There's a certain kind of client who will never want what you're offering, no matter how good your pitch is. The episode opens with a story about a roadside crab shack in Maryland with 178 reviews and a 4.8-star rating, and why Casey walked away from it as a hard no. What that moment revealed about positioning as a fractional CMO is the whole argument of the episode..
He also draws a sharp line around AI: why the CMOs leaning into implementation tools and agentic builds are setting themselves up for a painful conversation at the three-month mark, and what clients actually want when they say they want "AI stuff." The episode makes the case for staying in the strategist seat, even when the temptation to tinker is real and the tools make it easy. .
There’s a certain kind of client who will never want what you’re offering, no matter how good your pitch is. The episode opens with a story about a roadside crab shack in Maryland with 178 reviews and a 4.8-star rating, and why Casey walked away from it as a hard no. What that moment revealed about positioning as a fractional CMO is the whole argument of the episode.
He also draws a sharp line around AI: why the CMOs leaning into implementation tools and agentic builds are setting themselves up for a painful conversation at the three-month mark, and what clients actually want when they say they want “AI stuff.” The episode makes the case for staying in the strategist seat, even when the temptation to tinker is real and the tools make it easy.
Key Topics Covered:
In this episode, I’m gonna talk to you about selling things that people actually want an experience that I had of someone selling something that I didn’t want, and how to position yourself so that companies come after you instead of coming after a broader category. That’s gonna make winning the business a whole lot easier.
 Hey, it’s Casey. Welcome back. All right so big idea. I live in Philadelphia, you probably know that by now, and Raphael, who’s been on my team for years, Raph joined… He was, like, my first hire. My first good hire. I hired an overseas VA years ago, and that was just a mess, and that was more about me than about them.
But Raph, I hired him when I was living in the RV, when we were living in Washington PA, just outside of Pittsburgh. Hired Raph as my assistant, and Raph has just grown to be this great coach inside of the Accelerator. He’s done a ton of coaching training, and he’s just is a really connected guy and helps people with their internal stuff.
There’s the tactic, there’s, like, how to sell, all that stuff, but then there’s the blockers, the interpersonal stuff, like the feelings of not enough or concerns that you have about being judged by someone else, or maybe the deeper reason that you’re not actually doing the work.
Raph is just incredible at helping you uncover that, and he’s been on that path for years. Then I had the great opportunity to meet Raph’s daughter. So Raph lived in Chicago, and then he moved to Philly, and he was here for a few years, and then he headed out west. So he’s now up in Oregon and, sorry, Washington. They’re the same state to me. And while while he’s been out there, he had a baby. So Raph and his partner and their daughter were in town. They were in Washington, DC. So I decided to take my wife and kids, and we were gonna go see him, and we ended up going to a place called Kent Island.
If you know where that is, it’s just east of Annapolis, so a middle waypoint for both of us. And we spent the day at the beach and we had a great time After we left, I thought, I want my kids to have a real Maryland crab experience. And I look on Google Maps on the track back, and I see this place called Cranky Crab.
And, sounds good to me. I don’t know anything about crab, but I know my kids should have crab. And we get there, and it’s just a shed. It’s a man in kind of a shed. It reminds me of something that I would see in Biloxi or I don’t know St. Charles, Louisiana. It was, like, a couple boil pots and a tin roof and like a, a refrigerated cabinet with glass on it that you might see at a bakery.
But it was all outside. It was, like, inside-outside. Very Southern feeling for being so Northern in Maryland. And I got out thinking, “Okay, cool. I’m gonna just grab maybe a couple crab cakes and maybe some fries and we’ll be on the road.” I got there, and the guy was really nice and welcoming. I was one of the two cars there.
And I was like, “Hey, I’ve never been here before. I don’t really know the game. What are you selling? How does this all work?” And he goes we have crab and then we have shrimp.” And he told me the type of crab and the type of shrimp. And I was like, “Cool. How do you prepare it? Do you boil it?” And he’s like, “No, we steam it.
We steam everything. And, here’s the seasoning that we use.” And he goes over to his metal bowl and he pinches it and to bring it over to me. I don’t know what to do what with. To put it on my tongue or something. I said, “No, thank you.” And I went back to the car and I told, my wife and the kids kinda what was being offered.
And it’s not what we wanted. To us it was a no. To us it was, like, an absolute no. Almost who even would want that, right? It was such a emotional kind of “Yuck, that doesn’t sound good at all. I don’t want hot seafood on my lap in the car.” So we head out. And as we’re heading out, I see two younger women, probably I don’t know, high school age, getting into an SUV.
They… And they had just gotten their boil from him. And they were, like, really happy, and they had a big bag. A big brown shopping bag full of something heavy, presumably all of the crab and shrimp that they ordered. And for them, it probably was, like, exactly what they wanted. They were excited about it.
When I look at the reviews for Cranky Crab, it’s 178, 4.8 stars. And, people say stuff like “We were headed for a softball tournament and found this gem online. Hands down the best crab we ever had. Ordered the XL and we weren’t disappointed. All heavy, seasoned perfectly, and delicious. And the corn was super sweet.
We’ll definitely drive the hour and a half to get these again.” Someone wrote that three weeks ago. Their experience was the antithesis of my experience. I just didn’t want it. It wasn’t for me. And it reminded me on the drive back of you and your positioning as a fractional CMO. To some people, what you’re offering just doesn’t taste good.
It’s not what they want. It’s not the thing that they’re seeking. For other people, it’s exactly what they want. It’s the best thing, and they’re gonna come back for it again and again. And you need to know who you’re talking to. If that guy who owned the business, the Mr. Cranky Crab, if he thought that my experience was indicative of the general public’s experience, he would think that he had a failure of a business.
But obviously, plenty of people love what he’s got And I think there’s so much truth in how you apply that lesson to your work as a fractional CMO. You’re not the right person for small companies. You’re not the right person for companies that don’t have money. You’re not the right person for companies who maybe want to do marketing, but they’re not sure.
You’re just not the right person. Maybe they’re thinking that they want a course or they want to run through Donald Miller’s StoryBrand ChatGPT stuff. Maybe they want to hire a certified guide. Maybe they just need a website built and they’re gonna hire someone locally from the Chamber of Commerce list of businesses in the area.
Or maybe they’re at BNI, right? They’re just not for you. It’s just– That’s it. That’s the whole story. They’re just not for you. They never were for you. So you having any kind of emotional experience around not winning those as clients, I think is just y- you trying to make something that wouldn’t work, and it just won’t work.
That’s just the, the nature of things. So there are the companies that do need you, and those companies are probably bigger than you’re used to, probably. Some of you are coming from maybe Fortune 500 CMO seats, and that’s gonna be a different story. You probably want companies that are smaller than you.
But this, the common behavior that I see is that people go small. They go play small. They say, “I’m gonna go work with this smaller company because I think I can get a foot in the door. I think I can win them as a first client.” And inevitably what happens is that CMO becomes a implementation machine, especially with AI.
If you’re weak on your boundaries and you’re weak on your ability to push back, say no push the client to spend money on hiring people what you’re gonna find is that it is harder than ever to not do all the implementation work. Because you could just spin up a couple cloud code windows and you could send a flutter of agents out to do work.
And it feels fun. There’s a certain kind of feeling of it, and I wonder if someone’s gonna name this feeling. It’s like this brain-dead staring at a screen of black terminal windows prompting AI to do something for you and it just getting done, and it just feels like empty in some ways.
Like the work got done, but it didn’t have the effort with it, and without the effort, it just doesn’t feel the same. You don’t put your be- head on the pillow at night saying “Wow, that was a productive day.” In some ways it feels like, “Wow, I got a lot done, but it didn’t feel necessarily productive.” I don’t know.
It’s a weird space to be. You want to be the CMO who is orchestrating the outcomes, and maybe that means that you’re doing a little bit of implementation through AI. But the litmus for that is that it is simply faster for you to use an AI to do the implementation than it is for you to find and hire someone for it, and you’re willing to shoulder the burden of accountability for the actual thing and for maintenance.
A lot of us feel good about one-shotting things. I read a line someone wrote about Fable 5, and what we should do with Fable 5 is we should give Claude Fable 5 the bigger project that we otherwise didn’t think it was capable of, and just throw it at it and say, “Figure it out.” And then it can figure it out in one shot.
It can do it, a ground up build and be pretty accurate on the first go. So we feel cool doing that. We feel like, wow, Fable 5 just made this whole thing. It made this whole client dashboard. I– All I had to do was pull in three API keys, and it did the whole thing for me. But then what you don’t realize is that there is, at a minimum, maintenance, and I think that’s a massive massively overlooked component of AI development is the ongoing maintenance of it.
Who’s going to maintain the code base? You’re like, “Oh, I can do it. I just keep a Claude code window up.” Okay, cool. You can but now you’re gonna like fuss with the minor edits that someone wants, and you’re like, “Yeah, I can do that. Sure, it’s just one prompt.” But that one prompt slowly starts stealing away your context for the work that you should be doing, and you find yourself in a place where you’re context switching back and forth.
And instead of between two clients, it’s between the client where you’re providing marketing strategy and leadership, and the other part where you’re doing implementation. And it just becomes difficult to lead yourself. It’s not the place to be. So selling the thing that someone wants, you need to make sure that you’re selling your expertise, your truly, like your experience, your taste, your discernment.
We’ve talked about that. But beyond that, it’s about selling your ability to understand how to use AI appropriately. And thinking about AI for CMOs, I think of the myriad of opportunities where AI can be useful, and it’s exciting. You can think of everything from customer journey to sales to customer service to finance to whatever.
And as the CMO, you kinda wanna put your hands in all of that stuff because, yeah, it matters what happens with product, and it happens what matters with finance, and it happens obviously what matters in marketing and sales. You wanna be in, in the middle of all that stuff. And you see all these AI tools Have you seen all these platforms like Victor?
Have you seen all those great ads for Victor, right? Or Hermes, or Claude Bot or whatever. You see all these opportunities to create agents to do stuff, and then you see people selling agents, and I just want you to not drink from that. It’s not the place to be. Yes, agents are very cool. Yes, agents are transformative to marketing departments.
But first comes the marketing strategy, and then the leadership. And then leadership could say, “We should take some of this stuff that’s more programmatic, more repetitive, doesn’t need human discernment at this point,” whatever, and you can start building out AI agents for it. But we’re seeing a bit of a backlash in copywriting going back to humans because AI just took all the soul out of everything.
We’re gonna see that in ad creatives, I’m sure. Everyone has these ad creatives. Like I can go to a website and the tell for me right now, you know the tell in ChatGPT is the em dash. The tell for me on website builds from Claude, specifically Co- just Claude coding a website, is a pill-shaped I don’t even know what you’d call it, maybe like subhead above the headline that says something.
It’s always pill-shaped. The font is pretty much too small to really read, and that’s the one-shot approach that people have. It’s fine for people who aren’t discerning but it’s not It’s not– that’s not the thing that I want you to focus on. I don’t want you to focus on helping your client build a website with Claude Code.
I want you to help your client build a world-class website, and the platform is irrespective, right? It doesn’t matter what you choose. You choose the one that’s right for them. I’m still gonna choose probably a designer for the website if I can, a human designer. Maybe I’ll Claude Code a couple examples claude.ai/design and come up with a couple cool examples of what I would like, and then have a designer actually make it come to life.
But I always want that designer’s touch on it. So if your goal is to attract people to you, you have to be the kind of person who can talk about these things from a high level and not be the person who’s committed to a single platform. You’re not the Salesforce person, you’re not the HubSpot person, you’re not the “we have to transform the whole business with Claude Code.”
If you become that person you’re gonna be really attractive in the short term, and you’re gonna burn out because the client’s gonna see you as just a person who’s standing up technology and not the marketer, and then they see your high prices, and they decide that maybe they want a better technologist than you, and then the marketing problems don’t really get solved.
You have to stay focused on marketing problems and have the client want you. You can’t sell AI. AI is merely a tool in your pocket. It’s a great tool. It’s probably the most ex- exciting tool that, I don’t know we’ve been given in the last few years. But it doesn’t mean that then it needs to become your identity.
You don’t wanna be the guy at Thanksgiving or the woman at Thanksgiving who’s talking about Bitcoin again, right? You also don’t wanna be the person talking about AI transformation for every single client that you talk to. That’s not it. Most companies need more leads. Most companies need speed to lead salespeople dialing leads marketing dashboards that show the health of the lead converting through an email nurture sequence ads that get refreshed at a regular basis so that it attracts the right people at the right time.
That’s what they’re looking for time and time again, and they may say that they want AI stuff right now, and, maybe they do, and there’s some ways for it. But the way companies by and large use AI right now is to, write copy or they think it can hand over their entire business.
And I still think that you wanna have intermediate layers of humans or a CTO who can manage all of the maintenance of things, and then you lay out structure. So my encouragement here is to not become the one person who does it all. I want you to be the cranky crab guy who sells something that some people just don’t want, but other people, it’s the best thing that they’ve ever had.
And that’s gonna be marketing strategy. It’s gonna be the thing that allows you to sleep at night without laying in bed with a Claude Code window open falling asleep with your phone screen on, waking up in the morning and seeing Claude Code and answering the prompt that it stopped you at. You don’t wanna be that person for your clients, and it’s easy to be that person, especially if you’re a helper.
So stay focused on marketing strategy, marketing leadership. AI stuff is super fun, but you have to focus on the thing that the client actually needs, not just wants. And that’s how you’re gonna be able to defend your position. After three months, the client won’t have to come back to you and say, “So what’d you actually deliver for us?”
And you’re like, “Agentic solutions.” They’re like, “Okay, but where are the results? Where are the leads?” For some it’s cost, right? They want AI because it reduces cost. But for others, they want to tackle the opportunity that’s in front of them. So there’s like the financial cost and there’s the opportunity cost.
And if it takes you three months to spin up an AI thing because you’re completely capable and you can figure it out, But you do that at the cost of getting leads and helping grow the business three months later, and you just had a quarter of the year burned you building something, and was that really the right move?
Or should your AI approach have taken six months, but at the same time, concurrently, you built out a lead-generating campaign that actually drove qualified leads? I wager that you probably should focus on the thing that drives growth in the business, not the thing that’s sexy and exciting.
No client is gonna come to you after three months or six months and say, ” I’m so thrilled we all have all of this AI stuff, and despite us having no additional revenue I’m still excited about it.” They’re not gonna say that. They’re gonna say, “This was a failure. This was a failure of hiring an expert.
You came in and you played with AI stuff, and I’m frustrated with you because you haven’t driven the business forward.” That’s what’s gonna happen. Make your crab, steamed crab stuff and sell it to the people who want it, and that’s how you’re gonna be the person who solves the problem, and you’re gonna stand out from a crowd, in a crowd that’s gonna get more crowded, because more people are claiming to be fractional CMOs.
But they’re gonna claim to be fractional CMOs that have these AI solutions, or they’re gonna force-feed a client a multi-hundred or multi-thousand dollar a month AI platform that’s gonna, quote-unquote, “solve all their problems.” Don’t be that person. Be the person who comes in, who does it bespoke, who does it right.
I’ve got a a banjo that I’m gonna have built. Years ago, I don’t know how many years ago it was, four years ago, I paid a $500 deposit to get in line for a guy to custom build a banjo for me. And I don’t know, maybe in the next year or two, my name will be called and I get to pick all the stuff for my banjo and he’s gonna build it for me.
That’s awesome. I’m very excited about it. He could make banjos a whole lot faster with a CNC. Just rip them out. He could make a couple banjos a week instead of what he makes now, which is probably one a month. He would charge probably less money, but overall probably make more money.
But in doing so, he would remove all of the soul from all of his work. I don’t want a banjo that’s less expensive, that’s manufactured through a CNC, even if he designed the 3D CAD models. I just don’t want it. I want the one that he has a spoke shave, that he shaves down by hand. I want him to block plane it, right?
I want his wife to do the fretboard inlays of my design. Like, how cool is that? That’s the guy who’s gonna last forever. Everybody else who, mass manufacturers, they’re just gonna be out-competed by the Fenders and Gibsons and whatever in the guitar market. In the same way, if you become a commoditized CMO, I just, I don’t think the future’s long for you.
So become the person who solves the bigger problem and not the person who is only talking about AI as the solution. AI is merely a, a pr- a tool in our tool belt to help us get to what we want for our clients. We talk about this a lot inside the Accelerator. We talk a lot about how we position ourselves to prospects so they say to us, ” What do you think I should hire you for?
Great. What’s the cost? Great. Let’s go.” You wanna be in that position where they’re asking you those questions instead of you selling. If you want my help getting in that position for clients to want you instead of you having to push yourself on the clients, then head over to cmox.co/call and book in a call with my team.
It’s a short 15-minute call, and we’ll just see if you’ve got what it takes to be an in-demand fractional CMO and if we can help you. We’ll lay out what that would look like and we’ll go from there, okay? All right. Go to cmox.co/call and I’ll see you cranky crabs later.
We are excited to announce the Fractional CMO Community Facebook Group. This aims to be a place where Fractional CMOs or marketers considering becoming a Fractional CMO can connect and share ideas.
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