“Why is it a crime to like your
own pictures on Instagram? “Why will you be shunned for it?” – Joe, I’m with you. I think, here, on the
#AskGaryVee Show, Episode 103, I do not understand why
it’s politically incorrect to like your own picture. As a matter of fact, starting here, Joe, going forward for the next 10 pictures, as a social experiment, I will be the first person
to like my own photo because self-esteem is cool, kids. It’s cool. (chuckling) – [DRock] See? That’s one of the answers
that I had no idea what you were going to come out with. – I really think it’s okay. I really think it’s, I
don’t think it’s so crazy. I know that people think it’s, like, it’s funny to see the social taboos. But I’m into it. I’m going to heart the
shit out of my Instagram photos going forward. – [Voiceover] Jason asks, “is heading towards one on one marketing?”

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.

brings a lot of rejection
from my family and peers. What are some ways you build
confidence when rejected?” – Destin, which is not
Dustin and is not Destiny, Destin without a Y, or
Destiny without a Y. Well, you know it’s funny. When the question was asked by India, one thing, first and foremost, you want to make sure, the
way to build confidence is be confident in yourself. I want to make sure first and foremost that you’re not selling
something skeezy, right? Like if everybody doesn’t
have confidence around you, maybe you’re selling something
that is not the right thing. So, first and foremost, are
you selling the right thing? Or are you in ponzi scheme world? Are you in $300 ebook world? Are you in full of shit world? If you’re not in full of shit world, take it from somebody who hasn’t been in full of shit world his whole career, but has done things that people didn’t believe in. E-commerce being number one. Wine Library TV being number two, and then really a social media agency, number three believe it or not. In 09, people still debated
that this was a stupid idea. I think that, you know,
this is a tough one for me to answer because the truth is, I don’t give a crap
what anybody else says. As a matter of fact, I’m
wired a little bit backwards. I prefer that everybody thinks I’m wrong. I feed off of that negativity, and I turn it into positivity. Right, like I literally actually prefer, it’s why I like bad sports teams. It’s interesting. We got to, actually this
worked out perfectly. The reason I really would not want to root for the Yankees anymore, I loved being a Yankees fan in the 80s cause they stunk. The Mets were the team of the 80s when I was a kid. I loved the climb, then they became the establishment, and I pushed against it. It’s my overall thing, right? I’m a very basic character. Like, I like coming from the slums. I like being underestimated, and the second I become the establishment, aka the wine world, it
becomes less interesting. Advertising’s becoming less interesting because I’m starting to
be proven to be right, and it’s just not as fun. Like, I want the push-back. So, you and I are wired
differently if you’re asking this question. My question is like,
how do I stay underdog for longer? You know, and so I feed
off of the negativity. I feed off of like, you’re not right, you’re not right, you’re
not right, you’re not right, I don’t agree, I don’t
agree, I don’t agree. That’s not the way it’s always been done. So, I might not be the right person to answer this because
it’s always been in me. In me is the underdog. In me is the scrapping up. In me is the I’m going to
prove you wrong, sucker.

– [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.

– [Voiceover] Mrs. Jones asks, how do you make sure lack of confidence doesn’t stop me from chasing my dreams? Mrs. Jones, this is a very
important question to me because I’m actually quite scared to give you the answer which is we need to seriously think about how to build up your confidence. I am the the kind of person that believes that self-esteem is the
ultimate drug in society. And I believe that when
you have self-esteem, you give yourself the
audacity to dream big aka buy the New York Jets. When you dream big, what ends up happening is the little things
stop mattering as much and you’re not crippled by them and you start really kind of becoming, you know, I’m actually maybe the least anxious person I know in a world where anxiety
should be, on paper, the thing that I most
have ’cause I have so much going on and I have these
enormous aspirations. You know, I really
struggle with this question because I would actually tell you to not say, well don’t worry
about it, you’ll get there. And no rah-rah I can do real quick here is going to affect you, but what I’m hoping to affect you with is I would highly recommend
doing some deep searching into what you can afford and what is practical to work on that whether that’s literally
seeing somebody to build it up, mapping your life backwards, surrounding yourself with
positive, self-esteem driven people, I think is a
very unique way to do it. This is the big one for
me fellas and ladies. I am all in on self-esteem and I would say if you
are self-aware enough to know that you lack it, I would tell you to execute about finding a way to gain more of it. – I’m loving the show, like loving it.

is confidence, skill, and luck?” – Simon, the truth is, you know, and some people don’t like to hear this. Sometimes they say I’m lucky and people get really pissed. A bunch of you will put
in the comments right now. But the truth is, I am a lucky guy. Like, I was born in the Soviet Union. I could’ve been my dad who
was born 20 years earlier in the Soviet Union and
wouldn’t have come to America until my 23rd, 24th, 25th birthday which would’ve put me
far behind the eight ball for what I’m accomplishing. So the fact that I was
born in the Soviet Union during the Cold War
and happened to be born during a time where Israel and America teamed up to make a trade with Russia for wheat. I was traded for wheat
that allowed me to get out through political asylum in the late 70’s and come to America and
live the American dream has a level of luck, right? And so, luck is part of the equation. Now, do I think I’m lucky? I do not think I’m lucky because the confidence
which is great parenting, by the way, maybe a little
luck in that, one could debate, and definitely just kind
of the overall skills and the hustle which is DNA. I don’t know if you can be
taught to work your face off. So, I think it’s just a mixture. I always talk about a great wine. Show Steve, he loves wine. – I love wine. – I always think a great
wine is never 100% Cabernet, never 100% Merlot. A nice little Meritage, a blend. And I think to answer your question, I think it’s a blend of all of the above. Some people, look, I think I make my luck. People are like, oh you’re so lucky that you got into Twitter and Facebook. I don’t feel super, trying to figure out
how I’m getting healthy? That dude. I love his raw, like, he just… – He doesn’t care. – He really’s like the only
person that doesn’t care, that’s what I told him to do. I think it’s a blend of all of the above and I think that that is
something that people need to recognize, feel comfortable with, bet on your strengths, and execute. – [Voiceover] Nick asks, “Do you
think that Facebook is still effective even though it’s pay
to play model and throttling?”