– [Voiceover] Yash says,
“You changed the intro music. “Why?” – Yash, cuz.

“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.

– 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

“If it wasn’t for the 14th amendment, “would you run for President?” – Chris has a tremendous question to end the show. The answer is I would run for President. It’s really funny. And the reason I’m laughing about this question is Chris, you’ve set me up to expose a dark part of me, which is the selfish part of me, ’cause we all have it. The singular reason that I’m probably not already having a serious eye on politics is because I can’t be President, and I am not willing to as a human being, play a game that I can’t be the ultimate winner of. And many of you are gonna leave comments on the YouTube channel
or hit me up on Twitter, you podcasters and say,
“That is not noble, “you could be a governor and make “a huge impact or a congressman “or mayor or you know.” And I understand that. But, that’s not what I want. I’m selfish about that. And so, yes, if they changed, if Schwarzenegger followed through on what I wish he could have done, but he couldn’t, if somebody comes along or they change it, not in the current environment, clearly, I would put myself into that game, because, I probably pride myself on the singular thing that I think when things are a worst, I’m best. I eat pressure for breakfast. I love it, I need it, it’s why I love HR. it’s
the ultimate pressure, people hate that kind of pressure. So, if you look at the hairlines and the color of the hair of Presidents, of when they start to
when they’re finished, they looked like they aged 60 years. I’m already aging with my hair, I want it all gone. I just can’t play that game. And so the answer very
simply is, yes I would. And that leads me into the question

– [Voiceover] Thousand asks, “Who is your favorite comedian?” – Thousand Moments, let me give you that answer, but before I do, Steve, ’cause I love you so much, show him, show him. Tell everybody what you just said before we did the question, because, you had a good rationale for ruining the show’s audio. – The noise that I made
during the last episode was because I was pulling
up Paul’s YouTube channel, which is a Minecraft channel
by the way, so, well done. – Cool. Now that I found out
it’s a Minecraft channel, you may want to change that up because that is one competitive space. Alright, my favorite comedian of all time. I would probably say that it is a tie, because I wanna give– It’s a three-way tie
between Richard Pryor, Eddie Murphy and Chris Rock. And now, if you go back and watch all of my keynotes and watch its cadence, you may see where the
influence comes from. – [Voiceover] Nasir asks, “Sometimes my passion
is seen as aggression.

“of hip hop, were you East
Coast, West Coast, or both?” – Robert, Biggie changed
my life so I’m East Coast. But I will tell you something. I’m gonna throw you for a real curve ball. Specially cause it’s good
times in Cleveland right now. I’m a little bit more Cleveland. I was all in, I mean like let’s
put all the pieces in here. I was all in on Bone Thugs-N-Harmony. Take me to the cross roads, every time East 99 is
where you’ll find me. So I’m a little bit more Cleveland.

– [Voiceover] Joe asks, “With
the NFL in London this week, “what do you think about sports franchises “moving to different cities or countries?” – I think some sports
franchises should go to very far away places, like
as far from here as possible. This was episode 25 of
the #AskGaryVee Show.

“Why is your phone always in the shot?” – My phone is always in shot, because my phone is always with me. Plus, my adorable Xan’s on there. I don’t want to show his pictures, he doesn’t want me to
share kid photos that much, but the other reason is
because if you haven’t heard, this is an extension of
you as a human being. Every one of you, rarely, is ever, arm’s length away, from your phone in every 24 hour window, including while you’re
sleeping and showering. This is an extension of us. This is, ya know, eventually
it’s gonna be here, and here, and then helmet, and then eventually, directly in us. This is the extension point and so it’s always with me, because
I need it to be a human. That’s right. It sounds sad. Plenty of comments coming, like, ugh, but that’s just the way it is. – [Voiceover] Swelldesigner asks,

“helped you innovate in marketing. “Do you think any of
your areas of expertise “hold you back from innovating?” – Jared, thank you so much
for making the #AskGaryVee Show what it is. For all you hardcore Vaniacs, and I’ve appreciated all
of you, and by the way, all the new lurkers, that means the people watching this show on YouTube
or natively in Facebook, ’cause that’s the way
I’ve been putting it out, and are not leaving
comments are pissing me off. So lurkers, episode 19, get your asses in the comment section. It is the fuel that helps me continue to do this show. Jared, thank you for
making this show what it is and what I mean by that is,
so many of you have heard, if you’re hardcore about me, which is that that Medium post like,
maybe you’d wanna put the picture up here like, you know, me failing all my classes is why I’m good. My lack of reading, my lack of knowledge of a lot of things, that
keeps me very creative ’cause I’m not folding into things and using the same thing over and over, there’s that, it’s a big advantage for me. My lack of education, IQ knowledge on a lot of subject
matters, really helps me. And so for the same
reason I say that, Jared, the answer is yes, the
things that I believe in or I’m more knowledgeable
about hold me back because they get entrenched in my brain, I believe them to be the way they are. Now, because it’s in my soul to fight and to counteract and to go in the grey, not the black and white,
and all that stuff, I think I maybe get away
with it a little bit more, but truth is, I’m still human and yeah, those things are holding me back. – Hey Gary, my name is Mark Cersosimo.