The Marketing Strategy AI Can't Build for You
Entrepreneur School (In the AI Era)September 22, 2026x
194
26:1418.01 MB

The Marketing Strategy AI Can't Build for You

AI doesn't fix a broken marketing strategy. It just breaks it faster.

Laura Kendrick and I have been having low-key debates about AI for two years inside a business group we're both in, so I finally just put her on the mic and asked her what hill she'd die on. Her answer was immediate. AI is a genuinely powerful tool with real limits, and it can expand your brand voice and your strategy but it can never build them.

What you'll learn:

  • The exact point where an AI-built brand book stops serving you, and what to do when you hit it
  • Why validating AI output is the whole job, and how to do it when you're the only expert in the room
  • The research AI physically cannot do for you, no matter how good your prompts get
  • How to decide whether a platform deserves you at all, including the uncomfortable Instagram question

CHAPTERS

02:02 The hill she'll die on about AI

03:10 Where the AI brand book falls apart

04:30 AI only knows the inner emotions wheel

05:56 Validating output when you're the expert

10:38 The research AI can't go get

13:44 The signals you need to stop and strategize

18:10 Great tactics with nothing connecting them

22:48 A strategy that starts with the founder

28:30 The $7.5 million Instagram story

37:30 Plan it like it's your own wedding

Laura Kendrick is an online marketing strategist and the founder of Cheeky Copy. After six years writing copy and building brand voice for online business owners, she now teaches established coaches, course creators, and service providers how to turn scattered marketing into a smarter, more connected strategy that actually leads to sales. Her core belief: you don't need more marketing, you need a better plan.

>CONNECT WITH LAURA<<

Website: https://www.cheekycopy.co

Instagram & Threads: https://www.instagram.com/cheekycopy

>>Grab Laura's resource

Laura made a private podcast called Welcome In, all about folding humanness, hospitality and real care into your marketing whether you're operating at scale or keeping it small.

https://cheekycopy.co/welcome-in

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[00:00:00] AI is really good at helping you have really amazing tactics, but the strategy is the problem where it's, okay, sure, everybody says I'm supposed to go do all this guest podcasting, right? But is guest podcasting actually converting for you?

[00:00:15] Welcome to the next evolution of the podcast, Entrepreneur School (In the AI Era) We are here to figure out how to integrate AI into the business you've worked so hard to build in a way that still feels like you. I'm your host, Kelly Sinclair, award-winning marketer turned AI platform co-founder.

[00:00:36] AI has fundamentally changed how I thought about work, systems, and what's actually possible. This show is about navigating that new reality together. It's going to be a wild ride, my friend, but I truly believe there's a way to leverage AI in a way that's intentional, human-centered, and aligned. It's an ongoing evolution, so let's explore, because AI may just be the unlock you need to achieve the life-first business you truly desire.

[00:01:07] Here's the uncomfortable thing about AI in your marketing. It makes a broken strategy broken faster. And my guest today is going to tell you exactly where yours is leaking. I'm so excited to introduce you to my good friend, Prerna Malik. She is an online marketing strategist and the founder of Cheeky Copy.

[00:01:29] And after six years of writing copy and building a brand voice for online business owners, she now teaches established coaches, course creators, and service providers how to turn all that scattered marketing into a smarter, more connected strategy that actually leads to sales. And her core belief is, if you don't need more marketing, you just need a better plan. And we're going to talk today about how AI comes into play with all of this. Welcome, Laura.

[00:01:58] Thank you, Kelly. I'm excited to be here. Okay, so you and I are part of a business group together, and we have had many side conversations and many, like, borderline debates about different things with AI as it has evolved over the last couple of years.

[00:02:16] So I want to ask you right off of the hop, like, what is the hill that you would die on right now on August 13th, 2026 about AI? Because, you know, things change so fast. We have to timestamp all these conversations. Oh, for sure. For sure. AI is a tool, and it is a really powerful, amazing tool, but it has serious limitations.

[00:02:37] And you cannot use it. Truly, you cannot use it to properly grab your brand voice or make your strategy. You can use it to expand those things. You can get it to use what you have created to make all of your content a little bit easier to produce.

[00:02:59] But those things are not things that it can do yet. As of August 13th, 2026, it doesn't have the capability to think as deeply with as much nuance as the human brain requires in order to make that marketing really, really land. Okay. Expand on this, please. Expand on this with examples of how you're seeing this play out and what people are trying to use AI for.

[00:03:28] Yeah. Okay. So let's start with the brand voice, because this is foundational to a lot of people's AI curriculum. And I don't want to totally sit here and say, oh, all the AI curriculum is absolute crap. No, no, no, no, no. Not at all. But a lot of them start with you have to build a brand book and you have to use AI to do that. Heard. If you don't have anything in place ever and you've never done any of this before, sure, it is an amazing first step.

[00:03:55] Rock on. Take it. It will take you from, you know, the AI like full on slop to a lot closer. And if that is your first step, it's going to feel great. But eventually you are going to get to a point where you're like, this isn't landing. And I can use an example of this where I actually went through one of those processes out of morbid curiosity and honestly thinking that like, oh, maybe as a copywriter, this could be like a surprise and delight for my clients.

[00:04:22] If I could build them a brand book on the side and like hand them all this copy and then hand them this robust brand book, like wouldn't this be so amazing? And I tested it on my own and I know a lot about my messaging and my brand voice. I've done the work. Like I've been trained heavily on this stuff. And I found the process so frustrating. It could not get there. Even with being told this is what I do, it just was left or like it would it would then like vacillate to the right and it just couldn't get it.

[00:04:52] It was it just could not get to that nuance when it comes to brand voice in particular. The brand voice is talking about emotional states with the brand and like what you want people to experience. And the problem with AI right now is that it if you are familiar with the emotions wheel, it can only understand the inner circle of the emotions wheel.

[00:05:13] And the human experience is so varied that we have this outer circle that takes these basic human emotions and it pulls them into such deep specificity where like a mad is not real. Like that's a blanket term, right? That I feel rage and anger. And, you know, it just goes into all these spaces and it doesn't understand that you have to name that. You have to be able to say my brand is not just joyful.

[00:05:40] My brand is very specifically pulling into this space and positivity. And once you give the AI that, oh, my gosh, yes, it can run with it, but it can't get there on its own. OK, so you're talking about so many things that I've made with AI. I'm like, OK, let's let's unpack this. I think there's a lot of points that you made there.

[00:06:05] One is like if you have never done an exercise like identifying your brand voice and brand strategy. Yeah, it's going to blow your socks off that you can get something that's going to read back to you something more than you probably could articulate yourself. However, you, Laura, are a brand marketing expert.

[00:06:25] So you see between the lines and that's I think that's just like a general statement that we need to make for people is validating the output of AI is like so critical. So, I mean, just a slight side tangent here is when you just ask AI for something generically, you will get an answer. And if you don't have the expertise to validate whether that answer is good or not, then you might just take it at right value.

[00:06:54] So what you're saying here and what I always say, too, on the show and with what we're calling expert backed AI is that there is a layer deeper for sure. So when it's trained, it can do a better job. And I want to like add the caveat to like, yes, I'm an expert in brand voice and messaging and marketing and all these things. And I understand these things deeply. But I also want to give to anybody listening to this. You're an expert in your own business.

[00:07:20] You understand like if you're going through this brand book exercise and it's telling you that this is my read on it and you're like kind of like that's what I would get close, but not quite. You know, like that's where it wasn't telling me that I was a truck driver from Montana. It was, you know, it was like, well, you're kind of in this vague space. Like, yeah, but no. Or they were getting close to my ideal client, but it's like you're just kind of a little off center and the outputs weren't great.

[00:07:50] They just weren't right. And that's the thing of, yes, I'm an expert in this, but all of us are experts in our own businesses. I can't like when I actually will actively when I used to, I should say, do a brand voice session with clients. It was about pulling things out of their brains. I wasn't dictating to them. It was about walking through this journey with them. So I want to like hand that to you that you're an expert in your own business and your own people and your own messaging. It's just sometimes hard to pull that stuff out.

[00:08:19] And if the AI is, if you take this first step, you do the brand book, you're feeling really good about it. And then eventually you get to a point where either it's not feeling so good or you have become more sophisticated in your business. And you're like, this just isn't nailing it on the head. That's the time when you go back through and look as a human being and say, okay, where is it missing the nuance? Where can I fill in the gaps as the human being who knows the other human beings, who is on the call?

[00:08:48] And I can hand it all this information that I'm getting from being on these calls with these people, interacting with these people and understanding my business. And then, oh my gosh, like then you're going to kick it back up again and it's going to up level again. And then you're just going to, oh, you're just riding the waves and the AI is starting to sing for you. Yes. And it's all about those, those tweaks and that awareness, right?

[00:09:15] I think we should all acknowledge that there's nothing about AI that we can set and forget at this point, including how we teach AI to do a good job for us. Which is essentially what you're talking about in terms of having that brand. I call it brand calibrator, trademarked. Love that. Seriously, I bought a trademark for it. I was like, this is important. We need to calibrate AI to our brands. These are the pieces that need to go in there. And that's more accurate. And the process for getting that.

[00:09:45] Yeah, yeah, yeah. And the process for getting that is different, like depending on the expert that you're working with or whatnot. I have background in brand strategy too. But, and it's exactly like you said, it's about extracting the things out of the person, right? So, I mean, this isn't really what we're here to talk about.

[00:10:03] But the whole concept of creating some kind of a reference file like this, a calibration, that just helps you to get a better output from AI as you're using it.

[00:10:16] But what I think you're saying, that's the nuance, and nuance is such a critical term here, is that as your business evolves and you become more clear about your ideal client and you learn more about them and you learn more about their voice and all of that, that's where AI is now kind of back up at that generic level and you need it to go deeper. Yeah. And those are the things that you can't, it can't do all on its own.

[00:10:42] Like, and of course, if you are starting out and you're going to do like voice of customer research or things like that, AI can't do that either because you actually need the specific words of your specific people. And that you can't get through AI. Like, if you're my ideal client, Kelly, I can't go tell Claude or ChatGPT or whomever to like, what is Kelly Sinclair thinking right now? And if it could give me an answer, that would be terrifying. Like, it's time to rethink humanity.

[00:11:11] It might know because I do tell it everything. Fair. But it's those things of we have to ask the people the questions. We have to listen. And yes, we can feed that information to our AI and get so much insight. Like, it can dig through. But also, there's a moment of double check it. Of course, it hallucinates. It's if you were, I would recommend if you're going to do things like that, do it right after the call so it's fresh on your brain.

[00:11:39] So, like, when you're pouring through the output that AI gave you about a transcript, you can sit there and go, oh, yeah, we did. Oh, yeah, that was so important versus like, wait, what? Like, we didn't talk about that. Where did you get that from without having to individually pour over, like, print it out and highlight it like we used to have to do back in the pre-AI days? But those things are really important to understand. You're getting it not from a generic. Like, because AI can go, of course, search the Internet.

[00:12:07] It can give you basic information. Sometimes that information is helpful, but you're not going to be able to dial in your marketing and your strategy to your specific people unless you're hearing from your specific people. Because context matters. Nuance matters. There's so many different pieces of this puzzle that you just can't get from the old Google search or the old, you know what I mean? Like, you never could get it from there. It was just a kind of additional layer on top.

[00:12:37] And now AI is able to do that in a much more robust way. But it's still not as good as having a couple of conversations or listening, like really listening to what's coming up when I'm talking to my people. What are people replying when I send out an email? What are they responding to? That is just gold. And AI can't do it. It can sort it. It can categorize it. It can record it. It can't get the information for you, though. Mm-hmm.

[00:13:07] Okay. I'm trying to decide whether we should talk about you. You decide. Here's your two options for the next question. Signal that you need to do this work or order in which this kind of has to happen, because there's clearly a step-by-step path to getting the right results.

[00:13:30] And we're just talking about not how to manipulate your AI to do this for you, but how to actually get that marketing strategy and your messaging locked in so that everything else becomes easy. Mm-hmm. Let's talk about the signal, because I think that's an interesting one that people aren't talking about. Okay. Yeah. Okay.

[00:13:52] So the signs that you need to do this kind of work and think about the strategy and spend that time there is – okay, I think we're living in a really interesting time where there's so much information that is at our fingertips. And, like, I remember the 90s when people were talking about we're in the information age. Like, we didn't have shit on what we have now. Like, it is just amazing, right?

[00:14:19] So we have all this information, and we have people who are innovative and creative as all get out. Like, we have stay-at-home moms who are changing the marketing space. Like, it is unreal, and it is really cool. But it can also get super overwhelming because you're sitting here trying to, like, okay, how do I get the algorithm on Instagram to do what I want it to do? But then also that's different than the algorithm on TikTok. So how do I make that work?

[00:14:44] And then I'm told I'm supposed to be podcasting over here or guest podcasting or, you know, showing up on this stage or doing blogs or SEO. And it's just like, oh, my God. Like, your head just wants to explode. And even if you're doing all these things and even if you're using AI to make it easier, because AI does make it easier to show up on all the places with a cohesive message.

[00:15:09] If you're feeling this sense of, like, oh, my God, or overwhelm or not wanting to show up in particular places or honestly sitting here volleying against the people who are saying to do one thing or the other and being lost in that, any of these things tells you that you really have to stop and do this work.

[00:15:32] That you need to think about really strategically about who your people are, where they're showing up. And, yes, they might be showing up on multiple platforms and there might be nuance to the types of people or the types of buyers or, like, what specifically you're selling on different platforms. And AI makes it so you can have sophisticated marketing strategy and talk different things on different platforms, which is amazing. And you can do it as a solopreneur or a really small team, which is rad.

[00:16:03] But AI can't do it for you, because if you walk in and tell AI, like, I need a marketing strategy that just blows up my platform, it's going to tell you some, like, crazy way. It'll be relatively generic and it'll be something that probably says show up on 50 different websites. And then you're just sitting there going, like, oh, my God, this is what I'm already doing and it's not working. Mm-hmm.

[00:16:28] I want to support what you're saying by, I mean, we are building a brand new platform. I am, like, at stage founder, beta clients, you know? And it's so tempting when you get doing fun things, playing with AI. You're like, ooh, and I can create a skill that will build my YouTube things and I'll put it here and I'll do that. And I'm doing all those things.

[00:16:56] Like, I have an addiction. I kept saying, like, when Fable 5 came out, I'm like, I went on the bender, still on the bender, still, like, last night at 1130 being like, oh, I got an idea. And, like, getting it to do, I'm like, can you please do this while I go to sleep? Try to sleep because I needed to plug it over there.

[00:17:17] But that to say is that I constantly find it challenging, and I'm sure everybody does, to pull back to, okay, who are the actual humans who are using Wave right now? Why are they using it? What are their, like, what can we learn from them?

[00:17:37] So how can I get that, like, voice of customer research, that market research out of the people who I already have so that I am using actual data and information to make decisions about how we move forward instead of just my gut, which I love. I love to trust my gut, all the things. Yeah, there's certain things where you should do that. It's, and that's the thing, like, I feel like we all, many of us, I should say, entrepreneurs, we do that stuff.

[00:18:07] Now, AI's just made it so much easier to dig in where we want to learn and add and all the fun stuff. And I'm all for it, and I'm with you. Like, I've done all those things as well. It's like I have to rein myself back in. But the catch is, too, as you're building these things, yes, AI can write you amazing show notes for your podcast that are, you know, follow the best practices and do the things and make it so you don't have to think very hard about it. And that's amazing. And you can get it out there.

[00:18:35] It can help you strategize these pieces. But then at some point, your AI becomes exactly what we were all doing before, where we were all sitting pre-AI, sitting there going, how do I show up on all these places really well? And AI's doing the same stuff, but it's not necessarily connecting it really well. So it can dig really deeply into how to harness YouTube. But also, if you talk to any, like, YouTube expert, they'll say, like, it has its limitations, right?

[00:19:04] And but then the question becomes, how are you actually connecting YouTube to potentially podcast to potentially trying to get found through AI and or SEO? How do you connect that to how you're actually converting? How do you connect that to the emails you're sending out if you're doing that? How do you connect it to your social media? And then at the end of the day, we're sitting here asking ourselves, well, should you be on any of these?

[00:19:36] And that's a question the AI really can't answer. Yes, if you ask it, it will give you an answer. But is it the right answer? Because it's like how AI works is not it's not asking you. It's not going through all the nuance of your life, your business, all of that stuff. It's going based on what it understands as broad marketing strategy. And that may or may not land for you because there are absolutely people who can get away with.

[00:20:04] And I'm like, there are going to be people who are going to take me to task for saying this. But there are people who can get away without having an email list and have a booming, amazing business. And there are people who can get away with having a booming business without social media and others who can't. And I can't tell you if that's you without a deep conversation. And you might know with that same deep conversation. But I can sure as heck tell you your AI does not know that. You have to tell your AI that.

[00:20:32] And you have to connect all the dots and find out what's worth it to you. Because AI is really good at helping you have really amazing tactics. But the strategy is the problem where it's, okay, sure, everybody says I'm supposed to go do all this guest podcasting, right? But is guest podcasting actually converting for you? And how do you make it convert? And how do you connect that into what is the path that when you do this that people come on?

[00:21:01] And why are you doing it? And what about the host when you're guest podcasting? Like, does that person really deeply matter to your business or not? Or is it just a, like, thank you for your audience? This is, like, I'm really just selling to your audience? Or is it, like, do they play a big role? And that, like, these are all questions that your AI can't answer for you.

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[00:22:37] I love this, Laura, because I have my background is all in marketing, and I was working with people on marketing and visibility, and I totally agree that the disconnect is that most people don't understand the difference between tactics and strategy.

[00:23:06] They say, I need an Instagram strategy where Instagram is just a tactic, like on its own. And so like all of those things that you listed off there, and I'm sure you would agree with the statement of everything works and everything doesn't work. The thing that makes it work is how it's applied to your specific business and how you actually execute on that. So speak more to the strategic side.

[00:23:34] Like let's say, okay, we've talked about AI enough. Like we don't need to like do that anymore. Let's talk about marketing strategy and how to create a good marketing strategy and what are the pieces that are needed. Obviously, a great human marketing strategist would be a great piece. I mean, I'd always recommend. Yeah. But besides that, like speak to that.

[00:23:58] So a great marketing strategy for, okay, for many of the people who are listening to this, where a lot of us are solopreneurs or have really small teams. So it's really starting with one person. So, and I'm speaking to that right now. And of course, you can expand it out to be bigger companies, of course. But speaking to that specific crowd, a great marketing strategy starts with you. It starts with the founder or very specifically what has intentionally been like,

[00:24:26] what part of the founder has been bled into the business and now is the brand. So it starts with you. It starts with your capacity, how you actually want to show up, where you want to show up. Because those are elements that matter. Honestly, it doesn't matter if your entire community is on Instagram. If Instagram makes you want to like throw your head through the like plate glass window every morning when you get up or like you have real ethical issues with social media or whatever,

[00:24:56] like whatever is coming up for you, that's a problem that needs to be addressed. And then I would say you shouldn't be on there. So it starts there. It starts with how the business wants to show up, where they want to show up. But then it also has to fold into where are the humans? Are your people actually like and not only the humans, but where are the humans that are going to buy from you? Because this is a problem with social media right now, where there's a lot of people who are being told you need to be on this

[00:25:26] particular platform or that particular platform. Like two years ago, the platform du jour was Substack. OK, great. But are people who are actually going to buy from you on Substack? And if the answer is yes, wonderful. Run full on like run. Figure it out. Go for it. If they're not. Why are you there?

[00:25:48] If you're on Instagram and there are you have 10,000 subscribers, not subscribers, followers on Instagram. But none of them buy for you from you. OK, I want to ask like a couple of questions. Is your purpose for being on Instagram to actually get buyers? Because if that's the case, then you're on the wrong platform, because if they're not buying from you, that's