In short
The episode argues that analog experiences (real-life events, restaurants, live studio podcasts, pop-up shops) will gain value in an AI era, while AI will shift entrepreneurship toward “hyper micro wealth,” long-tail monetization, and brand discovery. It also covers how AI changes work (faster production, fewer “note-taking” roles), why the “middle” may struggle, and how individuals should keep self-worth independent of results—using curiosity, humility, and resilience.
Guests
Gary Vaynerchuk (host) and Rumi (interviewer/guest; described as a “Silicon Valley girl,” pop-culture strategist/strategic thinker). No other guests are clearly identified.
Key claims
- Analog will “explode” as a counterbalance to extreme tech.
- AI enables fragmented “vibe coding” and many small monetizable apps (e.g., 150 people paying $10/month).
- The middle class of entrepreneurship may be in trouble; long-tail could scale.
- Brand becomes crucial because consumers discover via AI “main AI” defaults only after a long transition.
- AI will automate planning/production, but human strategy and brand still matter.
Notable examples
- Gary’s past predictions: TikTok and voice assistants.
- AOL/dial-up as a transition analogy.
- “Bloomberg terminal for free” headline (Claude) as a disruption example.
- Buying/selling in Manhattan (shmata stores → eBay) as a “if everything crashes” fallback.
- Men’s grooming/makeup “looks maxing” and beard trend analysis as an AI-assisted research example.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOPredictions and Insights on AI
0:31 to 2:32
Discussing past predictions about social media and technology with insights on building wealth in the AI era.
“You know, I've been watching you for eight years now, so I've been preparing for this interview for eight years, and what I noticed about you is that you're right at so many things.”
The Future of Wealth and the Economy
2:32 to 3:57
Exploring the dynamics of wealth creation and economic shifts in the context of technology’s evolution.
“coming out of an incredible 30-year run and now walking into a potential buzzsaw.”
Starting Over in a Digital Economy
3:57 to 5:34
Gary shares his approach to starting from scratch in the digital economy, focusing on buying and selling.
“I think, so I believe that the middle will be in trouble and the middle might be a VaynerMedia.”
The Role of AI in Content Creation
5:34 to 7:18
Discussing how AI influences content creation and the importance of branding in a new era.
“I mean, if I was to lose my reputation too, like my face fell off and I have a different face.”
The Value of Analog in a Digital World
7:18 to 10:29
Analyzing the potential rise of analog experiences amidst increasing digital content and AI.
“And in fact, I would argue what I do for a living and what I'm obsessed with actually explodes in this next era.”
Adjusting to Industry Changes
10:29 to 11:42
Discussing how to adapt social media strategies in the face of changing dynamics due to AI.
“Extreme technology but extremely scaled.”
Crafting Content for Diverse Platforms
11:42 to 14:01
Exploring strategies for effective content creation across various social media platforms and understanding cultural influences.
“How are you adjusting your social media strategy?”
Understanding Content Platforms and Algorithms
14:01 to 15:00
Learn how different social media platforms influence content creation and strategy.
“There's a little bit of a different thing there.”
The Role of Pop Culture in Business
15:01 to 16:20
Discover why understanding pop culture is crucial for businesses and brands.
“The Starbucks bear tumbler for three weeks then not.”
AI's Impact on Social Media Strategy
16:21 to 17:12
Explore how AI affects social media strategies and the broader implications for businesses.
“Understanding and how to be good at the thesis is hard.”
Show all 25 chapters
Hiring Trends in an AI-Driven World
17:13 to 19:30
Examine how AI is changing hiring practices and project management in creative agencies.
“But the biggest one I run is VaynerX, VaynerMedia, and there's Chuck Media and the Tomorrow Group.”
Navigating the Future of Advertising with AI
19:31 to 20:51
Learn how to adapt advertising strategies in an AI-dominated landscape.
“and I understand it doesn't work that way, but this concept of is AI a shield and a sword and a gun versus rocks in a war, right?”
Transformative Power of AI in Strategy
20:52 to 22:24
Understand how AI can enhance strategic thinking and market analysis.
“We are also building out incredible capabilities in analog.”
Men's Grooming Trends and Societal Changes
24:57 to 28:03
Delve into emerging trends in male grooming and the cultural shifts behind them.
“And for a limited time, we have the extra big deals you need to impress guests.”
The Evolution of Technology and Its Impact
28:03 to 29:50
Discussing how technological advancements shape perceptions of age and competence.
“A 16-year-old in seven years, that's gonna be like...”
The Duality of Hustle and Happiness
29:50 to 30:56
Exploring the balance between hustle and personal happiness, and the notion of accountability.
“Yeah, but hustle, do this if it makes you happy.”
Detachment from Public Persona
30:56 to 33:10
Understanding the importance of detaching self-worth from professional success and external validation.
“We put on a pedestal someone who's a philosopher or a great reader.”
Parenting and Building Resilience
33:10 to 35:37
How parenting and environment influence children's ability to cope with validation and anxiety.
“What do you tell yourself when you lose?”
Teaching Kids Self-Worth and Independence
35:37 to 37:50
Strategies for teaching children about self-worth and not relying on external approval.
“I want them to be happy and lack anxiety like I was and that comes into this, not anything else.”
Mindset Shift for Personal Growth
37:50 to 39:58
Encouraging a mindset change to embrace challenges and personal growth despite failures.
“Yeah, there's that outcome, but how do you do it?”
Curiosity as a Key to Success
39:58 to 42:01
Highlighting the importance of curiosity in adapting to a rapidly changing world.
“is we've stayed in the negative conversation for 10 years.”
The Importance of Curiosity in a Digital Era
42:01 to 43:22
Learn how curiosity plays a crucial role in thriving amidst AI advancements.
“There's a character that I'm about to write a kid's book about called Curious Crane.”
Framework for Immigrants: Self-Awareness, Humility, Curiosity
43:51 to 47:46
Explore a framework for immigrants to succeed in a new country.
“I think it's a framework of self-awareness, humility, and curiosity.”
Entrepreneurship in the AI Era
47:47 to 50:18
Understand the mindset of real entrepreneurs in today’s landscape.
“And that places limits on what you're doing because you're trying to feed your ego versus built up.”
Practical Optimism vs. Pessimism
50:19 to 55:07
Learn why adopting a mindset of practical optimism is essential for success.
“Yeah, that goes back to knowing who you are.”
Transcript
Automatic transcript. May contain errors.0:00The person that's very comfortable with analog hosting a conference, having 25 people in this room right now while we do this, brands are going to find incredible value in the analog world. Real life, restaurant, real life studio podcast. Real life is going to explode. We're going to live in this barbell world. Extreme technology but extremely scaled. What we take advantage, us four, is like that's normal. Like being outside, a pop-up shop, going to a sporting event. they're gonna continue to increase in value. This is the Gary Vee Audio Experience. You know, I've been watching you for eight years now, so I've been preparing for this interview for eight years, and what I noticed about you is that you're right at so many things.
0:45I remember you predicted TikTok, and you were the reason I started TikTok. I had three million followers there, because you were like, you need to start TikTok. And I remember you were talking about voice, that we're gonna talk to our computers with voice. when it wasn't that obvious because voice wasn't good back then and now it's a reality. So when you're looking at this AI era, do you think it's our last chance to build wealth for right now? That's a great question. I think my, so unlike, you know, one of the things I try to do is when I talk about things publicly, I've spent a lot of time thinking it through and I've seen indicators of actual human action that shows me an insight to the earliest of preview of something I think will be at scale.
1:33So that's why a lot of my predictions have worked out. Your question's interesting because my intuition is it has the chance to create hyper micro wealth, the fragmentation of vibe coding and all this stuff and the stuff we're already seeing, right? kids building out products very quickly and having success. On the flip side, you're also alluding to clearly the super scalers, right? When you look at what Meta and Microsoft and Google, like the biggest companies in China, like you could see a winner takes all scenario where 12 or 13 companies. My gut is that the economy and the consumer behavior is so large that yes, there'll be 25 companies that take so much, right?
2:25You look at, you know, Adobe and Salesforce and ServiceNow, SaaS companies. I mean, SaaS companies are clearly coming out of an incredible 30-year run and now walking into a potential buzzsaw. You know, I saw a headline yesterday. I don't know if it's true. I mean, just, you know, I was busy yesterday, but maybe it was Claude Claude just gave everybody a Bloomberg terminal for free. You know, like, those kind of headlines seem very real to me. They seem really natural. But it's almost like Meta or Anthropic or someone else is going to eat up more Bloomberg and ServiceNow and Salesforce. It's like the battle of the titans.
3:06And then over here on the scraps, well the scraps actually might be quite big and it might be a social media-like era where all of us become, literally all of us become vibe coders. Just like I thought one of my great predictions in 2008 was everybody would have a social media account when it did not seem like that. Are all of us going to be vibe coders and are we all going to have the ability to have 150 people paying us 10 bucks a month for the most narrow little app we built and between social, real life, analog and then having this thing like is Is everyone going to have a mini app that is monetizable because they themselves were able to build it, not need a developer for 500 ,000?
4:00I don't know. I think, so I believe that the middle will be in trouble and the middle might be a VaynerMedia. But I have a feeling the separation of the middle class of entrepreneurship and could be real. The difference is the long tail could be quite at scale, maybe even then creating this middle class. I don't know. If you put a gun to my head, I would say no, it's not our last chance. Okay, so we have a few years, right? I think so and again, let me take another counter just to build on this conversation. If it is our last chance and 79 companies make all the money, governments will get massively involved.
4:46And like it may lead to a nirvana like you know back to where we come from and where we're sitting. Could extreme capitalism mean a different version of socialism? Right? Coming back to the roots. You know what I mean? Could a world where there's only 100 companies that make 80 % of the monies would they then be forced to subsidize all the displaced workers? Do we live in a three day work week environment with the other four days subsidized from the companies that we work from? Do we have more leisure? Do we get more into the arts and family? And do we have side projects that make these micro pennies?
5:25I don't know. So what if tomorrow everything crashes for you? Like VaynerMedia, you lose your followers, what would you do if you have a laptop and AI? I mean, if I was to lose my reputation too, like my face fell off and I have a different face. Yeah, you start from scratch. I start from scratch. Me personally, I mean in real life, before I get into AI, in real life what I would do first is buy and sell. That is my ultimate strength. You know, I'd walk up and down where we are in this part of Manhattan and go into the Shmata stores and buy something for three bucks and list it on eBay for nine bucks and sell it.
6:01Like, I have the ability to buy and sell and that would get me going. To your point and to what I just answered the prior question, I do think I would get very serious about developing in this AI ecosystem and try to figure out how to make something that's$5,$20,$30 a month cost as an app, and how do I create content on Twitter and LinkedIn. If I lost my reputation and my personal brand, but I kept my knowledge of how to make content on social, I would build an app that's $5 to$50 a month and I would make unlimited organic content on LinkedIn, Twitter, TikTok, and try to get customers. That's a very interesting approach.
6:49I just talked to Bill Gurley, who's like a legendary investor, and he told me, you can't even imagine how many websites are there that are just like password photos that charge you$6. and yes, AI can do that but because we're still so used to going to a website and paying and they're making tens of thousands of dollars a month and we just don't realize it. Because for me as a person in Silicon Valley, I'm looking at all the businesses and I'm like, okay, I can totally see how Anthropic releases new lines of codes tomorrow and this business is done. It's not how consumers work. He's right. It's not how it works.
7:18And in fact, I would argue what I do for a living and what I'm obsessed with actually explodes in this next era. It's all going to be about brand because you have to discover it. In 30 years, by default, somebody will be like, oh, let me go to the main AI thing and I don't need to. But there is going to be a long period of time here. AOL dial-up three years ago was still a huge business for them. Think about that. Yeah, so there's this long tail. We still need to adjust. We're, as humans, we take some time to adjust to new reality. When you're a Silicon Valley girl and you even know who Bill Gurley is, you live in a different world than the 99.9 % of people on earth who've never heard of Bill.
8:00And that's opportunity for everyone who's listening. Correct. Because transitioning to that era together with small companies, small businesses, other people educating them. I feel like there is a lot of potential there. When you layer what I've been obsessed with about the last 20 years which is there is a advertising and brand building ecosystem called social media that does not cost you money. And that's the point about AI apps. It really doesn't cost you money anymore to build something in the way that I grew up. But the fact that you can actually get awareness, that you're one TikTok away from having people know who you are and building a platform, that's intoxicating.
8:38But do you have another worry? Talking about social media, right? I see a lot of AI content and we're getting flooded with so much content so we're competing more. But also another thing that I'm always thinking about, what if this social media platform, like why would they pay human creators? Why would they not just, you know, generate AI creators? This is much more personalized content. It's free and they don't have to pay anyone. Well, platforms don't pay people. Well, some of them do. No, they really don't. Like, Meta doesn't pay people. TikTok doesn't pay people. Like, they don't pay people.
9:09They are an open vessel that people go on and create for and then businesses come and sit in between people that make content and people that consume content and then businesses advertise on there or go to a creator and do a brand deal. Now, if you're saying, why would L 'Oreal go to you like they might today versus someone that looks kind of like you that they could even own like a Mickey Mouse. Exactly, and make 100 videos versus one. They're going to do that. Now, right now there's stigma around that and big companies are scared to go too deep into AI because there's pushback. But over the next five to 10 years, they will.
9:47Now, what they might use you for though is you might be one of the 100 faces they use, 99 of which they own the IP, but you're going to be able to do this. I think the rise of analog value is going to be extraordinary. So we're sitting in this world right now where a lot of people behind the scenes doing stuff. I think, you know, for me, and I think you know this about me, I'm comfortable and good in both environments, both with my thumbs and right here. that person's gonna do incredibly well. The person that's very comfortable with analog hosting a conference, having 25 people in this room right now while we do this, right?
10:27Brands are gonna find incredible value in the analog world. Real life. Restaurants. Real life studio podcasts. Like real life is gonna explode. We're gonna live in this barbell world. Extreme technology but extremely scaled. What we take for advantage, us four, is like, that's normal, like being outside, like a pop-up shop, you know, going to a sporting event. They're gonna continue to increase in value. And so, yeah, you're gonna be, like the game's gonna change, but I remind influencers, influencers are crying to me quite a bit right now. Like Gary, AI did, I'm like, you took money from real celebrities.
11:0620 years ago, none of us existed. And all of that money went to Jennifer Aniston. and if you were on Shark Tank, you were the only business people. I, Gary Vee, do not have a television show. I get speaking fees and appearance fees greater than most of the sharks. Right? That would have never been possible. So, the world turns. Shit changes. We just get too comfortable in our space. Well, what's funny is when we're young and we're disrupting something, we like it. But when we're the one that gets disrupted, we don't like it. Yeah. Right? How are you adjusting your social media strategy? Right now, I mean, nothing because of what we just talked about.
11:49To me, I stay in, my last book I wrote was called Day Trading Attention. I live in that environment. So, if AI wasn't even happening right now, I'd still be focused on what I'm focused on. Long form written content. So much more sub stack, Beehive, LinkedIn, X, longer form content. So I hired two full time writers on my staff, journalists, who basically, so Matt will listen to this entire interview and he may hear something that I've said for the first time ever or reinforce something I'm talking about lately. He will start to transcribe, not in an AI world, word for word, but pretty much so that can be done.
12:28But what he's gonna do is he's gonna come up with 15 to 20 follow-up questions. I'm gonna sit down and interview with him, which is why I needed someone who had a journalistic background because it was just transcribing in AI. that. And then we will create a first person article about the barbell theory, why analog is on the rise, right? So a lot more written content. Interesting. And I feel like it's becoming so much easier because I remember a couple of years ago I met, four years ago, I met someone from LinkedIn and they were like, you should be on LinkedIn, I can't write. I'm so bad at that.
13:00And then Chatty Petit came around and my LinkedIn is growing like crazy. Yeah, and I've always had ghost writing infrastructure for my books because I've never been able to write. and but I've always wanted it you know it's funny every book I've written everyone with my written content people come up to me they're like man it sounds so much like you I'm like it is fully me because it is truly transcribed for my words I don't write differently than I talk because it's just the transcription but so writing content I'm incredibly focused on being and this I'm pushing my team right now on this I'm just being remarkable on every platform like obsession to how to win Snapchat spotlight, obsession to understand how to be great at YouTube Shorts to make sure I'm feeding the LLMs of Gemini with my content because I believe that YouTube and YouTube Shorts are an incredibly important source for Gemini future AEO, GEO results.
13:54So I'm hyper-focused on Google ecosystem and Gemini. What's that? Why is Shorts not long form? Both. But I think, but shorts allows me to pump out a lot of how to, why, right? There's a little bit of a different thing there. So just hyper fixation on the craft of the written word, the images, testing new formats. I call it pack, platforms. So I need to know everything that's happening on Substack, X, Pinterest, Instagram, TikTok, shorts, all that. that's algorithms within those. What kind of content, what format, what kind of, is it a reel? Is it a full, like, on LinkedIn, is it right now imagery is doing incredibly well.
14:41Video crushed last year. It's declining a little bit this month. Like, just, so what's the algorithm within the platforms doing? And then C, culture. Like, what is happening in popular culture across everything? Like, you know, America has long, in popular culture, fed from black culture. Now we're seeing Hispanic culture. We're seeing Korean culture. Impacts so much of U.S. pop culture. Slang terms. Quarter zip. La Boo Boo's in then out. The Starbucks bear tumbler for three weeks then not. Stanley cups then not. I love your fashion when you talk about this. Like I see. Well because pop culture, you know, baggy pants for guys.
15:22Like pop culture is relevance. Right? I can make one reference in here of something that's happening in popular culture and then for somebody who's listening, if they're also into the same thing I'm into, immediately we are connected, right? We are connected by being born in the same place. People look for, we're tribal. We love sports. Religion is because the way it is. Cultures, we have, you and I met immediately, we're just from the same place, it is what it is. But by the way, when I walk outside right now, if somebody's wearing a Jets hat, they're immediately my brother. So, you know, I think pop culture, especially in B2B environments, is very misunderstood.
16:00But even B2C environments, the biggest consumer brands I work with in my day-to-day, I think they underestimate pop culture. Yeah, even creators. Like, I'm talking to so many big brands and they've never advertised with creators and I'm just surprised. So, you're saying you're not running faster because of AI. You're just doing whatever you're doing. I'm saying that I don't have a different social media strategy right now because of AI per se, meaning I am, I mean the AI is what's powering these algos on these platforms, but it's not like it's changing my overall macro thesis and it won't change when AI is eating up the world, which is if I wake up from a coma right now in seven years and everything's different, it will not take me long to get back on the bike and be successful because I'll just spend a hundred days paying attention to where is everyone paying attention to, Oh my God, AI changed everything?
16:56We're back to reading newspapers? Okay, I'm going to make newspaper ads. Like, it's not complicated. The thesis is simple. Understanding and how to be good at the thesis is hard. Yeah. Has your hiring changed because of AI? How many people do you have there? You know, it's funny you say that. We, at Vayner, so I have many different companies. But the biggest one I run is VaynerX, VaynerMedia, and there's Chuck Media and the Tomorrow Group. Three very large advertising agencies, all of which do something pretty similar. we're exploding and I'm having this very, very challenging game where we are, our demand, I mean, I was in Seattle yesterday as you heard before we went on here.
17:35I met with the three biggest companies that are HQ'd there, all of which are like, we want to do more with you. We want to do a lot with you. Two that are already working with us. A third that wants to jam with us. So the demand of customers is exploding. I still need an extraordinary amount of human beings because it's human-based business. A lot of the work of project management, creative strategy is getting changed by AI. So like on my flight yesterday, which was a very long train, nine hours on the ground, nine hours on the ground, four hours in flight. And it started to snow right before we took off.
18:18My team was with me, they had to go to LA, they left 15 minutes before us, they got out. We got, yeah, that's right train. so anyway I caught up with my work and I had a lot of time and I was really worksmithing on the plane you know how do I cadence this I don't want to hire all these people only to fire all these people and not protect maybe not even them maybe different people within your organization my preference is to not fire at all because I think there's a really shocking naivete from some of the biggest companies in the world or even mid-sized companies Yes, I understand that AI can do the job.
18:56It is not lost on me that 100 people can now do the work of 400 people. I'm just worried about the output wars of the future. What if you're competing with somebody that has 400 and you have 400? You cut 200 and they still have 400. And in our world, you and I, we're like, ah, we're outflanking them. We're gonna be better, we're gonna make more EBITDA. But what if they weaponize those 400 people with the same tools that we weaponize our 200 people? In my world, advertising, if my 400 people now make 27 ,000 ads and your 200 people make 16 ,000 ads for whatever human element is there, and I understand it doesn't work that way, but this concept of is AI a shield and a sword and a gun versus rocks in a war, right?
19:44You would think 200 will beat 400, but what if the 400 also have shields? And so there's something here that I haven't fully figured out.
19:58I'm definitely being cautious. We are definitely first and foremost attacking things that do not have value. For example, if you're a project manager at VaynerMedia and your sole, because every project manager comes in different shapes and sizes, but if you're the kind of project manager who only takes notes. Like that is how you, well that person has already been kind of smoked out and asked to do more. If you're one that wrangles people, well Gemini's sweet with Google calendars and all that. So we're just kind of chipping away at the thing. But ultimately if you're in production and the video can be made for$8 ,000, that used to cost$8 million.
20:48We're here. We're within striking distance. So there's thoughtfulness to the type of people we're bringing on. We are also building out incredible capabilities in analog. So podcast production, live social shopping production, which is an obsession of mine, experiential, like I was just talking about, analog. We're building out all those capabilities. The robots doing the physical setup of this mic are still a few minutes away. Enough minutes away that I'll probably be on the other side of my career, or at least in a different chapter. So we're just kind of taking it day by day. Was there something that you transformed with AI within your team that blew your mind?
21:29You're like, oh my God. My mind has not been blown since kind of the, you know, I had a lot of friends in Silicon Valley talking that machine learning was getting better and better and then you started to hear it, ML become AI. And then when that, I mean I remember for the rest of my life I was at a Raiders Rams game in Los Angeles with the friends, President Andy Kreniak and my brother called like four times which got me a little worried. And then I finally got him and he's like bro, something has happened. He's like do you know what ChatGPT is? You know it was that day that everyone freaked out four or five years ago, whatever it was now.
22:06Three years, four years ago. It did not take me long. It took me a good 24 hours to be like, oh crap, you know, this is like, okay, I understand what I'm playing with with this first version of ChatGBT, but like, this is, now the cat is out of the bag. I started doing enough research and, no, it just, you know, to me, it can do everything. So why would I, like, when Nano Banana had an update and it was unbelievable. but I wasn't like, I was like, maybe I'm impressed on how fast everything is happening but I'm in a point where like, yes. To me, basically, here's where my head's at. I'm going to take my phone and be like, build this app, I want to do this, enter, done.
22:57So if I'm already there, everything in between is just a step to that. That's where I think we're going. Anything you transformed in your process or you just started but executing by yourself? I mean, like building. Probably the biggest thing that happened to me is I am an anthropologist, pop culture strategist. So having that level of thinking power with me that I used to rely on search and like just digging around the internet, that was profound. Now it's done for you. Well, it's done with me. With you. Right? Yeah. I'm the one who's saying, hey, facial hair. This is a real thing I did. Hey, you know, give me the historic comps of how long the trend of beard, mustache, or clean-shaven face, like what are the historic trends?
23:50And what were the pinpoints? And this is actually the prompt I gave. I remember that when friends got popular, all my friends started to clean shave because Chandler and all the boys were all clean-shaven. Like what were the tipping points? why, how, what, hipster, mustache, mullet, because I'm looking for business opportunities or marketing opportunities that might be one or two years before everyone else can see it. And I think a lot about the razor business. You know, men are becoming increasingly focused on their looks. K-pop Demon Hunters, Haja Boys Breakfast Meal, and Huntrix Meal have just dropped at McDonald's.
24:30They're calling this a battle for the fans. What do you say to that, Rumi? It's not a battle. So glad the Saja boys could take breakfast and give our meal the rest of the day. It is an honor to share. No, it's our honor. It is our larger honor. No, really. Stop. You can really feel the respect in this battle. Pick a meal to pick a side. Ba-da-ba-ba-ba. And participate in McDonald's while supplies last. Spring Fest is heating up at Lowe's. And for a limited time, we have the extra big deals you need to impress guests. Get your outdoor space ready and save$50 on the select Cobalt 24-volt blower kit.
25:09Now$79. Plus, save$80 on the Char-Broil Performance 4-Burner Grill. Now$199. It's springtime, and our best lineup is here at Lowe's. Valid to 413. While supplies last, selection varies by location. Is that what you're seeing now? Yeah, I mean, that's been a trend. I mean, you can see videos of me seven years ago, six years ago, talking about male makeup. Like, yeah, I mean, I just think that men are so loaded with so many insecurities that we are like now adding another one and joining the ladies with our visual, you know, like obsession. Yeah, you're seeing it. You're seeing some of the streamers do looks maxing and all that stuff.
25:50Like, yeah, I mean, this has been going on. It makes sense. We're all living public lives. Boys always wanted girls to like them. It's always been up. We're all social media. We're all that. you know, it just makes sense. I mean, the world is actually good. In all the trauma, the world is actually in a lot of ways better than ever, so we focus on dumb shit like our looks. You know, when it's the Great Depression or the Black Plague or World War II, no one has time to like worry about their fucking looks. So I think we get very confused by the negative headlines. The net net of the world is good, rendering a lot of 17-year-olds and 40-year-olds to have time to focus on their looks.
26:27so yeah I look at that kind of stuff anyway I'm bouncing around as I tend to do but my ability to have thought and then open app and talk with GPT through the potential of a trend and then also go to web and also do my social listening on social media Reddit other things of that nature I've become a much sharper more effective strategist in the last year Yeah, I feel the same when I was flying here yesterday. I was playing with Claude Scales. Yes. It's like a skill that you can build. Yes, of course. It was preparing me for this interview and I was like, this is fascinating. I feel like I'm a superhuman with all these tools because Perplexity Computer every day sends me stocks to buy, Claude Scales does my research.
27:16It's just fascinating. Yeah, but I also think it feels like a superhero today the same way I felt with the iPhone. That first year with the iPhone. So I bought the iPhone the day it came out. especially in New York because of Wall Street and any big city, there was Blackberry obsession. And I felt like a superhero that first year because I could go on the internet for real, not like the way the Blackberry people could. And that gave me a hyper advantage. Like I would go and do, at that point I was already out a little bit, I would go and do something and I could look something up before I like went on stage or went into a meeting and that was like powerful in a way that I didn't have to do with my laptop even though that used to have that.
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27:55It was just so fast. You feel like a superhero with clawed perplexity, GBT, Meta's infrastructure starting to get very impressive. A 16-year-old in seven years, that's gonna be like... Basic. By the way, a 22-year-old next year or the year after, maybe 24 months, that becomes the most basic of basic. To remind everybody who's listening, your grandmother in the office did not have internet, did not have AI, did not have social media, didn't have an office to your point, did not have mobile computing, did not have computer in office, did not have internet. Like, yeah, I mean, this is just technology.
28:43But do you feel that we're in this period of time and we are like 1 % of grasping technology, do we need to run faster to make the most out of it? Well, it depends on the human ambition. I mean, I think a lot of people are gonna check out of this era. I think there's a lot of people who've made a lot of, let's talk about Silicon Valley. I have a lot of Silicon Valley friends who were psycho, all in, going so hard during early Web 2, 2005, 6, 7, 8, blogging, podcasting, and then social, who made enough money and are in a different part of their life now who have given a shit about AI and blockchain.
29:19Could kill us. I feel like this is just such an opportunity and it's unique for the next 10 years. I feel like we have this year and then it's basic for everyone. I don't think so. I think that makes sense that you think that and I understand that. I think you and I will see each other in 10 years and be like, man, you were right. It's just, as much as it looks like AI creates a winner takes all world, I have a funny feeling it's not going to. Okay. Because don't forget. Hey everybody, hope you're enjoying the podcast right now. make sure you follow the podcast that's why I'm interrupting let's keep going on this show but follow the podcast it'll make my mom super happy there is the human like there's it's gonna take too much time like you know what people don't do well hang with me for a second let's play this game let's take that point let's say 10 companies won everything do you literally think that 8 billion people are gonna be like yeah that's awesome no okay so that's it it's just funny to hear this from you because you're the one like, hustle, do this.
30:21Yeah, but hustle, do this if it makes you happy. People don't like to take my sentence in its totality. Hustle, go hard if you complain and are a crybaby and you don't realize that accountability can help you. Hustle, if you like it so much that you would do it if it was free. I would build businesses if it was free. Meaning like it made me, like it's my joy. I build companies the way people like to go golfing and cooking and watching movies. It's more fun to me. You know, it's so funny. We put on a pedestal someone who's a philosopher or a great reader. Someone who reads books all day in the room is a real thinker and writes, oh wow, so noble.
31:07That's what I do. I just do something with it. On the other side. You know what I mean? So I think hustle, if it makes you happy, one could argue that the extreme opposite of hustle is what I also do, which is complete simpleness, complete lack of materialistic stuff, completely checking out, detached. I mean, the more you know me, the more you would realize I'm incredibly detached from my career or my public persona. I'll make it very blunt. I don't give a fuck about Gary Vee or my Vayner empire. I do not think it makes me better then. Who cares if I'm good at business? Some people are good at skiing.
31:51Some people are good at singing. Some people are good at writing. It just happens to be something I'm good at. I have my self-worth wrapped up into who I show up as, as a human, to people in my life. That I'm a nice guy. Is that a switch ever in your life? Absolutely not. Never. It was ingrained in me by my mother and my circumstances is in my DNA.
32:17What would you say to someone who thinks their worth is tied to their results? And that makes them very anxious in this era. Correct. I would tell them that, first of all, it depends on what results, right? You know, if you're saying financial results. I don't know. I'm in Silicon Valley. Great. Your company's valuation. I would say I understand. It's a very common human trait. I would also say that almost everybody I know on earth that is wrapped up in that metrics mindset has incredible anxiety. And anxiety sucks. How do you separate yourself? I feel like it's easier to say for you because you have all the millions followers already and millions of dollars.
32:54You're saying that because you don't know me. If my friends that have known me my whole life will tell you that I have the millions of followers and dollars because I've always been this way. That's the reason. Right. My detachment because I have an incredible relationship with losing. I like it. What do you tell yourself when you lose? That I sucked and that was funny and let's not try to do that again and what can we do different? I love the challenge. I was the kid when I was losing in sports or ping pong or pool. I loved playing again. I loved playing again. I loved playing again. I didn't think me losing in front of my sister or mom meant that I was lesser then.
33:36I also grew up with bad grades. So I very quickly had a relationship with the machine that was quite healthy, which was, oh wow, I'm really not good at this, but I don't have my self-esteem wrapped up in being a DNF student. Look how well I'm liked. Look at this stuff I'm doing off the schoolyard in business, selling my trading cards lemonade. So I played outside of this short-term validation framework and I also was incredibly structured to not struggle with peer pressure in high school and in college when so many of my contemporaries did everything for validation amongst their peers, I did not.
34:15And that was just tremendous parenting, luck of the draw with DNA, and the circumstances I grew up with, you know? You know, when you're growing up Soviet, but you're growing up in America in that era of the 80s, I just had a different framework. What are you telling your kids? Well, they're not me. I'm trying to leave deposits on that, but they're growing up in a very different environment. Now, luckily, my children share a lot of mine and my ex-wife's DNA and are also a little bit cocooned. Like, my 17-year-old daughter does not live her life for her friend's or boy's attention. So she's cooking with gas.
34:54My 13 year old son also, I would have said three years ago, he's already starting to really develop this. And so, look, DNA is a real fucking thing. And then when you have parents that are conscious and are pushing you on the right things, the only core thing that for sure they have different is environment. I grew up in an environment with very little. They've grown up, my son defaults to thinking, yeah, you go to a Knicks game, you sit courtside. I sat in the last row, literally, actually, actually in my first Knicks game. So I think it's, I don't have this ideology for my children to be exactly like me or just like me or they need to be hungry like I was.
35:40I want them to be happy and lack anxiety like I was and that comes into this, not anything else. This. Any tip how to teach that? What's that? I have a four-year-old and a six-year-old, and I feel like they really rely on what other kids think of them. What do you tell your kids? I pounded that narrative into my kids verbally. You just tell them like you. I think it's, like, as young as that, I would tell my children, like, people making fun of you, people saying you're awesome, means nothing. How do you feel? What do you like? Yeah, and learning not to react to positive things and negative. The reason I can deal is I today have 95 % validation, 5 % skepticism and pushback.
36:30It's the goat emojis in my Instagram posts that I have to not pay attention to. Not the you suck Gary or you got lucky or you're a snake oil. To me it's not hearing the accolades. I'm telling you that that's where the lack of anxiety comes from. I don't need to have a house or a plane or a third home or a Nobel Peace Prize or 40 million followers or an exit to impress Bill Gurley, you, Kevin. I don't need that. It is not what my life is about. I like it but I feel like I'm an athlete who wants to be great on the field but off the field that is not the man that I think I am. I absolutely love this mindset and how people, I feel like everybody should learn this type of mindset especially now because also I have this question from my team please who read your piece a I split people into architects and masons yes and half of my team thinks they're masons but they have the ability to become an architect so how do you deploy that mindset when you know you're losing right now yeah AI is replacing you but how do you go to the next step of your career utilizing this mindset that I don't need external approval and this mistake of failure is a means how do How do you lose 25 pounds when you know you're not feeling great?
37:50I'm asking you. Well, it's either or. You die sooner than you don't. Yeah, there's that outcome, but how do you do it? I'm not saying what the outcome is, and you're right about that. Like, I don't know, I don't have this problem. Right. My husband has this problem. Okay. He loves sugar. Yeah, me too. So, yeah, he just feels worse. And for him, it's stopping sugar completely. Yep. It works. Yep. Like completely. But it's hard. It is. Like I go through patches where I also cut it out. So I'm your husband. I have the same issue. Sugar is the real bane of my existence. To me, let me tell you how I stopped drinking soda for every beverage 13 years ago.
38:34I hired a full-time person literally 12 years ago. There would have been a man in here right now to make sure I didn't take a sip. Really? For one year. I took an extreme measure of babysitting to get me into the discipline. He suffocated me to then get into patterns to get into the discipline and then it became my norm. If you are a mason and you want to become an architect, you can cry about it. You can stop and start. We all stop and start in health, in wellness, in work. But you need for it to become your actual pattern. It becomes your norm. To your point, sometimes it's cold but it starts here first.
39:15Like if I had that whole team right now, I'd be like, listen, you can do it. You have to believe that. If you don't, what are we gonna do? Like it first starts mentally and then it starts physically. Like you need to start using these tools to help you think better, to put in the work. You need to start reading. You need to start doing this. You need to start hanging out with these people. Like you need to start taking from your leisure which you're using to get an escape from your concern and you need to allocate some of your leisure time into more work. You have to go to the gym and eat better.
39:45That starts with your mind, but then it has to happen with your actions. And then you just have to stay into that conversation. Like this is staying in a conversation. The reason the world is so tight right now is we've stayed in the negative conversation for 10 years. But like my newsfeed is not politics. My newsfeed is not telling me that the world is going to shit. My newsfeed doesn't tell me that my parents had it better than me. Like, you're in control of your algorithm, you're in control of the people that you spend time with. Look at all the people that are listening to this right now. These people chose to follow you and listen to you.
40:24Some are here because this is the first time they're listening to you because they follow me. Knowing enough of your platform and definitely knowing my platform, these are people that are choosing offense. These are people that are choosing optimism. These are people that are choosing to try to figure it out. That same person could have a twin sibling who right now, this is a Saturday morning that you and I are filming this, who might be watching Netflix this morning, which is lovely and you should have leisure, but why are they watching it? Are they watching it because they have a little side dish of leisure and enjoyment?
40:55That's beautiful. But if it's their main course and they're doing it because they had an anxious week and they're devastated that they have to go back Monday, now I'm concerned. Does that make sense? Totally. To me, leisure and escapism needs to be side dishes and a moose booshes, not the main meal. When it's the main meal, you are escaping your actual life that isn't going well. And that's what I think. And the idea of hiring someone, you can totally hire an AI coach who's going to plan out, like you hire someone who took soda away from you. You could. That could be an AI coach. You could. What's even crazier with AI is your AI coach can be the AI itself, which is a whole new phenomenon.
41:38Yeah, yeah, yeah. And it's fascinating. how it works. You just, you get your strategy, talk to it maybe once a week, updating on your strategy creates a plan for you so you have something that you talk to. You know, it's funny, I, so I have this company called VFriends. It's my Pokemon meets Marvel meets Disney meets Sesame Street Universe. Collectibles, toys, cartoons. I'm really loving it. 250 plus characters. There's a character that I'm about to write a kid's book about called Curious Crane. So I have a character and be friends called Curious Crane. Crane is a bird for everyone who doesn't know this.
42:14I'm excited about it because I actually think curiosity is going to explode in cultural value because I think it's a trait that makes you very conducive to doing well in the AI world. I would tell a lot of your masons to get their curiosity up. Yeah, and it's something that's really empowered by AI. Incredibly. Because you can go down the rabbit hole and all information in the world. Okay, let's talk about people who are watching who are immigrants, because I have a lot of immigrants watching. You came to America at age three. I came when I was 25. For someone who arrives today, what is the first thing they should be doing?
42:52Today, we helped a... Latte for Sam. ...coffee shop get an insurance quote simply and easily and made sure... ...a floral delivery van was able to make someone's day. We're the Hartford, with decades of experience insuring millions of unique small businesses. When it comes to your small business insurance, Thank you. one size absolutely does not fit all. Get a quote or find an agent today at thehartford.com slash smallbusiness. This episode is brought to you by Indeed. Stop waiting around for the perfect candidate. Instead, use Indeed Sponsored Jobs to find the right people with the right skills fast.
43:33It's a simple way to make sure your listing is the first candidate seed. According to Indeed data, sponsored jobs have four times more applicants than non-sponsored jobs. So go build your dream team today with Indeed. Get a$75 sponsored job credit at Indeed.com slash podcast. Terms and conditions apply. I think it's a framework. It's funny we used curiosity. I think it's a framework of self-awareness, humility, and curiosity. So self-awareness is if you come from Guatemala, Poland, South Korea and you're here in the US or by the way, you're an American who's deciding one of those people which you're allowed and you're moving to Sweden or you're going from India to England or England to Argentina.
44:19No matter what shift you're making, a lot of people listening here will move to other countries because of jobs. Their wife's the big executive, they're the entrepreneur and she just got a big job and now you're moving to Portugal. When you are new, in an entirely new country, immigrant, I think there's three things to rely on. Number one is self-awareness. Who are you, right? When I came over, I was a kid, but the older generation, these people were engineers in the Soviet Union and they were literally cleaning toilets. That was the second part, humility. You know, humility is a superpower. You know, I'm aware that my humility does not show up on the internet, because that is not the way I communicate.
45:03But I will tell you that in my real life, behind the scenes, it is one of the beacons of my success. I've never gotten away from the kid that immigrated. Like, with all the stuff on paper, I still don't think I'm better than. I don't think I have earned the ability to not put in the work or to be gracious or to be kind or whatever it might be. So I would say self-awareness. Who are you? What are you good at? You have to then see if that's available to you in the country. Sometimes it is. Sometimes it's not. Nuclear engineers from the Soviet Empire literally had to clean toilets because America wasn't just giving them jobs.
45:43And then they had to build themselves up and they owned a pharmacy later on. You know how it all worked out, right? Humility. I know that you were the big dog in India but maybe here in Poland that doesn't work. or you were amazing, you were a good creator in America but now for some reason you live in Indonesia and you don't have that many followers in Indonesia. Humility, right? And then back to curiosity. For me, I would just, again, face got ripped off like that John Travolta, John Travolta, Nicolas Cage movie. Reputation lost. I find myself in Peru. This is where I'm going. Who am I? I have good people skills.
46:19I have work ethic. I know how to buy and sell. I know consumer behavior. Next. Humility, I'll go work in a store as a cashier. If I have nothing, if I have nothing. And then curiosity, at night after I get back from the store, what's going on here in Peru? Like where's my angle? What can I do? What can I sell? So that is my advice, that emotional framework. And then you have to act on it. Humility, it means like you're teaching yourself or you are, you have this trait, remembering where you come from, right? That's right. But even I believe based on my mother and based on how she would have parented me that even if I wasn't an immigrant, even if I was my brother, the third in the family, born in 1987 in America when we were on our way to middle class, I still think if I had the same exact DNA and I have the same mother, I think humility is there not because I came from Russia and remember.
47:19It's just because I think it's icky to be the other way. I don't think it's like a, I remember where I came from, though there's part of that, I'm sure. It's more like, I just don't understand, well, actually, let me rephrase, I do understand. I'm just not insecure enough to not be humble. Love it. Ego is just pure insecurity. Ego is just pure insecurity. Posturing, trying to be the big dog, that just means you're fucking scared. That means you're a bitch. And that places limits on what you're doing because you're trying to feed your ego versus built up. Yeah, you're just, you are not good internally, thus you must render your peacocking to trick everyone around you.
48:00And by the way, I'm not mad at it. Do you know that I'm not mad at people that are like that? I'm sad about it. I wish they could like themselves for all, do you know how many shortcomings I have? Plenty, we all do.
48:15Okay, if someone's watching right now and they're like, okay, I'm gonna work on all of this, but I really want to build in this AI era. What do you think is the biggest opportunity right now? It goes back to the last question. There's a million of them. I just don't know the person that's listening right now. Are they some, I mean, for example, if you're overly charismatic, the biggest opportunity is to go live streaming on the internet and then drive all of that audience to an AI app that you built that's 10 bucks. Before it's automated by AI because have you seen in China how they're doing this live streaming?
48:50Of course. They just basically put an item in front of the camera and it's automated and there's this AI person already wearing it or showing it. That's right. Including the influencer is AI. It's me and I put your face on me and I'm a woman selling makeup. When I think about this, why would I start if it's already being automated? Because everything you learn along the way will set up your next thing. What are you going to do? Lay down and cry? I don't know. Find something else. Like this is, because I feel like a lot of, because I'm talking a lot of entrepreneurs, they're in this stage. They're like, oh, I really want to do this?
49:25But then, yeah, it's just gonna be taken away by a big company. You're too young for this, but in 2005, 6, 7, 8, 9, in Silicon Valley, the same thing was being said. Why would I start this? Google's gonna copy it. You're just talking to fake entrepreneurs. Okay. Real entrepreneurs are willing to lose. real entrepreneurs know that the two years they work on something that Claude fucked up was two years of them working on something that sets up their next thing. Real entrepreneurs don't know how to do anything else. Real entrepreneurs don't lay down and cry. Real entrepreneurs don't say fuck it I'll just go get a job.
50:07Real entrepreneurs are real entrepreneurs. They just do what they have to do. This is why there were so few of them before the internet. Entrepreneurship got cool. so now people do it because it's cool do you know how many entrepreneurs you talk to that are actually executives disguising as entrepreneurs let me give you the answer most real entrepreneurs have no idea what the fuck you're talking about like you should have seen what my chemicals were doing when you brought that up like bouncing what are you talking about a real entrepreneur is swimming in the ocean and when you say, well, we're not gonna make it anyway, let's just drown to the bottom, like it's life and death for a real entrepreneur.
50:50You can't do anything else. Yeah, that goes back to knowing who you are. Correct. And by the way, let me say something right now. This is actually a beautiful segue. I need everybody to hear this. If you're listening right now and you think you're an entrepreneur but these last three minutes of this talk are triggering some weird feelings, do you know how awesome it was to be the number seven at Facebook? Do you know how incredible it was to be the number nine at Tesla? Do you know how epic it is to be number 34 at LinkedIn, Microsoft? I mean like. How cool it is to be a podcaster? Correct. Like this concept that like, again, I grew up entrepreneurship wasn't even a word.
51:31Being a businessman was not cool. And then I, ironically, was part of the movement that kind of made this thing cool. but I have been talking for 10 years of like, please, it's only cool if you are that. It's not cool to be a teacher if you're not a teacher. It's not cool to be, you know, fuck, it's not cool to be anything if you're not actually, you know? Yeah. That is a good ending. And I have a few questions that are fire - Rapid. Like, yeah, 15 seconds. What are your top three favorite AI tools that you use daily? GBT, Claude, and honestly, the Mangus is really, like, is really, yeah, Meta's, like, I'm, I'm like just a couple weeks going in, but it's.
52:19Do you use it for Instagram? Yeah. Yeah, because I feel like they have access to all the data. Correct. They can do better analytics than anyone. Correct. Okay, that's a good one to work on. What's your favorite prompt? My favorite prompt is me intuitively feeling something that's happening in culture. I'll give you one right now. Does the baggy pants movement for men have another domino to fall? That's a very advanced prompt. So you know exactly what's happening and you're trying to predict what's next. Correct. Almost everything I'm doing is that. For me, for what I like to do professionally and personally.
53:02Okay, college degrees in 2026, yes or no? For 50 % of the people that are listening right now, yes. They need that degree to do the profession legally, in medicine. For the most creative and entrepreneurial people, yes, if mommy and daddy paid for it, because 18 to 22, as a full-pledge vacation, to hang out with other 18 to 22 year olds is a lot of fun. It is. And you will work your whole life. No for 18 to 22 year olds that are taking on substantial debt who are creative and entrepreneurial. Makes sense. One industry to stay away from. None. Everything's in place. I mean, look. Betting your whole life to be an admin who doesn't think.
53:58An admin that's a mason, not an admin that's architect, bad. Admin that's architect, huge. I'm gonna hire people that have the power of 13 admins for me and she or he is gonna sit at the top of that and I'm gonna pay that person a fucking fortune to make my life effective. Yeah, and the last one. What's the most misunderstood thing about AI right now? The counter to whatever anybody's thinking. so for the people that are delusionally thinking this is the greatest thing ever the counter of the negatives that are gonna happen and for the people that think everyone's fucked and China and perplexity and Anthropoc and America and Russia there's gonna be nine countries and nine companies and everybody else is fucked are out of their fucking minds the counter to the extremism of what people think thank you for your positivity and energy you're welcome it's really charging right What you're saying gives energy to create.
54:57Versus like, just lie down. And I think that sits, thank you, and I want to end with this. That doesn't sit in some blind optimism or even the great parenting that I was given. It sits in historics. It is historically true that we were scared of electricity and it wasn't. We were historically true to get off the farms. We did so much more. Humans are great. I know we're told that we're not. but 99.99 % of us are either neutral or great and if I am wrong here's why I'm this way and if I'm wrong I promise you you're not going to worry about your job. If I'm wrong we're all dead anyway. So either I'm right that you should choose practical optimism and there's going to be a million opportunities for you if you go insular and work on you or if unfortunately I'm wrong I'll see you in fun fucking heaven.
55:54Like, you know, you know, like this, I mean, I don't get it. It's not practical to be pessimistic and cynical. It is not practical. Yeah. Love it. Thank you. Everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this.
From the publisher
In this episode, I sit down to discuss the massive shift we're seeing in 2026. I talk about the "Barbell World," where extreme technology and real-life analog experiences are both exploding in value. I encourage you to stop being a "mason" and start becoming an "architect" by using AI to scale your thinking rather than just your tasks. I also discuss why I’m hyper-focused on YouTube and long-form writing to stay relevant in a world driven by LLMs. You’ll learn about:
The Rise of Analog Value
How to Build an AI-Proof Personal Brand
The Difference Between Real Entrepreneurs and Executives
How to Use "Practical Optimism" to Beat Anxiety
Why Curiosity and Humility Are Your Greatest Superpowers
