important observation you’ve ever made in your life?” – Sean, I think the biggest observation I ever made in my life was I needed to really trust my intuition over what I was being sold by anybody. From my parents to my teachers to the television. I just, you know, I always talk about betting on your strengths. You know, for me, and you know, maybe most people are different. Like, everyone’s different, but for me, you’re asking me, the #AskGaryVee Show, that’s
why we called it that. For me, it was just
somewhere in my early teens, it was just obvious to
me that I was right. And I know that’s an
obnoxious thing to say, but my happiness and success always followed me going down the path that seemed obvious to me, yet I was confused why everybody else wasn’t, it wasn’t, besides my mom, it wasn’t so obvious too. And so I, that’s what I would say. I would say that’s my answer because observation was I was right, don’t be scared of what that meant, have the confidence to
follow through with that, don’t hedge, don’t, respect other people’s points of view. Have the humility that has been such an important balance to the gift of the intuition, but never
waver, never waver.

“Gary, how do you maintain
a good, pleasant mood with family after a long day of hustle?” – Sandy, great question. India, was it you replied
in email who’s like, yeah, I wanna know that answer too? Look, here’s the thing. You know, this is only one person, I’ve always had, and my
dad did not do this well, and maybe that’s why it affected me, I am so grateful and so thankful to the family members that allow me, my wife specifically, allow me the freedom to hustle the way I do. I feel like it’s totally inappropriate to disrespect that
love, to then carry over my headaches home, in general. And this is something that
the people that know me best, the nicest thing they can say to me, and it happens, you know,
it’s been said to me 12 times in my life,
nothing, but my best friend, Brandon, who runs
Wine Library, my mom, my sister, my wife,
AJ, my dad hasn’t, anyway, there’s been a couple
people that have said to me how much they admire that
I never take my headaches out on them. I think it was really,
at the end of the day, two people, people that need somebody else to dump their headaches
on, and people that collect those headaches. I admire my mom tremendously, she collects everybody’s headaches. I’m very thankful that I took that DNA. I’m thrilled to hear your headaches, but I have no interest in giving you mine. And so, that foundation, that DNA trait allows me to walk right in home with all the insanity, lost this client, cash flow’s not as good, problem, can’t ship to this state anymore, didn’t get that deal,
this deal fell through, didn’t get that opportunity, number two in the New York Times, you know, something way worse than that, like, somebody’s leaving that I don’t want, somebody’s sick that I don’t to be sick. All these things that
are life and are intense, the second I walk in that door, I need to repay that amazing family that has given me the
opportunity to do my thing, I need to shut that all off
and turn on a different gear, and the truth is it’s just easy for me. No different than when Kobe, Staphon, let’s Kobe, show Staphon, you know, when Kobe goes on the court, he becomes a different character. That’s how, I’m very much like that. On stage, different dude. Right now, different dude. Running this company, different dude. Walk in the house, different dude. And so, I just have a lot of gears. I gear it up.

and on a recent podcast of Carl and Mike, we answered five of your
questions of the day in five minutes. So, we want you to answer one of ours. – Just one, Gary Vee. – That’s it. – [Voiceover] Carl and Mike ask, “Gary, what do most people want
to get out of social media?” Carl, Mike, first and foremost,
I just instructed India, let’s show India, you know,
because India just told me an awesome story that
like, people are starting to recognize her from the show. You’re India from the #AskGaryVee Show? I love that. Carl, Mike, listen, it’s very simple. What people want out of social media completely maps to what
they want out of life. They’re, you know, social
media, internet life, internet culture, I was
saying something the other day that meme culture has taken over culture, I was talking today to
the VaynerMedia team, you know, because the internet is life. And so, what people
want out of social media are the things they want in real life. They want the fame and notoriety, India, they want, you know, they want this. You know what they want
out of social media? They want this, my friend, right? ‘Cause they want this in real life. They want a place to express their art and show the world their art, India. You know, and so like,
these are the things that people want, exactly
what you want in life. What do I want out of social media? I wanted to interact with more people, I wanted the vanity of being
like, are you Gary Vee? Sure am, you wanna take a selfie? Like, I wanted to fulfill the
things that were in my heart getting out there, leaving a legacy, not realizing how much I loved to teach, but that’s what Wine Library TV and the #AskGaryVee Show
are, who knew? F student, A teacher. And so, like, the things are
really interesting to me are that people want what they actually want, and what social media allows
them to do, my friend, is use the backbone of the internet to cut out the middle of the gatekeepers that used to keep us away from that. Who the (beeping) would have hired me as a college professor
teaching marketing? No one. Guess what? That is what’s interesting about the world we’re living in now. Direct the consumer, my friends. You wanna watch me on the show? You wanna follow me? How many people are on Meerkat right now in the middle of the day? There’s 318 people that are
busy in the middle of the day, get back to work, that
are deciding that this is valuable to their time. A bunch of people are about to reply, this is work, and you’re
right. This is good content. I appreciate it. And so, that’s what it allows to do, it allows to actually map exactly what you actually want
in life ’cause you have no restrictions to actually achieve it. – [Voiceover] Sandy asks,

Not old like that. Don’t get crazy. Here’s my question: Why do you think men should aspire to date a rich bitch? – Hey Nicole, big shout out to you. I know your book’s out. I took this question because
you are an old great friend and I wanted to give
exposure to your new book, so DRock, let’s link that up. I know you’re doing super
well with your book, and I think we talked a little bit about, the book is about really
financial stability and financial smarts, I
think, that a man should marry a rich bitch or
be in that situation, or a woman should marry a rich bitch dude for the same reasons that, having a stable financial partner is always a good decision in life. People that are unable
to manage their money deal with so much stress, and money is not the most important thing,
but when you don’t know how to handle that, there’s
an enormous amount of stress that comes along in life, and it’s not about how much you make. There’s plenty of people
who know how to manage their money making $37,000 a year and have a lot less stress than people that make $140,000 a year
and don’t know how to manage. To me, I’m anti-stress. Money management is at
the tippy top of the list, probably right below the health
and well-being of family, and that would be the core reason. – Yo, Gary Vee.

and I was just curious
if you ever get sick. Maybe you really are Bionic Man. If you do get sick,
how do you handle that? How do you hustle when you’re sick? Really sick. – Ryan, first of all,
hope you feel better. I mean you look like shit in that video. First of all, big shout
out to Lizzie Vaynerchuk because in the last 11 years
that I’ve been married, I have not been sick. I think that has a lot to do with the fact that Lizzie tries to
get me to wash my hands and the fact that I don’t
have a weird draft coming in like I had in my old apartment, which I think caught me a couple times. I mean… You’re talking to a old
school Eastern European kid who actually thinks that
getting sick and being sick is actually psychology. I think the brain is
the most powerful tool. Like, I know the answer
to this is not true, but I do feel like… I’d be lying if I didn’t
think there’s some way that I’m stopping myself
from getting sick. In the same way that I used
to be able to get myself sick to get out of school,
and I don’t mean like, “Oh, my tummy hurts.” I mean, in this weird, yeah, I’m going somewhere. I’ve never said this out loud. This is actually even
scary to say out loud. I’m so convinced that the
brain is this powerful, I used to be able to create a temperature, and I know that every logical
person, including myself, I literally just said, “Bullshit,” but I saw it. I mean, and sure, sometimes,
I put it up to the lamp and that’s how I did it, but
there was a couple of times where I would just psych my… Even right now, I just started doing it, and my stomach turned a little bit. I’m not kidding! Guys, the brain is a sick thing, so I guess the answer to
the final question is, you don’t hustle when you get sick. In the same way you don’t
hustle when you get sleep. We’ve got that quote card
that did really well, right? That quote where I’m like,
“It’s not what you do, “it’s not how many hours you’re awake, “it’s what you do within them.” I’m thrilled to get six
or seven hours of sleep. I love when people think
I’m a three or four guy. I’ll take eight every night, because in those other 16, I will dominate your face. I love people who sleep
four hours, but chill, and chilling is just not
doing something important for 40 minutes or having a
conversation on the trading floor for 30 minutes about the big game or what the fuck happened
in the Oscars last night? Who gives a shit? Execute, and so, but wait, who did this shit for me, I’m
purely focused on my thing. Some people like 30 minutes
of talking about the Oscars ’cause it breaks up their day. That’s their rest. You do you, but let me say this. When you’re sick or when
you’re sleeping, rest. Your body’s telling you something, and so, like weirdly, maybe I was sick
once in the last 11 years, I was pumped. Let me just say that
again ’cause I don’t know if everybody understood that. I weirdly wish I was
sick one day this year. I would really enjoy the time off. I’d enjoy relaxing, and the kids come. Misha comes home at three, it’d be fun! It’d be fun, but there’s something subconsciously that’s really trying to
not allow me to do that. In a world where I take
a hundred-plus flights, where that place is like, I don’t know… Remember how a couple episodes, I said that the 20- to
30-year old Gary Vee is soft compared to me? That guy did get sick. Now I don’t, and I do think it has a lot
to do with my focus on it, so I do think you can
out-hustle your sickness to some degree, but
when you succumb to it, because at some level, we all do, I think you need to
just relax and enjoy it.

– [Voiceover] Apollopoetry asks,
“When all is said and done, “how would you like to be remembered?” – This is a tremendous question. This finally put me in a decent mood. You know, look. I think, I think that selfishly, I would like to be remembered as the greatest human being
that ever lived the Earth. (bell rings) You know, we’ll try to
keep it basic and modest. You know, I’d like to think that, I’d like to think that
people appreciated my effort, in whatever way they define that, right? Like, the hustle culture
that I’ve created, that you know, is clearly, I’m so humbled by the notion that it’s inspired people to
work harder and create things, but like, the effort on
like, on an individual level, and like, all the behind the scenes stuff. Like, look, I often say, I live my life on a daily basis, with the complete intent to have everybody that I interact with, show up to my funeral. And I think the only way you can do that, is to be remembered as such a good person, that you created guilt, that people have to go out of their way on their busy days to
show up to your funeral, even though you only met twice
in two business meetings. And so how do you do that? You become memorable. I take advantage of like,
my extroverted personality, and like, the charisma that I was gifted, but I think you need to
back up that sizzle, right? And I take a lot of pride in my ability to be a practitioner,
and my ability to do, I’ve gotten better and better and better at like, keeping my word. That’s always, you know, tough, because, you know, I would
have all these ambitions, and I’m always on the offense, and that is something
I’ve gotten better at. You know, so I guess, you know, just a good human being who cared about, who cared about more
things than just himself.

– [Voiceover] Hamms
asks, “If you could have “a bionic body part, which
body part would it be, “and what powers would it have?” – The truth is I do
have a bionic body part. My right leg from the knee to the hip, and then the hip all the way in is made out of titanium. – I didn’t know that. – Yeah, most people don’t. And the super power that it gives me I think I can make this, but
when I was in the hospital, my leg broken in like,
literally, 27 places, and they were hammering
it back together made out of metal, the doctor said to me, “You know, you’ll never run again. “You’ll be able to like
catch up with a taxi cab, “but you will never run again.” And I was 26 years old,
and that is a tough thing for a 26 year old to
hear, especially someone as physical as I am. So, the superpower that it gave me was prior to that, prior to getting my bionic limb, I wasn’t much of an athlete or a runner, but since getting my metal leg, I’ve run 22 marathons, and
four IRONMAN Triathlons, and countless other races,
and I’m a much fitter, faster person since getting my bionic leg. So it has, I do have a bionic limb, and I do have a superpower. – I also have a bionic limb that no, no I don’t, I really wanted
one though, I’m pissed. – I was excited to hear what limb, what you were gonna go with. – You know what, I would go with ears. I’m not joking, I’m very intrigued by the notion of like, I
love picking up senses right, and for some reason, so one of the things that I think I do extremely well is I, that I really enjoy being able to do, and I’d love to do more of, which is why I’m going with ears, is I am often at a dinner table, or at a conference, having a conversation fully in it, and capable of listening
to the two or three other side conversations,
as a matter of fact, often when I talk to a small group of 40 or 50 people, I
will use side whispering of what I just said to
incorporate into my talk, and then look at the person,
and they’re always freaked out, because I was so focusing going here, but I heard them, and so I think people don’t listen enough. That’s
a big thesis of mine. It’s my overall social media thesis, and so I’m gonna go with ears. – I’m just picturing Gary
with gigantic, titanium

“when you pissed someone off. “How badly did you piss them off, “and what did you do to make up for it?” – This is a really interesting question. – I work so hard not to piss people off. – Oh man, me too. I’m like suffocated by
pissing someone off. I’ll take this, pissing someone off. So look, I mean the only
time I’m truly ever affected, ever, by pissing someone off
is when I piss myself off. So, it’s a little bit
of a wrinkle, meaning I am so aggressive to try
not to piss off anyone, that the second I taste
in the water that I did I start hedging like a hog. You know, like I start like really, did you get that Sonic
Hedgehog, good alright, you got it (mumbles). I’m in full apology mode immediately. The only time I even am comfortable pissing people off is on stage when I’m challenging the audience to the quid pro quo, so I’m, on a one to one basis, I’m crippled by hurting someone’s
feelings, and the second that I sense it, I start backtracking. So, the way I answer, the way I fix it is by immediately taking
the gas off the pedal, cause I don’t like that feeling. I think there’s other ways
to manipulate my point. That’s the truth, I truly think that I can drive home my point
through honey, not vinegar. – Yeah, I agree, I mean
there’s no worse feeling than upsetting someone else. And that said, because I
have a very specific image in my mind when I think
of pissing someone off. But I can tell you that living life where you pander to other people to make sure you never have enemies or never have anyone dislike you is a very dangerous game to play, and I’ve always said with my work that I’d rather, if 100 people see a movie I make, I would rather have 50 people love and 50 people hate it than have 100 people go, “Eh.” So, it’s a fine line in that
idea of pissing someone off can mean so many different things. The last time somebody
walked away from me angry I honestly can’t remember,
but the last time I read the YouTube comments
on any one of my videos and they were 100% positive, well there was never that last time, cause I don’t think that’s ever happened. – Yeah, I mean, that just
made me think of Linkedin. Boy, does the conservative
business world hate where I’m coming from. You know, it’s funny,
I’m sure a lot of people are watching right now and saying, “What?” My living is being in the minority on my points of view, on the current state of marketing and all that stuff, but I’m with you, like on
a one to one basis, never. As little as possible, to
the masses, no problem. And I think that’s an interesting insight. – Yeah, I think so, cause as a human being the ambition is to never
piss someone else off, or to leave someone else upset, but as far as a belief system.
– For sure. – The belief system has
to be uniquely yours, even if that’s a divisive… – I will also say I’m in the sport sense, like in competition, I’m very interested in pissing people off. I’m, you know, it matters to me a lot, like nothing excites
me more than if I know somebody’s upset because
I did something positive for my team versus theirs. It’s extremely interesting
to me to piss people off during the heat of battle
because I want to get them emotional and off their game. – Yeah. – Yeah, alright, let’s move on. “a bionic body part, which
body part would it be,

– [Voiceover] CJ asks,
“How has having a family “changed your long term view of work? “And what does retirement mean to you?” – CJ asked a good question. I’ll let you go, cause I know you’re a new father of a second. – Yeah, so what does family
have to do with work? I think family is the ultimate cheat, and what I mean by that is I had a kid when I was 16, I’ve always had a family since I was an adult, my entire adult life I’ve had a family, and it gives you a reason
to do all this work, and that downtrodden feeling you can have, which is like, “Why am I doing this? “Why am working another night
til three in the morning?” When you have family, for
me, it gives me my purpose, my reason for doing
everything I do is my family. Part two retirement,
retirement’s my biggest fear. Retirement is what people
do when they wait to die. My grandmother was a tap dancer, and she had a tap dance school, and she taught tap everyday of her life, and she taught tap on a Friday, and she died on a Monday when she was 92. That’s my fantasy. I want to work until the last minute, I want to be working in my
hospital bed as I’m dying. So, that’s how I feel about retirement. – I’ll start with
retirement, I’m you know, in the complete same camp. You know, that is my nightmare. I want to die on Monday, on
the Monday that I’m working. I didn’t need those two days in between. You know, I’m with you
I think, you know look, I will say this, there’s one weird retirement fantasy I have, which is to be an old man sitting at the racetrack, having some nickname like one eyed Gary, and
like betting on the ponies. I do like the notion of
the ponies as an old man, so there’s a little bit of that. You know, the family, work
life balance whole thing I think is completely counter punching. Meaning, I hate giving an answer to this because I think it really is
predicated on your partner, and then the evolution of your kids. My partner part I really
kind of took care of. I mean, I was looking for Lizzie, when I found her, I locked her up, married her immediately, we were married within the year of meeting. I told her on our first date
that we were getting married. I knew that she was independent enough and could, I intuitively
felt that she could handle the insanity that is me. It’s crazy, I feel like
we’re still dating. Because you know I travel so much, and like I’m busy, but like
it’s just over communication. When I see a little
strain, I’ll cancel a trip, I won’t say yes, you know, I try to hack, the kids are a whole new variable. You know, now that
Misha’s five and a half, I’ve got to get ready for: They may not be like Lizzie. You know, my little Xander might want me at every single thing at every moment. So, I’m starting to get mentally prepared to counter punch their reality. Kids are always going to
want their parents around, but what’s the hack, right. Like, do I, like it’s
funny, I’ve been traveling, and where I speak now, I spoke in Anaheim and I noticed that Disneyland
was right next door, so I’m like, “Maybe I’ll do
these speaking engagements “cause I’ll take the kids,
let them see what dad does, “and then a full day of…” So, it’s interesting how my brain is starting to adjust to: What’s their reality gonna be like? So, my answer to your question is counter punching, what I mean by that is gross over communicating. Having those conversations
with your spouse or with your partner,
having those conversations maybe even at an early
age with your children. – [Voiceover] Shay asks,
“Think back to a time

your brand with the public. How personal is too personal? Where do you draw the line?” – Kyle, I think for
everybody it’s different. I draw a line heavily around the kids. I don’t do a lot of stuff
with Xander and Misha, but I’m also thrilled to put out a picture of me being on the toilet. Everybody’s got different lines. Some people are very conservative. Some people are extremely aggressive. Some people take photos nude, some don’t even wanna
show their belly button. Everybody’s got their own objectives, their own agenda, their own
North Star or what’s too much. For me, I just always go on gut feel. What may be too much
last week might not be too much tomorrow. I don’t really I don’t really second guess my feelings. I’ve done pretty well with them. For me, it’s what I’m
feeling of the moment. I like getting personal. I think it allows people
to get closer to you. I love doing this show for that reason, and so that’s where I’m at. – [Voiceover] Autumn asks, “I
wondering what everyone thinks