“Where does confidence come from? “How do you both work on it?” – That’s tough. – I’ll let you go first here. (laughs) – Confidence, I mean– – Hold on. – [Voiceover] That’s awesome. – Yeah, I couldn’t (laughs) – You didn’t know the address? – Gary, over your left shoulder
is my electric skateboard. Right there.
– Yes. – I rode that electric skateboard up here. And if there’s one thing you
don’t wanna do while traveling 24 miles an hour in heavy
traffic through New York City, on an electric skateboard
is to whip out your phone and double check an address. – Respect. – So you gotta write that down. – Respect. All right, answer Ben’s question
about your outrageous level How does one have enough
confidence to ride an electronic skateboard 24
miles an hour in New York City? – I have an answer that’s
not really a great one for people to hear, so I’m hoping you have a better answer than I do, Gary. My answer goes like this, I’m one of four kids. There was the first born. The only daughter. And the baby. And then there’s the
forgotten child, Casey. So in my household, it
was like fight to survive. And my confidence was like born into me out of need to just exist
and be noticed and be fed. Now, not everyone has had
the beautiful misfortune that yielded the fortune of my childhood that turned me into a confident person. But I think it’s very
different from someone who finds themselves, as an
adult, in a world that sort of thrives on those who have confidence and being forced to find
that within yourself. But one shortcut I found to
that is making something. Making anything. Whether that’s writing something, whether it’s something creative, whether it’s something more pragmatic. Whether that’s a relationship, whether that’s a friendship. If you generate something
you can take sort of, you take comfort in what
it is that you’ve just made in your yield and I think
that’s a really great shortcut to finding confidence. – Casey, answer– Give me a word association
play really quick here. Fear. – Illness. – Illness? – Yeah, that’s– – I really didn’t want you to go there. Thanks for screwing up my answer. (laughs) For me– – The only thing, being
sick is the only thing that I’m scared of. – By the way,
that’s really funny. Actually, that’s really interesting. Because I was dissing a little bit and now I’m gonna put you on a pedestal. It is literally the health and
well-being of the people I– Weirdly, for me, it’s the people I love is scary ass crap for me. It’s a very big challenge and we all go through it. And so, I’m with you on that. Where I was going with that, is this, I am not scared to fail, by any stretch of the imagination. And it comes in the form of
truly being in this weird place where I really don’t give a
rat’s ass what anybody thinks. And again, that’s wiring. How does one work on that? What do you think I sit– What do you think I go in my room like, “Don’t care what anybody thinks. Don’t care what anybody–” (laughs) Like, you don’t do that. – Yeah, you get made fun
of a lot in high school and it seems like the entire
world is falling apart because you’re being picked on. – I want people to make fun of me. – You grow up and it
realize it doesn’t matter what other people think. – I do, India.
– You really don’t. It really doesn’t. And appreciating that– – It’s like those last
two weeks of high school. If you can capture that feeling. – Those last two weeks in high school, literally, everybody stops
caring what anybody thinks ’cause you’re all going somewhere else. And so, I’ve always had that feeling. It’s crazy how, you know, I was born with confidence,
I truly believe that. I do believe, in my case, I
also have the fortunate aspects of coming from a struggle
place, in a different way. On the flip side, my mom,
I was the first born. The apple of my mom’s eye. And so I had massive
positive reinforcement which then just made me
feel entitled to success. In an environment where
I was failing classes. I was 4 foot 11 when I went into my freshman year of high school. Not so strong…
– Rough, rough. -of a situation.
(laughs) But I walked out– I mean my book bag was bigger. Where’s you big book bag? – Didn’t bring it today,
not on the skateboard, Gary. – Like, I literally– My book bag was like your size. Let me tell you story
about my freshman year. Ninth day of school, I’m
walking down the hallway. I’m late for a class. I have a Jordache book bag (laughs) that’s twice the size of me. I’m walking. It’s like eight minutes
after the bell rang, I’m lost as fuck ’cause we have huge high school,
I have do idea where I am. This is terrible, right. There’s some dude, hanging out of class with Paige Parlow who was one of the hottest
girls in our school. It eight days into
school, I know who she is. She’s a sophomore, he’s a senior. I’m walking by them. He goes, “Psst.” I go, (beep). I go, “Yeah.” He goes, “The nursery
school’s over there.” That’s what happened to me. Do you know what I went through, what went through my mind? I said, wait till (beep)
(beep) (beep) face, punk. (laughs) Sorry, India. That’s what went through my mind. And that’s just where
I’ve always been. (laughs) I know it was a little crude. – Gary Vaynerchuk, folks. (laugh) – All right, let’s move on. (laughs) – [India] From Allen.