– [Voiceover] James asks, “Do you schedule time to be on social media? Or just jump on randomly during
the day as you have time?” – James, I don’t schedule crap, other than I completely live on my schedule meaning my admin, Matt, he
schedules my whole life. But if I was to be in control, I would not schedule anything. There has never been, you
guys all have access to me, there’s no 15 minutes get on social. Social’s in me, it’s not a
tactic, it’s my religion. So I do it every moment I can, it’s always top of mind
to be with my audience. I’m reading your comments, I’m reading your guesses on the almonds.

Thank You Economy will
self destruct in 2015? Are brands living up to your
predictions slash Thank You Economy expectations?” – Tyler, once again, and I
talk about it all the time, I think things are gonna
happen sooner than they become. My prediction in Thank You
Economy was that people would understand this and
then everybody would do it. And by 2015, it would get ruined. I am so off on that prediction
it’s borderline embarrassing. You know, DRock, I don’t know,
can you like, take my face right now and give me like, rosy cheeks? Like, can you like make
my face red right now? Because I’m so embarrassed
by how off I am. Because, two part. One, people just haven’t
adopted the Thank You Economy. And thus, if they haven’t
adopted it and scaled and ruined it, how can it be over, right? And so, it might take a lot longer. It may take forever. More importantly, the people
that do attack the world in a TYE world are getting dividends. I’m getting those emails. But it has not been the
landslide that I had hoped for the consumer. So, my prediction was obnoxiously off. One, it may not happen,
at scale because companies are just heartless and
just don’t understand the financial benefit. And listen, I’m heartless. I mean it’s all about the wallet with TYE. I mean to me, it’s, this
is how you do business. And two, it’s not enough at
enough scale or ruined yet. People are still flabbergasted
and excited when a business acknowledges
them or does something half-assed caring. – Hey Gary, this is
Kyle @JockNerd and Ruby.

“when you were 25, how
did you overcome fear “of not doing as much or
not having it as hard?” – TJ, this is a great question. In life, there’s certain
things that you can control and other things that you can’t. One of the things that
really stand out to me is how much I, this is something I’ve rarely shared. I think I’ve shared it once or twice, Stunwin, keep me honest here. I’d be curious if you know. I think I’ve talked
about it once or twice. I often, when I was 18 years old, would call my mom while I was in college and cry, literally cry, like a baby, get that emotional about the fear that, at that point, I thought I was going into the family business, right? I was in a crap college. I was all in. I was going home every weekend working, and I had a huge fear
that I was never gonna get the credit I deserved as being, this is, ya know, the confidence inside, by going into my dad’s business because everybody would always
say that Sasha gave it to me, that my par–
look there’s even in Crush It!, there’s even negative
reviews on Amazon of like, “Oh yeah, but his dad gave him “a 3 million dollar liquor store.” Now, you know, as, I underestimated people’s knowledge that a three million
dollar revenue liquor store is not a three million dollar grant, and things of that nature, and then obviously my skills. I said recently in an episode, a lot of you caught it and tweeted it, “The truth is undefeated.” If I was gonna be a great businessman, I would get the credit that
I desperately, clearly wanted at that age and still at this point do ’cause the narrative does matter to me, not just the dollar results. And so, it’s interesting, this question really struck a chord because I remember not
only having that feeling, but I had a separate feeling which is the answer to your question. The answer to your
question is very simple. One, I knew that I would never have it as tough as my parents, so what I did was I had to execute against that privilege. Executing against your privilege is the only thing that you can do. I remember two things
that stand out for me. One, growing that family business. I wanted to pay back my
parents as quickly as possible. I, the greatest two
feelings I have in my body as an entrepreneur, answer this question. One, the fact that me and
my parents walk around and all feel like we’ve
given to each other. I paid back, right? I built such a big business
that it helped them as much as it helped
me getting that at bat. And number two, the day my
dad a couple of years ago maybe 18 months ago, said to me that I work harder than him, and that was a good feeling. That was something I wanted because that was another way
to pay back my privilege. The fact that my dad sacrificed
his entire life working to set up the foundation
where our family is going is something that I wanted to
pay back by doing the same. Now look, to pay that
back, I also want to have a better work life balance, to
spend more time with my kids, something he wasn’t able to do. So there’s other things
besides just working hard, but the fact of the matter
is the only thing you can do is to execute against your privilege. – [Voiceover] Joy asks,
“What social media techniques

“What are your pet peeves? “And what skill do you
wish you were better at?” – Elliot, great question. My pet peeves are pretty basic, meaning they’ve been
there for a long time, and it’s something I’ve
talked about in the past if you’ve watched any of
my key notes or the show, I think I’ve sprinkled it in, but I wanted to kinda address it, and it’s really funny,
I’m even pausing right now and buying myself time because the second part of your question, “What would I like to be better at?” is a struggle for me to come up with, and maybe that’s the answer in itself. We’ll get to that in a second, but pet peeves are clearly
hypocrisy and cynicism. I hate the cynicism in the marketplace. Steve feels it’s a must-needed
thing, and I respect that, but I won’t focus on that ’cause we’ve done that in the past. It really is hypocrisy. I have family members, I have
people I’ve done business with who are so hypocritical. It kills me. They literally like talk, and by the way, the reason I answered this question is a lot of you in the comments and a lot of you listening
on the podcast right now that are interacting with me, you talk a good game about community, you know, I’ve been doing
a little bit of digging, I’ve been thinking about
making kinda this slideshare which, oh by the way,
link up the slideshares. We haven’t done some linking
up in a little while. Linking up is a much needed thing. The slideshares that I put out. Been thinking about doing a
slideshare on bull (censored). The hypocrisy of people tweeting like, “Be in your community. “Engage with your community. “Give for your community.” And then you look at their Twitter feed, 4713 tweets all time, and nine at replies. I have a lot of pride
with my at reply ratio, and so those two things
really stick it to me. What would I like to be better at? Look, you’ve all heard me
if you’re hardcore fans that I say that I’m 99% of things suck at, and I believe that. There’s a lot of things I’d like, I mean, I’d like to be able to, look, I’d like to be able to sit
down and read something for more than two minutes and
actually concentrate and do it I mean, this poor crew, and show them, because I wanna show how poor the crew is, and I don’t mean financially, I mean, how I feel bad for them
because they sent me these nice long e-mails,
and then literally after the fourth time they send
it, I’ll reply and just say, “Let’s just meet for five minutes.” ‘Cause it’s so audio for me,
and I struggle to consume, and there would be a lot of efficiencies if I was better at consuming,
so kind of that ability to concentrate on things
that are not that important. Take that the way it was meant, guys, which is, ya know, I can concentrate on a one, two percent kind of variable, but I struggle when I
think things are important, but not that important. – [Voiceover] Amanda asks,
“What ways can agencies

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

“how did you structure your day?” – Yoli, first of all, I
just wanted to tell you I appreciate all the interaction. Thanks for being a supporter
of The #AskGaryVee Show. By the way, back to the last question. The middle is dangerous. Pre-assistant. I mean, it was a disa– I was such a bad person, you know, I had this power position at Wine Library, where I was one of the biggest
wine buyers in the world, or definitely in the U.S., in the world. And nothing got to my
head, but I was like look, somebody can wait 15 minutes or 20 minutes if I’m like, you know,
finishing up this meeting. They’re here to sell me. So I kind of took the, you
know, the buyer’s approach mentality to that. But what was bad was I
would triple book people, like literally, I used to
be like on floor at 11:30 in the morning helping
somebody with, you know, a big selection for a
party, and I’d see like somebody walk in, and be
like oh yeah, that’s right, I have a meeting with Craig. And I’d be like yeah, you
should try this Pinot Noir, and then I’d be like oh crap,
why did Frank just come in? That’s right, I have a meeting with Frank, and I think it’s at the same time. That’s bad, let me figure
out what I’m gonna do. And by the way, you need a
little cheese for your party. Why did Sally just walk in? Holy crap, I’m triple booked,
and this would happen a lot. And it was complete chaos,
it was disorganized. It wasn’t efficient, and it was piss poor. – [Voiceover] Z asks, “If you were to jump

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.

– 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