The Exchanges

Q Can I ask you, and this, I, I mean this, not, you put yourself in those positions, but like, I had Chris Sacker 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?

A Luck plays a role in everything if you're willing to go there. So for example, I was born in the USSR 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 two, 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 like calmed the geopolitical storm. I am Jewish. I was born in 1975 and in 1978, we won a lotto that a couple 100,000 people won and we're 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 that 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. 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 le…

AI assessment note: “Luck plays a role in everything if you're willing to go there.”

Q Can I ask you, and this, I, I mean this, not, you put yourself in those positions, but like, I had Chris Sacker 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?

A Luck plays a role in everything if you're willing to go there. So for example, I was born in the USSR 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 two, 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 like calmed the geopolitical storm. I am Jewish. I was born in 1975 and in 1978, we won a lotto that a couple 100,000 people won and we're 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 that 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. 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 le…

AI assessment note: “Luck plays a role in everything if you're willing to go there.”

Q I've listened to pretty much every episode that I could find, um, which means I've done a lot of walking over the last few days of your interviews, and I wanted to really ask questions that other people haven't done. Um, and so I wanted to start with a tough one, which was difficult times bring about very important lessons. What's the most difficult but valuable lesson that you've learned?

A The most difficult lesson was when me and my dad started to have friction in my late twenties, early thirties. 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 sixty million. And I changed the course of my father's financial life and my mother's financial life. Yet I was never getting paid a 100,000 dollars 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 going to help my parents. So when I started asking questions, the answers were not of the kind that I was hoping for.

AI assessment note: “The most difficult lesson was when me and my dad started to have friction”

Q How did you take that? Is it, I mean, when is your father?

A I took it very poorly. It was very difficult. You know, you sit there and you're like, I'm, you know, the reason I was willing to do what I did was because 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 going to be really easy. Aren't I the fifty-fifty partner at least? I'm more than 20 X 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 understood. I could understand where my father was coming from. He was an 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 c…

AI assessment note: “I took it very poorly. It was very difficult.”

Q How did you take that? Is it, I mean, when is your father?

A I took it very poorly. It was very difficult. You know, you sit there and you're like, I'm, you know, the reason I was willing to do what I did was because 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 going to be really easy. Aren't I the fifty-fifty partner at least? I'm more than 20 X 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 understood. I could understand where my father was coming from. He was an 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 c…

AI assessment note: “I took it very poorly. It was very difficult.”

Q Did you find it hard having to grow up so much faster than everyone else at 20?

A 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 sleep away camp or like a visa 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 loved being a business person.

AI assessment note: “I didn't know the difference. I didn't know that I was growing up faster.”

Q Did you find it hard having to grow up so much faster than everyone else at 20?

A 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 sleep away camp or like a visa 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 loved being a business person.

AI assessment note: “I didn't know the difference. I didn't know that I was growing up faster.”

Q I've listened to pretty much every episode that I could find, um, which means I've done a lot of walking over the last few days of your interviews, and I wanted to really ask questions that other people haven't done. Um, and so I wanted to start with a tough one, which was difficult times bring about very important lessons. What's the most difficult but valuable lesson that you've learned?

A The most difficult lesson was when me and my dad started to have friction in my late twenties, early thirties. 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 sixty million. And I changed the course of my father's financial life and my mother's financial life. Yet I was never getting paid a 100,000 dollars 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 going to help my parents. So when I started asking questions, the answers were not of the kind that I was hoping for.

AI assessment note: “The most difficult lesson was when me and my dad started to have friction”

Q Well, 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, I, I,

A Don't believe in my hype, which is what allows me to not believe in the heat 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 these are thuggy, like, my friends from college are from the hood, for lack of a better word. They were all, 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, one in the breakfast. They just, 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, just because-

AI assessment note: “So it was actually very easy for me, Harry.”

Q I would love to start on 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?

A 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 thirteen-year-olds, you know, on Robinhood and NFTs. And so I was 32. I never thought about it prior, but I got into social media, web two point O 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, 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 a 100,000 into this, this guy put a million and I was like, I don't know, 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 dollar check. This, that and the other thing. And then one thing led to another, and I became very friendly with, you know, the, the several people on the small 1015, 20 person Facebook team, including their founding CTO, Blaine Cook. I started becoming friendly with Kevin Rose, uh, who was the founder of dig.com and was now very big in web three with Moonbirds. I, um, I s…

AI assessment note: “I got into social media, web two point O and I started to go to things”

Q Well, 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, I, I,

A Don't believe in my hype, which is what allows me to not believe in the heat 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 these are thuggy, like, my friends from college are from the hood, for lack of a better word. They were all, 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, one in the breakfast. They just, 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, just because-

AI assessment note: “So it was actually very easy for me, Harry.”

Q You said about speaking to the world in one sitting. 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 in a bowl of popcorn?

A I am pretty much what you get. Somebody said, 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. Four hours ago. It was an exit. 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, 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 you say something? I'm like, of course. What's up? He said, um, you know, you've gotten really popular 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 a Vayner that you see to your point of like, who am I as like a brother, as a son in my personal life? I'm contextually who I am there, but obviously that's a different human being, but it's not like, um, a dick face or I'm reserved. I'm high energy. I'm kind. …

AI assessment note: “I am pretty much what you get.”

Q When I listen to so many of your shows, and when I listen to you now, the thing I get is, like, security. The wisdom comes through, and the assuredness comes through, and 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. How do you doubt yourself?

A 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 want to bring up Jordan and Tom Brady because I hate them so much as Jets and Knicks fans, but 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 90 zero New York Knicks, and they, there's a little piece they talk about Kobe coming in, working out, and they talked about him being 1718, 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've dealt. I had a lot of doubt as like a teenager and in my twenties 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. Literally at the Passover table, reading passages frightens me amongst my family,…

AI assessment note: “To answer your question directly, I have many parts of my life where I've dealt.”

Q When I listen to so many of your shows, and when I listen to you now, the thing I get is, like, security. The wisdom comes through, and the assuredness comes through, and 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. How do you doubt yourself?

A 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 want to bring up Jordan and Tom Brady because I hate them so much as Jets and Knicks fans, but 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 90 zero New York Knicks, and they, there's a little piece they talk about Kobe coming in, working out, and they talked about him being 1718, 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've dealt. I had a lot of doubt as like a teenager and in my twenties 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. Literally at the Passover table, reading passages frightens me amongst my family,…

AI assessment note: “I have incredible fear of reading out loud cause I'm terrible at reading.”

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

A You know, it's funny. I, I, yes, but more of how I encourage all of you. 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 children are not going to be as interested in being a pure, I don't think my children are purebred 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, because my children are individual people that have their thing. I think I'm speaking from a perspective of experience within an arena that resonates with a lot of people, and that's why I think I'm such a prolific content creator, because I'd like people to win, because 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.

AI assessment note: “impacting more of how I'm teaching the world, more so than my own children”

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

A You know, it's funny. I, I, yes, but more of how I encourage all of you. 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 children are not going to be as interested in being a pure, I don't think my children are purebred 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, because my children are individual people that have their thing. I think I'm speaking from a perspective of experience within an arena that resonates with a lot of people, and that's why I think I'm such a prolific content creator, because I'd like people to win, because 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.

AI assessment note: “it's impacting more of how I'm teaching the world, more so than my own children”