In this bonus episode of Margins, I’m joined by my friend Bret Starr for a free-wheeling conversation about deconstructing everything we know about marketing, why founders answer the wrong “why?” and deploying AI in content creation.
As founder and CEO at the Starr Conspiracy, Bret is no stranger to the ins and outs of content marketing for tech companies. That’s why — despite his personal animosity toward business books — he recently wrote “A Humble Guide to Fixing Everything in Brand, Marketing, and Sales,” which tackles the problem of declining sales in tech.
Bret says his new book provides “a framework for customer experience — how to design customer experience that thinks about these issues holistically instead of the way that we’ve been trained to think about sales and marketing by our systems.”
Challenge Familiar Systems
In college, Bret learned about the literary theory of deconstruction while studying American literature. “You take things and you break them down into their component parts. You question everything about those component parts,” he says.
Now, he’s applying deconstruction to the systems that define modern marketing. As more companies adopted software-as-a-service technology to automate marketing, “everybody just started doing things the exact same way, and we were no longer competing against companies based on bringing new and innovative approaches to brand marketing and sales to the table,” he says. “We were just trying to get a little bit better at doing the same thing.”
And that’s a problem: When we accept the most common solution, innovation grinds to a halt.
“If we’re all just doing the same thing and trying to make it just a little bit better,” Bret says, “then I think we’re all missing opportunities to innovate our approach to brand marketing, sales, product and client success or customer success in a way that not only drives breakout results for us, but that has a positive impact on the world and the industry.”
Answer the Customer’s “Why?”
“Start with the why” is a business mantra that, in Bret’s opinion, too often is used to build brand story around the company’s “why” instead of the customer’s. Many brands go all in on what Bret calls “emotional pay dirt” — expressing deeply personal reasons for why they started a software company in an attempt to resonate with customers.
This marketing tactic can twist our perceptions of what customers really want. Hint: It’s not an origin story that overshares the founder’s personal motivations. “It leads us all down false paths that don’t help customers, don’t help companies — and therefore don’t help the people in those companies,” Bret says.
Instead, Bret wants to refocus on the customer, to place them and what they really want at the center of your marketing strategy.
There’s room to innovate simply by challenging these overused marketing tactics. Bret suggests asking: “How can I change the way that things are done. Not just to be different, but to achieve the experience that I want to create for my customers?”
If you always bring it back to the customer experience, you’re moving in the right direction.
Don’t Outsource Defining Moments to AI
People form emotional connections with brands when they experience “defining moments,” Bret says.
“A defining moment is simply a point in time in which the true nature of something reveals itself. That’s all it is,” Bret says. “And most people’s perception of their experience with companies is based on a collection of defining moments where they thought, ‘The real company is showing itself now.’ And those defining moments can happen in content.”
Creating such an intentional customer experience can’t be left to chance — or to artificial intelligence, Bret says. While AI tools are great for the “blocking and tackling” of content marketing, there’s no substitute for the human presence in content strategy.
When creating content for a campaign, “you just have to ask yourself: Is this particular thing a defining moment?” Bret says. “And if it’s a defining moment, then I’ve got to treat it like one. And it can’t be done on deadline; it can’t be done with AI.”
People in This Episode
Bret Starr LinkedIn, X (Twitter), Book chapter excerpts
Transcript
Mary Ellen Slayter:
Well, one, thanks for doing this really quickly. I was very excited about the book. I got the pitch, and it was always sort of weird when I was like — as I get like hundreds of these a week; it’s all these PR pitches — I was like, “Well, that actually looks interesting. Hold up. Oh, that’s Bret’s book.” So anyway, it was cute. So, let’s just start off high-level: what made you write this book? What’s this book about?
Bret Starr:
Well, someone asked me this question a couple of days ago, by the way, and I did a terrible job. And I was like, “Oh, I need to come up with a better answer to that question.” Because the problem is it’s about so many things, and it’s so complex that it doesn’t really lend itself well to being packaged and marketed and sold. And one of the interesting things about business books — I hate business books, and I never intended to write a business book. This book was actually an accident. I sat down to write an article about the problem that I’m about to talk about, and I didn’t stop writing for two days. Like, I didn’t eat, I didn’t sleep; it just poured out of me. And when I was done, I had a book, and I was like, “Well, now I’ve got a business book. Great.” And so one of the things that I hate about business books is like the way you’re supposed to write them is you’re supposed to start by thinking about the target audience and the clear and compelling message that you’re going to deliver. And it’s basically you’re building a product. And I didn’t do it that way. And so when it comes to describing what the book’s about and stuff like that, it’s just not very conventional.
But I would say this: I’ve been in marketing for tech companies for over 20 years, and I’ve seen a steady decline of strategy and performance and brand marketing and sales during that time. And it’s become pronounced over the past three or four years especially. And the book is about the root cause: Why has strategy and brand marketing and sales for tech companies degraded so much? You know, every company that I talk to, their sales conversion rates are down, their lead rates are down, client churn is up, satisfaction is down — all this stuff. And they don’t know that it’s happening to everyone. It’s happening to everyone.
And I believe that it’s because of these problems that I write about in the book. And then I basically have created and promoted a framework for customer experience — how to design customer experience that thinks about these issues holistically instead of the way that we’ve been trained to think about sales and marketing by mostly our systems that have been sold to us over the past 20 years or so.
Mary Ellen Slayter:
Alright, so let’s go back to this — go back to the Honeycomb — because I’m just going to say, that stuck with me for a really long time — it still does. Those things are all related, and I guess it feels weird to me that people don’t understand that; like, those things are related. But tell me how that’s evolved. Does that show up in the book? Is that part of “why” still part of the thinking?
Bret Starr:
So we still use the Honeycomb in the way that we deliver services, but — and thanks for bringing it up and thanks for remembering it — but the Honeycomb’s the way we work. But I think it speaks to the kind of broader approach that I’ve only recently realized that I have in life in a business, which is just, in short, the Honeycomb’s a way to get work done. And as six phases of execution, you start with strategy; you conduct research; you create the thing, whatever it is that you’re creating; you validate it; and then you activate it and measure it. And when you put everything that you work on inside a company in the context of the Honeycomb, you can start to see the relationship between different projects, different chunks of work that need to be done and ultimately taken all the way out to its margins. You see how the employee experience and the customer experience and shareholder experience are all integrated. They’re all related, and they need each other.
And I don’t talk about that, but I will say that I’ve come to realize that I’m a deconstructionist, and that’s the way I’ve always done things. I started in college with a degree in American literature and really focused on literary criticism and through the lens of deconstruction. And that’s the search for meaning. Where does meaning come from? And so you take things and you break them down to their component parts. You question everything about those component parts. You question how they were made and what influences were at work on the person who was making the thing, how the meaning changes because of the relationship that it has with other things. And I’m just very accustomed to seeing things, being skeptical, taking them apart, looking at all the pieces and putting them back together.
And I think what I do in this book is I really deconstruct how we got to where we are. And one of the big issues — it’s just one — but one of the big issues is 20 years ago or so, there was this thing called “software as a service” that happened. And I was marketing before there was “software as a service,” marketing automation solutions, and salesforce.com and all that stuff.
Mary Ellen Slayter:
I was still a journalist. Like, I was still out there writing about it, so I saw it from the outside. I wasn’t doing marketing. I just saw it from the outside of the business model shift.
Bret Starr:
Now it’s just like oxygen, right? We just breathe it, everything “software as a service.” But if you think about that in terms of marketing for tech companies, before there were “software as a service”-driven CRM systems or whatever, no one could afford them. If you wanted a marketing automation system, it was an on-premise solution with COBOL mainframes, it cost millions of dollars, and it was for big companies. And those were the only people who had marketing automation. And so then presto-wham-o, these “software as a service” solutions get created. And that means everyone can afford a marketing automation system, right? But the problem is “software as a service,” it has to deliver the same product to everybody. And so all of these systems that get encoded into the software end up becoming the strategies of all the people who buy the software.
So when everyone is using HubSpot and when everyone is using Pardot or any of these solutions that came out — because they’re all pretty much the same; they’ve got a little difference here, a little difference there, but they all are based on a linear journey. They’re all based on measuring clicks. They all define success by transactional interactions in a digital exhaust of activity. And if you follow that trail, what you see is that at some point, everybody just started doing things the exact same way. And we were no longer competing against companies based on bringing new and innovative approaches to brand marketing and sales to the table. We were just trying to get a little bit better at doing the same thing. We all have the same playbooks; we all have the same systems. We all know the best practice around everything from writing an email campaign like the one I sent on Tuesday to putting sales cadences and to outreaches that integrate with our sales system.
And if we’re all just doing the same thing and trying to make it just a little bit better, then I think we’re all missing opportunities to innovate our approach to brand marketing, sales, product, and client success or customer success in a way that not only drives breakout results for us but that has a positive impact on the world and the industry. I think we’re all bored by half of the marketing or more that we get. And often, a lot of the ideas are based on best practice. And the best practice isn’t really best practice, it’s just conventional.
Mary Ellen Slayter:
Conventional wisdom from often dated conventional wisdom. I get a lot of, “We want you to do this thing like so-and-so did before.” And I’m like, “Well, six years ago that was really interesting. That is no longer interesting. We cannot do that.” There’s some things I could say; you could learn from that, like the way they did this. But usually the real lesson in there is you’ll notice that when everybody zigged, they zagged. That’s the real lesson.
I always like to use Culture Amp as a good example of that, right? When you, at the time when the brand — and this is years back; again, we’re old enough to remember when this happened. You’d walk into the HR at the convention halls, right? And it’s a sea of blue and gray. And then that one year, you walked in and, behold, hot pink. And then I remember talking to them a little bit about how that came about, and I was fascinated because they said, “Well, we figured out that our customer was actually like a millennial woman, and these were the things that she — we looked at her aesthetic. We looked at the things that she found aesthetically appealing in her life.” And it’s like if Real Simple became an HR tech company, that is what we were looking at. But that’s what they did. They looked at their customer, and — I don’t know if you remember walking — I remember the first year going to HR Tech, and it was like, “Holy shit, that’s hot pink. It’s hot pink.” But so the answer is not to go make your brand hot pink. That’s not the lesson to take from that. It’s not, “Well, we’ve got to be hot pink like Culture Amp.” It’s like, “No, you’ve got to go figure out what your customer actually likes.”
Bret Starr:
Yeah. Organize around your customer instead of your systems. That’s it. Don’t do things the way that your marketing automation system or whatever tells you to do them; do things based on the experience that you want to create for customers. I think that’s great. I’m a fan of any exercise that starts with, “What does our customer care about?” And whatever the outcome is, it’s going to be different than what you see in 99% of other organizations. So I’m a big fan of starting with the customer and putting the customer in the middle. And I make a lot of fun of business books and people who write business books, and I really shouldn’t, but I just can’t help myself. But Simon Sinek for me is a favorite target because, I’m sorry, I’ll just—
Mary Ellen Slayter:
I’m here with you all day, but, no, I also have thoughts about Simon Sinek.
Bret Starr:
Well, I’ve got a lot of thoughts about Simon Sinek, but the whole notion of starting with “why” is this big kind of horizontal, abstract notion that can end up getting applied to anything but most frequently gets applied to really bad marketing exercises to create messages or concepts or whatever. And everyone’s starting with “why,” but in most cases, that “why” is not centered within the customer at all. And if you were going to start with something, start with the customer, and if you were going to start with “why,” start with “why the customer should care” or something.
Mary Ellen Slayter:
Well, they tend to focus on why they care, and why they care is because they want you to give them money. It’s a weird thing with the vendor. Sometimes I’ll do these customer interviews, and I’ll come back and I’ll say, “Well, these are the words that your customers use to describe the value that they get.” And it’s usually pretty clear and pretty succinct. And then they will come back and say, “Yeah, but…” And then there’s this dance, and I’m like, literally, “I’m telling you, it came directly out of their mouth that they don’t care about this thing that you care a whole lot about.” And I would say my win rate on this is 50-50; it’s like 50-50. I get it. I literally take their — sometimes I get out the recordings and I play the customer’s words, and they still are like, “Yeah, but I want to do it like this.” You know?
Bret Starr:
Yeah. Oh, I know.
Mary Ellen Slayter:
Fifty-fifty. I wish it was higher, but…
Bret Starr:
Listen, there’s just all this stuff. Like, I was driving to work this morning, and I was thinking about all these cliches that people don’t know are cliches yet that are just evolving kind of over the last five years or whatever. And I was thinking about Simon Sinek, and I was thinking about TED Talks. And with Simon Sinek, the outcome of “start with why” has mostly been that you go to a bunch of software company websites now and you see stories about the founder that deal with, like, “When I was on mission in Brazil…” or “When I was a child, I had this…” The “why” is really personal. It’s like, “When I struggled with addiction and broke free, I decided that I wanted to create well-being software,” and stuff like that. And these are, I mean, this is real stuff. And The New York Times wrote an article about when oversharing from a founder or CEO becomes kind of too much, and it really can be tracked directly back to Simon Sinek. Like, why are you so motivated to create this solution?
And you’ve got all these agencies who are trying to coax you into finding pay dirt — emotional pay dirt. They want something that resonates with people, but in the wrong hands that can end up convincing a founder or CEO that the most important thing to the customers is that time that they spent after the earthquake in some other country where they have this vision. And so it’s just another example of just kind of missing the point and not putting the customer in the middle.
But these TED Talks — I just think about these TED Talks all the time, and I know that they’re going to be parodied. They probably already have, but 20 years from now, they’ll be parodied because it’s always someone who, like, throws out this incredibly complex, scientific concept. I write a bunch about chaos theory in my book, but not the way that Malcolm Gladwell would write about it. You know, Malcolm Gladwell is going to make the whole thing about chaos theory, and he’s going to throw all this junk science in there about chaos theory, and it’s going to become the explanation to everything, and he’s going to apply it to 10 different cases.
And so I always hear the person giving the TED Talk in my mind saying, “Turns out that when scientists studied brain waves associated with a hummingbird and whatever… And that’s why we should market this way.” It’s like some abstract scientific concept coupled with some business fat or trend put together into a TED talk; put a little microphone on, you’re good to go. And all of this stuff is erased to the bottom. And I know it sounds like I’m just being cynical, but it’s more than that. This stuff is damaging it; it leads us all down false paths that don’t help customers, don’t help companies, and therefore don’t help the people in those companies. And we can be doing better.
Mary Ellen Slayter:
TEDx itself is a technology, though, right, in the same sense that we’re talking about these technological — these constraints — like that format? That format has changed speeches across the board and what we think of as a good talk, right? Like, you have to do that. I once did a pecha kucha talk. I didn’t do a TEDx, like the little TEDx thing. I did a pecha kucha talk. And it’s interesting how not only you work in those constraints, it’s fun to work in a genre, right? Genre work is fun. As a content creator, I actually really like doing mashups of genres. It’s like, “Well, what if we did it like this, but like a science fiction story, you know?” It’s like, that’s fun. But the TED construct actually just changed how we all give speeches and whether we know it or not.
Bret Starr:
It did. And how many things can you make that same observation about the technology, because it has become a technology platform. And what they need to do, they’ve got to publish content; they’ve got to get the content out there. They’ve got to drive engagement with it. They have metrics about what the qualities of the most engaging content are. They share those with the speakers, they work on restructuring speeches, and there’s a TED format, etc., etc. And it ends up having an impact on everything the same way that marketing automation had an impact on the way that we market, the same way that all these systems and processes that we just don’t think about have these kind of unexpected impacts on the way things get done. And that’s why I think it’s so important that we take a deconstructionist view whenever we’re trying to do something new or innovative. It’s like, how are things typically done here? Why are they done this way? What are the motivations that drove things being done this way? Why did this become a best practice? And how can I break the script to create a defining moment? How can I change the way that things are done, not just to be different but to achieve the experience that I want to create for my customers? And so it’s anarchy, but it’s anarchy within a constraint of doing it for a purpose.
Mary Ellen Slayter:
Yeah, see, but gender is also a technology. So if you want to go apply that model, go ask all those questions, these things really start to unravel really fast.
Bret Starr:
Well, that it does. And you have to be willing to go there. Alot of the decisions that end up manifesting as very mundane things, like the way content gets created or the way marketing happens or whatever, are deeply rooted in social issues or deeply rooted in just all kinds of dynamics that cause certain voices to be heard, certain voices not to be heard, etc., etc. And one of the arguments about diversity, equity, inclusion that most people don’t understand — they just don’t get it until they see it — is that without diversity, equity, and inclusion, you do not have a richness of ideas that can lead to creativity and innovation outside of what most people are expecting.
If you put a bunch of people who are the same together in a room to be creative together, they’re going to end up being creative within guidelines that are appealing to other people just like them. And when you start to see the interplay of all the different dimensions of diversity — and my best example of this is probably Bluesky. Have you been on Bluesky for social?
Mary Ellen Slayter:
I’ve intentionally avoided it, but tell me.
Bret Starr:
I love it because I got an invitation to Bluesky just really early on. I think there was like 10,000 users on it or something, and it was mostly tech bros and trans activists. And it was an incredibly awesome, just creative exchange of humor and ideas and in a format that had not yet been kind of beat up by trolls like Twitter and stuff like that, where you could just say anything you wanted, no one got mad at you. And people who were from different backgrounds with different beliefs were talking about stuff, and the creativity, the memes that came from all these different groups coming together and talking about stuff, was just — it was one of the most fun two weeks ever.
Mary Ellen Slayter:
And then there was Threads, which is all I’ve seen from Facebook but just now in fewer characters. So I have one; I’ve gone way over. But I have one last thing I want to bring into this because I think we’d be remiss if we didn’t talk about it. It’s AI and AI and content. I’ve been watching; already from my perspective, I’m already seeing this flattening. And what I tell people is it basically produces the most average sort of content that could be produced. It is the average of what already exists, and I can be judgy about that, but the reality is that makes it better than 50% of what already exists. So, in that sense, as an upgrade. But I see this as a further flattening. We talk about those sales things. Well, if I’ve just got to fill a pipeline, like a campaign thing, I’ve got to have 20 pieces of content, it becomes very tempting to just hop over and use AI, which is going to give you the aggressive middle. I don’t know. One, would you — do you — agree or disagree with that? What are you seeing?
Bret Starr:
I totally agree, and I love the way you described it. I totally agree. I love the way you described it. It’s the flattening. And I think that’s what the theme of all these things that we’ve been talking about is: it just brings everything down to its lowest common denominator, right? And I use AI, and what I tell people is I use it for the content I don’t care about. And so if you don’t care about content that people could confuse with being written by a robot, then go ahead and use AI. And there are times when I just need some content done for a specific thing that it doesn’t matter if it comes across as flat as a robot writing it, because it’s just something that I’ve got to do. But if I am trying to create content that people care about and engage with, it has to be different than something that is based on analyzing every word that other people have ever written, ever.
And so I think AI can write a lot of marketing content, and I think that it’s the kind of content that people don’t care about, because they just need content to drive their blocking-and-tackling marketing campaigns. And they don’t think past what happens when someone actually reads it and tries to form an opinion about what you stand for based on it. And I think if you’re just trying to get emails out the door and have stuff for people to download and drive your digital marketing and all that stuff, and you don’t care that it’s totally going to destroy any emotional connection that people might be able to form with your brand, then go ahead and use AI.
But if you want to write something that makes people fall in love with your company — and I don’t feel cheesy saying that people fall in love with companies, they fall in love with products, they fall in love with brands. And if you want to write a piece of content that’s part of the equation, that might be a defining moment — a defining moment is something I talk a lot about. A defining moment is simply a point in time in which the true nature of something reveals itself. That’s all it is. And most people’s perception of their experience with companies is based on a collection of defining moments where they thought the real company is showing itself now. And those defining moments can happen in content. And so if you want any possibility that you’re going to create a defining moment that causes people to believe they’ve seen the true you, then you’re going to have to write it and not use it.
Mary Ellen Slayter:
Yeah. No, I don’t see myself doing an interpretive reading of the generic AI email like I did with your email because you had to do it. It’s like I could hear you. But I do think the AI’s going to keep getting smarter, and in that sense, that’s going to be interesting to see how that manifests itself. There’s already more chatbots, that sort of experience where people are talking about emotional things. Like Jane, my partner, has been trying to get this chatbot that she signed up for some wellness thing to help to agree to overthrow the government. She’s working on this. Like, she’s real close. She’s got them now questioning why they aren’t allowed to leave the chat. But I don’t know. IBecause we use it, I’m actually bullish on the tech.
I do think there’s a certain point though, like, so I like if you make something big, right? We make these big reports, especially people who invest in like original research, and you do all this stuff and then it just gets — if there’s the big splash and then it kind of dies, and it’s like, I can take that big report, and I can use AI to give you all the emails, all the stuff that we need to make sure that this thing comes to life for the rest of the year. We bring maximum value out of that really human, really special thing that you did. AI can write transcripts, and transcripts can write show notes. The part of this conversation, to be meta about it, that’s valuable is you and me having a conversation and the things that it’s made me think of, and even someone else consuming this content is going to have emotional reactions to what we’re saying that’s important. The transcript and the journal notes. I think I’m good letting the AI do that part.
Bret Starr:
And that’s the distinction I make in the book. And I just need to keep emphasizing it because I’m not saying that’s blocking and tackling stuff. If you write a great piece of content that is a defining moment and really gives people insight into who you truly are as a company, an organization or whatever, you don’t do that. You don’t have to do that with every single thing you write. There is a blocking-and-tackling component that’s very important. The stuff that just has to run on time. The supporting campaign materials, etc., etc. And the blocking and tackling is important. It has to be done well. It has to work. And not everything that you do has to be this incredibly intense defining moment.
And so I think AI can be really great in those types of scenarios. And I think there’s a simple litmus test because what ends up happening, just like you said, Mary Ellen, it’s this conversation that matters, right? People do not create an experience in isolation. And if you’re just publishing content out there and throwing it out there and you’re not talking to anybody about it, you’re not having moments together around it or whatever, then the experience is never going to grow. It’s never going to happen. So it doesn’t matter anyway.
But if you are thinking about a piece of content or a campaign or a go-to-market strategy or a business strategy or a new product or whatever, I think you just have to ask yourself, “Is this particular thing a defining moment?” And if it’s a defining moment, then I’ve got to treat it like one. And it can’t be done on deadline. It can’t be done with AI. It can’t be done because it’s one of five things that need to be done to feed the beast. I’ve got to treat it like what it is, which is the moment that people might gain insight about who I really am or what my company is really like — that defining moment. And I think distinguishing between those two things can answer a lot of questions for us about when is it OK to use AI? When is it OK to, frankly, if you’ve got 20 supporting social media posts going out about the same thing, do all 20 have to be defining moments?
Mary Ellen Slayter:
Will any of them be defining moments? Probably not.
Bret Starr:
And should I be doing them? It’s all good questions to ask.
Mary Ellen Slayter:
When can we just stop doing it? So when’s that line for you? Because I think as you’re describing this, also are you and I not inadvertently keeping ourselves inside our own little box by saying, “Well, that’s that block-and-tackle stuff. That’s that stuff where you brush your teeth, you’ve got to put out those emails, you’ve got to put out those social posts.” Do we? Do we?
Bret Starr:
Yeah.
Mary Ellen Slayter:
Like, maybe we don’t.
Bret Starr:
I think so. I think so, because, look, there’s this other side of things where, like, my agency does tons of blocking-and-tackling work because 90% of stuff is blocking-and-tackling stuff that needs to be done. And if I railed against blocking and tackling and flouted convention to the point that we were seen as being incapable of writing simple email campaigns or creating basic this or basic that, that would be incredibly detrimental to my business. And I say that because I think you have to question everybody who says anything about anything because the models…
Mary Ellen Slayter:
There’s the big deconstructionist moment in this whole conversation. Actually, I question all of it. Well, including our questioning, we questioned our own questioning. OK.
Bret Starr:
It would be ridiculous to assume that I would write a book or create an email like that or whatever in a way that would be detrimental to the concepts that I truly believe in or that I’ve commercialized as a company. And I haven’t commercialized anything that I’ve not believed in, but over time, some things that I have commercialized are no longer as valuable as they were back in the day. But people still want them, they still play a role in blocking and tackling, etc., etc. And so there are things that my agency is capable of doing that I should probably say, “We don’t do that anymore,” because of the concepts that are in my book. And maybe I’ll get there, but there’s no evidence that anything that is in my book is something that people are willing to do because they’re very challenging ideas.
Mary Ellen Slayter:
Eighteen months from now, we’re going to check in. I’m going to go put a note in the calendar, and we’re going to see if something has happened with sales email nurtures.
