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  • - On this episode Casey stops by.

  • Again.

  • (hip hop music)

  • You ask questions.

  • And I answer them.

  • This is

  • The #AskGaryVee Show.

  • - You know I think it was like 122 or something.

  • We had the same count on your show

  • and on my show the same day.

  • - Are you serious?

  • - Yeah, it was like the moons aligned for a minute, Gary.

  • (laughs)

  • - Did videos explode?

  • - Yeah, I mean...

  • - Case, tell the Vayner Nation

  • for the one or two people that don't know who you are.

  • This is a first time,

  • second time guest appearance.

  • And we've only had like

  • three guests ever.

  • So clearly, I like you a lot, Case.

  • - Thanks, man. I mean, it's great to be here.

  • Who am I? I make videos.

  • I have a technology company.

  • And I'm a huge admirer of you, Gary.

  • And this wonderful show that you've been putting

  • out there for all of us viewers.

  • - I appreciate it.

  • So, I think we'll just get right into it.

  • I think we had a lot of questions yesterday.

  • Kinda tweeted out that you'd be here

  • and people got excited.

  • You have a new startup.

  • Which we'll give some time, I'd like you

  • to talk about it for a few minutes.

  • - Great.

  • - But India.

  • That's why I went on the left side.

  • - I know. (laughs)

  • - Let's...

  • Get into...

  • The show. (laughs)

  • Not bad, you are getting better.

  • I'm gonna have to find some new ticks

  • to throw you off.

  • India let's get into it.

  • - [Voiceover] Lucy asks,

  • "At the age of 18, what's the best way to approach a company

  • "and ask for work experience?"

  • - Wait-- - Ask for an internship?

  • - You ask for work? Don't you just ask for work?

  • - [India] I guess because a lot people

  • come to companies and it says like

  • you need this many years of experience.

  • - Oh, I see. - [Gary] I see.

  • - [India] But how do you get that experience

  • if nobody wants to hire you because everybody--

  • - When you're 18.

  • - [India] Yeah.

  • - I got an answer to this, I mean

  • I think that we now live in a world--

  • Casey, how many people,

  • how many people hit you up on Twitter, email,

  • other platforms, comments and YouTube,

  • you must have a gadrillion.

  • How many times have you in your career--

  • When would you say that you started really building

  • into a place where people were really pinging you?

  • Is this now a two, three, four year phenomenon for you?

  • - For work?

  • - Yes.

  • Not for work, more like people that are fans of you,

  • clearly at this point.

  • - It's been a long time.

  • - How long, do you think?

  • - I mean, I think since the first video I made went viral

  • over 10 years ago.

  • - Got it. So, it's been pretty consistent since then?

  • - Yeah. - Good,

  • how many times have you randomly done stuff?

  • Yes, met someone, got on a phone.

  • How many times?

  • - Now, if I could count that, Gary.

  • More than I could ever keep track of.

  • - That's your answer.

  • Who was the question? - [India] Lucy.

  • - Lucy that's your answer.

  • I also--

  • The majority of this entire team

  • is based on random shit.

  • Like so, I think you just ask as many times as possible.

  • There are unlimited companies in a world you can get

  • to almost anybody because of Twitter,

  • again, a true social network.

  • More so than comments on content

  • which a lot of other platforms are.

  • Email, at this point, I think has been played out.

  • It's harder to get to people through email.

  • But that will still work too.

  • I think it's stunning that you can get

  • to most people in the world today.

  • I don't think people,

  • as many people are as wired as you and I.

  • I think people have drawn the line to no

  • but there's plenty.

  • We're not the only two nice guys

  • believing in serendipity.

  • There are tens of thousands wildly accomplished

  • CEOs, co-founders, that will absolutely hire you

  • on spec from one request to get experience

  • whether they give you an internship

  • or pay you minimum wage or even give you a salary.

  • It is a wide open field.

  • It's about asking.

  • - Yeah, I mean, I would even complement what,

  • everything Gary just said, I'd complement that, Lucy

  • by saying, you also have an opportunity via these myriad

  • social outlets and the internet as a whole.

  • Not just to reach out and contact people

  • but to actually prove yourself.

  • Like, if you need to show this experience

  • that these people are seeking after,

  • just do it.

  • You don't need someone's permission to do that.

  • If you wanna work in construction, build something.

  • If you wanna work in an automotive factory,

  • work on cars.

  • If you wanna be a filmmaker, make videos.

  • You now have these multitude of options in front of you

  • to show that you're capable.

  • If you wanna be a writer, write something.

  • - You know what happens in that environment?

  • If you actually have it,

  • not everybody has it.

  • But if you actually have it,

  • you start getting into a place very quickly

  • that you realize, oh wait,

  • I don't need to have a job in the first place. (laughs)

  • - That's right,

  • no longer do you need the runway to prove your worth on.

  • You don't need someone else's approval,

  • you just do it yourself.

  • Scary and very hard to do,

  • it's not to be underestimated just how challenging that is

  • but it doesn't mean that the opportunity isn't there

  • and that opportunity wasn't there 10, 15 years ago.

  • But it's uniquely there now.

  • - We're byproducts of that game.

  • - My entire career is product of that game.

  • - I had a liquor store in New Jersey and got

  • 300 dollar camera at Best Buy

  • and decided to make wine videos

  • because I wanted to be like Emeril.

  • - Wine videos. - Wine videos.

  • India, let's move it.

  • Oh, by the way, I didn't get weird there out of nowhere.

  • We are streaming on Facebook live right now.

  • Be interesting to see--

  • It's a whole different dynamic 'cause these shows

  • are consumed so much on Facebook live

  • which launched yesterday.

  • India?

  • - [Voiceover] Benjamin asks,

  • "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.