Episode 48

Reconnecting in AI Marketing

Published on: 14th July, 2025

In this episode of The Backstory on Marketing and AI, we explore how marketing can reconnect with buyers in an era dominated by automation and AI. We unpack the challenges of disconnected marketing and offer solutions rooted in real human connection.

You'll learn:

·      How to avoid shallow automation strategies

·      The power of podcasting and community in B2B

·      Why trust-building beats targeting

·      How AI enabled market research can support—but not replace—human insight

·      The balance between tech and empathy in marketing

Whether you're in B2B, marketing automation, or customer experience, this episode will change how you think about connection and conversion.

Click here to view the video: https://www.youtube.com/watch?v=Xbz5mJ5VWzM

Transcript
Guy: [:

Uh, today I'm interviewing Casey Cheshire. He is, uh, with Ringmaster Conversational Marketing. And, uh, so let me tell you a little bit more about Casey. He's a seasoned marketer with over two decades of experience and the author of Marketing Automation Unleashed as the founder and CEO of Ringmaster Conversational Marketing, which is a B2B podcasting agency.

Build authentic connections. [:

Casey: Well, you see, my, my parents are actually ai, so, um, it was about, uh, 40 something years ago. Um, Chachi, pt, grok, you know, opposites attract, I tell you. And, um, you know, and after, uh, you know, marriage and, uh, puppy. Here I came.

Guy: Yeah. So is that how that works? I, uh, that's how that works. I'll have to try that.

Yeah. So how do you, what kind of prompted you put in there after that?

always involved some kind of [:

I remember. Back in the day when they were trying to take me deeper and deeper into computer science, and they wanted, at some point I'm programming gates to open and close on a processor, and I'm like, where are the humans at? Where are they at? And they weren't there. They weren't, certainly weren't there in the processor.

So, um, I, I found other places and marketing was really a, a home for me. I think a lot of people listening to this show can relate to that. But marketing is that beautiful intersection for me of creativity and analytics.

Guy: Yeah, absolutely. And, uh, well I'm on the analytics side and, uh, but certainly it, you know, it's really the, uh, the creative guys that come up with these incredible ideas that earn the big bucks.

able to, uh, replicate that. [:

Casey: Yeah. All the conversations around ai, you know, the, the thing that I, I like to just really take a stab at is it's that human connection that will.

Center everything, and we were chatting just a second ago about what's really gonna be the hook and human connection and human conversation will be the thing that will feed and take AI to the next level. Right? It, there's so much common knowledge, but you need that, that two, you know, two wizards talking like this and, and talking about a concept and original ideas and ideation happening.

You take the transcript for this conversation and now you really have something.

Guy: Yeah, how true. How true. And, um, otherwise, you know, you think about, uh, ai, it's really just the average of everything. It's kind of the most likely, the most probable whatever. So at some point, all you're gonna do is be getting the averages of the averages.

is it that, uh, your company [:

Casey: Create podcasts and community in order to connect businesses with their buyers, right? So the whole idea is that we got disconnected somehow. We put all the tech in between us and our buyers, and we don't even know what's going on anymore.

And we hallucinate just as much as AI does, making up what we think our buyers need, what we think their pain points are. And you know what? Skip all the craziness. Just go out and have a conversation with someone. Podcast is a great way to do that. Community round tables is another great way to do that and actually find out the truth.

What do they actually need? What can you solve? So that's what, that's what ringmaster does. We solve that problem for companies.

Guy: Yeah. Wow. Um, that is, uh, so critical too because, uh, you know, so many times, and I mean marketers generally are, uh, are usually trying to do a, you know, a good job at, uh, at being connected to their customers.

erstand what your, what your [:

Casey: You know, there's this game where I'm, and for those listening, I'm like waving my hands in the air. Hello. I'm trying to get your attention right. The whole get your attention game. And, and it's not, it's not a, in a good way, it's not like, Hey, stop the roads out ahead. Right? This is a, you're going about your day and I'm trying to interrupt you from whatever.

Focus you might have found for the moment, let me interrupt your focus and take you over here. And, um, it's a, it's very much a beginning the relationship with a take right? Is, is the game we, we start to play in the marketing side just by trying to interrupt their day, get their attention so we could do the whole get your attention thing.

ontent or whatnot to try to. [:

Maybe it's gotten so far to the point where get on the call with me and I'll buy you something from Patagonia. And I'm like, oh, okay, well you got me, but I'm gonna check my email while I'm talking to you. Right? So all these silly games to try to get someone's attention, to get on a phone call to listen to a thing.

The problem is it's so one sided, it's so take, take, take that When you get on those calls, they're not, they understand that and they're just taking, they're using that time. Right. So I, I wanna skip all that, skip all the games and just go invite someone to be on a podcast. And what's cool about it is it starts a relationship with a gift.

nterview you learn from you, [:

And then also let me, let me give you the gift of the platform and I'm gonna tell all of my audience all about you and, and they can learn from you as well. Like what a cool gift. What a great way to start a business relationship. So I'm trying to flip the script on marketing, screw all the other things, all those other games you play.

Stop giving out Felice blankets. Stop doing all the tricks. The Patagonia hat was nice, but I don't even remember the sales call, right? Skip all that. Give some time and attention. Do a podcast.

Guy: Well, I, uh, I like podcasts. I do a lot of podcasts, but I think in the winter I'd rather have the Pataga, Patagonia sweater or something like that.

bucks or a gift [:

You know, the podcast is, uh, a lot more interesting. Because, you know, you're kind of, um, you're kind of playing to their ego, uh, you know, because you're asking them questions about you. It's not, you know, not necessarily Yeah. You know, me telling you something, it's me asking. And, uh, and that playing to the ego is, uh, is definitely a, you know, a great way to build a relationship and have a great conversation.

So I like that. That's, uh, that makes a lot of sense.

Casey: Yeah. What do you selling? I'm buying. All right,

Guy: I like you. Right.

Casey: So it's the idea of like, you know, the whole Zig Ziglar quote, if people like you, they'll listen to you, and if they trust you, they'll buy from you. A podcast kind of skips to the trust part where we, oh, we had a, we created some art together.

ot the trust. It's a perfect [:

Guy: Yeah, absolutely. And, um, and that, and it's just that, that free and open discussion to, to what you said is that, you know, generating a friendship, building trust, and then you can start to, you know, see if there's any kind of a, a match and maybe there isn't. So, you know, and, and it's so funny too, is that sales, uh, especially in B2B, uh, is so emotion driven.

I mean, it's certainly in consumer, but it's also emotion driven. Yes. I wanted, you know. I need this product, but why should I buy it from you? Why should I risk my job and my reputation on buying something from you? Let me, uh, let me make sure that I, you know, I trust you first before I, you know, I take that, that big leap and recommend this for, for use in my business.

, you know what I, I spent a [:

And what it is, and a symptom of it is where your best laid campaigns start doing a little bit worse each time. Mm. And not, not your experimental ones, but your good ones, your tried and true campaigns. You're like, huh, why are they not doing as well? Why is my organic not doing as well? Why are these things not doing as well?

Um, and those are the symptoms. The cause is you are not connected to your buyer anymore. And, and I actually came up with this, this quiz, and I, I am not preaching, you know, like. I am the, have never done this. Like I, I failed this quiz. And here, here's the quiz. You, you, you go, okay. Can you name seven of your customers by company name?

Right? And you think, oh, [:

Sometimes it's no, but usually there's a, a delta. There's a difference between your first answer and the second answer, and that tends to. Illustrate your disconnected marketing. You're probably disconnected, right? If you can't name seven by first and last name means you probably haven't chatted with them in a long time.

And it's probably time to make a phone call.

Guy: Yeah, how true. How true? How true. So, uh, so you talk a little bit about disconnected marketing. Tell us, uh, what that is and how that's gonna kill my business.

Casey: You know, disconnected marketing is gonna kill your business because all of your investments in marketing and sales are missing the mark.

target. Right. I think back [:

You shot at the other kid's target. That other kid has a bunch of points. Now you have no points because you were shooting the wrong target. Yeah, you hit the target, but the wrong one. And that's what ends up happening when you have disconnected marketing because you, you might, you might spend lots of money and have some great PPC campaigns or you might have some great, you might go buy a list and blast them.

But it's, it's falling on deaf ears because those are the wrong people and you're solving the wrong problem. And so for me, getting back to being connected with the customers is actually asking them what keeps them up at night? What are the challenges they're facing? What does a day in the life look like?

ied doing SEO strategies from:

Guy: mm-hmm.

Casey: Today, [:

Right. You'll just, you'll get shadow banned off the whole site. You can't use old strategies. In a modern situation, right? You gotta stay connected with your customer. So that's, that's my my banner cry, which is just get reconnected with your customer. Have a coffee, have a phone call. Sometimes it's weird.

Sometimes we get shy in marketing. Uh, if we weren't so shy, we'd be in sales, right? And so the podcast can be a great way to facilitate that conversation of getting on the phone with them. If you don't just wanna randomly call them up.

Guy: Yeah. Yeah. Well, and those, uh, I mean, you know, there's, there's two sides to, uh, to marketing.

s kind of like the awareness [:

Casey: Yeah. I mean, there's so many steps we, we take out there. We, and we bifurcate all of the different options and the different analytics, right.

To understand how. Are these people aware of this? Are these people, you know, captured by us? Are they a known name? Are they this, they that? We try to work them down the funnel. I am blowing up the funnel, right? Sound gram, he flipped the funnel and I'm just like, throw it out the window. Who cares? We don't even need it.

You take all those contacts and instead of throwing them down the garbage disposal to get churned up into some mush for sales, you just do one-to-one phone calls, have conversations with these people, interview them on a podcast, and then do business together.

Guy: Yeah, yeah, yeah. Makes sense. And, uh, um, so, uh, what do you, uh, what really though, fires you up about, uh, about this?

Are you, um. [:

Casey: You know, I had coffee with a customer and I, it was actually in Atlanta, funny enough. Um, I, and went to a Starbucks, and you know how it's some stupid expensive coffee and it's not even that good coffee in my opinion.

Uh, and so you get a coffee, but you know what? In five minutes, they were able to explain to me the challenge they were facing. It was a particular situation, it's kind of B two, B2C, so they were selling to businesses who were selling to consumers, and they had this weird thing they had set up. But in five minutes I understood what their challenge was, and I understood also how I could help them solve that with some of the things that I was doing in my company at the time.

take a moment away from our, [:

Right? So, again. Taking a step back from all of the marketing. Look, tech is great, but it got in the way. We, the barn door swung too much and we got too focused on the tech and we hid behind it and we got nervous and scared. We used to be the voice of the customer marketing, right? They would became tech nerds that just sort of did pretty brochures for sales.

And we were the print shop and we did all these weird things online and we got all techy. We lost the voice of the customer and sales kind of took that over a little bit, but no one really tells sales what's up? 'cause they know that you're trying to sell them. But we used to have that voice. So I'm just trying to get marketing to recapture the voice of the customer and be the, the most informed person in the boardroom to be able to answer this is what they're going through.

This is what we gotta [:

Guy: Yeah. Yeah, yeah. No, and I think that, uh, that really makes sense. So now you, uh, you've written a book, um, and, uh, you used your podcast, uh, to write that book. So tell us about that experience and, uh, how your book is doing and what your book is all about.

Casey: I took 20 years of experience and marketing automation. Put it in a book right. You still need to use these things because you're gonna still need to nurture people. Marketing automation can be great at capture, nurture, automate, and then report, show some ROI. You still need that, right? So I'm not saying throw everything out.

that can help them to their [:

And marketing automation can be great for doing that. So I definitely encourage anyone. To go out, get that book, it basically talks you through, there's 10 steps, uh, for rolling out marketing automation. One of the big things we found, just like how tech gets in the way, features get in the way, and we found that people got all Googo Gaga about certain features and marketing automation that they didn't even have the ability to use because they didn't do the groundwork early.

We got sold some cool features and then couldn't actually use them. Because they didn't do all the homework, right? So I, I lay out like a roadmap for where to start, what to do next, third, fourth, fifth, sixth. And there's a quick quiz at the beginning of it that helps you figure out where you're at, what your very next step is, and also how you compare with everyone else.

Guy: Yeah. So, uh, and the title of your book is, um, marketing Automation Unleashed. So yeah, that's it. Unleashed. Yeah, the thing is fantastic.

d people just need to let it [:

Guy: Yeah. Uh,

Casey: that's pretty sad. That's pretty sad. Yeah. So we are all about helping people actually use the tech.

Guy: Yeah. Yeah, yeah. Well, and then, um, and how does that fit in with, uh, some of the podcasting stuff that you're doing?

people see it and sometimes:

Sometimes it's just 'cause there was like. A cool picture on the, the artwork and people clicked on it, but like it was, I like, there must be something else I could do to create thought leadership for my company and teach people a better solution. So I looked around and I thought, well, [00:20:00] what about a podcast?

I've been listening to them for years, and so I launched the pod. The problem was. There wasn't a ringmaster around to help us at our company, so we had to figure things out on our own. What kind of microphone should you get? Should you get an expensive one? What, you know, how, how do you do a podcast? And so I just started and I started it ugly and I started a little bit messy, but I realized very quickly it was a passion of mine.

When I had a chance to sell that other company, I went all in on a podcast agency and we've really recently expanded to community. 'cause we realized that. Podcasting starts the relationship off beautifully, but there's nothing quite like a community to keep those relationships going.

Guy: Yeah, yeah. So, uh, now how do you see, uh, ai, uh, in your future and in your podcasting business?

What are you, uh, what are you using there?

n boarding school, being all [:

And, and, and these friends of mine, um, one in particular said, you got about five years. It's like, it's like Joseph, the Technicolor Dream Cup, right? You've got. Five years of bumper crops. You can use this AI thing, you can do amazing things with it, and then things get weird. So right now what I'm doing is I'm focusing these next five years on human connection, right?

My why as a as, as a human, as a person and as a leader of this company is to create human connection. That's what I'm doing. And so we're creating human connection, but we're also building an audience. It's gonna be so important to have a group of people that trust you. As things get noisy with ai, there's so much out there.

ing's gonna get age agentic. [:

Saving it up. Mm-hmm. And I've been building that audience and, and leveraging that, um, to really help people. Right. People can understand. I'm here to help. I'm here to help them grow their business, their company now. And um, when things get really weird, I'll still be doing that and they'll go, I don't know, not sure about all of these fake things, but I know Casey's real.

ying to enter into, into the [:

Casey: Yeah, the advice is, it's gonna sound like a broken record. It focus on the humanity and then stay in the loop on the technology because the tech is gonna continue to. Evolve rapidly, and you wanna stay at the forefront of that. But also you need to ground yourself in the humanity because that's gonna create the best content.

That's gonna create the best results. And also you're gonna stay centered on what actually matters, which is your customer. Hmm.

Guy: Yeah. Yeah. Um, you know, that's, that's really interesting that you put it that way. The thing that's kind of, uh, scary to me is, uh, a lot of younger folks, you know, like to play with the technology.

. So they have to break that [:

Casey: Yeah, it's the, it's the one-eyed man, you know, in the land of the blind is king, so the one person who looks up from the iPhone and the iPad in the restaurant, in the networking event, in the business meeting is gonna be the one that gets. Gets the deal, gets the success, understands what's going on, uh, gets the context for the situation.

Uh, so the best thing we can do is, you know, stay grounded in humanity and then embrace the technology.

Guy: Yeah. Yeah, it makes a lot of sense. Uh, Casey, uh, thank you so much. Uh, this has been, uh, really interesting and I like your concept of, uh, you know, as much AI and technology is out there, it's the human connection that really makes a difference.

u, uh, to, uh, find out more [:

Casey: You know, uh, the solution to disconnected marketing is connecting to your market. So I call it connect to market. Don't go to market, connect to market.

And look, I'm just here to help. And I, we talked about all the games. People play no games. Shoot me an email, Casey, CASE y@ringmaster.com say. Ask questions. You know, I'm happy to give you some suggestions. What microphone to get some simple things like that, what questions you might want to ask your customer if you actually get them on a Zoom call.

Start dirty, start ugly. Just get some conversations going, but shoot me a note. Um, happy to chat with you there. Check out the book on Amazon Marketing Automation Unleashed. That's the, that's sort of a. A groundwork that you'll need behind the scenes as you go hardcore on connection. And, uh, and then yeah, check out the podcast hardcore marketing.com.

g.com, casey@ringmaster.com. [:

Casey: Absolutely. Yeah. How whatever's easier, you know, even go to ringmaster.com you can chat, right?

So I am available however I can help. I'm here.

Guy: Fantastic, Casey, thank you so much. And for the audience, please stay tuned for many other videos in this series of the backstory on marketing and ai. And if you'd like to please go to marketing machine.pro relevant.com and find out more about my upcoming new book, AI and Marketing.

ey, thank you so much. Thank [:

Next Episode All Episodes Previous Episode

ProRelevant Newsletter Opt-in

Thank you, you have been subscribed.
Show artwork for The Backstory on Marketing and AI

About the Podcast

The Backstory on Marketing and AI
with Guy Powell
Dive deep into the dynamic marketing realm in the digital age with The Backstory on Marketing and AI, hosted by Guy Powell, the visionary President of ProRelevant Marketing Solutions. This enlightening podcast is your gateway to understanding the intricate interplay between data-driven marketing strategies and cutting-edge AI technologies.

Each episode brings to the table candid and insightful conversations with some of the industry's most influential leaders and analytics experts. They share their valuable perspectives and experiences on how to navigate the ever-evolving marketing landscape successfully. As a listener, you will be able to discover the most current trends shaping the marketing world and learn innovative ways to leverage AI to elevate your brand's presence and impact.

The Backstory on Marketing and AI is an indispensable resource for anyone involved in marketing, from executives managing to proactive marketers. Whether you're an executive overseeing a hefty advertising budget or a marketer at the forefront of a growing brand, this podcast is your resource for staying ahead in the competitive marketing world.

Tune in on Apple Podcasts and Spotify and be part of the pivotal discussions defining the future of marketing. Don't miss out on this chance to revolutionize your approach to marketing and AI. Subscribe today and begin becoming a more informed and strategic marketer. For more information, visit www.prorelevant.com.

Typical questions discussed in this podcast:
How is AI transforming traditional marketing strategies?
What is the role of data analytics in understanding consumer behavior?
What are the best practices for integrating AI into your marketing campaigns?
What is the future of personalized and content marketing with AI?
What are some AI success stories and case studies: Brands leading the way in AI marketing?
How can we best overcome challenges in adopting AI technologies for marketing?
How can we measure the ROI of AI-based marketing initiatives?
How can we build a customer journey map leveraging AI insights?
How can we maintain privacy, data protection and cyber security in the age of AI marketing.
How can we build a skilled team to leverage AI in marketing?
What is AI's influence on social media marketing strategies?
What is the right balance between AI automation and the human touch in marketing?
What are the limits of using AI to support Chatbots?
How can young marketers leverage AI in their careers?

Topics Discussed:
AI Marketing
Data Analytics
Predictive Analytics
Brand Strategies
AI Ethics
Creative Advertising
Marketing ROI
Customer Journey
Content Marketing
Chatbots
Data Privacy
Social Media Strategies
Small Business Marketing
Prompt design and engineering

Main Questions:
What is the difference between ChatGPT and Bard?
How can Canva be used for image development?
What is a Large Learning Model (LLM)?

Testimonials:
In this fun and easy read, Guy provides a roadmap on how you can navigate through today's choppy waters and come out on the other side with a successful, metrics-based marketing campaign.
Jamie Turner, Author, Adjunct Instructor, Speaker, and Consultant

Guy does a great job of outlining marketing strategies adopted during the pandemic through some very insightful case studies and is a must-have for marketers.
Sonia Serrao, Senior Director, Brand Marketing at Tarkett

Sign up now for more episodes.