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Gary Vaynerchuk
CEO; Chairman of VaynerX, VaynerMedia

Gary Vaynerchuk - How Real Entrepreneurs Roll

📅 Oct 07, 2026 Joel Brown 21 MIN 1 VIEWS 85 SEGMENTS · 3 SPEAKERS
Here's my interview with the legendary Marketer, Speaker, Entrepreneur and Author - Gary Vaynerchuk! This one was REAL, RAW & UNCUT! Head over to addicted2success.com for more motivation!

What Gary Vaynerchuk said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Gary Vaynerchuk, CEO of VaynerX and VaynerMedia, discusses his superpower of self-awareness, which he says has let him succeed without shortcuts or exploiting others. He explains that his book '#AskGaryVee' was a deliberate brand-building move around his Q&A skills, and that his larger first-week sales versus his previous book were driven by brand strength, not product superiority. He distinguishes himself from coaches and pundits by citing his two actual businesses (one at $50-$60 million, one at $100 million) and his bricks-and-mortar and e-commerce wine ventures. He reveals he consumes only audience feedback, has never listened to a podcast, and sees Musically as the only platform with a shot at popularity. He admits he would be upset if his kids out-hustled him but tells them to be themselves. He advises patience for millennials, warns that fake social media personas will get exposed, and promotes watching one episode of Daily V. on YouTube.

Key takeaways

  1. The '#AskGaryVee' book was intentional, built on his Q&A brand, and sold three to four times more copies in the first week than his previous book.
  2. He has built two businesses valued at $50-$60 million and $100 million, separate from selling information products or masterminds.
  3. He predicts Musically is the only platform with a chance to rival Snapchat, but he's not ready to 'anoint' it yet.

Numbers and commitments

FigureWhat it refers toTypeAt
$50 million Value of one of his two businesses metric 7:49
$60 million Value of the same business (range) metric 7:49
$100 million Value of the second business metric 7:49
18 months Duration of the AskGaryVee show before selling the book timeline 5:42
$18 book Price of his book price 9:15
2.5 years Time since previous interview timeline 13:01
5 years Suggested patience period for VR monetization timeline 13:46
1996 Year he was right about the internet timeline 14:11

Chapters

  1. 0:00Superpower self-awareness
  2. 3:27Intentionality behind AskGaryVee
  3. 5:42Branding beats selling books
  4. 7:49Unasked questions about operator skills
  5. 11:06Consuming only his audience
  6. 12:11Choosing salesmanship as top skill
  7. 13:08Predicting Musically and VR patience
  8. 15:16Kids out-hustling and advice to them
  9. 18:05Top personal brand strategies
  10. 18:54Advice for millennials and final speech

Questions asked in this interview

12
  1. 1:28So, Gary, what do you feel is your superpower?
  2. 2:26Do you feel like you've become more self-aware because you create content quite often?
  3. 4:16Excellent. And you know what, man?
  4. 5:24With this book deal and the campaign, what do you feel you've done different this time that has really worked well for you?
  5. 7:32I mean, we talked about this, you know, a couple years ago, but what's one question that people never ask you that they probably should based off the knowledge and experience that you have now?
  6. 11:59So, if you had all of your skills stripped away from you, right, and you were able to only choose one skill to be extraordinary at, what would that skill be?
  7. 13:32How do you say we can really monetize from that?
  8. 15:16Gary, would you be happy or upset if your kids out hustled you?
  9. 16:33If there was a day in your life where you had to go completely offline, how do you think you would feel about that? Have you done that before?
  10. 17:53What are your top three personal brand building strategies of all time?
  11. 18:42And what would your advice be for millennials coming up right now?
  12. 20:42Where can we get your book? Where is it right now?
Narrator 0:00 ↗
You are now tuned in to the addictedtosuccess.com podcast where geniuses, entrepreneurs, and next level game changers share their juicy little secrets on achieving massive success. This is the advice you wish you heard years ago. Be prepared and take note as we expose the realness and the raw of what it takes to be successful on addictedtosuccess.com.
Host 0:26 ↗
So Gary, you're out there in Sydney, Australia.
Gary Vaynerchuk 0:31 ↗
No, I'm already in Hawaii. I was in Sydney for 11 hours.
Host 0:38 ↗
Oh, dude, you are a hustler. You're a machine, mate. I love it. I love it. So, look, man, I'm really excited because you and I caught up about two and a half years ago. I was in the Vayner Media offices with you.
Gary Vaynerchuk 0:52 ↗
Yeah, I remember.
Host 0:52 ↗
You know what's funny, man? You actually mention quite a few things and you're like, 'I think this is going to happen in the future. I think it's going to look like this.' And for sure, without a doubt, it looks like it right now. So, yeah, I'm excited to have more of a conversation about the future and where you see things going. And also, I've actually brought my community into this this time. It's not just me asking the questions. I've actually tapped into the Addicted to Success community and got them to come up with some questions for you. So, if you don't mind, man, I'll start smashing through the questions and let's work it out.
Gary Vaynerchuk 1:24 ↗
I got to catch this plane. So, the quicker the better.
Host 1:28 ↗
Okay, awesome, mate. Let's get straight into it. So, Gary, what do you feel is your superpower?
Gary Vaynerchuk 1:36 ↗
That's a good damn question because I'm super fond of myself and I think I've got a lot of them. I'm gonna go with self-awareness. Gratitude and empathy were right there, but I'm gonna go with self-awareness. I just think I know who I am. And I think that allowed me to not screw people. You know, you know this. Everybody watching and listening knows this. There's so many hustlers. I mean, 20% of the people listening right now think I'm a hustler, right? Because they've only seen one or two things and they haven't done the homework yet. And so I think self-awareness has allowed me to know what I'm good at, which has allowed me to become successful and not at anybody else's expense. When you know yourself and you know that you're good, you don't need to take shortcuts. You don't need to rip people off. You don't need to do the wrong thing. And so self-awareness has made me successful.
Host 2:26 ↗
Excellent, man. Excellent. Do you feel like you've become more self-aware because you create content quite often? You got to tap into your own self to bring the best out.
Gary Vaynerchuk 2:34 ↗
Yes and no. At 13 or 14, I quit school. I mean, I stayed in it, but I started getting D's and Fs because I knew that I was a businessman. So, that's a very young boy realizing what he was about. So, I had it. I think I dig deeper into it. And I think as a communicator, as somebody who's trying to help other people either figure out how to figure out self-awareness or realize that it's important or double down on it, I think that I've tapped into it more as a communicator. I'm not sure I've been able to exponentially grow my own self-awareness.
Host 3:06 ↗
Yeah. Okay, that makes a lot of sense. So, dude, your book is out right now. #AskGaryVee. I love that you jumped on YouTube and did the whole Q&A thing and it's developed into this book. Now, was that fully intentional? Like, when you started shooting the videos, was that your intention or is this just something that you stem from?
Gary Vaynerchuk 3:27 ↗
Love it. I love it. I wish I could say it was serendipitous. I guess it depends on what you think is cool in life. This one was very intentional. It was intentional to build my brand around my Q&A skills because I think I'm good at it. You know, you interviewed me two and a half years ago. I'd like to think you've interviewed a lot of people. You recognize that when you ask me questions, I'm good at it. I'm quick. I'm sharp. It's got teeth. I know what the hell I'm talking about. Like, you know, it's a place where I separate myself from other people. I don't need slides. I'm not a puppet. I don't have somebody in my ear. So, yeah, I wanted to build my brand more as a Q&A guy. And I wanted the show to happen. I wanted a book to happen from it. And then I wanted my keynotes to basically take a town hall Q&A format for the rest of my career.
Host 4:16 ↗
Yeah. Excellent. Excellent. And you know what, man? I got to say, you've inspired me as a speaker myself now to really not step up with slideshows and PowerPoint presentations. I'm just going out just giving it my all, man. And doing it from a place of authenticity and it works. So, thank you.
Gary Vaynerchuk 4:32 ↗
When you actually talk about stuff you know, you win. And when you use slides, a lot of times you're talking about stuff you don't know.
Host 4:39 ↗
Actually, I interviewed Simon Sinek, right? And I asked Simon like, you know, what's your key to becoming a great speaker? And he said to me, he said, 'I cheat.' I said, 'What do you mean cheat?' He said, 'I just speak about what I know. That's it. I don't speak about anything else.'
Gary Vaynerchuk 4:51 ↗
Him and I are homies and we've talked about this.
Host 4:54 ↗
Yeah. I mean, I will. It's why I come across cocky and egotistical because I only talk about the things that I'm the best at.
Gary Vaynerchuk 5:01 ↗
And it makes me, you know, like if you talk to me about healthcare or world economic issues or oil, oil price, or artificial intelligence or a hundred other thousand billion things, I would come across very humble. You want to talk about marketing and building businesses, especially in 2016. Yeah. I'm going to bring it like that. And that's why I stay in that place.
Host 5:24 ↗
Yeah. Yeah. And you bring the heat, man. For sure. For sure. What has been the number one lesson that you've learned with launching this book? Because I know, you know, you've done some campaigns with the other books that you launched. I've read them all. They're awesome. With this book deal and the campaign, what do you feel you've done different this time that has really worked well for you?
Gary Vaynerchuk 5:42 ↗
It reminds me that my thesis that I live on, which is branding and marketing is better than sales and transactions, is true. I mean, when I wrote Jab, Jab, I'd been undercover for a while, right? Like, I've been building Vayner Media and, as you know, because you're a student of the game, I wasn't really out there. And so, what I learned was by doing the Ask GaryVee show for 18 months, by putting out so much content, by redoing my GaryV.com website, by putting out a podcast, by building the brand, by the time I got around to selling the book, it was sold, right? So, I sold three times the amount of books, four times the amount of books in the first week of this book than I did of Jab Jab. And that only speaks to my brand was bigger. It was my brand, right? Nike doesn't have to make the best sneaker. They've got Nike. If you and I start a sneaker company, we have to make the best sneaker.
Host 6:39 ↗
Got it. Got it. Makes total sense. So, look, I've got a great question here from one of the fans of yours. He asks, 'If you could ask one person, dead or alive, a question and they had to give you the most honest, truthful answer, who would you ask and what would you ask them?'
Gary Vaynerchuk 6:56 ↗
I would ask my grandfathers. Both my grandfathers passed away before I got to meet them. I would just ask them, you know, if I could really ask them if they were really alive, if this question went that way, I'd ask them, 'Yo, what you see I'm doing, is that real? Like what do you see that in you? Like were you like that? Were you unbelievably handsome and charismatic? You know, like I would just ask them, you know, how it was in the old country, how they hustled, you know, cool stuff like that.
Host 7:32 ↗
Yeah. Awesome. Awesome. Look, dude, you get asked a myriad of questions about entrepreneurship, motivation. I mean, we talked about this, you know, a couple years ago, but what's one question that people never ask you that they probably should based off the knowledge and experience that you have now?
Gary Vaynerchuk 7:49 ↗
I don't know if there's a question, bro. I think that I'm surprised that people don't realize that I've built two businesses, one at 50 million, 60 million, and one at 100 million that have nothing to do with selling people masterminds or ebooks or any of the cliche stuff that, like, I'm surprised that people don't. I think my personality confuses people and they don't understand how much of an operator I am, how much of an actual business man I am, not a motivator or pundit or talking head. So I guess questions around leadership or organization or P&Ls or real business stuff isn't the sexy thing to ask me because of the way I portray myself on social, I guess. I don't know. But sometimes when people are like, oh, like when they take a jab at me, a stab, make fun of me or try to argue with their buddy if I'm good or not, I'm confused that people haven't reconciled that I'm building actual businesses. I mean, my first business was a bricks and mortar liquor store and an e-commerce wine business and I was 34 years old before I started talking to the world, right? I'm not a podcaster or a pundit or a journalist or a coach.
Host 9:11 ↗
Even though some people see you like that, man. They see you as an inspiration. That's for sure.
Gary Vaynerchuk 9:15 ↗
And by the way, I am inspirational. I'm motivating. I'm a good communicator. I'm a great head coach kind of guy. And I'm flattered by that. I'm just not just that. And more importantly, I don't like being put in the same breath as people that sell information products and masterminds because I'm not that. I'm not putting out Instagram quotes so that you then click my URL in my profile and then sign up and pay me $10,000 a month to tell you how to make money. That's not what I do for a living. I put out the best content in the game every goddamn day for free and then every three years I ask people to buy an $18 book.
Host 10:01 ↗
That's a good game plan.
Gary Vaynerchuk 10:02 ↗
It's a big difference, bro. And it's a good game plan because I can actually build businesses. It's not a good game plan for everybody else who thinks they can start a business. It's a better game plan for them to sell people information and access because they can't build a business. But that's also what pisses me off, that people actually listen to these people because they've never, like, why don't you ask your mentor or your coach or your mastermind group what business they've ever built besides selling information to people? Shouldn't that be a prerequisite?
Host 10:39 ↗
Yeah.
Gary Vaynerchuk 10:39 ↗
The problem is a lot of people listening and watching right now want to also then sell people. They don't actually want to build a business. They just want to play that Ponzi game of being somebody's coach. And that's real.
Host 10:52 ↗
Yeah. That's real. That is real. So you obviously see yourself as a creator, right? And so, how do you stay away from consuming too much? Because I know you're on all these social media platforms and I know that obviously you're building brand and building exposure.
Gary Vaynerchuk 11:06 ↗
The only thing I consume is my audience. I don't have a clue what you've been up to for the last two and a half years or Seth Godin or Guy or Ferris. All my homies, all I know are crushing it. All I know are brilliant. All I know are the best. I just don't know. Do you know how many podcasts I've listened to? Zero, zip, zilch. And I know Lewis and Alter and Art of Charm. I'm on those shows, but I don't consume it. What I consume is everybody who listens to those shows points of view on the content that I put out so that I can adjust to the audience.
Host 11:48 ↗
Wow. That advice right there is a game changer. So, anyone that's listening, start implementing that.
Gary Vaynerchuk 11:54 ↗
Yeah. Do that for a year and see what happens. You'll be blown away.
Host 11:59 ↗
Yeah. Excellent, man. Thank you. Thank you. So, if you had all of your skills stripped away from you, right, and you were able to only choose one skill to be extraordinary at, what would that skill be?
Gary Vaynerchuk 12:11 ↗
Salesmanship.
Host 12:12 ↗
Salesmanship. Cuz it's survival, right?
Gary Vaynerchuk 12:14 ↗
Like maybe I wouldn't be as noble. Maybe I'd be more of a douchebag. Maybe I wouldn't be as successful because I think being a marketer I'm better. But if you're not a salesman, you will lose. You will lose.
Host 12:27 ↗
Amen to that. Amen to that. Yeah. Grant Cardone and I were talking and he said when he wakes up in the morning, he's like, 'Where's my money? Someone's got my money.' And he's like, 'You got to get out there and ask for it. You can't wait for it to come to you.'
Gary Vaynerchuk 12:40 ↗
Yeah. Hell yeah. Got to grab it.
Host 12:42 ↗
Yeah. So, last time we chatted, you were telling me, you were like, 'Look, man, you need to be on Snapchat. Snapchat is the future.' And surprise surprise, it freaking is. So what do you feel now is the next and, by the way, real quick and make sure all the homies that are listening right now know how long ago that interview was.

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Cite this transcript

APA, MLA, BibTeX
APA

Vaynerchuk, G. (2026, October 7). Gary Vaynerchuk - How Real Entrepreneurs Roll [Interview transcript]. Joel Brown. CEOInterviews.AI. https://ceointerviews.ai/interview/3039669/

MLA

Gary Vaynerchuk. "Gary Vaynerchuk - How Real Entrepreneurs Roll." Joel Brown, 7 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3039669/.

BibTeX
@misc{vaynerchuk2026_3039669,
  author       = {Gary Vaynerchuk},
  title        = {Gary Vaynerchuk - How Real Entrepreneurs Roll},
  howpublished = {Interview transcript, Joel Brown. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3039669/},
  note         = {Speaker-attributed transcript with timestamps}
}