Podcast with Gary Vaynerchuk - Creating Confidence with Heather Monahan

What this episode is about

Heather Monahan interviews Gary Vaynerchuk to explore the theme of confidence, discussing his remarkable journey and resilience in the face of challenges. The conversation highlights the importance of community and social media in maintaining connections, as well as the perception that Vaynerchuk has not faced significant confidence struggles throughout his career.

Key takeaways

• Area codes and nostalgia: a reminder that our roots can warm the coldest of hearts.
• Gary Vee's confidence is a fortress built on passion, not public opinion—an inspiring blueprint for all.
• Meditation gurus may envy his innate calm; it stems from family love, not mindfulness apps.
• In a world chasing validation, Gary thrives by downplaying others' feedback—proof that confidence can be self-generated.
• Want confidence? Follow Gary's lead: focus on what you love and cultivate gratitude for your unique journey.

Who speaks in this episode?

• Heather Monahan (Host) · 18 min speaking
• Gary Vaynerchuk (Host) · 27 min speaking

What is discussed, and when

1. 0:00 – 5:00: Vayner X, Empathy Wines, New York Times
2. 5:00 – 10:00: Wine Library
3. 10:00 – 15:00: Wine Library
4. 15:00 – 20:00: Empathy Wines, World War II
5. 20:00 – 25:00: Crush It
6. 25:00 – 30:00: Empathy Wines
7. 30:00 – 35:00: Wine Library

Notable quotes from "Podcast with Gary Vaynerchuk - Creating Confidence with Heather Monahan"

• Who might not know I hate the one Trouty sent me so I'm gonna go off what I think he's the chairman of the Vayner X he's co-founder of empathy wines which were so excited about…

  about Vayner X · at 1:24

• Paycheck or because this is what my parents told me to do or you know so how did it end up was it by chance that your dad started the wine library and you ended up just loving…

  about Wine Library · at 7:19

• Positivity I know extreme negativity not only was she disproportionately negative person she lived her adult life until she was my age right now 43 before she moved to America…

  about World War II · at 15:16

• You're preaching I think that one of the manifestations of my work that I'm most proud of is if somebody goes and reads crush it which I wrote in 2008 and came out in 2009…

  about Crush It · at 24:09

• Say anything to a certain group of people and they're gonna think I could pull it off empathy wines may fail we have a lot of headaches that's gonna be shocking to everybody i…

  about Empathy Wines · at 25:28

Who and what is mentioned in this episode?

Books & papers

• Crush It — Book · Referenced work · 1 mention · first at 24:13
  Gary Vee's book that discusses leveraging social media for business success.
• New York Times — Book · Referenced work · 1 mention · first at 1:42
  Mentioned as part of Gary Vee's achievements as a best-selling author.
  Vaynermedia he's an international best known for his speaking his writing best-selling author v New York Times bestselling books he is a social media phenomenon and mentor to…

Companies & orgs

• Vayner X — Company · Business focus · 1 mention · first at 1:29
  Gary Vee is the chairman of Vayner X, highlighting his business ventures and leadership roles.
• Empathy Wines — Company · Business focus · 3 mentions · first at 1:29
  Co-founded by Gary Vee, Empathy Wines represents his venture into the wine industry.
• Wine Library — Company · Referenced business · 3 mentions · first at 7:24
  Gary Vee's family business, which laid the foundation for his entrepreneurial journey.

Places & events

• World War II — Event · Historical context · 1 mention · first at 15:20
  Mentioned as part of Gary Vee's grandmother's life experiences.

Full transcript with timestamps

0:00 oh my god and it's super universal like like it's unbelievable the warmth I feel immediately if I see somebody has the area code of Jersey it's crazy I believe it at the moment oh so real it's so really like so many people hang on subpoena me ask to change your phone numbers I had I got fired a year and a half ago and they took my phone from me I never realized I'd been there 14 years I'd lost my phone number that was yours Vickie right yeah freaking kidding me I lost everybody thank God for social media I was like do you have your phone

0:59 ready we're ready we are recording for you okay thank you so welcome back everyone I'm so excited this is my first show creating confidence with Heather Monahan and as everybody knows I go big or go home so my first guess I'm so excited to introduce you you already know him you know him and love him it's Gary Vee and a brief bio for anyone who might not know I hate the one Trouty sent me so I'm gonna go off what I think he's the chairman of the Vayner X he's co-founder of empathy wines which were so excited about a co-founder of vaynermedia he's an international best known for his speaking his writing best-selling author v New York Times bestselling books he is a social media phenomenon and mentor to millions and overall badass oh I'm so glad to have this time with you today thank you so much yeah all right so I wanted to start today you know this is interesting because I'm looking at the show around how do we

2:02 create confidence for ourselves and others and diving into some of the hard times in life and how he bounced back from them just so you know I reached out to your team and I say guys I your team's amazing by the way and I said guys I need your help help me dig into his past and let's find sometimes he struggled with confidence that must've been hard no you're gonna love this one this has happened to no one Heather we spoke to his family we spoke to all employees there aren't any times this man has struggled with confidence is that true you know I would say outside of the 6th to like tenth grade window around singular ly like am I starting to like girls and do I have the confidence like ask them out is really the only even resemblance of anything I here's what I've done and this is super interesting where you just took me with that question one of things I'm most proud of is I talk about only things I know one

3:07 of the reasons I'm improv one of the reasons I mean look we're doing this podcast you could see I'm like trying to run the company seconds before we said that I'm like trying to be cordial I like felt bad because I fires going on right now but you're like sitting here we had a few minutes before we started this and like [ __ ] let me put this down and somebody I wanted to be nice I'm like I don't to be back right but like I can go on in a second because I will only talk about what I know it's the same answer to what I'm about to tell you I have basically only done things that I love and I'm good at so it's super hard for me to lack confidence when I'm disproportionately passionate and disproportionately capable of the thing that I'm doing at all times plus then I'm also really really good with people and don't over value their opinions and so look everybody has struggled with confidence but like one

4:00 of the reasons in that investigative reporting that it's been tough is I've I've no question I have now come realized I'm a little bit of a unique kind of dude and I think there's strengths and weaknesses in that you know like like I don't I've never experienced skydiving because I'm like I don't like that and I don't want to do that like like you know like it's there's a lot of things that are limited about major but it's also the reason that that was the answer and I think the overarching answered I just touched on it is that one thing I can tell you is you will be hard-pressed to go through life and find many people as deeply insular as I am I am remarkably incapable of getting too high on people's positive feedback or too low on I'm just in this weird deeply weird zone of like it is what it is um I have super good intent I have zero expectation of others I have no entitlement that I deserve

5:05 anything I am just in this very interesting mind zone that I am so grateful for now that I've come to realize it as I've lived and been about and know Addie just grati it was you know it's it's really funny about that and thank you for noticing that I posted a yesterday like like it is remarkable that so much of what everybody aspires to get from meditation from medicine from self health like from all these things that 99.999999% of people are trying to get to this place through these things my mother and my circumstances and my DNA and my father and my sister and I like my circumstances and DNA and so I'm so grateful for this zone I'm in I'm really really confident have you always felt that great yes sir wow that's me let me rephrase I always I didn't know the word was grateful I always was like I was super in love with my mother you know like because I knew something good was going on I was super I never complained

6:26 never like just don't have that gear can you start working with children more please I listen what do you think I'm up to right like so much of what drives me today is the fact that there is an enormous amount of 13 14 15 16 year-olds that think I'm cool cuz of Instagram and I am secretly so grateful for the opportunity to like form some of their opinions absolutely I really am a woman the other day tweeted yesterday like finally somebody pentas Crean shot of a text message with her and her son and she said finally finally finally somebody's penetrated my son and I can't tell you how good it made me feel well to me the overarching theme to me is more than the gratitude is that you're leading this Purpose Driven passion life which so many people do not live in so many people go to work to chase a paycheck or because this is what my parents told me to do or you know so how did it end up was it by chance that your

7:26 dad started the wine library and you ended up just loving wine and sales was there how did those dots connect they started in fourth grade I believe when I decided consciously off of intuition and feelings that I didn't believe in school and that I knew think about how young you are you buddy he never said this is frustrating as a mother because I have an 11 year old and I'm all about you encouraging it you know these kids not to complain however it's dicey when you start saying I wanted to get out of school and schools not for everyone it's dicey if you hold the institution of school being an A on a pedestal and I think that's fine I don't I want none of my opinions to be anyone else's opinion I want to share my opinions that I've lived or I've observed very closely and want to talk about them I get 10,000 DMS a week from children 13 to 20 saying things that they would never tell their parents

8:30 and so when I say things about hey parents youth you're buying your daughter a BMW because she's begging for it but she's telling me behind the scenes that I hate my parents for making my life so easy now that kids talking out of both sides of their mouth but they're a 15 year old and so like what's the decision-making process and that is an unbelievable conversation we have a whole generation of parents [ __ ] on millenials but they're the ones who raised that entitlement you know I think of it as enormous self-esteem building in parallel with radical candor and lack of entitlement and that's what I think my mom did she told me I was the best but when I went over for in a little league game she didn't blame the umpire or my coach she said you weren't good enough it's leadership by example I mean that's always it you know but it's very rare in our society today because parents want to build self-esteem but what they

9:34 actually did was built entitlement and kids got soft and we're collectively soft because we didn't pay the piper and have a recession in 2009 everything is materialistic we all care keep up with the Joneses everybody's valuing everybody's opinions opinions are flying heavier and more black-and-white than ever because of social media and we've gotten into this massive cocoon of everybody's listening to every voice but their own and then when some people tell me well Gary my voice says I suck I'm like that's not your voice you've taken on the voice of someone else sure how do you do that with your kid Lady Gaga said something yesterday on social because she crushed the Met Gala and she said something like I once had a boyfriend who told me I would never be famous that I would never win a Grammy then no but did you see they love that yeah they know and she said and I replied to him by saying one day after were broken up

10:25 you're not gonna be able to go to the deli without hearing my name or seeing my face [ __ ] she put it out into the universe she owned it and it's that's my show that's my kid that's so funny just brought that code up and I just so understand that I was told by the system by my report card by the friends parents by my teachers by everybody that I would be a failure D's and F's you're gonna be a failure in life the only boy I listened to was my own and that was instilled by your mom correct through self-esteem I'll never forget it opening a door for elderly woman when I was eight years old at a McDonald's I can see it now oak tree Road please Edison New Jersey nineteen years 1983 maybe 84 before November opening a door for a woman sunny day McDonald's opening a door for a woman and my mom went off as if I won a Nobel Peace Prize she instilled positive reinforcement around a very good behavior my mom also punished me on

11:29 every report card she punished me consistently through high school no Nintendo no TV no phone no friends no going out all the way through my senior year of high school even though I was proving to her that I was capable sports cards helping my dad's business she held me accountable I was still a student and I was failing at school and thus you should pay the price that accountability mattered a lot of moms are and dads are overacting the other way they decided entrepreneurship is cool their kids getting f's and they're like hey you're gonna be an entrepreneur but what I'm worried about is they're creating entitlement you know and so this tightrope of self-esteem building while being accountable is remarkably difficult and then back to like this six to tenth grade of like I like girls but I'm scared to ask him out because I don't want rejection I also didn't conform to peer pressure ever and that was cuz I just couldn't

12:33 hear anybody else's voice I couldn't hear anybody else's voice but my own well there's no way you would have been able to get to where you are today specifically from the social media standpoint where there are so many haters there's so much negativity and attack online that you developing this authentic confidence has got to be one of the reasons why you could get here you know where it comes from also balancing it with empathy let me give you my perspective on when I read something that says well you're you're a crackhead Gary or you're you're a charlatan or you're lucky or you're your daddy gave it to you and they don't know the story of what I actually did at Wine Library all those things penetrate first level you know nobody wants to hear it but immediately my place doesn't go into armed confident [ __ ] you my place goes to man God thank you God for not letting me live a life where I

13:33 would actually take the time to spend and consume somebody's content I don't even consume anybody's content to begin with let alone consume with the interest to tear that person down you have to be so unhappy inside to want to manifest hearing somebody else down and I I listen I don't like talking about this but it's your first episode and I want to give you something thank you my grandma was remarkably negative you know she has dementia now she's been in essence gone for five to seven years but she's been gone to me for 25 years because she was the singular most negative person I'd ever come across in my life and the reason I checked out from her at 16 17 18 whenever I did was because she spent 100% of her time tearing down other people my father my mother it's your father's mother yes my aunt my sister she tried to do it to me but I was like so in a like you know she gave up on tearing me down I think at

14:41 some level cuz she could sense that I didn't give a [ __ ] you know but nonetheless I I'm disproportionally optimistic and positive but I lived my grandma spent her whole summer with us every summer so how would you create boundaries to protect yourself from someone like that I couldn't hear her but other people can how did your sister do it then she did it oh do you understand him that stinks it sucks and so like what people don't know is everything about me cuz I don't share everything like I just shared with you and the reality is like I've seen it up close and personal I know the extreme positivity I know extreme negativity not only was she disproportionately negative person she lived her adult life until she was my age right now 43 before she moved to America you know and like lived in Soviet Russia she was a widow with a fifteen-year-old like she had tough life she had tough [ __ ] life

15:35 she like was a child in World War 2 like I don't judge her all right but I also understand what it is and I understand why my dad is the way he is because that was his framework mother his environment was the Soviet Union and that mother mine was America and coming of age and my mother some how did your dad and your mom get together cuz they sound something to try and my dad is amazing in a lot of ways but he will look at the world- my dad starts with no I start with yes that's a very different way to see the world are they proud of you know your dad specifically my dad is my dad and I are outrageously close and my dad you know just cuz he starts with no or just because he had a negative mom and because he's negative doesn't mean there's so many I mean my dad is ridiculously loyal outrageously proud but I mean I want to do better top of this question when I wrote my first book some people my family were upset they

16:34 don't like hearing about inside your life that was inside knowledge I think my parents well first of all my mom I literally made her out like my mom loves her fel should worship me from the get she lost her mother at five she her dad went to jail when she was a kid she had a tough life too way tougher than my grandmother well interesting thus says you can imagine it's hard for me to let people have excuses about having a tough shot tough like it's very hard for me to accept people blaming their childhood when my mother lost her mother at five and lost her dad for ten years to jail when she was a teenager and like who raised her name a stepmother Wow who wasn't thrilled about it cuz she was just devastated from losing her new husband to jail and then she came to America was poor and she worked every day of her life went on 0 V my mom and I went on to family big he's like like my mom never

17:34 complained a day in her life her life is [ __ ] compared to 99.99% of people that come to me with complaints it's hard for me to get going to accept your complaints when that's my mom's life and it's right in my face forget my life which had its hardships but like not compared to most or just in the mix you know like my mom's most positive like amazing like I'm a byproduct of her so what do you think that is a choice DNA is big chemicals that were put in her cuz she didn't decide at five years old to be like [ __ ] and I'll face this disaster think chemicals real I think chemicals are real I really look this has been figured out long before us like DNA and environment is real DNA is crapshoot environment gets into an interesting game rights also crapshoot you don't pick your parents but what you decide to listen to and who becomes a very interesting debate to me you know one of the things that I'm very

18:43 proud of is I am the practical positive reinforcement in a lot of people's ears right now and I take that very seriously and it really makes me happy because a lot of people don't have the luxury of having family that is chin exactly you know most people have family that's booing for them misery loves company most people want to tear down everybody else's building to make theirs feel bigger you know it's very rare to have pure practical positivity being pumped into the ecosystem hence why all the attention I have and easy for me not to get high on my supply because as you can tell by this conversation I view that as a cosign to my parents and my circumstance I'm not special my parents are special my circumstances were special I'm just living out the circumstances do you ever get afraid and this is kind of off topic but I'm thinking about you being special you know first of all I think everyone's

19:41 special right so in their own unique way they are however you created this real strong forward facing personal brand first yes I think of garyvee first before vaynermedia right question of course you and everybody else so for empathy wines you and everybody else so you know do you ever get worried from a business perspective am I so big that what if I get knocked off by bus tomorrow what happens to the company no what is it what does happen it folds or they rally and decide to keep it afloat in the honor of their fallen leader you never think of that no because it's a silly thing to think about it's interesting it's an ideology for so it's selfish like I'm dead why would you want to set your people and your teams up for success so the company have already the company set up - ok not the company them [ __ ] the company I care about them do you don't happens to Dustin he writes a blog post and does

20:42 his story of what he remembers about Gary this one time he said this thing to me post it on LinkedIn and 400,000 people asked them to be on their personal brand team this is where I'm unbelievably selfless I don't care about my company I'm a human you like it please shocking I've been in corporate America my entire career into the last year and a half and I will tell you I have never once seen a chairman or a CEO come from business at that perspective and I think it's a me that's unbelievable cuz I actually think it's also practical not just altruistic I died I'm not gonna care I don't know I literally don't know what's happening it's over it's a wrap what I've done is I've built such a progressive forward facing personal brand that the collateral on my employees is remarkable do you know what's going on right now my people are getting offered all sorts like specially for Team Garrity these

21:46 two characters like they just have options and that makes me happy Kenny just left the team they got a great gig in California now I think it's super great here that people are naive about and I think that you know I'm a uniquely kind of interesting character and it's is look I make it look a lot easier than it is and and that will either play out or not for Kenny but like he's now family and I think I think I've done that's what the best part of what I'm doing is I'm just in the middle right I just established to you my what's above me right my parents my circumstance and what's below me is my employees they're feeling all the benefits of it it's so interesting because I'm just seeing right now your brand is just pulling people towards you people wanting to be a part of this year you're constantly recruiting but not from a fake standpoint from just a true organic showing the world who you are

22:39 and it's it's genius yeah and it's and it's very um look this is a very I want it I know a lot of people are listening right now I've never heard of me so this is gonna come across pretty aggressive so I'm hedging so please bear with me I hope you see the purely good part of this not the narcissistic part but my ambitions are remarkably high like I wake up every morning trying to have a statue made of me you know hashtag goals you know like and and here's why it's a worthy of a laugh and why I had to hedge it one could see that and be like oh like what is that I see it as if that is actually your framework the only way you do that is a human that is not an athlete or a politician is you have to be disproportionately one of the great nice humans of all time I'm trying I think I think I was gifted something it be like if you're LeBron you don't wake up in the morning at 13 when you realize oh my god

23:45 I could literally be one of the greatest basketball players of all time you don't kind of then run away from that and say like I'm gonna be a painter sometimes people do Gary that's the thing and that's what's important about this show and about your content is letting people know your job is to chase your passion your job is even though it's scary even though it's hard even though everyone's telling you not to do it even though the money's not there yet go anyways look you're preaching I think that one of the manifestations of my work that I'm most proud of is if somebody goes and reads crush it which I wrote in 2008 and came out in 2009 we're talking about a decade now I mean I not only do I fully believe in what you just said because it was the manifesto I also ended up being right because in 2008 didn't seem possible there was no podcasts there was no Instagram you're preaching sister like

24:36 here's why if you never get anywhere close to my level of notoriety or financial rewards you will be just as happy as me in the process of chasing the practical passion don't worry I'm getting there I believe you and I'm saying that to everybody who's listening you know like I was as happy as I am right now in the basement of my dad's liquor store packing boxes you truly were I'm gonna really [ __ ] with you right now you ready for this ready happier I love the process and I love when nobody knows who I am and when I'm underestimated I love it I love it I have a chip on my shoulder I'm an underdog I like being underestimated the thing that is most difficult in my life right now is that I'm overestimated now that's interesting uh-huh now I've crossed the chasm where I could say anything to a certain group of people and they're gonna think I could pull it off empathy wines may fail we have a lot of headaches that's gonna be

25:36 shocking to everybody i weirdly wanted to happen rowdy does not he doesn't because and he shouldn't because this is his first big at-bat he's disproportionate I'd into it I'm not I don't want the loss I don't want the scarlet letter but boy one of the great ways for people to understand the true me is for me to have a loss in a wine business of all things right I don't know I don't know to tell you I'm not scared of that loss you're so unique that way in that as I mentioned before I had a very successful career in corporate America I became very comfortable it was safe I could see it was linear and you just keep getting promoted and the money's coming in and it's it's very comfy I've had to learn in the last year and a half to take the leap into the unknown there's total darkness and this is good for you and what you're doing right now try to you know starting this new company you have to just keep moving forward and it's

26:33 scary and where you love that scary is what I'm hearing I don't cuz I'm so used to loving the comfort it's really it can be really hard purebred entrepreneurship this is some you really hit me in my heart because you articulated it so well from the other perspective this is why I hate so many people going into entrepreneur my friends I couldn't agree more with you need to go chase your passion all all those things that we just talked about this is what led me to self-awareness please make sure you're hearing both of us very clearly you chasing your passion doesn't mean you can't be a number four your passion your happiest place might be the number four right for a leader that you blindly believe in for the next sixty three years sir I'm not sure d-roc said we're gonna leave now whereas two years ago and two of his teammates who are in the trenches with him more like moon that might be true they both just shook their

27:28 head cuz I think that might play out of me not and tomorrow you could walk in that's fine but where I'm going with that is self-awareness you're right I love the dark I started when I was nine you're in fourth buckin grade of course you're supposed to go through school it's also 1983 84 85 there is no entrepreneurship college is the only way to win in our society right there you want to buy a real dark I've only lived in dark I've only lived in the unknown in a weird way that's um that was an amazing gift that you were given although I went the other way at that time I would have thought your life was held that you had to have it yeah everybody thinks that it sounds so hard what's what's hard is not doing something that is true to you and so I want to really redefine success I really really do I really like this is my new thing which is like okay wait a minute right everybody starts with a North Star

28:27 if I through my sheer will and gifts can start a true movement of conversation that success needs to be happy and calm not rich and famous boy could I really be good when I do finally get hit by a bus like that has to be the ROI like it has to be and like my big thing is like like cars and diamonds and wine and like sneakers and homes and planes and tickets to big events like please don't make that your aspirations fine if you want to like knock yourself out but like please understand that making eighty eight thousand dollars a year loving it will always always beat making to ninety seven hating it absolutely and we don't have that conversation in our culture just yet and when people just heard follow your passion where they get stuck let me give an example if we did this podcast eleven years ago following your passion and the other person on the other line says well my passion is to play video games it was

29:33 nothing for him or her to see that they could make enough money to live in society around playing video games when I say that now everybody knows that you can be an eSports star and not only can you live your passion you can be rich and famous being ninja I'm familiar my 11 year old tells me every day so what happens is that's my concern my concern is that everybody listening right now follow your passion do your thing if that thing is knitting or if that thing is sports gambling which would be highly not acceptable right now by most parents of 11 year olds though the math behind it is very similar to poker and all this other stuff and I do believe that moms and dads all across the world right now have eleven year olds who's number one passion is sports betting and they look down on it because what they look on was the past bookies the Mafia hey Las Vegas that's wrong we're all coming from our

30:27 past and I always look at the future that's my knack so what I see is that the gamble the sports bettor is gonna be put on a pedestal similar to the stock trader or similar to a professor or let me give an example it's already happened if you walked into your parents house in 1987 and said dad I want to be a chef your dad would have been like you're gonna be a cook in a restaurant you loser but what would have happened is you could have gone on to become a famous chef which is what culture was ten years ago it's not as cool today to be a famous chef as it was 10 years ago still pretty cool but it's still pretty cool and it's crazy compared to 1985 where your parents would have thought you cook well what you just taught me and and I think it's really important to highlight this we're all coming at something from our past our past experience what we can stop in that moment and do instead is come at it from

31:22 what our future may be and look to me what it may be and open I listened and if you listen to your kids they're gonna give you insights to the matter future there and lutely and this is a very powerful parenting tip every parent is judging their kids based on yesterday but your kids are living in today which is a better indicator of tomorrow that's really really powerful dropping knowledge Gary trying to give DISA me micro contact for my Instagram you know but but this is yeah is I really like how I articulated that like that makes a lot of sense to me and that has been the Bennett you know when I said to my dad I want to open a dot-com in 1996 my dad had never been on a computer at that point I'm being serious right now I've never physically used a computer at that point so he's you know 43 years old and is never in his life used a computer so for him to judge me deciding to launch a dot-com I ended up being historically

32:23 correct I also luckily had an incredible father who at that point saw what I did in a liquor store from 14 to 21 and saw that I worked hard and it wasn't an idiot and I paid my dues and he gave me my opportunity to do that right a lot of kids go into their family business and expect their parents to let them do something but they didn't put in the seven years that I put in I you know people like always like Gary how did you convince your dad to let you do those radical things by working my face off from 14 to 22 by the time now Mustafa nobody understood that so so you know that's when so anyway man I'm really excited we're talking about this I think I just I think we just helped a lot of parents I really mean that and hearing that you have an 11 year old like he's more right than you are now the key to this whole thing was it's funny that I brought 14 to 22 the key if your son wants to be a professional you know a

33:15 professional sports gambler or a sports card flipper or a sneaker flipper or an eSports star or an instant celebrity is work ethic this is where parents often make the mistake in Reverse when I turned 14 I was a bad student I was already baseball card entrepreneur my mom and dad looked at me and said you now work in the liquor store every day you're not gonna be a not gonna Harvard Big Shot that means you're gonna have to work right you might as well start now so if your kid tells you that they're not gonna follow the school system I don't think and they're not gonna be in the NBA they might not be able to be on three basketball teams you may have to cut them to one cuz you want them to still have a balanced life but they better [ __ ] work parents are not putting kids into the working system early enough so now you have a kid that's getting D's and F's but he's telling your mom don't worry I'm gonna

34:08 be the next Mark Zuckerberg Mark Zuckerberg sold CDs Mark Zuckerberg built apps when he was a kid there's a second part of this conversation that's not being talking about I've never talked about it I'm pumped for putting this on film as well if you're gonna let your kid be an entrepreneur and that's the path I want that kid to actually work so what job do you want these kids to get either a business that actually makes money that they're doing by themselves that's fine get a joint account show me Ricky not ideas [ __ ] ideas execution you got a business this summer you're a DNF student going into ninth grade now we're going to high school we've had a very adult conversation that you're not gonna maybe go to college or you're not a great student okay in between your summer from 8th to 9th grade instead of slacking off and getting ready for high school you either a go work at Walmart so you

34:58 can get dirt under your nails cuz that's the future of your life who no kid wants to do that or you better start flipping on eBay or stock X or show me that your Instagram account around Magic the Gathering or around fashion makes money so I'll give you June but if on 4th of July you can't show me a bank account that has $2,000 in it because you sold ads on your Instagram now you're going to Walmart suffocating that is the key to practical parenting instead of ideological parenting right and that is the framework of my optimism and competence and confidence because what happens is that kid gets real life and so what's gonna happen is Sarah is either gonna sell $480 worth a slime which the market is gonna give her positive reinforcement not her friends saying that she looks pretty the market buying 480. that becomes that's what was my positive reinforcement I didn't need my teachers or my friends or the

36:02 system when I did a baseball card show and I sold 2,000 dollars worth of cards the market was telling me I was good validating you validation the market no individual human want to do it mark it look I'm literally gonna look at these coupons I really interesting insight that is really powerful it's why nobody's opinion ever mattered to me but everybody's collective opinion matters to me reputation matters to me just not Dustin singular point of view and does things matters too because he knows me better than you do and now you matter more to me than you did thirty minutes ago but Ricky pants forty nine whose leaves a comment on insta he just knows what he sees on instant right he doesn't know me your closest friends and relatives don't know you nobody actually ever fully knows you so why are you letting somebody's anonymous comments dictate how you feel about yourself that's so important I get so much feedback from

37:00 people that haters crush their confidence and they really struggle to overcome them they they value other people's opinions you know what else does people like Gary you're so humble I don't value other people's opinions so when people come in and say you walk on water I'm like cool both ways right a lot of people talk about the trolls or the haters you know when you kind of cross the chasm and now you're getting macro radicular like the praise though we like the friend I think people that's where people's vulnerabilities are they like the praise so now they're validating other people's singular opinion but then whoops what just happened you know pretty goes to ugly really fast right and now you're caught because you loved it when it was pretty but now buddy somebody said ugly so really it's it's taking those compliments off the pedestal and things were even all the time we're all equal all the time and whether the

37:51 comments positive or negative I'm not gonna let I would tell you if you said push comes to shove Gary which one do you hear more the I have empathy for the negative feedback because I want to continue to evolve and I don't want to just say it's a hater how many people say somebody's a hater or a troll but that person's actually right no I I never thought about that so I see a lot of people who are selling spam selling [ __ ] products and services and when somebody leaves a comment that says your snake oil salesmen are like hater under saying that these goji berries cure cancer MLM and you're trying to sell people into it they're right you're wrong so I never want to become that character sure of myself I never want to be resistant to feedback so even though I don't value the opinion I I listen it may not penetrate my soul or my behavior but I listen and I always try to calibrate it again sub like do not

38:50 become delusional do not become a caricature of yourself got it it's very easy to get caught up when you have as much positive you know reinforcement as I have right but I try to keep myself very much in a zone I like that idea of you know really instead of thriving off of the compliments thriving off of the positive feedback let it come in accept it listen to it like I said listen to everything that's out there but don't allow it to affect you listen I'm more likely to like really be thoughtful about a troll comment then smell the roses and I think that that level of you know if you're gonna have confidence you need to balance it with humility that's where it gets really going and then you sprinkle a little empathy for the other person again everybody who's listening if you've literally stopped posting cuz somebody said you're ugly or stupid like you have to understand that that person's in a bad place right we have to

39:45 start talking about that like it takes energy to muster up watching something and then leaving a bad comment think about how could you imagine if that was your life now it's very sad like I've never done that in my life once no never but you're right it's all about them it's not about the person that's receiving that version of me that's like that is sports me something that always happened yesterday yesterday the Milwaukee Bucks beat the Celtics you might be a Celtics girl since you're from up there and it goes to three two one the series and I wanted to tweet a Paul Pierce who after Game one when the Celtics once said the series was over and the Bucks were finished I wanted to like tweet and be like now what Nick because I hate Paul Pierce because I'm a Knicks fan the old again back to I mention my grandmother because I have a version of me where I'm sad as a Nixon Jets fan and I want to pull down the

40:42 Patriots and Celtics I'm like oh that's sports that's a different arena but I really feel it that's sports wait a minute that's how people actually live life if if my real life was Jets fan Gary I would be devastated and the fact that that's how everybody actually is acting right now about politics and life and social media so one of the things that you know that's why I understand certain things I'm self aware that I am you know envious of other teams being successful I'm sad that my team is not winning I don't feel in control one of the biggest reasons I tell everybody you're fully in control is because I believe it I believe I'm in fully in control makes my life happy I am not in control of the New York Jets why do you think I want to buy them that misery I want to get into control if I owned them then I am in control and so like you know so I under like that's how people live their lives they feel like the

41:41 government's in control right they feel like their spouses and control their boss their corporation the system yes I don't believe that I believe you can be very that doesn't mean that women don't face more difficult things than men that doesn't mean minorities don't feel like there's systemic issues but like everybody's got problems having too much is a problem sorry I can't I mean I've been talking more not only do I think it can be if you actually hear what I said earlier the BMW story like I spend way more time much time on the entitled rich kids than I do on the poor kids I think the poor kids have it good because they have a chip on her shoulder and with the new Internet nobody's stopping that right I think it's the rich kids they're sorta over spoiled kids that are in deep deep deep deep [ __ ] they're soft what about your kids gonna be soft I'm not joking but kid what can you do then to address

42:35 that I'm gonna do the thing I'm gonna do which is I'm gonna cut them financially off completely oh my gosh completely are you serious I feel like I'm going down an inevitable path of giving away all my wealth to charity I really believe that which is wild cuz ten years ago I would have laughed you out of the room if you told me I'm an immigrant family money I just think the money's a problem that's shocking you know it's shocking for you to even to come out of my own lips but this is what happens when you live something this is why I love talking about things I know instead of judging things I don't I judged Bill Gates and Warren Buffett fifteen years ago when I first heard it but that's because I hadn't lived it yet now I realize oh my god if my kids know that they have a parachute at all turns they can't live a comfortable Wow which then leads to uncomfort exactly for but but I have to watch them because they're

43:28 still young for example it's uncomfortable to me because I would never want anything I achieved to be hedged that it wasn't done by me but that's me not everybody's like that some people love the idea of being third-generation wealthy and just enjoy they I have too much pride and love over the process some don't like it so you've got a you've got to listen so I'm just gonna be thoughtful and woke and open to all these things with my kids and we'll see I have no idea most likely one of the kids is gonna want to climb my mountain and be bigger than me and one kids gonna want to give away all the money in Africa I mean all of that's fine I will not judge my children on how they react to their circumstance and DNA I will not I have no interest in my kids being entrepreneurs I have no interest in my kids being competitive I have no interest in my kids being like me I've interest in one singular thing can they

44:23 have as much peace of mind and happiness as I do that's what it's all about 100% that's a real confidence it sure is so I can't wrap up this show Gary without coming in hot anytime I'm scared of doing something I have to do it so I got to ask you something good so I listen your podcast all the time yes my career was all about coming from nothing and up smashing through the glass ceilings that getting to the sea sweeping and chief revenue officer responsible for hundreds of millions of dollars then getting fired and rebooting and starting my own company I would love to share that message with your audience on your show you want to be on my show yeah it's done you are the man thank you welcome thank you so grateful for you sharing your insights your personal moments with this audience and and for your time and just for everything you do because I as a mother I appreciate it a lot too thank you thank you awesome that was so

45:16 good right Carrie

Questions about this episode

Who speaks in "Podcast with Gary Vaynerchuk - Creating Confidence with Heather Monahan"?

Heather Monahan (Host), Gary Vaynerchuk (Host).

What is "Podcast with Gary Vaynerchuk - Creating Confidence with Heather Monahan" about?

Heather Monahan interviews Gary Vaynerchuk to explore the theme of confidence, discussing his remarkable journey and resilience in the face of challenges. The conversation highlights the importance of community and social media in maintaining connections, as well as the perception that Vaynerchuk has not faced significant confidence struggles throughout his career.

What is mentioned in this Heather Monahan episode?

6 people, works and ideas are mentioned, including Vayner X, Empathy Wines, Wine Library, Crush It, New York Times, World War II. Each one on this page links to its own page with every episode that mentions it.

How long is "Podcast with Gary Vaynerchuk - Creating Confidence with Heather Monahan"?

The episode runs 45 min; the transcript is about 8,163 words in 47 timestamped sections.

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