Gary Vaynerchuk on Stoicism, Soft Skills, and Becoming Your Best Self | The End Will Not Be Pretty

Ryan reads today’s daily meditation and talks to entrepreneur Gary Vaynerchuk about his new book Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success, how to get comfortable with vulnerability and emotional development, the best way to maintain long term business success, and more. Gary Vaynerchuk is an entrepreneur, author, speaker, and Internet personality. First known as a wine critic who expanded his family's wine business, Vaynerchuk is now more known for his work in digital marketing and social media as the chairman of New York-based communications company VaynerX, and as CEO of VaynerX subsidiary VaynerMedia. Get signed copies of Gary’s books at The Painted Porch: https://www.thepaintedporch.com/ Watch the podcast on YouTube: https://youtu.be/ir3_rzcEzyQGiveWell is the best site for figuring out how and where to donate your money to have the greatest impact. If you’ve never donated to GiveWell’s recommended charities before, you can have your donation matched up to $250 before the end of the year or as long as matching funds last. Just go to GiveWell.org and pick podcast and enter DAILY STOIC at checkout. If you are looking for gifts for family members and friends, the 2021 Daily Stoic Gift Guide is here to help! This year’s guide features a bundle of books signed by Ryan Holiday, our new page-a-day desk calendar, the four virtues medallion, and more. Click here to give the gift of Stoicism this holiday season! Talkspace is an online and mobile therapy company. Talkspace lets you send and receive unlimited messages with your dedicated therapist in the Talkspace platform 24/7. To match with a licensed therapist today, go to Talkspace.com or download the app. Make sure to use the code STOIC to get $100 off of your first month and show your support for the show. LinkedIn Jobs is the best platform for finding the right candidate to join your business this fall. It’s the largest marketplace for job seekers in the world, and it has great search features so that you can find candidates with any hard or soft skills that you need. And now, you can post a job for free. Just visit linkedin.com/STOIC to post a job for free. We've joined Team Feed Corporate to help end hunger in America. No one should go without a meal, yet more than 38 million people in America still face hunger. We created this fundraiser to help provide these much needed meals to our neighbors through the Feeding America network of food banks and we're asking you to join us in our cause. Go to https://dailystoic.com/feeding to donate and let's end hunger together! Sign up for the Daily Stoic email: https://DailyStoic.com/dailyemailCheck out the Daily Stoic Store for Stoic inspired products, signed books, and more. Follow us: Instagram, Twitter, YouTube, TikTok, FacebookFollow Gary Vee: Homepage, Instagram, Twitter, TikTok, YouTube, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

• 0:03Speaker 00

  Welcome to the Daily Stoic Podcast, where each weekday, we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors.

• 0:42Speaker 00

  "The end will not be pretty. Life may be beautiful, but its origins and its ending rarely are. We are born amidst pain and yelling, and occasionally urine and feces. We die when our body quits on us. It doesn't matter how great your life is, how much money you make, or how much power you amass. In the end, we go out with a whimper." As the 16th-century Stoic-friendly philosopher Blaise Pascal observed, "The last act is bloody, however fine the rest of the play. They throw earth over your head, and it's finished forever." What should one take from this? That it's all meaningless? That death should be feared, avoided at all costs? Hardly. What the Stoics want us

• 1:26Speaker 00

  to derive from these meditations on our mortality is a sense for the humbling fragility of our existence, and as a consequence, a renewed focus on the now. "The final act is bloody, so let's make the play as good as possible. We are rotting meat in a bag," Marcus Aurelius once said. "The expiration date is approaching. What is there to be anxious about death? The matter is settled. It won't be pretty, and you don't have a say. We are simply returning to the beginning of the cycle, one that, if you recall correctly, you have no recollection of." Nobody remembers their birth despite being present for it. The same will be true of our deaths, however gruesome, however painful, however unexpected. So get to living

• 2:10Speaker 00

  today, while you still have time.

• 2:16Speaker 00

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. As you know, I'm a pretty introverted guy. I'm a philosophical guy, quiet guy. You might not think that Gary Vaynerchuk and I would be on the same wavelength or friends, but you'd be wrong. I love Gary. And Gary's been great to me. I remember first seeing his stuff and thinking like, I'm not sure this dude is for me. I'm not sure we'd get along. I'm not sure we have the same values or the same priorities. Certainly, I knew we didn't have the same sort of personality. And yet, from the first time I bumped into

• 2:57Speaker 00

  Gary, which I talk about in today's episode, to the first time I was on his podcast, which you can check out that interview, and then a couple of years ago, when Gary reached out, I'd recently left the speaking agency that I was on and asked if I wanted to join a speakers bureau he was starting called Vayner Speakers. He loved what I was writing about. He loved my platform. And he said, you know, I just, I just don't think you're reaching as many people as you could be reaching. And I think if you give me a chance, you'd reach more people. And I was sort of burned out, sort of frustrated with how things had gone the last go around with the agency I just left. And I was a little skeptical.

• 3:40Speaker 00

  And Gary has, no joke, blown my mind, helped me take Stoicism and what I talk about into so many cool places. I'm actually, I'm really grateful. And Vayner Speakers has been great to me. And if some of you are listening, you've seen me, you've seen me speak, or you've had me come speak, you know, you can thank Vayner Speakers. But anyways, Gary is a guy I've gotten a lot of advice from. He's part of the reason that Daily Stoic is on TikTok. He's part of the reason we've done our YouTube stuff. He's really encouraged me to invest more in social media, like, put out more social media stuff. You know, the idea that, hey, look, not every, even this podcast.

• 4:24Speaker 00

  I think primarily in books. That's the medium that I'm comfortable with. I like the written word. But this idea that not everyone is on that wavelength and that these other platforms have these enormous algorithms that you want to use to help reach people who might actually be interested in the writing and the books that I love, but that's not where, that's not their first language, so to speak, has been transformative for Daily Stoic. That may well be how you are listening to this podcast right now. And so I had the chance, Gary was in town briefly, he came out to the Painted Porch bookstore, recorded in person, one of the, one of the few of these I've gotten to do since the pandemic.

• 5:08Speaker 00

  And it was just an awesome experience. The, I feel like the last time I spent time with Gary, Lance Armstrong had a, had a dinner in his wine cellar several years ago and Gary was there. That, I feel like that was the last time we talked in person. Anyways, love Gary. So excited to do this interview. We really get into Stoicism. You might not think about Gary as someone who'd want to go in depth on Marcus Aurelius and Seneca, but that's what we do in this interview. It was fun. It was exciting. I left it pumped and excited, and I think you will as well. And look, Gary has a new book out that is already

• 5:47Speaker 00

  a monster hit. He sold 1.2 million copies of it as a pre-order, which is insane. Nobody does that. So again, I'm always trying to learn from people who are in different spaces, who do things a different way. And so, once again, I think Gary is sort of carving a new path. Plus, the book is really good. It's called 12 and a Half: Leveraging the Emotional Ingredients Necessary for Business Success. I took a bunch of notes on this book. He talks about gratitude, self-awareness, accountability, optimism, empathy, kindness, tenacity, curiosity, patience, conviction, humility, ambition.

• 6:26Speaker 00

  And then something he's struggling with the most, kind candor. How do you be honest without hurting people? How does your reluctance to hurt people not hold you back from speaking the truth? It's a fascinating book. Check it out. We've also, he's signed some copies of his other books while he was at The Painted Porch, which we have for sale at thepaintedporch.com. We've got signed copies of Crush It!, The Thank You Economy and his other books as well. So you can check those out. Anyways, I loved talking with Gary. You can watch a video of this podcast as well. Follow Gary on all the platforms, @GaryVee. That's G A R Y V E E. You're probably already following because he's got like an enormous reach.

• 7:09Speaker 00

  But anyways, I loved this talk with Gary Vee and do check out the new book. I'm holding it right now. 12 and 1/2, Leveraging the Emotional Ingredients Necessary for Business Success. And get on the Gary ride. It's always fun. You might not love all of it. You might not agree with all of it, but I think it comes from a good place. And I think he inspires and I think he makes a difference for people. And I respect that even if I do things differently. And I've really enjoyed the value. You know, Gary talks a lot about creating value for people. Gary has created a ton of value for me. And that's why I'm excited to have him on the podcast, introduce him to you if you're not already familiar and hopefully create some value in return. And I hope you enjoy this interview.

• 7:50Speaker 00

  I'm going to throw my definition of Stoicism at you because I think it aligns with how you see the world, even though I know you don't identify with a Stoic. But you, you, you, you hit me back with what that means to you.

• 8:00Speaker 01

  Okay.

• 8:00Speaker 00

  All right. So my definition of Stoicism is that we don't control what happens, but we control how we respond to what happens.

• 8:07Speaker 01

  I believe in that tremendously. Look, I'm, I'm, here's my, here's my relationship with Stoicism. You and for a while now, especially when I started to evolve and really start opening up of like how I thought, it's in my comments, it's in my DMs. Maybe because of you or maybe not, I'm trying to remember, but somewhere in the ballpark of five, seven years ago, four years ago, I, and you know, we had the podcast when you were online and we're probably repeating some stuff because I don't like this, but it's fun. I looked at the definition, like just literally Googled it.

• 8:45Speaker 00

  Yeah.

• 8:45Speaker 01

  And I was like, oh yeah, like a lot of it resonated.

• 8:51Speaker 01

  The main reason I'm not going deeper into it is I don't want to fuck up what's working for me.

• 8:56Speaker 00

  Sure.

• 8:56Speaker 01

  And I don't want to become almost like a caricature. I don't want to force it. So it's kind of why I stay away from a lot of stuff.

• 9:02Speaker 00

  You seem like a very intuitive guy.

• 9:04Speaker 01

  I am.

• 9:05Speaker 00

  And so I could imagine sort of overthinking it. Or inserting new stuff might mess up the intuition or the vibe.

• 9:13Speaker 01

  Something that I'm really grateful for was I actively could feel my career evolving and remember vividly promising myself that I would never say anything I didn't believe. And it was kind of almost like I didn't want to become the Fonz or become Urkel.

• 9:33Speaker 00

  The catchphrase kind of thing?

• 9:35Speaker 01

  I remember vividly thinking, I will never say crush it if it doesn't naturally come to me. I will never say anything. The one that's really probably funny to people, and I think people may, or it'll be interesting to see how people, how this lands for some people, I never curse unless it naturally comes for me. Like I don't go and say like, oh, I've got to do my cursing thing. I play every audience different. D-Rock and I were just talking. I spoke this morning in Orlando and it was a very conservative B2B and like, he was like, you were more scholarly. And I was like, I, some of the stuff that a lot of people know in my content would have not landed.

• 10:14Speaker 00

  Sure.

• 10:15Speaker 01

  What I did in Edmonton the other day for 10,000 people would have not landed for these 400 people in any shape or form. And for me, I think what makes anybody who's putting out content effective is the humility to be contextual to the audience, not what they're interested in.

• 10:32Speaker 00

  You probably don't remember this, but the first time I met you, this would have been 2008. I was walking to the convention center at South by Southwest. And I was like, oh, it's Gary Vee. How are you, Gary? And you're like, I'm good. I'm like, what's going on? You're like, just crushing it. And this is before the book. So the book came out, I was like, there it is.

• 10:51Speaker 01

  Yeah, like I, you know, I react to what I'm feeling more than kind of the reverse.

• 10:57Speaker 00

  Sure.

• 10:58Speaker 01

  Right? Like, if people listen carefully, it was all there before it came out.

• 11:02Speaker 00

  Yeah.

• 11:02Speaker 01

  Even V Friends, you know, V Friends, I've talked at nausea around intellectual property. My office itself is a visualization of what was coming. I like that. I like that. It's kind of like, I always talk about, I'm a smoke and then there's fire. I'm proud of that because I feel like it's authentic. I feel like it, you know, one, I don't have the audacity to ever think that people should do the homework on me that allows you to kind of see it.

• 11:30Speaker 00

  Yeah.

• 11:31Speaker 01

  Like, when people are like, "Don't you struggle with being misunderstood?" I'm like, "How? Why would somebody who decides to see one clip on Instagram, and I'm being me, and in certain formats, I know exactly what that is, that's going to rub certain people the wrong way? Why should they spend 16 hours to know the full me? They shouldn't." And so I'm very empathetic to it. And that's kind of just how I see it.

• 11:53Speaker 00

  All right. So the new book is 12 and 1/2. We call them virtues, or traits, or ideas. Stoicism is supposed to be four.

• 12:01Speaker 01

  Okay.

• 12:01Speaker 00

  So I'm going to give you the four of Stoicism, and you tell me where they fit, how they work with the 12 and 1/2. All right. So courage, temperance, which is like moderation, self-discipline.

• 12:11Speaker 01

  Interesting.

• 12:12Speaker 00

  Justice, and wisdom.

• 12:14Speaker 01

  Yeah. You know, I think, it's interesting. I think that those, wisdom was one I actually, wisdom is something I'm very interested in. I feel like I'm getting trapped into like affirmation that I have, by the way, I would love to be a Stoic, on the record, or not. Like, I'm just very flow that way.

• 12:36Speaker 00

  I just want to riff on the idea.

• 12:37Speaker 01

  No, I fucking love this shit. I'm obsessed with wisdom.

• 12:40Speaker 00

  Yeah, of course.

• 12:41Speaker 01

  So here's a very interesting part about me. When I was five, six, seven, four... I, four, five, four, five, six, I would go outside in Queens. You know, I always talk about Edison, Jersey, but my first couple of years in America were in Queens. And I would immediately, as a four-year-old child, run towards the eighty-year-old alter cockers, which is a good Yiddish word for old fuckers. And I would hold court and jam. And my mom, when I was eleven, thirteen, fifteen, would tell me these stories of me. And she would talk about like the three or four, two guys that were like the grumps of the grumps. They would sit on this stoop and they would just make fun of everybody, be mean to everybody, hate everybody.

• 13:24Speaker 01

  But every morning, she would say that the occasional mornings where I didn't come outside, they'd be mad at her that she wasn't walking me at seven thirty in the morning. And she would just kind of talk about like what I was bringing to them.

• 13:37Speaker 00

  Yeah.

• 13:38Speaker 01

  And I remember even then, fifteen, when you're not really thinking about massive thoughtfulness, wisdom. I remember one time in my high school years, she, again, telling me a story that I've heard a couple of times. And I just remember saying to myself, I was driving to high school, "No, Mom, they were giving, they were giving to me."

• 13:59Speaker 00

  Yeah, of course.

• 14:00Speaker 01

  And so I'm very fascinated by wisdom. I, I'm very fascinated by us not tapping into the resource that is eighty and ninety-year-olds.

• 14:10Speaker 00

  Those are the entrepreneurs I love, like the people you've never heard of. And then you get talking to them, they're like, "Oh, he had this whole string of like air conditioning supply and company, some company you've never heard of. He had four hundred employees, you know, and, and he just figured out some niche."

• 14:25Speaker 01

  You want to hear something that I know that my team and nobody's ever heard? I did say it's somewhere, but I don't know where. That person is the reason this book exists. Let me explain. I was somewhere, and I'm struggling to recall, but it was an eighty-five, I was there for something, and I don't remember. Maybe family, maybe a keynote or business. But it was one of these, kind of like where we were today, like a country club, a hotel, like a big thing. And somebody was having an eighty-fifth birthday party.

• 14:55Speaker 00

  Right.

• 14:56Speaker 01

  And there were so many people there, they were all wearing these T-shirts, and I do what I normally do. I was listening. Not on some Yenta stuff, contextualizing. And the punchline of this, not to go too long-winded, was there were 22-year-olds talking to 60-year-olds, saying, "My grandfather worked for Joe, and he's the reason our family did this." I just remember vividly, I'm even getting weirdly emotional right now, thinking, "This is what the world does not talk about with business." That it is absolutely just as easy to build an empire. And I'm going pretty fast. Not only was he 85, not only did all these people travel, all these people.

• 15:40Speaker 00

  Sure.

• 15:40Speaker 01

  I think it might have been Arizona. I'm trying to remember. From like, people were like, "I'm from Chicago." For his 85th birthday, that kind of lightly knew him because of the legacy he left as an entrepreneur, having this company that put people on. I remember saying to myself, "That's gonna be me." I remember thinking, "This is something that needs to be talked about." Because even then, this was like, 7, 8, 5, 7, 8 years ago, business was misunderstood. And now, as our country divides even more, capitalism, business, like, there's like a blanket demonization that I think is wildly misunderstood. Not on some like, the money rule, like, more on actually like, "You just can be kind..."

• 16:17Speaker 00

  Yeah.

• 16:18Speaker 01

  "...and build an empire."

• 16:19Speaker 00

  Well, that's like, multi-generational impact. And then, imagine if you could go see the actual community, where he employed all those people.

• 16:26Speaker 01

  100.

• 16:26Speaker 00

  Like, this store on this main street here, like, businesses have, look at the towns that have been totally revitalized, because somebody moved something somewhere.

• 16:34Speaker 01

  And my point is, I think that's accepted. Like, people are like, "Detroit did this," because that's business, business, business. For me, the impact was the humanity.

• 16:43Speaker 00

  Sure.

• 16:44Speaker 01

  That you can use business as a format to touch tens, hundreds, if not millions of people, done right. And I think there's a way to do it. I really, you know, and I used to say this, back to "Smoke and Fire," there's a lot of content on me and the internet, saying things like, "I don't want Steve Jobs' legacy, because I don't like the way he treated employees."

• 17:05Speaker 00

  Right.

• 17:05Speaker 01

  Or, the narrative that people followed.

• 17:08Speaker 00

  Sure.

• 17:08Speaker 01

  Whether he did or not, it became the narrative. I think this is the culmination of that. This is me putting a flag in the ground and saying, "Listen, the alpha way to win." Like sustained way to win is actually grounded in kindness and gratitude and empathy and accountability and we can get there. I've done it. I've seen lots of other people do it. And I actually think in a world where Gen Z is going to have ridiculous amounts of options, you know, everyone's talking about the great resignation. The great resignation isn't because the government's subsidizing, it's because people have options.

• 17:45Speaker 00

  Right.

• 17:46Speaker 01

  You can make $85,000 a year on TikTok.

• 17:49Speaker 00

  Well, and don't you think the ultimate thing to have someone say about you is like, oh, he or she was very successful, very good at what they were doing and they weren't a piece of shit?

• 17:58Speaker 01

  It's my number one.

• 17:59Speaker 00

  Yeah.

• 18:00Speaker 01

  It's my number one. It's the only thing I think about.

• 18:05Speaker 00

  But it's harder to measure, right? This is what you talk about a little bit in the book. It's so much harder to measure. Like, how do you know day to day that you're getting there?

• 18:11Speaker 01

  You know, it's funny, you, I know that. And then something hit me this week. This week Bobby Glennon and Sheerly had their 10th anniversary at Vayner and Tyler had his eighth and DeMayo, who now works at Vayner Sports, had his ninth. And Madabelle tweeted out yesterday, because I was on the Today Show and it was a good, it was kind of like, sometimes it just hit. It was like a good one for me. It was like, this is really what I'm saying. She said, for all the people that have been asking me why I've worked for this guy for seven years in an industry that has 30% turnover every year, this. And you're right, it's not easy to measure, but in the macro, it's very easy to measure in a 15-year window. It's called retention.

• 18:56Speaker 00

  Right. Well, to go to the great resignation, people aren't quitting jobs that they love. They're quitting jobs that were very well paid or...

• 19:04Speaker 01

  And my argument is, when we clip this video in five years, people are going to be quitting jobs that they like a lot. It's just a game of options.

• 19:14Speaker 00

  Sure.

• 19:14Speaker 01

  And I think the law, so we saw it with The Long Tail of Influencers, my first book, the only other one I felt like this about, AKA, I think it's just going to be successful because it's going to hit a chord. The argument I made in 2008 was the long tail of YouTube, for all intensive purposes, was going to be lucrative. And if you go right now on Amazon and sort my reviews, people shit on me saying, yeah, yeah, yeah, we're going to make $80,000 talking about lipstick or honey on YouTube. And it happened greater than I predicted. I think that's going to happen with NFTs. I think about all the people that have been art directors for VaynerMedia making eighty to one hundred fifty thousand a year, a third of those never make it into the door because they're going to sell their NFTs in 2031. I think that the world continues

• 19:59Speaker 01

  to build technologies in server-based, whether centralized or decentralized, that continue to create options for the human. And I think that's going to play out. So to your point, right now, that's the case. I argue that you better get on board to what I'm talking about here, because you're going to need to be remarkable to win the supply and demand game of this.

• 20:23Speaker 00

  As you know, Stoicism has had a big impact on my life, and it's helped me so much through the last 15 years. And it's something I try to share with others. Sometimes that's a book recommendation. One of the things we've tried to do over the years is create some physical embodiments of Stoic philosophy, just sort of physical reminders of these ideas. I've got the Marcus Aurelius bust on my desk. My whole office, my home even, is sort of reminders of these ideas from the ancient Stoics. Maybe that's something you would want this time of year, or as you're looking to give something to someone in your life, to introduce them to the ideas of Stoicism. Maybe that's members of your team or your unit. Maybe that's a friend you know who's going through something. Anyways,

• 21:05Speaker 00

  we put together a 2021 gift guide of these things. You can check that out at dailystoic.com/giftguide. It's 10 awesome gift ideas for the Stoics in your life. The Obstacle is the Way Leatherbound book, the Daily Stoic Leatherbound book. We've got action guides, we've got digital courses, there's the Daily Stoic Life membership. We've got signed personalized editions of all my books. Awesome stuff like that for you or for someone in your life. Check that out at dailystoic.com/giftguide.

• 21:36Speaker 00

  So let's talk about these soft skills for a second, because, you know, like, I think a lot of people's impression of you is like ambitious Gary, hustler Gary, grind Gary. You know, and now you're talking about empathy and kindness. And I get a little bit of this on my stuff. People are like, what are you woke now? What are you politically correct? Because you're saying that you should care about people. What is that?

• 22:01Speaker 01

  That's the climate we're in. You know, I do a lot of, you know, it was funny, we were talking about you in the car and we're just talking about how much you read. And I was like, you know, it's funny, he reads books the way I read comments and like, it's all information gathering. And I've been doing a ton of homework on the late 60s, just to give me pattern recognition of how I want to navigate this era, because we're clearly there. It's all the same shit, wildly different, same shit. And, you know, I think this is what happens, people are on emotional tilt. I'm empathetic to those realities. I'm not overtly worried about that. You know, I, I feel like I've, this is, like, this has been pretty in my content, if people looked for it.

• 22:44Speaker 00

  What I mean is like, what's this aversion to people saying you should be kind to me?

• 22:49Speaker 01

  I know what you're saying.

• 22:50Speaker 00

  It's crazy.

• 22:51Speaker 01

  It's because people think that it's, it's grounded in people politicizing everything. If you've decided your framework on society is, everything is a political issue.

• 23:06Speaker 00

  Yeah.

• 23:07Speaker 01

  You're gonna try very hard to figure out what is it? Is it red or blue? Actually, it's really funny, my team's been hearing this. I've been really having this weird feeling about purple.

• 23:19Speaker 00

  The color purple?

• 23:20Speaker 01

  Yep.

• 23:20Speaker 00

  Okay.

• 23:21Speaker 01

  And not the movie, though, that was remarkable. I'm just very hot on how simplistic what I'm trying to tell the world is through business and really life, which is, purple's awesome. Like, if you're fully blue, or if you're fully red, you're wildly vulnerable.

• 23:37Speaker 00

  You mean a mix of both, is what you're saying?

• 23:39Speaker 01

  Yes. Like, that if I was born in this country, I'd probably, am very aware of how impossible it is to win a presidential election through being an independent. Though Ross Perot gave it a real fucking run, and I think I'm way more charismatic than Ross.

• 23:55Speaker 00

  You know, he ran with a stoic. I'm almost talked to.

• 23:58Speaker 01

  I did not know that, but I'm excited to hear that. It makes even more sense now that I'm a stoic. And so I think there's something very real about purple. I live it in business. When people, you know, it's funny, a couple of my friends, acquaintances, they're like, oh, I'm like, this is not coddling.

• 24:15Speaker 00

  Yeah.

• 24:15Speaker 01

  Like, and first of all, I'll fucking kill you. Like, you know, like, it's like, kind of like, this is sharp elbow. Like, I actually genuinely believe that leadership done this way makes you more money.

• 24:27Speaker 00

  Yeah.

• 24:27Speaker 01

  Like, this is not like, I'm not here for like, let's, like, VaynerMedia's code word internally is, let's build a honey empire. Honey over vinegar. Empire is not a soft word. I'm not fucking giving eighth place trophies. There's incredible amounts of things in blue land that I'm like, eh, I don't want to give eighth place trophies.

• 24:47Speaker 00

  Yeah.

• 24:47Speaker 01

  Like, but the reality is that I know this is real. I'm comfortable with people's reactions to it. I'm aware that people knew me as Wine Gary for seven years. And there was no other Gary. You know, I am aware that I had friends that told me after I sold Resy and had some big IPOs, that I was crazy to do garage sale videos because it was going to make me seem not elevated.

• 25:17Speaker 00

  Right.

• 25:18Speaker 01

  I'm aware that now a lot of people think of me as Gary Vee within the NFT space.

• 25:23Speaker 00

  True.

• 25:23Speaker 01

  I'm going to be known for a lot of shit.

• 25:25Speaker 00

  But don't you think, like, sports have figured this out, right? That it's like, oh, maybe there's other ways to win than screaming at people and using them up as these sort of expendable, like, suddenly they're caring about culture and they're caring about load management and sleep and all the, like, to me, it makes perfect sense that the things you're talking about would come to business and all elements of life. Because this sort of brutal, you talk about this at the beginning of the book, like, the dog eat dog, like, I'm going to destroy you, zero sum mindset for business and life and sport. It's, not only is it not the only way to do things, when talent has leverage, it's the worst way to do things.

• 26:04Speaker 01

  A hundred percent. As a matter of fact, taking from sports, there's something else that I think I want to make a compelling conversation for that I hope evolves. In sports, even though it drives me crazy as a diehard, the Jets play the Bills this week. They're our rival. They've been bad for a long time. They've finally got their shit together. They're beating our faces in. I want to kill everybody because I'm irrational in sports land.

• 26:31Speaker 00

  Sure.

• 26:32Speaker 01

  And the game ends and they're hugging.

• 26:35Speaker 00

  Yeah, where they're swapping jerseys before the game.

• 26:37Speaker 01

  And now that I'm in the business representing players, it's actually more beautiful than you think. They're catching up with friends and asking them to support their non-pro. Like, if you put Mike some of the talks there, the perception versus the reality is staggering.

• 26:51Speaker 00

  Because it benefits them in the offseason.

• 26:53Speaker 01

  Correct.

• 26:53Speaker 00

  Because then they can go text guys, "Hey, you got to come here. This is a good place to play."

• 26:57Speaker 01

  Of course. And like, and they think about life after football now. All these kids want to be entrepreneurs. They're all done at 35.

• 27:03Speaker 00

  Right.

• 27:03Speaker 01

  Except for a couple characters in Tampa. These guys wrap up at 35 and they do their thing and they do business with their... We don't have that in business. I, I compete with people directly that I actually genuinely like, and I try to have relationships with them, and they could be less interested because they've made the business thing the entire encompassing. So in sports, you can beat the fuck out of each other, but then hug it out. But in business, if I beat you in a pitch for the Pepsi business, you are, you hate me forever. And I see you at banquets, at South by, at Cannes, and you're mean to me and you talk ship, like, and that's everybody. And that's crazy.

• 27:46Speaker 00

  I had R.C. Buford on, the GM of the Spurs, did the old Spurs dynasty. They have a alumni locker room at their practice facility. And I was thinking about how amazing that is. Like, after these guys have finished playing, they can live anywhere in the world. What does it say about your culture that they continue to live in San Antonio by choice, first and foremost?

• 28:07Speaker 01

  Big shout out to San Antonio, but like, there's other places.

• 28:10Speaker 00

  I don't think that's an insult to San Antonio.

• 28:12Speaker 01

  It's not.

• 28:13Speaker 00

  And then they come in to work for free, just to hang out, right? Like, that's what, that's what I think thinking about some of these things gets you. It gets you a culture that sustains itself, that you don't have to continue to enforce by force.

• 28:26Speaker 01

  Let's go again to things that may not seem as obvious. I agree.

• 28:31Speaker 00

  Yeah.

• 28:31Speaker 01

  Amazing. A thing that I think some people kinda know, but they don't think in 30-year terms. Fine. Let me give you one that I don't think people think about. If your office is not political, people go faster.

• 28:45Speaker 01

  Let's just, let's go there. What have I observed? My companies are fast. Speed, like in sports, matters in business.

• 28:53Speaker 00

  Sure.

• 28:54Speaker 01

  In a real way.

• 28:55Speaker 00

  First to market.

• 28:56Speaker 01

  In a real way. Pivot quickly. Like, when you eliminate fear, you can go fast. When people aren't overthinking every word in every meeting because, oh, wait a minute, karma and I locked down, now he's gonna write me, like...

• 29:09Speaker 00

  And you don't just mean like politics, like elections. You mean politics, just like bullshit, bureaucracy. Yeah.

• 29:14Speaker 01

  Every company on earth.

• 29:16Speaker 00

  Yes.

• 29:16Speaker 01

  Like, you walk, and we have, listen, we have it good, but it's human.

• 29:20Speaker 00

  Sure.

• 29:20Speaker 01

  You can't, new people are coming in every day. You can't catch them all. It's not Pokemon. You know, and so like, you know, I think what is happening is, what I've noticed is, we're winning because people are less scared, because we're really focused on these things. It really, really matters. And, but it matters in like funny ways. It's like, um, and then also, like, you know, like, this is where, what I really get excited about is when I look at them like this, and I go, you know, it's funny, conviction with humility is a concoction that gets interesting, right?

• 29:53Speaker 00

  Because you can't separate them. They enhance each other.

• 29:56Speaker 01

  Correct. So when I started thinking about them as ingredients, I was like, huh. You know, like, you know, accountability is really fascinating, and of course, accountability works well with conviction and tenacity. And this is like me, the misunderstandings, right? I can go hard, but if I lose, like, I'll be the first to like, put out ungodly amounts of content in seven years, being like, guys, I, I missed it. I don't know why, like, I thought NFT, like, I actually like that. Like, I at nausea have talked about passing on Uber, because I enjoy it. Because I enjoy my losses, right? So I think that gets into stuff. And then obviously,

• 30:38Speaker 01

  kind of the elephant in the room that real, talk about really not knowing me just through my content. When, when everybody that got like previews of this or got a little wind of it were like, candor's your weakness? And they're right. Gary Vee, like in this setting.

• 30:51Speaker 00

  Yeah, yeah.

• 30:52Speaker 01

  Like, Gary Vee is a fucking dominant force of candor.

• 30:56Speaker 00

  No, it's the emphasis on the first part.

• 30:58Speaker 01

  It was Gary Vaynerchuk struggled mightily. A, I am fearful of, here's actually, talk about something that's powerful. My greatest fear was to create fear in my companies. I hate fear.

• 31:13Speaker 00

  You don't want a culture of fear in the business.

• 31:15Speaker 01

  And that's what I think everybody does.

• 31:17Speaker 00

  Yeah.

• 31:18Speaker 01

  And I didn't want to rule by fear because I know it's powerful.

• 31:20Speaker 00

  The paranoid survive.

• 31:21Speaker 01

  And my dad ruled by fear. So I became very visceral to it.

• 31:28Speaker 01

  When I had to wake up four or five years ago and finally the subconscious became the conscious. And I realized that my lack of candor actually was creating a ton of fear at VaynerMedia. Because people didn't know where they stood and you would have.

• 31:43Speaker 00

  You were telling people what they wanted to hear. You were, you're avoiding things.

• 31:47Speaker 01

  That's right.

• 31:48Speaker 00

  No, I think.

• 31:48Speaker 01

  I was massaging. I was trying to coach it through in a different way. I would, I didn't care about money.

• 31:53Speaker 00

  It also creates politics, right? Because people are like, we're not getting the truth. We gotta do this.

• 31:57Speaker 01

  Correct.

• 31:58Speaker 00

  Side action.

• 31:59Speaker 01

  Correct. And more importantly, pandering to me because I'm the ruler, right? And so when I really had that, that was a really dark moment for me in my career. Because when you realize the thing you most didn't want to do was happening. And so then I had to mark it to myself. I was like, candor doesn't work for me and literally chipped away at it. And when the word kind went in front of it, it's been wild. And by the way, the last 18, 24 months where my game has gone from a 10 out of 100 to call it, maybe I'm a 60 out of 100 right now. That 50 has been monumental in my business success.

• 32:35Speaker 00

  Interesting.

• 32:35Speaker 01

  And so that motivated me to say, fuck, I can't believe how much of an impact this is having. Because I had a lot of things going for me. But man, just as one, what happens if I actually get people to truly just deploy accountability? Because everybody that is listening right now has worked with somebody who just blames people for everything. It just is the way it is. And like, if you make that change, everybody around you will adjust very quickly.

• 33:03Speaker 00

  Right?

• 33:05Speaker 01

  Um, patience. I've come to learn. Was so easy for me and is like impossible for everybody. Mainly, this is how I got down the path. Mainly because I didn't realize how many people valued other people's opinions. So of course you want to be successful at 25. You want to show your mom. You want to show your friends. You want to show the world. Of course, you're lacking patience. You want a BMW. You want a Rolex. You want a blue checkmark. You want a million followers. You want to be an entrepreneur. And all this bad behavior happened in the last decade because of it.

• 33:34Speaker 00

  Well, I think it's important to point out how they interrelate with each other. Because this is so when people hear accountability or humility or candor. In isolation, they're okay. But you can, they can also turn into problems, right? So for the Stoics, when we're talking courage, temperance, justice, wisdom. Courage for an unjust cause or a stupid cause, right? Doesn't work. Patience for something.

• 33:57Speaker 01

  That isn't working.

• 33:57Speaker 00

  If you're not holding yourself accountable to the patients or you're not being empathetic. They all interrelate to each other.

• 34:04Speaker 01

  What about this one? Because this one is, I, number two.

• 34:08Speaker 00

  Gratitude?

• 34:08Speaker 01

  No, gratitude is my fucking everything.

• 34:10Speaker 00

  Yes.

• 34:11Speaker 01

  Gratitude is number one on this list and back for a reason.

• 34:13Speaker 00

  Yeah.

• 34:14Speaker 01

  Every day's good.

• 34:16Speaker 00

  Of course, you're alive.

• 34:18Speaker 01

  You're alive. Nobody died.

• 34:20Speaker 00

  You're a black swan of black swans. We should not exist.

• 34:23Speaker 01

  Eight hundred, that's right, 400 trillion of one.

• 34:25Speaker 00

  Yeah.

• 34:26Speaker 01

  850 million people on earth do not have access to clean water. The fuck am I upset about this meeting getting canceled?

• 34:33Speaker 00

  And, and how, how much would you have killed to be in the position you are in right now? Taken for granted, right? Like, we would be, the Stoics talk about how if we lost what we have, we would be devastated. And if we saw someone else with what we have five years earlier, we'd be insanely jealous of them. And then we'd sit around going like, being unhappy with what we have. It's insane.

• 34:54Speaker 01

  Yeah, so, no, but number.

• 34:56Speaker 00

  Self-awareness.

• 34:57Speaker 01

  Yeah, self-awareness. So this is the one. That I'm passionate about. Like, for me, so much has worked for me because I understand myself in space.

• 35:08Speaker 00

  Strengths, weaknesses.

• 35:10Speaker 01

  Yeah, and also when you deploy empathy with self-awareness. By the way, being Gary V is all based on this. Like, I'm aware why somebody would be like, "Fuck this dude." I'm empathetic to that. I get all of it. It makes it palpable.

• 35:24Speaker 00

  To me, this is why ego is so dangerous, right? You can't make stuff for other people, whether it's art or products. Like, when you think about Kanye West or Steve Jobs, we think of them as egotistical people.

• 35:34Speaker 01

  Not at all.

• 35:34Speaker 00

  They couldn't have been while they were making stuff.

• 35:36Speaker 01

  Incredibly not true.

• 35:37Speaker 00

  Because it was rooted not just in empathy for other people, but an understanding of what, where...

• 35:42Speaker 01

  A hundred percent. They're reverse-engineering the consumer.

• 35:45Speaker 00

  Yeah, it has to come from them.

• 35:46Speaker 01

  They may be audacious, they may be aggressive, they may be... Listen, I do it. They may enjoy the communication of what they're up to in your face. But Muhammad Ali and Babe Ruth did the same thing, and people were mad at them until they weren't.

• 36:01Speaker 00

  Right.

• 36:02Speaker 01

  Like, it's not super complicated. Like, if you're good enough to call your shots...

• 36:08Speaker 00

  So how do you cultivate self-awareness, then? That's the paradox.

• 36:11Speaker 01

  Well, what's funny about this book, and I appreciate you reading it, you saw, I actually took a real stab at it. Like, I really sat there and said, "Okay, great, I can put these 13 things down, and what? Enjoy yourself," right? So I did these exercises. I really tried to create this thing that I replicate, because it's been asked of me a lot through the years. And the game I won with some people, more inner circle, occasional fans, is sit down three to four people that are closest to you in the world, have a kumbaya for two hours, and eliminate all fear from them on giving you the truth, and then create an anonymous structure for them to tell you your strengths and weaknesses. And then whatever feat... Like, once you start playing with that, whatever is resonating or not resonating,

• 36:55Speaker 01

  you start double-clicking into, right? You start challenging yourself to be uncomfortable. Like, to me, can I actually... I'm gonna go very vulnerable here. The candor thing happened very simply. I went in, saw an interaction between two former employees on some social network, and they didn't like me. And I loved them and I went to bat for them for a long time and I entitled them. I over coddled them because I wasn't able to give them feedback and then I got to my wits end and I fired them and I'm the bad guy and I sat there and I said, I am a man

• 37:34Speaker 01

  who long ago became fulfilled financially, fucking a hundred thousand dollars, that was it. It all changed after that. Not another time in my life has anything felt like anything.

• 37:48Speaker 00

  It was all extra from there?

• 37:50Speaker 01

  All extra from that little of a number, okay?

• 37:52Speaker 00

  That must be very nice.

• 37:53Speaker 01

  It's incredibly nice, that's why I've been so happy. I'm a man that's not motivated by that. I care about how many people show up to my funeral. I've got all these things going on, I'm talking all these things and why are these two wonderful people who had plenty of love for me at one point, why are they sitting here having a convo shitting on me? I'm like, it's, I'm doing, I pushed myself further. I'm like, I've got a flaw and I'm gonna fucking fix it and I knew what it was but I didn't, couldn't like get it to your, you know how you can't get it to your fucking tongue? I'm like, it's fucking candor. Fuck. And then I started going down, why do I hate it so much? And I go into, my mom doesn't have it, she's my hero, she raised me. Then I look, my dad has it, but the way he delivered it was so negative, everybody hated my dad that worked for him.

• 38:37Speaker 00

  You overcompensated.

• 38:38Speaker 01

  I overcompensated. Like I've come to learn that when something's over here, you wanna go in the middle, not over, like, but I went, I fucking went.

• 38:44Speaker 00

  That's what temperance is, the perfect respect.

• 38:47Speaker 01

  So, I didn't have the right temperance on it and it became my half and I'm excited to talk about it and it's so crazy because it is my strength as a public figure. I love your no bullshit, like, it's like, it's all I get and it's because of the context of the setting. Speaking into the ether, piece of cake. Speaking to Sally who I know like has a sick kid, fuck me.

• 39:12Speaker 00

  Right.

• 39:13Speaker 01

  The over empathy and over, you know, compassion and the over sympathy, which are nice things, I went too far, I couldn't find my temperance, you know?

• 39:26Speaker 00

  No, that makes sense. I'm in this writers group, like James Clear, Mark Manson. We get together once a year. We sit around and everyone gets to talk, we all take turns. You get to talk about the person as if they're not in the room. And they can't say anything. All they can do is take notes. And it's super powerful because you get to see how people you actually care about, not just random people on the internet or whatever.

• 39:48Speaker 01

  And is candor, and do you feel like everyone's caught good candor?

• 39:51Speaker 00

  Yeah, yeah. And, but because they are in the room, you're still gonna be kind, right?

• 39:56Speaker 01

  And you can't go all the way there.

• 39:58Speaker 00

  Right, but you can, you can plant the seed of what they can take back and go, you know what, they're right. I am doing too much of this, or not enough of this, or why am I being held back here? And then you take that back and you work on it. It's ironic because we're talking about self-awareness, but one of the best ways to get it is from other people. I would say a spouse being the primary way because they know you better than anyone and they can also speak to you the most directly.

• 40:23Speaker 01

  I think that it is just a big goddamn deal, and all of this is, and it's really time that we actually talk about it as, like, the alternate title to this is, "The Soft Skills Are Hard."

• 40:37Speaker 00

  Ooh, that'd be a good title.

• 40:39Speaker 01

  Thank you. You know, and so, that to me is what, um, right, because it's a double, right? Oh, fuck. Anyway, I, uh, I'm just ready for this because I know it to be true. I know it to be true. Of course, you can build an empire by not being nice.

• 40:57Speaker 00

  A lot of them are that way.

• 40:59Speaker 01

  Of course. But if you're on the other side of reading it, wouldn't it be nice to enjoy it? Like, have you met the 70-year-old Titans that did it the other way? They're disliked, they're disliked. That person's fucking life blows. Like, I love that you put these people on a pedestal. They're not happy. They're not as happy as you think. Like, for real.

• 41:19Speaker 00

  Yeah. No, no, it's, uh, you would, if you actually knew what it was like in their head, you would not trade places with them for all the money in the world.

• 41:28Speaker 01

  It's why I always get crazy about that. I'd rather cry in my Ferrari than, but like, how about not crying? How about smiling in your fucking, whatever, Ford?

• 41:39Speaker 00

  Or you're jealous of this person who's traveling on a private jet to some exotic, but, what if you had a life that you didn't need to run away from?

• 41:46Speaker 01

  Right. Like, like, what are we talking about? Yeah.

• 41:51Speaker 00

  All right, a couple more quick riffs. Mark Sereless says, uh, strict with yourself, tolerant with others. How do you like that?

• 42:00Speaker 01

  A lot.

• 42:00Speaker 00

  Yeah?

• 42:01Speaker 01

  Yes. I would actually argue that that's where I need to find a little bit of balance. My strictness with me is such a healthy one, and my tolerance with others may be too extreme. Back to lack of candor, I'm trying to get a little better. Coddling, entitlement. But my strictness with me is really cool. It's not like I eat at five or wake up. It's, it's this ability to not compromise on a couple of things. And the biggest one is kindness.

• 42:32Speaker 00

  Yeah, or it's like, if you're driven and ambitious, you work 15 hours a day. It can be really easy to just expect that from other people. One of my favorite videos, you're talking to someone, they're like, you're like, the other people, they're not owners of the business. You can't expect what you expect of yourself, of them.

• 42:47Speaker 01

  It's absurd. I once said to somebody, I'm like, you're talking as if we're talking about slavery. Like, what the fuck are you talking about? Yeah, my, I have zero expectations of others, if I'm being really honest. I take it.

• 43:02Speaker 00

  That way you're always pleasantly surprised.

• 43:03Speaker 01

  Yeah, like, and I'm accountable. It's like, look, I mean, yeah, I, I love that, and I'm a believer of it.

• 43:11Speaker 00

  Yeah. And, look, it's called self-discipline. Right? Not, not, you know, nothing else. It's self-discipline.

• 43:18Speaker 01

  I'm thinking a lot about why people point fingers, why people have fallen in love with judgment of others. And I've come to realize it's because they're practicing on themselves. You know, my inability to overjudge myself is exactly why I don't judge others. We're, we're holding ourselves up to, we're the judge and jury, and we're putting ourselves into jails.

• 43:42Speaker 00

  Right.

• 43:43Speaker 01

  Right, like it's nice to have aspir- I mean, I'm ambitious as fuck.

• 43:47Speaker 00

  Sure.

• 43:47Speaker 01

  It's nice to have standards, I'm not saying that, but like, this notion of beating yourself up when you fall short on something that is a standard or an ambition is incredibly unhealthy.

• 43:58Speaker 00

  Well, it's like you would never talk to someone else the way that you talk to yourself.

• 44:02Speaker 01

  But what's funny is, mine is actually slightly twisted on that. I talk to everybody the way I talk to myself, which is why I talk so nicely to everybody.

• 44:10Speaker 00

  But that's how you want it, right? But most- a lot of people talk to themselves in a way that they would never tolerate.

• 44:17Speaker 01

  Correct, because most people try to prop themselves up by tearing everybody else down.

• 44:20Speaker 00

  Right. Alright, so Marx realized again, uh, the best revenge, the best way to get even, is to not be like them.

• 44:29Speaker 01

  My- I think there's something that I like that. Uh, my version on revenge is a little bit more like the inability to even care about their action.

• 44:41Speaker 00

  So shrug it off?

• 44:43Speaker 01

  In- in a more audacious way. Not only shrug it off, recognize that you're about to actually stick it to them by not even acknowledging it happened.

• 44:57Speaker 01

  It's- it's an extreme version of cutting them out of your ecosystem.

• 45:01Speaker 00

  Sure.

• 45:04Speaker 01

  That's how I've dealt with like, people that have done really not-nice things, or trying to go like, it's almost as if it didn't happen.

• 45:10Speaker 00

  Yes.

• 45:11Speaker 01

  It like goes on this nice little shelf, and like, that's nice. You can play with yourself in that cocoon of like, whatever you feel about me. You've now become a energy that is just like, not a good use of time. And even giving it time, and to be frank, I've evolved a little bit from that. I'm now-

• 45:33Speaker 01

  Receiving that energy and kind of deploying really deep sympathy. The thought at this point in my life that you want to spend any of your time hurting somebody else's feelings seems outrageously foreign and really just makes me feel compassionate.

• 45:49Speaker 00

  The ultimate person who suffers from it is them.

• 45:52Speaker 01

  A hundred, all that we're doing out here is, somebody said something to me yesterday, I did something kind of cool, giving away some stuff, and they were like, kind of asking, I was like, late, I was getting home, I was just replying like, it's just because I have so much love to give, I don't know what to do with it all.

• 46:09Speaker 00

  That's sweet.

• 46:10Speaker 01

  And I really think that that's, that a lot of people live the reverse. They have so much pain, they're trying to get it out. You know, for me, it's an abundance of love, of like, fuck it, like, I don't want to, like, what am I, like, this is, like, I better do stuff.

• 46:22Speaker 00

  Right.

• 46:23Speaker 01

  I think that's how hate works.

• 46:25Speaker 00

  All right, so I think anyone who talks about stuff publicly, let alone puts out a book like this, and then mine, I think the tricky part is, it's easy to talk about, it's hard to do.

• 46:36Speaker 01

  Yes.

• 46:37Speaker 00

  Right? Epictetus says, "Don't talk about your philosophy, embody it."

• 46:40Speaker 01

  Yes.

• 46:41Speaker 00

  Or, "Don't talk about it, be about it." Sometimes I wonder, like, if I'd never written about it, but I believed it, could I get convicted of these things in court? Right? Like, if somebody didn't know who I was, they just bumped into me on the street, how close am I actually to the things I write and talk about? How's that journey for you?

• 46:59Speaker 01

  Uncomfortably remarkable.

• 47:02Speaker 00

  Okay.

• 47:03Speaker 01

  I would say that I understate me. I understate the things I live.

• 47:13Speaker 00

  Okay.

• 47:14Speaker 01

  I really believe that.

• 47:16Speaker 00

  How do you get there?

• 47:17Speaker 01

  Well, I get there by doing it.

• 47:21Speaker 00

  Sure.

• 47:22Speaker 01

  I'm doing it.

• 47:23Speaker 00

  Yeah.

• 47:24Speaker 01

  And I get there by understating it. Like, I, I, look, I have Andy and D-Rock here behind the cameras, you know, I'm, they'll probably agree with me, I'm starting to actually, this book and a lot of others, like, the last two years, I would say that I'm starting to peel away my curtain a little bit more and show this stuff more, because it's hard to talk about this stuff. It's like, hey, I'm humble.

• 47:48Speaker 00

  Yeah.

• 47:49Speaker 01

  The fuck is that content?

• 47:50Speaker 00

  Sure.

• 47:51Speaker 01

  So you got to find your balance, because that's not nice. But to answer your question, the thing that I've always loved is...

• 48:00Speaker 01

  I'm more about the things I talk about and I talk about them at scale.

• 48:06Speaker 00

  But earlier you were saying kind candor that you were a 10 before, now you're a 60. So you're still at a D, right? So you're still, you're still moving up.

• 48:14Speaker 01

  Yeah, but this book's also not called 13.

• 48:16Speaker 00

  No, that's a good point. So you feel like.

• 48:17Speaker 01

  Like the book, like the book is like, I stink at this.

• 48:20Speaker 00

  Yeah.

• 48:20Speaker 01

  Yeah, like I don't want, listen, uh, he worked for somebody that used to work for me. I don't want him to know one story from Sam that undermines Gary Vee. I have never wanted, I live very loose. I have admins that have access to everything. My team has, these guys have access to everything. I have no interest in letting any other human being ever have leverage on me. The thought of saying one thing and doing another to then worry if I can control them to never say it is fucking asinine.

• 48:53Speaker 00

  Sure, but I don't know kindness, it's easy to say and then someone does something cruel. Right? Like we have these instantaneous reactions to things. You find, you have to check yourself.

• 49:03Speaker 01

  You know, we got to this a little bit in this talk and it's, I'm starting to like, this is starting to come top of mind for me. I would, do you know how many words I could have put in this book? This didn't have to be these 13 traits.

• 49:13Speaker 00

  Sure, sure.

• 49:13Speaker 01

  There's a lot of other shit. These are the ones that I live, like this is like, you know, this is the ones I live and the ones that I notice and I can see them and yeah, I mean, I'm, I don't feel vulnerable.

• 49:26Speaker 00

  It's good. No, no, no, that's great.

• 49:27Speaker 01

  I think I probably somewhere in hindsight realized 15 years ago, oh, I'm going for it. Right? And when I realized that I probably, you know what I had a good read on? That the internet was going to expose everything, like a very good read. Like I talked about it back then, like in Wine Library TV, like I would reference it. And I think by knowing that and by knowing I was going to go for it, I must have become a much better version of myself on all these things. Because I was like, I don't want the vulnerability.

• 49:58Speaker 00

  But it's something you're, you, you worked on and are working on. These are the ideals and you're aspiring to get there day to day, right? It's not just.

• 50:06Speaker 01

  Yes, but I'd be not authentic if I didn't say that for the 12 of them, they come uncomfortably easy to me, always have and are foundational and why I think have outsized results. I'm really proud of myself because I don't think I could have made, this book would have been called 12 seven years ago.

• 50:24Speaker 00

  You wouldn't have admitted the half.

• 50:25Speaker 01

  I grew up in a family where complaining. Was the single worst thing anyone could do.

• 50:31Speaker 00

  Sure.

• 50:31Speaker 01

  Because we came from the old country and mom and dad had to go outside for a toilet and didn't have bread. So what the fuck are you upset that your Nintendo is not working? So we demonized complaining in my family. Somehow I feel like that bled into not being or talking about vulnerabilities.

• 50:47Speaker 00

  Sure.

• 50:48Speaker 01

  And so I don't think seven years ago I could have talked about the vulnerability of candor the way I did here. And I, to your point, I aspire to be more vulnerable over the next 40 years, which I think will push me into new places.

• 51:07Speaker 00

  I love that. All right. So last thing, because last time we talked, it went a little bit viral. We talked about your favorite three words. You're gonna die.

• 51:14Speaker 01

  Yes.

• 51:14Speaker 00

  Or as the Stoics say, memento mori. To me, that ties into gratitude, right? Not just look at what you have, but the fact that you're still alive.

• 51:23Speaker 01

  It's huge.

• 51:23Speaker 00

  Every day, Seneca says, if you go to bed at night and you go, I've died. It's the end of my life. When you wake up in the morning, it's all gravy from there.

• 51:32Speaker 01

  It's literally how I think. Bro, I had a recurring dream 20 times a year, not like two, from third to eighth grade, that my family decided to go back to Russia for a family vacation and the plane goes down, of course, in Siberia, straight out of Rocky. And every time I survived, but the two other family members were always random.

• 51:56Speaker 00

  Okay.

• 51:58Speaker 01

  I once prayed on my porch when I was in seventh grade for 20 minutes because I thought my mom died in a car accident because I was watching my brother and sister and she was an hour late and they didn't have cell phones back then. And what happened was there was an accident. She was just in traffic.

• 52:11Speaker 00

  Yeah.

• 52:12Speaker 01

  My relationship with the depths of only caring about the health and well being of seven, 10, 12, 15 people. There is nothing else. The reason this is all so fucking easy for me, all of it, all of it, is because there is nothing else.

• 52:30Speaker 00

  Right.

• 52:30Speaker 01

  For real, for fucking real. I know that it might not land for people. I confuse the fuck out of people, but you want to buy the Jets. I'm like, no, no, I want to try to buy the Jets. I love my process. But, but, yes, like, it's my art. Like, I love being an entrepreneur. It's fun. It's my game. I love entrepreneurship and everything that you see that I'm doing, the way people like golf.

• 52:52Speaker 00

  Sure.

• 52:53Speaker 01

  The way people like sailing, the way people like skiing. The seriousness that I take it with is so nonexistent. Of course, I can deal with so much. It's not pressure. My dad and sister, I love them, but they, they have their, my dad, my sister's in real estate, my dad is the wine store. Their most stressful thing, once a week, is like something that happens to me 974 times a day without it even hitting my radar. That's not to say I'm great and they're not. That says to me, I can see, like, how people see the world differently. And what a fucking blessing to me that our two biggest clients calling tomorrow and firing us would be like, and I'd be like, you know, and it would be, but like, but not really.

• 53:38Speaker 00

  Yeah. I mean, if you're playing with house money, okay, so you said, you got, you, you had to give some of it back, but it's not yours anyway.

• 53:46Speaker 01

  I've also been a little bit even, like, I've had my own little weirdness on this. Not only is it house money, and I've talked about this in nausea, I am like romantic of the concept of losing it all and building it back up. It won't happen because I'm too conservative. Again, another thing that doesn't seem obvious, like, I'm too thoughtful, but like.

• 54:06Speaker 00

  You like the narrative of potentially being able to do that.

• 54:09Speaker 01

  You know what I would like the most? I love being an athlete. I love, you know, when I watched Trey Young. Be the villain in Madison Square Garden against my Knicks. I had a very funny thing with it. They were my Knicks. They finally were back. We're in the playoffs. And I'm watching Trey and I'm like, every chemical, chemical, like things you can't control. And my body is, I understand this and I want this. Like, I want all of Madison Square Garden booing me. Because the feeling, like it's why I love Novak Djokovic. I don't like Feds. I don't like Rafa. I like Novak. Why? Because Novak plays in center court against Rafa or Fed, normally Fed, in Wimbledon.

• 54:50Speaker 01

  The whole stadium, the whole country, the whole world is rooting for Roger. And when, when Novak sometimes hits like a shot that's improbable in a big spot, and he just stops and just looks at everybody, that's the apex for me. Because that's competitiveness at its finest. I understand it. I fucking live for it. And so like, this is why I fear, like, this is why purple, right? Like, competition is fun. By the way, let this very important point. I don't want you to be all hurt by my winning. I just want to win.

• 55:26Speaker 00

  Right.

• 55:27Speaker 01

  People don't understand. It's, it's a winner mentality, winner takes all thing, but not at actual expense. This is what I love about business.

• 55:36Speaker 00

  Because it's not zero sum.

• 55:37Speaker 01

  It's not. Like, VaynerMedia is fucking on fire, but guess what? 8,000 other agencies are crushing.

• 55:43Speaker 00

  This is something I have to talk to authors about. No book is stealing a space from someone.

• 55:49Speaker 01

  Not one.

• 55:49Speaker 00

  If people are reading, we're all winning.

• 55:52Speaker 01

  I get pumped when people, and it's, I've gotten to the extreme version where now...

• 55:56Speaker 00

  By the way, when I heard you sold 1.2 million copies of this, I was like, yeah, I was like, fuck yeah. Because that's incre, that means that that is humanly possible to do for a book that doesn't have Trump in the title. You know, and that it's positive and that isn't, also isn't written by Matthew McConaughey or something, right? That's incredible.

• 56:14Speaker 01

  And Matthew didn't sell 1.2 million books.

• 56:15Speaker 00

  No, he didn't.

• 56:16Speaker 01

  And so, sorry Matt, I know he's local here.

• 56:18Speaker 00

  That's the competition.

• 56:19Speaker 01

  Of cour- and by the way, that's not like, anything, like, I fucking love Matthew. I could, when he reached out and, "Can I do your podcast?", couldn't wait. I wanna put everybody, I'm in a very weird place now. I'm a more extreme version of myself, maturity, like advancement. I fucking want everybody to win. Why not?

• 56:37Speaker 00

  Of course.

• 56:38Speaker 01

  Fuck, why not? I promise you, if you're listening right now, and you think somebody else's winnings are coming out of your pocket, you've lost before you start. I promise you with all my fucking heart. You better get into therapy, you better start listening to other shit. I'm telling you right now, if that's you, you need to fucking really reframe this conversation. It is the fakest thing in the world. It's the boogeyman, and it's also unfortunately, the trait that is actually limiting you.

• 57:05Speaker 00

  Yeah, great expression, I think I like this. Envy is the only sin that's not any fun. Right? It punishes you, it sucks. No one is having less fun than the jealous person.

• 57:17Speaker 01

  It's a poison. Jealousy and envy really scares me. It comes from the deepest depths of insecurity. And you know, when I was growing up and I saw my friends being jealous with, like, their girlfriends, it was just like, like, clean data. I'm like, "You're just insecure." I've seen it in business. It's just, it's insecurity at scale. And it needs to be addressed, cuz it's not good.

• 57:43Speaker 00

  Right.

• 57:43Speaker 01

  It's just not.

• 57:45Speaker 00

  Okay, so last, last part of this. What is, how does, cuz I love when you say this, and I think about it too, but there is a tension between, "Life is short, memento mori, you could go at any moment", and, "When the best piece of advice you give people, which is, 'You've got so much time.'"

• 58:00Speaker 01

  So much.

• 58:00Speaker 00

  So what's the tension? How do you, how do you balance out?

• 58:03Speaker 01

  Easy.

• 58:04Speaker 00

  "Life is short, you got time."

• 58:05Speaker 01

  If you think life is long, it helps you in so many ways. If you happened to die suddenly, you wouldn't have known anyway.

• 58:15Speaker 00

  Okay. Sure, it's the end of your problems.

• 58:17Speaker 01

  Right? People are like, "No Gary, life's a short." I'm like, "Good news."

• 58:22Speaker 01

  It's over anyway.

• 58:22Speaker 00

  Yeah.

• 58:23Speaker 01

  Like, if a tree falls on my head when I walk out of here, I'm not gonna know.

• 58:26Speaker 00

  Right.

• 58:27Speaker 01

  You know, maybe I'll be up in heaven and be like, "Mother, I should have never went to Ryan's store. That was so stupid. We could have done it on Zoom on last Tuesday. We'd have 40 more years. Will the Jets ever win a Super Bowl without me?" You know, that would be what was going on in heaven, right? Like, so my thing is, my concept is practical. Life is long, and you believe it, you get more patient, more thoughtful, happier, and life is good. If you're right, that life is short, well, when you die out of nowhere, you're not gonna know anyway. So what the fuck are we talking about? And, and this whole concept that life is short leads to like, you living your best life, is the greatest joke of all time. Every person that I know that is like deeply believes that is frantic and doing all sorts of weird shit.

• 59:11Speaker 01

  It's not like the "life is short" crowd is in fucking Maui or like, you know, chilling and fucking lobster catching and because they love like, the "life is short" crowd is completely out of fucking control and doing crazy ass shit. They're far from happy.

• 59:26Speaker 00

  To me, it's, "Life is short, so have a great self-contained day today, where you did everything that you could today, and then you're grateful if you get tomorrow, but you're not putting anything off. You're also not..." To me, okay.

• 59:41Speaker 01

  People, I'm sorry, because you got me excited. Like, I'm not talking about complacency out here. People are like, I'm talking about patience. People are really bad in taking a word and deciding it meant something else. When I say patience, I see people like, thinking I'm talking about complacency and laziness.

• 59:59Speaker 00

  Or resignation or something.

• 1:00:00Speaker 01

  Right. I'm like, no, that's why those words exist. I'm talking about patience. Like, it's just unbelievable how nuanced these words are and how people decide them. But they decide them because they decided it before they even heard it. You've decided before you even heard it. The lack of openness, this no culture we live in. It's happening right now, heavy with the NFT thing, and it's just reminiscing for me for '05 and '95. Why can't you be in the maybe business? Why can't you just say no to NFTs and you haven't done a single hour of homework?

• 1:00:33Speaker 00

  Right. Yeah. Or just not have an opinion. Just be honest where it goes.

• 1:00:37Speaker 01

  Well, listen, now you're getting into something I'm really passionate about that I have like, God, I love you. Uh, no, this is fun for me. I actually have almost no opinions on like, I think the no opinion is the superpower. And I've come to realize that's me on almost everything. The amount of opinions I have is very limited. I just don't have a lot of bandwidth to like do.

• 1:00:57Speaker 00

  But you're in on, you're in with two feet on the stuff you do have an opinion about.

• 1:01:01Speaker 01

  And both hands. Like I'm fucking all in on what I do. But, you know, everyone just feels like they need to like, like I, the rare occasion that somebody asked me a left field question on stage, where I get to say, I don't know, is my favorite. It happens only unfortunately, once every two years because people stay in the pocket. But some guy asked me about some Stephen Hawking shit and I was like, I don't know. And the react, um, remember the Steve Rock was like three, four years, it's been a while, the COVID, but I loved it. Cause I speak with such conviction and passion that it threw everybody off. And I was like, kind of almost like spoke to them like, I don't know about most things. I just stay in a very narrow lane where I have massive affirmation. I think that's why I'm freaking out about this.

• 1:01:45Speaker 00

  But that's where humility comes in, right?

• 1:01:46Speaker 01

  I think so.

• 1:01:47Speaker 00

  Ego says like, I'll just pull an answer out of my ass, right? I can't look weak. I can't say I don't know. It takes some humility to be like, I literally don't know what any of the things you just said are.

• 1:01:57Speaker 01

  My humility is gaining some momentum. I was in a meeting right before COVID. I was really proud of myself. I'm like, okay, I'm taking the next step. We're in a marketing, marketing, marketing meeting and somebody used some acronym. I had no idea what was. And I was like, hey, what was PLC? And it was something I should have known.

• 1:02:14Speaker 01

  And I was fucking fired up because before I'm such a quick read. For the majority of my career, I would, it was not like I'm like would pontificate on it, but I wouldn't stop. Because I knew that I could figure it out if I could.

• 1:02:27Speaker 00

  Take it till you make it.

• 1:02:28Speaker 01

  But it, but it wasn't fake it to like, I wasn't faking it.

• 1:02:31Speaker 00

  You'll pick it up. You'll figure it out.

• 1:02:32Speaker 01

  Pick it up. It was more that honestly, if they then said, what do you think? I would bail. Because again, I never, I truly believe this. I'm petrified of being historically incorrect because I think it's my leverage. And you know, now my career is in a funny spot where like, I always felt it. Now I think a lot more people feel it. There's a lot, there's enough wins on the board now where I'm starting to gain momentum on something that is business leverage. So I don't want to fake it till I make it. Like, I really don't. And I think a lot of people believe that works.

• 1:03:01Speaker 00

  The stakes of being wrong, the stakes are higher on being wrong. If, and you just don't, you don't want to be out till, you don't want to be caught.

• 1:03:10Speaker 01

  On competition, not on money.

• 1:03:11Speaker 00

  Yeah, right.

• 1:03:12Speaker 01

  People are wrong all the time. Reboot, money, money, money. I don't care. I want the legacy. I want the statue at the stadium when I'm done. Not, there's a lot of people with three Super Bowl rings. But there's only so many people that have a statue outside of their stadium. I want a statue in entrepreneurship. I want a statue. And I don't think you get a statue by making the most money. I think you get a statue by the 360 thing that I'm talking about.

• 1:03:35Speaker 00

  Yeah, it's impact, relationships, work you do.

• 1:03:39Speaker 01

  But by the way, you've got to put up the things. I can't be considered one of the greatest entrepreneurs of all time if I don't put up a real, meaningful resume.

• 1:03:47Speaker 00

  Right.

• 1:03:48Speaker 01

  But I think if I nail this narrative for the next decade, I think I can have one of the biggest impacts on entrepreneurship. I have a lot of people listening to me at very young ages and the reframing of what it takes to win. And people, look, we all did it. I did it, we all did it. You look up to something. I'm incredibly aware what's going on with my TikTok following. I'm incredibly aware of what's going on. And if I can land that, I'm excited.

• 1:04:11Speaker 00

  Well, it's like, it's not just how many Super Bowls a coach wins.

• 1:04:14Speaker 01

  Am I missing my thing?

• 1:04:15Speaker 00

  Do you have to go?

• 1:04:17Speaker 01

  It's 8:44. Did I miss it? Yep, I sure did. I'm out of here. I have like a live Twitter Spaces. I kind of trusted myself. But there's accountability. It's my fault. Here we go.

• 1:04:32Speaker 00

  Daily Stoic is raising money for Feeding America. Last year, the Daily Stoic community came together and raised over $100,000 together, providing more than a million meals. And this year, we're trying to go twice as big. We've donated the first $20,000 and we'd like your help getting to our goal, $200,000, which would provide more than 2 million meals for families across the country. You just have to head over to dailystoic.com/feeding and together we can make a small dent in a big one. Big problem. We can't alleviate everyone's struggle or suffering, of course, but for the people we can help, the difference is huge. So let's do it. Let's be good Stoics

• 1:05:14Speaker 00

  today. Let's fulfill our obligation. Just go to dailystoic.com/feeding. Even $1 can provide as many as 10 meals. So head over to dailystoic.com/feeding to help us reach our goal of providing 2 million meals for families across the country.