How to Tell Sexy Stories About Unsexy Brands

0:00From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

0:22When you're trying to figure out how to market a product or a brand, some jobs are easier than others. When you have a sexy brand, like if you're like a Nike or an Apple, it's inherently pretty easy to do great work, right? You're talking about some of the most valuable, most loved brands in the world. This is David Lee. He is the chief creative officer for Squarespace, which is not exactly Apple or Nike, which is to say, you know, it's a good company and people use it to make their websites. But nobody, certainly 10 years ago before David Lee showed up, thought of it as sexy. When it comes to software, so already inherently you're dealing with selling binary ones and zeros, right?

1:07You don't have like an object per se. So it makes it like intrinsically like already like much harder to do a lot of storytelling around that. So how do you make ones and zeros sexy? How do you tell that story? I was excited to talk to David about this because he has done exactly that and been very widely recognized for it. I will just read you a tiny bit from an Ad Age article, which had announced that David Lee is Creative Awards Brand Chief Creative Officer of the Year. That is just from the headline there. Since he took the helm, I'm reading from Ad Age, since he took the helm at the website building and hosting platform in 2013, it's become famous for its entertaining and platform-spanning campaigns starring numerous celebrities, including John McEnroe, Jeff Bridges, Idris Elba, Wynonna Ryder, and John Malkovich.

1:53The latter earned an Emmy. And okay, that's that from the adage. Now back to me. So what did he do? And what does he understand about telling stories about things that maybe aren't inherently difficult to tell stories about that anybody can use to tell better stories? Well, that's what's coming up after the break. Hey, everybody, I'm John Small. And I'm Dan Bova. And we wanted to tell you about a new podcast from entrepreneur media called Dirty Money. That's right. On this show, we tell you the true crime stories of some of the world's worst scammers, schemers, con artists, fraudsters, and even murderers.

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2:58All right, we're back. I'm talking with David Lee, the chief creative officer of Squarespace. And just for some context, David had a long background on the agency side, working inside of ad agencies for a ton of different brands and then went in-house with Squarespace, which was a different kind of experience for him where he got to really immerse himself in one brand and understand how to tell that story over a very long period of time. And we're going to start here by him diagnosing a problem that Squarespace just exists in, which is that it's a tech company. And the way that tech companies often talk about their products is not always inspiring.

3:43I think the tech world especially tends to be very much about telling exactly what they do on their sleeve. And what we also tend to do is we tend to look at our competition left and right and kind of see what they're doing. And it becomes this vicious circle of everyone looking and feeling the same and also actually saying this almost the exact same message, just like one degree apart, because I feel like we're in this void where we're just looking two inches in front of our face. And one of the exercises I always do when I, when you have a new client or specifically when I joined Squarespace 10 and a half years ago is you're trying to find a new way of breaking out of this sea of Satanists, right?

4:27So a lot of that is trying to find a different filter or a different lens on looking at a very similar problem that a lot of the competitors are looking at. And I've always found it way more interesting to pull in references or insights from completely other sectors and other categories, just definitely not our own, because I think that's the dead end to what I actually just explained previously. So when it comes to websites, I wouldn't say websites is the most fertile, interesting place to come up with great new innovative ideas or to do some breakthrough storytelling, right? You know, it's pretty, yeah.

5:05I mean, it's funny because websites are a place where all sorts of amazing things happen, but websites are so abstract at this point that it's, I don't know, it feels like trying to figure out how to tell stories about roads or sidewalks or something, right? It's just a place where things happen. It's the plumbing of the internet. Yeah. Right? That's exactly right. And I'm glad you mentioned that because that doesn't sound too interesting, right? But it's my job and it's our job collectively to try and figure out how do you make that exciting? You mentioned the word like sexy. How do you make websites and web publishing sexy?

5:41And yeah, that's kind of been a very decade-long kind of challenge over here that we've been trying to solve and me in particular. So here's like the mental exercise that I do and that I did with Squarespace. And hopefully there's something here that the audience will find insightful. I love a mental exercise. Tell me. So I like to do, what exactly are we? And I will try and find different industries and different businesses to kind of relate to. So I actually think we're a real estate company, right? When you're talking about the plumbing of the internet, I actually consider ourselves, we sell online real estate.

6:19And what I mean by that, and this is also when we had this surge of social media companies coming up and people were trying to think, well, why do we need websites anymore versus social media, etc. And what I always tell people is that there's a very big difference between renting and buying. And if you're going to build your personal brand in someone else's house, they can move the furniture around. They might be able to change the color on the walls. And worse yet, they might be able to put an ad on your front lawn. You're perpetually living in someone else's house. And I actually think it's the American dream for everyone to own a piece of the World Wide Web that they can call their own.

6:55So if you think about it, a domain, which is a crucial part of building a website, it's kind of like that acre of land. Maybe it's in upstate New York or something like that. And you may not even know exactly what you're going to build on it, but it's yours. right and i don't care if you have one pixel or one pixel by one pixel of the internet or 10 billion by 10 billion there's something really kind of permanent about owning a piece of the worldwide web and the beauty is that you could put a picket fence around that and build whatever you want inside and it's yours right and the reason why i use this kind of analogy is that there's a lot it's almost like the actually let me let me let me try i was trying to connect something together Give me a...

7:37Yeah, well, as you're thinking through it, let me tell you the connection that I was making as you were saying this, which is that I know that good marketing and good storytelling is about helping somebody see how something fits into their lives in a very meaningful way, which means identifying the familiar emotional component of it. And a very interesting thing that you have done here, I mean, it's funny because when you first went to a website is actually real estate. I was thinking like, oh, you've just made it less sexy. But then what you ended up doing is identifying that the thing that's meaningful about real estate is ownership.

8:17Because I know from my own experience about my own experience of buying my first home is that it felt distinctly different from renting it. Now I own a place. This is mine. And it's pretty magical. And I also remember that feeling the first time I bought a website, because it's also kind of amazing. I could post whatever the hell I want now to the whole internet. And that sense of ownership is very inherent in our sense of self. And that may be a particularly American thing. I don't know, because America is obsessed with ownership like that. But it is true, at least for a good audience. amount, a good chunk of audience.

9:00So maybe that's what you were doing. And that's the thing that you're laying out here. At least that's what I heard is that what you were trying to do is get to a place where you understood the emotional value that the concept of a website could have with people. Because once you've identified that, you know the conversation you're having with them. Am I right about that? You're 100 % spot on. And I always used to say, you get to learn a lot about someone as soon as you step foot in their house without saying anything. It's like the most intimate kind of like place and it's the official you, right?

9:33So I think there's something very permanent and timeless about owning a piece of this worldwide web and what we're discussing right here. And that actually kind of led to one of the biggest kind of insights to like, arguably one of our most successful Superbowl campaigns. Actually, this insight right here is that there's just this race of trying to buy up all this land before it's gone. You see people bidding for pieces of real estate constantly. And this insight actually led to a Super Bowl campaign that was based off of a real story. We collaborated with John Malkovich. And John Malkovich wanted to launch a menswear fashion line under his own namesake.

10:15And he told me the story that, unfortunately, when he went to register johnmalkovich.com, it was already taken by another John Malkovich. Not an actor, not a menswear fashion designer. And that right there led to this kind of like tagline that we said, like, that we put out, which was get your domain before it's gone. Right, right, right. Someone else was being John Malkovich, just for the joke of it. But yeah, that's great because that is the great fear on the other side of ownership, which is that you won't be able to own it. Yeah, the fear of missing out, the fear that you will never be able to purchase that piece of land, that idea will never kind of see itself into existence because you haven't figured that out.

10:58So like that call to action, that call to arms and that sense of urgency. And obviously, if for the audience, you haven't seen it, it's, you know, you could probably find it on YouTube, the comedy of John Malkovich completely flipping out and calling and finding the actual other John Malkovich who purchased that and the comedy that ensues was kind of gold. Yeah, it's kind of gold. Right. So, again, that analogy, it's kind of looking at what you do through this different lens will actually open up so much creative opportunity and to kind of be able to tell a story that you might not automatically think of right away.

11:34Yeah. Can you tell me a few other ways in which this insight about ownership led to great, engaging storytelling? telling? Sure. Well, just piggybacking off of this notion of ownership and real estate. So every one of us, when we walk out our door, our front door every single day, we curate how we look, right? We curate how we want to be presented out into the world, like in real life, right? The clothing that we wear, the way that we've styled our hair, anything. Exactly. Like you could be dressed to the nines. You could be super avant-garde. You could be really casual and kind of laid back, but everyone actually curates how we want to be perceived out in the world and how we want that first impression to actually be perceived.

12:22And so another place that we tend to pull inspiration from is the fashion industry, right? So fashion websites, not the clearest correlation when you just hear without any explanation, but I would argue the reason why I'm telling you this is that that first impression today will almost all certainly happen online. Right. And you can't hide as well online in the real world. You can close your door and kind of like, you know, hibernate and come out into the ether like a week later online. It's like, you can't, you can't hide. It's always on. And I use this saying that like, it's almost like your, your legacy.

13:02And that first impression is what returns from a Google search results of your name or of your company. And I always ask the questions, What do you want people to see when they actually make that first impression? It's the reason why when I'm looking at a restaurant, I'll almost always click on the link to their website. And I'll actually make a validation almost instantly if this is a legitimate kind of place. And I've actually decided to not go to a restaurant based off of what I saw perceived in that website. It's the reason why if I have a prospective candidate who wants to join our company, where I will search for their name and actually see what comes up.

13:39And within that first couple of links, I will make a judgment call on like, how do you present yourself? Right. How do you how do you tell your own story in your own official kind of manner? So I would argue that your website is is very much that first impression that people are going to have today and for years now. So it would behoove us not to look at different industries like the fashion industry and full inspiration from there. Right. So I'll give you an example. we've there's this thing about fashion trends change all the time right there in the fall winter collection looks vastly different than the spring summer kind of collection we feel that your website shouldn't be this like static set it and forget it because trends change all the time right you change you evolve right why should your website be this static thing that just stays for like the last 10 years.

14:31It should be a reflection of who you are at that moment in time. This is why we started to launch collections of designs and templates at Squarespace, right? So we were using the convention of the fashion industry to launch like a fall winter kind of collections of new designs. We're launching like a spring summer collection of new designs because we want people to understand that you should be updating this. You should be updating your fashionable first impression, both in IRL and online. Before you jump into that next example, I'm just going to tell you, as I've now heard a couple ways in which you started with product and then, as you said, look in other contexts and then end up with a great end result, whether that's an innovation to the product or a piece of storytelling and marketing.

15:15I kind of feel like saying this to you to see if this is a good distillation of what you're saying. It's almost like you're asking four questions. I'm going to list them out. Question number one is, what is the product? Question number two is, how do people use this product? Question number three is, how do they do a version of that same thing in other contexts? And then question number four is, why does that matter to people? Fair. Completely fair. I think people find these analogies familiar. It makes something that might feel complex and unwieldy into something that's actually quite familiar.

15:51And it gives a reason for people to believe why it matters. And I think pulling inspiration from places that are very common and behaviors and conventions that everyone knows is also somewhere where I think a lot of gold is struck as well. But just on the fashion kind of train of thinking, one of the things we launched last fall, which was in conjunction with us updating our product to be the most expressive version of Squarespace ever. And what I mean by that is we built a whole new version of our content management system and our editor, which literally we would argue is now able to make any website you've ever seen or you haven't seen just yet.

16:37Right. So in conjunction with that and keeping the fashion lens on this particular example, what we set out to do to launch this new version of the product is we set out to collaborate with people who are the ultimate tastemakers in the world. people who are known for their expressibility, their creativity, and ultimately their taste. Right. So we ended up collaborating with Bjork, a musical artist who's known for her expressibility, not only in her music, but her fashion sense. And there was an opportunity because she was launching a new album. So there was a tangible problem that she needed to get solved.

17:14So we ended up working with her to recreate the all new Bjork.com using our new version of our fluid engine is what we called it. And not only that, to create all these microsites based off of her music video and flew to Iceland to really get into her head of like, how does she see this blank canvas over here? Like, if you could start from scratch, like, how would you do this? And please tell us like the thinking, like along the way of like, what's going on, like the like in between in that head of hers. And it ended up coming up with something that we would have never have come up with on our own.

17:48It was definitely through her visual style, but the way that she thinks about everything. And it was conceptually tied to her new album. And what we pulled here is that, well, wouldn't it be interesting if we then created a design inspired by what we just created with Bjork and turn that into a signature design in our store, and it would only be there for a limited amount of time. Right. So we did just that. And again, pulling it from fashion, like capsules and drops and what have you, this is something that everyone kind of knows of today. And like the scarcity marketing kind of aspect of that.

18:26Right. So these are all, this is not like a new mechanic or a new convention in the fashion world, in the online web publishing world. I hadn't actually seen that before. and what happened is that we launched this as a signature design in our store not knowing if people would use this would they think is this is too conceptual or like what have you and it ended up being like one of the top 10 designs in our store and i haven't checked the numbers today but it still might actually be up there as it not only converted but to see what people actually did with that design inspired by and co-created by bjork to see what people took that as a starting point And to see what materialized was actually a very beautiful thing.

19:07Yeah, that's really awesome. David, I wonder what you might say to help people take this first step that you've identified. So as a closing thought here, people have listened to us talk about really how to explore beyond the boundaries of the product you have and figure out how it's going to be most engaged and meaningful to people by figuring out the connection points that your product has with other things in the world that people are engaging with. And that's a really useful idea. But as I'm thinking about a takeaway that somebody could have as they're listening to this, I realized that that first step of thinking, well, where do I look?

19:49What adjacent industries? And what am I looking for exactly? Because I could, when the whole world is open, they could do anything, right? I mean, you talk about Bjork, why not talk about the NHL and hot dogs? It's sort of everywhere, right? So what are you doing or what advice do you have for people who want to take that first, let me look outside my own space into something where I can draw a meaningful connection and therefore gain new ideas and inspiration? What's that first step? So I think the, I'll give you a more esoteric response and then I'll give a tangible thing, which is a great exercise for everyone listening in the audience.

20:27But I think in order to find what I call like the unlock, right, of kind of like creative, innovative thinking, it really boils down to this. You have to live an enriched life. You have to experience things out in the world that aren't in your lane. And it's really, really easy to get stuck in your lane and look two inches in front of your face and put the blinders on. And I would argue that you need to live life and you need to be able to pull references. You need, and because ideas are pretty simple. Ideas and all humans are creative beings, right? It's not relegated to a specific department, right?

21:08And ideas are pretty simple. All you're doing is making weird correlations of things you've experienced in your life, right? So it could have been a conversation we're having right here to a song I remember 10 years ago that sparked some sort of nostalgia to a piece of art I saw in a gallery or a scene that I saw in a movie two years ago. And the mind, these are all banked into your head. And one day you'll wake up and your mind will make these weird correlations and there's a new idea, right? So I'm a big believer. You need to have more inputs to have better outputs. That's a great way of thinking about it.

21:45Yeah. And that's all creativity really is, right? And the more you experience, the more inputs you have, which will lead to better outputs. Yeah. I would argue, not to get dystopian, but the elephant in the room with all the large language models and AI and things like that as well, is that I also would argue that creativity might be the only job left in the future. It's true. Right. because if anyone's used ChatGPT to do something creative, like write a poem, it's pretty remarkable that it can do it, but there is something very not human about it. There's something not human about it. It is a remarkable technology, obviously, but you still need the references to actually be able to input in prompt engineering something that's unique.

22:34The other end, you need to be able to reference that writer or that photographer or this director or like a certain, if you don't have those references, right? A lot of it's going to look, a lot of it's going to look the same, right? Because logic is really easy to automate. If you're like things like data analysis, research, and what have you, like machines will be able to do that much better than us to be completely fair. But I would argue imagination, it's really hard to replicate because I think creativity and human and emotional intelligence, those are all uniquely human traits. And I feel like every job that's going to be left in the world, at least like the white collar jobs, are going to have to be creative jobs of some sort.

23:17I want to give you one tangible example for the audience. I want to give the audience an exercise that they can do. It sounds really basic, but it's an unlock for a lot. So if you have a brand or a company and you're kind of stuck trying to find a new way in of telling your brand story, what have you. Here's a very simple exercise that sounds pretty trivial. Some people might find it kind of dumb, but it will unlock a lot. Do the mental exercise of if your company was a car, what car company would it be? What brand of car within that company would it be? Just go through that exercise. If your company was a city, what city would it be?

23:58If you could choose one celebrity persona that just feels like your company, who would that person be? If you were a fashion label, which one would it be? Would it be super high-end luxury? Would it be kind of like low-end? What have you? And you can go on and on and on finding these different parallels. And one day, if you actually put a mood board of all the different things that you've chosen and you pin that up on the wall and you just keep referencing that, you will soon find a truth and you'll soon find a new way in of telling the story of your company and your brand. Because it's so clarifying and it's also allowing you to consider what you are without having to grapple with the context of what you are.

24:45Exactly. Huh. There will be so many different tentacles that will just sprout from this exercise and so many different analogies, metaphors, parallels that you would find. And one of these days, there'll be an idea that sprouts from this and then you run with it. Yeah, I imagine great group conversations, great team conversations about exactly this. Like what a fun thing to debate. Yeah. Well, David, I think that everyone has stopped listening at this point because they're too busy thinking about what celebrity or city they are. I got stuck on city because I love city so much. So thank you for this.

25:22This is really, really enlightening. I appreciate it. And that's our episode. I would love to hear what you think and maybe even about a problem that you solved. You can find me at my website, jasonfeifer.com. J-A-S-O-N-F-E-I-F-E-R.com. Also, I have some more useful stuff for you. I write a newsletter about how to future-proof yourself and become more adaptable and optimistic. I would love for you to sign up. It is at jasonpfeiffer.bulletin.com. Also check out my other podcast. It's called Build for Tomorrow. In each episode, I take on some belief that we have that holds us back from progress and show you why it is not as bad as you think.

26:03Problem Solvers is a production of Entrepreneur Media and comes out every Monday morning. So make sure you're subscribed so you don't miss an episode. Thanks to Deepa Shah for production. My name is Jason Pfeiffer. See you next week.