20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it was Good to Learn Them, Why You Have to Change the Timeframe You Have For Success, His Relationship to Money and How it Has Changed Over Time & His First 3 Angel Investments; Twitter, Fa

Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia and the Creator & CEO of VeeFriends. Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34 million followers and garnishes over 272 million monthly impressions/views across all platforms. He is also a five-time New York Times Best-Selling Author and is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. If this was not enough, Gary serves on the board of GymShark, MikMak, Bojangles Restaurants, and Pencils of Promise. In Today’s Episode with Gary Vaynerchuk We Discuss: 1.) From Wine Library to One of The Great Angels in Tech: How did Gary make the transition from scaling the wine library to $60M in revenue to angel investing in Twitter, Facebook and Tumblr? To what extent does Gary think luck plays a role in one's success today? What are Gary's biggest lessons from having FB, Twitter and Tumblr as his first investments? How has his style of angel investing changed over time? 2.) Hard Lessons Learned and Insecurity: What is the most painful lesson Gary has learned that he is also pleased to have learned? How did Gary's relationship with his father impact how he engages with his children as a father today? What are Gary's biggest insecurities today? How does he try and combat them? What works? 3.) Money and Success: How does Gary evaluate his relationship with money today? How has it changed over time? Why does Gary believe that most people think too short-term? What can one do to inspire a more long-term mindset to building? Does Gary believe that everything has a price? What is the one thing for Gary that does not have a price? 4.) Resource and Time Allocation: How does Gary determine the projects to do vs not to do? How does Gary know when to quit a new project? How does Gary advise founders on when something is not working and knowing when to quit? What are some of the biggest mistakes Gary sees founders make when it comes to resource allocation in the early days?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome to 20 VC and I could not be more excited for this episode today. Our guest is just incredible. I have one real desire with this episode though. I wanted it to be content that's never been heard before or told by this guest on another show. I wanted to ask questions that no one's ever asked and it led to the most genuine, authentic and honest discussion. So with that, welcome Gary Vaynerchuk, serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and creator and CEO of V Friends. Gary is a content machine and documents his life as a CEO daily through his social media, which have over 34 million followers and over 272 million monthly impressions across all platforms. He's also a five-time New York Times bestselling author and is a prolific angel investor

• 0:43Harry Stebbings?

  with early investments in the likes of, check this out, Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, Uber. If that wasn't enough, Gary's also on the board of Jimm Shark, Mick Mack, Bojangles Restaurants and Pencils of Promise. And again, a huge thank you to Gary. He was incredibly open and it made this show so much more special. But before we move into the episode today, if you are a venture capitalist or corporate strategist, I want to tell you about Tegus. Tegus is the only company in the world that aggregates qualitative information on private companies from seed stage to pre-IPO. With Tegus, you can access other VCs and founders' expert call transcripts from previous rounds to help source fast-growing companies, create compelling emails to get a founder's response

• 1:25Harry Stebbings?

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• 2:07Speaker 01

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• 2:10Harry Stebbings?

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• 2:54Harry Stebbings?

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• 3:40Speaker 01

  You have now arrived at your destination.

• 3:43Harry Stebbings?

  Gary, this is such a joy to do. As I said to you beforehand, seven years of me waiting, but I'm so thrilled that you joined me. So thank you so much for joining me today.

• 3:52Speaker 02

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

• 3:54Harry Stebbings?

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

• 4:03Speaker 02

  I never knew about investing. I was 32 years old the first time I made an investment. I'd 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 never thought... 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 because I was working in my dad's liquor store, not getting paid a lot and all 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 hundred thousand 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

• 4:48Speaker 02

  several people on the small 10, 15, 20 person Facebook team, including their founding CTO Blaine Cook. I started becoming friendly with Kevin Rose, who was the founder of Dig.com and who's now very big in web 3 with Moonbirds. I started getting in the mix and I was like, "Oh, man, there's like this whole world." And then Blaine Cook called me and said, "I'm leaving Twitter. I'm really not happy and want to just sell all my shares. Just want to wipe my hands of it." And I know that you're a big believer, Gary, and you've been really nice to me and I think 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, but then I bought it. So it was my first transaction ever. I had to find a law firm in New Jersey. The junior guy that was ascending to partner was a man by the name of Mark Yudkin.

• 5:33Speaker 02

  He now is the COO and my general counsel of my whole world. So for the first investment I ever made. Several months later, Randy Zuckerberg called me and said, "Mark and I wanted to reach out. Our parents are selling some of their stock because they want to buy a house in California to be bi-coastal, to be near us. Would you like to buy Facebook stock?" I said, "Yes." That was the biggest check I'd ever written. That was a six-figure check. It wiped pretty much all my savings out. 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 were Facebook, Twitter and Tumblr. Tumblr sold for a billion dollars to Yahoo. Facebook and Twitter obviously went IPO. I've never sold a share of Facebook since the day I invested almost 15 years ago.

• 6:17Speaker 02

  I sold some Twitter, but still hold the majority of that holdings. And then 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 web 2 thing and away I went.

• 6:33Harry Stebbings?

  I mean, it's 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. 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?

• 6:46Speaker 02

  Luck plays a role in everything if you're willing to go there. So for example, I was born in the USSR. Communist Russia from nineteen seventeen till nineteen ninety-one basically did not let people leave the country. Communist USSR was a jail. Unlike Iran, more like North Korea, you were not allowed to leave the country. I was born in nineteen seventy-five. In nineteen seventy-one 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 calmed the geopolitical storm. I am Jewish. I was born in nineteen seventy-five.

• 7:30Speaker 02

  And in nineteen seventy-eight, 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, 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 nineteen ninety-one. And I would be a totally different human being. 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.

• 8:13Speaker 02

  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 twenties. My parents could have never met and I'd never been a human being. Everybody is lucky and nobody is 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 twenties 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

• 8:58Speaker 02

  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.

• 9:07Harry Stebbings?

  I've listened to pretty much every episode that I could find, 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. So I wanted to start with a tough one, which was difficult times bringing about very important lessons. What's the most difficult but valuable lesson that you've learned?

• 9:25Speaker 02

  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 60 million. I changed the course of my father's financial life and my mother's financial life, yet I was never getting paid a hundred thousand dollars a year and owned nothing. And I was the operator. 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. Cause I was blindly like, I'm gonna help my parents. When I started asking questions, the answers were not of

• 10:10Speaker 02

  the kind that I was hoping for.

• 10:12Harry Stebbings?

  How did you take that?

• 10:13Speaker 02

  I took it very poorly. It was very difficult. 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. The math is the math. This is how much it did before I took over? Look what's happened. Everything's different. 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'm more than 20x the company. And the answers were no. The answers were, you'll get it when I die. I'm like, well, 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. It was a challenge. Now, I was empathetic. I could understand where my Father was coming from, he was in immigrant land, not in startup land, not in America land.

• 10:58Speaker 02

  He was old country. He was like, it's the family business. And when the dad dies, the son takes over the daughter. 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 because 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 because I feel like you put in so many hours that I feel compelled. Plus, I don't do it because I don't want to paint the wrong picture. My dad's the best. It was just what it was. Those were long nights. That was the first time. And what I learned from it was what I preach, which is fuck money.

• 11:43Speaker 02

  Business doesn't mean shit. Your family, life, happiness. And I am proud to say I was the 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, 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've been doing business with for 20 years, wouldn't even return my call because everyone knew Gary was running shit and Gary was the guy.

• 12:28Speaker 02

  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. He was a senator. Yeah, he owns it, but he has an empty briefcase and nobody's fucking talking to him. And it killed him inside. 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 kind of really worked out. And at 34 years old, I started VaynerMedia with no money.

• 13:11Speaker 02

  We started the company in Buddy Media's conference room, which I'm sure you know because you've listened to a lot of interviews. And I'm very proud of what we've built from zero and scratch with no cash.

• 13:20Harry Stebbings?

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

• 13:29Speaker 02

  Yes, but more of how I encourage all of you. What I know about my kids, even at this age, is they're still forming who they are. But 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. 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.

• 14:09Harry Stebbings?

  When I listen to so many of your shows, and when I listen to you now, the thing I get is like, security. 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. Everyone's insecure and doubtful of themselves in some way. How do you doubt yourself?

• 14:26Speaker 02

  Yeah, I love that question. 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 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. 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, which is rare for me. But I read a book about the 90 Knicks, the 90-0 New York Knicks. 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. 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 doubt.

• 15:10Speaker 02

  I had a lot of doubt as like a teenager. And in my twenties around like asking girls out. My confidence level in like girlfriend, boyfriend, like school stuff wasn't at the same level as business. This one's a wild one. I have incredible fear of reading out loud because I'm terrible at reading. Literally at the Passover table, reading passages frightens me amongst my family. But I can go give up improv keynote to seven billion people on earth right now. If there was a stage for the entire world, literally if tomorrow they're like, there's this new stage and it's simulcast to every person on earth and you can submit for slots and you get to give a 15 minute keynote to the world. I would literally submit for a keynote immediately. If I had to do it right now, Harry, if you were like, actually Gary, I'm a genie from the future and I can do that if I snap my fingers.

• 15:54Speaker 02

  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 you and Andrew right now in my office 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. I'm not kidding. I'm really not scared.

• 16:12Harry Stebbings?

  Has that ever got you in trouble?

• 16:13Speaker 02

  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. 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.

• 16:34Harry Stebbings?

  Guys, 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?

• 16:53Speaker 02

  I am pretty much what you get. Somebody, so 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. 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. About to hang up because 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, could you say something? I'm like, of course. What's up? He said, you've gotten really popular and. Since I've worked here, he goes, I'm probably asked 13 times a day, and I only know like 15 people, his whole shtick of what's Gary really like? And he goes, it's really cool to tell those people,

• 17:35Speaker 02

  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 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, 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, but it's very easy for me to reconcile

• 18:18Speaker 02

  the public output of content versus the things I want to keep private. And it's very important for me that my personal life is extremely private, like extremely private. I don't share anything about it.

• 18:27Harry Stebbings?

  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?

• 18:35Speaker 02

  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 because I've been working every minute and everyone's around the country. And they were at VCon. It was just so awesome, like they were so pumped, 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,

• 19:20Speaker 02

  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. It's your truth. I mean, think about my content. My content is far more therapy than it is business, HBS. 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 of like, 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. You didn't come out of the womb and be like, I suck. You think you suck because your mom told you you suck. You think you suck because your dad told you you suck.

• 20:02Speaker 02

  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 be happier.

• 20:14Harry Stebbings?

  What would you advise me? I get DMs, comments, I hate you, you're a prick, you don't deserve it, you're young, you're rich, whatever. Horrible messages. And it really upsets me. What would you advise me?

• 20:26Speaker 02

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

• 20:32Harry Stebbings?

  Not at all. They don't know me. It's random people.

• 20:35Speaker 02

  Then you're really in a good place. Like for me, one of the things I've liked about pushback, hate, negativity is I start with humility. Is there anything here? Can I take 2% out of, Gary, you're a fucking asshole. It's very hard to take something out of that. But sometimes I will probably be like, I'm really sorry that I triggered this. You can like talk about, well, 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 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. That's why I don't talk about meditation. That's why I don't talk about a million things. So first I start with humility. Then I start with compassion.

• 21:18Speaker 02

  Harry, I do think having some compassion for those people, bro, it sucks to live a life where you actually want to 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 and sending them a nasty DM. I really go with empathy and accountability. I'm like, is there anything right? Are they right? Am I getting too high on my own supply? B, man, I really feel bad. This is what they want to spend. Their time on C, deep breath, reset. There's 99% of the people, 86% of the people that are thrilled and it's going well. Focus on consuming positivity. One of the biggest things that drives me today here is that the world speaks about so much negativity

• 21:59Speaker 02

  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 beat that drum very aggressively.

• 22:17Harry Stebbings?

  You said about where you spend time and I'm using this for just pure therapy session now. 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 maintain?

• 22:30Speaker 02

  Easy, because I don't judge within short timeframes.

• 22:33Harry Stebbings?

  Expand. What do you mean?

• 22:35Speaker 02

  You're gonna like this one. 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 timeframe 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 want to do anything, it's just four days in a 99 year life.

• 23:07Harry Stebbings?

  Can I ask, is that the result though of many years of success and finances being built up?

• 23:13Speaker 02

  No. It's the reverse. 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 twenties 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 get to my folks, not give a fuck. Fuck it, I'll figure it out after because I've got 30 to 99.

• 23:32Harry Stebbings?

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

• 23:35Speaker 02

  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. No. And I also grew up in blue collar. All my friends worked at AMP making six bucks an hour. I grew up in, I didn't grow up in affluence. Me working a lot, it wasn't like my friends were going to sleepaway camp or like Ibiza or the Hamptons. 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.

• 24:19Harry Stebbings?

  That realization causes you to make a decision. You've said before, changing your mind is a strength. How do you know when to give up on something versus when to persist and fucking there?

• 24:29Speaker 02

  Love that question. I like giving up on something when I no longer like it, regardless of the financial outcome. I try to capitalize against being content, satisfied and happy, not maximizing the financial aspect of the situation at hand.

• 24:44Harry Stebbings?

  Does everything have a price?

• 24:45Speaker 02

  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. 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. Everything does have a price because the reality is, well, it's funny game. Like 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 dollars in cash, but you can never work again.

• 25:28Speaker 02

  You must fully retire, meaning the cliche 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 lose, this is gonna land for you and Andrew's in the background here. You know, when you see like an 80 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. I really believe that. And I know business people who stay very active. It is my great hobby. Whatever anybody loves the most, everybody listening, whatever you love the most,

• 26:11Speaker 02

  skiing, sailing, fishing, basketball, traveling, frisbee, beer making, watching movies, whatever it is, 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.

• 26:25Harry Stebbings?

  I want to do three quickfire questions that are under a minute each, so we'll get it done. First one, what have you recently changed your mind on, Gary?

• 26:31Speaker 02

  Well, that's a great question. What have I re- 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. The math of supply and demand of attention on it has flipped aggressively with 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.

• 26:56Harry Stebbings?

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

• 27:00Speaker 02

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

• 27:05Harry Stebbings?

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

• 27:09Speaker 02

  Hopefully in the same exact spot he is right now, which is not anxious about the health and wellbeing of anybody that he loves, meaning nobody is terminally ill, and doing what he wants to do every day professionally. Me doing what I want to do every day means I'm doing plenty of things every day I don't want to be doing in the micro. There's 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 got to have my hands on the wheel and I've got to fix it. That's where I want to be forever.

• 27:42Harry Stebbings?

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

• 27:49Harry Stebbings?

  I mean, what can I say? Such a special one to do there with Gary. Huge thanks to him for giving up the time to join us on the show today. If you'd like to see more from us, of course you can on 20vc.com. But before we leave you today, if you are a venture capitalist or corporate strategist, I want to tell you about Tegus. Tegus is the only company in the world that aggregates qualitative information on private companies from seed stage to pre-IPO. With Tegus, you can access other VCs And founders expert call transcripts from previous rounds to help source fast growing companies, create compelling emails to get a founder's response and diligence companies when a round is moving fast. I use it personally and I think it's insanely brilliant. Tegus is also providing the most flexible and highest quality way to run your own expert calls.

• 28:32Harry Stebbings?

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• 29:17Harry Stebbings?

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• 30:00Harry Stebbings?

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