“Is it wise to form a startup
around an app or website “which will solve a problem,
but without yet knowing “how to monetize it?” – Yes, Anthony. Solving problems in utility form is one of the greatest ways
to make a shitload of money. You know, for, I mean like, absolutely. Like, like, if you, you know, yes. I’m like, anytime you solve things for, anytime you solve things for people, monetizing becomes the
easiest part of the equation. The reason I’m pausing a
little and jumping around, Vayner Nation, is I’m
rolling with disrespect for Anthony, ’cause. It’s Anthony?
– [India] Mmhmm. Because it’s, it only
speaks to me not believing that you’re gonna solve the problem, to be very honest with you. It, it like, I have a bad
feeling in my stomach. Anthony, I love you, thank
you for supporting the show. I have no interest in dropping venom on Halloween here, but, um. Yes, that’s so like crazy to think about. There’s a million ways to monetize. If you actually bring value to people, even if you make people laugh
and escape their real life, you make tons of money. It’s called the entire
entertainment business. Right? Like, if you solve something tangible, like invent a car so we
don’t have to take horses, ya sell it. Like if you make something, sell something that’s a thing that makes thing better, you monetize by charging
for something that, I’m just. I don’t even wanna answer this question.
– [India] Sorry. This is crazy question. – [India] I’m sorry. – Again, the last part,
even if you don’t know how you’re gonna monetize it yet? – [India] If you don’t know yet know how you’re going to monetize it. – You’re gonna sell it! You’re gonna sell it. You’ve solved a problem, you’re gonna sell it! Either to a human, or
to a business that wants to sponsor the fact that we’ve
solved somebody’s problem, which is the height of value in humanity. – [India] Mmhmm. – Oh look, I created this potion that makes people feel better. How am I ever gonna make money? I mean, what the (bleep). I mean seriously, people. We’ve done this for 158 shows. Like, seriously. Ah! I wanna, I feel like I might,

– What’s the DNA of a good sales pitch? – Yeah. – Um, I think the best DNA
trait of a great sales pitch is predicated on
reverse-engineering what that person actually needs. Way too many people try to sell, it’s really jabbing and right-hooking. Most people want to sell you
what they want to sell you, versus what you need. So, one of the reasons I
think I’ve been successful is, whether I’m selling a bottle of wine or I’m selling myself or
I’m selling VaynerMedia, I have a thing, but I’m
reverse-engineering you, meaning, people used
to come into the store and one of the things I was
proud of is, people would say, Do you have a good red
wine that I could have, and I would always say, Well, what are you going to do with it? And it was stunning to me how
many people were taken aback by that, because every other liquor store, wine shop,
– [Mimi] Why that? – [Gary] would just, give them something they wanted to sell. Oh, I’m giving it to a boss. Well, then I would go
with something that had name brand equity that
made them look good. Or, I’m trying to impress wine friends, I’d give ’em something nerdy. So, in their DNA, the core DNA, is reverse-engineering, and I think the other part
that really matters, Kat, is, I do think passion and energy sells. Like, monotone, not
caring, like not believing. So, I think fundamental,
100% all-in belief and then reverse-engineering
what they need. – That makes sense. – Thank you. – Thanks for being on the show, alright. – Okay, I got two, but I’ll
start with the main one.

“from politicians begging for money. “How would you do better
if you ran for president?” Hashtag ready for Gary. – Yeah, I mean look guys. We’ve addressed this multiple times. If you’re new to this show I
will never run for president because I wasn’t born in this country and if I can’t have the top gig I’m not playing the game. How would I do it better? Easy, it’s the whole thesis of all 148 episodes of this show. It’s all about depth, not width. Like, nobody’s winning the random I’m going to blast you with email give me 20 bucks game buy my stuff game. The blanketing and
hoping and praying versus the depth is the complete
misunderstanding of how to sell. I think oftentimes it makes sense to me that politicians are bad at this because most of my politician friends are terrible business
people and salespeople so it makes sense and usually you know, it’s really, it’s actually stunning what kind of level of disrespect I have for most politicians’ salesmanship. They can sell themselves,
but not other products and I think that that at some level is an intriguing aspect and
fine line in this whole thing and so email marketing
is no different than, you know, the direct
mail that they used to do to try to get dollars
and so, I don’t know, I mean there’s so many
ways to do it better. I mean look. I think one of the best
things a politician can do is literally sit in the room,
sit on our God damn ass, and for 15 hours, take a phone, take a phone, and literally do, and literally do, you know, Twitter reply videos. Literally search your name,
because everyone’s talking, and they either love you or they hate you, because if you’re neutral
you’re in deep crap, and just reply to them and say “No Rick, that is not my policy.” or “Thanks Susie for the support.” It’s the depth over the width game. So the same stuff that
works in selling stuff, selling anything, works in this scenario, and so I think Twitter replies I think would be
disproportionately powerful. I think Facebook is the most important platform for a politician due to the fact that older people tend to vote and that I think that
Facebook is the holy grail of 45 to 70 year old reach right now. Even better than television. So I would put a lot of
content in that world and talk more about my
policies and my thoughts and more importantly show
the human side of me. I don’t know if people
have been paying attention but I believe the last four
to five presidential elections have been completely predicated
on a popularity contest and we’re in the
entertainment of politics era. Not to get political, but if
you just look at all of them. I mean like, whether you
hate Obama or you hate Bush, these are likable people to those sectors. In comparison we’re in like complete and what’s going on now. We are in entertainment mode. And so I would be entertaining
if I had that opportunity because that’s what would work and so that’s what I would do. I mean cold emailing is
doing absolutely nothing. It feels completely cold. It, you know, won’t do it. – [Voiceover] Ian asks,
“Gary, what’s your opinion

“at closing and sales. What’s
your structure for your pitches?” – For my pitches. So, my
structure for my pitches is complete and utter no structure. I don’t really structure
my pitches a whole lot. My team may, in certain
scenarios, have a deck. But there’s, I’m sure, an
inside joke in this company that when we go into that
meeting, I’m gonna completely side-rail and drive over that
deck, which I do consistently. I’m much more interested
in reading the room and deploying what that client
wants at that exact moment, versus what we thought they wanted. In the same way I sold
at baseball card shows, I would just always react.
I really think my pitches are structured for counter-punching. Which means no preparation
from presentation form, but complete and utter presentation
for knowing the content. See what I mean? This is
the thing that most people don’t understand. They
think that you wing it. No, you’re winging the way
you’re gonna present it. You’re not winging what
you actually know about it. So the way I prepare,
is holistically prepare. A.K.A. know my shit. I
know what I’m talking about in the things that I’m selling. And then basically I’m
reverse engineering deploying your needs against that
expertise at that moment, versus what order the deck
needs to be in the presentation. My friends, the deck doesn’t sell it. The presentation doesn’t
sell it. The skills sell it. – [Voiceover] Jeremy asks,
“Gary, why do you feel the need

but we think it’s funny, so. – So one more time, the entire team- – We were trying to unpack
it altogether at our desks, there was so much going
on in the question, we’re not really sure, we want
to see if you understand it, because none of us do. – Of course I understand it,
this is the #AskGaryVee Show, India. Go ahead. – I co-own two karate schools- – I understand that he
co-owns two karate schools. – Just wait. – Okay, go ‘head. – In influential Westchester, New York. I think he means they’re influential- – Yeah, I mean, in just Westchester, he just means Westchester, he was just hyperbolizing Westchester. Lizzie’s from Westchester, big ups. – I handle biz, not instructor. – What? I handle the business side,
I’m not a karate instructor. – How do I- (both laugh) – Stick with me, India. – How do I, how do I tell
members I’m now a realtor? (all laugh) – Amazing! Okay. Wait, what’s the name? – Excel Martial Arts. – Excel Martial Arts, I
assume what you’re saying is you do business development
for two karate studios in Westchester, all your social
media has been around that, and now you’re making a
segue into becoming realtor and selling homes in the market. You’re speaking to the right guy. I told the world for nine years, or, for 15 years, that
I was a wine merchant, and that I was a wine connoisseur, and that I was a wine expert, and then, just by putting out business content, ’cause I had the chops, I told them that I was a business personality. If you know what you’re talking about as a realtor- if- if you, nice photobomb,
I appreciate that. – I gotchu, man. – If you actually know
what you’re talking about from a realtor standpoint, and
you have smart points of view on the neighborhood dynamics, the upsides in which neighborhoods in Westchester are “blowing up,” things of that nature, then I think you have a huge opportunity, and so, the answer is quite simple. The- the final line is,
“How do I know tell them” – “How do I tell members
I’m now a realtor?” – Members? – Yeah. – So I wonder if he’s
trying to sell people that are coming in for karate, to like, buy a home. I, you know, the answer
is, I wouldn’t sell them in the studio, I would just
start putting out content across all social platforms
with your points of view, not just selling a home and saying, “Hey, come to my open house this weekend,” no, say things like, you know, I see a huge opportunity in White Plains, and south of the train station, I see that as a, or in Harrison, they have a great school system, like, those kinda things, provide value, provide value, provide value, guys, we’re a 144 shows in,
if you don’t understand that you need to provide value
versus selling to people, then you, you should stop watching the god damn show. – We did it, we got it.

– Hey, Gary, what’s going
on, Sean Mitchell here. I’ve got a sales question for you. In the last couple of weeks,
I’ve lost two really big deals that I was anticipating closing. On the first call, I felt
like I did a really solid job, at uncovering their
challenges, in matching up our products, solutions
to those challenges, but on the second call, they
ended up not moving forward and it was a huge surprise to me, so– – Huge surprise– – What is your advice to try
and minimize the surprise – [Voicoever] Baba, ba–
– No. Thanks so much. – Great question. Don’t steal my headphones, India. Come off of six month vacation, stealing my headphones. First of all, and I think AJ
is better at this than me, I always think we’re gonna
win the sale, because I’m so good at being a salesman. But one of the great
ways to not be surprised on losing a sale is to
never think you’ve got it. I think that’s actually
a stunningly interesting aspect of it. So I think, not buying
into your own bullshit or hype is important. I also am a big fan of back-channeling. I do think that you
could’ve been e-mailing and contacting the clients. Some clients are turned off by that. Others can really give
you some information, depends on your relationship
with that client. But really the truth is it’s very tough to mitigate this. I mean, that’s the game, right? That’s the high of sales. You go in for the kill, and you don’t know
necessarily if you’ve made it happen or not, and so I think teetering expectations, trying to communicate
back-channel during the time. Sometimes the squeakiest
wheel gets the oil. Sometimes the squeakiest wheel gets taken off and replaced by a wheel. It’s just a way you’ve got to
figure out your own cadence. Your own touch. I’m a big fan of, I always say I like things sold
before I start selling them. So, if you’re going in for pitches a lot of times, I like
having relationships, putting out content, before those things. I think that’s really an important variable in sales, which is fundamentally selling before you’re actually
going in for the sale. I do believe an answer
on the #AskGaryVee Show will lead to a business
opportunity in the future. That’s selling before selling. And so that’s it, I mean you can do what you can do before the fact, but once you’re in the game you can back-channel a little bit, you can teeter your expectations, but you’ve got to let the results play out the way they will. That’s a good show.

“in as few hours as
possible, what would you do?” – If I was starting again
and I had to make $2,000 as quickly as possible, what would I do? Without all the brand equity
I have, obviously right? It’s funny usually I
say go to a garage sale, I’d probably go to Century 21, buy stuff and flip it on Ebay on the arbitrage cause they’re such a discounter or Wine Library and return
the wine to another store that charges more for it. Deep down, the joke is
and I’m making a fun joke, garage saling, Goodwill, I’m a merchant. Buying something for less
than what I can sell it for is what I’m really good at. With no money, with not a lot of money and I have to make 2K, the
quickest arbitrage I know in today’s society, is to go to places, buy it and flip it on Ebay,
the speed is very quickly. That is literally what I
would do, I know my strengths. If I was to have to build up again, you know, imagine I did fail
and made some critical mistakes and lost everything. First I would have to
rectify my family situation, but then I make a lot of money and I’ve had a lot of
success at being right for the last 20 years,
that’s what I live off of. If I was then to be so crazy wrong that I went out of business, I would no longer be able to rely on my advice as my foundation, so I’d have to go back
to the way I built it in the first place which is
truly sales, selling stuff. Deep down I’m a salesman,
you know the truth is, I need to spend more time and I encourage you Vayner Nation to ask me more sales questions because I think I have a lot more to offer publicly around sales. This show has allowed me to talk a lot more about HR,
management, leadership. The one category where I think I’ve disproportionately
under-serviced my community, is a lot more about my sales skills which are really the
disproportional skills that grew Wine Library while
the technology was catching up. The first year of Wine Library went from three to nine million just because I was on the floor. So yeah, I would say that, sales. That’s it, that’s a wrap. Very special episode,
Isaac thank you so much

– Hey, Gary Vaynerchuk, on holiday so I’ve got a question for you. What have you learned from WineDeals, you Instagram account, the best place to buy wine in America? Link me up here. What have you learnt from you
WineDeals Instagram account that small wineries can still use to make a buck on Instagram? Cheers. – Good job, Vineyard Paul. – [Paul] Hey, Gary Vaynerchuk, on holiday so I’ve got a question for you. – Oh, that was on loop? – [Steve] Yeah. – That’s cool. Does it loop? Oh, yeah, yeah, on desktop, I, yeah. Vineyard Paul, great question. I’ve learned what I thought
with creating WineDeals, the greatest place on
Instagram to buy wine, which is people are
disproportionately paying attention to Instagram, plus Instagram has built-in word of mouth functionality. People, by habit, when they
see something on Instagram that they think somebody else is going to be interested in, tag their
friends in the comments. They leave a comment with
that person’s user handle, because everybody’s paying
attention to Instagram, they’re seeing that alert, then they are then checking it out. I have not seen anything work like this since early e-mail, and early Twitter. I’m sorry, this is very early
e-mail, very early Twitter, where anybody who’s on the platform is disproportionately paying
attention to the platform, in a way that creates
aggressive word of mouth infrastructure, so we’re
selling a lot of wine, we haven’t even taken it that serious. Steve, you’re about to get
really, really in there, you know, we’re kind of
in the Summer months, which is fun, but now, here we are, as I start seeing, you know, it’s funny, when I start seeing leaves go orange and, you know, all that stuff,
like, that’s when I know it’s time for money, right, because I came from retail,
and the fourth quarter is what, I mean, literally, this day. I’m gonna literally get goosebumps. This exact day for me, the
day I stopped going to school, was the greatest day of my life, because it was the day that shit was about to get serious at Wine Library, because we’re about to do a lot of sales in these next 16 to 20
weeks, and football, and no school. I mean, just like the best. So, as much as I love running VaynerMedia, and as much as this is gonna
be a much bigger company, and as much as this is awesome, I’m still a merchant at heart, and I, as, I’m fired up to,
you know, here, today, and ready to go, but I can’t lie, a little extra kicker,
because I love selling stuff and, even last night,
with Brandon, I’m like, here we go, like, I’m just so pumped for this Saturday. I had an interesting Instagram cutpost a couple days ago about
this upcoming Saturday in the store, I’ve got
surprise gifts for people, they’re going to see
Brandon, I won’t be there, don’t wanna fool anybody, and so, Vineyard Paul, I think
that people’s attention is on this platform and that you need to be storytelling on it, and
I do think it’s a tremendous, direct response, selling
right hook platform, and WineDeals, as many of you guys know, is straight right hooks. It’s three wine offers
are discount prices, and, buy, the end, like, there’s no thrills, you know, clever, Instagram-like pictures, to the best of our ability, and,
but it’s the wine. So the attention graph is real, people’s word of mouth
infrastructure is real, and we’re picking up a lot of
customers, it’s going well.

digitaljeff asks, “How important
is it to love the product “that your company sells? “Would you hire someone that
had never used your product? “And can being too much in
love with your own product “work against you? – Yes. I would tell you that it’s the
single most important thing. I think the reason that
I’m a great salesman is that I really, fundamentally
believe in everything that I’m selling. The advice here, my books,
wine that I recommend. I’m about to an Instagram
wine offer for the first time in a coupon. Right after we tape this. I really believe in this Rosé. I know, it’s a little side thing. Sorry, Steve. Steve’s my wine boss. And so, hash tag wine boss. Show him and show hashtag wine boss. Love it. So, we cookey here on Friday. Really your fault DRock
for the battery thing. And so, I can’t wait for the edit of this. Share. (monster voice) Remember the oak monster? DRock, the Share Monster. (monster voice) When the share monster comes out, you have to stop what you’re doing and hit the share button on Facebook. All of you online, you
have to do that right now. Sid the intern, have them
say, yes they just did it, and see how many yes’s you got. And if you don’t count
1,900 to match the thing, start yelling and getting crazy in there. You have to sell what you believe in. The reason salesmanship has a bad name is because 98% of
salespeople don’t believe in what they’re actually selling. They’re just going for the commission. The money is what drives them, not the pride and the lifetime value of selling something good. When you sell something you believe in, you get so much more money out of it, because people come back. Guys, it’s all about the
second and third and fourth and fifth and sixth and
seventh and eighth and ninth and tenth and eleventh
and twelfth and thirteenth and fourteenth and fifteenth and sixteenth and seventeenth and
eighteenth and nineteenth and twentieth sale. Not the first one. And what happens is, if you actually really believe
in what you’re selling, it gives you more conviction and belief that you’re gonna get that sale. And I believe in that tremendously. I think that’s why I
think a great salesperson is somebody that truly
believes and are passionate about what she or he sells, is the number one kind
of person in the world. And that’s what I focus on. And so, I think it is the
prerequisite to being successful. The way you think your
children are the most beautiful and the smartest, that’s the blind faith
you have to be having in what you sell.