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Episode 1347 · Sep 1, 2026

The AI Advantage You Can’t Buy with Adrian Rosebrock

Adrian Rosebrock
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Most businesses have already "adopted" AI. They have the accounts, the prompts, maybe a power user or two doing impressive things with Claude Code. And almost none of it gives them an edge, because everyone else has the exact same tools for twenty dollars a month. On this episode of The Daily Mastermind, George Wright III sits down with Adrian Rosebrock — computer scientist, PhD, investor, and CEO of Chief of AI — to talk about what actually separates companies getting real ROI from AI and companies that are just busy with it.

Adrian's answer is uncomfortable but clarifying: the advantage you can buy isn't an advantage at all. The one worth building comes from your own data, your own processes, and the relationships no model can replicate.

Adrian Rosebrock on Building PyImageSearch and Finding the Signal in the AI Noise

Adrian started as an entrepreneur at 19. He built a couple of apps in college — the first covered his car payment, the second covered rent — and then, during his final year of grad school, launched PyImageSearch. It was an education platform in a very specific niche: computer vision and deep learning, the science of writing software that can see what's in an image. Face recognition. License plate recognition. Self-driving cars.

He understood the theory from his PhD work, but he'd struggled badly with implementation, and he knew he wasn't alone. So he wrote nine books, two courses, and more than 500 tutorials — all by hand, before generative AI existed. PyImageSearch grew into a top-20,000 website worldwide with half a million people on the email list before it was acquired about four years ago.

After the exit, Adrian came back to AI for a simple reason: his friends in entrepreneur communities kept asking him to vet solutions and review roadmaps. They could see AI mattered. They had no idea how to actually deploy it. Chief of AI grew out of those conversations.

The Three Waves of AI Adoption Every Business Leader Should Understand

Adrian frames the whole market in three waves. Wave one — access, roughly 2022 to 2026 — measured success by adoption. How many people on your team are using AI? Wave two — economics, roughly 2025 to 2028 — asks harder questions: what does this actually cost, what's the ROI, and what's our governance policy? Wave three — differentiation, which he estimates runs 2028 to 2032 — is where proprietary data and custom models decide who wins.

There's no moat around a $20 a month account. You have to be looking internally: what's your competitive advantage, what are you doing that no one else can, and start engineering your AI efforts surrounding that.

Why Tokenomics Is Becoming a Real Business Risk

Adrian cited financials showing OpenAI with roughly $3.7 billion in revenue against about $12.5 billion in expenses — numbers that can't hold forever. Providers can raise token prices eight to ten times overnight, and if you've built your business model on cheap inference, that's a company-ending event. George compared it to building your entire business on a social platform that can pull your page. Some organizations are now buying token futures to lock in costs, the same way an industrial operation hedges oil.

How Bridgewater Built a Real AI Moat With Proprietary Data

Adrian's favorite example of wave three is Bridgewater. The hedge fund has recorded internal conversations and documented the reasoning behind investments for years — so when large language models arrived, they already owned a treasure trove of proprietary data. Team members prompting an off-the-shelf model got about 50% accuracy, a coin flip. Expert-written custom prompts pushed it to 60–70%. Then their AI team fine-tuned a model on Bridgewater's own dataset and accuracy jumped past 80%. Better still, because they could self-host that model, token costs dropped by 14x — independent of OpenAI, Anthropic, or Google, and immune to overnight pricing changes.

When to Buy, Modify, or Build AI in Your Business

The number one question Chief of AI gets is simply: where in my business should AI go? Adrian answers with a two-by-two grid — degree of differentiation on one axis, degree of risk or consequence on the other.

Low differentiation, low risk? Buy off the shelf. Low differentiation, high risk — a CRM, for example? Still buy, because nobody should be maintaining a custom CRM. High differentiation with moderate risk — say, a lender's unique underwriting process — is the modify zone: find something that gets you 70–80% of the way there, then customize with code and API integrations. Only in the upper-right quadrant — extremely differentiating *and* extremely high consequence if you get it wrong — do you spend the time and money to build from scratch. That's where the proprietary moat lives.

Why AI Should Optimize the Back Office, Not Replace Human Relationships

Starting with hours saved is fine, Adrian says, but it's where everyone starts and it won't serve you long-term. His deeper argument is mathematical: a large language model is trained on the average of the internet, and every response is an average drawn from those weights. An average of an average reduces variance. That's why so much online content now sounds identical — and why your brain has learned to tune it out.

George offered a live example. The Daily Mastermind receives hundreds of interview pitches. Detailed personalization used to signal real effort. Now every pitch is detailed, every pitch is "personal," and all of it gets filtered out. Volume killed the very thing that made it work.

We live in the most technologically advanced time in our world, but yet we all suffer from this deep loneliness.

The companies that win, Adrian argues, will use AI to strip repetitive back-office work off employees' plates so those people can spend more time building real relationships with customers. A real human on the phone, at the end of the chatbot, writing the email — that becomes rarer, and therefore more valuable, every year.

The Boring Mistake That Creates Real Liability: AI Governance

The biggest mistake Adrian sees isn't technical — it's governance and policy, precisely because it's boring. He described a Midwest bank where an employee, not doing anything nefarious, uploaded personally identifiable information to ChatGPT. The bank had to self-report the violation. Studies he's seen suggest 50–60% of CEOs believe their employees have uploaded sensitive information to these tools, knowingly or not.

His fix is a three-step process: write real policies with your lawyer and stakeholders, then educate employees on the dos, don'ts, and consequences; monitor network traffic and file names at the firewall or VPN level for larger organizations; and, in a Google or Microsoft environment, prevent downloads to local disk so files stay inside permissioned cloud folders. None of it eliminates risk — all of it makes a bad outcome dramatically less likely and your position defensible.

Action Steps

  • Map your AI opportunities on the differentiation-versus-risk grid before spending a dollar. Buy the commodity, modify the semi-custom, build only the high-risk, high-differentiation work.
  • Audit your token spend and ask what happens to your margins if prices jump 8–10x.
  • Start capturing proprietary data now — decisions, conversations, reasoning — so you have a dataset worth fine-tuning on in three years.
  • Write and circulate an AI usage policy this quarter, including what employees may never upload and what the consequences are.
  • Redirect the hours AI saves into face time with customers, not into producing more automated noise.

Use AI to build proof of concepts fast, Adrian says — just don't confuse a proof of concept with something production-ready. The real leverage isn't replacing people; it's freeing them. And it's never too late to start living the life you were meant to live.

About the guest

Adrian Rosebrock

Adrian Rosebrock — CEO, Chief of AI. PhD in computer science and artificial intelligence. Founder of PyImageSearch, the world's largest computer vision education platform (acquired 2021). He now leads a fractional Chief of AI team that helps organizations get a real return on their AI investment.

READ THE FULL TRANSCRIPT

[00:00:00] [00:00:05] All right, guys, welcome back to The Daily Mastermind. [00:00:10] George Wright III with your daily dose of inspiration, motivation, and education. And I'm excited to be [00:00:15] on the podcast today with Adrian Rosebrock. Adrian, how you doing? Adrian Rosebrock: I'm doing wonderful, George. [00:00:20] Thank you so much for having me George Wright III: Yeah, I'm glad we could line up. Guys, if you are looking at AI, [00:00:25] trying to use AI, you're dealing with it, whether you're a small, medium, or large business, we're gonna be talking about some [00:00:30] really good stuff today because there's a lot of hype out there in the industry when it comes to AI, [00:00:35] and you need to know what to do, when to use it, where the ROI is and what to think about if you're [00:00:40] trying to decide whether to buy solutions or create solutions. So let me give you a quick background on [00:00:45] Adrian. Computer scientist, entrepreneur, AI architect, investor. He's [00:00:50] the CEO at Chief of AI, the company. But he built Pie Image Search into a [00:00:55] leading computer vision and deep learning education platform that was acquired [00:01:00] recently a few years back. But now he helps organizations move past this AI [00:01:05] experimentation mode into actually getting an ROI and using it. And so this topic is [00:01:10] one that I think I've really vetted individuals that know what they're doing, and that's why, Adrian, I wanted to [00:01:15] bring you on the podcast. So I really appreciate you being here and I would love it if you just, before [00:01:20] we got into AI, told me a little bit of the background you had with your acquisition and with Pie Image, [00:01:25] 'cause it it helps people to understand where you came from and, why your knowledge is what it is Adrian Rosebrock: [00:01:30] Totally. Yeah. I always tell people I started as an entrepreneur when I was 19 years old, and I [00:01:35] built a couple apps in in college. The first one made enough to make my car [00:01:40] payment, the second one made rent, and the third one is the one that really took off. So during my final [00:01:45] year of grad school, I started PyImageSearch which is effectively an, an info product, [00:01:50] but in a very specific niche of computer vision and deep learning. So imagine [00:01:55] writing software that could see what is in an image, like face recognition, self-driving [00:02:00] cars license plate recognition. This is all stuff I did for my PhD, so I understood the [00:02:05] theory behind it, but when I was just getting started, I really struggled with the implementation, with the [00:02:10] experimentation, writing the code to actually do the thing. And I wasn't alone. Other [00:02:15] students, other researchers, other developers in, in the enterprise world were also struggling with this. [00:02:20] So I set out to, to fix that problem. I wrote nine books, two [00:02:25] courses, 500 and some tutorials, before generative AI was a thing. So all of this was written by hand [00:02:30] and grew PyImageSearch into a, a very large website top 20,000 website in the world [00:02:35] when it was acquired about four years ago, half a million people on the email list. So it was pretty [00:02:40] substantial for what it was. And then after it after it was acquired, I, started teaching myself [00:02:45] some some other topics just for fun, did some self-improvement, but ultimately came back to AI 'cause [00:02:50] I, I could see entrepreneurs, I could see business owners struggling, finding the signal through the noise, trying [00:02:55] to recognize what's true and what's overblown hype. George Wright III: Yeah. It's [00:03:00] interesting. You seem to have followed areas that you're passionate about, which is the journey of a lot of [00:03:05] successful entrepreneurs. And of course, AI is pretty big right now, but what [00:03:10] really made you decide to go down the path and really get deep in, in AI and create [00:03:15] this company around Chief of AI? Adrian Rosebrock: It was honestly working with my friends. I [00:03:20] belong to a number of entrepreneur membership communities, and just due to my background, people would [00:03:25] come to me and ask me questions about AI, what they shouldn't do, ask me to vet solutions [00:03:30] or look at kind of roadmaps of where they were going. And this was even before I had started Chief [00:03:35] of AI. As soon as Chat GPT came out this started happening where these business owners, they were [00:03:40] recognizing, "Hey, we need to get AI into our business." They could see the importance of it, but they had no idea [00:03:45] how to actually go about doing it. So it just started off naturally, me helping out my [00:03:50] friends, wanting to see my friends succeed. And then over time it evolved as [00:03:55] AI evolved into more of this small-medium business enterprise [00:04:00] solution business where we're actually helping people from the ground up actually architect AI [00:04:05] solutions. And not just around building workflows or giving you prompts, but understanding the [00:04:10] privacy concerns, the policy concerns, how you actually architect the data, how do you build data sets for your [00:04:15] company? How do you train custom models that gives you an actual, real proprietary [00:04:20] lift in your business? George Wright III: Yeah, there really is so much information out there, but I [00:04:25] think one of the challenges a lot of businesses face is that it comes along with this idea that [00:04:30] because it's AI, you can figure it out yourself. And so it's a pro and a con. [00:04:35] And so with all the hype around AI, I wanted to ask you, where do you believe business [00:04:40] leaders really should be focusing, and where do they start? Because you talk [00:04:45] about, I know that there's, architecting solutions versus, buying [00:04:50] products and subscribing to, systems and software products with AI. Where do you get most [00:04:55] businesses to start, and where should they be focusing? Adrian Rosebrock: It's a great question. I explain [00:05:00] this to people as looking at where AI adoption currently is and where it's [00:05:05] going. There are three waves if you look at this. The first wave AI access is like [00:05:10] 2022 to about 2026, where the primary adoption metric has [00:05:15] been, how many people are using AI within your organization? Do you have, ChatGPT accounts? Do you [00:05:20] have Claude accounts? Maybe you have some some power users on your team have Claude [00:05:25] Code or Claude CoWork set up and they have some custom skills. Maybe you're sharing some skills back and forth [00:05:30] betwe- between your team. But the primary success metric here is adoption. How many [00:05:35] people within your organization are using AI? The issue here though, especially moving [00:05:40] forward, is that there's no moat surrounding your business whatsoever. Anybody with 20 [00:05:45] bucks a month spend can get access to Claude or ChatGPT, have access to the exact same [00:05:50] models that you have. Now we're starting to shift more into wave two, which is about the [00:05:55] economics, which is about 2025 to 2028, which isn't honestly that, that far [00:06:00] away. And now we're starting to understand like the actual cost. What's the ROI? Are [00:06:05] we getting real value out of that? And also what's the governance and the policy surrounding these things? [00:06:10] And starting to look at the real unit economics of this. So in April [00:06:15] 2026, OpenAI was showing some financials that demonstrated they had about [00:06:20] 3.7 billion in revenue, but cost them about 12.5 billion in expenses to [00:06:25] actually run and operate. Obviously, that's not a sustainable business, so you have to look at [00:06:30] the, the token economics of how this is even gonna work out at scale. And, [00:06:35] Claude, ChatGPT, these companies can eight to 10X your token price over- [00:06:40] overnight, which can completely blow your entire business model if you're, have a lot of token [00:06:45] spend. So that's where George Wright III: if you build your business around it, right? If you're building your business around it now thinking it's [00:06:50] working, and by the way, not even looking at the economics and they start to scope creep on you, [00:06:55] and then all of a sudden something changes, it's like building your whole business around social media and having them pull your page, [00:07:00] right? Adrian Rosebrock: Exactly. Exactly right. And that's why tokenomics is this brand new [00:07:05] idea and thing to consider where businesses are literally purchasing token futures so they can lock [00:07:10] in their token costs for the next few years. Just as you, if you're running like a, a- an industrial [00:07:15] operation, you might wanna purchase oil futures so you know what your true oil costs are gonna be.[00:07:20] Tokenomics are also becoming very much a thing to consider and with that, [00:07:25] where we're going and I think is the most important part to focus on is this wave three or what I [00:07:30] call the, the differentiation period. And that's, I estimate 2028 to 2020-- 2032. [00:07:35] And here we focus exclusively on the proprietary capabilities the competitive [00:07:40] advantage of actually using AI within your business. And my favorite example of this [00:07:45] is the hedge fund Bridgewater. Bridgewater is known for having [00:07:50] recorded like all of their internal conversations, every investment they've made, they have a detailed paper [00:07:55] trail of why they made certain decisions. So when, large language [00:08:00] models became prominent and useful, Bridgewater had this treasure trove of dataset of a dataset [00:08:05] already available to them. So they built a dataset that the goal was to help to create an AI [00:08:10] model to help their team members make smart decisions for the company. So [00:08:15] they focused exclusively at least initially on their investments, and they trained or [00:08:20] they they just gave gave the model to their team members and just started...[00:08:25] They said, "Start prompting this thing, and we'll measure the accuracy and the quality of the [00:08:30] results that we get." And they got about 50% accuracy, about a coin flip not very good. [00:08:35] Then they handed this over to their engineers and said, and their investors, and they say, "Tune these and [00:08:40] write custom prompts for us, like expert written prompts. Let's see what type of accuracy we can get [00:08:45] off of that." Accuracy jumps to 60, 70%. And then they go into their AI [00:08:50] team and they say, "Okay, take this dataset and just [00:08:55] fine-tune a large language model, custom train it on our dataset." And when they did that, they [00:09:00] measured the accuracy over 80%. And what's even more interesting is that their [00:09:05] token cost dropped by 14X because they were able to self-host their model [00:09:10] independent of ChatGPT, independent of Anthropic and the Gemini, the other players. So they [00:09:15] have this self-hosted sovereign model that doesn't update Claude and ChatGPT [00:09:20] will at a whim. Like that they control the token cost on, and it's beating, [00:09:25] just copy pasting prompts and skills into into a large language model. Now [00:09:30] Bridgewater has a true proprietary lift because n- very few hedge funds, [00:09:35] especially not to the degree that Bridgewater does have access to these types of datasets, and now they've [00:09:40] trained the custom model on top of that. That is where AI is gonna be going in the [00:09:45] next five years. Because again, there's no moat around a $20 a month account. You [00:09:50] have to be looking internally, what's your competitive advantage? What are you doing internally that [00:09:55] no one else can? And start engineering your AI efforts surrounding that. George Wright III: Yeah, you [00:10:00] actually said some things that really resonated with me, which is a moat around your business. Obviously when you [00:10:05] do that, but when you combine it with a competitive advantage, because most people are utilizing some of the same [00:10:10] stuff, and they will, but when you have proprietary information and you build it the right way, [00:10:15] it not only creates a moat around your business, but you get a distinct competitive advantage. And like we're starting to [00:10:20] use more agentic sites with some of our stuff that we're doing. We're not really necessarily [00:10:25] containing that, and I think our token cost needs to be looked at as well. But as you start [00:10:30] to do that in a in a system that can [00:10:35] self-evolve, the accuracy and the ROI grows [00:10:40] substantially versus just constantly using the tool, right? So we've had the same thing happen where, [00:10:45] individuals in our company, we want them to be using AI, but when we start to collaborate around AI [00:10:50] operating systems, they get even more productive because now the learning is collaborative. But then [00:10:55] I could see what you're saying when a business starts to build an infrastructure or moat or [00:11:00] even operating system around their system. You gotta build that, right? So I guess the [00:11:05] question for me would be, should you build something or should you buy [00:11:10] solutions? And you talk a little bit about this, so tell me what your philosophy is on that. Adrian Rosebrock: Yeah, [00:11:15] so whenever we talk to a potential client or a client, we're trying to help them out and [00:11:20] evaluate where they should apply AI into their business, which by the way, is the number one question we [00:11:25] get. Where in my business should AI go? We tend to just show them this, this [00:11:30] two-by-two grid where on the X axis we'll say, "What's the degree of differentiation to [00:11:35] your business?" Does every business run this like a CRM or, employee payments? Or is this [00:11:40] something highly differentiated to your business specifically? And on the X axis, we'll [00:11:45] say, "What's the degree of consequence or the risk?" If we, if you get this right, if you get this [00:11:50] wrong, what are the consequences? And if you plot this out, what you'll see is most of [00:11:55] the time you're gonna buy something off the shelf. If there's no [00:12:00] differentiation and there's very little consequence why would you build that? That's not a good use of money. You're gonna buy it off the shelf. [00:12:05] If there's little differentiation, but there's high risk and a good example like this could [00:12:10] be a CRM. Nobody wants to build and maintain their own custom CRM. That's a lot of work, but [00:12:15] it's very important to your business, and risk of getting it wrong, typically very high. So again, [00:12:20] you're gonna go buy off the shelf. Now, let's say like you're run- you're writing or running this [00:12:25] underwriting company where you offer loans to individuals or businesses, and you have a very specific [00:12:30] underwriting process. That underwriting process, that's a very intense degree [00:12:35] of differentiation. Very little people are going to be doing it the way you are. So now we're getting into a [00:12:40] little interesting area of the world where you're like do I buy off the shelf?" [00:12:45] Probably not, because nothing is really gonna serve what you need for your specific use case. But you should [00:12:50] first do your research, see what's out there. Can you find a solution that could get you 70, [00:12:55] 80% of the way there? And then we just have to modify a little bit. Maybe we write a little bit of code, write some [00:13:00] API integrations, try and get you most of the way there. It's only in this upper [00:13:05] right quadrant where something is extremely differentiating to your business and the risk of [00:13:10] getting it wrong is extremely high. That's the quadrant where you're gonna spend, the [00:13:15] effort, the time, the money to say, "Okay, we need to build this from scratch," because that is where [00:13:20] that true proprietary moat is gonna come. And again, like when we look forward to, [00:13:25] 2020 and beyond, companies that do the, the build to win approach for their high risk, [00:13:30] high differentiation, they're gonna be like Bridgewater. They're gonna have a actual real moat [00:13:35] surrounding their business. George Wright III: I love the way you said that and just for my purposes, maybe for the listeners [00:13:40] to clarify, you're talking about with the AI specifically. So if you have a high degree of [00:13:45] risk of getting it wrong and you really clearly wanna differentiate, this is where you [00:13:50] build, and this is where you build custom solutions basically. But the other areas would be, [00:13:55] can you buy a solution off the shelf, or can you buy a solution and modify it so that you can [00:14:00] definitely differentiate, but you really don't wanna get that, that process wrong? And I [00:14:05] would imagine that maybe some businesses, this would morph maybe over time or [00:14:10] as they develop more and more but this really does answer the question [00:14:15] of or at least the process of this, of where to deploy it, right? Because one of the things I was wondering, and I was gonna ask you, is [00:14:20] how should a company really identify the area to start with where [00:14:25] there's the most measurable ROI? Is it always to start with r- replacement value of [00:14:30] productivity, or is it to focus on the highest ROI first to [00:14:35] drive the metrics in the business and then come backfill it with productivity? What are your personal [00:14:40] thoughts on that? Adrian Rosebrock: That's a great question. I think focusing on productivity or hours [00:14:45] saved is a good place to start, but it's where everyone else starts, and I don't think [00:14:50] it will serve you in the long run. So my personal belief is that [00:14:55] the more and more AI gets integrated into our daily lives, the, the more [00:15:00] we see AI-generated text on Facebook, on LinkedIn, the more our brains [00:15:05] tune it out as just noise. It's like, we see it all the time on LinkedIn, low-effort posts [00:15:10] written with AI just makes you wanna just roll your eyes and move on. It's like this person couldn't [00:15:15] be, They, they-- Not only could they not be bothered to write it by hand, but they couldn't even take the effort to [00:15:20] use AI to make it interesting George Wright III: Yes. Adrian Rosebrock: So why... Let's zoom out for a second. [00:15:25] Why does that happen? A large language model is trained on effectively the entire [00:15:30] corpus of human information most of the internet. And when you train a model [00:15:35] in that way, n- it becomes an average of the homogeneity of this internet. [00:15:40] And then when you go and write a prompt and you get a response back, that's another average based off [00:15:45] of the weights of the model at runtime. So you get an average of an average, and for [00:15:50] your mathematically inclined or statistic-friendly people, listeners, what's an average of an average? It [00:15:55] reduces the variance. So your output actually shrinks, yeah, [00:16:00] significantly. So now everything is starting to sound the same. And again, I'm sure, Jordan you've [00:16:05] encountered this. Your listeners have encountered this. You're like, "Wow, the internet sounds like the same now. Everybody sounds [00:16:10] the same." It's because of everyone using large language models. [00:16:15] So It's my personal belief that if you want to use AI within [00:16:20] your business, use that more in the back office. Use it in ways that can [00:16:25] optimize your underlying processes. Use it in ways to increase your your [00:16:30] proprietary moat. What you shouldn't do is use AI excessively in [00:16:35] user-facing interactions, because those are gonna g- become more and more [00:16:40] rare and therefore more and more important and e- and then the most [00:16:45] differentiating factor with, within why someone would choose to go to your business versus a competitor. [00:16:50] It's because there is a real person on the phone. There is a real person at the end of the [00:16:55] chatbot. There is a real person who's typing that email to you. Maybe they're using AI [00:17:00] to assist, to pull knowledge from the knowledge base, but there is a real human being there. [00:17:05] So if the user has a problem, they will know there is a person there. So my [00:17:10] personal opinion is that if you wanna be successful with AI, don't use it to [00:17:15] replace all of your using-- user-facing interactions. I think that's actually how you hurt your business in the [00:17:20] long run. Instead, start looking at it as how can I start [00:17:25] optimizing and removing repetitive, boring tasks from my [00:17:30] employee's plate such that they can spend more time with the c- with our customers [00:17:35] to develop more face time with them, to develop actual, real relationships with them. [00:17:40] We live in the most technologically advanced time in our world, but yet [00:17:45] we all suffer from this, this deep loneliness. [00:17:50] So what's the solution moving forward? The companies that will be successful, the individuals that will be [00:17:55] successful will be the ones who learn how to nurture these relationships [00:18:00] while optimizing the other aspects of their business using artificial intelligence. George Wright III: that is so [00:18:05] critical. I'm a big believer in that, and I give you a very tangible example. It's like [00:18:10] I think a lot of people start with the intent of increasing their productivity, but then they think [00:18:15] geez, if I could do it in half the time, why don't I just do more of it?" Case in point, at The Daily Mastermind, [00:18:20] we receive hundreds of requests to be interviewed at any given time. [00:18:25] And, in the beginning, it would be like, "I listened to your episode, and I heard an amazing [00:18:30] topic, and, I've got a couple ideas, and I'd love to talk with you." And you're like, "Wow, this person really spent some time." [00:18:35] Now, because of AI, everyone says that, and they have extreme detail. [00:18:40] But what's happened is I get now more requests, and they're all personalized, and [00:18:45] it's basically cold email coming to me now that looks extremely personal, so I just tune [00:18:50] it all out. In fact, we send it through filters now of filters. And so I think people think, "Oh, it's gonna [00:18:55] increase my productivity," and they're like man, I could do 100X more of these," and what they realize is that [00:19:00] personalization is no longer personal, and so they're doing it wrong. Now, if you can increase your productivity [00:19:05] to spend more time in your unique talent doing what you do great with relationships, now you can spend more time [00:19:10] with relationships 'cause you don't have to do the busy work. That's an effective use of it. So I'm a [00:19:15] big believer in what you're saying, and I think when it comes to ROI, it is a bit of a mix because [00:19:20] I know that if I innovate with AI, it might create a large [00:19:25] ROI, and then I've got this little save me a little bit of time thing. And so I think it's a [00:19:30] balancing act, obviously. But you guys at your company Chief of AI i'm sure that when you [00:19:35] architect solutions for businesses, you have to look at all these levers, right? Adrian Rosebrock: [00:19:40] Absolutely. And it's worth noting, it's like we, we are an AI [00:19:45] company, but I joke with, the team members and our clients. It's like we're actually the, company. [00:19:50] We don't really wanna sell you a workflow or a set of prompts or to come into your business and sit [00:19:55] next to you and watch you work and figure out how to optimize everything. That's what AI was, but it's not [00:20:00] where it's going. We're much more interested in yeah, sure, understanding where the key [00:20:05] areas of your business are, but understanding where that true proprietary advantage is, understanding how [00:20:10] we can create AI solutions that leverage that proprietary advantage. We're not [00:20:15] here to sell you some workflows and then leave after that, because I think there is a huge [00:20:20] disconnect between the founder, the C-suite, the, the stakeholder mindset and [00:20:25] your employee mindset. For people who have a very owner [00:20:30] mindset, they look at productivity and they'll be like, "Oh man I just got this task done in 10 [00:20:35] minutes. It used to take me two hours. Look how much more productive I am. Now I can do all these other tasks." [00:20:40] Whereas someone down, farther down the food chain in the, the business, they might not have [00:20:45] that ownership mindset. They may be a very good worker, but they're looking at it as "Wow, this [00:20:50] only took me 10 minutes. It used to take me two hours. Great. I'm can go hang out with my [00:20:55] family right now." And that's-- Right? So it's and there's nothing wrong with that mindset either. In fact, I'd [00:21:00] encourage that, that mindset. But just realize that, if you're a key stakeholder in the business, you're [00:21:05] more likely to want to optimize, optimize. Whereas, just your typical nine-to-five [00:21:10] employee, they just wanna do their job, do it well, get paid, and go home. [00:21:15] There's-- The incentive isn't there to optimize every ounce of the minute, every minute [00:21:20] of every day, which typically if you're an entrepreneur that's more of your mindset. George Wright III: Yeah, I think it's [00:21:25] the difference between dropping a really cool tool into the team and [00:21:30] architecting your company's vision and strategies around it so [00:21:35] that we're saying, "Okay, we're doing this with a purpose to optimize for more results," and then it grows [00:21:40] you, grows us, grows everybody. And I think you used a co- you used it a couple times, the term leverage. I really [00:21:45] like the idea because I've... Originally you start of it and think, it's like replacing a [00:21:50] task with a robot versus having a robotic arm or something. It's like [00:21:55] where you can say, "Now I'm augmented to where I can be super..." When I use that to augment my [00:22:00] own talent and skills, it's different than replacing talent and skills because now you're still [00:22:05] maintaining that individuality, but also just getting more productive and more ROI. So I really like [00:22:10] that. Do you see some... 'Cause you work with a lot of businesses, do you see what are maybe some of the biggest [00:22:15] mistakes that people are making with AI? And what comes to mind for me as you and [00:22:20] I talked for just a minute, because I have a pretty great relationship with a banking institution, [00:22:25] and we're doing a lot of media work for them and helping them to incorporate some things, and it brought up a an example [00:22:30] you gave of where there's some mistakes might have been made in banking. But give me some ideas that these [00:22:35] are topics around AI that you don't normally think about, but that you should start [00:22:40] thinking about and you're making mistakes with. Adrian Rosebrock: The, the biggest one is [00:22:45] governance and policy. And for good reason. It's governance and policy, it's so [00:22:50] boring. Like it's not a cool flashy demo of AI doing something amazing and [00:22:55] sexy for your business. It's not this great, product shot commercial that gets you [00:23:00] sold and amped up on wanting to go and do that thing. Like governance and policy is, that's admin work, that's [00:23:05] HR work. It's, there's so many things rolled up into one and it's just tedious and boring. [00:23:10] But the problem is that is exactly where if you're running a, a large [00:23:15] organization, where you need to spend that time because you can become liable for it. The, the example [00:23:20] we were talking about offline was this bank in the Midwest. They had an [00:23:25] employee who was, not doing anything nefarious, just wanting to get their job done. They uploaded [00:23:30] some sensitive information, some personal identifiable information to ChatGPT, [00:23:35] and obviously broke broke a lot of compliance rules in the process. The [00:23:40] bank had to report, self-report to the SEC regarding this violation. First time it's ever [00:23:45] happened in history due to this example. And I've seen studies that suggest that 50, [00:23:50] 60% of CEOs believe their employees have uploaded sensitive [00:23:55] information to these tools, either knowingly or not George Wright III: Yeah, and it's it's [00:24:00] interesting because you don't... It's one of those topics, it's like taxes. People just, [00:24:05] it's a boring topic, people don't wanna think about it, but if you're an active investor, you realize that taxes can [00:24:10] completely compound and change your ability to invest if you just put a little effort into it.[00:24:15] But this is one of those things, compliance, governance, policies you don't think about, number [00:24:20] one, because it's boring, but number two, because you just don't think about. You don't know if your [00:24:25] employees are using this stuff, just trying to be more productive and help the business, but uploading sensitive [00:24:30] data, uploading proprietary information, and so there's a lot of that. How do you [00:24:35] correct that? Is that just a process of architecting governance and compliance into [00:24:40] your overall business policies? What do you do with companies to help with that? Adrian Rosebrock: It's a, [00:24:45] to start it's a three-step process. The first thing you do is work with your lawyer, [00:24:50] work with your stakeholders, and you come up with your policies and rules of what happens [00:24:55] and what the consequences are. And then you inform George Wright III: by the way, with AI never really existed before. So these are things you [00:25:00] have to think about, not like what are our terms and conditions. You have to like creatively think of this probably, right? Adrian Rosebrock: [00:25:05] Exactly. You need to sit down and really think of the use cases how people could be using AI within your [00:25:10] team and mark off what is allowed versus not. You need to circulate to your [00:25:15] employees. There needs to be a bit of education surrounding your employees over the dos and do nots [00:25:20] surrounding AI, and most importantly, the consequences of what happens if they break these rules. That's [00:25:25] like step one. You need to get that. That's very defensive for you, so if an employee does something and you [00:25:30] get sued over it, you can at least point to these and saying, "The employee's responsible. We terminated [00:25:35] them." And then that'll help, help... It doesn't eliminate your liability, but it can certainly help your [00:25:40] case George Wright III: Yeah, 'cause intent, bad in- non-compliance or non-policies can comp- [00:25:45] compound the consequences Adrian Rosebrock: Absolutely I can. Absolutely I can. [00:25:50] So that's step one. The next step from there is you, [00:25:55] trying to think how I want to word this properly. Next step is start your [00:26:00] internal team discussions and figure out what what's what you need to do to [00:26:05] interface with your IT department. So this is typically for your much larger [00:26:10] organizations, 100 members, 200 members plus. Start looking at your firewall, your [00:26:15] routing rules, and you can start installing tools that can monitor traffic [00:26:20] in and out to ChatGPT, in and out to Claude. You could set up rules for common file [00:26:25] names that could acci- accidentally be uploaded to to ChatGPT. That way you're scanning [00:26:30] your network traffic for these violations actually happening, so you could step in before [00:26:35] something, something truly bad happens. This actually happened to me, ironically. I I was [00:26:40] working with a financial advisor from a, a large organization and one of their [00:26:45] employees became victims of a phishing attack. And the reason- and the way they were able to figure it out [00:26:50] is because all team members have to VPN through this central server so they can monitor traffic [00:26:55] going in and out. They were able to detect, oh, there was this file name that was uploaded [00:27:00] to, to ChatGPT that shouldn't have been. It was due to this phishing attack. They were able [00:27:05] to pinpoint the exact employee, the exact time that this, this violation happened. [00:27:10] That's another way that you can start looking at this. 'Cause you, you can't tell-- Without doing something like that, you have no [00:27:15] idea George Wright III: You'd never know Adrian Rosebrock: You never know because, someone's on their home laptop, on their home [00:27:20] internet connection, they're at a cafe using the internet connection. They could download anything [00:27:25] and just upload it to upload it to one of these services. George Wright III: Yeah, and you don't know until it's too late, so 'cause you [00:27:30] don't know what you don't know, right? Yeah Adrian Rosebrock: And what's worse is depending on how your [00:27:35] organization's enterprise settings are or the individual's on their individual Claude or ChatGPT [00:27:40] accounts, if you're uploading something via the web interface, that can become training data for the next [00:27:45] model that is released by Anthropic or ChatGPT George Wright III: that's true. So step one would be kinda like [00:27:50] identifying it all. Step two would be like guardrails and systems for compliance and monitoring, right? Adrian Rosebrock: [00:27:55] Yep. And then from there, if you're a Google Drive or a Microsoft shop, I [00:28:00] recommend preventing employees from downloading files to local disk so everything just [00:28:05] goes into an appropriate Google Drive folder and is loaded from there. This helps... It does, again, it [00:28:10] doesn't eliminate data being uploaded to, into a large language model, but it makes it [00:28:15] significantly harder, and it allows you to control file permissions folder permissions at an [00:28:20] enterprise level George Wright III: Oh, I love it. I love it. No, this is really good, and this topic was very important for me to [00:28:25] mention because I really feel like there's a lot of uncertainty. Even though there's a lot of hype around [00:28:30] AI, there's a lot of uncertainty, and that can be really clearly coming [00:28:35] from compliance liability, governance, and so I think that's important. [00:28:40] Last question I had for you is, how do you see AI changing the roles of [00:28:45] founders, entrepreneurs, and business leaders over the next, few years? Adrian Rosebrock: That's a great [00:28:50] question. Honestly it ties back to what I said earlier. It l- it allows people to [00:28:55] experiment faster, build proof of concepts especially for entrepreneurs who typically [00:29:00] neurodivergent in some way, ADHD or autistic, we're bouncing around all over the place. It's nice to be able to [00:29:05] create a proof of concept, translate that to a demo, and then hand it off to a team member, be like, [00:29:10] "Okay, now go and build this." Versus trying to have explain yourself and invest all this time and effort. It allows [00:29:15] you to take-- go from idea to proof of concept really quickly. Now, the trick [00:29:20] there is don't think that your proof of concept is production ready. Don't buy, code it, push it [00:29:25] online. That creates a lot of security risks. But it does allow you to be a bit more [00:29:30] creative and explore that yourself. And the other most important area I would say that I see AI [00:29:35] changing our lives for business owners is it gives us more time to build the human capital [00:29:40] relationships. Human capital is always, at the end of the day, been the core of a [00:29:45] business. It's the relationships you, you build with others, the agreements of this is what we're exchanging in [00:29:50] value for money. It's gonna become even more important with AI because we'll be able to automate more and [00:29:55] more tasks, do things more efficiently. So the reason why you would do business with so- [00:30:00] with an organization versus another one actually doesn't-- has little to do with the organization. It has [00:30:05] to do with your personal relationship to one or more people over there. That is why you're going to [00:30:10] make that business decision. So as you look for ways to AI to improve your life, to [00:30:15] automate your life by all means explore that, be curious, but try and focus on ways [00:30:20] that you can actually get more relationship value, and real authentic [00:30:25] relationship value, not, posting on Facebook or Instagram, but real in-person [00:30:30] relationship capital goes so farther than anything digital these days. George Wright III: Yeah, I love it. When you [00:30:35] go hand in hand, I think then you're really truly getting the benefits of AI, not just productivity. Man, I [00:30:40] appreciate the, the insights. There's a million more questions I could ask you, but for the sake of time, Adrian, I appreciate [00:30:45] you being here. And what's the easiest way or best way for people to connect with you, check out the [00:30:50] company, learn more about Chief of AI or keep tabs on the kind of great content that you're putting out? Adrian Rosebrock: [00:30:55] Just head to chiefofai.com. We're happy to talk to anyone who has any questions about [00:31:00] AI. We have a form there to book a call with us, and we'd love to get to know you George Wright III: Cool. Great. [00:31:05] All right, guys. Listen, if you're listening to this, I hope this has opened your eyes to a few things, given you a few ideas and [00:31:10] strategies, and I wanna be able to hear from you, so hit me up on The Daily Mastermind. Let me know what you're working on, what you're struggling [00:31:15] with, the things you're learning about AI, and what you wanna hear more about. We really look forward to [00:31:20] interacting with you, and make sure you share the show. That helps us grow the community, the network, [00:31:25] and that's what we're all about. So keep in mind and as I always say, it's never too late to start creating the [00:31:30] life, the business, what it is that you truly were meant to live. And so I appreciate [00:31:35] you joining us today. Hope you have an amazing week. This is George Wright III and The Daily Mastermind. We'll talk with you [00:31:40] soon. ​[00:31:45] [00:31:50] [00:31:55]

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About the host
George Wright III, host of The Daily Mastermind

George Wright III

George Wright III is an entrepreneur, investor, and the host of The Daily Mastermind. Over more than two decades he has founded and scaled several multimillion-dollar companies and built a renowned seminar business that put some of the world's biggest names and brands on stage. With 25+ years across marketing, sales, and executive leadership, he's made a career of turning bold ideas into results — and momentum into lasting growth.

Today his mission is singular: empower driven entrepreneurs everywhere to master their mindset, unlock their potential, and live their ultimate destiny. Through The Daily Mastermind, George shares the Prosperity Principles and strategies that help people create massive change — in their business and in their life.

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