The Exchanges

Q Let's give people a couple things to do on that. Somebody's listening, they're like, alright, fuck it, Gary told me to do AI. What does do AI daily in order to get better at it look like?

A Inside of Twitter X, using Gronk, Perplexity, or Google Gemini, or probably the one that, ChatGPT is so strong and so easy and common for people, download it and use it every day. Like, and then use it to, like, you, like, here's how I use AI. Hey, AI, like, hey, what are the, this is what I do actually almost every week. What are the five AI apps that popped in the last week that I should pay attention to? AI is answering that question for me, so that I can go look at those apps and understand what's happening. Also, real quick, because I know a lot of smart investors listening here, be very careful in investing in AI. The reason I haven't yet is every week, you think you just invested in the best X, and a week later, somebody crushes that. The speed, you want to talk about speed? The speed in which, like, these apps are getting updated and better is profound.

AI assessment note: “download it and use it every day. Like, and then use it to”

Q Let's give people a couple things to do on that. Somebody's listening, they're like, alright, fuck it, Gary told me to do AI. What does do AI daily in order to get better at it look like?

A Inside of Twitter X, using Gronk, Perplexity, or Google Gemini, or probably the one that, ChatGPT is so strong and so easy and common for people, download it and use it every day. Like, and then use it to, like, you, like, here's how I use AI. Hey, AI, like, hey, what are the, this is what I do actually almost every week. What are the five AI apps that popped in the last week that I should pay attention to? AI is answering that question for me, so that I can go look at those apps and understand what's happening. Also, real quick, because I know a lot of smart investors listening here, be very careful in investing in AI. The reason I haven't yet is every week, you think you just invested in the best X, and a week later, somebody crushes that. The speed, you want to talk about speed? The speed in which, like, these apps are getting updated and better is profound.

AI assessment note: “download it and use it every day. Like, and then use it to”

Q was looking at your investment, Rolodex, holy hell, you have invested in some giant company. I don't think people know half the things about you fully on the internet, but like, Facebook, Twitter, Tumblr, Uber, Snapchat, Coinbase. I mean, I could go on and on and on. So how do you smell like a founder that's gonna win? How do you know what characteristics a great founder or CEO has?

A Very early on in my career when I didn't consider myself an investor, I was unstoppable. Facebook, Twitter, and Tumblr were my first three investments of my life. I only judged what I smelled. I went on pure intuition about the human, and the thesis. I wanted to like the idea, and they were far enough along. I wasn't an angel round. They were a little further. More an A or pre-A. Um, then I thought I was a hero, cause I was red hot, and I started to like, read TechCrunch and spend time in Silicon Valley, and I got caught in an era, a three year era, where I invested in just the idea, and I thought if I, what I didn't realize at the time, what I was doing is, oh, this is a good idea, and I knew how to run it. I put myself into the CEO chair, started spending less time analyzing the person, went through an era of ideas, and I lost. I invested in a company called Yobongo, that basically became, like, basically two years later, an app called Tinder came out and was Yobongo. I loved Yo Bongo, but the kid was a kid, young kid, and I didn't spend enough time analyzing his stomach, his merit, and this was the explosion of, like, smart kids and engineers becoming founders, which are-

AI assessment note: “I went on pure intuition about the human, and the thesis.”

Q We've told them that if you're running a small business, you should think about building up your brand. We've talked a little bit about IP, like all of this talks about content, but the number one of the biggest questions I get asked by business owners in our portfolio is how do you find great talent? How do you find the person to help you with social media?

A By realizing you need to be the person that first understands it a little bit. How do you judge something you don't know? If I went into a surgery, surgery right now, heart surgery, and I needed to judge what's going on, we have a problem. It's called I have no idea what the fuck is going on. Everybody who's listening, when you own a business, it is hard. When you own a business, you have to be adaptable. When you own a business, you have to deal with the shit. I know that you don't like it. You may even have an ideological disagreement with social media. You must be the person that learns it a little bit so that you can judge the talent. It's not about finding the talent. It's that everybody gave the job to their twenty-year-old niece, because they thought like, oh, you're a kid, you get it. The problem is the twenty-year-old niece and nephew use social media to fucking hook up, not to build a big business. So, you know, my answer, and I talk to a lot of these businesses as well, is you have to spend 50 to a hundred hours educating yourself and then doing. You can't read about push-ups to get the results. You have to read and watch videos and listen. I even made it easy for you. Garyvee.com slash attention. I literally took my last book, which is 20 fucking dollars. I'm like, you can't afford 20 bucks? How about this? A 44 page free deck to tell you exactly what to do.

AI assessment note: “By realizing you need to be the person that first understands it a little bit.”

Q We've told them that if you're running a small business, you should think about building up your brand. We've talked a little bit about IP, like all of this talks about content, but the number one of the biggest questions I get asked by business owners in our portfolio is how do you find great talent? How do you find the person to help you with social media?

A By realizing you need to be the person that first understands it a little bit. How do you judge something you don't know? If I went into a surgery, surgery right now, heart surgery, and I needed to judge what's going on, we have a problem. It's called I have no idea what the fuck is going on. Everybody who's listening, when you own a business, it is hard. When you own a business, you have to be adaptable. When you own a business, you have to deal with the shit. I know that you don't like it. You may even have an ideological disagreement with social media. You must be the person that learns it a little bit so that you can judge the talent. It's not about finding the talent. It's that everybody gave the job to their twenty-year-old niece, because they thought like, oh, you're a kid, you get it. The problem is the twenty-year-old niece and nephew use social media to fucking hook up, not to build a big business. So, you know, my answer, and I talk to a lot of these businesses as well, is you have to spend 50 to a hundred hours educating yourself and then doing. You can't read about push-ups to get the results. You have to read and watch videos and listen. I even made it easy for you. Garyvee.com slash attention. I literally took my last book, which is 20 fucking dollars. I'm like, you can't afford 20 bucks? How about this? A 44 page free deck to tell you exactly what to do.

AI assessment note: “By realizing you need to be the person that first understands it a little bit.”

Q was looking at your investment, Rolodex, holy hell, you have invested in some giant company. I don't think people know half the things about you fully on the internet, but like, Facebook, Twitter, Tumblr, Uber, Snapchat, Coinbase. I mean, I could go on and on and on. So how do you smell like a founder that's gonna win? How do you know what characteristics a great founder or CEO has?

A Very early on in my career when I didn't consider myself an investor, I was unstoppable. Facebook, Twitter, and Tumblr were my first three investments of my life. I only judged what I smelled. I went on pure intuition about the human, and the thesis. I wanted to like the idea, and they were far enough along. I wasn't an angel round. They were a little further. More an A or pre-A. Um, then I thought I was a hero, cause I was red hot, and I started to like, read TechCrunch and spend time in Silicon Valley, and I got caught in an era, a three year era, where I invested in just the idea, and I thought if I, what I didn't realize at the time, what I was doing is, oh, this is a good idea, and I knew how to run it. I put myself into the CEO chair, started spending less time analyzing the person, went through an era of ideas, and I lost. I invested in a company called Yobongo, that basically became, like, basically two years later, an app called Tinder came out and was Yobongo. I loved Yo Bongo, but the kid was a kid, young kid, and I didn't spend enough time analyzing his stomach, his merit, and this was the explosion of, like, smart kids and engineers becoming founders, which are-

AI assessment note: “I didn't spend enough time analyzing his stomach, his merit”

Q Totally. But I don't really, I think it's almost an immediate red flag. When I see somebody showing the Gucci Fendi Prada, the fast cars and the private planes, I immediately go, I don't know if you really had that. Do you got to flex it? What do you think? Like, if you're talking to a young person, you're saying don't fucking follow people that do that.

A Yeah, you know, listen, I've taken some lumps from a lot of contemporaries who get mad that I talk about this, cause so many of them are in it. Um, look, I think that It, first of all, it's so funny where my chemicals just went. One of the great things, and it's funny because I pontificate and share and ponder online, 24 seven. First of all, just to set the ground rules, I do not have the audacity to think that I'm right about anything. Anything, let alone everything. For me, I'm in your camp a little bit. But, it's because I think a lot of people do that to funnel people into them, to monetize them. So I think about that a lot, and again, I think it's doing real damage for, like when I post every morning, every evening, I genuinely post from the lens, deeply from the lens of why would someone give a fuck about this post? Why is this good for them? And I do believe a lot of people on the other side of this podcast are not growing because almost every post is about what's in it for me. I want people to buy my course, my book, my collectible, my, you know, you know, and so, I believe that the flashy stuff is inherently selfish, not selfless, and so, but look, I mean, people are allowed, like, you know, people are allowed to share, like, I get it, again, a lot of people grew up insecure and wanted these things, and they're proud, and they wanna share it. My big thing is that peopl…

AI assessment note: “For me, I'm in your camp a little bit.”

Q But what is the opposite of that? What is like the advice that you keep having to repeat? That you know people need to listen to, and they just don't.

A Every single, by the way, every single thing I say, patience, like, insecurity, don't keep up with the Joneses, fuck materialism, eat shit, like, it, it's both the left and the right struggle with me, and like me, right? Because, because in one side, I'm like, compassion, and all the feelings, and everyone's like, ah. On the other side, I'm like, kill every fucker, it's all, like, like, because it is purple. Because life is purple. The reason there's so much tenseness right now is the world, the youth, the elderly, the left, the right, the forties, every generation, Z, X, Y, boomers, alpha, we're fighting for it's red or it's blue. I'm like, motherfuckers, it's purple, you fucking idiots. You fucking idiots. It's fucking purple. How the fuck don't you understand that? So, you know, what, people struggle with everything I say. You know, when I tell parents that you gotta stop giving your kids money after they're 22, every 20, every parent right now listening who's got a 27 year old on the payroll doesn't like getting poked like that. But I'm on the receiving end of all this fucking depression DMs from 28 year olds that are on the payroll. Because parents don't realize if you're paying for your kid when they're a grown adult, you're telling your kid you don't believe in them. Through your actions, not your words. They know they're a loser. Yeah. That shit hurts. You know?

AI assessment note: “every single thing I say, patience, like, insecurity, don't keep up with the Joneses”

Q But what is the opposite of that? What is like the advice that you keep having to repeat? That you know people need to listen to, and they just don't.

A Every single, by the way, every single thing I say, patience, like, insecurity, don't keep up with the Joneses, fuck materialism, eat shit, like, it, it's both the left and the right struggle with me, and like me, right? Because, because in one side, I'm like, compassion, and all the feelings, and everyone's like, ah. On the other side, I'm like, kill every fucker, it's all, like, like, because it is purple. Because life is purple. The reason there's so much tenseness right now is the world, the youth, the elderly, the left, the right, the forties, every generation, Z, X, Y, boomers, alpha, we're fighting for it's red or it's blue. I'm like, motherfuckers, it's purple, you fucking idiots. You fucking idiots. It's fucking purple. How the fuck don't you understand that? So, you know, what, people struggle with everything I say. You know, when I tell parents that you gotta stop giving your kids money after they're 22, every 20, every parent right now listening who's got a 27 year old on the payroll doesn't like getting poked like that. But I'm on the receiving end of all this fucking depression DMs from 28 year olds that are on the payroll. Because parents don't realize if you're paying for your kid when they're a grown adult, you're telling your kid you don't believe in them. Through your actions, not your words. They know they're a loser. Yeah. That shit hurts. You know?

AI assessment note: “Every single, by the way, every single thing I say, patience”

Q Totally. But I don't really, I think it's almost an immediate red flag. When I see somebody showing the Gucci Fendi Prada, the fast cars and the private planes, I immediately go, I don't know if you really had that. Do you got to flex it? What do you think? Like, if you're talking to a young person, you're saying don't fucking follow people that do that.

A Yeah, you know, listen, I've taken some lumps from a lot of contemporaries who get mad that I talk about this, cause so many of them are in it. Um, look, I think that It, first of all, it's so funny where my chemicals just went. One of the great things, and it's funny because I pontificate and share and ponder online, 24 seven. First of all, just to set the ground rules, I do not have the audacity to think that I'm right about anything. Anything, let alone everything. For me, I'm in your camp a little bit. But, it's because I think a lot of people do that to funnel people into them, to monetize them. So I think about that a lot, and again, I think it's doing real damage for, like when I post every morning, every evening, I genuinely post from the lens, deeply from the lens of why would someone give a fuck about this post? Why is this good for them? And I do believe a lot of people on the other side of this podcast are not growing because almost every post is about what's in it for me. I want people to buy my course, my book, my collectible, my, you know, you know, and so, I believe that the flashy stuff is inherently selfish, not selfless, and so, but look, I mean, people are allowed, like, you know, people are allowed to share, like, I get it, again, a lot of people grew up insecure and wanted these things, and they're proud, and they wanna share it. My big thing is that peopl…

AI assessment note: “For me, I'm in your camp a little bit.”

Q What do you think that young entrepreneurs are sleeping on right now?

A So money, different, you know, you know this, we've had the luxury of living just a little bit. We're still pretty young in the scheme of things, but like, you know, I had so many, you know, when I talk about my career, my life, I always think it's a homage to my parents and my circumstance, and so I had a lot of things figured out at 23, right? I, my mom really actually built self-esteem, you know, I continue to believe that most people get successful because of insecurity, and there's a rare breed That gets there through confidence, and I'm so grateful that I'm in that small group, and I see it in others. Um, but that's not me. That's how I was raised, and just the circumstance of being born in the Soviet Union, and Jersey boy in the eighties, and a million other things that are not me. Um, I think a lot about the youth, to your point, and there's just a lot. I think, first of all, both men and women, I think we throw it on men, but I see it in a lot of young women, we want to get validation from the masses. It was always a vulnerability pre-social media, pre-internet, to want validation from the outside, but the outside in 1974 and 1983 was the Joneses, AKA your neighbors. That was like the, you know, like, maybe your church, maybe your, like, neighbor, like, it was tight. Maybe the people in the office, it was small. You know, there's an extraordinary amount of wanting to s…

AI assessment note: “I think there's a lot of lack of self-awareness.”

Q What do you think that young entrepreneurs are sleeping on right now?

A So money, different, you know, you know this, we've had the luxury of living just a little bit. We're still pretty young in the scheme of things, but like, you know, I had so many, you know, when I talk about my career, my life, I always think it's a homage to my parents and my circumstance, and so I had a lot of things figured out at 23, right? I, my mom really actually built self-esteem, you know, I continue to believe that most people get successful because of insecurity, and there's a rare breed That gets there through confidence, and I'm so grateful that I'm in that small group, and I see it in others. Um, but that's not me. That's how I was raised, and just the circumstance of being born in the Soviet Union, and Jersey boy in the eighties, and a million other things that are not me. Um, I think a lot about the youth, to your point, and there's just a lot. I think, first of all, both men and women, I think we throw it on men, but I see it in a lot of young women, we want to get validation from the masses. It was always a vulnerability pre-social media, pre-internet, to want validation from the outside, but the outside in 1974 and 1983 was the Joneses, AKA your neighbors. That was like the, you know, like, maybe your church, maybe your, like, neighbor, like, it was tight. Maybe the people in the office, it was small. You know, there's an extraordinary amount of wanting to s…

AI assessment note: “one thing that a lot of the youth is struggling with is an extreme need”