Jimmy asks,
“What’s your favorite “city in the world to drink wine in?” – Jimmy, my favorite city in the world to drink wine in is the city that has my friends and
family in it at that moment that I’m sharing that wine with. There is no, like you know, atmosphere that dictates my happiness of drinking wine, there’s
no pretty french riviera, or the gorgeous mountains,
I don’t give a crap about that stuff, what I care is who am I drinking it with? So, I could be in Newark,
big ups to Newark, not dissing, if it’s with somebody I love, and we’re enjoying wine, then that’s what is the driving force,
and so then it would be Newark, the hotel lobby in Austin, in south by 2007 is one
of my favorite times of all time of having wine. The parking lot of a Jets game, you know, inside the caves of wineries in Tuscany, like it’s happened in a lot of places, but
it’s never been the setting. I don’t care about that stuff. It’s been the people I’m sharing it with. – [Voiceover] Bill asks, “I’m
in sales for third generation

– [Voiceover] Pressian asks,
“How exactly did your mother instill that self-confidence in you?” – And finally, Pressian, thank you so much for
asking this question, ’cause I always love
to brag about my mama. She she instilled so much self-confidence in me because of a couple things. One, I probably had some
level of it in my own DNA, but she brainwashed me. My mom made me think that
the things that I was doing that many parents, on the negative side, put down their kids for, what the far majority of
parents would consider mundane, like getting a good haircut or, like, running quickly to pick up the ball, like it was so athletic, stuff that none of you would ever think is the kind of thing that you
would compliment your child for, the kind of things I compliment Misha for, which is the greatest
twirl I’ve ever seen ever, is what she did for me, and you know what? You start believing it. I can tell you this, and I’m positive of this, I know that the peeps in this room think more highly of themselves today than before they started jamming with me. The reason this company is so special, one of the funniest things
that happens in this company, is when somebody comes
in new that’s senior and they are completely flabbergasted by the confidence of the
youngsters in this room. And I bet you, as they’re all
thinking about it right now, and obviously Staphon and India
are here a little bit less, and DRock a little bit in the middle, and Alex a little less,
and Steve a lot more, I know that that’s what I do, maybe not to the extreme
level that my mom did for me, obviously it was very focused, one child. We have many children in the house, but I would even say that many of you have started to feel that way, because the truth is, my friends, positive energy is a good thing. I don’t know what else to tell you. And when it comes from a pure place, it’s double good. And so she just focused on it. It’s in her and the way that
it’s in me, we’re similar, and she just kept pounding
me and making me feel like the ordinary was something
that was extraordinary, until I finally believed it so much that that’s what I feel
about myself all the time. And if you don’t have good
empathy and self-awareness, it can go into a very dangerous place, but if you know how to balance it, and my mom balanced it by
punching me in my mouth with her raw hand, not kidding, when I
would do something wrong, so she’s got a little old-school
Eastern European in her, and that’s how she did it, with an enormous balance of just good stuff, man,
really good parenting. Really, really, really good parenting.

that you want to complete before 40?” – Gabii, this is a good question, one that I was excited to answer mainly because the truth is, I only have one bucket list
item in my life professionally, and that is to buy the New York Jets, and thus I don’t have any bucket
list items professionally. Personally, I don’t want to
climb any goddamn mountains, or jump out of anything.
I’m not that dude, so I don’t care about that, the bucket list item, you
know, on my personal life is quite basic as well, which is, I just wanna love my family, and I’m executing on that
and accomplishing that, and so the answer is no, not before 40 or 50 or
60 or 70 or 80 or 90, and the truth is, and this may actually lead to why I’m so happy, the two bucket list items in my life is to love and cherish and
make my family proud, and to live the process of
buying the New York Jets more than buying the New York Jets. And I’ve actually accomplished both. Which puts me in a good mood.

“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.

– 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