“I want to relocate: do
I just pick up and move, “throw caution to the
wind, or do I wait till “I line something up?” – Bernadette, I think, the truth is I need a little more context
to answer that question. Can I see her picture? Maybe that can give me a little context. Oh, nope, it’s some sort
of interesting icon. Bernadette, I think it comes
down to responsibilities, where you are in your life, age group. You know, I really do think
that if you’re under 30 everything should be in play. You should sleep in the
subways of Singapore, you should live on a rock,
you should not eat for a year but not die, you know, like everything should be in play under 30,
because there is no reason to disproportionately deploy
practicality under 30, because of how long people are gonna live, on how much that’s an
incredible time in your life, and I would, absolutely
if you’re under 30, just pick up and go, especially
if you’re not prima donna. See, one of the great advantages
of being an immigrant, as I think about the book
that I may want to write one day: I Wish Everybody
Was an Immigrant, one of the main chapters
is Lack of Entitlement or No Prima Donna Gear, right? Like, last night my mom and
dad went out to dinner with me we were at an event, and we walked through the rain with no umbrella, and we were just laughing, like we just looked at each
other as everybody else in this kind of New York
City gala was kind of like umbrellas and ubers and we just
kind of looked at each other and were like “Belarus,”
you know, it’s just there’s nothing that’s kind of sacred. Everything’s pretty ghetto, meaning that if you’re able to, Bernadette, sleep in a crappy hotel or at your friend’s couch,
or if you’re just not in need of cozy things,
then of course you should pick up and go, because you could work at MacDonalds and live in
a shit hole and be happy, if that’s what’s pulling at you. If you need certain things
to function as a human like a clean bathroom or coziness, then it becomes harder
for you to pull it off, so I think that the graph is really completely predecated on
what you need to function. For me, I need nothing
to function, literally. It’s so damn scary, and
so everything’s in play, when it comes to that kind of extreme, because I can go to zero. I know what it’s like to
live on a small budget. I don’t need fancy things. I can wear the same four pieces of clothes on rotation for three years, so I just think it comes down to you and your ability to
grind, and the truth is, and I’ve been speaking
to a lot of people over this last year, most people
like to say they can grind, but they don’t, so that’s on you. – [Voiceover] Louis
asks: “How do you handle “price objections when
attempting to close a sale?”

I’m developing a short film about you. – About me? – As a child and your entrepreneurial chops. – Oh, ok. – My question for you is
at what age did you decide that you wanted to buy the New York Jets? – Richard great question. I think the age when I really
decided I wanted by the Jets was somewhere around. I don’t know exactly Richard
to be honest with you so I think it’s somewhere around fourth, fifth, sixth grade. When I realized that I was
more likely to buy them than to play for them, Started seeing other kids growing. Little bit faster than I was growing. Being a little bit faster. Wakeil Shaw. Fifth grade Wakeil Shaw. I think gave me one of my first previews into being owner not player because he was a beast and he ran over me in backyard football. So I think a lot of old school references By the way, made that Oded Weinstock reference with Peter yesterday. A friend of mine from middle school hit me up and he’s like oh my god Oded Weinstock, so that was kind of fun. Wakeil anybody went to Martin Luther King 1982 to 85 Edison, New Jersey Martin
Luther King Elementary School knows the name Wakeil Shaw. If you know Wakeil Shaw, find him and say actually so easy
just search on Facebook. It’s so ridiculous. He moved I think the Baltimore area. Anyway yeah Richard that’s the answer. I think, to make this more of an
interesting answer for everybody who’s watching. Which I’m going to start doing more of. One thing I’m going to start
doing India’s when these answers are the fun question what have you I’m going to
trying to go a little bit broad. If you were lucky enough right now to have a younger sibling, a niece or nephew, a cousin. Or if you’re the parent of a child of that is as early as six,
seven, eight, nine, 10 years old really starts talking about what they want to do for a living. Please, please, please think about how to put them in the
best position to succeed. The kids. The children our future India. – True.
– They’re our future. And so I think. You know. And that. Should I want to be a baseball player and you may not think
their athletic enough and I get that. And then so the question becomes do you send them to baseball camp? Or do you actually look at them and say look you know me and mom are 5’4″. You’re not going to come
a baseball player one day. But can you start showing them other parts of baseball, right? Can they become a future
amazing G.M. or manager things of that nature. I think we need to do
better jobs at really reverse engineering the
child that over indexes in disproportionate passion
not the flavor of the month but has shown two, three, four years of consistent conversation
around a hobby or your subject matter. There’s so much we could
be doing with them. In those years where
they have a lot of time, impressionable moldable, that can be very powerful so
please take it on yourself to be responsible to
sniff out the young me’s of the world who really never wavered and we’re all in didn’t pivot, didn’t change their passions. And try to put them in that position. – That’s good.
– Thank you.

“dear Gary, in episode 122 you
say at 22 to 24 don’t settle. “What is the settling age? “I thought you should never settle?” – That’s so weird that’s so funny. – That’s coming right from
something he told you. – Yes, yes. What’s interesting is
we just talked about it though how I just said from 20 to 30 that’s funny that’s interesting timing. I think first of all I
think every goddamn answer on this show has to be very personal meaning, if you and your boyfriend or girlfriend. Have a baby when you’re both seventeen because that’s what happened in your life practicality enters your world. – Casey I was just at Casey’s. – That’s exactly right. Practicality comes knocking. What’s up man practicality here. You’re a different 17 year old because you have a child coming. – Something you’re going to know you’re going to have to raise a child. – So for every single
person that’s watching. I think practicality or settling, because they’re cousins they don’t have to be the exact same thing but their cousins in them, comes at different times. I do think. Look I know a lot of 40 to 50 year olds that are still living in outer space and dreaming. And I think there’s diminishing returns at some level around that. Especially if it hasn’t happened already. Unless their happy. Unless their happy. – But isn’t practicality
the thing you dip into because you can be living your dream. Pretending live in fantasy land but you’ve got to pay rent. You’ve got to eat. And sometimes that actually dip into real life. Is what motivates your passion. Those two things they. – That’s Casey’s favorite answer, right? – Is it? Casey’s favorite answer, I think he said in the show was do something you hate. to realize how much you
want to do something else. Go wash dishes like he did. – Unbelievably motivating. – What the thing you did the most, in your life, what’s the thing you did the most that you hated? – I went to school for fucking ever. – Yeah. – Forever. – From six to 18 I hated life. – That’s why I love it so much now. I’m not in fucking English class. – Seriously we got to put a
filter on this culturally. This is a real thing. People are going to college
for all the wrong reasons. Do you need a piece a paper that says you have to have
a piece of paper to cut someone open? I want my doctor to be certified. I want my airline pilot to be certified. Anything else? Why, maybe there’s some value there. If you’re exploring. If you’re trying to figure your shit out schools a reasonable thing. The average person graduates
college at $35,200 in debt. That’s the average. So for everybody who
graduates with only 10 grand, there’s someone who graduates with 50. That’s bullshit. – Preaching. I’ve been pumping out some serious content around this issue. So the answer is it
different for everybody. Some people get practical at 16. They don’t have that risk tolerance. – Or you figure it out. There is a practicality
when you figure out what you want to do. Then you got to get to work. Would you call that practical? – Here’s what I truly think. I think shit is really hitting the fan. The Internet, I don’t know if you’ve heard of it obviously all of us have, it’s only 20 years old. I know it’s been around for a long time. I know there’s nerds that say, I know. I mean when Windows 95 came out, normal people started
going on the Internet we are 20 years into this thing. This thing is fundamentally
the biggest culture shift of our time.
– For sure. – They’ve changed everything. We’re just starting and all the rules need to be thought about in a very aggressive way because there’s so many
alternatives to the way that we always thought. The amount of people that go to college Because that’s what their parents want because their parents were
sold on the propaganda of college before that– – It’s literally about
their ego most of the time. – 100 percent. – My son went to this, went to this. – I made a shirt called Shmarvard. That is literally my
number one selling t-shirt. It’s not even close. – I saw it. Is it blue? – Yes, yes. India? – I didn’t know the story that’s good. – [Voiceover] Isham asked,

myself, what was the most
important thing you did in your 30s to change your future? – PK why don’t you take that. He’s about to turn 30. – That’s a great question,
and the answer is, I took a deep breath, stepped back,
and I said to myself, where did I kind of want to be in the next 10 to 20 years then. I actually was working at Gillette. I worked there twice and
this was 72-78 and I took a step back and I said you
know, I wanted to be in a position between the ages
of 32 to 35, where I can make a decision to either stay
corporate America on a fast track and doing all those things etc. or shift gears and go into
a small start up, or smaller business environment and write
a couple of my own patents. A bit of an entrepreneurial
spirit, but I wasn’t in a position where I really had those choices. I wasn’t getting
inundated by smaller start ups or new ventures. I so I said you know what,
and I love Gillette they were doing great, and they were
by me and everything that counted, and I said
you know, I gotta get into the New York area, and I
made a decision to move into New York, with a large company
whom I communicated with and said hey for 3 to 5 years,
I’m gonna beat the bushes and see if I want to stay
or go into small business. So that’s kind of when I
stepped back and I said and the rest is history. – That’s cool. So, Peter was there, because
I married Lizzy when I was 28, turned 29 on our wedding night, and so he saw this, which a
lot of you have heard before, which is right at 30 I kind of
freaked out a little bit and started really putting
the pedal to the metal, started Wine Library TV right
after it, and as much as I worked and as intensely
as I worked in my late 20s, 30 started the process of this
insanity that I’m executing against now. So, I just wanna buy the
Jets, but I didn’t think I was going fast enough, and so I
also took a step back and said where am I gonna be in 10 or
20 years, let me make sure my behavior maps it. So, I think if you’re entering
your 30s, I think it’s really smart to think about your 40s and 50s. – So what Gary does on
intuition and gut, and heart, and passion, I kind of did
over my career, maybe in a little more disciplined,
little more balanced, left brain, right brain way,
and it was a driver of why we decided to write the
book, Think to Win, was to try to bring some very
simple concepts and how tos in the world of strategy
and execution to folks who are working in small,
medium, large, companies, public or private, even in
the not for profit sector, where they can take a step
back and say hey look, here are a few principles,
a few how tos, to get folks aligned, fact based– – Yep. – Not myth based, and get
aligned on key issues, key opportunities, and how do we execute. Yogi Berra, who I was a
big fan of, and yes I do have a signed picture from
Don Larson and Yogi Berra. – Cause all of you were curious. – Curious of that, who said,
“A good batter will always be “a good pitcher, and vice versa.” – He is the best. – I’m a believer in good
strategy always drives good execution, and vice
versa, and that’s kind of what this book is about,
a more disciplined way to kind of those how tos to let some power strategic thinking can work. – Tremendous right hook
Peter, let’s go India. – [Voiceover] Ryan asks, “How
do you deal with drama in “the workplace, and how do
you avoid having more drama?”

“that your staff was really young. “I didn’t see anybody
over 40 surrounding you. Why?” – Well, India is actually 44,
she just looks phenomenal. (laughter) I mean, so there’s that. You know, yeah, my staff is young, you know, I think I get
value out of mentoring, though I’m mentoring a lot of people now that are in their 30s and 40s and 50s. Yeah, my team happens to be young, I’m more than open to hiring anybody, race, credence, you know, like, anything, it just hasn’t happened. The company’s young. I mean, like, you know, look, it’s kinda one of these things like, stereotypes, there’s some truth to it? Look, I mean, this company started doing
social media marketing in 2009, ’10, ’11, like, the 60-year-olds weren’t rolling in. You know? And so I just think a lot of people
overthink these things, meaning, like, you know, for example, a lot of people around
me are always, like, wanting me to stage things, for photos, for
interviews, for on my team, you know, like, all this stuff, like, I’m aware that India’s
the female on my team. Like, I’m aware of stuff. I’m aware of everything. I just also think authenticity rules, and so I’ll be answering your question in the question that’s
the broader question. You know, I’m pumped to
have anybody on my team. Listen, and they will all attest to this, I love standing in front of the company and saying, look, I’m 39,
I’m the old man on the team and I’m better at social
media than all of you. Like, I truly believe that. I don’t pre-judge on age,
sex, where you’re from, well, actually, I do judge a little bit
on where you’re from, meaning if you’re from the
streets I do value you more. I do like a little bit of
the grind and the hustle. It’s an absolute truth. It’s so funny, the true
one place where I think more than the cliche things
of age or sex or race, where I’m a little prejudiced, is I value the streets. I just do. And the streets, AKA just struggling. I just, I’m a fan of it. Anyway yeah, just, it’s been
the serendipity of it. The team has been built from people, a little bit less, actually,
so that’s not true, like, India and Steve were here, and I guess the rest of the team, so four, were hired for us, so yeah, it’s an interesting
thought, like, I’m into it. I’m super into it. Apply.

– Yes. – And how you map that. I heard you say recently
that for your 30th birthday, you freaked out and
started Wine Library TV. – I did. – And I thought that was interesting thing to map back, was that the
start of a hockey stick that you kinda went on? I know you talk about turning 40, and how that’s very exciting. – Couple months away. Exciting. A la, I might just disappear. – I’m excited, yeah. How do you see, sort of
like, milestones like that, like, an age or something like that, and sort of like, career,
and comparing yourself to sort of like, where you should be or… – I don’t know if I’ll
ever have anything like 30 because 30 was a real kind
of interesting moment for me because I really, really felt
for the first time in my life, on my 30th birthday, that I
would not buy the New York Jets, or that my, you know, and I think, look, this is a good time to
talk about it if like, if it’s confusing to
anybody, I’d be very okay if I don’t buy the New York Jets. I want to buy the New York Jets, but more importantly, I want the process of buying the New York
Jets, and what hit me was my behavior wasn’t
acting towards a process of buying the New York Jets. That I was starting to become complacent, which was very weird for me,
and it scared me a little bit. Like, I had made it, right? And by everybody else’s definition, and I allowed, in a
world where I very much, we talked about it in Sid’s question, live in my little world, for some reason, you know, obviously I got married at, the day before my 29th birthday, so Lizzie was new in my life, like,
whatever had happened in those two, or three, or
four years from 26 to 30, it was the most complacent
version of myself. I mean, I am a, dramatically,
more of a hustler today than I was at 26, which is
tough because I have children and a marriage, and
I’m like, damn, I mean, this would have been a
much, I’d much rather have worked it out, which
is why I push that objective so much in people’s 20s,
that’s when you don’t go for the cash, that’s
when you sleep on the floor. Right? Like, with 19 people, and like, this room. Like, Jerome Jarre slept at VaynerMedia. Right, like, he hustled,
and now he makes millions of dollars being Jerome
Jarre, freakin’ slept here. Like, I know what it takes, and I, so, anyway, I don’t know why
I’m going left field, birthdays are interesting. You’ve had some big birthdays recently. Birthdays are interesting for me. I’m definitely freaking
out about my 40th birthday. Like, because what’s happening
in my brain right now is like, 40 to 50 is the
foundational decade of like, you know, like, if I don’t
really crush that decade, and there’s a part of
me that laughs at me, because then I’m like, hm. Then I’m gonna come to 50
and be like, all right, 50 or 60 is, like, this is
where you really go to moguls. Like, I know my, I’m
self aware enough to know that’s how I’m driven. I have this equal push
to like massive ambition and equal understanding
of myself knowing that the goals that, you know, it’s funny, I can’t wait to be a
public figure in my 60s, 70s, and 80s, and talk about,
there’s a weird part of me, and it’s an emerging weird part that says, wow, I can make a bigger
impact on the world if I don’t buy the Jets
because I could talk about, you know, the satisfaction
that I have in that I gave it my all, and I, you
know, there’s serendipity, and there’s other variables,
or that, you know, this, you know, I’m a weird
dude, this tragic event happened, and I adjusted my
priorities for, this incredible thing happened, let’s look
at the bright side, and I, you know, my son was a whiz
kid violinist, and I decided to deploy against that. You know, so, I think that
the way I think about it is for me, birthdays are weird, I, definitely milestone birthdays. 30 and, 40 is ripping me right now, and like, 30 did, and so 50 will, and so, and I don’t know if I’m
forcing that narrative or not, but they’re real, but I think
that they definitely make me think about things and readjust, like, I’m sure that, it’s a
cliche thing that I’m sure happens to everybody, but
I didn’t have them at 18, or 21, or 25, it started at 30 for me. And probably speaks to
what I’m ambitious about. I wasn’t as much worried
about my childhood, or things that of that nature. My career has been the beacon of my life outside of my family, and that’s what, I don’t associate myself
with, you know, like, being a party dude, or
like, getting the most out of my 20s, it was
more career oriented. And so, I think it’s
different for everybody. And I think, you know, it also speaks to, you know, these big birthdays are also a tremendously important time to reflect around family and health. Obviously, I took care of my health, and in spending a
disproportionate amount of time on my family hacking, as happy as I am with the extremism of
weekends and vacation time, I’m starting to bubble
up some other thoughts. And so, I think, you know, I
think it’s fun being a human, like, it’s fun to hang
out with the interns here who are like, starting to
go to that next chapter where like, the game they’ve
played their entire lives of school infrastructure’s gonna go away, and they go into a different game. And that’s interesting to watch, and that’s interesting that my parents are interesting to watch to me. You know, there was
something I read that said, you know, when you save
money your whole life, you don’t know how to spend it. So, I’m watching my
parents struggle to relax and enjoy this next
chapter of their lives. And so, like, I’m very
observant as a business person around psychology, but
also as like, a human, I’m interested in how people roll, and I think the best thing
I can say is, you know, go with what feels right. Attach yourself to a couple
principles that matter the most, and let the cards play out as they will.

“What advice would you give
to a high school student “struggling to decide what to
pursue as a future career?” – I’ve got an answer. Get busy. Do something, do anything. And one of my favorite pieces of advice as to exactly what you should do, is do something you hate. Like, I didn’t find my
passion for entrepreneuralship and filmmaking and everything
that I’ve done in my career. I didn’t find that by doing it. I found that by scrubbing pots in a really terrible seafood restaurant. Because when you spend 50
hours a week scrubbing pots, it’s 50 hours a week you’re obsessing about what you wish you were doing. Sitting around playing video games in your parents’ sweet house is the worst way to find
your mission in life. Do something, staying busy
is a really, really easy path to find something you truly
wanna invest yourself in. – I would also then say to recognize that playing video games in
your parents’ sweet house is probably your outlet
to success in your career. I would say that your
ultimate strengths and wants are the quickest gateway drug to upside once you recognize that there’s
something to be done there. Too many of you, in the world don’t believe that the thing
they like doing the most has financial upside. We’ve drawn a line in the sand, that the thing we like is what we do when we have time to do it like. And the other places to
either make money or get by. So many people are in the other bucket are driven by, I’m gonna go into finance ’cause that’s where the money is. Or I just need enough money and then I’m gonna have
good work-life balance, I’ll be on the softball
team, I’ll play video games. I really believe– I really believe that somebody
who’s watching this right now who obsesses on being on six
soft ball teams right now, literally can make 127,000
dollars a year in ad revenue and live events and a
couple other sponsorships and selling a couple t-shirts by literally becoming
the authority on softball in America. – My son who is a junior in high school is spending a good piece of his summer, including right now, today at a university in
Connecticut studying computer, computer science, specifically
focused on video game design. – Yeah. – Just to back up video playing. – Video game culture in 19– When we were kids. To think it was a mass industry. I mean E-Sport’s gonna
be bigger than baseball in this country in 20 years. E-Sport’s is gonna be a bigger business than major league baseball
in 20, 30 years from now. I’ll go 30, I’m gonna hedge a little bit. In 30 years from now. I mean, that is incredible to me. India. – [Voiceover] Atiyya asks, “If you could swap out
one quality of your won

“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.

“In your mid-twenties, do you
wish you had done more things “or focused more on one thing?” – Great question, Yule. In my mid-twenties, I
focused on one thing. I actually was completely
all in on Wine Library. There was nothing else. I’ve said in the show before
that I wish I went out and hooked up with some more
chicks and had fun some fun. That was one thing I wish
I did because I was so, you wanna talk about being
focused on one thing, as a 20-year-old guy in my twenties, it’s actually uncomfortable
how focused I was on the hustle and building the
infrastructure of my career. You know, I think at some
level when you look back, you’re always, you know, I’m equally, this is where I’m like a paradox. I’m equally completely pumped
’cause look how happy I am and those were great
times and I’m happy now, like I would never change anything. At the same token, you’re
always looking back, and be, like, “Ah,
damn, I could have this, “I could have done that.” Yule, I’m pretty happy with
the way things have played out. I don’t like to play
Monday morning quarterback with my life, but I think it served me well. I learned real foundational
skills of how to run a company. It’s why I’m hyper focused
and why I’m capable now to run a company while
doing a couple more things ’cause I know what it takes,
which is serious focus, but once in a while,
you jump in into a show when you didn’t have to. And so that’s where I’m at with that. Thanks for the question, Yule.

have to do to make it rival
Facebook, Twitter, Instagram? (inaudible) – Steph? – [India] Steph. – Steph, what they’re gonna
have to do is win the 12, 13, 14, 15, 16-year-old imagination. There’s no winning after
it hits a certain point. Social networks over the next foreseeable future, in my opinion, have to win the youth, they need to make Snapchat feel like that person’s older brother’s app, and this new thing is even cooler, and that’s how you win, in my opinion. I think you have to under arbitrage, or build off of a utility, I think people don’t recognize how much of a utility Instagram was. Instagram made everybody
better photographers. Which brought a huge,
huge group of people, and then it started getting social. So my two answers are: under arbitrage the 12,
13, 14, 15, 16-year-old, or build a utility, that
starts as a utility, builds a big base, and then flip it, and create the social
network underneath it. Yea, it was a good answer.