27:13

– Hi Gary my name is Gbenjo Abimbola from Nigeria, West Africa. It’s 2:16 AM in the morning here and I’m grinding. I hope this gets in. My question is short and simple to you and Simon. When do you know you have the chops as a young person to start talking? When you have […]

– Hi Gary my name is
Gbenjo Abimbola from Nigeria, West Africa. It’s 2:16 AM in the morning here and I’m grinding.
I hope this gets in. My question is short and
simple to you and Simon. When do you know you have the chops as a young
person to start talking? When you have the
results to back it but you’re not an all time great yet. Do you start talking
or do you document? Thank you. – I think you start talking,
the whole thing’s a process. You start talking immediately. It takes a long time to become
an overnight success, right? I think for the both of us and
everybody we know that we admire who’s
achieved anything. They’ve been
at this a long time– – Work!
– talking at it, and by the way, they weren’t great
at the beginning. Go watch–
– Speak for yourself. – Go watch early interviews
of Steve Jobs. Right? Early interviews of
Steve Jobs are fantastic. He’s terrible and he
actually in one of them says, “I need to go throw up,”
because he’s so nervous about talking on camera.
He’s terrible. And the point is he practices and he practices
and he practices. He gets better but
he does it out loud and I think the idea of
hiding until it’s perfect it’s a fool’s game. I think you put
yourself out there, you start, you practice,
you practice out loud, then you get feedback
and you can grow. – You counterpunch,
you adjust. – Yeah, you put it out there. – I would say the one thing
that you may be referring to that I talk about a lot is,
it’s tough to come out the gate at 22 and say this
is the definitive thing, here’s my advice. I think talking to
the world about your– – About what you believe.
– correct, is the game. – Is the game.
– I think what we’re seeing on the internet
right now like I’m a– – 22-year-old guru.
– I’m a business coach and I’m gonna teach you
and the only business I have is you’re gonna pay me 20K
and I’m gonna teach you how to charge other people down
the ladder 20K to give you guys that’s the bad stuff. So, your point of
view on the world,– – Yeah.
– and like what you believe and where you come from,
that’s gold. Your process. That’s why I talk a lot about
documenting instead of creating. It’s just truth.
– Yeah. – But I agree with you. There’s no substitute for doing. The amount of people that
wait for the perfect thing,– – Yeah.
– and then never do anything. – You know the most beautiful
thing when you’re young and you think you have
something to contribute is to admit that you
don’t know everything, admit that you’re learning.
– Yes. – If you say I’m a
22-year-old expert and I can help you do X, Y and Z,
you actually, it’s not true. There’s so much more to learn
and everybody knows that. – Everybody who is the
kind of people that you want. – Yes. – People that are attracted
to that are gonna do very little for you besides some
short term dollars. – Agreed. And if you say look,
I’m in this business, I’m fascinated by it.
I’m growing fast, I’m learning fast, I’m still a student
of this stuff but I have this service to offer, that humility is
unbelievably attractive and people want to be a part of that
’cause they know you’re showing up to learn not, you know. – Simon, I don’t know if
you’re paying attention to this but in reverse what’s
happening is people are renting expensive things, showing a bullshit
lifestyle on Instagram. Going to their, asking their dad
to take $25,000 out in cash from a bank putting it on a bed,
taking a picture then putting it back in, just complete
and utter fraud and it pisses me off. – That’s insane. – Yeah and by the way,
it’s just a non-winning game. – And you only attract
people who want that– – The worst. – and that’s not
even who you are. – The worst. The worst. Anyway, Simon.
– Probably lying, isn’t it? – Question of the day,
every guest gets to ask

7:56

– Hey Gary, congratulations on two years of a successful show, I just love it, I watch it all the time and I get all sorts of great advice from you. My name is Shauna, I’m from HasteandHustle.com and I just wanted to ask you a quick question. My question is when you’re at the […]

– Hey Gary, congratulations on two years of a successful show, I just love it, I watch it all the time and I get all sorts of
great advice from you. My name is Shauna, I’m from HasteandHustle.com and I just wanted to ask
you a quick question. My question is when you’re at the beginning of your business, or I guess at any
time of your business, how do you know how much
risk is too much risk? And when to kinda pull back? Thanks again. – No worries, thank you. Shauna, I got a really
good answer for this. I believe that risk is a
very interesting thing. And I’ve got a pretty
good career with it and I will tell you here’s
what mine looks like. I risk as much as I’m
willing to completely lose. And I push it as far as possible. And that’s always my model. That if all goes to
zero on this move, can I still be
breathing and stay alive? Anything that would
put me out of business, put me out of business! And people do that, they
borrow too much money, they dilute themselves
in the company, that could make them lose
control from the board. Anything that would
put me at risk, I stay away from. So, the punch line
is very simply, I’m willing to lose every penny, other than the first penny that I need to breathe. All of it. You know, we do things
here all the time, Vayner, where I invest
and buy things, buy companies, buy,
AcuHire people. And the number’s
always gotta be, if it goes to dead zero, will I still be alive
to fight another day. But I take it right
to that edge. And really not like,
to the penny, probably to
the million dollars. A hundred million
dollar business, the one… you know, just
some little nest egg. But I think, I’m stunned by people that take risks that
actually puts them out. Floyd Mayweather doesn’t take any risks like that as a boxer. That’s why he’s undefeated. Yeah. – [India] From Sean.
– Sean.

6:06

My name is Steven Gold. There’s so many good producers out there right now getting released on labels, getting uploads on Sheepy and Proximity all these channels. Getting blog coverage, even charting on Hype Machine. What separates the artist that get all this promotion and just get a little bit of royalties here and the […]

My name is Steven Gold. There’s so many good producers
out there right now getting released on labels, getting
uploads on Sheepy and Proximity all these channels. Getting blog coverage, even
charting on Hype Machine. What separates the artist that
get all this promotion and just get a little bit of royalties
here and the artist that actually get to make
a living off of music? – Anyone who isn’t afraid
to experiment and I always appreciate producers when I hear
them who step outside a certain BPM or even genre. I always love risk-taking
mentality and for me those are the people that I’ll
remember for years and years and just to name a few like
Skrillex, we’re big fans of Skrillex, of course. Everything
that Jack Q does is really cool. Panpour Nerds we’re huge
fans of them. And who else? I would say Discord love what they do as far
as experimentation. – I also think that musicians
who are able to create a song in our EDM world is amazing because
you get so used to the build up, then the drop then the break
down and the build, the drop and it just seemed so contrived
after a while but you get people like Calvin Harris who make real
songs that embody so much more than just the build and the drop
and I think that is incredible. – I think my answers going to be
slightly more in the context of how you guys know that I roll
which is I think what separates is the market decides. This whole notion that there’s
so much great music I think there probably is and I think
some of the great music of all time was never heard because the
market decided it wasn’t great. Meaning who gets to
decide what is great? And I always find
that super fascinating. It is an executive who’s got
an ear like is a Clive Davis through the years? Absolutely not. It’s the end market so a lot of
you email me and say I’ve been doing a daily vlog called
“DailyVee” and a lot of music has been given to DRock for us
and we use a lot of it and we’re getting hundreds of emails now
because they are getting a lot of exposure from people that
are watching the YouTube show and it’s helping them so a lot
of people want their music on the show and everybody writes
the same thing which is, “This is great.
My stuff is great. “Everybody tells it’s great.” And the answer is
I think at some level the market gets to decide. Everybody wants to
think they’re great. I always think about the way
American Idol when it first came out those people in that first
show of every season where they really truly not the people just
trying to get on TV later but those first two or three seasons
where you would just genuinely see somebody who literally
thought they were great. Right? Who literally thought they were
great and in that environment judges got to
decide if they moved on. I think what is so fascinating
about today’s music marketplace and the business marketplaces
with the internet being the true middleman whether you Soundcloud
or blogs pick you up or you put out YouTube stuff or Vimeo or
whatever you do I think what separates the people
that make a living or not is the paying customer. That enough people decide you
are great that it allows you to do it for a living. – I actually think the ones that
do it for hobby versus living it’s quite simply 10,000 hours. And you guys started it was very different than
what it was four or five years later and you
guys continue to get better. – Do you think that Malcolm
Gladwell like put in the work, do you really think
that really think that? For example–
– Yes. I do. – Do you think if I put in
10,000 hours of EDM skills that I could be great at EDM. ‘Cause I can tell
you right now I can’t. – Ok. – I genuinely think
that talent has been stripped out of the equation. – As an artist or as a producer? – Both because I can tell
you right now that is just not in me. – Authenticity has
to be part of it. And that’s not authentic to you. – Well, that’s right.
That’s right. But I do think the 10,000 hour
thing is very fascinating and I do think and I talk about hustle
and hard work a lot. I just am surprised that talent is
starting to get scripted out of the equation. To be a musician like you guys
are, you guys are talented and that’s a thing. – I have to interject here.
– Please. – I don’t think that I, first of
all, I don’t think that I’m up to par with certain
artist that I look up to. When you talk about Adele’s
vocals I don’t think I was born a prodigy. – But you don’t need to be the
number one singer in the world to have success. – But I don’t think I
was born with this– – Do you think you have a better
voice than the average hundred people out there? – No, I don’t.
– Oh, yes. – The reason I say that
is because I think there’s this mentality today where
people think artists on this unobtainable pedestal but if
you go back to the beginning of human civilization everyone was
sitting in a circle banging on some drums and
singing all together. It wasn’t a separate
outsider, entitled group. – I think everybody can sing,
I just don’t think everyone wants to pay everybody
to hear them to sing. – Today, I think it’s different. I think it’s vision, it’s your
voice, it’s your songwriting, it’s how you curate
your music videos. It’s everything. – The issue with your romantic
point of view right now is it’s not being executed in reality. There are hundreds of millions
of people that want to do, there’s tens of millions of
Americans that want to do what you are doing right now. And more interestingly and you
guys know this, you’re in the scene it’s much more what’s
happening in entrepreneurship, it’s what’s
happening in athletics. There are plenty of people that
have put in lots and lots of hours especially if they
come from affluence where their parents have allowed them to
be able to go to every fucking lesson 47,000 times. Sometimes talent has to
be part of the equation. – And hunger too though.
– Sure. – Sometimes people
are given everything. – Sure. The work ethic is
a big variable. Alright before we start getting
really testy here let’s go to

13:20

culinary virgin to step up to the plate?” – What’s the best way for a complete culinary virgin– – [India] to step up to the plate? – to step up to the plate? – Well, I mean. – Yeah, I get it. – I mean really first of all get a friend that you really […]

culinary virgin to
step up to the plate?” – What’s the best way for a
complete culinary virgin– – [India] to step
up to the plate? – to step up to the plate? – Well, I mean.
– Yeah, I get it. – I mean really first of all get
a friend that you really love, adore, admire and cook with you. Once you do it by yourself and
you don’t know anything about food it’s hard
for so many things. Arugula better than this
lettuce and it’s a lot. Right? So if you cook with somebody
that you and you’re going to have fun with, same time drink
some wine and stick to it for 30 days on the 17th day I’m
going to call you if you’re not sticking with it.
– Yes. My man. – Marcus can I ask you I’m
going to go side question. A little question from from me. One of the things that I’ve
enjoyed in the food scene obviously living in New York has
been amazing for this is when a new thing pops up.
– Yeah. – And when I mean a new thing,
I actually mean an ingredient for spice or a thing.
– Yeah. – Is there any vegetable or
fruit or spice that’s emerging right now in the scene? I’m fascinated by that. – So first of all, there’s very
little things in the food scene that are new.
– I know that. – Because really–
– Is a new interpretations? – What happened, go back to the
French scenario, when we brought so much your just Europe and
France and eventually Italy– – There was still a
lot of opportunity. – What we look at now as new is
very often from not even Japan anymore, maybe Korea but also
now a little bit from Peru is definitely a strong emerging. – Peru?
– Peru. – And what do they got going on? – You think about extension of
the sushi culture is obviously tiraditos, ceviche
and those stuff. – Yes. – So we hear still don’t know
much about and then the last thing that’s going to
come even more is Africa. So when I brought the oldest
spice plant in the world to America, berbere,
which is an old spice man. Ethiopia looked at me
like that’s not new. We’ve had it forever. Or if you think about argan
oil that comes from Morocco. Argan oil is
mostly used in makeup. It’s all over.
– Yes. Yes. – But cooking-wise it’s a
pretty new oil here in the West to cook with. Southern Mediterranean have been
cooking with it for 2000 years. – What about meats from Africa? Will that, do you
think 20, 30, 50 years? – Well the cuts might change.
– The cuts. – Because meat’s a pretty
traditional but then the cuts that we’re using might change
and also that is old school. Right?
– Well of course. When the chef’s
talking about– – Something’s old
school somewhere always. – Exactly. But we haven’t maybe
focused on that country before. That’s right.
I love that. Alright, India.
– Next one–

9:44

“letting go of my job. “I don’t like it, but I’ve been there for so long. “I have loans, two kids to support, a deep fear of leaving “the security and I’m not sure what it takes to make it as a “solo-preneur. Any tips on how to release the fear and “decide whether to […]

“letting go of my job. “I don’t like it, but I’ve
been there for so long. “I have loans, two kids to
support, a deep fear of leaving “the security and I’m not sure
what it takes to make it as a “solo-preneur. Any tips on how
to release the fear and “decide whether to
take the risk?” – I’ll go first this time. Punt leisure.
Punt leisure. You can work, I’m going to call you out. If you really mean that you
can live on six hours sleep. So you have 18 hours,
18 God damn hours. I want to know what you’re
doing with your 18 hours. Because you can work your 9-to-5
and that’s fine and you can travel for an hour here
and there, respect, nice little solid commute. Oh you want to be a family man? Mazel Tov, you can spend two
hours with your kids, what are you doing with
those of the five hours? You’re watching
House of fucking Cards. You’re playing Madden. You’re relaxing from
the other intense. Gary already spent 11 hours. Well great then don’t
complain or want more. Respect that by getting rest and
this and that you’re giving up opportunity to go
into a new market. You want the
audacity to have a 1% life. Let’s call it what it is. You want to live as well as
the 1 to 2% in the world. It’s not very complicated
the math is very raw. If you want to have one of the
best lifes in the world and you live on your terms then you have
to pay your dues to get there. And you have to be lucky enough
to figure out that you had talent in the thing you actually
want to do because you work 24 hours a day and if you stink
at golf or you’re not a good content producer or your logos
like the shit I would make then you’re going to lose. So that’s what you gotta do. And Fiverr was built for you. Fiverr was built or those
talented individuals while trying to find– – Was Fiverr built
for everybody? – Yes, yes for talented and
skilled individuals that want to find financial and
professional development. So what you have on Fiverr today
yes you have sellers making your six digit a year
that are top sellers. – Real quick I apologize, I
know you want to say it but like they’re all going. Here’s the punchline. What’s the mechanics are
you guys taking 20% of the transaction?
– That’s correct. – Is at the number?
Yeah, listen. The reason I went there is
because he’s the chief revenue officer is all going to sound… How do you cure cancer?
Fiverr. How do you go to the movies?
Fiverr. Let me save us time here. Here’s why I’m curious at the
scale that you guys are now not five or six year
ago, four years ago. Giving up 20% for that attention
no different than eBay or an Amazon I think is very
minor for the exposure. I think there’s a Fiverr and
things like Fiverr but you guys are at scale that’s why you’re
sitting here and social media combo if you can make that
one plus one equal four there’s something very real there.
Let’s go.

7:05

“You’ve joked about being overstaffed, “but what’s the balance between hiring “for capacity and waste?” – Tim, that’s a great question. For all of you that are growing quickly, I think one of the things I take the most pride in is my ability to have a pulse on my organization from a sales top-line […]

“You’ve joked about being overstaffed, “but what’s the balance between hiring “for capacity and waste?” – Tim, that’s a great question. For all of you that are growing quickly, I think one of the things
I take the most pride in is my ability to have a
pulse on my organization from a sales top-line revenue impact, and on the bottom-line cost thing. I think I grow businesses way faster. I do believe that if I end up
operating two more businesses, if I have four businesses
in my career before I die, that I’ve hypergrown, I
have two now in my bag, like, really fast, like,
all-time, like, really, especially non-technology
companies, really fast, I will be known, I mean,
I actually think my legacy as an operator could be speed to victory. I think what I’m really good
at is I have disproportional understanding of the
pulse of what I’m selling, and I’m willing to bet right to the brink, because I don’t need to
take home a lot of money. Like, I’ve always left my own moneys and my own vices on the
table to reinvest back into my business, which
allows me to overstaff, which means I’m them
ready for the new business that comes in, and I
don’t have to go crazy finding the talent, and so, because I’m trying to build culture, sure, you can freelance and
outsource less margin, but you can do better cash
role, make more profit, but I want those people part of my team, and grow with them, let them
learn the religion, grow. So, I think everybody’s
got their own balance, but I think it’s completely
predicated on your stomach for risk, because it comes with risk, you don’t wanna overstaff,
then you lose an account and you have to let people
go, that changes the vibe. I think it comes down to
your salesmanship ability, can you always, in a
pinch, sell some more stuff out of nowhere, and I
think that it comes down to the understanding of where
your business is positioned compared to the landscape, meaning, I always knew that I’m
ahead of the market, and the world’s gonna come to me. A lot of our scopes,
our contracts for 2016, are growing very quickly,
because I knew the world in 2009 would spend more money on
Facebook, Twitter, Tumblr, Pinterest, Instagram,
Snapchat, or whatever was there at the time, you know, the current state of the internet, so I’m riding that wave. It lets me bet a little bit more. It’s a pulse-cadence feel, taste thing that allows me to get away with it, but ultimately, more than anything, it’s the balance of your own selfish wants of your take-home income,
versus how much you wanna reinvest in your business. It’s as simple as that. If you’re running a
business and you’re making a million dollars in revenue, and you have $600,000 in expenses,
you’re taking home $400,000. You could make it $850,000 in expenses, take home $150,000,
and then know that that extra investment will allow
you to make three million the next year. I believe in myself ultimately, any entrepreneur, CEO, or decision maker that’s taking money off the table, I believe is betting less
on themselves along the way and are playing a short-term game. To me, the time I start extracting dollars is when I believe less in
the growth of the company.

4:52

“but don’t come close to achieving what I want, “will I have wasted my time?” – Go Chase. You can ask it again. – One more time. – [Voiceover] Malik asked, “If I pursue what I think “is my passion, but don’t come close to achieving “what I want, “will I have wasted my time?” […]

“but don’t come close to
achieving what I want, “will I have wasted my time?” – Go Chase. You can ask it again. – One more time. – [Voiceover] Malik asked,
“If I pursue what I think “is my passion, but don’t
come close to achieving “what I want, “will I have wasted my time?” – No because there’s really
only one thing in life is doing exactly. – The Jets, sorry go ahead. – Which is doing exactly what
you’re supposed to be doing. That doesn’t come from out here. I’ve lived this exact problem. I did what everybody else wanted me to do for the first chapter of my life. – Who was that? That your parents? – The world. – I agree, the market, the market. – Supposed to be a doctor, a lawyer or in some shit or something else and I literally. – Guys by the way who
are watching were old. Back then doctor lawyer was like. – You’re so smart. – Doctor, lawyer. – Yeah, respect. – When’s the last time an 18 year old now is like you should be a doctor or a lawyer. That’s like. – That profession is
going to run out of people to do the work. – It’s insane. That just took me to such a weird place. You should be a doctor or a lawyer or an accountant. Accountant was in the mix. – That was the list. My parents were amazingly supportive. This didn’t really come from my parents. But just culturally that’s where. – Your friend’s parents were sort a son of a bitch, right. I fucking hate the friends’ parents. – The counselor at school. – I never went to my
guidance counselor, ever. Four years of high school, never went. – They don’t know shit. They’re living in a different era. I don’t want to disrespect those folks. – I disrespect different era. – Different era. That being said I serve somebody else for a long time. Emotionally mentally
even trying to reconcile being an artist and athlete. That was because I was paying attention with the culture wanted for me. But that’s all bullshit. There’s only one thing. – Go ahead. Get them both. – You’re right there. There’s only one thing. You doing what you’re supposed
to be doing in the world. You can pay your dues. I have a lot of respect for working hard, digging ditches, doing stuff to survive. Practicality you call it. But let’s be real, you have to do the things that’s in here. Otherwise you’re just burning time. – I’m going to throw in addition, yes. In addition. – You always say yes and that’s what you’re supposed to do. – Is that the improv thing? – Yes, yes. – No but I will say this. (laughter) Countercultural Mike. Mike is just my fake name for general people. Self-awareness. My big thing more than anything is
do not live on regret. So I definitely am also on team being happy will always trump more money at the end at the end at the end. So I try to play that way. Luckily for me mine collided together. But if you know you. And you know like money like money. Like money. Like you just are obsessed by money. Then maybe you should do the thing that makes you the most money because you wouldn’t sit there one day and say damn I wish I was an artist. Now if you’re the other way. – That’s like this in here and you have to be honest
what you want to be. Do you want to be a needlepoint expert. But you want to make 10 million dollars. – That’s fake. – Those two things don’t go together. So you’ve got to be real. – I mean it’s self-awareness
like a reverse engineer yourself to not have regrets. Having regrets in your
70s, 80s and 90s is literally to me the worst thing that can happen in life for sure. – What’s the asker’s name? – Malik. – Malik, seriously in here. The answers are all in here. – Chase I will say this though and this is something
I’ve spent a lot of time with the show on. – Are we really going to go here? – Yes.
– Ok. – I do believe that you and I got lucky by having self-awareness and emotional intelligence isn’t you know. – It’s the new black. – For sure. By the way. It’s always been the black. It’s just being put front and center. – For sure. I just want to make sure
we’re giving practical advice saying like follow from what’s in here. I have family members who
literally have no fucking idea what’s in here. I know them cold. They have no idea. – That’s actually thing one is
you’ve got to figure it out. And the way they figure out is to live your life, get in adventures and do stuff. – You know what. I’m so on that. Test and learn between 20 and 30 to me is hot. I’m hot on this idea that if you really want to live the best life you can live. The new game plan is from 20 to 30 test a lot of things because the downside the risks you could go risky. You’ve got bigger upside than downside. – Classic Richard Branson. Mitigate the downside. That’s literally why Creative Live exists. So you can take thousands classes from the world’s best people. And you can literally dabble. And it’s not just dabble in community college, you’re taking it from
Pulitzer Prize winner, New York Times bestseller, this guy. Smart, smart people. Get you hands dirty. – We’re going to use for 17 hours Let’s go, India. (inaudible)

2:22

“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 […]

“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.

17:52

“If you could swap out one quality of your won “for one of Casey’s, and vice versa, what would it be?” – Mine’s very easy. I don’t know if you know me well enough to answer this question but mine’s very easy. I’m a wimp when it comes to physical stuff. I don’t ride skateboards. […]

“If you could swap out
one quality of your won “for one of Casey’s, and vice
versa, what would it be?” – Mine’s very easy. I don’t know if you know me well enough to answer this question
but mine’s very easy. I’m a wimp when it
comes to physical stuff. I don’t ride skateboards. I don’t surf or ski. I do very little risk adventure. I look at GoPro’s, I’m like, who gives a rat’s ass? Like that’s not even in
my consideration set. You know, one time jumped
off a 50 foot cliff in Jamaica, I still
can’t believe I did that. (laughs) Because there was a lot of chicks there. Stuff was like peer
pressure, college stuff. I mean, like fuck it,
everybody jumped too. Some like eight year old jumped, like all right (laughs). So, having a little bit
of an adventurous bone would be intriguing to me. I mean look, I’m super happy the way I am but if I have to answer the question, having a little bit of
that free spiritedness I think is really attractive to me. – I’m gonna go really specific here, Gary and that’s your taste in and eye for wine. You know, I am an uneducated kid from a lower middle class house. Yet, I present myself as someone
who’s fairly sophisticated. But when it comes to wine
which all conversations in this world lead to wine, (laughs) I couldn’t tell you
which one came from a box and which one came from Gary’s cellar. And that’s something I really appreciate that you treat like an art form, Gary. – I have a feeling we’re gonna have video maybe in a, I think in
12 to 18 months from now we are gonna have to
drink very high end wine while jumping out of a plane or something. We’re just gonna combine this– – I hope not in that order. – No, no, in that order. We’re gonna be really– We may forget the parachute out. It’ll be big news. We’ll probably get the most
press we’ve ever gotten. – That’s true.
– You know, we’re gone. – Great YouTube video. – We just drank too much wine,
forget to pull the cord. – Lot of clicks, yeah.

6:24

“When looking at potential investments that you might “be on the fence about, “how do you balance risk versus reward?” – I always, always, always dramatically value reward over risk. Hey, this is such a great episode to do this in in the context of everything going on. When I invested in Meerkat, it was […]

“When looking at potential
investments that you might “be on the fence about, “how do you balance risk versus reward?” – I always, always, always dramatically value reward over risk. Hey, this is such a great
episode to do this in in the context of everything going on. When I invested in Meerkat, it was obvious that
Periscope was gonna launch within the week of my investment, and that it was completely backed on Twitter’s infrastructure, and that Meerkat was gonna get shut down. As a matter of fact, Meerkat got shut down on Twitter before I made the investment, but the upside was so great, if they were able to win that game, in the world of, remember,
Facebook’s attempt to slow down Snapchat, right, with Poke? Like, you know, the leader
doesn’t always win, right. Remember Blockbuster was
gonna go after Netflix? You know, with their service? Remember Walmart’s gonna
crush Amazon six years ago? Happens all the time, and so, the reward was much greater than the risk, even though the risk was very obvious. I’m always, always going for the upside. The other thing is, I
bet on the jockey a lot. You know, I bet on the jockey a lot, and so investing in someone is not necessarily always
just about that startup. You know, if they’re a true entrepreneur, and I feel they’re a true entrepreneur, they’ve got two, three, four, five, six, there’s a female-driven
company right now in New York that I just bet on that
I’m so obsessed with. I think she’s gonna win in this one, but, like, there’s no doubt in my mind she’s gonna multiple times, and I think Travis and Uber
was the final nail in my coffin that it’s always about the jockey. if you can bet on the right
jockey, you’re gonna win, and so, reward over risk every time. I’m on the offense in life, you know, I do not value, and I feel a far majority of people watching this
show are on the defense. I really do. I feel like when I quantify
the world that I know, 70, 80% of the people fall into defense. They’re telling you and themselves why not verus why it’s going to work, and I do believe that
blind optimism and naivety and self confidence are
enormously delicious traits that allow you to win
more often than you lose, because it’s truly a net-net
game you can lose 800 times. There’s four to five substantial bets that I made in driving
VaynerMedia this year. Two of them are really
working, three of them are not. We won big. That’s how I look at it. I’m not gonna cry about the three. There’s no crying in business. Or baseball.

1 2