Why Human Relationships are the Ultimate ROI

Summary

Podcast Summary: The GaryVee Audio Experience

Episode: Why Human Relationships are the Ultimate ROI
Date: June 2, 2026
Host: Gary Vaynerchuk
Guests: Sean, Sam

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Episode Overview

In this lively episode, Gary Vaynerchuk (GaryVee) sits down with Sean and Sam for a deeply insightful conversation on why human relationships are the greatest return on investment (ROI) in both life and business. The discussion weaves together Gary’s unique operational style, stories about building his team, practical business wisdom, and the power of intent-driven relationship building. Listeners get a rare inside look at how Gary structures his time, builds and scales companies, and leverages trust and EQ (emotional intelligence) as core assets. Expect candid reflections, memorable quotes, and a compelling case for the long game in business.

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Key Discussion Points & Insights

1. The Power of Relationships: Gary’s Approach

• Nick Dio's Role

  • Nick Dio is Gary’s "VP of Relationships," responsible for building and maintaining meaningful human connections worldwide on behalf of Gary.
  • "Nick just became another version of that, which is like, I can't be everywhere. Who's got a better job than Nick? Go around the world and listen carefully. If there's something we could do, something for someone, for karma, right? Like no KPI, no ROI." (Gary, [00:14], [05:06])

• Relationship-Driven Business Model

  • Gary admits his propensity for people led him to create an agency with 3,000 staff, even though it's "not the best business model" on paper.
  • Real business value is found in being helpful with no strings attached, which unexpectedly pays off in the long term.

• Scaling Connection

  • Hosting large group dinners through trusted proxies (like Nick) allows Gary to facilitate high-quality connections even without being physically present.
  • Sean describes being invited to a dinner hosted by Nick, not Gary, emphasizing the model’s effectiveness.
    • "It was at a very wealthy person’s home... and I'm like, 'Hey, where's Gary?' They're like, 'Oh, he’s not here. But I'm here. I'm Nick, and I'm hosting it on his behalf.'" (Sam, [07:37])

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2. Investing in People as Long-Term “Human Capital”

• The "LeBron James Spends on His Body" Analogy

  • Sean draws an analogy between Gary's investment in relationships and athletes spending on their bodies.
  • "What you're doing with Nick to me is the equivalent of LeBron James spends a million dollars a year on his body, is Gary spent probably at this point five million plus, ten million maybe, on just developing relationships." (Sean, [11:25])

• Counterintuitive Business Decisions

  • Gary admits to investing in actions that don’t make sense financially at the outset, but always played the long-term "marathon, not a sprint" game.
  • "Most things that are taught in business school are short sighted and are tactical versus how humanity actually works and business actually works… I am inherently a marathon runner." (Gary, [13:40])

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3. The ROI of Doing Good (Karma as Business Strategy)

• First Principles Thinking

  • "Doing good things for people is literally the highest ROI and lowest risk thing." (Gary, [12:17])
  • Most people mistake generosity for risk—a misconception Gary actively works against.

• Executing with Intuition and a High Trust Bar

  • Gary trusts his gut and the intent of others, relying on years of personal and professional observation.
  • "I trust (Nick) to represent me to some degree because I can’t be everywhere." (Gary, [05:06])

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4. Systems, Tech, and Scale—How Gary Stays Connected

• How Gary Uses AI and Tools

  • Leveraging AI/CRM tools like OpenClaw and platforms like Granola to capture relationship data, reminders, and context even in fleeting moments.
  • "Mainly for CRM for me right now. Relationship graph... Once it understands my relationship graph, now I'm just building, you know, logic and agents on top of it to like keep me updated." (Gary, [03:03])

• The 15-Minute Meeting Standard

  • Gary now compresses meetings to 15 minutes for maximum efficiency, maximizing focus and throughput.
  • "Everyone's meetings are twice as long as they need to be if they're a winner and they know it." (Gary, [36:05])

• Context-Switching and Emotional Management

  • On handling non-stop, high-stakes decision-making with minimal downtime:
    • "The number one thing... new admin and every single new person that films me says with like to a T is they do not understand the switching that I. And I talk about something that never even crossed my mind until the last five years." (Gary, [38:21])

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5. Company Scaling and Team Building

• Building Through Family-Like Loyalty

  • Gary attributes his ability to scale to finding and mentoring high-quality people who become like family, some over a decade-long timeline.
  • "The real reason is because of the 50 people... and it's somebody who's worked for me for 11 years who's going to be my co-founder." (Gary, [29:47])

• Turning D-Players to B-Players

  • Investing time and coaching in people others overlook is a key part of Gary's operating philosophy.
  • "I just had this feeling that my superpower was the human relationship side... that I could convert D’s into B’s and C’s into B’s." (Gary, [29:47])

• Candor as a Learned Leadership Skill

  • Gary’s book 12 and a Half chronicles his struggle with firing and being too nice—a vulnerability he’s since converted into a strength ("kind candor").
  • "I used to think my greatest strength was eliminating fear. I had superhero syndrome... I realized I thought everybody was rolling with me with lack of fear, but that many... were scared because they didn't know where they stood with me because I was unable to do candor." (Gary, [17:14])
  • "My candor was at a zero. I rebranded... into kind Candor." (Gary, [21:18])

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6. Human Compounding, Not Transactional ROI

• “Rainy Day Human Stuff”

  • Gary distinguishes between greed for deals and “rainy day human” equity—doing for others so that, in a life crisis, massive goodwill circles back.
  • "I do everything I’m doing not to get into a deal in nine years... but for rainy day human stuff... you have unlimited equity in the universe that everyone rallies like the fucking Avengers." (Gary, [15:21])

• Long-Term Greed vs. Short-Term Greed

  • "It’s just the difference between short term greedy and long term greedy. When it’s long term greedy, you’re going to play a totally different game." (Sean quoting Alexis Ohanian, [14:14])

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7. Building and Juggling Multiple Companies

• Gary's Current Companies (as of 2026):

  1. VaynerMedia / VaynerX: $400M+ revenue, full CEO oversight ([26:00])
  2. VaynerSports: Sports representation with hundreds of athletes
  3. VCR Group: Restaurant group (e.g., Fly Fish Club, Capon's Chop House)
  4. VeeFriends: Licensing/collectibles/brand building, aiming for “Marvel/Pokemon” status
  5. Wine Library: Ongoing involvement in family wine business
  6. VaynerWatt: Under-the-radar, rapidly growing TV production company
  7. The Gary Vee Personal Brand: Books, speaking, content, large NIL/team
  • "I have seven active businesses that are doing more than eight figures a year in revenue where I am meaningfully involved." (Gary, [25:58])

• Time Management & Structure

  • Gary describes highly efficient days: 8:30/9am starts, continuous meetings, family prioritization, extreme context switching.
  • "Every minute's booked. 60% of the meetings are 15 minutes... My secret weapon was hiring people. I just had this intuit that I was gonna be able to have a lot of really good A and B players around me that would stay with me." (Gary, [29:47])

• Decision-Making Breakdown

  • "I would say 30% I'm being informed. 70% I'm making decisions." (Gary, [38:10])

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8. Wisdom, Learning, and Personal Development

• Learning from Others

  • Gary admits he gets most of his learning from people (especially his mother) and osmosis, not books or traditional study.
  • "My mother's by far Number one... almost the far majority of what I do is predicated on the people and emotional intelligence front more than information." (Gary, [23:23])

• On Being Selective About Associations

  • Maintaining reputation by being careful who he’s publicly associated with, wary of scammers or those with questionable ethics.
  • "I, you know, you're smart and so I know that question is grounded in, you know, that I've avoided a lot of stuff and association and that's the reason." (Gary, [52:03])

• On Coping With Envy and Mimetic Rivalry

  • Discussed the phenomenon where even big winners focus on comparative envy.
  • "I literally believe the far majority of people get to the top from extreme insecurity." (Gary, [57:42])

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9. Notable Quotes & Memorable Moments

• “Doing good things for people is literally the highest ROI and lowest risk thing.” (Gary, [12:17])
• “I am inherently a marathon runner. So I train for marathons in a world where most of my contemporaries... are sprinters.” (Gary, [13:40])
• "The 15 minute meeting has been gangster for me. Game changing for me. I do think I’m getting three days of work in one day for sure." (Gary, [37:25])
• "You can be so much more efficient if you have remarkable people around you and you're obsessed with not wasting time to fill the slot." (Gary, [37:27])
• "I probably do everything I'm doing... for some reason Sam's nephew can help her. Right? Like... you have unlimited equity in the universe that everyone rallies like the fucking Avengers." (Gary, [15:21])
• “I'm comfortable. I'm very comfortable. And this is a theme of this whole interview… I'm very comfortable dying on my sword, which is my intuition.” (Gary, [43:32])

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Timestamps of Notable Segments

• VP of Relationships / Nick Dio Model: [00:07], [05:06]
• Gary’s Tech Organization Tools: [03:03]
• Analogy of 'LeBron spending on his body': [11:25]
• ROI of doing good for people as core business thesis: [12:17]
• Candor and firing struggle: [17:14], [21:18]
• Breakdown of Gary’s 7+ Businesses: [25:58]
• Time/Meeting Efficiency: [36:05], [37:25]
• Decision vs. Info Split: [38:10]
• Handling Envy & Mimetic Rivalry: [54:39] onward
• Coping with context-switching & emotional adversity: [38:21] – [41:21]
• Being Selective With Who You Associate With: [51:17] – [52:44]
• Restaurant model and scaling: [59:36] – [62:44]

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Tone and Style

Gary is candid, high-energy, often humorous, and never shy about mixing tactical advice with philosophy. There are many stories, real-life business examples, and practical takeaways. He’s open about past failings (e.g. his struggle with candor and firing) and how he’s worked to correct them.

Sam and Sean provide curiosity and banter, bringing out stories and new angles from Gary. They share relatable business anecdotes and aren't afraid to put Gary on the spot in a friendly, probing way.

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Final Takeaways

• Relationships, not transactions, create the deepest and most durable ROI—personally, professionally, and even financially.
• Intentionally developing, maintaining, and investing in great people pays off in ways that spreadsheets cannot measure.
• Efficiency comes from trust, team, and true prioritization—not just tech or hustle.
• Long-game mentality, emotional intelligence, and intuition are as important as strategy or capital for enduring success.

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For listeners: If building a long-lasting, trustworthy, and deeply connected business life matters to you, this episode of The GaryVee Audio Experience is an absolute must—packed with actionable wisdom, real examples, and the kind of candor only Gary delivers.

Transcript

[Sean]

You have this guy, Nick Dio. He's like host these dinners almost like on behalf of Gary. Who is this guy? What is he doing?

[Gary Vee]

So I'll, I'll tell everybody who's listening. Nick Dio is the VP of relationships. He literally goes around the world. And in essence, he's been with me for 12 years. Started as an intern, grew up in Vaynermedia. I trust him to represent me to some degree because I can't be everywhere. And about two, three years ago, I realized my favorite thing about business is people. It's probably why I ended up having an agency with 3,000 people when that's not the best business model. It's why I make so much content. I just like the people part. And Nick just became another version of that, which is like, I can't be everywhere. Who's got a better job than Nick? Go around the world and listen carefully. If there's something we could do, something for someone, for karma, right? Like no KPI, no roi. And Nick, you know me so well. You, you, you know, we have so much to give. Just keep your ear to the ground, you know, figure out who's got the right intent. Figure out who's talking shit and not talking shit. Like who's good. This is the GaryVee audio experience.

[Sam]

Gary, let me ask you a hard hitting question. I've known you now for a few years. A while now.

[Gary Vee]

Yes.

[Sam]

Do you own a computer?

[Gary Vee]

You know what's funny? I did not own a computer. I'm on a computer right now. I did not own a computer for four or five years. It going into Covid.

[Sam]

So what, what year did you buy your first laptop?

[Gary Vee]

Oh, I bought my first. I mean, I had a computer.

[Sam]

I'm sorry, what, what year did you, do you regularly use a laptop?

[Gary Vee]

I went full phone because I didn't work within Excel or any documentation. And it was all email, meetings, social. So I, I think I stopped having a laptop in 15, went to 19 without one. But I've had one since.

[Sean]

We had those, you know, those luxury brands where it's like quiet wealth or whatever, where there's no label. We've, we found the podcast version of this, which is that the richest guys who come on the pod, they don't know how to use a computer. They're like, assistant sets up a screen, they just show up. We had one guy try to share his screen and he was like, honestly, he's like, honestly, guys, this is, this is bad. I don't know what, I don't even know what I'm doing. We go just click in Chrome because what's Chrome? He didn't even know. I don't think I have one of those.

[Gary Vee]

It's ironic. I would actually argue, you know, it's so crazy to think of evolution. So I went through those four years. It was the best. Like not having a laptop at the airport, like it was the best. And now it's completely the opposite. Right. Like my open claw computer is like the most important thing in my life. Right. It's just so fascinating.

[Sam]

Well, that's what one of the reasons I was asking you that was. I thought you weren't a computer guy. We had Mark Laurie on, who I think is a multibillionaire and that was the first time Sean and I learned about this where he, he didn't use a laptop and we were. It was funny. He's like, I actually only use my phone, but I've never seen.

[Sean]

What are you doing with OpenCloud, Gary? What's.

[Sam]

And that's. I was gonna ask you what are you doing like on. With AI on a regular basis now?

[Gary Vee]

I mean lots of things. I think with openclaw specifically I'm using it as a capture all for all information. What's been really fascinating, even with three admins and chief of staff staff and all this, I'm still like, I never got there. Like some of my friends where their chief of staff is with them in every meeting. So there's so much loss, you know, I'm not a note taker back to the whole entrepreneur of it all. So there'd be like so much context lost, right. Like in a meeting, so much opportunity missed. So one of the first things I've done with OpenClaw is it might even happen here. I might literally take a photo of this screen and be like talk to these guys. And we got it like, and then so it's a photo sent to my OpenClaw on text and then a voice note saying me and the boys were talking about China. Make sure I do like it's just basically a capture all. It's mainly for CRM for me right now. Relationship graph. And then what's so amazing right is once it understands my relationship graph, now I'm just building, you know, logic and agents on top of it to like keep me updated on when things are happening. Like even sending you guys email automatically in 2 years saying congrats on a trillion downloads because it knows I know you knows that was a milestone for you and I do want to, you know, say what's hey, good job. You know, like. Like, it's just, like, relation. It's scaling. All my favorite things about humans is definitely step one for me.

[Sam]

Are you recording this in granola or. Or what are you. What are you recording this in?

[Gary Vee]

I'm. I. Granola is what I tend to use. I'm just. I'm actually not doing it right now for some reason.

[Sean]

You. You just said something about relationships, and you have this guy, Nick Dio.

[Gary Vee]

Yes.

[Sean]

I think you. I don't know if he's still with you, but this fascinated me. Somebody told me, I don't know the exact model, but they said, you got to ask him about Nick because he does these really interesting things. He's, like, host these dinners. Almost like it was me of Gary. Like. Like, it's like, Gary wants you to

[Gary Vee]

come to dinner photo. It was Sam brought up to you. Because now I remember Nick bringing up. Yeah, I mean, my.

[Sean]

Who is this guy? What is he doing?

[Gary Vee]

And this is. So. I'll tell everybody who's listening. This is actually a pretty. This will be good. This is gonna be good for your crew. I think at some point, as all of us go through it, you start to every day, and I'm sure you guys are feeling this. You're a generation behind me, and then a lot of the kids that are listening, every kind of, like, five, 10 years, you get wiser, you get more thoughtful, you learn things, and, you know, you start to understand more and more why you're doing things right. Like, for example, I'm going to deviate. That's what I like to do. I feel like at some point, I was like, oh, I. I got to the quote unquote top because I was over loved. It was good. It was, like, good fuel. And I have a feeling I'll be able to stick around because I started seeing so many people get to the top out of bad fuel, extreme insecurity because of what their parents did wrong or childhood, and they're going to fucking show it to everyone. And they're like, you know, that was a big aha moment. In my early 40s about two, three years ago, I realized why Nick Dio exists. So for everyone. Nick Dio is the VP of relationships. He literally goes around the world, and in essence, he's been with me for 12 years. Started as an intern, grew up in Vaynermedia. I trust him to represent me to some degree because I can't be everywhere. And about two, three years ago, I realized my favorite thing about business is people. It's probably Why I ended up having an agency with 3,000 people when that's not the best business model. It's why I make so much content. It's. You know, you guys have gotten to know me a little. Like, you guys know like, the. Like, some of the subtle differences of how I roll, then, like, let's say, like, people that tend to look like me. Like, I just like the people part. And Nick just became another version of that, which is like, I can't be everywhere, and I. And who's got a better job than Nick? Go around the world and literally go. And by the way, when he goes around the world, it's go to cool places and cool. And listen carefully. If there's something we could do, something for someone, for karma, right? Like, no kbi, no roi, Like. Like, pay attention. And Nick, you know me so well. You know, we have so much to give. Just keep your ear to the ground. Here's where he does a great job. Figure out who's fucking full of shit and who's a good person, you know? Figure out who's got the right intent. Figure out who's talking shit and not talking shit. Like, who's good? Who's good?

[Sam]

Well, let me tell you what it was like from my perspective. I got a DM from you, and I don't think I. You could have said it. And there's a chance. I didn't read it closely, but it said, like, hey, I'm going to be in Austin. Do you want to get dinner? Yes. Yeah, I just said yes. And then I just got sent an invite. And the invite, like, I said it could have said the details, but I show up and it's like 50 people. It was at a very wealthy person's home. This, like, Microsoft executive's home. And I'm like, hey, where's Gary? They're like, oh, he. He's not here. But I'm here. I'm Nick, and I'm hosting it on his behalf. And I met.

[Gary Vee]

Like, yours was. Yours was. Felt like more of a robotope.

[Sean]

Yeah.

[Sam]

No, but I want to give you credit. I don't think I read it. There's a chance I didn't read it, but I get there, and I met like this.

[Gary Vee]

I remember that party because I was one of the bigger ones. It was never alluded. Like, I apologize if we didn't word it well, but I remember the context. Like, we weren't trying to trick you to meet.

[Sam]

No, I don't think so. And I bet, like, I bet this cool dude named Hunter do you know Hunter? I think his name's Woodall. He's got one leg and he, like, won in the Paralympics. He was badass. I met like all these, like, it was like this athlete, this Microsoft executive, this person, this person. I met all these cool guys. It was awesome.

[Sean]

Which is the easiest way, by the way, to spread good karma and good. And like, you know, add value is just, hey, let me just connect you with 10 other awesome people versus what can I do for you? Right? That's the easiest way to do it.

[Gary Vee]

Yeah, that is one. And it was early in Nick's world where I wanted him to get a broader understanding of different people that were in the. What's tough about things for busy people that like relationships is you just can't scale. You're a human, right? And so I end up with these unlimited business acquaintances that I wish I could take to the next step. And Nick helps me scale that a little bit by decoding a little bit because I trust his intuition. He's been with me a long time, grew up with me, and he represents me well and he's smart and I trust him. So then when he hits me and says, hey, you know, this person really needs a new marketing person. Like, this is how I don't think I'll ever. When I'm long gone, I think good stories will come out. Like, this is a true example. And, hey, this kid's got a good DTC brand. It's gone from 0 to 20 million. We're not an investor in the company. I have no vested interest. They just lost their head of marketing. He was like, over dinner, talking in a group of 12, like, he's stressed and worried. And then three weeks earlier, one of my best people at Vayner came to me after eight years and said, I don't wanna do agency anymore. And literally just putting that person in that company and everyone wins. And literally, I don't have a dollar in the company. Literally, literally nothing. Literally no transaction. And like, we do that in a way that I. I now do feel three. Like, in the last three years, people are starting to understand Gary and Gary Vee a little more. Like. Cause we're doing it at such scale that eventually the truth becomes your actual reputation.

[Sam]

How do you.

[Sean]

Sorry, Sam. I just gotta say one thing on this, because I think on the surface it's like, okay, great. So this guy hosts dinners. That's cool. Sounds like he's. He's got a mandate to spread good karma and just help people. That's cool. I think this is actually unbelievable. I can't believe you don't talk about this more. This is like, you know, when that story came out a few years ago where it said LeBron James spends $1 million a year on his body and people went nuts and this went everywhere. This is like a global thing. Other athletes turned onto this. And I was, I was thinking about it the other way. I was like, first of all, Obviously this guy's $1 billion athlete. For him to spend $1 million a year on his body, that's like a masseuse, a trainer, good, a chef. And there's nothing. He should be spending three or four times that if you, if anything. Second is what a great question everybody should ask themselves. Who wants to be great is what is your equivalent of spending a million dollars a year on your body? And you know, my executive coach, for example, he spent a million dollars getting coaching himself from the best in different disciplines. He would overpay and say, how do I get, how do I go do an immersion with you? I know you usually do once a week, but I want to do immersion because he's like, I want to be the best coach. So I'm going to go learn all the modalities from the best teachers of those modalities. And I just think everybody should ask us. And what you're doing with Nick, to me is the equivalent of LeBron James spends a million dollars a year on his body, is Gary spends. Gary spent probably at this point five million plus ten million maybe on, on just developing relationships with people who he thinks are doing good things in the world. He wants win in their sales.

[Gary Vee]

I have three full time employees at Vayner X who host influencers that are emerging to walk through the office and, and meet brand deal teams to maybe get them brand deals on pure karma.

[Sean]

Yeah, see, that's amazing. And I think that that that type of investment only comes from first principles.

[Gary Vee]

Doing good things for people is literally the highest ROI and lowest risk thing. And most people think it's the highest risk thing because when they're doing something good, they're not doing something good. They're doing something calculated with the, with the expectation or at least minimumly the hope that something comes back to them.

[Sam]

Well, but on the other side of that, it could be like, well, I need to, I'm spending money on these things. I have bills to pay. I, I, I, So that's Sam, to

[Gary Vee]

your point, I didn't do this the first 30 years of my career. Like I got to a place where I could afford Investing in that.

[Sam]

Yeah, but what I was gonna ask you is I think that you've always, you, from what I could tell, you've always defaulted to hiring a lot of people. I think that, like, that, it seems like that's kind of been your, your, your, your how you like to operate. And also you've defaulted to doing things that don't really make sense on paper. But because you're you, it does appear as though it works out nicely in terms of profit, not. It also works out and you're happy about it. How do you like justify doing some of these things that don't make any sense financially, knowing that like when VaynerMedia was 5 or 10 years old and your margins were a bit tighter and you didn't have enough money to go around to do some of these wacky things, and yet it still appears as though you did do them.

[Gary Vee]

You're absolutely right. I did. It's a really good observation. I think the very simplest, clean. You know, this is now me respecting the audience because I think you have a sharp one. It's because I think most things that are taught in business school are short sighted and are tactical versus how humanity actually works and business actually works. Like if you're. And then I would also say that I am inherently a marathon runner. So I train for marathons in a world where most of my contemporaries on paper are sprinters and they train for sprinting and that's appropriate for them.

[Sean]

Alexis Ohanian was at one of our events and he checked me in the best way possible. We were talking about how, yeah, we wanted to get this great group together. You know, we don't charge anything. I pay for this whole event out of pocket. I pay like a quarter million dollars a year just to host this event. And it's like, look, I asked nothing in return, which is all about, you know, just having a really. And everybody's like this, we're all like a generous crew. And he goes, no, no, no, that's not it. And I was like, oh shit, what is he, what is he about to say? And he goes, he goes, it's just the difference between short term greedy and long term greedy. He goes, you know, he was in the first YC batch. And he goes, one of the beautiful things about Silicon Valley is you learn the virtue of long term, long term greedy people. And he goes, it's not a bad thing. It's. Everybody obviously wants their interest, but when it's long term greedy, you're going to play a totally different game than short term greedy.

[Gary Vee]

And then I would. That's exactly right. And I would tell you my nuance that I do see in some others, which is why I gravitate towards them, is. And then if you're greedy is about rainy day human stuff, not money in your bank, it becomes an extreme nuance of that. So let's.

[Sean]

What's rainy day human stuff? What does that mean?

[Gary Vee]

I probably do everything I'm doing not to get into a deal in nine years and put a million and make 40 million more for my daughter has an issue in 19 years in her personal life and for some reason Sam's nephew can help her. Right? Like I'm good enough to take care of my money part. I'm thinking like, like fuck man, your mom has a rare form of cancer and you have unlimited equity in the universe that everyone rallies like the fucking Avengers and helps you. Do you hear that? Sounds like breakfast is ready because Quaker's coming in hot with morning nutrition 100% whole grain oats and a good source of fiber to fuel the rhythm them of your morning and kickstart your day. And that sounds absolutely delicious. Fuel to start whatever's next. Quaker, official sponsor of FIFA World Cup 26. Let's go.

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[Sam]

I Sometimes it's hard to run a business that way. Being nice all the time because you have to make difficult decisions like firing someone if they suck. But you seem like you are a really bad firer. Do you give people lots of opportunity? Would you. Is that one of your weaknesses you think is like being overly generous?

[Gary Vee]

I literally wrote a book because I was so bad at it I hit it. But it was called 12 and a half and it was a 13 leadership principle type book from my perspective at that point in my career. And in the book, the thirteenth principle was a half and it was called Candor. And I spoke about my journey and I was only ready, Sam, to write about it. You know, you can only talk about your alcoholism when you're like feeling like you're close to fixing it, right? Like, and by the way, back to like alcoholism or what I was dealing with, which was you're. You're incredibly wrong. Sam. I wasn't a bad firer. I was an all time atrocious firer, right? And I didn't see it. Right? All of us currently, the three of us, and we're proud of ourselves in certain areas and know we can do, but currently, by far the biggest problem the three of us have is something we can't see. Right? And so I, I used to think of it as my ultimate strength as Sam. And it had so many beautiful effects, it led to so much good, but it actually ended up leading to the worst of the worst. Meaning in my 20s, you know, I've been really managing people since I was 18 years old, right? With the liquor store for real. Like, truly, like this 18 year old child is the boss, you know, because he's the boss's son in this liquor store and all the way up to where I am now. And so I used to think my greatest strength was eliminating fear. I had superhero syndrome, right? Like I can take care of everything. I got it. Like, and like, you know, come along and da, da, da. And I had this day in my early 40s, which led me to writing the book where I realized I thought everybody was rolling with me with lack of fear, but that many of my company were scared because they didn't know where they stood with me because I was unable to do candor. And on Friday I was like, sammy, fucking have the best weekend, my guy. Like, have, like, really? I think you guys know me. I'm a little go lucky that way. I'm like, sammy, have the best fucking weekend this weekend, right? And you're working for me for three years. Like, all right, Gary, like you too. And then like Monday, I'd be like, Sam, you talk to you in the office real quick. Hey, so you know it's gonna be your last day. And by the way, I've been sitting on this for a year and a half, right? Right. And today's your last day. And you're like, what the bro? Like, I like, you've never said anything like. And then I would blame you. I'd be like, sam, you're, you're so delude. Like, could you. Then I would talk to Sean and be like, sean, could you believe Sam? Like, everyone in the company knows Sam sucked for the last 18 months. I was giving him a gift for the last year of charity, and he's mad at me. I was coming up with that excuse. So my candor was at a zero. I rebranded. So I have this real watershed moment where a group of former vayner employees, like, were in a Facebook group, like, not talking nicely about me. And these were people I really had a lot of continue ironically, like, you know, it's funny, that person also, over time, realizes what they did. So there was like a lot of them I've reconciled with in a great way. But it was really hurtful. But I knew I had to be accountable. I'm like, why are these people, who are all lovely people, who I really went to bat for, did a lot of great things for, who have really nice careers on the equity of their time with me, why are they shitting on me? And it was all. And I knew it because I just looked at the eight names and I was like, these were all sloppy exits, all of them. Hey, everybody, hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. They'll make my mom super happy.

[Sam]

You know what's funny is, have you guys heard of. Obviously you have, but Jensen Hung, the Nvidia guy, he has this great line where he's like, I'm not going to fire you. I'm going to squeeze you so hard that greatness comes out of you. And then interestingly, Dave Portnoy, the founder of Barstool, he had another point where he goes, I never fire anyone. I refuse to fire anyone, but we are going to make you great. Like, he said something like that. And I thought that was so fascinating because that's the exact opposite of what I think. You know, we had Neil Patel on and, and Neil was like, I only hire people who have been there, done that. I only hire people who have built this thing already that I want built. And if they can't do it, then I fire them within a week. Which is probably honestly the more common attribute of like, just hiring people who have been there, done that. And then if they suck right away, you know, you hear, hire slow, hire fast.

[Gary Vee]

I. I bleed into both those categories, by the way, and then have a third element, which is I'm the cliche girl that wants to date the bad boy because I'm going to fix him, right? So I have bled my. If I didn't have entrepreneurial DNA, I would 100% be a therapist, guidance counselor, or a coach, right? Like, and so I allowed both in my investing and in my operating too much in my 20s through mid-40s, too much of my nonprofit therapy DNA into my day to day, I've been able to clean it up in the last five years. And let me say this to anyone who's struggling with being too nice, you know, or. Cause it was never that I was scared to not be liked. It was that I thought I could fix it, that I would squeeze it, that I would make it, but through love, not like fucking trashing you, like what you know. And so for anyone who's struggling with this, like, there's a better way. Let me say it this way. As long as you're delivering things with candor, all of it becomes dramatically more palpable. I was not. I was holding it all in. That became the vulnerability. And I'm really glad as I've gotten to 50, I'm now in that place where I could be a lot better. And it's showed up in the business results. I've been a dramatically better CEO the last three, four years where I've cleaned up my candor. I rebranded it into kind Candor. It became the ethos of our company because I think candor a lot of times is used as an excuse to be a dick face and suppress people. And so we had to put that word kind in front of it. And it's. It's worked for me and for my leadership, and it's been a big step forward in my career.

[Sean]

Let me ask you this. You give a lot of coaching and advice to entrepreneurs around the world. Who, who do you learn from? So who you. Who do you call for advice? Who's a key? Who do you. Who do you steal from? You like, oh, man, I love the way this person. I'm gonna take a piece of that to my game. I'm sure you're always learning. I'm not saying that, but I'm looking for like maybe a couple of people or blueprints.

[Gary Vee]

I've never been great at people. I was a terrible. Clearly had some reading comprehension. The reason I was a poor student now in hindsight is my reading comprehension is non existent. Right. So I learned through osmosis. I learned through audio and video, but I learned the most through inhuman. Right. Like, one of the things I struggle with, with the hybrid and work from home thing is I know there's half the world that learns the way I do. And if you're not learning through osmosis, which is so much easier in a physical environment than it is on a screen through zoom, you'd be vulnerable. Like, I would have really struggled to learn a company if I was an employee through the, you know, the documentation. Right. So I learned from my mother's by far Number one by a country mile. Because almost the far majority of what I do is predicated on the people and emotional intelligence front more than the information I learned through social media at scale, right? Just like just consuming content at scale from random people that are farming carrots in Idaho to someone going deep cut on what they're doing with Claude code to pontificate. And it's truly like I am a product of this era.

[Sam]

Like, whose video are you. Are you turning the sound on lately? You know, when you're scrolling Instagram?

[Gary Vee]

Honestly, like I, you know, I'm pissed right now because I want. My favorite thing is to give flowers. And the truth is, it's so weird. Sam. Like my brother for example, would answer this epic. He's got his fucking ex so dialed in and he would sit here and talk about AI or live shop. Like he would give you like seven names and he'd be like, shout out to Matt Van Horn. You know Matt Van Horn's a. Matt Van Horn's been vibe. Like he, he would be so good. And I'm so shitty. Because the answer is as soon as you asked it, I'm like, fuck. Because I hate this question because for some reason it's so blurry to me. Meaning like I don't even know, right? It's like, it's like, it's just like information. Like, like people follow the 5 to 12 best voices very well and I'm like the beneficiary of this. On the other side, a lot of people follow what they want from me on it. My learning is happening and not even consuming the content. It's like being in the meetings, don't forget. What's weird about me is I'm in the traffic of my businesses, right? So here's something interesting, by the way, men, Back to the LeBron James million dollar thing. I have seven active businesses that are doing more than eight figures a year in revenue where I am meaningfully involved.

[Sam]

Which ones?

[Sean]

Tell us about it. What do we got?

[Gary Vee]

Break them down. VaynerMedia, Vayner X, which is 400 million in revenue. I am the day to day CEO.

[Sam]

And that owns all the other six?

[Gary Vee]

No, it owns, it owns none of the other six. Next. Vayner Sports. You know, I took three recruiting calls yesterday with my brother.

[Sean]

Like, what's Vayner Sports doing exactly?

[Gary Vee]

Oh, Vayner Sports does sports representation. So we replace Kirk Cousins, Sauce Gardner, Aidan Hutchinson, Bo Bashette and I also

[Sean]

have to now or just pros and

[Gary Vee]

I at scale we have probably 300 college athletes.

[Sam]

So that's doing tens of millions.

[Gary Vee]

That's doing tens of millions in revenue. I have CR Group, which is a restaurant group, which is, if you remember, famously, I had that NFT restaurant news alert, everyone. It's crushing. It's called Fly Fish Club. We also have capons and ito and five restaurants in. And I'm actively involved texting with David Rodolitz all the time. So VCR Group, tens of millions in revenue as a restaurant group. I have veefriends. Veefriends is probably the thing I'm most like. AJ and David Rodelitz are 1A in the prior two businesses. I am 1A in Veefriends. Veefriends is gonna do minimally 20 million in revenue this year in licensing and selling comic books and coins and trading cards. I'm building a true brand, by the way. That is a dark horse chance to be really one of my greatest roses. Because all the ashes of the NFT era, that I'm gonna get to the other side and be Marvel and Pokemon is gonna fuck with everyone. So heavy in 15 years. Wine Library people will be flabbergasted how involved I still am in the wine business. My best friend runs it. I am definitely 1B to my dad and Brandon's 1A, but I work on it every single day. One that's really under the radar. Vayner Watt. I have a very successful TV production company that's kind of brewing right now called Vayner Watt. We have a bunch of shows that have quietly just sold. So you like literally on Hulu and ABC and Netflix, like you're gonna see Vayner Watt, Vayner Watt pop up and then finally, and I'm sure not lost on you guys, the nil and brand of Gary Vee. I have a full massive team on it. You know, it's a real part of my life speaking in books and content

[Sam]

and do you have ads or just. Or is it monetized via speaking?

[Gary Vee]

I did a deal with Standstill. I did a deal with Masterclass. I'm starting to let. I'm starting to be open to Gary Vee. I don't do like a brand deal. I'll look at seven and eight figure nil deals where it's really integrated. Potentially me doing a little consulting as well. But I think you guys are probably. I'm writing a new book called the Individual Empire, which talks about the me, the Bartletts, the Alex Coopers, the rise of the creator entrepreneur and the entrepreneur creator as the next Fortune 500 companies. And my belief with AI blockchain evolving social decentralization of Hollywood and Madison Avenue and Wall street, that the biggest companies in the world are human based organizations where the human either has a partner that could operate or they're a me where they can be both. So that's how I look at that world.

[Sean]

You just, you just named.

[Gary Vee]

I'm sorry, what?

[Sean]

Oh, sorry. You just named like six or seven companies that are doing eight figures that you're like, I'm either the 1A or the 1B. And I think that's awesome because I too Wish I had 96 hours a day. And so, you know, walk us through what's. What does the day look like? What's the time blocking look like for this? Right? Like, you know, Elon is like, I spend three days here at SpaceX, three days at Tesla, then Saturday, Sundays I work and I work till 2am every day. Like, what is this? What's a day in the life of Gary Vee to do all this?

[Gary Vee]

You know, I wake up at 6 or 7. There's a workout session every day. Ish. I've actually been a little bit sporadic lately. I'm pretty much an 8 to 8:30 to 8 to 9am Star point done between 8 and 10pm, depending on the day. But there's not a single break. No lunch, no anything. Every minute's booked. 60% of the meetings are 15 minutes. And again, let's get to the point here, right? Let's get to the point here. This is 30 years of building equity. And Sam said something interesting. My secret weapon was hiring people. And again, you guys, again, this is fun talking to you. Then let's say a net new podcast where I've interacted a little bit with you guys. I had this feeling, which is truly, this has been a good prediction of mine. I had this feeling that I was gonna be able to have a lot of really good A and B players around me that would stay with me, that could do bigger things, could do things on their own, but that the relationship and that they would believe in me. And then they would say, you know, in 15 years I might actually make more money being Gary's number 13 versus me, my own number. I just had this intuit and that I could convert D's into B's and C's into B's. I just had this feeling that my superpower was the human relationship side. And so the reason I can do this. So yes, I work a lot and yes, I'm uncomfortably efficient with my time and yes, I'm on a boat which has seven holes. And I put my finger in the one that needs it most for every parent that knows you're only as happy as your most unhappy. And so my ebbs and flows of like, oh shit, vaynersports needs me or shit, Vayner, like there's all that. But the real reason is because of the 50 people from Ryan Harwood or Kalyn or Claude or JT or AJ and Greg Gensky or David Rodolitz and Connor Hamlet or Andy Kay and John and jt, John Troutman and May and Rips on Vee Friends or Brandon Warnecke on Wine Library or Eric Wattenberg Baynor Watt on that. And I've got another one coming that I'll announce next year, standalone business. And it's somebody who's worked for me for 11 years who's gonna be my co founder. And I had the experience with Resy, you know, like people forget that I'm the co founder and inventor of Resy, but I had Ben LEVENTHAL Be the one A, I was the one B, and that was a hefty nine figure exit. And I had Empathy Wines, two former interns of mine who worked for me for 11 years. And we started Empathy Wines and in 18 months sold it for a almost nine figure, hefty eight figure deal to Constellation Brands in 18 months. Just like, you know, everyone's like, gruins. I'm like, I did that not, not to 1.2 billion, but to, you know, you know, you know. And so blah, blah, blah, blah. It's because when I do things on a net new business, the person is my family member. It's family business. We know everything about each other. It's seven to 10 years before we decided to do X, Y and Z. They roll differently than a lot of people trying it with net new people. They hire randomly.

[Sam]

I was listening to. Go ahead. Well, I was listening to your podcast this morning and someone asked a question that a lot of content, content creators ask. They said, I'm doing live shopping and live streaming, but I don't want to do this all the time. And I'm nervous that this all relies on me and I want to get other content creators. You have listed six or seven businesses doing tens of millions in revenue. Presumably you were getting close to a billion. You're doing many hundreds at least in revenue. And it all is started off of you. And I don't know what percent is run or you get customers still for each thing because of you. But a lot of it's Based on you and your content. Do you get nervous about that or do you not care? You think I just love this so much that I ain't going anywhere.

[Gary Vee]

Not only do I not love it, not only is that true, Sam, I think I'm the preview, not the anomaly.

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[Gary Vee]

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[Sean]

So you think there's a. You're like, this is a model that works.

[Gary Vee]

This is what's going to happen. Yeah, this is what is happening. If you look at the derivatives of all the people that are like kind of that crew right now, what do you think is happening? And then of course there's Kylie Jenner and Hailey Bieber where they need a business person to also be in round but then there's also like, I mean you guys are like in pot. You know, everyone has different hopes and dreams and Sam, you've nailed it. Like to me like I love this shit, bro. You know, people go and buy a home in the Bahamas and that's and play golf and that in Baker's Bay and that's their escapism when they need an escape. People have skiing. People have so many and sometimes unfortunately they have bad things like drugs and people need escapism. You're just going when I need a break from Vayner X which I do a lot because client services suck. Shit. I don't go to Aspen. I go to two days off sites for vee friends because it fucking fills my soul and I do the comic stories of my characters, you know. Or I go to a half day at wine library and talk to Brandon because he's my best friend since I was 14 and I need it for my soul. But then we also Fix the fucking business. Or I go on a six hour flight and ask AJ to come with me because I need him because he's my brother and I just need that good energy because I'm fucking frustrated. What's going on with Vee friends or wine library and we fix wiener sports. You know what I mean?

[Sean]

What's going on in these 15 minute meetings? Because I suspect what you're doing in 15 minutes is taking most people an hour. So maybe you have a format.

[Gary Vee]

Maybe I'm mad at you. Bro, you took my. I was asked that. I was about to say the thing that everyone else is spending an hour on. Bro. This is going to be one of the highlights that I know from this meeting, this podcast everyone's going to. I love that I said meeting. This feels more like a business meeting than this is why you guys are so successful. Everyone's going to say yes right now. On the treadmill, walking the dog in their car, on a plane, or however they're consuming this. Everyone's meetings are twice as long as they need to be if they're a winner and they know it.

[Sean]

You got slam poetry snaps for me.

[Gary Vee]

And I just went there. I knew it subconsciously. Then it became just, you know, then years went on and it became conscious and then I executed. I've been in that. And I would say a lot of what has led to these. This, you know, I have this huge pride of how underrated as a businessman I am. Because what I just dropped on you guys, literally nobody really knows. Which is wild, because I'm Gary Vee and I'm talking all the time. And I think I got there on the 15 minute meeting and the family business vibes of my partners in crimes and the top. And by the way, it's not just one person. Like every company requires three or four family members for it to really work the way it works for me. Because you gotta have a backup and a backup and a backup. Cause there's so many variables that can go into these things. So the 15 minute meeting has been gangster for me. Game changing for me. I do think I'm getting three days of work in one day for sure.

[Sam]

And what percentage of.

[Gary Vee]

I'm sorry, Sam. I want to say this. This is all happening at a time where I'm spending more, I mean, more time with my family than ever. You know, I have teenage kids, I have a wife. You know, I got remarried a year ago. Like, I'm like way, you know, I kind of went with the generic, but there's so much More slicing and dicing that I'm accustomed. My son is all in on AAU basketball, is eating up all sorts of time. You know, my daughter is going to go to college in a couple of years, so I'm milking unprecedented levels of time with her. So, like, it's just like, you can be so much more efficient if you have remarkable people around you and you're obsessed with not wasting time to fill the slot.

[Sam]

What percentage of those meetings are you making decisions or being informed?

[Gary Vee]

I would say 30% I'm being informed. 70% I'm making decisions.

[Sam]

That's insane. That's hard. The context switching, the best challenge.

[Gary Vee]

It's funny you said that. I've got a bunch of new film people because all my people. Luck. This feels incredible. Go on to these incredible things after they film me for a little while and get all these offers or start doing things. And so I constantly have a drock coming through, you know, every year or two. The number one thing, Sam, every single new admin and every single new person that films me says with like to a T is they do not understand the switching that I. And I talk about something that never even crossed my mind until the last five years when this got louder in my circle. I don't even. I didn't even know that was a thing. Like, I didn't know that people, like, if they're in this kind of meeting that need to, like, decompress or whatever, whatever people are doing to go to the next thing. I. I think I. It clearly DNA. I wonder if growing up in retail where you're just switching, like, everything's just always on. I don't know.

[Sam]

Well, I actually think that sometimes when I say context switching. We had a guy, one of our friends came on the podcast and like, as we were doing the sound check, he got a text from his daughter saying she didn't get into the college that she wanted to get into. And it screwed him up. Like, the. The rest of the podcast was kind of shaky because he was like, oh, I'm so sorry. I can't stop thinking about my daughter just texting me this. I'm so sad for her.

[Gary Vee]

And you're talking about another thing altogether. I'm going from, you know, you have an HR headache, and now you're doing a financial planning for three years and now you're going.

[Sam]

But I'm describing the same thing. Like, if I get bad news, I'm like, how do I not?

[Gary Vee]

Well, I'm over. Well, I'm. I'm building on It, I think. One, it's. It. I've come to learn it's unique to do that. Two, now you're really talking about it. That has definitely been. Even. That has definitely been something I got from my mother, which is being able to carry in the moment adversity and negativity and still show up. Like, I think a lot about that as a leader. Like, I get a lot of bad news every day. One, I'm psycho, and I'm in the HR of all my companies, and now we have so many goddamn employees. Every day someone's dad is sick. It's just like, I've actually. I've actually thought about shutting it off because I'm like, this is just almost getting depressing now because it's always like. Like, I asked the team to let me know about those so I can send a text or flowers or. I want to know. I want to know if somebody in my company is going through tough stuff. And then there's just. When you're in client services, we went 16 months without losing a client at VaynerX. We're ripping hot, right? And then recently, in the last 60 days, we've lost two. And, you know, and they came boom, boom. And the second one was like. And the first one was not surprising. Second was a little bit. And I was walking right into another thing, and I was just like. It's funny you say that. I was like, man, I really got into that because I was pissed and, like, I wanted to fix it, but I knew I had to show up for this thing and this thing and this thing. And then, not to mention all the things that happen in my personal life, similar to the college thing. There's always something just, like, being able to, like, fucking eat shit. And firefight is, like, a really strong emotional framework that is hard.

[Sam]

What about notification fatigue? I tease Sean all the time. Sean, what's the joke? What's the stereotype? If I want. If anyone wants to get a hold of you? Do you. Do you know what that stereotype is about you?

[Sean]

Sean called Ben. I don't know.

[Sam]

No, you. Sean will not reply. Getting in touch with Sean when you need to. Sometimes it's a pain in the butt with me. I tend to reply, but it wears me out. I get so exhausted because I feel like I want to, like, please these people.

[Sean]

Sean's like, worst part is I go to him and I say, hey, long time no talk. When I think of somebody and I see that actually they have been talking and I haven't. I'm like, fuck, okay, I should even send this. Maybe I should just.

[Gary Vee]

I'm a. I'm a mix of the two of you, but I have three full time admins that people know that like people know. My intent is to get back to them, especially if they work for me. You know, friends, acquaintances is a little. People know that it's email, not text. If they really know me. If they don't know me, they may think that I'm just a bad dude. But like when you get. I made a humongous and I mean catastrophic mistake during COVID For some reason, instead of just being like a normal business person and doing it all in slack, I decided my cause. Don't forget I didn't have a computer and I was doing everything through imessage. So when I got my computer, I went desktop imessage and I open Sam. It was the worst mistake I get,

[Sam]

dude, I have that open right now. It sucks, but I open it all the time because I got to type something long and I'm like, it kills me. I have all these notifications.

[Gary Vee]

I would say. I would say I'm in between you guys. I try to reply a lot. I use flights quite a bit to catch up and then if they can't get me, they get to the admins and the admins have a good sense of my reality.

[Sean]

How do you decide what projects to go into? Because, you know, for the six or whatever you said that are working, obviously maybe a couple didn't work and then there's hundreds of opportunities you're saying no to. So what's the. What's the bar now? What's the box? How do you think about that?

[Gary Vee]

Took my tummy just gut. Yeah. Like I want to do this and I want to do what this person.

[Sam]

Say that again, Gary. Say it. Say it. Cute.

[Sean]

Like I said tummy. I got tummy tickles.

[Gary Vee]

You know, it's just there's so much serendipity to it. Ad you like that behind the scenes?

[Sean]

Always good when we can crack it up.

[Gary Vee]

You know, I. Yeah, just. I'm comfortable. I'm very comfortable. And this is a theme of this whole interview and I thank you guys. You've done a good job extracting some different angles out of me. I'm very comfortable dying on my sword, which is my intuition. I'm very comfortable. Like too comfortable.

[Sam]

Well, have you guys ever came close to bankruptcy or not make payroll?

[Gary Vee]

You know, it's funny, but make payroll. Resi was in trouble. I had to put personal money in that I didn't really have at the time, but nothing I've ever operated as the 1A. I'm an immigrant man. Like I'm a real immigrant.

[Sam]

So Vayner's cash flow or, or balance sheet has always been solid.

[Gary Vee]

Yeah, I've had to make payroll my entire life. You know, I got trained by a Soviet immigrant father who didn't even let alone raising capital, forget it. Debt, forget it. Literally didn't have a credit line. And we were in the liquor business where you had to legally pay your bills on 30 day terms, where you went on COD to the whole industry and you couldn't get product. So I think I got trained so well, you know, always have money in the bank for a rainy day and 30 day terms legally bounded by the alcohol laws of America and no credit line that by the time I went to my own journey full time, it was in my subconscious of like, well, you always have that money. The end.

[Sean]

You meet a lot of people. Who do you think is doing cool right now? What are, you know, either businesses that are kind of blowing your mind, maybe something that's taking off faster than you would have expected, maybe something totally unrelated to what you do. But wow, you know, you get exposed to stuff that the average person doesn't. Where are you seeing a lot of heat right now?

[Gary Vee]

Oh, there's so many good areas. I mean like, you know, I'll answer a question that might bring. I'm trying to think about how to bring the most value to the audience. I'll go to places where people are betting on five years from now not to create an exit five months from now. So that takes me to people that are really spending time on advanced AI dating app. Like really knowing where the stigma is today but won't be in five years. Right. Like creating an entire agency of virtual people. Right. Knowing right now it's a little weird. But let's survive three to five years and we're gonna have the CAA of virtual people. They're all gonna be the most famous virtual people and we fucking own it. You're in the IP business, not the representation business that I like. I love everything and this is my wheelhouse, but I love everyone who sells something to the consumer that realizes what live shopping is doing to E commerce is what E commerce did to real, like real life. And so what I mean by that is like in six to 10 years, you know, I think E Com now is what, 25, 30% of the market. Like in six to 10 years, live shopping will actually be 10 to 15% of all commerce. And that is scary big.

[Sean]

Invest in what?

[Gary Vee]

You know, I think I. I did not. I did not. I obviously talk about what not all time. It was not an investment possible.

[Sean]

You know, talk about live selling for years.

[Gary Vee]

John, you'll love this. Anytime I've invested in something that I end up having to talk about a lot, I make a lot of content up front that I'm an investor.

[Sean]

Yeah.

[Gary Vee]

So the way, you know, if I'm an investor in something is I'm saying it a lot early on because I never. So, you know, I'm sure everyone thinks I did. And by the way, it. It ran through my table. Like, I don't. I wasn't actively investing at the time, which is the answer, Sean, to why I didn't. And I know it crossed my desk, but I never took like a meaningful meeting with Grant. But I'm so happy for him. He's done a great job. I'm happy for the people that invested. My friend Chris, who's like in the music business, has a small fund. He invested in it like some, I think.

[Sam]

Sean, didn't they ask you to invest in the seed run and you forgot to reply to the email?

[Sean]

No, no, no. That was a. That was a. Not a. Finally one. I didn't shoot myself in the foot, so somebody else shot me in the foot. I met with Grant. I was like, I love this. My last business got acquired by Twitch. I'm amazing. Have you. Have I told you how amazing I am? You gotta let me invest. The rounded, like just closed. But a lot of times they'll let you in. If they like you, they'll open up or they'll. They'll squeeze you in. He. No, he, he didn't. He. He was just like, let me see what I can do. And I didn't hunt to chase it down like 10 times more. And I just let it go. And that was. That's a big miss.

[Gary Vee]

I have a great email in my inbox from Joe at Better Air, Airbed and Breakfast. Air Bread. Yeah, I'm trying to remember, was it. Yeah, Airbed and Breakfast dot com. That's a good one.

[Sean]

Yeah.

[Sam]

Do you have any other ones that you haven't talked about? Obviously, that's the famous one.

[Gary Vee]

That's like Air Airbnb. But I never saw the email, so it doesn't hurt. Pinterest. I had a guy who was the cso, the chief strategy offer at Campbell Soup, who was like 60 years old, said, gary, you got to look at this startup from Pennsylvania. That's how he said it. My friend's cousin knows the guy. I'm like, okay.

[Sam]

That's like, yeah. It's like I got a guy that's

[Gary Vee]

like getting a script for Hollywood in Chicago, you know, I didn't even, like, contemplate it. And then. And then. Yeah, so that was close. And then. But I got in later through Scott Belsky. What a great investor he is.

[Sam]

By the way, he invested in, I think Uber and Pinterest in the same couple of weeks, Both at a three and a half million dollar valuation. Both was like $25,000 checks. When he had like 75, he told me he had like. He's like, I had. He's like, I had 75 grand in personal savings and I put 25 in each of those companies, which. It's like eight or nine figures.

[Gary Vee]

And by the way, he's better than that even. Like, he's got more wins and he's an operator. He's one of the best.

[Sean]

Yeah.

[Gary Vee]

One of the reasons I'm starting my next thing is a lot of CPGs. Magic spoon. A lot of good brands came to Vayner, wanting us to be the people, but we didn't take on those kind of clients. Some things I invested in, some I didn't. I want to be better at that. The best one, my biggest win that I don't deserve is going to be Liquid Death. Mike's Mike worked at VaynerMedia the day before he started Liquid Death as a creative. And he sent me an email and said, hey, I'm leaving. Thank you for your time. I learned a lot here by the way I'm doing this thing. Would you like to invest? He was a creative. I'm a cliche businessman that thinks creatives aren't business people. Right. So I was like, you know, and I didn't know him well enough because we had a big company at that point.

[Sam]

And I'm like, well, he's also saying that he's launching a water company called Liquid Death. Like, that is like a silly thing on paper.

[Gary Vee]

You'll appreciate this. The way I think about branding and marketing, it actually fits me more than it doesn't for me, the way I like stuff. So that wasn't the crazy part. I was kind of agnostic about that part. I thought it could work, but I didn't think it was brilliant. And I definitely didn't think what a lot of people thought, which is it has no chance. Because on consumer brands, marketing is a stunning variable, especially if the product's a commodity. And Water is a commodity. Right. Like water in plastic versus water in a can. Doesn't really change the variable. In fact, the can is the advantage. So I understood that part. It was more interesting why I invested. It goes back to this nice guy theme a little bit. I just wanted to invest because I want to support my employees on their own ventures. So I literally did it for that reason only. And you know that's going to be a fucking mind. It was first check in.

[Sean]

Right.

[Sam]

Do you ever. Because so you're. You're significantly larger than both of us, but we sort of run in the same world and there's a lot of scammers and shady people in this like content and business world. Business content, whatever you want to call it. And when you like. I've noticed that as we've gotten bigger, I try to be very careful about who I associate with.

[Gary Vee]

Yeah.

[Sam]

Do you. Being a nice guy, do you struggle to like, say, I don't want to be around this person? Like they have a background of doing X, Y and Z. Or they don't. They don't. Or they're, they're. They have political beliefs that I don't buy into and I don't want to be associated with.

[Gary Vee]

I'll be on. And you guys know I never talked politics. Political beliefs won't throw me off because I'm very empathetic that people can see the world. I mean, hate or like ridiculousness on both the left and extreme leftism and rightism as we know it today. Sure. But like political beliefs. No, but I don't think they do honorable work. Sure. I've struggled with that. And you know, also, you know, me being on the speaking circuit for so long, sometimes those, you know, those kind of characters might be at the same place and they want a quick selfie and I don't want to, you know,

[Sam]

that's what I'm talking about. Yeah.

[Gary Vee]

And you know this. I, you know, you're smart and so I know that question is grounded in, you know, that I've avoided a lot of stuff and association and that's the reason. Yeah. Of course. You never. I mean there's people. The amount of people that will take a self. Forget about people we know there are people that are tier 19 people that are trying to do this. They have like four followers and they sell a $4,000 course and they're criminals. Right. They'll take a selfie with me at the airport and then make a post and say that like we had a meeting at the airport to strategize. Their fucking mastermind.

[Sam]

Well, they did when they asked you a question.

[Gary Vee]

It's really. You do have to be conscious of that and you do need to worry about your nil and your reputation. It is on my mind. And now with deepfakes and where this is all going, we're going to go through a really mucky era where I really believe being the bigger person, being a nice person. You know what's really interesting, actually I want to ask you guys a question. Has this hit your radar? This blows me away. We are fortunate. We've worked hard, we had talent. We're at where we're at and what that allows us is to spend some time in private and public settings with other people that have won. The thing that completely rocked me and when it was happening to me and my contemporaries, my era was how many winners? And I mean winners, they've got the girl, they've got crazy money, they've got it will actually still fucking spend most of their time on other winners out of envy or I don't even know what. And I'm like, this energy, like, I'm like, what do you like? I had to say this to a couple buddies, not too long. I'm like, you guys are a bunch of fucking 14 year old bitches. Like, what are you talking about? He first. You should be happy for XYZ that they're crushing it. Yeah, he's not the nicest ever, but he's not a piece of shit. And by the way, everything you're shitting on, you guys do the same shit. What is this? Like you're winning? Like focus on winning. If you're so actually sad that they won even more than you and you got feelings about it, why don't you take these three hours of bitching about this person like yentas and go build something.

[Sam]

Sean, what percentage of incredibly successful people do you know who you think are good, wonderful people with good attitudes?

[Sean]

I think they're good, wonderful people with good attitudes. But they're definitely imbalanced in some core way. Right. Like there's, they're not well rounded, chill ass, you know, people. Right. Like I think the, you're, you're unlikely to be extreme winner without some version of an extreme personality.

[Gary Vee]

Sure.

[Sean]

And I think that's fair.

[Sam]

Hunter S. Thompson said that. He said there's, there's no reasonable people on the town on the top of Mount Everest.

[Sean]

Yeah, Gary, I had a person kind of point this out to me about, about why this happened. So I don't know if you've Ever read, like, the Rene Girard, like, memetic theory? It's like, Peter Thiel is really big on this, which is basically the core thing. You'll get this as a consumer guy, which is that we don't want what we want because we want it. We want it because other people want it.

[Gary Vee]

Yeah.

[Sean]

For whether it's your luxury bag that you're carrying or.

[Gary Vee]

I believe in that. In fact. In fact, this is where all my gratitude comes from. Mother and DNA. I want it for my process, not because others want it. And it makes me feel simple. But it's very clear to me that most are the other way.

[Sean]

Yeah. So. So I think most people have this sort of memetic drive. Right. And this is why you see trends and fads catch on. Because I want to go buy needles right now because all the other kids are buying nidos. And I want to say this because other people say this. I want to wear Jordans because they wear Jordan. Right. So. So that's like a normal thing. And there's a. Another term in that philosophy that's called a memetic rival. And so I was on a. I was on this plane ride and I had this embarrassing moment where I was admitting to somebody. I was like, you know what? Like, I feel stupid even saying this, but, God, it kind of drove me nuts the way this guy was saying that. I was kind of bitching about somebody, as I rarely do, but I was doing it. And I was like. Honestly, I was like, guys, I feel stupid saying this, but, like, that shit bothered me, and I. Blah, blah, blah. And he goes. He goes, you know what? He goes, that person's your mimetic rival. I go, what's a memetic rival? Basically, it's like. It's almost like when you were talking about your. The gummy brand and you were like, well, groons did this, but we did this too. There's a hint of that, right?

[Gary Vee]

Like, sure, sure.

[Sean]

All companies.

[Gary Vee]

But it's so funny. But you noticed that I had to say smaller at the end of that sentence. Yeah. I don't know if you thought that. I get it. I was trying to paint a picture of, like, the pride. To your point, I have. Of doing a lot of things early. But. But. But I do think humility, if you have it with. To your point, competitiveness and alpha, if you can get. I always call it a bridge. If you can have these counter things and find balance in it, you can get really palpable and awesome. Right. If you're nice and humble. But you're also a fucking gangster and want to win and you can push hard. You find this weird middle of peace. That's kind of how I am. That's what. That's where I feel I am right now.

[Sean]

Right, but. But everybody has these memetic rivals. Like, I don't know if you saw when Bezos was launching like his rocket and Elon's rocket and then they had this really passive aggressive thing. It's in Elon's biography. It's very funny. It's like, congratulations to Jeff on the first suborbital launch. Congratulations on the first successful landing from only a, you know, two megaton whatever. It's like they added these little qualifiers. They started blocking each other because for each other they're memetic rivals.

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Right?

[Sean]

And like. And it's a very strange thing. You'd think these are the most secure people on earth, but we all have a no part of us that has that no how you learn to tame it.

[Gary Vee]

It's funny. I literally believe the. I genuinely believe that the far majority of people get to the top from extreme insecurity.

[Sam]

Hey, let me ask you one more question. And you could, and you don't have to answer if you don't want to, if it's too private, but with the six or seven businesses that you've named, they're badass. I'm looking at Deadline did an article about the production company Vaynerwatt and like I'm looking at the people you hired, or I guess they are your co founders. They're freaking awesome. And I was looking at some of your partners and your other businesses. In order to get these stuff the ground, do you have to fund them personally or do you get backers for a lot of these things? Because it's not like I'm reading this Deadline article and you have like a list of like five or six people and they're ballers. And I'm like, those guys aren't cheap.

[Gary Vee]

Watts, Steve Ross, the owner of the Dolphins, who's in Vaynermedia with me as well, he funded that. He wanted to be a part of that. On the rest I funded. So good, so good, so good.

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[Sam]

That's awesome. Like, I was looking at the, I didn't know, but that you had a restaurant and I was looking at that and it looked like a membership club and I looked at the interiors and I was like, it was a, it

[Gary Vee]

was a meaningful build out. Like, no, it's, it's been really cool. Like, I, I'm in a really fun part of my career. I'm actually, I actually just use this platform, this incredible platform. So thank you for having me of talking a little bit more because I actually want to start talking a little bit more about me. The Juggler, mainly. Yes. To your point earlier, I am proud of what I'm doing and I, you know, no one really knows, which is wild. And I'm proud of that too. Right. That goes to the humility. But now I'm maybe ready for being like, hey guys, by the way, I'm not a motivational speaker. I might actually be a weirdly good operator at Scale Wong.

[Sam]

Sean Google Fly Fish Club Manhattan or just Fly Fish Club.

[Gary Vee]

Please come when you guys are in New York. You'll be blown away.

[Sam]

I live here now, Gary. I live on the Upper west side.

[Gary Vee]

So like asap. Email me after this. Like asap. Asap. I want you to see it. It's. It's a three story restaurant with a private posse room. Like, it's real. But more importantly, because you know this, it could also be going out of business tomorrow. Like you could, you know, it meaning it's a, like the business is extremely viable. In fact, Sam, now that you're here, Upper west side, if you just go over to gw, which I know is counterintuitive, the restaurant we opened in Bergen County, New Jersey called Capon's Chop House, we now know we're about to open another one in Westchester. We're about to open 50 of those in high net worth neighborhoods of the biggest cities in the world. We got the model. We got it. And don't forget, this is the brilliance of what I think when, when it's all written. The Vayner X marketing machine impacts all these businesses.

[Sam]

Right. What's the model? It says the model is.

[Gary Vee]

The model is open up the new version of Ruth's Chris and like the best steakhouse that has the most New York City vibes, just not in New York City. And everyone in bridges and tunnels of the seven most important places on earth that have high net worth individuals are gonna sell the fucking shit out of these places. It's not a new invented model.

[Sam]

It's a member.

[Gary Vee]

No, Capons is just. Capons is just a killer steakhouse 2.0 with almost like an STK BLT, you know? Yeah, just one of those.

[Sam]

Yeah, awesome.

[Gary Vee]

You know, whatever you want to call it. But we have a very strong what we do. To Eugene's credit, to Grutman's credit, to Noah's credit, those places have more cool, right? There's that nightlife element. We're going 20% less on that and 20% more on food. We think the secret to retention LTV is just execute a food program that is so undeniable and a little bit of that sizzle. But your steak's got to be right, right, right. Dude, you did.

[Sean]

You've gotten killer chicken parm. It's like, yes.

[Sam]

Yeah. You've got into the best of warmth. You've gotten into this business. Genius. He decided to start an agency and a. A restaurant. The two best businesses on earth. Literally.

[Gary Vee]

Literally the two worst. And again, this is a great way to end it up, which is like I'm playing for what makes me feel good, not just maximizing the dollars. And then to your point, cuz that's absolutely right and really kind of funny. And the liquor store was even worse than two of them. And then on the other side, I'm going to turn veefriends into Pokemon. And it's gonna be one of the most valuable intellectual properties in the world in 20 years, which in an AI world will have an extraordinary amount of value and will be the best kind of business someone can build.

[Sam]

Well, we appreciate you, man. You're the shit. We love hanging out with you. God bless you, brother.

[Gary Vee]

Hey, well, wish you well.

[Sam]

All right, that's it. That's the pod, everybody.

[Gary Vee]

If you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this.

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[Gary Vee]

Journey See you later.