Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899

1. 0:00 – 4:01

   How did you get into investing and tech?

   1. HSHarry Stebbings0:00

      (beeping sound) Three, two, one, zero. (dinging sound) You have now arrived at your destination. Gary, this is such a joy to do. As I said to you beforehand, uh, seven years, uh, of me, uh, waiting, but I'm so thrilled that you joined me. So thank you so much for joining me today.

   2. GVGary Vaynerchuk0:18

      Thanks for having me, Harry. Glad to be on the show.

   3. HSHarry Stebbings0:21

      Not at all. I would love to start, before we dive into the real meat, just set some context. How did you make your way into the world of investing and tech first, before we dive into the meat?

   4. GVGary Vaynerchuk0:31

      You know, I never knew about investing. I, you know, I was ... When did I invest in Twitter? 2007. Um, I was 32 years old the first time I made an investment. I had never really even heard about angel investing. The world was very different back in 2006. Now, it is common practice. Most kids think about being an investor. You have 13-year-olds, you know, on Robinhood and NFTs. And so I was 32, I'd never thought about it prior, but I got into social media, Web 2.0, and I started to go to things like South by Southwest and this and that. I didn't have a lot of money, um, because I was working in my dad's liquor store and not getting paid a lot and all the, you know, the stories I talk about of, like, building a big business but not getting a lot of dollars. So I didn't have a lot of money, so when I first heard, like, "They put 100,000 into this. This guy put a million into..." I was like, "I don't... That's not for me. I don't have that kind of money." Then I started realizing, like, oh, you could write a $25,000 check, this, that, and the other thing. And then one thing led to another and I became very friendly with, you know, the- the f- several people on the small 10, 15, 20 person Facebook team, including their founding CTO, Blaine Cook. I started becoming friendly with Kevin Rose, uh, who is the founder of Digg.com and who's now very big in Web3 with Moonbirds. I, um, I started getting in the mix. I started reading TechCrunch, um, and I was like, "Oh, man. There's, like, this whole world." And then Blaine Cook called me and said, "I'm leaving Twitter and I'm really not happy and want to just sell all my shares. Just want to wipe my hands of it."

   5. HSHarry Stebbings2:07

      (laughs)

   6. GVGary Vaynerchuk2:07

      "And- and I know that you're a big believer, Gary, and you've been really nice to me and I think you- you get it bigger than just the way the nerds and I see it. And would you like to buy some of my equity?" And I said, "Yes, sir." First, I spent like five minutes trying to talk him out of it, um, but then I bought it. So it was my first transaction ever. I had to find a law firm in New Jersey. Um, I found one. The junior guy that was ascending to partner was a man by the name of Mark Yudkin. He now is the COO and my general counsel of my whole world. So from the first-

   7. HSHarry Stebbings2:41

      (laughs)

   8. GVGary Vaynerchuk2:41

      ... investment I ever made. Uh, several months later, Randy Zuckerberg called me and said, um, "Mark and I wanted to reach out. Our parents are sh- are selling, um, some of our s- their stock 'cause they wanna buy a house in California to be bi-coastal, to be near us. Would you like to buy Facebook stock?" I said, "Yes." Uh, that was the biggest check I'd ever written. Um, that was a six-figure check. It wiped pretty much all my savings out. And then finally, and by the way, that's, ironically, this is crazy, this is actually the certificates from Tumblr and Twitter of my investments. Then finally, in that same year, David Karp and I became friendly. He came to the Wine Library and I said, "David, I really want to invest in Tumblr. I think you're the next big thing." And the first three companies I invested in, in my entire life, as an investor, were Facebook, Twitter, and Tumblr. Tumblr sold for a billion dollars to Yahoo a couple years later. Facebook and Twitter obviously went IPO. I've never sold a share of Facebook since the day I invested, um, almost 15 years ago. And, um, I sold some Twitter, but still hold the majority of that holdings from then and, um. And then, you know, a year or two later, I started to make business content, not wine content, in 2009. I'd really established myself with a book called Crush It about social media, and now in 2009, '10, I was really part of that Silicon Valley Web2 thing

2. 4:01 – 7:35

   How much of a role does Luck play?

   1. GVGary Vaynerchuk4:01

      and away I went.

   2. HSHarry Stebbings4:02

      Can I ask you, and this is, I- I mean this not that you put yourself in those positions, but like I had Chris Sacca on the show and he said, "I may be lucky, but it wasn't by accident." Can I ask, when you look back to the first investments and when you actually think on the career, how much of a role do you think luck plays?

   3. GVGary Vaynerchuk4:18

      Luck plays a role in everything if you're willing to go there. So for example, I was born in the USSR.

   4. HSHarry Stebbings4:25

      Mm-hmm.

   5. GVGary Vaynerchuk4:26

      And communist Russia from 1917 till 1991 basically did not let people leave the country. A lot of people don't know this, but communist USSR was a jail. Unlike Iran, more like North Korea, you were not allowed to leave the country. And so I was born in 1975. In 1971 or 2, there was a political event that happened where some Russians tried to hijack a plane and go to Sweden to escape the country. It became a brouhaha internationally and Russia tweaked its rules and allowed people who were Jewish to go to Israel, and that's how they kind of calmed the geopolitical storm. I am Jewish. I was born in 1975, and in 1978 we won a lotto that a couple hundred thousand people won and were able to leave the Soviet Union and I grew up in America as an entrepreneur. I would argue that my entire life is luck in that scenario, 'cause otherwise I would have, had I not been Jewish or had that situation not happened, I would have probably come to America maybe when the Berlin Wall fell in 1991 and I would be a totally different human being.

   6. HSHarry Stebbings5:44

      Yeah.

   7. GVGary Vaynerchuk5:45

      So that is luck. Me working hard, staying curious, staying up late at night and not playing video games but reading the internet, finding out about social media, flying to London to go to Future of Web Apps to learn, going to South by Southwest to Texas to learn...... putting myself in a position to meet the companies that I personally thought were good, Facebook and Twitter and Tumblr, putting in the hours, providing value to those people so that I became a friend, not just somebody who was hanging around. Thinking, working, trying feels less luck, but when people use luck or talk about timing and things of that nature, of course. I could have been born in the '20s, my parents could have never met and I'd never even been a human being. Everybody is lucky and nobody's lucky. It just depends on deciding what you want to say and do. But as far as, like, the strategy, I feel incredibly comfortable in saying saving my money in my 20s and then deciding to spend all of it in a one-year period on Facebook, Twitter, and Tumblr, based on, at that point, 10 years of very hard work, diligence, of saving and not wasting my money, and looking for the opportunity to strike, doesn't feel as oriented towards luck as it does towards being thoughtful with the gifts I was given, which could be luck. And this is the point of it all.

   8. HSHarry Stebbings7:21

      Now, I've listened to pretty much every, uh, episode that I could find, um, which means I've done a lot of walking over the last few days, of your interviews.

   9. GVGary Vaynerchuk7:28

      Mm-hmm.

   10. HSHarry Stebbings7:29

       And I wanted to really ask questions that other people haven't done. Um, and so-

   11. GVGary Vaynerchuk7:33

       Please.

   12. HSHarry Stebbings7:33

       ... I wanted to start with a tough one, which was

3. 7:35 – 13:54

   What's the most difficult but valuable lesson you've learned?

   1. HSHarry Stebbings7:35

      difficult times bring about very important lessons. What's the most difficult but valuable lesson that you've learned?

   2. GVGary Vaynerchuk7:43

      The most difficult lesson was when me and my dad started to have friction in my late 20s, early 30s. From 22 to 29, I didn't even question why my dad wasn't paying me much, even though I blew up his business. I didn't question why my dad wasn't interested in giving me some equity, even though I blew up his business. And just for everybody who's listening who doesn't know anything about my story, my dad had a business doing 3.8 million in revenue and in a seven-year window, I took it to 60 million, and I changed the course of my father's financial life and my mother's financial life, yet I was never getting paid $100,000 a year and owned nothing, and I was the operator. And so when I kind of got to, like, an age where I felt like I was growing up and thinking about, like, "Maybe I should buy a house or an apartment, maybe," you know, 'cause I was blindly like, "I'm gonna help my parents." So when I started asking questions, the answers were not of the kind that I was hoping for.

   3. HSHarry Stebbings8:45

      How did you take that? Is it, I mean, when it's your father-

   4. GVGary Vaynerchuk8:48

      I took it very poorly. It was very difficult. You know, you sit there and you're like, "I'm..." You know, uh, the reason I was willing to do what I did was 'cause my father built the base, but I was sitting there and said, "I've been bleeding seven days a week the last eight years. I've..." Like, the math is the math, like, "This is how much it did before I took over. Look what's happened. Everything's different. Um, everyone's life is better. My brother's life is better, my sister's life is better, my parents' life is better. My life is fine, but, like, I'm definitely not getting my fair shake." I assumed the conversation was gonna be really easy. Aren't I the 50/50 partner at least? I more than 20X'd the company. And the answers were no. The answers were, "You'll get it when I die." I'm like, "Well, you're, you've got good genes and you're only 22 years older than me. I'm not sure I want to inherit this business when I'm 70." Um, and, and it was a challenge. Now, I was empathetic, which helps. I under- I could understand where my father was coming from. He was in immigrant land, not in startup land, not in America land. He was old country. He was like, "It's the family business and when the dad dies, the son takes over, the daughter." And, like, and so I understood, but it was very, very challenging. Not to mention that he was in charge of building the new store, he was the general contractor of this new store, which was two years behind and five times over budget. So on top of everything else, I'm frustrated with him 'cause I don't think he's delivering the promise that I'm delivering, and that's putting a lot of pressure on me. When you're going over budget that much and you're trying to pay for shit, you're scared. So it was a very trying time that I don't talk about often, and I'm only doing this 'cause I feel like you put in so many hours that I, I feel compelled. Plus I don't do it because I don't wanna paint the wrong picture. My dad's the best. It was just what it was. And so those were long nights. That was the first time. And what I learned from it was what I preach, which is fuck money, business doesn't mean shit. Your family, life, happiness. And I am proud to say I was the bitter- bigger man, that I feel like I had plenty of opportunities to turn it into a much more contentious, negative situation, and instead what I did was I built infrastructure around myself, made myself capable of moving on at some point without detrimenting the business. My father also would tell you if he was on, he'd be like, "Cool. That's Gary's problem. Let me tell you what my problem was. I came to America and had nothing. I built this business. Yes, my son came and crushed it, but yes, I was maybe winning financially more than he was, but I had lost my identity. I went from being Sasha, the man at Shoppers Discount Liquors and Wine Library, to the people I'd been doing business with for 20 years wouldn't even return my call 'cause everyone knew Gary was running shit and Gary was the guy, and I'm, and I'm..." L- my dad's only 22 years older than me, so when I'm the man at 24, and I was, my dad was 46. To remind everybody listening, I'm 46 right now. So my 46-year-old father who's an alpha, who's prideful as they come, is now walking around, and he would always use this Russian term and it would translate to a senator with an empty briefcase, and what that meant in Russia talk was in that briefcase was cash to get shit done.

   5. HSHarry Stebbings12:06

      (laughs)

   6. GVGary Vaynerchuk12:06

      He was a senator...Yeah, he owns it, but he has an empty briefcase that nobody's fucking talking to him, and it killed him inside. So luckily for us, which is why I can talk about it openly, there was a moment there where I think he wanted to be the man again, and I needed to build something for myself. My brother was 11 years younger, coming out of school, and 2009 just kinda really worked out. And at 34 years old, I started VaynerMedia with no money. We started the company in Buddy Media's conference room, which I'm sure you know, 'cause you've listened to him on our interviews. And I'm very proud of what we built from zero and scratch with no cash, and, um, and it's fun.

   7. HSHarry Stebbings12:46

      Did that experience, did that experience impact how you think about bringing up, encouraging your children today, the words you use, how you incentivize them? How-

   8. GVGary Vaynerchuk12:54

      You know, it's funny, I, I... Yes, but more of how I encourage all of you.

   9. HSHarry Stebbings12:59

      Huh.

   10. GVGary Vaynerchuk12:59

       You know, what I know about my kids, even at this age is they're still forming who they are, but, you know, there's a, there's a high propensity that my ki- children are not going to be as interested in being a pure... I don't think my children are pure bred entrepreneurs the way I was. They're different, and that's amazing. I want people to be who they are. I don't want them to be like me. So I think it's impacting more of how I'm teaching the world, more so than my own children, 'cause my children are individual people that have their thing. I think I'm speaking from a perspective of experience within a arena that resonates with a lot of people, and that's why I think I'm such a prolific content creator, 'cause I like people to win, 'cause I think people winning doesn't come out of my winning. It's a nice feeling. I think the world doesn't have enough people who are deploying good into it, and I'm passionate about that.

4. 13:54 – 16:29

   What is your greatest insecurity?

   1. GVGary Vaynerchuk13:54

   2. HSHarry Stebbings13:54

      When I listen to so many of your shows, and when I listen to you now, the thing I get is like security. The w- the wisdom comes through and the assuredness comes through, and bluntly, it never sounds like you have self-doubt or insecurity when I was listening, and I was just intrigued. What... Everyone's insecure and doubtful of themselves in some way.

   3. GVGary Vaynerchuk14:12

      I, yeah-

   4. HSHarry Stebbings14:12

      How do you ... not

   5. NANarrator14:13

      ... yourself and how are you-

   6. GVGary Vaynerchuk14:14

      I'm incredible... Yeah, I love that question. I'm... The reason you see that is that when I stay in the arena of business, there is something pretty crazy. I am a little scared. Thank God, Kobe Bryant and some of the, you know, I don't wanna bring up Jordan and Tom Brady 'cause I hate them so much as Jets and Knicks fans, but-

   7. HSHarry Stebbings14:33

      (laughs)

   8. GVGary Vaynerchuk14:33

      ... thank God, there's some of these athletes out there that I can look at and be like, "Uh-huh, that." Like, when I tell you, for anybody who loves Kobe Bryant, I think there's a pretty good understanding, including a documentary I saw this week that talked about when he was... Oh, it was actually a book I read, uh, which is rare for me, but I read a book about the '90 Knicks, the '90s era New York Knicks, and they... There's a little piece they talk about Kobe coming in working out, and they talked about him being 17, 18 and feeling like he was 48 with no doubt. And that, that's who I've been as an entrepreneur. No question. To answer your question directly, I have many parts of my life where I have doubt. I had a lot of doubt as, like a teenager and in my 20s around, like asking girls out. My, my confidence level in, like girlfriend/boyfriend, like school stuff wasn't at the same level as business. I have... This one's a wild one. I have incredible fear of reading out loud 'cause I'm terrible at reading.

   9. HSHarry Stebbings15:32

      Huh.

   10. GVGary Vaynerchuk15:32

       Literally, at the Passover table, reading passages frightens me amongst my family, but I can go give a improv keynote to seven billion people on Earth right now if there was a stage for the entire wor- Literally, if tomorrow, they're like, "There's this new stage and it simulcasts to every person on Earth, and you can submit for slots, and you get a, to give a 15-minute keynote to the world," I would literally submit for a keynote immediately.

   11. HSHarry Stebbings15:58

       (laughs)

   12. GVGary Vaynerchuk15:58

       If I had to do it right now, Harry, if you're like, "Actually, Gary, I'm a genie from the future and I can do that if I snap my fingers, you will have to be on stage right now, and every person on Earth is listening to you talk," I would do it right now. Yet, reading a children's book to every, to you and Andrew right now in my office would shu- would scare me. So I have insecurities. I'm a human being, but I have none when it comes to being an entrepreneur, and I'm not kidding. Like, (laughs) I'm not kidding. I'm really not scared.

5. 16:29 – 17:00

   Has your fearlessness ever gotten you into trouble?

   1. GVGary Vaynerchuk16:29

   2. HSHarry Stebbings16:29

      Has that ever got you in trouble? It's got me in trouble when I've not-

   3. GVGary Vaynerchuk16:33

      It ha- It hasn't, it hasn't gotten me in trouble because my lack of fear is also balanced with extraordinary levels of empathy and compassion to the other parties involved in my behaviors.

   4. HSHarry Stebbings16:46

      Hmm. You know, it's like you said-

   5. GVGary Vaynerchuk16:48

      Right? The reason, the reason I was such a class clown and disruptor in class, but adored by my teachers was I knew how to walk the fine line of not disrespecting them while still doing my shenanigans.

   6. HSHarry Stebbings16:59

      (laughs)

6. 17:00 – 19:24

   Public Gary vs. Private Gary

   1. HSHarry Stebbings17:00

      You said about speaking to the world in one sitting. Uh, there's public Gary and there's private Gary, or there's public Harry and there's private Harry, especially for me. I struggle with this identity friction between the two. Do you have the identity chasm between what the world sees and who you actually are when you're sitting with your kids and a bowl of popcorn?

   2. GVGary Vaynerchuk17:22

      I am pretty much what you get. Somebody should... Who said that to me just now? Oh, I was just talking to a gentleman who worked for us for four years, four hours ago. Let me look at the clock. Four hours ago. It was an exit. It, uh, uh, the way you dream it up when you're the kind of entrepreneur I am, this was purely like, "I love you, I thank you, and I'm here for you." And that person saying, "I love you, thank you. It was perfect. I can't even say anything bad in four years. This was a better financial, bigger opportunity." I'm about to hang up, he goes, "Hey." Okay, and we didn't interact a lot. I did interview him four years ago and hired him, but we didn't interact a lot after. He goes, um, "Could I just say something?" I'm like, "Of course. What, what's up?" He said, um, "You know, you've gotten really popular (laughs) and known since I've worked here." He goes, "I'm probably asked 13 times a day, and I only know like 15 people." Uh, this is his whole shtick of...... "What's Gary really like?" And he goes, "It's really cool to tell those people, whether they're cynical or they're major fans, that he's exactly what you see." I am who I am in the context professionally, behind the scenes with my team at F Vayner that you see. To your point of, like, who am I as, like, a brother, as a son, in- in my personal life, I'm contextually who I am there. But obviously, that's a different human being. But it's not like I'm a dick face or I'm reserved. I'm high energy, I'm kind, I'm pumped. It just formulates differently. It's like, "Let's go to the park," or, "Let's watch TV." And by the way, on the flip side, you know, depth is really just more of, like, sometimes it's not watch TV or, like, go to the park, it's actually just sitting and talking. I love doing that. Um, but, you know, it's very easy for me to reconcile the public output of content versus the things I wanna keep private. And, uh, it's very important for me that my personal life is extremely private. Like, extremely private. I don't share anything about

7. 19:24 – 22:00

   How do you manage your ego?

   1. GVGary Vaynerchuk19:24

      it.

   2. HSHarry Stebbings19:24

      Can I ask, you said about kind of becoming very big, as you are now. When you started becoming very big, was ego management a challenge? It's really hard. Suddenly the world wants you and you're like, "Shit."

   3. GVGary Vaynerchuk19:37

      I- I... don't believe in my hype, which is what allows me to not believe in the hate thrown towards me, which is the natural thing that happens when you get popularity and success as well. So, it was actually very easy for me, Harry. Like, it was funny, I was with my college friends who I haven't been able to spend a lot of time with since I left, 'cause I've been working every minute and everyone's around the country, and they were at V Con. And it was just so awesome, like, they were so pumped. And all of them, these are like 46 to 48-year-old men, every one of them, and they, and these are thuggy, like, my friends from college are from the hood, for lack of a better word. They were all b- one by one were really nice and emotional with me, like, teary moments. One by one, there was about five of them there, different times, one called after the event, two during there, one at night, during one in the breakfast. They just tell you, like, "It's really cool that you are literally, literally, actually, actually exactly the same." And for me it was, like, very flattering, but, like, very easy. And I'll tell you why. This is all DNA. All that money and fame do, Harry, is exposes who you actually are. It just accelerates your truth. You know, to me-

   4. HSHarry Stebbings20:58

      What if you don't-

   5. GVGary Vaynerchuk20:59

      ... just because of all that-

   6. HSHarry Stebbings20:59

      What if you don't like who you actually are and opening up-

   7. GVGary Vaynerchuk21:02

      Well, if you don't like who you-

   8. HSHarry Stebbings21:03

      ... by-

   9. GVGary Vaynerchuk21:03

      Yeah. If you don't lo-... Yeah.

   10. HSHarry Stebbings21:05

       Yeah.

   11. GVGary Vaynerchuk21:05

       If you don't like who you... Yeah. I mean, that's... What do you think? Why do you... I mean, think about my content. My content is far more therapy than it is business, HBS str-... Like, this is all about self-esteem. Harry, this is all about self-esteem, and one of the reasons I tell everybody things, I try both things, I'm like, "You have..." Like, "Don't..." Like, I try, I try to get people to self-love themselves for, like, just asking them, "What's the alternative?" Or I love saying things, "Remember, if you think you suck, somebody put that in your head." Like, you didn't come out of the womb and be like, "I suck." You think you suck 'cause your mom told you you suck. You think you suck 'cause your dad told you you suck. Like, that's... And then I try to get people to, like, reconcile that. And then I try to remind them that everybody else sucks too, so why are you beating yourself up? Self-love is... I'm almost using business as a disguise to try to help people

8. 22:00 – 24:51

   How to deal with the haters

   1. GVGary Vaynerchuk22:00

      be happier.

   2. HSHarry Stebbings22:01

      What would you advise me? I get a ton of DMs, comments, "I hate you." "You're a prick."

   3. GVGary Vaynerchuk22:08

      (laughs)

   4. HSHarry Stebbings22:08

      Or, "You don't deserve it." "You're young," "You're rich," wha- whatever. And like, horrible messages. Some death threats even, in the past. Like, and it really upsets me. Like, I cry, I will be very sad. What would you advise me to not feel like-

   5. GVGary Vaynerchuk22:22

      I would... Well, there's a couple things. First I would ask you, is how much, if any, of it resonates with you as truth?

   6. HSHarry Stebbings22:29

      Not at all. It's, they don't know me. Just random people.

   7. GVGary Vaynerchuk22:32

      Well, that... Then you, then you're really in a good place. Like, for me, one of the things I've liked about pushback, hate, negativity, is, I- I start with humility. Is there anything here? Can I take 2% out of... You know, "Gary, you're a fucking asshole." It's very hard to take something out of that.

   8. HSHarry Stebbings22:53

      (laughs)

   9. GVGary Vaynerchuk22:53

      But sometimes I'll reply and be like, "I'm really sorry that I trigger this." Like, we... And, like, you can, like, talk about it. "Well, you- you- you think you know everything." I'm like, "No, no. I'm passionate and have conviction," which, yes, can come across in video and audio that way, but rest assured, I don't know shit about 99% of shit in the world. I'm just staying in my very narrow lane (laughs) of, like, sports and wine and market. Like, this is tiny. I don't know anything about a million things. That's why I don't talk about brain surgery, it's why I don't talk about meditation, it's why I don't talk about a million things. So, there's that. So firstly, start with humility. Then I start with compassion. Harry, if somebody acts... And I know you've heard this in my content, 'cause I talk about it all the time. I do think having some compassion for those people. Bro, it sucks to live a life where you actually wanna tear someone else down. It means you're really unhappy. And you should just be happy that your life isn't about sitting around finding someone on YouTube or Twitter or Instagram and sending them a nasty DM. I really go with empathy and, like, accountability. I'm like, "I- is there anything right? Are they right? Am I getting, uh, too high on my own supply?" B, "Man, I really feel bad that this is what they wanna spend their time on." C, (sighs) deep breath, reset. Like, there's 99% of the people, e- 86% of the people that are thrilled and it's going well. Let me focus on consuming positivity-One of the biggest things that drives me today here, is that the world speaks about so much negativity that I feel a requirement to talk about positivity, because what one consumes is who they become. And I'm very proud of my practical optimistic framework. I'm optimistic, but I'm not delusional and I'm not creating foofy, foofy eighth place trophies. It's like, "Hey, this is real shit, but we can do this nicely," and I, I beat that drum very aggressively.

   10. HSHarry Stebbings24:50

       You said about

9. 24:51 – 27:24

   How to balance work and family

   1. HSHarry Stebbings24:51

      where you spend time, and I'm using this for just pure therapy session now. Um, how do you not lose an inch on performance work-wise, but also are a great brother or a great father? How do you not lose an inch and then-

   2. GVGary Vaynerchuk25:04

      By, by easy, easy, because I don't judge within short fr- time frames.

   3. HSHarry Stebbings25:09

      Expand. What do you mean? (laughs)

   4. GVGary Vaynerchuk25:12

      This is gonna really... You're gonna like this one.

   5. HSHarry Stebbings25:13

      Good.

   6. GVGary Vaynerchuk25:13

      The reason I don't struggle by losing my edge or being a killer by allocating time to personal endeavors, time with family or escapism is because I don't judge my success or giving up an inch in the time frame of a week, a month, or a year. I am incredibly ambitious, but the frame of timing that I put my hopes and wants and dreams of my accomplishments is for the length of my life, not this month. So, if the next four days I don't wanna do anything, it's just four days in a 99-year life.

   7. HSHarry Stebbings25:55

      Can I ask, is that, is that the result though of many years of success and finances being built up? Were you the same a year younger?

   8. GVGary Vaynerchuk26:02

      No, it's the rev- it's the reverse. L- listen back to the interview. How the hell do you think I ever did the thing I did in the first place for my parents? I gave up my 20s for them, because at 22, at 22 I was like, "I'm gonna do this for eight years." I used to think about 30 a lot. "I'm gonna do this for eight years, just give to my folks, not give a fuck. Fuck it, I'll figure it out after 'cause I've got 30 to 99."

   9. HSHarry Stebbings26:27

      Did you find it hard having to grow up so much faster than everyone else at 22?

   10. GVGary Vaynerchuk26:32

       I didn't know the difference. I didn't know that I was growing up faster. I didn't realize that my dad was gone all the time and thus I was the oldest son from the old country and I was the father figure to my sister and brother. I didn't realize that I was 14 and working 14 hours a day, and that's probably not normal. We were such immigrants in our cocoon, I just didn't even know. And I also grew up in blue-collar... Like, I didn't grow up... Like, all my friends worked at A&P making six bucks an hour. I grew up in... I didn't grow up in affluence. So me working a lot, it wasn't like my friends were going to sleepaway camp or, like, Ibiza or the Hamptons. I... Everybody else was kind of doing... either sitting at home and being a good student or working at fucking McDonald's. You know what I mean? So, I wasn't in an environment where I felt like it was... I mean, I was the most extreme of everybody, but I also loved it. I love being a businessperson.

   11. HSHarry Stebbings27:22

       That realization causes

10. 27:24 – 30:33

    How do you know when to give up?

    1. HSHarry Stebbings27:24

       you to make a decision. You've said before that changing your mind is a strength. How do you know when to give up on something-

    2. GVGary Vaynerchuk27:31

       Yes.

    3. HSHarry Stebbings27:31

       ... versus when to persist and fucking nail it?

    4. GVGary Vaynerchuk27:35

       Love that question. I like giving up on something when I no longer like it, regardless of the financial outcome.

    5. HSHarry Stebbings27:42

       Huh.

    6. GVGary Vaynerchuk27:45

       I just... I try to capitalize against being content, satisfied, and happy, not maximizing the financial aspect of the situation at hand.

    7. HSHarry Stebbings27:54

       Does everything have a price?

    8. GVGary Vaynerchuk27:56

       And that, and that, and that... Um, I'll answer that one in a minute. And that is the reverse of what people think. To your question earlier, most people think this mindset and who I am comes because I have money, back to my college friends. I have money because I had the mindset when I had no money.

    9. HSHarry Stebbings28:13

       (laughs)

    10. GVGary Vaynerchuk28:15

        It's the reverse. I knew that I was happy at 25 making $48,000 a year, buying nothing, so I could be happy forever, so who gives a fuck? 'Cause making a million bucks wasn't gonna be my happiness radar. And yes, everything has a price.

    11. HSHarry Stebbings28:31

        (laughs)

    12. GVGary Vaynerchuk28:31

        There's not a... Everything does have a price, because the reality is... Well, it's a funny game. Like, you know, it's funny as I'm answering how I'm thinking about this. I'll give you an example. I'm answering yes, everything has a price, 'cause in reality I believe that, but I just thought of something. If somebody came to me and said, "I will give you $100 billion in cash, but you can never work again. You must fully retire, meaning the cliché thing, must go on a beach in a very nice place and actually do nothing besides drink beers, walk on the beach, look at the sunset, fish. We'll give you fishing," which I like. Kind of fun here and there, right? I would not take that. I would not take that. That would break my soul. I would die. You know how sometimes people lo-... You know, this is gonna land for you, and Andrew's in the background here. You know when you see, like, an 80-year- eight-year-old person lose their spouse and they die, like, a week later? And you're like, "Grandpa died of a broken heart. He couldn't live without Grandma, but he was perfectly fine a week before." There's a part of me that actually believes that I have that with work.

    13. HSHarry Stebbings29:42

        Can I ask you-

    14. GVGary Vaynerchuk29:43

        That I ca-... I'm sorry?

    15. HSHarry Stebbings29:44

        Do we have a hard stop? I just want to be respectful of your time.

    16. GVGary Vaynerchuk29:47

        We had a hard stop, uh, I think seven minutes ago, but I'm enjoying the shit out of this. Um, I really believe that, and I know businesspeople who stay very active. I just... I've said this often, and means you've heard it 'cause you've consumed a lot. It is my great hobby. Whatever anybody loves the most... Everybody listening, whatever you love the most, skiing, sailing, fishing, basketball, uh, traveling, uh, Frisbee, beer making, um, watching movies, whatever it is, whate- like, everyone listening and watching, stop, tell me the number one thing you like more than anything in the world. For me, that is being an entrepreneur.

    17. HSHarry Stebbings30:28

        I wanna do three quick, quickfire questions. They're under a minute each, so we'll get it done. First one

11. 30:33 – 31:05

    What have you recently changed your mind on?

    1. HSHarry Stebbings30:33

       is, what have you recently changed your mind on, Gary?

    2. GVGary Vaynerchuk30:37

       Ooh, that's a great question. What have I res- I changed my mind on how big of a platform Facebook is. One of the coolest things for me right now is that I'm back into being obsessed with content on Facebook, 'cause the math of supply and demand of attention on it has flipped aggressively with the iOS 14 update and everybody kind of going away from it spending ads, but yet still there's a lot of people consuming it. So, the most recent thing is very narrow. It is my content strategy on Facebook.

    3. HSHarry Stebbings31:04

       I mean,

12. 31:05 – 31:20

    What is your greatest accomplishment?

    1. HSHarry Stebbings31:05

       there's an episode in that, to be fair. Um, what's the greatest accomplishment of your life, in your mind?

    2. GVGary Vaynerchuk31:14

       That I am exceedingly liked by the far majority of people I've ever interacted with.

13. 31:20 – 32:20

    Where do you want to be in five years?

    1. GVGary Vaynerchuk31:20

    2. HSHarry Stebbings31:20

       Final one for you. We do this in five years' time. Where do you want Gary V to be then?

    3. GVGary Vaynerchuk31:28

       Hopefully in the same exact spot he is right now, which is not anxious about the health and well-being of anybody that he loves, meaning nobody is terminally ill, and doing what he wants to do every day professionally.

    4. HSHarry Stebbings31:41

       Gary, listen, I've n-

    5. GVGary Vaynerchuk31:43

       Whether that's the mundane... I'm sorry if you're... Like, I know you're going for the big close, but I just want everybody to hear this. Me doing what I wanna do every day means I'm doing plenty of things every day I don't want to be doing in the micro, right? There's a... The- the next meeting, the this, this fire. But in the macro, I'm playing the game. I'm the captain of this ship and on sunny days I get to enjoy it, and when the storm hits and our boat might tip over, I've gotta have my hands on the wheel and I've gotta fix it. That's where I wanna be forever.

    6. HSHarry Stebbings32:12

       Gary, this has been amazing. You are a hero. I so appreciate the time and honestly thank you so much.

    7. GVGary Vaynerchuk32:18

       Thanks, Harry.

    8. HSHarry Stebbings32:18

       Stay safe.

    9. GVGary Vaynerchuk32:19

       Cheers.

Episode duration: 32:20