CEOInterviews.AI
Start App
Gary Vaynerchuk
CEO; Chairman of VaynerX, VaynerMedia

Gary Vaynerchuk - How To "Not" Be A FakePreneur

📅 Oct 07, 2026 Joel Brown 17 MIN 74 SEGMENTS · 3 SPEAKERS
The founder of Addicted2Success "Joel Brown" sits down with Marketing Genius, Investor and Multi-Millionaire Gary Vaynerchuk in New York to talk about, Achieving Success on-and offline like a REAL Entrepreneur.

What Gary Vaynerchuk said

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

Gary Vaynerchuk discussed his philosophy on entrepreneurship, emphasizing that there are no shortcuts to success, and that it took 17 years of business experience to build VaynerMedia from 25 to 280 people in two years. He criticized the lack of patience and self-awareness among entrepreneurs, noting that many try to do everything rather than focusing on strengths, and credited his brother AJ for complementing his skills. Vaynerchuk defined success as doing what you want at all times, and highlighted the importance of personality in the transparent world. He advised aspiring online entrepreneurs to audit themselves and ask others for feedback instead of chasing money. He named Medium, Snapchat, Vine, and Wanelo as platforms he's watching, predicting Snapchat would open up for brand messaging. He also recommended late-harvest semillon from Hunter Valley and Alsatian moscato for sweet wine lovers.

Key takeaways

  1. VaynerMedia grew from 25 to 280 employees in two years, but Vaynerchuk says it took 17 years of business context to enable that growth.
  2. Vaynerchuk defines success as doing what you want at all times, and he wants to buy the New York Jets.
  3. Before starting an online business, audit yourself and ask 10-15 close people what you bring in value, not chase high-paying clicks.
  4. He is focused on Medium, Snapchat, Vine, and Wanelo; Snapchat's gamification potential because it forces attention.

Numbers and commitments

FigureWhat it refers toTypeAt
25 to 280 people VaynerMedia's employee growth over two years metric 2:26
17 years Time spent learning about business before building VaynerMedia other 2:26
eight to 150 employees Growth of his previous wine business metric 2:26
3 million to 60 Growth of the family wine business metric 6:02
three cameras that all cost less than one big camera 20 year Cost comparison of cameras for transparency other 9:37

Chapters

  1. 0:00No Shortcuts to Success
  2. 3:52Biggest Entrepreneur Mistakes
  3. 6:19Defining Success
  4. 9:37Funding and Personality
  5. 11:30Life Without the Internet
  6. 12:30Advice for Online Entrepreneurs
  7. 14:20Next Big Platforms
  8. 17:06Wine Recommendations

Questions asked in this interview

6
  1. 2:17What would you say that has been the biggest aha moment in your life when it comes to business?
  2. 3:44What would you say is the biggest mistake that you've seen entrepreneurs make nowadays?
  3. 6:15Was your definition of success different to how it actually is now?
  4. 11:30What do you think you would be doing if the internet didn't exist?
  5. 12:18What would your advice be for somebody that's looking at going online and starting either a business or their own, you know, blog or website?
  6. 14:13What would you say is the next biggest platform that's coming out?
Narrator 0:01 ↗
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.
Joel Brown 0:26 ↗
Welcome to the Addicted to Success podcast. I'm your host Joel Brown, and today we have Gary Vaynerchuk on the Addicted to Success podcast. Now Gary, he is a marketing expert, he's a multi-multi-millionaire investor, entrepreneur, an all-round amazing human being. And I had the opportunity to meet Gary in New York City in his VaynerMedia offices last year. And I've got to say, you know, Gary is full of so much wisdom when it comes to marketing, entrepreneurship, building a company from the ground up, whether it's offline or online. And within the 15 minutes of just sitting down and chatting with Gary, I walked away with so many gems, so many golden nuggets of knowledge that I can apply to my own business, and I'm so happy that I can share them with you today. So, let's get into this right now. This is the Addicted to Success podcast with the man, Gary Vaynerchuk.
Gary Vaynerchuk. Great to finally meet you, man.
Gary Vaynerchuk 1:33 ↗
Me too, man. Thank you so much.
Joel Brown 1:34 ↗
Yeah, I've been seeing you blowing up all over the internet. I know my website, addictedtosuccess.com. You've got very big fans on there, too.
Gary Vaynerchuk 1:41 ↗
Thank you. Hey, everyone.
Joel Brown 1:42 ↗
Awesome. First and foremost, I actually just want to say thanks because you probably don't know it, but you played a pretty big pivotal part in my inspiration to my success, actually.
Gary Vaynerchuk 1:53 ↗
Thank you.
Joel Brown 1:53 ↗
In following my passion and profiting from it. It's funny because about five months ago, I walked in and told my pain-in-the-ass boss, 'I can't work here anymore. It's costing me too much and I'm not coming back.' So, [laughter] thank you, man. Thank you. You inspire me a lot.
Gary Vaynerchuk 2:07 ↗
I appreciate it, man. Good luck to you. It's awesome.
Joel Brown 2:10 ↗
Thank you. So, you've done very well with your family wine business. You've actually built it up to 60 million.
Gary Vaynerchuk 2:16 ↗
Yep.
Joel Brown 2:17 ↗
What would you say that has been the biggest aha moment in your life when it comes to business? You know, what's some of the...
Gary Vaynerchuk 2:26 ↗
There's a lot of things, you know, it's never for me, it's never been one thing. But the thing that really stands out to me is there's no shortcuts, you know. I think that people think that there's some sort of quick move, you know, there's some algorithm, there's some, you know, things you can do that are just going to get there, and there's just no shortcuts. For me, the biggest aha moment has been the last 20 years of my career. I mean, we're now here at VaynerMedia, and you can see it's a pretty big operation. This company's gone from 25 to 280 people in the last two years. It's a lot of growth, but it took 17 years of knowing about business that helped me speed the process up of building this business. It was all the context of building the last wine business from eight to 150 employees, right? It's always the learnings. It's the, you know, it's the gray hairs, mate. You know, they matter, right? Like I was a whiz kid and I'm good and I'm smart, and there's plenty of people watching right now at 22, 23 that can figure it out. But no matter what, you can get better. You get better and there's no shortcut. So the aha moment is that it doesn't happen overnight, you know. You said that you told your boss, 'I'm out,' five months ago, but it didn't happen a day before that. You were doing things that got you to that point that allowed you to make that statement. I think people don't realize how much more time it takes than they think.
Joel Brown 3:44 ↗
Yeah, you're right. For sure. For sure. No shortcuts at all, man. What would you say is the biggest mistake that you've seen entrepreneurs make nowadays?
Gary Vaynerchuk 3:52 ↗
Lack of patience. It's the reverse of what we just said. I think, first of all, there's a huge naivety. There's way too many people think that they can just be a good entrepreneur because it's trendy.
Joel Brown 4:02 ↗
You know, I mean, there's a lot of fake out there.
Gary Vaynerchuk 4:04 ↗
They're out there. I mean, there's a lot of people who are great students, come from wealthy families, have never hustled a day in their life, they think just because they're graduating from Yale that they should be a startup entrepreneur like Zuck was from Harvard. And that's not real. On the flip side, you don't have to be wealthy either. You know, there's a lot of kids who are like, they're immigrants. They think they can do it because there's immigrant stories. I mean, the truth is this: self-awareness, the lack of self-awareness is the biggest issue. People want to be something they're not. You know, I'd love to be the quarterback of the New York Jets, you know, but it's not going to happen. It's just not here, right? And so, I think the biggest thing is that, without the cliché quotes, and here's the real answer: every entrepreneur has strengths and weaknesses. You know, you can't be great at everything. And so, self-awareness matters. And you might be great at things that are not sexy, like operations and infrastructure and profit margin and things that nobody thinks about that I spend a lot of time on. Well, my brother AJ is better at it than I am, and he's been a big factor in the success of this business. I'm great at hunting, getting new business, selling. You know, I think too many people try to do everything, and what they need to realize is their strengths and weaknesses, and they need to focus on their strengths.
Joel Brown 5:15 ↗
Yeah. So, you guys basically, you're complementing each other.
Gary Vaynerchuk 5:18 ↗
Absolutely. And we cross over a lot, like I can do operations, I can do a lot of things AJ can do. He can do a lot of things that I can do, but it's kind of like this, right? And if we focus on the things that are outside of each other, you have more upside.
Joel Brown 5:28 ↗
Yeah. And that's awesome that you can keep it in the family as well, man.
Gary Vaynerchuk 5:31 ↗
Yeah. I mean, that's lucky. You know, I'm used to family businesses with my dad and now with my brother AJ. They're hard, you know, for people that are watching. They're hard, because there's other variables that you don't have with other people. There's a love there that you don't share with other people that make you make decisions not just based on the business.
Joel Brown 5:50 ↗
Yeah. You're making decisions with your heart, not just your head.
Gary Vaynerchuk 5:53 ↗
And as much as heart, and that's why I have such a great culture I put in, they're never my brother. And that's just another variable. And so, yeah.
Joel Brown 6:02 ↗
Yeah. When you first started, you know, you went the social media route. You did the video blogging and things like that. You know, you built your business up from 3 million to 60. When you started to find a little bit of, say, fame and a little bit of success...
Gary Vaynerchuk 6:14 ↗
Yeah.
Joel Brown 6:15 ↗
Was your definition of success different to how it actually is now?
Gary Vaynerchuk 6:19 ↗
Yeah, I think it's always about, you know, change. I mean, what's interesting is my real story is digital and other traditional media. I built up the business already. Like a lot of people think that Wine Library TV and Twitter took it from 3 to 60. It was a part of it, but it was already growing. So, I was already successful when that happened. Then that amplified it and took it even further. Then I started becoming internet famous. You know, pure business-wise, I want to buy the New York Jets, right? Multi-billion-dollar ambition. So success has always been predicated on how close am I to doing that. The flip side is that's just the black and white. The gray, the real stuff, the emotional stuff is how many jobs am I creating? How many relationships am I making? Am I having more fun, less fun, you know? I love the fact that people know who I am. I love the notoriety. I don't mind it. I live for the famous fun. I'm not embarrassed to say, you know, some people are like, I like it. I like it. I mean, first of all, it works for me because I like people. And so anything that creates a, takes away a barrier of meeting new people is awesome for me. Me being recognized and asked to take pictures eliminates the barrier of me meeting that person. So there's a lot of reasons why I like it. I like the leverage that it gives me to make business happen. They're all the real things. I'm not scared to say them. Defining success, I don't know. It's interesting. You know, I'm sitting here. I would tell you it hasn't changed that much. Here's why. My true definition of success is doing what you want to be doing at all times.
Joel Brown 7:46 ↗
Yeah. Living life on your own terms, basically.
Gary Vaynerchuk 7:48 ↗
It's very cliché, but it's a truth. No matter what you are, a businessman, an entrepreneur, an artist, doing what you want to do and being in full charge of that to the best of your ability, outside of outside forces, outside of putting food on your table, like outside the core little things, that's success. And I've had that for a very long time. So it hasn't changed that much, but I think for the people that read Crush It or my other books, decided to start something on the side and they could go screw off to their boss and do their thing, boy, is that some sort of... I mean, imagine, I mean, I can't... I'm asking you now. I'm flipping the switch here. You must have felt insane that next week.
Joel Brown 8:26 ↗
Oh, it's awesome, man. I've been able to actually travel the world. I've, you know, lived a bit more of my life. Fly something that a lot of people do once they retire and they're too old to freaking walk around Italy or India or wherever you want to go.
Gary Vaynerchuk 8:38 ↗
And have very different experiences, right? I mean, like when you're doing those things in your 20s, 30s and 40s, sometimes you're doing it not married yet, you know, which is more rare in your 60s and 70s, not with other responsibilities, no children and grandchildren. I mean, think about all the people that retire at 65. They want to go live their life. I just heard of a story from a friend. Parents worked their ass off. 65, they went, they're going to spend three months in Europe, and one of their grandchildren's sick and they're coming back two days later. So like at 30 you're less likely... Now you have parents and you have siblings that we always have things, life is complicated, but there is no question that you have less, I don't want to call it baggage, less responsibility slash the possibility of things happening that take you away from this freedom in your 20s and 30s than you do in your 60s and 70s.
Joel Brown 9:23 ↗
Yeah. Yeah. You're right, man. Do you know what I like about the way you do things is that you talk about your kids, you talk about your wife as well. You involve your family and teach people that it's more than just what you're doing and just your business. So that's, that's great.
Gary Vaynerchuk 9:37 ↗
And, you know what, I even extend that into friends and acquaintances and people that you just meet. I mean, listen, I got real lucky. The world is becoming very transparent and lots of stuff going on. Look at all the technology. We have three cameras here that all cost less than one big camera 20 years ago, right? And weigh a hell of a lot less. The world is becoming much more transparent and the thing that's going to be valuable is who you are as a human being. Like your personality has become so important. This is the right era for me. I genuinely like people. I genuinely like my book trade stuff that's going on, as you obviously know. Like I'm trading my time, and all my friends are like, 'No, no, no. Make case studies, make standard videos. It scales.' And I'm like, yes, I understand it scales, but then I don't get the experience of meeting more people and them, and it benefits me. Like, you know, very quickly, look, no matter how good of a job I do storytelling out there about who I am, everybody still as a human being has a 1%, even if they love me completely, they have a 1% of cynicism. Like, are we going to get there? And is Gary going to be like he is on camera? Is he really like that? Right? And like to me that's where I really win, is when they come in, they see how happy the atmosphere is. They spend time with me, they see how lightweight I am. I don't need anything. There's no, there's no like, you can't ask me this, you can ask, right? Like we just sat there like, let's go. Right. Then you guys walk out of here and be like, he's pretty much like...
Joel Brown 11:08 ↗
Cool dude.
Gary Vaynerchuk 11:09 ↗
And that, and that to me is more valuable than the scale because that's emotional.
Joel Brown 11:14 ↗
Yeah. Tugs at the heartstrings.

37 more exchanges in this transcript

Sign in free to read the rest of this interview. No card required.

Sign in to read the full transcript

Cite this transcript

APA, MLA, BibTeX
APA

Vaynerchuk, G. (2026, October 7). Gary Vaynerchuk - How To "Not" Be A FakePreneur [Interview transcript]. Joel Brown. CEOInterviews.AI. https://ceointerviews.ai/interview/3039670/

MLA

Gary Vaynerchuk. "Gary Vaynerchuk - How To "Not" Be A FakePreneur." Joel Brown, 7 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3039670/.

BibTeX
@misc{vaynerchuk2026_3039670,
  author       = {Gary Vaynerchuk},
  title        = {Gary Vaynerchuk - How To "Not" Be A FakePreneur},
  howpublished = {Interview transcript, Joel Brown. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3039670/},
  note         = {Speaker-attributed transcript with timestamps}
}