My BIGGEST achievement in life

0:00You're a successful, very successful entrepreneur, bestselling author. What achievement are you most proud of? The fact that now at 48 years old, there is a substantial amount of human beings that walk around the earth that are asked, what's it really like to work for Gary? Or what's he really like? And that I know that 93.7 % of them have incredibly good things to say. And that is by far my biggest accomplished profession. Was there ever a point where you considered yourself a success or is that an ongoing, evolving journey always? Yeah, I think I decided I was a success probably when I was 10.

0:43I played it reverse, I think, in hindsight. I kind of had this really early framework of, I think I figured out that school doesn't matter and that being nice and being good at something does. I've never thought of it as I'm success. Like, I don't think today, like, I'm a success. I kind of feel like I've always felt that I was a success. I think that's really good mothering, to be frank. And I think that, I think the luck of the draw of humility is a DNA trait. Not to be in conflict to conviction and competitiveness and I think, you know, it's a funny mix. But honestly, I've never thought that I've made it or I've made it, I've never thought in the terms of success.

1:28Successful people never often do. Is that true? Yeah, yeah. Yeah, it's cool. Makes sense. But I sat next to your parents, I think, for the lunch. Yes. Very humble, very lovely people. Yes, thank you. They, do you know if they ever considered you? Because they must have. You must have done something where they thought, my boy. Yeah, actually, you know, it's funny. I'm going to go run and ask them right now. Actually, I'm not even kidding. I don't think I've ever asked them, like, what was the moment? And they may say when I did the Conan O 'Brien show, that was wild. I was running a wine store in New Jersey, started this YouTube thing and then six months later, I'm on the Conan O 'Brien show.

2:01or maybe right away, because I built the family business pretty big. But, yeah, I mean, as someone who has a 15 and 11-year-old now, I get it. Like, I think, you know, all the little things my kids do well, I'm like, everyone, you know, like, it's what we do. It's a very fun thing. I'm enjoying getting to an age where my kids are a little bit older, where I can even appreciate more why my parents are proud. Like, I get it. You just, when you love your child so much, which anything they do makes you kind of weirdly proud. Yeah, absolutely. And as a father or two, I tell you. You get it, right? Look at how fast they ran.

2:36You know, like, oh my God, you know. Whose career inspired you when you were developing your businesses, or maybe still does? No one, and that's not an audacious bad statement. I just didn't look at it that way.

2:53Richard Salzman owned a liquor distributorship. I have no clue how big or not good it was. I love that his people adored him. And ironically, the reason I probably just brought him up is he just passed away. And my father texted me from the wake, I was traveling, and he said, you will not believe how many people were there. And I smiled like a fucking motherfucker, because I'm like, that's the life. Forget about the accolades or that. And it was people like that, the Richard Salzman's of the world, more than the Bill Gates or the Steve Jobs or the JP Morgan's. I was inspired that you could be rich, successful, but nice.

3:35I hated nice guys finish last from my earliest of age. And I think now that I'm getting into my middle part of my life, I hate it even more. And so I was always inspired by kindness that didn't compromise financial success. Sounds like you're saying something like the sum of who you are is more important than the sum of what you have. Do you know any very rich people have four people show up to their funeral? I think that's life. Very true. So this is one you've probably been asked in numerous guises over your time. What are the foundations and fundamentals that you need to build success that you think you can narrow down to a few things?

4:20Humility. And on the other side, blind, audacious, optimistic conviction. Polar opposites. Hard work, like real hard work, but so much self-awareness that you know when you need to rest. Competitiveness, but you understand it's a game, so you don't actually hate. That's the framework I live in. Very opposite traits that create that strength of accomplishment. And do you have any particular habits or repetitive things that you've done throughout your career, which have stood you in good stead and you believe have been sort of the cornerstones of this. Yeah, I have a framework of aggressive perspective every day that something bad is going on, which is every day when you're at the scale I'm at.

5:11I just remind myself that if everything was going great and someone in my family was sick, that I wouldn't care. And so what has made me very capable is I am completely detached from my public persona and my professional success. I don't get my validation or affirmation from it. And so I would say aggressive perspective. Nice, very good. And what's the best business advice or career advice you've ever received? And the worst, if you've received it. Is the best, which was actually given by that man up there, my father. You know, I'm comfortable in saying what I'm about to say. I think I taught my dad more than he taught me.

5:54I know that's like, it's just real life. I feel that to be true. But that motherfucker taught me that my word was bond and that you needed to honor your word. And I believe with my personality of gift of gab that there was a worse version of myself that was in the cards had I not been parented well and he tweaked me in a way of like old school. My dad literally thinks a slight embellishment is like an aggressive lie. and that was a jolt to me because I grew up as a sales kid and I would tell Harry, I would be like, where's this from? I'd be like, oh, it was found in a rare attic. I would do anything to get her to buy this bell and that is, my father changed the course.

6:37So that's the best advice. Your word is bond. That matters. I mean, the worst advice was from equally from the liquor business. The gentleman once told me, Gary, in retail, you can do price, selection and service. You've got to pick two out of those and that's how you build a business. And I sat there as a 22 year old and I'm like, fuck you, I'm doing all three. And I built the biggest wine store in the country, or one of them and it was because I didn't take that advice. And it was bad advice. I think when you operate something, you should do everything you can for a customer. Very good advice.

7:13And I'm sure you're a mentor to a lot of people within your company, both in person and online. as well, I know you've got a huge following online who look to you for this kind of advice. Have you ever had a mentor as such? Oh yeah, I mean my mom and dad are my mentors by far. Like my mom especially. Like my dad, obviously I just told you, my dad has been a mentor but I would say the two mentors, the three mentors are my father, my mother for sure, my mom completely shaped me. Completely. Completely. molded me from a piece of clay. And then I'm gonna give you a weird one that I really believe to be true and I think it is my core strength.

7:57I believe that the market has been my mentor. Customers, they've taught me the most. When they didn't buy my lemonade, they taught me. When they bought it, they taught me. When they didn't buy my sports cards, you know I've had a really long career. Six, seven, eight, nine, 10 years old. Lemonade, washing cars, shoveling snow. I always did it. 12, 13, 14, 15 baseball cards. People coming to your table, not buying, buying. And then 16 to 34 liquor store, store, customers coming in. The market has been my mentor. She taught me, the market taught me. It taught me what it liked, it taught me what it didn't like and most of all it taught me that it never stays the same.

8:40Very, very interesting. You know, you're obviously again a mental and a leader to a very large group. What personality traits do you think every leader should have and who is one of the better leaders that you've encountered?

8:57I want to give someone roses, but it's hard because I'm very scared to give love to someone without knowing if they're really great. Who's a great leader? Or just traits. Well, I'll do traits for sure. Traits are very easy. One, humility, and I've touched on it. Do you think that you work for them? I think I work for Harriet and Dustin, not that they work for me. I understand I pay their salary. I work for them. Then, in return, they can work for it. Not me, it, the logo. So I think that's a big one. I think lead by example, I think hypocrisy destroys people. When your boss tells you to do something that she or he doesn't do, it fucking hurts.

9:38So I think non hypocrisy individuals. So authentic, honorable. I think tenacity. Like real talk, the one thing that Dustin and Harriet can't appreciate is how lonely it is for me. It's all me. At the end of the day, like real talk. When you're laying, there's nobody, like Dustin could look at Sid and then look at me. Harry can look at me and Andre and Avery and Mark. It's me in the ocean. And I think tenacity and adaptability, when you're at the end of the rope, you're a firefighter. It's you in the fire. And so I would say adaptability and tenacity. And is there any advice that you wish you had earlier on in your career that you know now?

10:30Yes. My kryptonite. the greatest thing that I did wrong for 20 years was I didn't have good enough candor. Which is wild, because I'm so candorous in public settings. In this interview, on stage, my candor is my superpower. But one on one, even today, I would say I'm a five out of 10 if I had to tell Harriet and Dustin something I really needed them to fix. Because I like them too much. It's too family business. Like, it's, and honestly, I used to think of it as my superpower and it's my vulnerability. It's not fair to them if I'm not able to articulate, because then they don't have the ability to fix.

11:04So I would say that I wish somebody grabbed me at 25 and said to me, and my dad in a version, he did part of it, but he didn't really have the inner people skills. And so I really regret, and I don't use that word lightly. It's not a word that I have a lot of, but I did not manage everybody to my best of my abilities at 25, 30, 35, 40 because I didn't have candor yet. It was the missing piece. and now I call it kind candor. Dustin, I love you, brother, but if you don't do this, I'm gonna lose the fort because everyone knows that I'm letting you get away with it. These are conversations I'm starting to and again, I gave myself a five, which probably means it's a four.

11:44And so, candor. Okay, and to finish, this is a bit out there, but what one decision could you make today that could have the most positive impact on your life going forward? Professionally or personally? Anything. I actually use the same for both. you must cut out the most negative person in your life. Now, if that is your mother, I'm not advocating for never speaking to your mother again. If it's your mother, I would say that you need to limit the exposure. So if you're talking to your mom who's extremely negative three times a day, it might need to go to three times a week. But if it is not your mother or your best relatives or your best friends and it is an acquaintance, a boyfriend that you haven't married yet, an employee, an employer, you must cut out that cancer.

12:32It will have the greatest impact on your life. That's fantastic. Thank you. Cheers. That's brilliant.