00:12 Scott Gerber: What is it like to first transition into a family business? What was your experience with that and then ultimately, in taking over that business, what are those key different business developmental stages?
00:22 Gary Vaynerchuk: So, a lot of people see that I came into a family business and worked successfully with my dad, and we built a big business and we still love each other, hence some of the videos on Wine Library TV when we did shows together and I'd get 50 e-mails a week, still to this day, where I think it's less of my story, of like, "How are you doing this? How did you this with your dad? My dad won't let me do anything. My mom won't listen to any of my ideas. Da da da da da." I came into my family business when I was 14 years old, so it was very easy for me to listen to my dad. I was like a kid, kid, kid. I didn't go to some fancy school, I didn't get an MBA and then came into the business and thought I was better than my dad, I was a kid. That being said, I was very egotistical in my entrepreneurial spirit, and so even at 15, I probably thought I did everything better than my dad.
01:03 Gerber: And you were the CEO? [chuckle]
01:04 Vaynerchuk: It wasn't that I was the CEO, it was that, I think what I do for my business today, I think comes from my dad. My dad was always willing to listen to me, because I proved very quickly to him that I was good.
01:14 Gerber: In what ways?
01:15 Vaynerchuk: I sold a lot of crap, right? And I mean it that by like, "Hey, we have 50 cases of this wine, and everybody tried to sell it", and his 15 year-old son, who's clearly not able to drink the stuff and clearly knew nothing about it, was selling more than everybody else in the staff combined, in the four hours that he was in on a Saturday, that made him take notice.
01:32 Gerber: How did you do that though? Take me through how like an experienced salesmen, a connoisseur of the product, knows less than you?
01:38 Vaynerchuk: I wish Malcolm Gladwell... Well, easy. Malcolm Gladwell will tell you the 10,000 hours matter, and I will tell you that I put in the 10,000 hours of being a salesman, between being five and 14, than most people put in into their studies, and it's true. It's funny. If you really watch all the content that I've put out for the last five to six years, I'd gotten louder about me being a bad student, because even five years ago, there was a part of me that was embarrassed about it. You know, it's funny, when I say on stage that I failed all my classes, everybody laughs. And I think they say to themselves, "Oh, he was a B-C student", I was really an F student, right? And so, I was always embarrassed of that, that all my... I grew up in an immigrant way, when all those Russian families came to America with my parents, all those kids were taught to go to school, that was the way out, right?
02:22 Vaynerchuk: They were gonna go to Harvard, and Yale, and NYU, when it was... Or what's was gonna be, and that was your way out. The thing I leaned too earlier, with my mom staying out of the way, it wasn't my path. When I was 11 years old, I was going to malls on the weekend, and selling baseball cards to grown-ups, with grown-ups and doing it better than everybody else 'cause it's just my God-given ability, right? Like, why does Lebron dominate? Like, right? Like why is Alicia Keys so damn good? Because you're born with talent. I don't think that people have really absorbed salesmanship or entrepreneurship as a talent, until just now, it's just starting to happen. And so, you know, if I was taught, why New Coke failed in third grade, I'd be an A student. If I was taught like, how to re-invest your funds into hedge funds, when I was in fourth grade, I'd be an A student. I didn't give a crap about Pluto, or dissecting a frog.
03:11 Gerber: Did you have a mission to make your father see that you wanted this business? Or was this a...
03:16 Vaynerchuk: Absolutely.
03:17 Gerber: So, you knew that you wanted to take over the business at an earlier age or were you apprenticing that role?
03:20 Vaynerchuk: At 16. At 14 to 16, I was like, "This sucks, I wanna open up a hundred thousand baseball card stores." And then when I realized people collected wine, there was that hook to my heart, 'cause I came from collecting and selling things. I mean, the reason I sold a lot of wine when I was 14 was 'cause I'm full of crap. Like whatever it took me to say, to make them buy that bottle, I did. Luckily, through the next seven years of my life, I got a lot more authentic, but I was well on the way of being a jerk-off auto salesman.
03:49 Gerber: What would you tell people today that are looking to take on a family business, that are looking to come up the ranks and eventually be the head, in-charge? What were the missteps that you took in that relation... What were the missteps your father took in that relationship, and ultimately, that allowed for a successful transition?
04:03 Vaynerchuk: I'm gonna go reverse on you. So, it's not the missteps that are gonna teach anybody, I'm gonna say one thing, and it's the only reason that happened. We loved each other so much, but we loved the business more. I'm gonna say it again, 'cause it's really, really complicated to understand what I'm saying. Because let me tell you something, it was ridiculously hard, and it's like far the most difficult thing I ever did. Running a business with my dad, who I loved and respected so much, who I thought was underestimating what he was accomplishing, at the same token, not agreeing in principle on any of the operational aspects of the business. My dad thought that our employees were stealing, and were the enemy. I thought they were the foundation of what we were gonna do.
04:46 Vaynerchuk: My dad did believe in vesting in the business, so that helped me, 'cause I wanted to be on the attack, so we agreed on that. But we disagreed on an everyday basis. I cried a hundred times, in a two-year period, trying to fight, to like do what I wanted to do, but the thing that happened was, we loved each other so much, he loved me as a son and being the father, I loved him as being my dad, and like giving me the shot, but we loved the business more, which meant, push comes to shove, as long as I was driving results, my dad was letting me do what I wanted to do. If he did not do that, I would have left. And I think that that's what most fathers and mothers are doing, they're not letting the kid, even if they show them some results, actually make decisions and if the kid's good enough, and talented enough, they're gonna leave.
05:32 Gerber: You're a parent now? How do you change that mindset in your own parenting of your children?
05:37 Vaynerchuk: So, my dynamics can be so different. I walked into a $3 million a year business, that was running on 10% gross profit. This wasn't, we weren't like balling it up. I planned, by the time Mischa and Xander are ready to make some decisions, to ball it up, in the way that I want to, which is, I may own the New York Jets by the time Mischa and Xander wanna make a decision, right?
05:58 Gerber: At this rate you might be.
06:00 Vaynerchuk: I'm trying, right? I'm gonna need to do something really rogue, but like the fact of the matter is, is that I'm dealing with a totally different thing which is living in the upper East side of Manhattan, raising children as an immigrant, how the heck am I gonna keep them grounded when they're gonna go to million dollar Bar-mitzvahs in 10 years, right? And like I'm gonna have to get them like Drake's son at the, for their... I mean, like that's the thing that messes with me, not like any of those things. Like how do I keep them hungry in a world where I'm gonna provide them everything, where my heart wants to provide them everything and my head wants to provide them nothing?
06:36 Gerber: Which will win?
06:38 Vaynerchuk: My heart.