“for someone who finds out
that they’re not cut out “to be an entrepreneur?” – Oh yeah, I get it
Malik ’cause you played, I’m just kidding. Being an entrepreneur
is not some great thing. It’s just as good as being anything. It’s just as good as being
a great, I mean listen as much as it’s amazing for
me that I inspire people to maybe build businesses
that then is a gateway drug to happiness in their
life, I’d be, I’d feel really compelled to be financially secure, have better work, life
balance and be a brain surgeon and save people’s lives on a daily basis. Like there’s a lot of things,
or like some of the things, do you know, you know maybe
not as financially rewarding but if you’re wired to be
a great guidance counselor. Impacting teenagers through
those really difficult, and being a guidance
counselor in a high school for real and if you’re not
mailing it in and full of shit and only wanna be there nine
to three and you’re out, if you really are in it. It just comes down,
you know it’s funny, so that would be cool to
be a guidance counselor which leads me to the point
that made me think of this which is if you’re really passionate. And I don’t use that
word as you guys know. I kinda stay away from that
’cause I think it’s kind of a bullshitty word, but if you’re
truly passionate and really into what you do and you
really give it your all. Like if you really do, whether
you do it for yourself or within an organization
that you believe in or within an organization
that you think will get you to the place you want to be one day. Which is really what I try to build here. Which is one of those two things right? It’s a place you want to be,
around me and that energy and that success and that
machine for the rest of your life or you feel like the
things you learn at Vayner over a two, six, 12, 19
year career lends itself to the things you want
to do in the future. If you’re lucky enough to be
in one of those scenarios, regardless of what you do, if you passionately get up in the morning. If you got up this morning
at six a.m. like I did and were fired up to go, of
course ’cause the Jets won, but fired up to go and your
to go was you’re gonna go in the office and from nine to
four you’re gonna clean teeth and work on cavities ’cause
you’re a badass, motherf- dentist that loves the teeth
game well then you’ve won. My advice is if you figured out
you weren’t an entrepreneur, well then you’re just like
one of those contestants on American Idol. That went there, you gave
an at-bat, good for you, kudos. You stood in front of Simon
and he said you f- stink and you’re like crap and then
you went home and it aired a couple months later and
everybody laughed at you and on Twitter they said you
stunk and you’re like alright maybe I’m you know weird
and maybe I can’t sing. Now what you need to do
is comma, move on and try to figure out what you can
do, what you are good at and more importantly what do you love? And then there’s the other big
semicolon, I don’t even know that’s definitely not the
proper grammar, but like there’s the other parallel thing. Which is you don’t give a
crap that you suck at singing. You can’t breathe and believe
that you can do anything else. You’re just gonna sing. Awesome, go get a job at a karaoke bar. Go, work at a music store
and just sit there all day and sing. There’s absolutely this remarkable balance of what makes you happy, what
makes you the most money. Some people are just blessed,
lucky or grind their way into it or were born with
the talent of like being able to do both. I would tell you that if
I could make enough money to make me happy because I
want it, because I like it. I like the game, it’s the
game of it more so than it but go, I’ve often thought
about fully retiring and just garage saleing. You know? But the problem is I just have
too much other ambition and other things I want to do and
it’s really not predicated on the money but like the
garage, I’m very close, I’m one DNA strand away from being a guy that makes $87,000 a year
garage saleing every day. And that’s cool and I have
so many friends and relatives that are rip crap happy that
tried to be entrepreneurs, failed just like I would fail to be a professional
hockey player or a singer, and have gone on to
massively happy, it’s just about being happy and so my
advice for an entrepreneur would be dust it off, be
like alright that’s not me, even though it’s a hot
thing to be right now, and let me go figure out
what I can do that is. To me the magic is what’s the
thing that you can do the best that you like the most? What’s that cross section? And then that’s a great place to be right? It may not be perfect,
you might not be like Kobe who loves playing, you
can see it in his face, loves playing basketball more
than breathing and happened to be phenomenal at it which
is why you become Kobe. There’s a reason there’s Kobe. There’s a reason there’s Madonna. There’s a reason that there
are these one-named people. Cher, you know, there’s a reason, let’s cut to the chase. Because they happen to have
at the inflection point, the passion and love and
desire and the talent for that thing and found that thing. Which is a whole nother category of things to be successful. I feel like I’ve had
that but I also recognize in so many not that exact thing or the upper-middle class version of it. The eight on a 10 point scale, the 7.2, the 9.1, the 5.4. That’s what you’re lookin’ for you know, that’s what you’re lookin’ for. And then there’s the balance
of risk and practicality. So many people are not
born with the risk gene of an entrepreneur. You’re just not willin’
to take the chance, it’s just too scary. I just don’t know the other way. It was too scary not to get F’s for me. I’ve always fought the system. I can’t conform to what
people think is right. It’s just not how I see the
world, it’s just not what I see. So, I think tripling down on you. If you found out you’re not entrepreneur, you probably weren’t
self-aware to begin with to realize that you weren’t
gonna win in that anyway. You’re probably just following
a narrative of what’s sexy or what’s attractive and you need to take a big boy, big girl
step back in your life and say okay let’s get really real with ourselves. What is the thing I’m best
at that I like the most and then triple down on that. Put yourself in that position. Quit your job or quit the failed startup and go start whittling
wood ’cause you might just be great at it and you can
sell the goddamn little statues in an amazing museum shop in Wyoming. Be happy as goddamn hell. Make a good buck. You’re one Instagram photo
away from somebody saying look how amazing this is. Now you’re the wood
whittlinger for the celebrities and like this is real,
you know but this is real. This is how shit goes down and it’s funny and I know it’s a funny thing. I’m glad I got you India but
what do you think happened with DJ’s? They just loved it so much
and so they made 500 bucks on the side at parties. DJ AM, I watch Doc U, and
then he became the one that did it for Madonna’s parties and then he got paid a million
dollars to be the DJ in residence in Vegas. Funny things happen when you
triple down on your strengths. A lotta times the world comes to you. A lotta times the world comes to you. It may not seem like you
can make, too many people are like I’m awesome
at this and I love this but it doesn’t make a lotta money. I hate that because that is
the place to go ’cause all of a sudden the world comes to you. 1979 I’m a great chef and I
love cooking more than life but I’m not gonna be a chef
because it only pays $50,000 at this restaurant and I’m the help. Yeah until that 22 year old then in 1995 is 37 and celebrity chefs are now a thing and she has her own show. I mean like, that’s what I think. Cool, that was fun,

“your humble self or a
caricature of yourself “in today’s service-based tech industry?” – Chris, the best thing
to do, this is a good time to answer this question. The best way to do anything
is to be the truth. So sometimes I’m humble, and
sometimes I’m egotistical, and sometimes I’m ridiculous. And this would be one of those times. I think your honest self
is always the right answer. If you’re trying to play to
what the market likes right now, you’re gonna always have to change, right? Right now entrepreneurship is cool. By the way, when the tech bubble bursts, when, God forbid, and I haven’t
been able to send my love to a lot of my business
associates that live in the Paris area, obviously
grew up in the wine business, know a lot of people in that town, and so God forbid when that, when, not if, when that happens in the
US and the market pops, entrepreneurship’s not gonna be hot. Practical, paying your
bills is gonna get hot. We’ve had a great 10 year run
here that everybody’s kinda living in right now,
and all you youngsters haven’t really tasted the alternative, you haven’t tasted the stock
market splitting in half, jobs not being available,
you not getting recruited by everybody, your
homies from school saying come start a business with me. Practicality is really
on the horizon, I see it. Oh, there you are practicality! It’s coming, and when it comes it’s going to be an
interesting market change. This show, hopefully I’m
doing it when it happens. Well, hopefully I’m not, hopefully it doesn’t
happen for awhile, but. I think you have to be you,
because I was entrepreneur when it wasn’t sexy, I’m entrepreneur now, and I promise you, and I’ll
play this clip 22 years from now I will be entrepreneur
when it’s not sexy again. (India mumbles)

– [Voiceover] Meet asks, “Hi, Gary, “it seems like everyone speaks about “not giving up no matter what, “but how do you know when
it’s time to let it go?” – So, I’m, this is
something I struggle with, like, having a loss on
your resume is so scary, and the business ventures that I’ve had in the past where I
wasn’t actively running and I’ve talked about Cork’d or Forrst. Lindsay and Kyle, amazing entrepreneurs that I don’t feel that I supported enough and thus those two, Obsessed
TV with Samantha Ettus, where I try to produce a video show, that didn’t start me. I never was able to give it enough energy, and the thing I spent
the most time with is when do I let it go? Because there’s a point where you realize, by the way, I realize this with employees, you know, I know a lot
of VaynerMedia employees watch this, but I’m gonna tell the truth. There’s 5 to 6 employees that I think it might be time to not
work together anymore, and do I struggle with that? Boy, do I struggle with that. One, mainly because I don’t
like letting other people down more than anything. The truth is, Meet, I think
this is a very personal answer. I think it depends on every individual, but what I will say is, way
too many people watching this right now are holding onto
hope, or a non-reality, or don’t wanna make somebody feel bad, or dont wanna have the
reputation of having a loss on their record, and I
think that’s a huge mistake, and it’s probably the mistake
I’m most vulnerable to, and as I think about my next 40 years of executing, and you’re right, I am hustling more than ever, I’m feeling more fit and energized and feel like I’m gonna really
go into my golden years, especially the next 20
years, that’s just the truth, though I’m sure when I’m 60 I’m like, this is when I’m really gonna do it. I do think that that, this
is a tremendous question, I’m so goddamn pumped that this happened on my 40th, post-40th
birthday episode, first one. This is the one thing that
I’m spending a lot of time on. I think it’s hard, but it is, I think more people have
to let go more often. And the two things that I’m working on are both ends of that:
saying no more often, because boy that’s hard for me, and then letting go more
often, and really zoning in on that middle is my answer to that. So the punchline is, very personal, but, because I wanna bring value
to everybody listening, what’s up, podcasters, and watching, I really think that a lot of
you need to take this question, use it as a moment, use it as permission, let me be your olive branch, link to this part of
the show as the excuse or the frame that let you do it, there’s a lot of people
that need to let go. – And if I could have one thing, that would be, this book is probably the
first time where I felt like I was gonna fail in a while. – Interesting, because you, because you had to do the work? It wasn’t like what naturally was in you. – Right, it was, what was naturally in me was just write another book, you know, and I thought that I would
be letting everyone down by doing that, and in three
and a half years in the making, right, there were, I mean,
even up until six weeks before it was done, I thought
it was not gonna happen. – Meaning what? – Just, so many things
were going wrong, you know, in terms of production
and printing processes and finding the right shapes
and everything about it. Also, re-learning how to write sentences. Like, I was beaten. And there was a saying
that a friend of mine, Adele Ressie, had told me that, an entrepreneurship,
it’s always the darkest before the dawn. And I thought that, yo, maybe that is it, maybe this was just a test
to go a little bit further and see it through, but at the same time, it was the right thing to do, but at the same time, there are moments when you have to walk away, and just try to learn from them, because that’s all anybody wants from you is to show that you tried
and that you learned from something and that you did it better or did it differently the next time. – Appreciate it, my friend. As the guest of today’s show,

that I can actually ask
you this question. I’d really like an answer to it. I wanna ask how important is it to create a new lane for yourself? As an artist or entrepreneur, if something is working for you, do you just carry on doing that, even if you have new ideas
that you may wanna explore? I guess the whole point is, how and when is a rebrand necessary? – It’s a great question. Great question, and you
obviously probably know that I went through a
rebrand to a lot of people, which was, I was the wine guy,
I became this business guy, social media guy, whatever
you wanna call me. I did it in parallel. I’m a very big believer
that all of you that have real passion and belief
that you have skill to create another lane, should. And I would call it my
version of an 80-20 rule. I would spend 80% down on
what’s working for you, but I would always have a 20% lane for testing, learning, tasting, creating new revenue opportunities. I do that all the time within my business. Vayner tries a lot of
things, a lot of it fails, but holistically, we win,
because that 80%’s enough. One could argue that we
would do a lot more business if I went 100%, I would agree with that, but then that wouldn’t
open up the capabilities. We’re gonna be the best 360
video agency in the world. That was a bet, an
investment, and so that’s how you have to play it out. 80-20, my friend, it’s a great question for a lot of you. If you can keep 80% of your
practicality and execute, there are, especially if
you play the way I do, which is if you layer on top more hours, then you’re kind of getting 100 over here, and you’re getting that free 20% testing, and you can test one thing at a time in that 20% lane, so you can go 12, 18, 24
months on that 20 on this. That doesn’t work? Try another thing. But I wouldn’t break up that
20% into four, five percents, because you need at
least 20% of your energy to get something going, off the ground, in the way that works for me. Everybody’s different, but that would be my direct,
black-and-white answer to that question.

“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,

“with any of your businesses?” – No, I don’t think
I’ve ever been reckless with my businesses, hence
why they’ve been successful. I think the only reckless
thing I’ve ever done which has caused me
non-successful ventures is trying to bite off
more than I can chew. Sometimes I’m doing way too many things including now, including always. So there’s a level of
recklessness within it, but on an overall collective, it’s not reckless because
it’s a net net score game and I win in business. And so no, I don’t find
myself to be super reckless. I think I’m very much on the offense, but there’s a level of practicality. I’m very P and L driven, profit and loss. That means cash flow, understanding how not to
put myself out of business. I think I leave a lot of
profit on the table each year. I definitely could have a
lot more take home money from Vayner Media, for example,
in the last three years, but I continue to invest in my businesses. Some may think that’s, not reckless, but maybe leaving something on the table? I look at it as long-term investing, not worrying about short-term cash. So no, I don’t think I’m
a reckless businessman. That’s it. No.

from pushing past their comfort zone I’m
not sure what means do I think self-awareness yes you know I think this is a very valid point that
a lot of people in my inner circle like intellectual friends who are watching
what I’m up to a note to self awareness is a pain but my right now argue with me
that is a counterpoint to my point which I have which I have tremendous respect
for but absolutely I’m not scared up and disagree and honestly believe that
that’s the normal which is why the norm sits directly in the middle and doesn’t
have that upside so yes to I think if you’re high percent so hyper self aware
and know that you’re interpreted or you just ate a certain things that you never
explored things can there be some limitations I do but to the point of
true self awareness if you actually know what you’re best at and what you’re good
at and you spend time there you will have the most upside so yeah you could
say well you’re not getting his well-rounded as a person I would argue
that by far the happiest and by far the most successful people are not the most
well-rounded and have gone extremely deep not extraordinarily wide and that
doesn’t mean look i think i play all over the place but I really in one spot
and so it’s about drilling that one spot and so it’s a great questions of
tremendous you know the rock keep you busy lives because we know that many
shows we’re now throw me up a little bit of a tremendous alert tremendous if it’s
a question but one thing that’s really
cool I just like it I just think people should see that car alright I tremendous question one that a
lot of people need to think about but I got my answer is you know I don’t wanna
share my answer is no I’m not concerned about that really not a matter of fact
as I’ve gotten older I’ve become more educated more rounded into more things
because my success has given me permission to do that and I think if you
go deep in the beginning that successful common then you can worry about some of
that second everything’s in my opinion which is rounding out the window when
you missed out on being the greatest singer of all time so that’s what I
think that’s cool statement that I remembered impressive
myself dreamt the couple times I

“When you’re business
is successfully growing, “when do you start another? “And how much time do you devote to it?” – I think it comes down to who you want to be as an operator. Travis Kalanick, CEO of Uber, really taught me a lesson
a couple years ago. When Uber was starting to
take off, he became the CEO. We did angel deals together, and i was pinging him
about this hot angel deal. And he said, “No, I don’t
do angel deals anymore.” And then I pinged him about a talk. And he says, “No, no I’m not gonna talk.” And it was just very focused. And then he’s basically in that Bezos, Steve Jobs, Zucks mold, which is, this is it. This is it. This is the job I’m gonna
do for the rest of my life, and this is my career. I already, clearly, am on my second oofy business. I think I’ve got two
more, three more in me. And so, I’m gonna be an
entrepreneur that has, you know, four or five businesses, is my intuition, India. Clintus. And so, I think it comes
down to who you are, right? And what you want. Like, what’s the size level of a business that gets you to go
into a different place? I mean, VaynerMedia
next year, revenue wise, is going to substantially, probably pass Wine Library’s
biggest year of revenue. So I’ll be going into new territory. Am I an entrepreneur that likes that 50-100 million dollar revenue place, then I go away? Or am gonna see? It really just comes down to a lot of different circumstances. I do think that you need
to question, the question. Which means, if you’re already
asking me this question and thinking about going
on to the next thing, you need to figure out how much you love the
current thing at all. Are you just trying to pass it away? I think there’s a more
interesting insight to that. I think everybody who’s watching the show, needs to think about, are they happy with their business? There’s businesses that you could be making $200,000 a year in, that could be holding you back. ‘Cause it’s a ton of money,
you might just not like it. And so, I think there’s the like factor. For me, I will run this
business, VaynerMedia, as CEO, as long as I love it. That’s really the answer. I mean, I’m glad I got to stick here, because I kind of used a financial proxy as the justification. But to me, as long as I
love it, I mean it could be. But my intuition tells me
I’ve got a couple more. So, I think it comes down to you. And I think it also comes
down to infrastructure. If Brandon Warnke and Justin
Novello and Bobby Shifrin and John Kassimatis and Bryan
Delatorre and Geoff Thurose, if they weren’t in place at Wine Library, along with my dad, I would still be there. VaynerMedia, I mean, some of
you have been here for awhile. VaynerMedia is a helluva
lot better shape today for me not be around, than it was a year ago. I mean, a helluva lot. We’ve gotten dramatically more senior. People have grown. But, I think it’s still
maybe a couple of years away before I feel like it can
sustain and grow without me. And so, the practicality of
this decision matters as well. India, wait a minute, how
did we not talk about this?

that many others have tried
to do before me & failed. Am I stupid to think
that I’ll be the anomaly? – Daniel, that’s a tough question, because the truth is,
there are some mountains that are very difficult to climb and thesis’s that people
love to think are real, and they’re never able to
really fully get there. I think the anonymous social network space is gonna end up being one of them, I think that brings
out the worst in people and ultimately kills
itself from within itself. That’s one preview to a space
that I’m not bullish on, that I think a lot of people are gonna try to climb that mountain, that said, it just takes one tweak, one turn. You know, there was a lot of industries where people couldn’t
figure out how to win, and then eventually somebody
came along and won that game, and so I think that very
similar to the first answer in this episode, it
comes down to your chops, your skills, your patience,
your infrastructure, and really really really does
come down to your skill set. I really do believe that, you know, anybody can do anything
if they’re good enough, if they’re the first of that thing. I just think that people
have to be very realistic to also understand how special
and rare that actually is.

“an old school mind set? “Why not focus on building
wealth via passive income?” – You know, Tommy, I think both work. You know, I think that when people say, “Hey, let’s do passive
income,” they go into Spam City, USA oftentimes. You know, I have passive
income when I’m investing in early stage startups
that then go sell for 400X and I didn’t do anything, I made money, shit, I made more money
on my passive income, probably, than my hustle income. They both work but please
make sure that your passive income has practicality to it because all the people who
have tried to create systems and automate their cash,
there’s been a very small percentage of people that have
been able to lay on the beach while they collect money on the internet. A lot of that stuff is
completely ludicrous and I promise you the ones
in the 1% of passive income spent a boatload of
hard work and hard time to get to that evergreen
place up in the sky. And so, you know, I think that there’s an enormous, massive, misunderstanding that there are (scoffs) almost zero people that
have pulled off substantial success without putting
in real time and effort. Now, we all have different
ambitions and goals. Do I think that it’s easier
to create $60,000 a year in passive income on the internet today? I sure do and if that’s where
your goal and ambition is, that’s more practical than millions. Millions of dollars in passive
income on the internet, smoking (beep) weed in
Jamaica while it just keeps coming in is just not
as real as you think, partner. (laughing) You like that one? I’m right, because that’s
what everybody thinks it is and it’s just not real. (beep) Show me, ’cause I’ll show you a billion people that have won through hard work. Show me. Show me this magical person, ’cause I’ll show you
somebody who sells you that dream but isn’t actually doing it. That, I’ll show you. You want me to hire some
models for the afternoon and get a boat and go to
some sunny (beep) place and be like, this is it? I’ll show you that. You want me to show you
the people on Instagram who go take all the money
they own in the world in $100 forms in the bank
and throw it on a bed and take a picture and then
put it back in their bank? I’ll show you that. I’ll show you the front of
this passive income dream of the internet.