Ep 161: Replacing Yourself with AI: Why Judgment, Not Knowledge, Is Your New Value Proposition
SUMMARY
I've been wanting to have this conversation for a while now, because it sits right at the center of something every creative business owner is wrestling with. AI. Is it coming for our jobs, or is it changing what our jobs actually are?
To dig into it, I sat down with Christian Brim, founder and owner of Core Group out of Oklahoma City. Christian's business is who I trust, and who we trust at Chief Creative Partners, with our own finances. Our books, our taxes, every money question we have about running a business. Core Group is built specifically to help creative businesses, so this felt like the right conversation with the right person.
What started as a chat about a chatbot Christian had been testing turned into a much bigger conversation about replacing yourself, why the age of the knowledge worker might be ending, and why experience and judgment, not raw knowledge, might be the new unique value prop for every creative business owner.
The Sandbox Isn't the Strategy
Christian had been testing a tool called Delphi, which builds an AI avatar trained on your own content: podcasts, Substack, whatever you've got out there. He wasn't trying to solve a problem with it. He was exploring.
"That's a great visionary term, by the way," I told him. It's exactly what all of us do. Somebody plays in the sandbox, and the ops person in the room goes, wait, stop, what are we actually trying to accomplish here.
That tension is worth sitting with. AI has opened up an enormous number of possibilities. The real question isn't whether you can do something with it. It's whether you should. As Christian put it, it's real easy to get enamored by what a new tool can do without asking if there's a purpose behind it.
Technology Doesn't Eliminate Jobs. It Moves the Value.
Christian shared a line from category design expert Christopher Lockhead that reframed the whole conversation for me: technology doesn't eliminate jobs, it changes where the value is created.
That's the shift. Knowledge used to be scarce. Now it's ubiquitous and free. Anybody can look up anything. But knowing something and knowing what to do with it are two different skills entirely.
Christian compared it to watching golf videos versus actually playing golf. You can watch a hundred videos and think, I can do that, that's easy. Then you get on the course and hook the ball so hard it hits the cart your buddy is riding in. There's no substitute for the experience, because experience is what gives you the context and the judgment to know if something even makes sense.
Judgment Is the New Job Description
This is where the conversation got real for creative businesses specifically. Christian pointed out that most creativity lives inside marketing somehow, and that shift is happening top down. Business owners are saying, I don't need to hire a designer, I can just use AI to build the thumbnails.
But here's the question nobody's asking: should you even be designing thumbnails in the first place? What does a good thumbnail actually look like?
If good enough is good enough for your business, that might be fine. But most creative business owners didn't get into this work to produce average. That's exactly why the unique value proposition is shifting. It's not what you do for a client anymore. It's the perspective, experience, and judgment you bring to the table.
Christian used a medical example that stuck with me. AI diagnostic tools are coming, and they might eventually be as good as or better than a physician at reading blood work and radiology reports. But nobody is going to read an AI diagnosis of cancer and schedule chemotherapy without a human being involved. That's the judgment part. The tools work best in the hands of someone experienced enough to know when to trust the recommendation and when to push back on it.
Play Is Part of the Strategy
One of my favorite parts of this conversation was about permission to play. I'd just finished Austin Kleon's new book, which points out that some of the most successful writers we'd recognize by name spend more time reading than writing. We live in a culture that tells us to constantly produce, but if we're not putting enough in, what we put out ends up shallow.
Christian's team explores AI the same way. Pick a problem, see what the tool can do with it, not necessarily to solve it, just to understand its capacity. That's play, not production. And play, without commercial intent attached to it, unlocks a different part of your brain than grinding toward a deliverable does.
We genuinely don't know where AI is headed. Nobody predicted how the steam engine would reshape society when it was first invented. If we stay locked into solving today's problems with today's tools, we miss the insight that only comes from sitting back and asking what if.
Protect What You Can't Get Back
This conversation also had a practical, sobering edge. Core Group is still finalizing their internal AI strategy, but part of it is defining what they're comfortable letting AI touch and what stays firmly off limits, especially client data.
Christian shared a stat that stopped me: the average time it used to take bad actors to exploit a software vulnerability was around seven hundred days. That number is now down to twenty-six. AI isn't just changing how we create. It's changing how fast our data can be exploited if we're not paying attention.
Where This Leaves Us
Ten years out is too far to predict with any confidence, and Christian said as much. But the next couple of years are clearer. The old model of "I have this skill, this is what I do" is going away. That doesn't mean videographers or designers disappear. It means the resources you bring to a client relationship need to be more varied than a single skill set.
Entrepreneurs are problem solvers. The problems are just changing. And that's not a threat. That's opportunity.
If you want to know more about what Core Group does for creative businesses, head to coregroupus.com. And if you're wrestling with where your own value is shifting as a creative business owner, grab our free resources at dustinpead.com/free to start building clarity around what only you can do.
You create. We operate.
KEY TAKEAWAYS
⚡️ Knowledge is no longer the differentiator. Judgment is. When anyone can access the same information, your value shifts to what you do with it, how you apply it, and whether you know when the AI-generated answer is actually wrong.
⚡️ Wonder is a creative engine, not a distraction. Christian's rule for brainstorming: no bad ideas, and start everything with "what if." That phrase depressurizes the room and opens up thinking that pure execution mode never will.
⚡️ An AI strategy isn't optional anymore. Define what you'll let it do, what you won't, and how you're protecting client and business data along the way.
NOTABLE QUOTES
💬 "It's opened up the possibilities of what you could do. The question is, should you be doing them."
💬 "All AI does, all it ever can do, is drive to the mean. It's never going to produce anything exceptional."
EPISODE RESOURCES
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TRANSCRIPT
So I don't know. Maybe we're moving into the age of the judgment worker, the experience worker. Those words are more applicable because that's where the value is, because the knowledge is ubiquitous. It's free. So what do you do with it?
Hey, everybody. Welcome back to the Chief Creative Podcast, the show that equips creative businesses to unleash their best work. I'm Dustin Pead, your host, founder of Chief Creative Partners, where you get to create because we operate.
Today's conversation is one I've been wanting to have for a while now, because it sits right at the center of something every creative business owner is wrestling with right now. And of course, that topic is AI, and whether it's coming for our jobs or changing what our jobs actually are.
My guest today is Christian Brim. He's the founder and owner of Core Group out of Oklahoma City. Christian and I have known each other for a while now, and he's the guy at Core Group who I trust, and who we trust at Chief Creative Partners, with our own finances. Our books, our taxes, any money questions we have about operating a business. They're designed specifically to help creative businesses.
In our conversation, we get into a chatbot Christian's been testing out, and that turns into a much bigger conversation about Andy Stanley's idea of replacing yourself, and why the age of the knowledge worker might be ending, and why experience and judgment, not necessarily knowledge, might be the new unique value proposition for every creative business owner listening right now.
So if you've ever wondered whether you should be playing more in the AI sandbox, or whether your skill set is about to get eliminated, stick around. This one's a good one.
Christian Brim, thanks so much for joining me today on the Chief Creative Podcast. We're going to have a conversation around AI. You and I were chatting recently about a chatbot you'd started implementing and testing with your company, Core Group. Tell me a little bit about why you decided to do that. What problem were you trying to solve as we enter this conversation about AI and replacing ourselves?
I wasn't really trying to solve a problem. I was exploring.
That's a great visionary term, by the way. All the visionaries are like that. All the guys like me are trying to make stuff happen, and we're like, okay, here's the eight things we need to do, and you're like, no, I'm just playing in the sandbox.
That was exactly Chelsea's reaction. She was like, wait a minute, stop.
I'd been doing some work with category design, Christopher Lockhead, as we were discussing in the green room. As part of their subscription, they have these bots. The Christopher Lockhead bot, and then another guy, Mike Lee, I think his name is. You can go in and have a conversation with it about category design. Here's what I'm thinking, here's what I've come up with, tell me where I'm right or wrong. I was looking at the tool they used, a tool called Delphi. Essentially what it does is you can self-train it, or it can pull from various sources, including podcasts and Substack. Whatever you've got out there, it'll pull in and train on, and create this avatar for you. I figured I'd give it a try, see what's happening. It's been interesting. I haven't gotten enough feedback from it to really know if it's worth continuing. It's not expensive, but to answer your question, I wasn't really trying to solve a problem. I was just exploring what the technology could do.
Is it worth adding, you said. And my mind immediately goes to, in this world of AI that's opened up so many possibilities, I can't stand it when creatives say AI is killing creativity. I think it's enhancing it. It just gives you a different way of enhancing it. But is it worth adding to your tech stack, worth adding to your methodology, when in a world of distraction, simplicity is the answer? You almost have to look at software as a hiring decision. Hey, I'm going to hire this software to come in and do some things. So where did you ultimately land? This isn't an ad for or against Delphi, but where did you land? You said you're still testing it.
I'm still testing it. There's a free layer. I did the paid layer, month to month. I probably won't continue it. I'll probably downgrade. Delphi is primarily designed for public-facing personas. If you're an expert in something, a speaker, or on different media, it's there to enhance that presence. But before I go on, I think exactly what you said is right. It's opened up the possibilities of what you could do. The question is, should you be doing them? It's real easy for me to get enamored by, oh, look what this can do, look at these new toys.
Fun.
Really trying to say, well, is there a purpose behind it? Is there a problem you're trying to solve? And the answer in my case is no. But I do think, looking at it, I know you do a lot of AI in your SOPs, and what I think AI does a fantastic job of is categorizing data, and making the user interface more friendly so people can get the answer they actually need. I'm still trying to figure out why all the software companies still have help pages. Why am I looking at help articles? And how awful they are. You put it in the search bar, words you think it might key on, and you get ten articles and none of them answer your question. That's the application for AI. I think there's a ton of opportunity, both internally and externally, for that use case.
I think help pages now are less there for people to actually use in the traditional sense, and more there for AEO, answer engine optimization. So when someone Googles or ChatGPTs "how do I do XYZ," hopefully their website or their answer comes up, and people notice it was found on that website.
This whole conversation started, Christian, when we were talking about Andy Stanley, a pastor here in the Atlanta, Georgia area, who wrote a book a long time ago called The Seven Practices of Highly Effective Ministry. Me coming from the church world, there's a lot of overlap, for better or worse, from ministry to business and leadership and how to do things the right way. One of the seven practices is to replace yourself. I think that's a hot, very sensitive topic right now, because a lot of people are afraid AI is going to replace them. But I actually think it's good to try to replace about 80 percent of what you're doing day to day, so you can focus on the 20 percent only you can do. That's nothing new. That's old leadership, as old as John Maxwell. So how have you been using technology, AI or whatever, to start replacing yourself? That's kind of where we started this conversation with Delphi. Are there other ways you're doing that, to offload so you can level up, or do you see it as the opposite, where it's just coming and taking over and you can step out completely?
Christopher Lockhead had a quote I pulled and shared with the team. He said technology doesn't eliminate jobs, it changes where the value is created. I don't do a lot of routine things. What I've run into in my own implementation of AI personally is, oftentimes the juice hasn't been worth the squeeze to teach it what I need it to do, because it's easier for me to just do the thing, since I don't have a lot of routine tasks. However, I think the advent of agents this year has changed that paradigm, because someone else has already figured it out. I don't have to train it. Someone else has already figured out that agent, and I can download it for free and use it.
That's why, six weeks ago, I bought a mini Mac. I am now part of the cult, which was a strangely uncomfortable transition, going to Macintosh on a desktop. I figured it would work more natively with Claude agents and other AI than Windows.
How I use Claude Code is in helping me refine my thoughts. Usually what I do is give it a paradigm and say, okay, I want you to hold me to this paradigm as I'm thinking through these things and presenting ideas. Make sure I'm being consistent in achieving what I said I wanted to achieve, keeping me from wandering, or going down a rabbit hole that's wrong.
But here's what's wild. I built one Claude bot on Mike Damphousse. He's another category design guy. He wrote a book, I read it, and I took all the principles and created a bot. I'm not using the LLM, I'm using Claude Code. I wrote a bot with the principles of his book and said, this is what I'm trying to do, and I want you to push back where you see me veering off the paradigm.
What was wild was I had an hour-long conversation with Mike, uploaded the transcript to the bot, and it proceeded to tell me why Mike was wrong.
Hold on a second. He's the guy who wrote the book.
Right. Chelsea had been trying to use the LLM in a similar way, and I was sharing that experience with her. It's a powerful tool, but you really have to be careful. Thinking is even more important when using these things, because if you just accept what comes back, you're in trouble. You have to have judgment. You have to have context to know if what it's telling you even makes sense.
Or is applicable.
Exactly.
You mentioned perception, and now judgment. You and I have had conversations, on and off the mic, about unique value proposition, what problem you're trying to solve, your unique place. And the conversation now, in the landscape of all businesses, but certainly in creative businesses, is what is your unique value proposition going to be when someone can go on ChatGPT and create their own thumbnails? Why do they need a designer for that? I think the reason I use a company like Core Group, rather than some AI bot to balance my books and file my taxes, which I'm sure is coming, is because of your perspective, your judgment, and your experience. That's an interesting shift we're having to make, culturally, but even more specifically in our fields working with creative professionals. My unique value proposition is the perspective, experience, and judgment I bring. It's not necessarily what I do for you anymore. It's more about thought leadership. How have you seen that play out?
I'm not really trying to hype up Christopher Lockhead, but the guy is just brilliant. He wrote an article recently, or his AI did, about how the age of the knowledge worker is gone. That's been where we've been for the last sixty, seventy years. I don't remember who coined the phrase, it may have been Drucker. But it's been prevalent all of my adult life, this idea that we've moved from the industrial age to the age of the knowledge worker. The problem is that knowledge has been commoditized, democratized. Anybody can know anything now.
But it's the same thing as watching a bunch of golf videos and actually going out and playing golf. There's no substitute for the experience, because the experience gives you the context and judgment to say, does this even make sense? We all watch that and think, I can do that, that's easy, look at that. And then you get out there and swing, and the ball dribbles ten yards to the left. I hooked it so hard once it hit the cart my partner was in.
I've done that many times.
Yeah, that was an embarrassing moment. So I don't know, maybe we're moving into the age of the judgment worker, the experience worker. Those words are more applicable now, because that's where the value is, because the knowledge is ubiquitous. It's free. So what do you do with it?
And also the application, right? We talk all the time about giving your stuff away, giving away your frameworks, your methodologies, giving all that away. And someone young in business says, well, I can't give that away, that's the secret sauce, if I give it away people will just do it on their own. And I say, no one's doing it on their own. They're training AI agents to maybe do it for them, but no one's doing it on their own. The reason they come to people like Core Group or Chief Creative Partners is because, yes, they could do all the things we're doing, since the knowledge is out there. They can listen to Christian Brim's podcast, they can listen to mine, they can read books, they can figure it out. They probably can. But they don't have the time for it. Time is the commodity we can't get back. It's the one thing that's burning constantly. What we do with our time every single day matters, I think, now more than ever.
Yes. I think the shift for a lot of creatives that's really making them uncomfortable is, I learned a skill, I'm a designer, a videographer, a copywriter, whatever, and then all of a sudden people aren't buying that, or they're buying it differently, or not paying as much.
And that will happen to accountants. It'll happen to radiologists. In some form or fashion, this technology will impact everybody, because what it's doing is making predictions cheaper. But here's the thing. Do you have the judgment or context? Do you understand the limitations of the machine? Do you know where it has a blind spot and goes wrong, to actually act on that prediction? It makes much more sense for those tools to be in the hands of the experienced person, to leverage their time and say, yeah, that's a solid recommendation, that's a solid choice.
I've been using this medical example for the last two years. WebMD is eventually going to have some diagnostic AI tool, or somebody like them, where you upload your blood results and radiology reports and say, give me a diagnosis. And it will be at least as good, if not better, than a physician's diagnosis. However, are you going to say, well, I've got cancer, I need to go schedule chemotherapy? No, you're not going to do that without involving a human. That's the judgment part.
What I see out there specifically with creatives is this paradigm. Most creativity is involved in marketing somehow, and in the business world, it's shifting from the top down. People say, well, I don't need to hire a designer, I can use AI to do the design, do the thumbnails, whatever. But here's the thing they don't know. Should they even be designing thumbnails in the first place? What does a good thumbnail look like? Because all AI does, all it ever can do, is drive to the mean. It's only going to give you the average. It's never going to produce anything good. Nothing exceptional.
Nothing that stands out.
And if good enough is good enough for you, then maybe that's good enough.
Oh man, that's good. We've had this conversation too, before we started recording, about an AI strategy. When we're having a conversation around AI replacing us, whether on purpose, accidental, fearful, hopeful, whatever the psychology behind it, I think it's important, and you do too at Core Group, to have your own stance on who you're going to be when it comes to AI, because it's such a topic. Originality is such a thing. Great versus good is such a thing. Good service is such a thing. Talk to me about the evolution of the AI strategy you guys have been working through, and what conclusions you're coming to about its role at Core Group.
We haven't finished our AI strategy. I think that's part of the rock we're working on that we'll complete by next month, but we're pretty far along, doing exactly what you said. Defining how we're going to use AI as an organization, what we're willing to let it do versus what we're not comfortable with as far as its capacities. Structural things, like integrity of client data. Not exposing client data to the world. That's one of the other things people don't really talk about, that bad actors are using AI in nefarious ways to steal things, in ways we never contemplated.
I was reading an article about the average vulnerability window for software. It used to take bad actors seven hundred days, almost two years, to figure out how to exploit a glitch in security. That time is now down to twenty-six days. As far as your intellectual property, what you keep internally, and for us, our client data, that's a huge thing I don't hear a lot of people talking about, how to protect yourself.
What's interesting is the younger people in our organization are the most resistant to it.
Do you think it's because they believe it's coming for them?
I think there's an element of that. I think there's also a strong pushback related to the environmental impact and factors like that. But what we've asked the team to do is just explore the possibilities. Pick a problem, see if it can fix it. Not necessarily to solve the problem, it might not be able to, but just see what the capacity is. Kind of like what I did with Delphi. Just play around with it, get in the sandbox and play.
That's good. I wanted to make a point earlier, when we were talking about getting in the sandbox and playing around, that I just finished reading Austin Kleon's new book, Keep Going... actually it's called Don't Call It Art. Basically, what did he learn about creativity from his kids. He talks about how some of the most successful authors we'd recognize by name spend more of their time reading than writing. In our culture today we think we have to constantly produce or we'll get left behind. But what we're producing is so shallow, because we're not putting enough in. He talks about having work that looks like play. And you were talking about playing around in the sandbox with it, and your ops person going, okay great, here's the eight things we need to do, and you're like, I'm just playing, and your ops person is like, well when you play, please don't tell me, because I think it's something we're running on.
But I think, getting back to creativity and AI, that's where most of my time on AI these days looks like play. It looks like me trying to go, I wonder. And that wonder, that type of word, that type of stance, is the engine of creativity. When I lead brainstorm sessions I have two rules. Number one, there's no bad ideas. Number two, start everything with "what if," because it immediately unlocks and depressurizes the situation. What if monkeys jumped off the tree and swung around our house? It throws the whole sense of reality right out the window. I think it's interesting to think about AI and creativity, and consider there might be some play there, and that's okay, because we need to have that wonder. We need those what-ifs in order to actually produce good, human, genuine, better-than-standard creativity.
I would one hundred percent agree with that statement, but I'd take it even further. Maybe you're implying this and just didn't say it, but there's no intent behind it, specifically no commercial intent. If you think about the idea of play, and I know I don't play enough, play is like, you're doing it for the fun of it. When you're at recess playing tag, it wasn't to accomplish something. So often as entrepreneurs we get locked in. That was where we started this conversation. What are we trying to accomplish with this, should you even be doing this. Being able to just do something for the fun of it is wildly creative and helpful, because you unlock a different part of your brain.
You mentioned writing. I've resisted journaling for decades. I've started and stopped it. As I've been doing it, it's unlocked something in physically writing. There was a Norwegian study I read about right after I started again, where they gave students the exact same words to write or type, and tracked the neurological effect. It's not even close. Physically writing produces so much more brain activity in different parts of the brain. I don't know why, maybe it's because it's slower, maybe it involves different parts of you, I don't know. But I absolutely experienced it, because as I was writing through things I was gaining more insight.
Yes, I agree with you one hundred percent. We need more wonder, because, and this is what I'll conclude with, we have zero idea where this is going. I don't care who you are, you don't know. If you look back at the Industrial Revolution, when they invented the steam engine, they could not foresee how that was going to transform not just the manufacturing process but society itself. There's no way to predict it. If we're locked in trying to solve problems, we're not going to have any insight at all. But if we sit back and wonder and ask what if, that's where we need to be right now.
Oh, that's so good. To conclude the conversation, the people who listen to this podcast, who we serve at Chief Creative, are creative business owners, future CEOs. We just said we don't know where this is going, but let's take AI out of the picture, not completely, but let's focus more on the creative business owner for a second. Ten years from now, where do you see a creative business owner fitting in their business? Is it any different than today?
I don't know about ten years, that seems like a very long time. I can't see that far. I can see what's happening right now and what the next couple of years look like. And it's no more, I have this skill, this is what I do. That business model goes away. It's not like AI is going to create all the videos out there. Are there going to be videographers? Absolutely. But the transition is to understanding exactly what problem you're solving, and where that value point, like Chris said, is shifting. I see that the resources you bring to bear, maybe not personally, but the resources, are going to be much more varied and different than they are right now. It's not going to be just, I do this.
That's what I see. You pointed out, I've been saying for a long time, knowing what you solve, entrepreneurs are problem solvers, and the problems are going to change. And they are changing. And that's just opportunity.
That's good. That's real good. Well, Christian, thanks so much for your time today. If people want to find out more about Core Group and what you guys do, go to coregroupus.com. Is that right?
That's correct. Coregroupus.com. Don't trust your money to a box as a business owner. Let Core Group handle it. I promise you'll be happy with it.
I'm a user of Core Group myself. They do great work. Great people, always looking forward, never get stuck behind. Christian, super grateful for your time today, and I hope to have you back real soon.
Well, I appreciate it, and thank you for the endorsement.