Gary Vee’s Emotional Confession About His Success & Family! | E207

1. 0:00 – 2:01

   Intro

   1. GVGary Vaynerchuk0:00

      There's certain things that I'm not ready to talk about.

   2. SBSteven Bartlett0:03

      Why?

   3. GVGary Vaynerchuk0:04

      I just feel like... (sniffs) She made me happy. Gary Vaynerchuk. Gary V. Gary Vaynerchuk.

   4. SBSteven Bartlett0:17

      One of the world's leading marketing experts.

   5. GVGary Vaynerchuk0:19

      Entrepreneur, investor. A New York Times best-selling author.

   6. SBSteven Bartlett0:22

      And is one of the loudest voices on the internet.

   7. GVGary Vaynerchuk0:25

      I've exhausted the conversation of grinding, learning how to be an entrepreneur in the streets of New Jersey. There was a kid who wrote a Medium piece about me being the face of hustle. I was on a plane, I landed and it was just all this chaos. And there was a lot of things that weren't true. There were some things that really, like, triggered me. I didn't inherit my dad's liquor store. I built my dad's store for him. I knew at 17 that I was a fucking guy.

   8. SBSteven Bartlett0:48

      What's your dark side?

   9. GVGary Vaynerchuk0:49

      The only place I feel like I'm dark is when I'm competing. We did rock-paper-scissors tournament with our leadership team. I quickly thought after I lost in the first five seconds, "Should I fire him?" I was incapable of dealing with losing. What is it that makes me want to be like this? And to be very frank-

   10. SBSteven Bartlett1:08

       You don't have to give me the details.

   11. GVGary Vaynerchuk1:09

       I'll tell you. It's-

   12. SBSteven Bartlett1:12

       Five years ago when we had a conversation, I asked you what your biggest fear was, got these photos here.

   13. GVGary Vaynerchuk1:18

       In Russia.

   14. SBSteven Bartlett1:19

       How does that make you feel?

   15. GVGary Vaynerchuk1:22

       It's very clear to me. It's been there for a long time in my head.

   16. SBSteven Bartlett1:31

       Quick one. At the start of these episodes, I told you that 74% of people who watch this channel frequently haven't yet hit the subscribe button, and I told you that the bigger the channel gets, the better the guests get, and hopefully I've delivered upon that for you. So there's two things I wanted to tell you. The first is, if you've ever enjoyed this channel, could you do me a favor, and my team here a favor? Which is hit that subscribe button because it helps this channel more than you know, and as I say, the bigger the channel, the better the guests. But also, we're approaching one million subscribers and when we hit one million

2. 2:01 – 12:30

   The best insights from your early years

   1. SBSteven Bartlett2:01

      subscribers, we've been working for many months to do something very big in which you're all invited to. I'll reveal that when we hit a million subscribers. Enjoy this episode. With age, my perspective and my recollection of my childhood and my understanding of what was most significant, defining and important has evolved.

   2. GVGary Vaynerchuk2:31

      Mm.

   3. SBSteven Bartlett2:31

      You've just celebrated your 47th birthday.

   4. GVGary Vaynerchuk2:34

      Yes.

   5. SBSteven Bartlett2:35

      More energy than ever, shall I say.

   6. GVGary Vaynerchuk2:36

      (laughs) .

   7. SBSteven Bartlett2:36

      But, um, what have you... As you rel- recollect on your, your childhood from, from that vantage point now, what are the new insights that you've attained about yourself?

   8. GVGary Vaynerchuk2:46

      Probably the most recent one is, like, this incredible need to be a superhero. You know, I, I really took the being the oldest brother to heart. You know, it's funny, my sister and I have a joke that a lot of people don't know that she exists 'cause obviously me and AJ were in business together, and I talk a lot about the Jets, and that has AJ. But my relationship with my sister, who's three and a half years younger than me, may be one of the most profound relationships I have. She (laughs) undoubtedly was the first person besides my mother that kind of cheered for me. You know, she looked up to me. Uh, my mother is incredibly close to her brother, and so she spent a lot of time building that relationship. We're incredibly close. I feel much more kinship to her when I think about my childhood than AJ 'cause I was 11 years older. We didn't have the same childhood. We also moved when he was three. So, all my childhood memories have her in it. And I think as I've gotten... In l- you know, last two, three years, I'm like, "Oh, I have this, like, need to be admired, need..." You know, everything that works for me is when I feel like I'm doing it for someone besides myself. I'm doing it to make my parents proud. I'm doing it to show my sister the right way. I'm doing it for my employees. Even the way I got into better health and fitness was I hired a babysitter, but really what I hired was someone to do it for. Mike and Jordan is who I want to make proud today. My scale being 175 versus 176.8 which it was two days earlier, and Mike texting me, "Great job" on the travel day, I did it for him. And so as I'm getting older, and so much of the Gary V-ness I'm realizing is I'm happy when I'm doing things that make other people happy. Or even at a higher level, creating a framework or a blueprint that they can interpret into themselves. The thing I... You know, as I got older with my sister, a lot of the things I talked about was, "This is my DNA, your DNA is different, but, like, I just... I want you to be happy. We're... It's going to be different for..." You know, those kind of things.

   9. SBSteven Bartlett5:02

      Mm-hmm.

   10. GVGary Vaynerchuk5:02

       And so... You know, you know, when I do things like this, I always go with the first thing that came to my mind.

   11. SBSteven Bartlett5:07

       Mm-hmm.

   12. GVGary Vaynerchuk5:07

       I think what's obvious to me is I've exhausted the conversation of grinding and having to do it for myself and learning how to be an entrepreneur in the streets of New Jersey, and... And recently, in the last couple years, I've talked more about candor. When I wrote 12 And A Half, I'm like, "This is my kryptonite." I'm great at candor in this format. Put me on stage, put me on a podcast, give me 30 people listening to me, I'm Candor King. Managing Dustin one-on-one, I just love him too much (laughs) . Like, like-

   13. SBSteven Bartlett5:36

       Mm-hmm.

   14. GVGary Vaynerchuk5:37

       Even... You know, even this interview, like, I, I went from a company offsite and, like, I got emotional this morning speaking to 30, 35 global leaders, and that was the first time I got... I, I got emotional the way I usually talk about my parents if I'm at a gala or something of that nature. And it hit me and I... My observation was, "Oh, these people are becoming my family." I talk about Brandon Warnke, my best friend, and I tear up. I talk about my parents and my, my siblings and I tear up.This was the first time I kind of teared up for real, for real, deep, deep, deep, deep, deep in a setting when I was talking about those 35 leaders. And it was a nice feeling. I'm like, "Oh, this is becoming family." And so, you know, I think, I think that candor has been a weakness on a one-to-one basis when it's emotional. That I've started talking about. The newest thing of this moment when you asked me is, what is it that makes me want to be like this? And to be very frank, it's quite enjoyable, um, and it makes me happy. And even when I don't deliver, I'm happy at the attempt of. And so I think I'll probably spend the next half decade trying to f- finish this thought and probably produce content around it because I... The thing I always think about is, if I'm this happy, if I lack the anxiety that I see in 99.9% of people, I have a sense of responsibility to over communicate in case a sentence on a podcast triggers something for someone and starts their journey to be happier. I don't know something more noble a human can do than be on a quest to leave collateral, you know, droppings along the way that may help and will help others.

   15. SBSteven Bartlett7:14

       So many directions I want to take that in. I'm gonna go with, um, the first comment you made, and then I'll move on to the second. You said, "I have a desire to be admired."

   16. GVGary Vaynerchuk7:22

       Yes.

   17. SBSteven Bartlett7:22

       Now, when I reflect on that, I completely agree. I think I lied to myself for a couple of years and thought that I was more noble than I was, but what I came to learn, often from doing this podcast, was that some kind of insecurity or some kind of shame was really the driving force at the heart of me. And as I sit here with athletes or Israel Adesanya, the UFC champion, or-

   18. GVGary Vaynerchuk7:40

       Mm-hmm. Love him.

   19. SBSteven Bartlett7:40

       ... whoever it is, uh, you uncover these stories, which at a very young age the thing that might have invalidated them when they were younger is now the thing they're striving to seek validation from as an adult.

   20. GVGary Vaynerchuk7:50

       Well, it's funny. I agree with that, and now I'm gonna tell you why I walk around earth with gratitude and guilt. I... Everything you just said is one of my biggest thesises in life. That is 100% true. Mine is slightly different. I got really fortunate. It's, like, really hard to talk about even without, like, getting weird about it. I'm... My circumstances are l- you know, I think, yes, in some ways. For example, the system. School took such a shit on me in the '80s and '90s. I've... And you know this. We've run in similar circles. I'm very good at fighting the systems of industries. Like, it's also why I see things like Netflix, you're gonna win. Tesla, you're gonna win, because I know they're fighting the thing.

   21. SBSteven Bartlett8:41

       Mm-hmm.

   22. GVGary Vaynerchuk8:42

       And so I recognize it. I've been a good investor, I've been a good operator, and I'm definitely a communicator. College, right? T- f- I was at a talk yesterday. I'm not speaking that much, but I, like... My dad taught me, you know, keep your word, so I had a talk from pre-COVID that got canceled, and then canceled, and then I got COVI- like, and so I, I still did it. And so I did it, uh, yesterday. And a couple of moms came up to me, and both of them, the way they talked to me about the content I'm putting around college was through love and admiration. Twelve years ago, those same exact moms were really angry at me, you know? And so when you see things, you know, you, you, you kind of challenge it. And so yes, I think I... Absolutely, the thing that was an insecurity, I get bad grades, but what was different for me is I didn't believe them. This is, this is where self-esteem is an obsession of mine. Not delusion, right? Not delusion, 'cause that's what a lot of modern parenting does. "You can do anything, Sally." No, you can't. "Sally, you are not athletic enough to be in the WNBA." It wasn't that. It was this weird balance that my mom created between deep confidence, but accountability and truth. I remember trying to make an excuse for striking out in a baseball game and trying to use the sun and my eyes as an excuse, and my mom not letting me do it very subtly. Talk about childhood forming you. Like, this is why I implore everyone to communicate their truth to their children, to the world, through podcast, through content. Like, it's amazing to me sentences change people's lives, right? She didn't let me do it, and I became very accountable because of those levels of parenting and realities, and that accountability led to so much happiness. But for me, when the school system was saying, "You're shit," I didn't believe them. And so I watch a lot of people being driven by hurt, and I can sense that I'm driven by love. I just sense it. Like, for me, it's just, like, deep self-awareness that understands how fortunate I've been. Like, so many things went my way. The mom of the century, being able to leave the Soviet Union in this little window in the seventy... 1917, 19... In the 72 years that the Soviet Union dictated people's live- And to remind everybody, the S- this is something most Americans and Westerners don't understand. The Soviet Union was like North Korea. It wasn't like Iran. Iranians right now are able to leave Iran and go to Tur- you know, wherever their passport is taken. They can't go everywhere, but Turkey takes their passport. Dubai takes their passport. The Soviet Union that my family grew up in was North Korea. You were not allowed to leave. But this little event in 1970 of eight Russians trying to hijack a plane to go to Sweden to escape created a global story that led to pressure on Russia, where Spain and Israel and America teamed up and had this little moment where Russia had spent too much money on their weapons of war and were starting to run out of resources, and conformed to their anti-Semitism and decided to take money from the US and Israel in exchange for a couple of hundred thousand people, and I'm one of those people. And I, born with insane levels of entrepreneurship and gift of gab and offense, get to go from the worst place on earth at the time an- for someone like me in 1978, to the best place on earth. Fuck.... and then getting all love, but not delusion. And so by 10, being in the grit of, like, studio apartment with tons of family members in Queens. Like, all shit, but being 10 years old and having little, but being happy as fuck and being loved insane. And now a 10-year-old me realizes that money has no impact on happiness,

3. 12:30 – 19:03

   How do we build confidence

   1. GVGary Vaynerchuk12:30

      I was built to win. I was built to win. And so I agree with you, I see it in so many of my friends. I always say, "The two ways to build something insane is deep, deep insecurity turned into fuel, or deep, deep, deep levels of confidence turned into fuel."

   2. SBSteven Bartlett12:49

      On that point of confidence, you said your mother gave you your confidence.

   3. GVGary Vaynerchuk12:52

      Yes.

   4. SBSteven Bartlett12:53

      Earlier on you said you get, she gave you your sense of sort of self-responsibility.

   5. GVGary Vaynerchuk12:56

      Yes.

   6. SBSteven Bartlett12:57

      But I've also heard you say that she's responsible for your confidence.

   7. GVGary Vaynerchuk12:59

      And then another thing, the market. So yes, my mother, and so a lot of people listening right now and they had positive reinforcement. There's two things to watch out for, for everybody who's listening, parents or youngsters, or just try to get in, everyone listening. And I, by the way, this is a good time to say this, I consume a lot of content. Meaning I consume no content, I consume how people are consuming content. I just wanna give you some roses, and really the listener on the other side. I've really enjoyed, and this is very lightweight, this is a hot take, it's not like I've done ho- major homework on this, but I feel like you have a very thoughtful audience.

   8. SBSteven Bartlett13:35

      Mm-hmm.

   9. GVGary Vaynerchuk13:35

      I really like what's going on with you and your audience. It's, and it's really both of you, right? It's not just you, it's who self-selects to listen to your guests, and you're doing a great job casting it and all that, but there's something nice going on here. So keep going, and everyone who's listening, kudos on you for understanding there's value here in a world of unlimited content. Here's the two, back to, like, kind of the respect I have, I should, I told, I told you Dustin, I said, "Hey, pay attention today. I'm gonna be a little bit sharper." It's out of my admiration. Here are the two things I want to go extra level to watch out for. In confidence building, too many people go too far and they go into that eighth place trophy delusional place, and then kids don't believe you. I'm gonna be very transparent, I've already sensed that with one of my children where they're calling my bluff on it. I'm like, "Fuck, it's true." Like, you're, I played AJ much harder in every sport than I'm playing Xander. That's the facts, and so I'm already adjusting my damn self.

   10. SBSteven Bartlett14:31

       Xander's your child?

   11. GVGary Vaynerchuk14:32

       Yes.

   12. SBSteven Bartlett14:32

       Good point.

   13. GVGary Vaynerchuk14:33

       So, so one, it's don't let it be delusional. The whole, you can be anything, you can do anything you want, you can be anything you want, you just might not be the best at it or great at it. You can be a musician, it doesn't mean that you're gonna be a financially successful enough musician to pay for your household, or if you want to be, you can. You're just gonna have to live humbly and live your passion, which I think is going to be the conversation in 100 years. I believe the evolution of you and I and a lot of people listening is a lot more people making $61,000 a year doing exactly what has them on fire and living, and living, this is a big part, and living within the means of that 61,000. But that's a different conversation for a different day. So number one, watch out for delusion. Number two, you can't be the only source of positive reinforcement. Had I never gone outside and my mother did everything she did, I don't think I am who I am. The other part that made me was ringing doorbells and having 81 people say, "No kid, I don't want you to wash my car," and having six of them say, "Yes kid, I do want you to wash my car for five dollars." I think what also made me was standing on a lemonade stand for months in my life, you know, two days here, three days here, five days here, months of my life from six to 13, and watching 99.9% of the cars drive by my stand and not react to my great signs and not stop and buy my lemonade. I think what made me was 100 out of a 105 people said no to shoveling snow. What made me was I had a baseball card table and I watched 100 people walk by and not want to buy anything from me even though I had good stickers and good cards. And one, the market made me. All those nos became enjoyable.

   14. SBSteven Bartlett16:29

       It's the yes that acts as the evidence though. So it's the, it's the person coming along in the one in a 100 buying the lemonade that makes a young Gary or young me go, "Do you know what? I can sell lemonade."

   15. GVGary Vaynerchuk16:39

       100%.

   16. SBSteven Bartlett16:39

       And I was, I've thought a lot of, over the years, because, y- the more I speak on stage or the more I, m- my brand has grown, I get the same question over and over again, which seems to be at the very base level of everything I do, which is, how does one build confidence? You've talked about your mum's sort of subjective evidence that you are great, and then you've talked about the, the evidence from the one in 100 buying lemonade. I came to this hypothesis that, um, our self-belief, like all our beliefs, is just, um, based on false or correct subjective evidence we have about ourselves. So if that is true, if it, if beliefs, all beliefs are just evidence, um, what's your view on how someone can build that self-confidence? They're listening to this now. How do they go get that evidence, and do you agree with that thesis?

   17. GVGary Vaynerchuk17:21

       Yeah. I l- I like a lot of that thesis. I also think one of the things to point out that might help a lot of people is my mom also created positive reinforcement for me on the right things. When I think back to what she positively reinforced, it was not when I'd get the occasional B in history as a D and F student, which would be logical. This is the first time I've ever saying this publicly, it's the first time I've had a clear thought on it. It would be logical for a mother who (laughs) really, she, she knew how smart I was, she was borderline pissed. She's like, "Can't you get Cs to appease me? You're so capable." I'm like, "Ds and Fs." Why she didn't positively reinforce the Bs I got in history, which was the one class I paid attention to, uh, is actually a very interesting insight. She didn't reaffirm a subd- a subjective machine that wasn't built for me. What she reaffirmed and built confidence in me was how nice I was to everyone-When I think of my 47-year-old self, I am the byproduct of two energies. I'm a successful entrepreneur, which is what the world taught me, and, uh, for the people that know, they know... Like, especially the people that really know, they know how nice I am. Like, you know this. You've been on-

   18. SBSteven Bartlett18:30

       Yeah, yeah, yeah. Yeah, yeah.

   19. GVGary Vaynerchuk18:31

       You know a lot more about me in subtle little...

   20. SBSteven Bartlett18:33

       Yeah.

   21. GVGary Vaynerchuk18:33

       Like, y- What I love about you is you're smart, so I know I can say this. You know.

   22. SBSteven Bartlett18:37

       Yeah, I know. Yeah, yeah.

   23. GVGary Vaynerchuk18:38

       Right?

   24. SBSteven Bartlett18:38

       And we've had lots of dealings over the space of five years.

   25. GVGary Vaynerchuk18:40

       You just know. Right?

   26. SBSteven Bartlett18:41

       Yeah, yeah. Yeah, yeah.

   27. GVGary Vaynerchuk18:41

       In every subtle way.

   28. SBSteven Bartlett18:42

       Yeah, yeah, yeah.

   29. GVGary Vaynerchuk18:43

       In every subtle way. We've theoretically competed, there's been moments where I could or couldn't come... Like, what I love about this is, you know.

   30. SBSteven Bartlett18:52

       Hmm.
4. 19:03 – 32:26

   Public criticism

   1. GVGary Vaynerchuk19:03

      there are people who today don't think I'm a great dude, and it's off of one clip that somebody wanted to use me to do a split screen to build themselves up because they're in the business of tearing people down to build their building, and that doesn't bother me. Actually, it's one of... Like, I actually have incredible compassion for that person.

   2. SBSteven Bartlett19:21

      Has it ever hurt?

   3. GVGary Vaynerchuk19:23

      Not... I mean-

   4. SBSteven Bartlett19:23

      S- So I'm gonna tell you something.

   5. GVGary Vaynerchuk19:24

      Yeah, please.

   6. SBSteven Bartlett19:24

      So when I became a Dragon on BBC's Dragon's Den-

   7. GVGary Vaynerchuk19:27

      Yeah. Yeah.

   8. SBSteven Bartlett19:28

      ... I, I was exposed to a new level of public criticism-

   9. GVGary Vaynerchuk19:31

      Mm. Mm-hmm. Mm-hmm.

   10. SBSteven Bartlett19:31

       ... and misunderstandings-

   11. GVGary Vaynerchuk19:32

       Mm-hmm. Mm-hmm.

   12. SBSteven Bartlett19:32

       ... of often intentional misunderstanding.

   13. GVGary Vaynerchuk19:34

       Mm-hmm. Mm-hmm.

   14. SBSteven Bartlett19:34

       So, anything you say or do, um-

   15. GVGary Vaynerchuk19:36

       Yes.

   16. SBSteven Bartlett19:36

       ... ar- you know, articles in different s- sort of sides of the political spectrum who maybe hate entrepreneurship at times-

   17. GVGary Vaynerchuk19:42

       Sure.

   18. SBSteven Bartlett19:43

       ... doing pieces on me and then the backlash, and then other, like, real sorta take-down efforts.

   19. GVGary Vaynerchuk19:47

       Yes.

   20. SBSteven Bartlett19:47

       And there was days where even my walls-

   21. GVGary Vaynerchuk19:50

       Yes.

   22. SBSteven Bartlett19:50

       ... of, like, resilience and toughness, something kept me up at night. Has that ever happened for you where-

   23. GVGary Vaynerchuk19:55

       Yeah, we're all human be- I'm not a robot.

   24. SBSteven Bartlett19:57

       Yeah.

   25. GVGary Vaynerchuk19:57

       It's that that's so not sustained.

   26. SBSteven Bartlett20:01

       Tell me about a time when that happened. You don't have to give me the details, but-

   27. GVGary Vaynerchuk20:04

       I'll tell you.

   28. SBSteven Bartlett20:04

       ... yeah.

   29. GVGary Vaynerchuk20:05

       There was a kid who wrote a Medium piece about me being the face of hustle porn-

   30. SBSteven Bartlett20:09

       Hmm.
5. 32:26 – 40:57

   Is mindset a privilege?

   1. SBSteven Bartlett32:26

      as the protein. Make sure you try the new ready-to-drink flavors. The, the caramel flavor is amazing. The, um, new banana flavor as well is amazing, and obviously, as I said, the iced coffee caramel flavor has been a real smash hit, so check it out. Let me know what you think on social media. I see all of your tags and Instagram posts and tweets about Huel. Back to the podcast. On, on that point of those wisdom years-

   2. GVGary Vaynerchuk32:47

      Yes.

   3. SBSteven Bartlett32:48

      ... one of the things that came out of my refinement, as you call it, and my kind of maybe... I'm at just at the start of my wisdom years-

   4. GVGary Vaynerchuk32:54

      Yes.

   5. SBSteven Bartlett32:54

      ... as I look back on my perspective on, on exactly what you've talked about, on, like, hustling and, like, my own, um, insane luck of being a very optimistic person-

   6. GVGary Vaynerchuk33:03

      Yes.

   7. SBSteven Bartlett33:03

      ... in the worst situations, and I wonder, I say, "Steve, is mindset a privilege?" And if, and if it is, 'cause you described yourself as being as happy, you've always had this, this drive, this motivation, is there a risk in us, if mindset, if our mindset is a privilege, in trying to ad- advise others when they don't have the same privilege?

   8. GVGary Vaynerchuk33:23

      Couple things. One, everything's a privilege.

   9. SBSteven Bartlett33:25

      Yeah. Do you see what I mean though? Like-

   10. GVGary Vaynerchuk33:27

       Of course I do.

   11. SBSteven Bartlett33:28

       ... I got really scared, I think, in the last two years-

   12. GVGary Vaynerchuk33:30

       Oh, no, this is incredibly powerful.

   13. SBSteven Bartlett33:31

       Yeah.

   14. GVGary Vaynerchuk33:32

       First of all, as a whole separate and intriguing conversation, everything is a privilege and everything is a vulnerability, and this is, like, an incredibly important subject to talk about. I think mental content is the ultimate privilege.

   15. SBSteven Bartlett33:45

       Yeah. Amen.

   16. GVGary Vaynerchuk33:46

       I think the second one is beauty.

   17. SBSteven Bartlett33:47

       (laughs) Yeah.

   18. GVGary Vaynerchuk33:48

       I am fascinated that we haven't gotten yet to attractive privilege. When I look at men and women navigate this world, there's nothing more clear to me in the privilege that c- like, like, they're like white male pr- I'm like, attractive privilege makes that shit look fucking minor leagues if you look at the data.

   19. SBSteven Bartlett34:04

       So, so let's look at that then.

   20. GVGary Vaynerchuk34:05

       So I'm gonna put... I wanna go back 'cause I don't wanna-

   21. SBSteven Bartlett34:07

       Okay, okay.

   22. GVGary Vaynerchuk34:07

       ... lose, and I will lose it 'cause I know how we roll.

   23. SBSteven Bartlett34:09

       (laughs)

   24. GVGary Vaynerchuk34:10

       Uh, I have no interest in thinking that I'm telling anyone what to do or giving... I do not think that I'm giving advice. I really don't. And I don't touch on this enough, and I have touched on it at times, and this is a great format to touch about it. I have no belief that I'm right. I have no belief that I'm giving advice. I have no belief that anyone listening to this should do what I'm saying. I am putting info into the system, and I'm hoping that people can extract something of value for them based on their own self-awareness of themselves.

   25. SBSteven Bartlett34:50

       Most people don't have self-awareness.

   26. GVGary Vaynerchuk34:52

       I'm aware, which is why I talk about it so much.

   27. SBSteven Bartlett34:54

       Yeah.

   28. GVGary Vaynerchuk34:55

       But there's a reason I talk about self-awareness so much, why it was a pillar of my last book, why it's a big character in V Friends, self-aware hair, self-aware hare, The Tortoise and the Hare.

   29. SBSteven Bartlett35:05

       Yeah.

   30. GVGary Vaynerchuk35:06

       I think people don't... One day when I'm... You know, I think 47-year-old Gary for cynics and people that were watching is better than they thought it would be than 27-year-old Gary.
6. 40:57 – 46:58

   How does someone find out what they're good at

   1. GVGary Vaynerchuk40:57

      envy oriented instead of happy oriented. Like, I've got some weird elements that n-... People can't run my playbook, but I couldn't write... run other people's playbook. So pay attention, find what works for you, try shit, try it multiple times. Steve said something you like? Try it once. Didn't work? Steve's not a idiot. You don't suck. Try it again.

   2. SBSteven Bartlett41:15

      On this, the very crux of all of this is that key point, which is about self-awareness. And as I realized that in my late 20s, that self-awareness was really the key to, um, to most things in life. And I remember writing a quote on my Instagram, which is still my favorite quote of all time, where I said, um, "There's no self-develop- um, there's no self-development without self-awareness. You can read as many books as you like-"

   3. GVGary Vaynerchuk41:35

      Oh, 100%.

   4. SBSteven Bartlett41:36

      "... but if you can't read yourself, you'll never learn a thing."

   5. GVGary Vaynerchuk41:38

      It's why I've never read a book.

   6. SBSteven Bartlett41:40

      Yeah, exactly. So I-

   7. GVGary Vaynerchuk41:40

      Like, like to me, the only thing I've read is my feelings.

   8. SBSteven Bartlett41:44

      So how does, how does one s- person listening to this now that's been listening to our content and, you know, they really want to be a, an entrepreneur, they want to have a big media company, whatever it might be, but they don't know they don't have the, like-

   9. GVGary Vaynerchuk41:56

      They don't have the chops.

   10. SBSteven Bartlett41:56

       ... but s- objectively-

   11. GVGary Vaynerchuk41:57

       They don't have the chops.

   12. SBSteven Bartlett41:58

       ... they don't have the minerals.

   13. GVGary Vaynerchuk41:58

       Well, good-

   14. SBSteven Bartlett41:59

       How do they go about discovering they don't have the minerals?

   15. GVGary Vaynerchuk42:01

       By going in the pool and drowning.

   16. SBSteven Bartlett42:03

       Okay. (laughs)

   17. GVGary Vaynerchuk42:03

       (laughs) And I, you know, it's not for you and I to judge 'cause we've been wrong too much.

   18. SBSteven Bartlett42:07

       Yeah.

   19. GVGary Vaynerchuk42:08

       I've been wrong so much, it scares the fuck out of me, and I'm gifted with intuition that when I'm dead, I hope they can test for it 'cause I think I'm all time.

   20. SBSteven Bartlett42:15

       Yeah.

   21. GVGary Vaynerchuk42:15

       And I've been wrong a ton. That makes me believe everyone's wrong. So if you're listening, here's a couple things that are a good call-out that may bring value instead of what I just said. Asking what you're in it for is humongous.

   22. SBSteven Bartlett42:30

       Yeah, but I, this generation, I don't think they know 'cause I, people come up to me-

   23. GVGary Vaynerchuk42:33

       But, and you know this. You'll pr-... First of all, you're part of this generation, young guy.

   24. SBSteven Bartlett42:35

       Yeah. I- (laughs)

   25. GVGary Vaynerchuk42:37

       (laughs)

   26. SBSteven Bartlett42:37

       That's how I know.

   27. GVGary Vaynerchuk42:38

       But, you know, but y-... And I know too, but guess what? My generat-... This, I'm so t- done with this. My generation didn't know either. Guess what? When I was 22, all my friends wanted a hook-up too. All my friends wanted a BMW too. And by the way, as somebody who observed people his whole life, the people that were older than me, the people that were buying expensive wine for me when I was 20 and they were 35, they...Everybody wants stuff to communicate to others that they're winning. We've been putting on makeup since we had fucking clubs hitting each other.

   28. SBSteven Bartlett43:04

       Mm-hmm.

   29. GVGary Vaynerchuk43:05

       Like, it's what humans do. We do things to communicate to-

   30. SBSteven Bartlett43:09

       Status and stuff.
7. 46:58 – 57:02

   Using content to lift people up

   1. GVGary Vaynerchuk46:58

      amount of people that have unlimited resources are desperately lonely, insecure, unhappy, and borderline depression suicidal. That's just truth. And so, like, the thought of me talking in any other direction when I know that to be true seems like the least authentic thing I can do.

   2. SBSteven Bartlett47:17

      But even when you say that, you must know that for a huge amount of people, including myself, we have to have that hypothesis that those things will give us some kind of fulfillment or meaning, we have to have that fail us before we learn the lesson. Gary's words versus the insecurity that was developed from my mother and my father on the playground, hypothetically, one of them i- you know, when I was seven years old, the kids said I'd never be nothing. Then my tea- and I'm not talking about myself here, hypothetical.

   3. GVGary Vaynerchuk47:41

      No, I got it. I got it. I love it.

   4. SBSteven Bartlett47:41

      The teacher comes in and says, "You're a, you're an asshole."

   5. GVGary Vaynerchuk47:43

      I think, I think that's right. I think-

   6. SBSteven Bartlett47:44

      On, on one side of the scale, you've got-

   7. GVGary Vaynerchuk47:45

      Yeah.

   8. SBSteven Bartlett47:45

      ... Gary's words.

   9. GVGary Vaynerchuk47:46

      I don't think it's either of those. I think it's the macro conversation of happiness. I believe if the kid's getting picked on, you'll never be nothing, and she or he decides, "I will be content at 25. I will have peace of mind. I will smile 89.3% of my life," instead of, "I'm gonna have a mansion and a super yacht," I think shit gets crazy.

   10. SBSteven Bartlett48:14

       Y- you, y- you're describing me there. So you... I-

   11. GVGary Vaynerchuk48:16

       Okay.

   12. SBSteven Bartlett48:16

       I at a very young age only, only Black kid in an all-white area.

   13. GVGary Vaynerchuk48:19

       Yep.

   14. SBSteven Bartlett48:19

       We were also the poorest family. So ev- we understand the value of things-

   15. GVGary Vaynerchuk48:23

       So you had all the advantages of adversity?

   16. SBSteven Bartlett48:25

       Exactly.

   17. GVGary Vaynerchuk48:25

       Yes.

   18. SBSteven Bartlett48:26

       In the con- On the context I was in, I was the-

   19. GVGary Vaynerchuk48:29

       Yep.

   20. SBSteven Bartlett48:29

       ... BlackBerry in a world full of iPhones.

   21. GVGary Vaynerchuk48:30

       Yeah. Yes.

   22. SBSteven Bartlett48:30

       So I had that feeling of, like, not enough-ness.

   23. GVGary Vaynerchuk48:33

       I get it.

   24. SBSteven Bartlett48:33

       That means that, um, as I go off into the world, I'm convinced, my subjective evidence is if you get the material success-

   25. GVGary Vaynerchuk48:41

       I get it.

   26. SBSteven Bartlett48:41

       ... that others have, if you get there, then you'll be happy. Nothing on planet-

   27. GVGary Vaynerchuk48:45

       What, what if-

   28. SBSteven Bartlett48:45

       ... Earth could have told me differently.

   29. GVGary Vaynerchuk48:46

       ... what if, what if your 17 heroes on TikTok and YouTube were talking about something else?

   30. SBSteven Bartlett48:50

       It, it, it, it-
8. 57:02 – 1:08:31

   Whats your dark side

   1. SBSteven Bartlett57:02

      sometimes I ponder which is, um, you'll meet someone and you'll think, "This guy, regardless of what I say to them," or, "this, this woman is going to have to have their current worldview fail them before they-"

   2. GVGary Vaynerchuk57:11

      By the way, I, I believe that about every person.

   3. SBSteven Bartlett57:13

      Yeah.

   4. GVGary Vaynerchuk57:13

      I don't believe a single person that I've inspired or got through to now wins. They have to taste everything for themselves.

   5. SBSteven Bartlett57:21

      Yeah. You said you were weird.

   6. GVGary Vaynerchuk57:23

      Yes. (laughs)

   7. SBSteven Bartlett57:23

      And I sat with Tim Grover, Grim- Tim Grover, who used to train LeBron and, um, MJ and Kobe, um, he said to me that we all have our brilliance, our, our, our greatness, and then often connected to that and responsible for that is our dark side. That's the word he used. The thing that, you know, becomes the, the, the difficult-

   8. GVGary Vaynerchuk57:46

      Yeah, it's Star Wars. It's all Star Wars.

   9. SBSteven Bartlett57:48

      What's your dark side?

   10. GVGary Vaynerchuk57:50

       Probably my unhealthy... There's a version of me on a competitive scale that can get dark. I'm incredibly competitive. The only place I feel like I'm dark is when I'm competing. Like, it's cra- Moments ago, couple hours ago, we did rock, paper, scissors tournament with our leadership team as an exercise. I lost to Peter Chun, head of platforms, the guy that talks to Snap and everything. I quickly thought after I lost in the first five seconds, "Should I fire him?"

   11. SBSteven Bartlett58:27

       (laughs)

   12. GVGary Vaynerchuk58:28

       (laughs) Of course, of course, Steve, there's a little ha-ha. But if, but if I'm being naked and, and authentic and transparent to this audience, thank God at 47, the wisdom years, uh, I used to punch h- If Dust- uh, Dustin Bingham, Joe Minakawa, Glen Curtis, Eric Raney, can you guys all stand up and go to social media and tell everybody the following truth of what happened any time I lost in Madden 94 in a dorm room? I would punch a hole in the wall knowing I would have to pay a fine with my own money, but I was incapable of dealing with losing.

   13. SBSteven Bartlett59:09

       Why?

   14. GVGary Vaynerchuk59:10

       'Cause I wanted to win.

   15. SBSteven Bartlett59:11

       Yeah, but why?

   16. GVGary Vaynerchuk59:12

       Uh, because it felt better than losing.

   17. SBSteven Bartlett59:15

       Why?

   18. GVGary Vaynerchuk59:16

       Becau- not because of, like, the great place you're going with this path. Like, it's really funny, it's no different to the d- One of the great lessons I... I've gotten so weird that there's a part of me now that wants me not to buy the Jets more than buy the Jets.

   19. SBSteven Bartlett59:29

       I've seen this evolution.

   20. GVGary Vaynerchuk59:31

       Because I want to show the world how pumped I'm gonna be for Sarah McGee who bought it. And this is a brain fuck, but I'm starting... I lived my whole life saying, "If I can show kids that you can go from not being able to afford a fucking jersey to buying the whole team, I can help." Now I'm starting to believe when I show the grace and happiness for someone else's accomplishment at the expense of my lifelong dream and teach people that it was at the great enjoyment to try it, that I can have a bigger impact than showing that you can do it-

   21. SBSteven Bartlett1:00:07

       That's winning in a different way, though, right?

   22. GVGary Vaynerchuk1:00:08

       In a very different way, and that's what happened with me with winning and losing. I was, I wasn't per se trying to... Of cou- Uh, listen, let, I, I, again, I am not a robot. Everyone's loaded with insecurity. I had, I had insecurity with girls much more than business. Like, nobody was scary to me to talk to in business. But Pam Moses in high school, like, even though there was a clear indication that she had interest, that was still like, "Ooh." Whereas I could have had a meeting with Bill Gates the next day and be like, "I'll beat you." Right? So we all have our places, right? Of insecurity, things of that nature. But, like, you know, when you're five, you, like, there was just such a... Like, I love competition and I'd prefer to win. Right? And I'd prefer to win. I did not have a relationship with it from three to four to 12. Now, I, one thing I love, and I'm watching a lot of kids now 'cause I have kids growing up, here's where I get interested in tenacity and self-esteem.I would lose and I liked it. So, there's some- You want a dark side? I like losing. I might have cried and been pissed and wanted to do something about it, but I wanted to play again. There was almost this weird enjoyment of losing more than winning. As a matter of fact, I cheered for four teams growing up, as religious as I am about the Jets: the New York Yankees, the New York Rangers, the New York Knicks, and the New York Jets. To this day, I am so wildly weirded out by the fact that I love the New York Rangers and the Yankees as much as I like the Jets, but the Rangers won the Stanley Cup in 1994 and the Yankees won the World Series in 1996, and the next day, I stopped following them. For real, no bullshit. I don't- it wasn't a plan. I was 18 years old when the Rangers won the Cup. I didn't think of it as, like, the thing I wanted to do. I literally woke up that next September, October, when the hockey season started, and I didn't want to watch.

   23. SBSteven Bartlett1:02:05

       Why? Uh, this is-

   24. GVGary Vaynerchuk1:02:06

       Now, at 47, I believe it's my addiction is the process and the game, not the thing.

   25. SBSteven Bartlett1:02:13

       And where did that... You're clearly a unique, standout person that loves to win. Where did that, like- it- was there a- an early moment where that was reinforced, that winning is great, Gary?

   26. GVGary Vaynerchuk1:02:23

       No. As a matter of fact, it was, like, not even, like, talked- You know, this is why the '80s were epic (laughs) and more importantly, I'm joking. This is why my mom was epic. It wasn't like she was like, "You ha-" Like, there was no talk of that. It was just pure DNA. I'm massively competitive. I like it. I like the game. My brother has it, my dad has it. Like, we're competitive. I think it manifests in different people, but it wasn't reinforced. It just was, like, innate. And I really like where I have it now, at 47, which is like, I've learned how to deal with the fact that I'm not the best at everything. That's what life taught me through the years. Um, but I really like trying. Like, I lo- You know what's one of my favorite scenarios? This is gonna really... By the way, if this resonates with you, please email me at gary@vfriends.com or gary@vaynermedia.com 'cause I think this is gonna resonate with a lot of people. I thought about this yesterday on a random thing, I must've saw something on social. My favorite thing, one of my favorite, weird, tiny things that I know is gonna resonate with 2% of this audience, but please hit me up 'cause I wanna get to know you: when I'm on a pickup basketball team of random people, like friends play pickup basketball, five on five, college, high school, your buddies get together, when our team gets smoked, like 11-3 in the first game, the second that eleventh point goes in, I get so hyped. S- When you get smoked 11-nothing, 11-1, as you, you know- I don't- You play pickup basketball at all? No?

   27. SBSteven Bartlett1:03:48

       We play f- pickup soccer.

   28. GVGary Vaynerchuk1:03:49

       I know, I-

   29. SBSteven Bartlett1:03:50

       (laughs)

   30. GVGary Vaynerchuk1:03:50

       Football.
9. 1:08:31 – 1:14:15

   Your regrets

   1. GVGary Vaynerchuk1:08:31

      um, is I overcommunicate things that I think bring value to people and I don't communicate things that I don't think bring value to people or things that are important to me that can be owned behind the door instead of in front of the door. So, I think people would be really stunned by how much family time and personal time I have.

   2. SBSteven Bartlett1:08:50

      Do you have regrets?

   3. GVGary Vaynerchuk1:08:51

      Of course. Of course.

   4. SBSteven Bartlett1:08:52

      What kind of regrets do you have?

   5. GVGary Vaynerchuk1:08:55

      You know, you know, there's certain things that I'm not ready to talk about, but I think people are... I'm too public of a figure that people know there's things that have happened in my life more recently and things of that nature. So, of course I have regrets. I've, I also have regrets that I think will really help people, which is, that I am ready to talk about, which is, no bullshit, I should have went to a couple more high school parties. No bullshit, I shouldn't have come home every weekend when I was in college and worked in the liquor store. I should have did a keg stand or two here. No bullshit, like, I should have taken more f- vacations in my 20s with my buddies. You know, like, like, I should have had a little more fun. The truth is, I'll tell you why that was all hard for me to say. They're micro, micro, micro, micro, micro, micro regrets. These are like... Yeah, they've been... Like, the... I have nothing in my body, including some of the stuff I'm not ready to talk about, that's like, "Fuck." You know? Like, I'm in pain over this. They're just like little micro regrets. And I answer this because I want people to see a clear picture on the other side. Like, if this was me and you actually having a drink, the answer might have been no. The only reason I think I just said yes is 'cause I think it's important for people to know, like, nobody's like... I'm just scared that I'm so happy that it seems almost like bullshit. But it's just kinda true because I always go to the same place. The, the... I'll give you an example. I think real regret is only grounded in a very small circle of the people you love.

   6. SBSteven Bartlett1:10:25

      Hmm.

   7. GVGary Vaynerchuk1:10:26

      I, I really do. And I've put the fucking work in on the family si- It's funny. Actually, that was a really interesting segue. The fact that I can say to you no because I've put in so much deposits on the family side, that... Actually, I'll give you a good one. I've got a brewing regret. My best friend in the world is Brandon Warnke. I met him the first day of freshman year of high school. Within the first six months, I'm like, "This guy's gonna work with me." We did baseball card shows together. I knew I was gonna build my dad's business by then. I wanted him. I fucking courted him to be in that business from sophomore year on, and he became my partner in crime, along with Bobby Schifrin, my second cousin, and my dad, and we built Wine Library. Lately, I've been feeling that we have not had enough friend time one-on-one as we start going and starting to see 50, and it's something I really want to work on.

   8. SBSteven Bartlett1:11:21

      I, um, I asked this for very... as if the cameras weren't here and the microphones weren't here. I, I'm earlier, I'm, I'm 30 years old.

   9. GVGary Vaynerchuk1:11:28

      Yeah.

   10. SBSteven Bartlett1:11:29

       And I want to know the, the advice from you, someone that I consider to be a mentor and a friend, you're an investor in one of my companies as well, um, on that... as it relates to that family and that personal piece, what I might get wrong. 'Cause I know you've-

   11. GVGary Vaynerchuk1:11:42

       So I don't think, I don't think there's wrong. I think somebody watching me might say, "You're doing this wrong." I might watch you and say you're doing this wrong. Uh, I gave some advice to a friend of mine, Ryan Harwood, in a pool in Miami a couple of years ago that I feel great about. I checked in once in the last three years, curious if he was doing it. I'm positive I'm right, but I'm not right because what's so interesting about being... We're all unique, but I have a sense of like how I roll. The amount of things that people have observed, including my mom, who's the singular person that knows me best. We share 83% DNA. That's obviously a subjective number, but like I'm trying to paint a picture of how similar we are. Even she is remarkable. And, uh, she is the... I am so intuitive because of her, but earlier to this podcast when I'm like, "I get wrong all the time," nobody has the ability to be more right about me than my mom, and she's wrong about things. She has been wrong. She's been proven wrong. And so what that did for me in the w- you know, I put my mom at the highest pedestal, uh, is, "Oh, me judging Dustin or Steve, like, like, I'm gonna be wrong all the time. I know nothing about them." So, what you need to know is yourself. What you need to know is yourself. For me, regrets are completely grounded in, "Did I spend enough time with the people I love?"

   12. SBSteven Bartlett1:13:04

       Did you?

   13. GVGary Vaynerchuk1:13:05

       I believe that above me, I absolutely have, that my parents today could go... And I used to be scar- Both my parent- My dad lost his dad at 15. I already told you about my mom. I lived in fear. You know, actually, we didn't get on that. That one, that one...... is something I wish I popped up 20 minutes ago in this podcast. The fear of my parents dying, because both they, of them, had a parent die at a young age, was a profound currency in my life in my first 15 years. Profound. And so I think because I'm on the other side of it, there's such heavy levels of gratitude that I got to keep them, that I'm like pumped about it. And I can tell you today, as a 47-year-old man, my parents are young. I expect another good 20 years minimum, hopefully 30. They're like in their late 60s, right? I'm looking for 30. But if God forbid, I won that game in a way that a lot of people haven't. I like was with my mom all the time as a kid. I was with my dad 15 to 35, all the time. I've checked that box. I mentioned Brandon. I think about other people I love like Bobby Schiff and others that I don't spend enough time with. And then of course my kids are so young that I still want to like milk that in a significant way. But I'm sitting

10. 1:14:15 – 1:16:41

    Your mother

    1. GVGary Vaynerchuk1:14:15

       a hell of a lot more pretty, I think, than a lot of people, because a lot of people have also gotten into weird places with the people they love. They fought over money, they fought over an argument, they've cut people out of their lives that they actually love but it was their own hurt. So, I'm incredibly at peace. I'd like to do more and I think all of us do.

    2. SBSteven Bartlett1:14:34

       Five years ago when we had a conversation, I asked you what your biggest fear was and you responded with, with that exact answer which was fear of losing your parents.

    3. GVGary Vaynerchuk1:14:41

       Yes.

    4. SBSteven Bartlett1:14:42

       Um, this profound impact that your mother has had on you has become s-

    5. GVGary Vaynerchuk1:14:46

       And my father, by the way-

    6. SBSteven Bartlett1:14:47

       Yeah, yeah.

    7. GVGary Vaynerchuk1:14:47

       ... real quick. We didn't get there.

    8. SBSteven Bartlett1:14:48

       Yeah.

    9. GVGary Vaynerchuk1:14:48

       My dad telling me that word is bond-

    10. SBSteven Bartlett1:14:51

        Yeah.

    11. GVGary Vaynerchuk1:14:51

        ... might be the single piece inside of me that allowed me not to be the bad version that some people think I am.

    12. SBSteven Bartlett1:14:57

        The first time I've seen you get emotional recently-

    13. GVGary Vaynerchuk1:14:59

        Mm-hmm.

    14. SBSteven Bartlett1:14:59

        ... a- as it relates to on stage was that moment where you talked about your mother. And I, I was, I was going through... I've got these photos here of you as this young man. I was going through all of these pictures and I was reading how you've described her, especially in recent years. This was the, my favorite picture here of you, you and your mom.

    15. GVGary Vaynerchuk1:15:14

        Yeah. In Russia.

    16. SBSteven Bartlett1:15:15

        Yeah. I've never seen you, um, get emotional on stage before other than when you talked about-

    17. GVGary Vaynerchuk1:15:21

        Yeah.

    18. SBSteven Bartlett1:15:21

        ... the profound influence she's had on you. So if this were, God forbid, the last day you had on Earth to, to send a message to your mother, what exactly would you say?

    19. GVGary Vaynerchuk1:15:29

        You did it. She just really wanted to be the best mother 'cause she didn't have one. I would just say she did it.

    20. SBSteven Bartlett1:15:50

        What did she do?

    21. GVGary Vaynerchuk1:15:52

        She made me happy. You know, I want to make everybody happy and it's because I'm aware that she did a better job making me happy than anything I've ever seen about anybody in anywhere about anything. And I just feel like if I don't do that, given that I was given the gift of gab, if I don't scale that, if I don't help every... You know, the biggest thing I could do for her is scale what she did for me.

Episode duration: 1:19:49