In this Business Blast Podcast episode, host Tyler Wagner interviews entrepreneur and internet personality Gary Vaynerchuk (GaryVee). The conversation opens with Gary sharing a memorable story about personally delivering a case of cheap wine to an elderly customer, using the anecdote to illustrate his principle of putting customers first and modeling integrity for his team. He then addresses common misunderstandings about his public persona, emphasizing that he did not inherit a business, that he does not advocate 18‑hour workdays as a lifestyle, and that his messages are often oversimplified when taken out of context. Gary explains why social media is a game‑changing platform: there is no middleman, attention is underpriced, and anyone can create content to pursue their goals. He stresses that the first piece of advice for aspiring entrepreneurs is self‑awareness—recognizing whether one truly wants to be an entrepreneur and understanding the loneliness and difficulty of the path. When asked about advice for his younger self, he admits he neglected his social life and suggests attending more parties. He outlines his simple daily routine (phone, bathroom, workout) and shares two tactics for developing self‑awareness: quiet introspection free from others’ opinions and building a trusted circle that can give honest feedback. Regarding happiness, Gary argues it boils down to having the freedom to do what you want when you want, noting that loving his work, not material symbols, brings him joy, and that many people could increase happiness by simplifying their lives. The episode ends with Gary posing a reflective question to listeners about the disproportionate influence of someone they value due to insecurity. The podcast concludes with a brief Anchor promotion.
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Alright everyone, welcome back to another episode of the Business Blast Podcast. I'm your host Tyler Wagner. Today we got GaryVee with us. Welcome to the show, brother.
How are you, bro?
Awesome, man. How are you?
I'm really well.
Thanks for coming on. Really appreciate it.
My pleasure.
The first question I have for you, the first question we ask on this show is what is the best story from your life that has an underlying valuable message?
Jesus Christ. God, I feel like my whole life is a bunch of stories. Probably when I drove a case of $20 wine. Literally, there's something called Sutter Home, I don't remember if it was, I think it was Beringer. Beringer White Zinfandel, which is like pink wine that's sweet. Not the rosé stuff that's gotten cool in the last couple years, but this is like White Zinfandel, like your grandma's wine. And during the holidays, right when Wine Library was just just about to explode. We got an internet order, we were just doing that, and the FedEx delivery shipped it to the wrong place, and the woman was extremely elderly, and it was an extremely busy Saturday, or holiday day, every day feels like a Saturday the last 10 days of the year, where this $3 times 12, $36 case of wine. $36. We made zero profit, we lost money, it was lost leader. I decided, 'cause everybody knew like we had this issue, I decided to grab the case, put it in my car, it was bad weather too so it took me forever, and deliver it to her and then come back, giving up 2 or 3 hours in the store where I could have made $15,000 to $50,000 because I thought there was an opportunity to show to my employees that doing the right thing is always the right thing. And we don't pick, you know, rich guy, Short Hills, New Jersey, over Old Lady McGee up in Bergen County. And they were shocked, my organization. But it was a story that, you know, by the way, the best part about stories is like 7 years later I heard some kid telling it to some other kid, and it was like, "I killed a grizzly bear and made the wine myself!" You know? But at its very basic, I delivered a case of wine that was worth no money to the business, but it was a great opportunity to tell everybody what our business was about, which is customer-centric and do the right thing when you can. And I genuinely believe I'm a very complicated character now that I've gotten to know myself and like watch how I produce content and where I sit in the lexicon. But I feel much like that case made no sense, I believe much of the content I make now and many of the things I do now that are sometimes misunderstood will be looked upon in a very different way in 20 or 30 years, and that's why I think that story came to mind.
[Speaker] Yes, awesome.
[Speaker] And just to create clarity, 'cause I think people are confused when I sometimes say that, there's a ton of people who are very much affected in a positive way about my message, but there are enormous amounts of people who don't fully understand it and don't know every nuance and don't take the time to realize that my dad didn't give me a business, but I built a business for my dad, so that excuse is gone. Or that I don't tell people to work 18 hours a day. I tell them that if they're complaining and they hate their life, work a lot of hours to get out of your situation. Or be self-aware and know who you are. Or stop being entitled or fantasy about it. If you want to build a $10 million business, it's gonna take hard work. You know, and so it's more about entitlement and complaining that I'm attacking, right? And so I watch the confusion in the system and I have empathy for it because we're in a headline reading society. You can't watch all my content and get every nuance. I have to do a better job to create clarity on my content, but most of all if you watch one 1-minute video on Instagram and you make an assumption, we are all vulnerable to that.
Definitely, yeah. I think you answered some other of my questions, but we will go in. The next one is, what is the most valuable piece of information we should know about social media?
That there's no middleman and you can't blame anything anymore and all the opportunity is there for you, the internet. And the communication level on the internet, social media, is available to everyone. Good, bad, and indifferent. And a lot of things that people are worried about in society today are also the reason that everybody watching right now has a huge opportunity to take advantage of it, and that the attention is underpriced, and that you should be making content for it, because then your dreams and aspirations and wants can come a little closer.
[Speaker] And what's your number one piece of advice for entrepreneurs?
[Speaker] First, figure out if they're an entrepreneur. You know, my number one piece of advice is self-awareness. Entrepreneurship got cool.
[Speaker:GARY] Yeah.
[Speaker] And when something becomes cool, everybody wants to be it. And entrepreneurship is hard and lonely. And being an entrepreneur is different than being a successful entrepreneur. And so my number one piece of advice for entrepreneurs is to find out if they are one because I love it and it's what I was, but it doesn't make you good, bad, or indifferent if you are or aren't an entrepreneur. Finding who you are, deploying self-awareness, That's the goal, putting yourself in a position to succeed. So many of today's entrepreneurs would be amazing number 3s or 4s to actual entrepreneurs and would be happier and more successful for everybody. So self-awareness is my number 1 tip.
[Speaker] Okay, and then if you could give your younger self one piece of advice, what would that be?
[Speaker] Go to one goddamn party. I mean, I really, really did go overboard. Like, I basically had no social life from 18 to 28. That's, you know, that's extreme. I mean, for real. I closed the store every Friday and Saturday night in my 20s.
[Speaker] Mm-hmm. So, okay, yeah, no, that is very extreme. I definitely went to a few parties.
[Speaker] Yeah, and I think that's why I don't like to give advice predicated on me because I know I'm an extreme version, and so I think about that.
[Speaker] So I watch like a ton of your content. I haven't heard you speak on these things. So do you have a morning and/or night routine And if you do, what is it?
No, I mean, I think the closest I have is I wake up, I grab my phone, I go poop, I go work out. So that is my routine, but it's not super complicated. No, I sleep well. I fall right asleep when I want to. It's 'cause I put out a lot of energy all day, and I think I get tired. And I feel like I'm calm and happy, and so it allows me to sleep pretty easily.
Okay, and then my next one for you is if you were to give one piece of guidance to help people get self-awareness, or become self-aware rather, what would that be?
You know, I think there's two things that stand out for me. One, I think a lot of people just know they're lying to themselves. They're posturing. They're peacocking. So like, just get into that quiet place and be like, hey, it's okay. You gotta eliminate other people's opinions, which allows you to then actually acknowledge what you already know. Right? Number two, create a safe environment for people that care about you to say, hey, I'm really struggling. I'm trying to figure myself out. Even if you tell me I'm shitty at everything I thought I was great at, And do it for like 2 months. Set up a kumbaya for 2 months. Make the 10, 15 closest people to you comfortable to tell you the truth. I think that helps as well.
[Speaker] Okay, and then in your opinion, what is the key to happiness?
[Speaker] I mean, there's so, I think everybody has a slight variation, but I think all of it gets to a place of like, can you do what you wanna do when you wanna do it?
[Speaker] Mm-hmm.
[Speaker] Right? Like, that's just like, You know, because for example, the key to happiness for me is to work. Like, so many people struggle with that with me, but I love my process. Like, I like doing my job more than the stuff that my job affords me to do. It's not more fun for me to go on a 4-week vacation. It's not more fun for me to have a Lamborghini. It's not more fun for me. It's more fun for me to be an operator than be in HR meetings and put up-and-coming people on by giving them 10 minutes.
Yeah, brother.
But I mean it, that's like more fun for me.
Yeah.
I like my process. Boy, I wish, so for me, by loving my job, I'm putting myself in a position to do what I want, when I want, how I want. For a lot of people, that means making $49,000 a year working 9 to 5 in a stable job at a stable company So that, because what they want to do is also, they do want to be on a softball team. They do want to watch 2 hours of TV a night. They do want to play video games. They want to go to every recital. They, like, that's fun for them. And that's amazing. Like, I equally think, like, the extreme version of me is absolutely found in other people who work 25 hours a week, live the most humble lives, and are as happy as I am. I think most people are in the middle. And I think they need to figure out which one are they. Like, I think a lot of people making $150,000 a year should make $97,000 so that they can be happier because they can buy a smaller house and a less fancy car, but they would be 10 times happier. We're slaves to items that make us look good to people we don't care about.
[Speaker] Yeah. Dude, incredible. Thank you for coming on. The last one I have, I thought I'd flip the script.
Do it.
You got a question of the day for our audience.
I appreciate that, I'm going. Who's the person that is impacting your life disproportionately because you value their opinion out of your own insecurities, and do you feel like you have a way to get out of it?
Awesome, man. You're welcome.
Thank you so much. Thank you.
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