#286 The Future of Creativity in Tech: AI, Design, and Women's Empowerment with Kelsey Gilbert-Kreiling

0:00:02 - Mehmet
Hello and welcome back to any episode of the City of Show with Mehmet. Today, I'm very pleased joining me from the US, Kelsey. Thank you very much for making the time for this episode today. The way I love to do it and the way I like to do it is to keep my guests introduced themselves. So tell us a little bit more about you and what you do. 

0:00:22 - Kelsey
Perfect. Well, thank you so much for having me. It's such a delight to be here. I'm Kelsey Gilbert Kryling. I'm the co-founder of Week, of the Website, which is a Squarespace first design agency based in the US, in Chicago specifically, and I'm also the author of Squarespace from Sign Up to Launch a book for folks learning to use the Squarespace platform from beginning to end, and also the creator of Better Than Launched advanced Squarespace tools through Superhigh. So I do a lot of agency work and then also do a bit of teaching other folks how to use technology. 

0:01:10 - Mehmet
That's awesome, and I feel very happy when I see people like yourself, who found their niche, let's say, and they're flourishing in it. So maybe it's a traditional question, but what have brought you to this space of web design and why you decided to make the choice with Squarespace, although there's a lot of other platforms in the market? So what made you take this step? 

0:01:40 - Kelsey
Yeah, so I definitely came to it through a bit of a different path. I actually went to school originally for international relations. I had planned to work in the UN and have a life that was in politics but ultimately discovered that I really felt the most fed by making things. So I happened into some sewing classes, some studio art classes and ended up making a pretty radical pivot and finishing my degree in fashion design. So I have a literal degree in sewing and ironing and drawing and while I was doing that I started writing for an online fashion publication as an intern and really liked it. Had always grown up a child of the internet, full millennial, so doing a little bit of HTML and CSS here and there, but eventually created my own online fashion publication and that was where I really got into the space of owning, operating and eventually designing a website. So I did that while I was in school. 

When I graduated I actually went straight into freelancing and contract work in the writing and some design space and then ultimately decided that I wanted to go work at a digital agency for some time to just sort of understand what it would be to work for someone else. From there I moved over to running an online food publication in the hospitality space for a restaurant group here in Chicago and through that process kind of became their like go to technology person, because everyone else just made food right, like they knew restaurant, they knew hospitality, they didn't know anything about technology. So I was the person with the most technical chops on the team and before I knew it they were like hey, we're opening a new restaurant, we need a website for it, can you help? And at that point I had built a couple of my own projects, portfolio etc. And you know it was one of those things where I just took the challenge right, I hopped in and I tell people, the first websites I built for those restaurants because this was what was available at the time was on Tumblr, which is, you know, funny and weird right, like not a, not a platform you would imagine a restaurant website to be on. 

But this was a little bit pre drag and drop builder right. This was, you know, 12, 13 years ago now. And when Squarespace came out, realized hey, this is a great tool to build these restaurant websites on. It can be light, it can be easy to update, they usually have a host, right, whoever's updating the menu for the night is the person who's going to be using the website the most, so kind of fed into building websites on Squarespace. And that was kind of the genesis of my career in the beginning of what eventually grew into this decade old design agency. 

0:04:58 - Mehmet
That's you know. It's an inspiring story, by the way. I love it. So, yeah, like the thing is, you know people when it comes to creating websites, you feel them confused and I believe you know people like yourself can see they are very crucial in guiding them to some extend what I found out that people think it's something easy to do, but actually it's not. So now, especially because you need to talk majority of the time to people who are like non-technical, right? So how do you try to simplify it to them about? It's not just a website that you created in a box, in a click, let's say it's out of the box, it's out there. So how do you approach and I'm very curious to know how you approach your discussions with individuals and businesses with a little bit tech background about how they should have a beautiful website? 

0:06:06 - Kelsey
Yeah, I think you really hit the nail on the head, because I think you have like two really different sides of it. Either there's people who think that having a website is like very simple click of a box or so impossible that they could never never do it themselves, right. There's the people that are like I could never do that myself, this is so hard, I don't know how to code. And then there's people, on the other hand, that are like why would I pay you? Making a website is easy, and the reality is that it's really, depending on the client, much more a spectrum between very easy or completely impossible, and I think one of the things that Week of the Website has like really honed in on. Our company is very focused on doing work for clients that exceeds what they would be able to do for themselves, while also building websites that they can then edit and use once we're done with them. Because I think what people find is that it's either or it's either a website that is very beautiful, very designed forward, has a lot of these advanced features and doesn't feel like it was built on a tool like Squarespace or Wix, but they can't edit and use it, or it looks very DIY right and we have found a sweet spot in building websites for folks in a way that is really quite welcoming. 

I think, like the, I always tell everyone, like the goal is not to use jargon, the goal is not to make people feel like we know more than them. If someone comes to me and says like, okay, kelsey, when I go to my website, I want to see a spinny thing with my logo, and then I want that to go away and I want you to see the homepage. Like it doesn't matter that the client knows that that's called a load screen, with, you know, with animation, that will be run by. You know CSS, whatever, like they don't care and they don't need to know that, as long as we know what a spinny thing is and we can implement it. That's our job is to make the client feel comfortable, heard and understood, and I really spent a lot of time coaching my team that we know more. 

We have built, like by many, many metrics, more websites than our clients ever will in their lifetime. Because it's our job and not theirs. So it's our responsibility to make it feel very tangible and understandable for them, because when people understand things they're more likely to engage in them and really, when you're building a website for someone, you have to. It has to be something they feel a sense of ownership of, because otherwise they won't use it and then it's useless. Right Like? 

My team has probably gotten very annoyed hearing me tell people that we build websites that act as toolboxes for your business. We're not in the business of building billboards that you have to hire someone to climb up and change, and I think that's really important to us. There are people who build highly custom sites that require a dev team to maintain and those are a fit for really specific businesses, but the client that we serve are people who are still, you know, like under a thousand employees and you know they may not have a dedicated digital team and they're really relying on their website to be something they can use at it and own. 

0:09:26 - Mehmet
You know, whenever I hear things like this, because you know I work as a consultant for a long time in my career and you know being on the customer side and you know putting yourself in their own shoes right, as we say, it's something very important. 

And you know, and I know, how hard it is because when you know how it's done but you know the client might not know and then you need to take a step back and say okay, as you said, because, for example, you build websites and of course, you and the team you have built thousands of websites and for the client it's just that website or maybe they shift business later on. 

But one of the things which I think, Kelsey, is underrated when it comes to websites and you touched a little bit on it is it's not about only like the fact that it is a website, but I believe you know the design and you know the how much you are willing to put into the design, and here we are talking, of course, about web design. It's very important and I know even in your book you emphasized on the empowerment through web design. So I want you to give us, you know first why you know this design element is very important into a website. It's not just about the functionality or you know the, as you mentioned. You know what is. Maybe it's a JavaScript, it's a CSS, whatever it is, we don't care as long as people right, but why the design is important and you know if you can even share a story about how your guidance helped someone approach or perspective to web design. 

0:11:06 - Kelsey
I think that it's. It's so simple to be pulled immediately into the mechanics of how a website works right, and design is the storytelling. Now there are clients that are going to be very, very focused on how the website is built right. Their clients that are going to be really focused on, well, you know, is is X feature going to drive Y conversion, and I think that for those clients, the more information that they have available to them, the better choices that they're going to be able to make. But when it comes to design, I think folks forget that the internet is still a very visual place. Right, it's still a a really emotion driven environment, whether we want to believe that or not. And design is the way that we convey technology to people. It's hard to look at a page of text and really gather what's going to be important from that text. Right, we use design to create hierarchy. We use design to direct attention, and for many small to medium sized businesses and organizations, it's crucial that they use design to help people understand what they need to know. 

I am fond of asking people in every call strip it all back like take away what you want the page to look like, what you want it to say when your client comes to your homepage, they sit in front of it, they see what's right above the fold. What do you want them to do next? And that's the question that everyone should be asking themselves when they prepare to build a website. Everyone, everyone should be asking their clients when they build a site for them what action do you want them to take? Because websites are not pictures, they're not movies. They're, you know, they're things that we have built to inspire action. So we have a client that we're working with right now who's a really renowned speaker and therapist and she and her team have, like all of these features that they're interested in, right Animation and movement and flow, and those all contribute to the overall feeling that they want her website to convey. 

But we had to just stop the call the other day and say, like, all of that is good and there's a place for that, but our first interest from a design perspective is not, you know, bells and whistles and animation and movement. The first question is what do you want the client to do and our you know the viewer to do, and our job as designers is to focus their attention and energy towards taking that step. That's important for the website to inspire and I think that it's easy to say, oh, design is just pretty colors and features. It's, it's an entire mindset and system that helps direct people to where you want to go through visual language. So for me, that's like the interest and the reason why design is important outside of the mere, you know, technical infrastructure, that that provides the opportunity for us to do that. 

0:14:42 - Mehmet
Absolutely, I agree with you. And I remember, you know, I had the chance to help someone. That was, I think, 2009 or 2008. Very long time ago when, still, you know, the web design was kind of not a new thing, but I mean, everyone was rushing to have their own website and we used to get these, you know, requests I want my website to be exact copy of this website. And I remember that guy, he he told me this. He was asking, wait one second, why you need your website to look exactly like that website. Are you trying to imitate or like, copy their design? Are you trying to copy their functionalities? Like, are you trying to copy their identity? What exactly you like about that website? 

And then you know I learned from there that there are a lot of things, as you mentioned. You know it's like not only the look and feel, the look and feel, it's also, you know, the. I believe there is a spirit when the design is in a web design as well. I'm a big fan although, like, I'm not a designer about any means, but I'm a big fan of user experience. Yes, and, and you know, when I go to a website, how they let me feel, yes, regardless of, regardless of the action, but I like to always ask the expert case. Yeah, this is why, you know, I asked you this question about design and you, you, just you know you also like hit it. 

you know, as, as we say, and I liked you know your approach of taking each use case separate than the other ones. Now, but some people would would counter you know this, will say, okay, but this is why there are templates and this is why you know we can reuse these templates and customize it the way we want. So, back to to to think very important, and this is why I'm maybe I'm asking, I'm repeating myself a lot, but I want you, from your perspective, to tell us how storytelling plays a role in the look and feel of a website. 

0:16:48 - Kelsey
It's everything. It's everything and you know I think you make a really good point like templates, especially in the world of website builder tools or kind of this like no code expression of you know, design and technology as they merge, design and engineering as they merge templates are always going to be a part of any digital work, I think in the future. Because why do what you've already like? Why? Why like? Why work harder when you can work smarter? And I think those serve a really important place. They have a really important place for people who are learning technology, who are learning how to use Squarespace, webflow, wix, wordpress, any of these tools. But when you bring that to storytelling, you're always going to be limited in telling your story with an existing template, because the template makers that I know like they have an intention in their mind when they design them right. They're building for a community, they're building for a specific type of client who's going to be a best fit for that, for that product. But if you merely add your information to the template, you are telling your story in. You know your words right, your headline, your text, your images, but ultimately it's always going to feel like you're putting your story into someone else's framework and I think for people's first websites that makes sense, because when you start your business, when you start your new project, let's be real like very few people end up doing the thing that they set out to do when they started their business. There's always shifts, there's always changes. So I'm actually not a proponent of people spending a ton of time and money on their first websites, because at that point you should be in an experimentation and flux state, like when we started our company. We were building websites in a completely different way than we do now and we were producing like large scale events and gallows and fundraisers, and ultimately, what we ended up doing is taking our project management skills and abilities from the event space and bringing them to our web design engagements, where we were able to like get clients to turn in content on time and get them to provide us with the materials that we needed so we could work with them over seven days to build an amazing website, get it launched in live and out the door. But when we started our company, not only did we A have a different name and B have a different approach, but it was different. You know, the website that I had 10 years ago is not the website that we have today, and, in fact, we're about to launch a new website this year that reflects our positioning better now. 

So I think every good business every year should be evaluating their positioning, evaluating their story and then bringing their digital home in line with the story that they are looking to tell. And, ideally, as a business, you've established your core values. You've established the things that you're passionate about and you care about. That inform the work that you do. But technology moves fast. 

If you are in a tech-driven space, the story of your business is going to change every year, and so I think if you're starting out using a template, it's fine. 

It's a great low-cost, low-stress way to get started. But as you deepen your experience with your business, as you grow into your company and as your story becomes more codified, then I think it's important to be making the investment in telling that story very clearly so that when people come to your site they don't say, oh, this is a pretty site. They say, oh, I know everything I need to know about Week of the Website, to invest in time and in finances with them to build the next iteration of my website, because the story is very clear. So I know I'm probably speaking in a way that would potentially take business out of my pocket, but I really think that you have to know what that story is before you invest. So I think templates are never a threat to custom design work. If anything, I think it helps people have better clarity around what they want and who they need to hire to help make that story come to life. 

0:21:14 - Mehmet
And just to add to what you just said, kelsey, and I hope more people will start to believe in the expertise of other people, so you can find the template right, but if you don't use it in the proper way and you don't translate, again back to the story, point to what really reflects the values of your business, to what you're trying, to, the message you're trying to convey, and I think this is why businesses will always require such services from companies like yours, and I discussed this with one guest like I think, a couple of months is back. People think, like the website is a one-time task and then they can go and they can sleep right. So unfortunately it's not, and this is why, unfortunately, many people now and I start even hearing from non-techy people all this website it looks like very 90s style or like even early 2000s style, because yeah, I said yeah, they didn't even put the effort to forget updating the content, even the look and feel. It really looks very, very old and this is why I don't think, kelsey, like agencies, like what you have done, they actually you will have more work, and this is why I will relate it to the next question. 

Now, in the age of AI, which everyone talks about, and now we can generate websites with AI and all this. My point of view, we still need an expert AI like yours, kelsey, but I like to hear it from your side what do you think gonna happen with all this doom and gloom of the AI doing everything from web design to PowerPoint to pitch text, to everything? Yeah, so what are you seeing and what you are expecting to happen down the road? 

0:23:13 - Kelsey
Yeah, I don't really feel the fear aside from the like dystopian universe, far reaches of AI theorizing, I don't feel an existential threat towards people-based businesses, and I say that because we are very much a people-driven company. Right, like, we have websites built by people, managed by project managers, and the reason why we have project managers is because clients typically do not just like get a to-do list, do it, meet those deadlines, get it in on time and never need feedback from us again. Right, they have questions what kind of materials do you need for this? How long should this be? What is, you know, like? There's a lot of those very human questions that are a part of our process, and so when I hear, oh, there's a new AI website generator, I think great, like, if that can help someone go from having zero website to one website, that is great for them. But that's different than what we do. In the same way that you know, templates don't necessarily pose a threat to us as a company because we do something different. I think you're right. 

People forget that websites are not a one and done. It's more like buying a house. You know, you go through the process of buying a home and it feels very challenging. And then you get in the house and you're like, oh, my drain's clogged. Oh, I guess I have to fix that Right. Or I want to change the emotion of this room oh, I'm going to change the decor, I'm going to do a renovation. There's a different scale of how much you can evolve and change websites. So, yes, it is a continually changing thing For me. 

I think AI can be incredibly valuable in helping people get unstuck, right. Squarespace has rolled out its first generative text tool and I find it a delightful alternative to Laura Mipsum. Right. Instead of plugging in, like I have a Chrome extension where I can tell it, like I need three paragraphs of Laura Mipsum or one sentence of Laura Mipsum and it's automatically copied and I can paste it. Now, instead of doing that, I can go in and if we're working on a client's website and there are a nonprofit that serves communities in Chicago, I can say give me three sentences on a fundraising event that will take place in Chicago in February and it can generate something that's contextual and it can help that client get unstuck when they think about writing the copy for that page. I think that's great. 

We on our team have a absolute continuing chuckle at AI images that are provided to us from clients. Anytime they have hands and feet in them, because they come out very weird, and it's one of those things where we're just like check out this picture. The feet are so strange and I get why the clients use them. We try to guide them and give them some better boundaries around. Hey, if you're going to use generative images, they should be more like x, y and z. And also here are some alternatives that are stock photography that you can pay for. That's not that expensive. 

So I think of it as a tool, and I've said this on many occasions. In the same way that the invention of the microwave did not necessarily change the world for chefs in a way that limits or hinders their work, it becomes another tool in their toolbox. And I think, for any digital creator, ignoring AI is not going to serve you, but relying on it entirely is also not going to build you the tools that you need to be. More than that, you can't take away 10 years of conversation with clients, of memory, of experience, and I think that's what people who are service providers really do is they bring that memory, they bring that experience, they bring all of their years of thinking about problems and unique ways to each of their client engagements, and that's just not something that can be replaced by AI at this stage. Now, in 10 years, you're welcome to come back and ask me the same question and we'll see how right I am. But that's kind of my interpretation of where we stand so far. 

0:27:48 - Mehmet
To the point of the AI-generated images where you have hands and feet. I remember all the means that they were appearing when stable diffusion started really to become mainstream for a lot of people, especially on Twitter or X, and it was really ridiculous. And I know one guy that he spent I don't know how much time he spent to just make sure that whenever he's generating a hand it's actually have five fingers, not seven or eight. So, yeah, yeah. 

0:28:23 - Kelsey
Make an image of a person with five human fingers. They must not be too long or too short. For the love of God, please make the hands look normal. That's like 80% of your prompt. 

0:28:33 - Mehmet
Yeah, but, to give credit, I think the best of all the tools that I have tried is stable diffusion. Dali is a catastrophe sometimes, especially when it comes to humans. I even tried on myself. So, for example, I uploaded my photo and said, hey, show me in a cartoon style. And then it put mustaches and bear and I said, ok, no, I don't want this. And then I spent maybe half an hour just to tell exactly how I want to look like. Yeah, you cannot rely 100%, and I think art is one of the things that AI can help us produce, but it will not replace us doing it like, if I can pick it in this way. 

0:29:17 - Kelsey
Yeah, I have a funny anecdote for that. I have a two-year-old and he is really just becoming conscious of the world in general and my husband is a software engineer. He went through a build-in public cohort with a gentleman who built a tool called Kid Genie, and Kid Genie is a generative art tool to help parents translate the things that their kids want to see. So my son, who doesn't watch Spider-Man like I don't really understand how it's become a part of his world but he was like I want to see Spider-Man skating, dada, show me Spider-Man skating. And he kept trying to generate different Spider-Man skateboarding no, not skateboarding. Rollerblading no, not rollerblading. And ultimately he got to the point where he was able to tell my husband he wanted big Spider-Man and baby Spider-Man ice skating together. 

So my husband went through a couple iterations and then he landed on this image that my son was like yes, that's it. Like he was able to take his baby brain, imagination and turn it into this picture. So for Christmas I had a local company print that image on a sweatshirt and a shirt for my son, and I think this is a really great way that we can see how that technology can be kind of magical and can use this really special way of interpreting our imaginations. And then I used a small local company to print it, and it'll never go further than us, right, but it became something that drew our family closer, and so I think AI, when it is combined with the human, can be really special. It's not a replacement for it. We will still, ultimately, I'm sure, buy Spider-Man merchandise, but that didn't exist, because there's never been a movie where daddy Spider-Man skates with baby Spider-Man in the city. 

0:31:21 - Mehmet
Yeah, I've seen something. One friend told me something very similar the other day and yeah, but this generation you cannot expect from them. They are able to learn about things, so you would be shocked. Even two years, one year old kids talking about this. 

Yeah, so we're living in a different world. Indeed, can't see one thing which I don't want to miss without asking you this question. Well, let's say it's not a direct question, but I'm a little bit inspired and biased by successful people like yourself and, let's be honest, the domain is really male-dominated, right. So I want to tell us a few things that can aspire to have more women in tech, especially in this domain, because I feel we are in 2024 now and still people say, yeah, it's a man's job, right? Especially when we talk about tech, which I don't believe really there is a difference. 

I know like we crossed very good amount of you know all these things that no women cannot do, that they should be doing this, they should be doing that, let them do the fashion, design and all this stuff, what they are doing in tech and all this. So it's good like we crossed this, but we still don't see enough women in tech. And this is something, by the way, global. I know like even in the US you talk about it here Good, we have some progress here in the place where I'm living, in Dubai, so we see more women in tech actually working, whether in the heart tech or even I'm fine with consultancy, even as well, but because you know you've done it as a mother, as an author and as a agency like co-partner, so leave us with more that can aspire more women to be in tech. 

0:33:28 - Kelsey
Yeah, I mean I feel lucky to be born in the time that I have been born right, because even 10, 20 years earlier it may not have had this outcome. It's hard. I think you know only 2.6% of funding in the tech investment space went to women run startups last year in the US, and that's a really low number. Right, there are a ton of women who are deeply innovative and I think we are getting closer and every day there are more and more people who are getting involved in technology from non-traditional backgrounds. And you know, I think my best advice is to put your head down and keep going right, like. It is hard. It is a challenge to build something lasting and I think it's very important not to be distracted by people who tell you it's easy, because they probably have a vested interest in telling you that it's easy or making it seem like they're making vast sums of money in their sleep. Those people, even if those are accurate, they're outliers Most people like myself, who are growing organically funded businesses. We've never taken investment. It's a challenge, but I think it's worth doing because 10 years on, you own your life right, like if you're a woman, I would say. Finding a business partner can be really amazing. It's not for everybody, but I've been very, very lucky to partner with someone who is a great balance and foil to me and we definitely work through things together and I think having that partnership can be really great. I will also say I've never found much fire in losing sleep over the ways that people have been dismissive of or hurtful based on my gender, whether it was intentional or not. 

I find a lot of fuel and fire in the successes that come that people aren't expecting. We just completed a really significant project for a US-based nonprofit organization called YWCA. We brought their dot org to Squarespace Enterprise in partnership team and we're in the process of bringing 60 of their local associations from WordPress to Squarespace so that they all can use, manage and own their websites. And when we tell people that they're shocked, they can't believe it and that is to me it's a compliment because it means that we are defying expectations of what a design agency run by women focused on a user-friendly tool Squarespace can do. 

But I think that that comes from surprising people and it's worth it. I think finding good mentors and good partners is vital and, yeah, I continue to hope to see more and more women in technology, and I think this next Gen Z generation is going to blow us all away with the equity and density of minority and women-led businesses, but also, hopefully, businesses that find balance right, that have all kinds of people working there, because that's how you create a really strong business and a really strong community. We have a great team of people who, many of them, are women, some of them are not, but a lot of different people bring a lot of different power to our company, so can't wait to see more of that in the world. 

0:37:50 - Mehmet
What a nice message from you, kelsey, and I hope more women will be hearing to this episode, especially this encouraging one. You mentioned something a few moments ago about your husband and the cohort and all these things. This is one of the ways because I was part of a cohort just for fun, not because I need to learn anything and what I found it's one of the also good way for anyone, and especially for people who could be a little bit shy or could be hesitating, so you could start with a cohort. Actually, it's a good idea to learn about technology and there are plenty of names. I can name some, but some of them they will not forgive me because I forget about them. There's plenty of them. I had the chance to work directly with them. They are very well known all over the world, so it's a good place to work. 

I get to know people from all around the world and many of them even they became first-time female founders, which is great. And we were talking about AI a few minutes ago. And yeah, by the way, ai is your friend. Whoever you are, whatever you are, whatever you are ready to do something. So this, as you said, like you just mentioned, a very good point. It's Toolbox, it's another tool in the Toolbox, so leverage that. Kelsey, just find a thing where people can find more about you and your agency. 

0:39:17 - Kelsey
Yes. So you can find our agency at weekofthewbsitecom and we've got lots of information about how we can collaborate and help you with, we say, your second website right Once. You know that story a little bit more. We do, we kind of focus our work. We work in three different areas. So we do individual projects, we partner with other design agencies to be their integration partner for web design services and we also provide enterprise design services to select companies. So that's week of the website and if you'd like to learn a little bit more about my book, you can go to buykelseygkcom and there's lots of fun information there. 

0:39:59 - Mehmet
Great. I'll make sure all the links you mentioned are in the show notes of this episode. And Kelsey, I really enjoyed the conversation with you today. Thank you very much for your time and for the information you shared with us. So for the audience, go to the show notes and find all the information about Kelsey and her book and her agency, and this is the way I usually end my episode. So for the audience, if you are a first time listener here or first time you're watching us, thank you for passing by. I hope you enjoyed it. Please subscribe and tell your friends and colleagues about our podcast. And if you are one of the loyal fans who keeps sending me their feedback and suggestions, thank you very much for always being on my side and sending me all your compliments and even please send some feedbacks as well. I'd love to hear your feedback how we can make things much better as well. So thank you for being with this journey with me and we will see you again very soon in any new episode. Thank you, bye.