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Gary Vaynerchuk
Hey, everyone. Welcome back to another episode of the GaryVee audio experience. On today's episode, we have another Micro V for all of you. In this one, we're sharing a conversation between Gary and Alvin Bolles, general partner of Alpha. Gary dives into why pretending to know AI is more dangerous than not knowing how to approach AI without fear, and the importance of learning these new AI platforms. This episode is perfect for those who don't want to get left behind in a rapidly evolving AI age. Let's get right into it.
Alvin Bolles
There's this, this notion around artificial intelligence and people faking it like they know what the hell they're doing, right? So most of the people that I'm on boards with are much older than I, less tech savvy than I, and their fear of disintermediation, of course. And so that last part, but that's the thing. And so it's like, well, but nobody really wants to admit what they don't know. How do we actually move the needle to like, she 1 bring people's guard down so they can actually leave their trepidation of what they don't know and like, just say, man, I don't know. And like, where, where are you actually staying intelligent on this shit?
Gary Vaynerchuk
The real answer to question is good parenting. You basically just asked me, how do we tone down the insecurity and rev up the humility of people that have achieved success, often by posturing, being political, or just the luck of the draw, besides all the elements of their own hard work and things of that nature. It's a huge challenge. One of the things that's been fascinating to me in the journey of my career is I started in such humble places. There was. And I wasn't around corporations until I was 35 years old. I didn't know anything but family business. Everything that we ever talked about was so practical. The first, you know, 15 years of my career, everything was so practical. Like, you know, if marketing, which is my passion, my father Sasha, cared how many bottles sold in a store. He didn't care if it would have won the award. All this stuff today, it's perfect that we're filming this today. He wouldn't give a shit about an ad meter. He wouldn't give a shit about USA Today's top five. He wouldn't care about Twitter, right? He would be like, did we sell stuff did it? And did we sell stuff today? And can we feel that we've sold stuff tomorrow? And things of that nature with this conversation? Because of Web one, because of Web two and a lot of my career when I started to understand corporations and what you're talking about with web2 social and then with web3 blockchain and crypto and, and within them, as they were iterating, it became obvious to me. I'm like oh snap. Some of the most intelligent, powerful, best, most accomplished people I know, when the new thing comes, they peacock and they don't know. It was shocking to me at first because I was so naive. I didn't grow up at good academic structure. I just didn't see it until well into my life. And all of it was based on the stuff that I do know well, which is human behavior. It was always and so about insecurity and humility. So for everyone who's listening when you are faking it, when you're a 57 year old or 40 year old or 12 year old or 90 year old. But let's talk about boards or executives. Cause that's what we're talking about here. Please know something. And this is literally for the creme de la creme that I know are listening to this when you're faking it. The smart 3% know.
Alvin Bolles
Absolutely.
Gary Vaynerchuk
Like let's talk about our industry, the people listening here.
Alvin Bolles
Yes.
Gary Vaynerchuk
There are a lot of people that are wildly successful in our industry. Known absolutely in the marketing hall of fame on the list. Like have big money but are not as respected as they think they are.
Alvin Bolles
Correct.
Gary Vaynerchuk
Because they are constantly bullshitting or building up their personal brand or things of that nature. By the way, everyone who's listening is allowed to live their life the way they're living it. I in fact, even with ironically within the AI thing because I've been so busy. You know me pretty well at this point.
Alvin Bolles
Yeah.
Gary Vaynerchuk
When the Web3 thing happened because I'd spent so much time on it because I had crossed every T and I. I was outrageously loud.
Alvin Bolles
You were.
Gary Vaynerchuk
I'm not very loud about AI. AI has been red hot for, for a minute for 15, 18 months now. You know this. I'm putting out unlimited content. People are not seeing a lot of AI content. For me they're seeing macro AI content. More about fear. Like you know, they'll hear me say people used to be scared to put electricity in their house cause there was demons in it. Let's not do the same thing with AI. They'll see those things. But I'm not going deep into the modeling. I'm not going deep into like my point of view about the news or like the new app of this or what Happened with Blue sky or Deep Seek or that Deep Seek and like how quick like I'm not jumping hard on that because I know I'm stretched in right now working on different things and I know where I'm at with AI. What I do do that I wish more people did is I'm in my journey of not being scared of it. I use it every day. That's it, that's it. I use it every day. I use many of them. The day I heard about midjourney, I used it. Let me see how to make a picture in a video. Absolutely day perplexity like I'm doing it, I'm using it. But there's people within my own org usually I pride myself of being like the guy. Like literally when I say the guy in Vayner, I am genuinely in belief that I know how to do social media creative to maximize reach better than even my experts within my own company currently there are many people cause I've sent them to go do the work that are deeper in AI stuff than I am. And that's okay. I'm on this platform. I said yes to doing this interview correct. And I have the confidence and humility and comfort of being like hey, I'm only a couple steps into my journey and I don't think I can go on a panel with same Altman even though I have the name status to be on one. The reason I'm saying no is cause I'm not gonna contribute well and I don't wanna go up there and just say a couple of fucking 50 words of just generic shit. Where am I? I understand, where am I? I'm meeting with startups last week to figure out how to win the semi on that's right, on AI bots. Because I know what happened with SEO. I was there when we went from yellow pages to search engines.
Alvin Bolles
That's right.
Gary Vaynerchuk
I know search engines are in trouble 100%. We all know we're watching how we all work. I'm 49 years old, I'm in the business, but I got one for you better At Super Bowl I was in a restaurant in New Orleans and four, three or four people were sitting at a table next to me in their 60s or 70s and one of them was explaining to the others why they need to use ChatGPT and not Google to search. Oh my God, this is going to happen fast.
Alvin Bolles
I mean it's happening so fast. Which is why people are saying like you've got to divorce your fear from it. And to your point, admitting what you don't know, allowing people to actually, you know, educate you or your company or just experimenting with it. Part of the issue that people have is that they're not testing it.
Gary Vaynerchuk
Well, now you're going into my biggest issue.
Alvin Bolles
Well, let's, let's get into it.
Gary Vaynerchuk
My biggest issue in life is that most people are not practitioners. In fact, in fact, back to your former employer. I had a meeting in that office right across where a big dog within your company, she's no longer there as well, was starting to break down things for me and I literally had to stop the meeting and say, you don't know the platform. You know how to make a lot of money for the platform.
Alvin Bolles
Correct.
Gary Vaynerchuk
But you do not know the platform.
Alvin Bolles
That's actually not how it works.
Gary Vaynerchuk
And so. Or how to get the best results. I know that you've been told as a sales individual what best practices are. That's wrong to the algo right now. So again, if anybody who's listening to this leaves with anything of value, download all of them and use the play with all of them. That is how you will have some level of context. And then when you're ready to go all in, surround yourself with people that have actually done something. When the NFT thing was going on.
Alvin Bolles
Yes.
Gary Vaynerchuk
One of the things I, you know, I would have a lot of conversations with companies and different things, and a lot of them be like, oh, what about? But Gary, I heard this and I'm like, yes, but I did this and this is what happened and what you heard. Let me show you what they did and what happened. Like, I think a lot of this comes down to a do your own homework. Yeah. That goes back to downloading the apps and playing do your own homework. Be. Pay very close attention to who you're listening to. Are they. And I live both of these lives, but the way I live the first one is what I'm most proud of. Are they a talking head?
Alvin Bolles
We know four of those.
Gary Vaynerchuk
Or have they lived that life? I'm a talking head that only talks about the things that I've lived.
Alvin Bolles
Well, you're a practitioner and an operator and you're translating that to other individuals to bring them into this.
Gary Vaynerchuk
There are many things I wish I was talking about, in fact. So this again makes proof in the pudding. I wish I was deeper right this second because I would be so happy putting out more meaningful content around AI because it would be good for me, my business, my opportunities and the audience. But again, I haven't had the luxury to go as deep as I want.
Alvin Bolles
To, but it's a smart way of doing this. A lot of this is about making sure one, you're testing and test and learn, test and learn, test and learn. But also you, you're listening and this is part of the challenge.
Gary Vaynerchuk
That's the whole game.
Alvin Bolles
And this is when you don't have a galvanized group of individuals, there isn't a community, a safe place to be able to say, I don't know or tell me what you do know. Well, that's one of the things, that's.
Gary Vaynerchuk
Why we love what you're doing. That's like we're trying to. By the way, why do you think I said yes? I love you, I love Stephen. I love you guys.
Alvin Bolles
But like, love you too, bro.
Gary Vaynerchuk
I also really know what you're doing is going to help a lot of my friends and the community.
Alvin Bolles
At the end of the day, what's interesting, like insight, everybody's worrying about, like, is this going to be evil? Is this going to disintermediate people? Is this going to make sure some people going to be obsolete? You know, there's obsolescence, if you will, as associated with this. 100%, of course.
Gary Vaynerchuk
By the way, everything's done that.
Alvin Bolles
Absolutely.
Gary Vaynerchuk
The car did that.
Alvin Bolles
Correct.
Gary Vaynerchuk
Electricity did that.
Alvin Bolles
I didn't walk here. You know what I mean?
Gary Vaynerchuk
Like, and by the way, there was an entrepreneur that bought 10,000 horses the day before Henry Ford's like, you know what?
Alvin Bolles
Right.
Gary Vaynerchuk
That happened.
Alvin Bolles
Correct.
Gary Vaynerchuk
Like, no one's crying for the people. I don't hear anyone when they're like, AI is terrible. I didn't hear any of you when the leading salesperson for the yellow Pages lost her bag. No, I didn't hear from you when you guys. I don't hear from anybody when pop up bagels comes and explodes and a local deli closes.
Alvin Bolles
Correct.
Gary Vaynerchuk
Because they don't sell bagels anymore. I don't see the wah wah. You just like your pop up bagel.
Alvin Bolles
Correct.
Gary Vaynerchuk
Like this. Like, we need to not be delusional.
Alvin Bolles
Correct.
Gary Vaynerchuk
Technology is undefeated. And every time, always and every time something comes up, it changes shit.
Alvin Bolles
But there's a way for it to coexist. I mean, I think about painting and the invention of the camera. It's another canvas in which to paint on. People still paint.
Gary Vaynerchuk
It's always and it's always.
Alvin Bolles
And photography's a wonderful medium for self expression. Both can coexist, but both can actually be in the same gallery and you can appreciate both of them for what they are.
Gary Vaynerchuk
Look, I've been thinking about this for a while now. And I may go there. There is this obsession with the word or when life is about.
Alvin Bolles
And I like that.
Gary Vaynerchuk
You know, And I've been thinking about, like, the concept of, like, the power of.
Alvin Bolles
I may quote you on that one.
Gary Vaynerchuk
Please. I really. It's one that really is like a big observation of my life. I think a lot about, like, why did things work out for me. A lot of improbability to like, you know, my circumstance. Not my macro circumstance of being a male. I mean my micro. Like my truth. The truth of my life. And a lot of it is the obsession of and over or. And I see it in so many others. We are fixated on or we love black and white. Black and white makes people feel safe.
Alvin Bolles
It does.
Gary Vaynerchuk
But life is gray as shit. It's so fucking new. It's why everyone's on tilt right now.
Alvin Bolles
Correct.
Gary Vaynerchuk
It is not blue or red. It's always purple. And when you believe that it has to be blue and. Or red, you're fucked. And that's why everyone's anxious and it's why the pendulum continues to swing. And that's why we canceled very effectively on the left. We're now canceling very effectively on the right. It's such a joke.
Alvin Bolles
That's the reason for our problems. Well, that's not cool.
Gary Vaynerchuk
Once you get to purple.
Alvin Bolles
Yeah.
Gary Vaynerchuk
And the problem is both sides are actually 100% wrong.
Alvin Bolles
Yes.
Gary Vaynerchuk
Like if you're red or blue. If you're black or white, you're 100% wrong. Because it is purple and gray out here. And that's what's gonna happen with AI to leave with one last final point here.
Alvin Bolles
Absolutely.
Gary Vaynerchuk
Just please go into maybe zone. Everybody. I used or. But maybe Zach, ironically, it's maybe that really triggers my success. The power of maybe. I don't say no. Which is why so much good has happened for me.
Alvin Bolles
I would agree.
Gary Vaynerchuk
Saying yes is also delusional. How you lose as well. It's why maybe is so powerful.
Alvin Bolles
That is a fantastic way to end this. Sort of, you know, interesting thoughts around this thing. I think the piece of this is also just getting. Be able to invest some time. And everybody has infinite amounts of time. Right.
Gary Vaynerchuk
This is my brother.
Alvin Bolles
It's so moving. So.
Gary Vaynerchuk
And how can you pontificate if you haven't put in the work?
Alvin Bolles
Correct.
Gary Vaynerchuk
This was so. By the way, this was social. I would talk to CMOs for the last decade. They're talking about things. I'm like, you don't know. You didn't do it.
Alvin Bolles
But think about all the conversations we've had at Cannes. It's like people running around and having these conversations. It's not real unless you've actually put it into practice, learned something, and likely failed at it.
Gary Vaynerchuk
You're basically failing at all times until you're not correct. Life is just like walking and eating. Like, the way we all, like, watch. I wish all of us could watch our videos or our first attempts of walking. It wasn't successful. No, it didn't work out. You know, eating. It was all over our ourselves and in our hair and like, this is life. And it doesn't change from infant to where we are now. And I really, really, really encourage all of you, anyone who's listening right now, that is using this journey and consuming this content. Cause you're in the camp of no AI and going to fear right away. And listen, you and I care about this stuff. But everyone's like, the AI's gonna be biased. I'm like, before you tell me about the world's problems, about race and gender, the world is always gonna have that. Why you have 100%.
Alvin Bolles
That's where you want now.
Gary Vaynerchuk
And I immediately. It's very noble. But you know this. People are posturing to look good.
Podcast: The GaryVee Audio Experience
Host: Gary Vaynerchuk
Guest: Alvin Bolles, General Partner at Alpha
Release Date: April 25, 2025
[00:00] Gary Vaynerchuk:
Gary opens the episode by introducing the topic of AI, emphasizing the importance of understanding and leveraging AI technologies before they become overwhelming. He highlights the conversation with Alvin Bolles, focusing on the dangers of pretending to understand AI versus approaching it with informed curiosity.
[00:26] Alvin Bolles:
Alvin addresses the prevalent issue of individuals feigning expertise in AI, particularly among older, less tech-savvy board members. He points out the fear of disintermediation and the reluctance to admit ignorance, which hampers progress and adaptation to new technologies.
[01:04] Gary Vaynerchuk:
Gary discusses the importance of humility and overcoming insecurity in leadership. He reflects on his own career beginnings in a family business, contrasting it with corporate environments he joined later. Gary emphasizes practical knowledge and human behavior over theoretical or superficial understanding, criticizing those who "peacock" without genuine expertise.
Notable Quote:
"The real answer to the question is good parenting... it's based on the stuff that I do know well, which is human behavior." — Gary Vaynerchuk [01:04]
[03:36] Alvin Bolles:
Alvin concurs with Gary’s observations on authenticity, highlighting that many successful individuals in the marketing industry may overestimate their respectability due to constant self-promotion.
[03:40] Gary Vaynerchuk:
Gary warns against the pitfalls of building a personal brand without substance, noting that true respect comes from genuine expertise and contributions rather than superficial self-promotion.
Notable Quote:
"There are a lot of people that are wildly successful in our industry... not as respected as they think they are because they are constantly bullshitting." — Gary Vaynerchuk [03:40]
[04:21] Gary Vaynerchuk:
Gary shares his proactive approach to AI, contrasting it with others who either fear it or remain superficial in their understanding. He stresses the importance of using AI tools daily and encourages listeners to experiment and integrate AI into their workflows.
[06:30] Gary Vaynerchuk:
He recounts an anecdote about encountering older professionals advocating for ChatGPT over traditional search engines like Google, illustrating the rapid adoption and impact of AI technologies.
Notable Quote:
"The day I heard about midjourney, I used it. Let me see how to make a picture in a video. Absolutely day perplexity like I'm doing it, I'm using it." — Gary Vaynerchuk [04:22]
[07:13] Gary Vaynerchuk:
Gary emphasizes that most people in leadership are not practitioners and lack hands-on experience with AI platforms. He urges listeners to "download all of them and play with all of them" to gain practical understanding and context.
[08:11] Alvin Bolles:
Alvin reinforces the need for practical experimentation, advising listeners to invest time in testing and learning through direct interaction with AI tools.
Notable Quote:
"And this is when you don't have a galvanized group of individuals, there isn't a community, a safe place to be able to say, I don't know or tell me what you do know." — Gary Vaynerchuk [09:23]
[10:12] Gary Vaynerchuk:
Gary draws parallels between past technological shifts (e.g., the advent of cars and electricity) and the current AI revolution, asserting that society rarely laments the obsolescence caused by new technologies.
[11:11] Gary Vaynerchuk:
He likens AI to photography in the art world, suggesting that new technologies create new avenues for expression rather than eliminating existing ones.
Notable Quote:
"Technology is undefeated. And every time, always and every time something comes up, it changes shit." — Gary Vaynerchuk [10:53]
[11:23] Gary Vaynerchuk:
Gary critiques the tendency to view issues in black and white terms, advocating for recognizing the complexities and "gray areas" inherent in life's challenges, including AI.
[12:14] Gary Vaynerchuk:
He introduces the concept of "maybe," highlighting its power in fostering open-mindedness and flexibility, which are crucial in navigating the uncertain landscape of AI advancements.
Notable Quote:
"Life is gray as shit. It's so fucking new. It's why everyone's on tilt right now." — Gary Vaynerchuk [12:19]
[13:17] Alvin Bolles:
Alvin underscores the importance of investing time in understanding AI, reinforcing the episode's central message of proactive learning and adaptation.
[13:52] Gary Vaynerchuk:
Gary likens the process of mastering AI to learning fundamental life skills like walking and eating, emphasizing that failure is an inherent part of the learning journey.
Notable Quote:
"Life is just like walking and eating. Like, the way we all, like, watch. I wish all of us could watch our videos or our first attempts of walking. It wasn't successful. No, it didn't work out." — Gary Vaynerchuk [13:52]
Gary and Alvin conclude the episode by reiterating the necessity of embracing uncertainty and adopting a "maybe" mindset. This approach fosters resilience and adaptability, enabling individuals and organizations to thrive in the fast-paced AI-driven world.
Final Notable Quote:
"Maybe is so powerful... That's why maybe is so powerful." — Gary Vaynerchuk [12:58]
Authentic Engagement with AI:
Avoid superficial understanding; engage directly with AI tools to gain practical experience.
Humility and Continuous Learning:
Leaders should embrace humility, admit knowledge gaps, and commit to ongoing education in AI.
Rejecting Binary Thinking:
Embrace the complexities and nuances of AI, moving away from black-and-white perspectives.
Adopting a "Maybe" Mindset:
Cultivate flexibility and openness to navigate the uncertainties of technological advancements.
Historical Context of Technology Evolution:
Recognize that technological disruptions are inevitable and focus on how to adapt rather than resist.
This episode serves as a compelling guide for professionals seeking to navigate the rapidly evolving AI landscape. Gary Vaynerchuk and Alvin Bolles provide insightful discussions on authentic engagement, the importance of continuous learning, and the necessity of embracing complexity in the age of artificial intelligence.