How I Built This with Guy Raz - Advice Line with Anthony Casalena of Squarespace

Episode Date: November 20, 2025

Squarespace founder Anthony Casalena joins Guy on the Advice Line, where they answer questions from three early-stage entrepreneurs. Plus, Anthony shares how Squarespace is leveraging AI to help people bolster their sites and digital presence more effectively.First we meet Bob in Connecticut, who’s wondering how to pump up awareness for his custom-made mattresses. Then Stacy in California asks how her new first aid products can stand out in a category dominated by legacy brands. And Mehek in New York strategizes about how to best launch a new digital companion she’s building: an app that supports people recovering from eating disorders.Thank you to the founders of Custom Sleep Technology, All Better Co., and Kahani for being a part of our show.If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [e-mail] or call 1-800-433-1298.And be sure to listen to Squarespace’s founding story as told by Anthony on the show in 2019.This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was James Willetts.You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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It had tall windows, beautiful old details, and plenty of space for all of us. And being in that home on Airbnb, right in the middle of Vienna, walking distance from so much of the city, made it feel less like a visit and more like we were actually living there. Plus, taking a trip is the perfect time to host your space on Airbnb. your place with all of its personal touches and its amazing location could make someone else's vacation even better your home might be worth more than you think find out how much at arbb.ca slash host hello and welcome to the advice line on how i built this lab i'm guy ross this is the place where we help try to solve your business challenges each week i'm joined by a legendary founder

a former guest on this show who will help me try to help you and And if you're building something and you need advice, give us a call and you just might be the next guest on the show. Our number is 1-800-433-1298. Leave us a one-minute message that tells us about your business and the issues or questions that you like help with. All right, let's get to it. Joining me this week is Anthony Casalena, the founder and CEO of Squarespace. Anthony, welcome back to the show. Pleasure to be here.

It's great to have you on. You were first on the show back in 2019. You told us a course about Squarespace's origin story and all the things that you learned growing Squarespace. You found it in 2003 as a 21-year-old kid as a college student. I remember some of the stories about racing up and down I-95 and changing physically, changing the servers out and all this craziness. But basically it started because you had a frustration. There wasn't anything really to build websites that was easy and good. and you basically built the software for yourself.

And then a friend saw it and said, I'd pay you 200 bucks to use it. And that's kind of how it was born. Yep, that's right. It's an absolutely amazing story. And of course, we'll put a link to that original interview in the podcast notes in the show description. So please check it out. It's just an awesome story. Since you were on, Anthony, you've taken the company public.

It then hit over a billion dollars in revenue. And then last year, it was bought up by a private equity group. Yeah, we took it private. Yep. Amazing. So private again. And all this time, you stayed on as CEO and chair. And, you know, just out of curiosity, by the way, how has it – I mean, you're a founder, right?

You built this thing. You took it public. Now it's private again. But I guess you kind of have bosses, right? I guess shareholders are your bosses. but now you've got bosses again. Is that make things more complicated? Does it really not change things a whole lot for you?

No, I mean, running a company, you always have a boss, be it even if you owned 100% of it yourself, your customers would be your boss. And so nothing has really changed for me or the company in a day-to-day. I mean, we could have remained public. We thought it was a little better to do the private move, but we were fine to do either one. So, no, my day-to-day is pretty much the same.

Tell me a little bit about how you think about expanding the business. You are, just full disclosure, it doesn't matter because it's a great story. I even don't even know this, but you guys advertise on how I built this. Yes. And, you know, you offer, it's not just, you know, start out building websites, but now it's like your full, full package e-commerce site. You offer tools for small businesses to basically run their business online. Yeah, we offer a complete set of tools for entrepreneurs. and small businesses and others to get online.

I mean, what started with a publishing product centered around websites and blogs that evolved into portfolios and more now encompasses great e-commerce tools, not just for physical sellers, but people selling services. We have other companies under our umbrella, like Acuity, which helps people sell time at the scheduling product. we acquired the assets from Google domains. And so we're one of the, by brand, probably the third biggest domain registrar out there. We're one of the biggest website builders. One of the biggest resellers of business email through Google Workspace.

And so we play in a lot of different lanes that help people get online. And I think it's actually a funny thing. And maybe there'll be some AI questions at some point. But, you know, what we do is more relevant. live in than ever, because this is how normal people participate in the web and SEO and what we call AIO, which is optimizing for answer engines, is how people get found still. And so we continue to do very well. And it's just kind of a pleasure to be servicing millions of entrepreneurs.

Yeah. I mean, in this era of very fast-changing era of technology around AI, right, and now more and more people are using chatbots to do search, right, that they might have gone on Google before. and now they're going on chat or perplexity or whatever. How does that change what it means to have a website, right? Like you're a business. Your website is your storefront. How do you stay relevant when that's how people find out about you more and more? Well, that's one way people find out about you.

And I think that the website ends up being more relevant than ever for a number of reasons. One being it's where the answer engines are finding their information. You know, they're crawling the web. using either old data or modern data or more relevant data to give you the answers they give you. And when they don't have the answer to a real-time question, they go to the web. And so it's being used in both their index, and it's also being used for real-time interactions. And then, you know, most of the interactions with a small business being contacting them, submitting a contact form, booking an appointment, purchasing a product.

That's still happening with some kind of direct interaction with that customer. and we facilitate that interaction, whether you started on a search engine or an answer engine or a social network or anywhere else. And so we're really happy to be positioned as we are in this era. I know you've got AI tools already to help basically build out websites, designs, and it's having very, very fast, right? I mean, what may be available in a year from now, like you may not even be able to fully anticipate that, right? What does it mean for your business and how it sort of fits into that into this sort of brave new world of AI tools? Yeah, I mean, it's been a phenomenal tailwind for us. I mean, we're not particularly worried about the, you know, the idea that people could code a website where they couldn't code a website before because people haven't had to code websites for two decades using Squarespace.

But, you know, we have AI and what used to be called machine learning, frankly, enabled into every aspect. of our product. And in fact, our Blueprint AI product, which is the primary way you would get started with Scorespace if you just click Get Started was named one of Times 100 best inventions of the year just last week. So we've got it everywhere.

And from optimizing your site for SEO and AIO to helping you generate imagery that works for you, you know, we've got AI enabled and probably 15, 20 plus touch points in the product right now. Wow, it's awesome. It's an awesome story. Again, I highly recommend you guys take a listen to Anthony's story and the Squarespace story because it is really, really cool and crazy story. Anthony, you ready to take on our first caller?

I sure am. Let's do it. All right, let's go. Welcome to the advice line. You're on with the founder of Squarespace, Anthony Casalena. Please tell us your name, where you're calling from, and a little bit about your business. Hi, hi, Guy. Hi, Anthony.

Hi. My name is Bob Zikowski. I'm calling from Newtown, Connecticut. and I'm the founder and CEO of Custom Sleep Technology Incorporated. CST is a technology company that combines artificial intelligence with our own proprietary software to design and build a mattress that is specific to each sleeper's unique body characteristics. Wow. Well, okay. Thanks for calling it. All right. So you, so these are custom mattresses. This is not off-the-shelf mattress that you just like add a pad or two. Somebody, what you like, it's like going to a tailor, you measure somebody and then they, then you take all that data and you build a mattress with that in mind from the ground up? Yes. So on our website, we have a questionnaire. We call it a body profile questionnaire. And once that's complete, that gives us the information about the physical characteristics of the sleepers.

and from there, AI mathematically designs the mattress, and our software delivers those designs instantly to the potential customer, and then it's followed up with an email with a complete proposal. Wow. Okay. So you enter, you input the information, your height, your weight, and different things, and then you get a proposal for a mattress. And how much roughly are the mattresses cost?

So Queens are, you know, in the 3,800 range. Kings are in the 4,500 range. Got it. And are they, I mean, is the material any different from other mat? I mean, is it latex? Is it foam? Is it, what's in there? Well, we use exclusively tallole latex.

Because it comes in multiple densities, we can utilize the different densities to support the shoulders and hips separately. So our goal is really to take pressure off. the various pressure points, align the spine, and when you do that, you get the body in the right position, then the sleeper has the greatest opportunity of achieving high-quality REM and slow-wave sleep. How did you get into this? This is a very complicated business. We've done Temporetic on the show. We've done some other mattress brands like Casper. And I, it's not, this is not easy. So how did, were you in this business before?

Well, I used to work for the company that manufactures the latex. And my job was to work with the major mattress brands to incorporate Tallulay into their products. And I came to believe that their number one priority was not how their customers slept, but that their master's wouldn't fail in the field. And then I started doing my own research, pressure mapping, my friends and family. family. And I learned that weight distribution is completely different depending on your physical characteristics, your sleeping position, your height. And I realized using the eight different densities of latex that I could build a mattress that is personal to the individual sleepers. All right, quick question. And I want to bring Anthony in. Can you make a mattress that works for

two people? Like, because, you know, I share a bed with my wife. So, And if we have different measurements, can you do that in one mattress? Oh, absolutely. That is one of the things that separates us from the rest of the industry primarily, is that your design is for you and your wife's design is for her. Got it. Okay. And what's your question for us today?

Well, my question is we're not well suited for the traditional big box retail channels. So I'd like to get your thoughts on taking a different approach. should we consider partnerships or license agreements with wellness tech companies or fitness organizations or even professional athletes to grow consumer awareness for the brand? Anthony, this is like one guy in Connecticut starting a mattress brand that's innovative and interesting and I just, I love it. I'm cheering you on even before I know all the details. Okay, I want to bring you in. Okay, well, I'm on the website.

and I'm a website person, so I'm just going to go out and say that the site. It looks a little dated. But I think maybe the licensing, unless you have an interest in it yourself in kind of getting out there, branding this, not making, flashy is the wrong word, but you got to make me like, oh, wow.

Like this is, I don't know, like you got to kind of catch me with the branding or something. Yeah, I agree. I think, I mean, listen, and by the way, if it's Anthony buying a matter, mattress here, Bob. We're talking about the, we're talking about the Swedish,

that one that's like, you know, a hundred thousand dollar mattress. That's what he's buying. That's what he's doing. He's getting that like by the tiny little elves and, you know, some,

some Nordic town making them by hand. Yeah, but I'm going to say, I'm going to say this, though. I am a little, thanks for pigeonholing me there. But like, I am a little,

I am a little skeptical, though, when the materials are like, and it's horsehair and this and the horses are from here. I'm like, why does that make a better mattress? I'm kind of unaware of why that should be true.

So I am susceptible to what I would call more of a scientific message than a like rich materials message. So I think there's a world fee for people there who don't want to necessarily pay more because the mattress, and I would consider myself part of this and I'm very into the branding.

But I don't need it to be made of gold fibers. I think that would probably be very bad. actually, because that doesn't make a mattress better. I don't think. You tell me. But if you knew, right, like we know, I know that Bob, who's been in this business for decades, knows how to do this. Yeah.

But, and you're right. Listen, and Bob, again, this is tough. It's tough. I know you don't have time, but, you know, maybe you should go on Squarespace and redo your website, okay? It's easy. Maybe get the AI agent. I said I was going to be blunt.

I think we need a little web help. You need some web help. I can appreciate that. Thank you. And you can do because I need to go here and be like, you know what, I am going to spend three grand on this thing. Yeah, yeah. I trust this guy because, see, I can talk to you here and say that. But your website, and not anyone's going to talk to you.

Your website's what's talking to people and how you. And so you need to, you know, you need to basically make it so people can say, yeah, I'll do that. The other thing in terms of like licensing or working with, you know, some interesting brands, I think that could be a cool idea, especially if you can somehow. integrate some of the technology, you know, there's obviously there's eight sleep that measures your sleep. And could you put an eight sleep on top of this mattresses? Could it be designed? Could you work with aura rings, you know, or whoop, which we've done on the show? I think that's an interesting thing to explore because, look, you're a small brand. You're looking to compete with there's temperatech and dial a mattress and all these things. But you're offering something

very, very different, very custom, very specific. And it can be scaled. We know what happens. People scale these things. But, you know, you're, and so it may make sense to try and reach out to some of these brands and say, look, this who I am, this is what I've been doing. I know this business. And I know it really well. And I've got a really terrific killer product. We just don't have the scale to get this out there. And we need, you know, we want to work with a partner. And maybe that's the angle for the licensing that some of these brands are going to say, look, here's our off-the-shelf stuff. It's not customized for you. But if you want something custom and they'll mark it up maybe to three times what you're pricing it out, you know, you could be the technology behind that.

But you're under that brand umbrella. You can kind of deliver the technology to people, help them out without having to go from zero and build a brand, you know, build a brand from zero. Yeah. And I've got information about you, Bob, stuff you've told me. And I know that you can do thousands of configurations. It sounds like, you know, different densities. And you mentioned this latex. What was latex that you use again?

Tal-Ale-I. I don't know what that means. I know that latex is a really good thing for mattresses unless you have a latex allergy. But Tal-A-lay, what does that mean? And you need to somehow convey that on the – starting with the website because that's going to explain the whole brand to people, right? It's like personalized sleep system. Well, eight sleep says that. And, you know, Tempetic says that other people say that.

But you're saying something different. It's like we make a mattress for you specifically. And that's different. That's a different value prop here. Right. And we can modify it over time. So we build it to your existing body profile, and then we can change it over time. Tell us that from the get-go, right, Anthony?

Anthony is going to be your personal customer service agent. Just call him up. He's going to walk you through the process. I gain 100 pounds, I call you. I lose 100 pounds, I call you. We just keep adjusting. That's right. That's how we do it.

That's awesome. All right. The company's called Custom Sleep Technology, Robert Zikowski. Thanks so much for calling you. Good luck. Thank you. Thank you both for your time. Thank you.

Good luck. Yeah. So you're sleeping on horsehair now, Anthony. No, no, no. I'm not susceptible to these. To these one. I said the opposite. I said, I said I'm not sure those make better mattresses.

I think that there's certain places where the branding takes you that don't really translate into anything that's better for sleeping. And so I'm kind of, I'm allergic to that stuff a little bit. All right. We're going to take a quick. break, but we'll be right back with another caller and another round of advice. Stay with us. I'm Guy Raz, and you're listening to the advice line right here on how I built this lab. Welcome back to the advice line on how I built this lab. I'm Guy Raz. And my guest today is Anthony Casalena. He is the founder and CEO of Squarespace. We're taking your calls. So let's bring in our next caller. Tell us your name, where you're calling from and just a little bit about your business. Hi, guy, hi, Anthony. I'm Stacey Bernstein, and I'm calling in from Los Angeles, California. And I am co-founder of All Better Co.

And we are reimagining Mom's First Aid Kit with Better for You, Better for the Planet, daily skin health essentials. Awesome. Thanks for calling in. Welcome to the show. Thank you. So All Better Co. You sell First Aid kits, so like Band-Aids and, I don't know, like Basset Tracin and stuff like that. Yeah, that's the goal, ultimately is.

for us to create these one-to-one products. Like for right now, we have our Don't Scratch That Pen, which is an award-winning our proprietary formula, which is a replacement for hydrochortisone, right? So anti-Itch, anti-inflammatory. The same way you'd use hydrochortisone, we don't want you to do that. We want to use our product instead.

Nice. And where are they being sold right now, mainly? So we're D-to-C, Amazon, and we're in about 100-plus retail locations across the country, including Air One, a few resorts, and we're really kind of actually testing these channels and see where we live best. Tell me how the idea came about. Yeah, so I come from brand.

I have brand background and creating immersive experiences for families, and I've always really spoken to families. And during COVID, my co-founder called me one day. My daughter suffered from major, major mosquito bite reactions. And it got so bad, the only thing that was working for her were prescribed steroids. And that's just not intended for everyday use. And my co-founder has kids that deal with eczema and sensitive skin as well. So we were kind of like on the same page. And we kind of joke that, you know, we solve the world's problems in the parking lot as moms do.

And we decided when we couldn't find what we were looking for for our children, we would make it ourselves. Tell me a little bit about how you guys are doing so far. I mean, what are your, give me a sense of your sales. Yeah, so again, since we came out pretty strong out of the gates D2C and as a bootstrap company, just really being scrappy, a lot of organic seating, getting our product into as many people's hands as possible, and really just gaining some brand equity. And then when we kind of knew what that was like and we decided to try retail and so we went out, just the two of us, actually you're looking at our sales team right here,

and just started knocking on some doors through email. And when we went into retail, we took a little bit of a hit on our margins, right? Because once you're in retail, there's a little bit of a dip. But so far, we're about 200,000 lifetime sales. Amazing. And before I forget, tell us what your question is. Sure, absolutely. So, as I said, we're a bootstrap female founded brand,

and we are bringing clean beauty standards to the first eight aisle. It's not the sexiest category out there. And most people don't even realize what they're using. could be doing more harm than good. Plus, we're up against legacy brands like Neosporan and Band-Aid. So how do you get consumers to rethink something that's been in their cabinets forever to buy it before they need it and to understand why our products are better? All right. Awesome.

I want to bring you in, Anthony. All Better Co. First Aid kits, reimagined. What do you think? I mean, questions, first of all, for Stacey or thoughts? I mean, it sounds like you've got a good amount of early traction, right? I mean, you got 200K in lifetime sales. And I guess the balance is between, you know, do you lean more into retail or are the online DTC channels the thing to lean into?

Is that sort of it? Or is there like a third place that might be promising? Yeah. I mean, our three main channels, right, are DTC, which we imagine that we'll always maintain because I think that really having connection with our consumers and important. We're two moms where we are family driven, and so that's really important. But we see our primary channels as e-commerce brand, like a thrive market or Amazon, and then retail, mass market. I mean, I think the ultimate price for us is a mass retailer like a target or, you know, we're definitely going down the natural path, grocer route.

It's just really expensive to be into retail. A quick question. Who are your customers like you and your co-founder? I mean, do you think of your customers as moms who are going to have these in their bags or their purse or whatever? Or do you think more broadly? I think that's a really great question. And it's funny when people ask us who are demographic is we say anyone with skin. I would say, though, our primary target audience, we are definitely speaking to moms.

We feel like moms are the original influencer, right? They're the gatekeepers to their communities. And yes, we make all of our products thinking three steps ahead, as we believe moms do, right? So everything we make is in a travel size. We think about our dispensers and how we're, like, for example, our pen or our cream is not in a tube. It's actually in a lip gloss dispenser. And so the idea behind it is that there's not as much waste. A child or any person could put it on with one hand.

And it's really, you can pack it on the go. And then I feel like there's a halo effect. Once you get to mom, right, you're getting to her friends. She just has this social currency. And so, but we have a lot of like Jen Ziers and young people that love our products, again, because of that travel nature that we're thinking about everything with ease. And it's better, right? We're committed to making everything chemical free and as clean as possible.

Got it. Building on that travel nature idea, one of the places that I have recently discovered, a couple of brands that I wouldn't have known about are actually via hotel partnerships. They had put certain brands in the rooms. Yeah. And I actually became like big buyers of certain brands via that where it's kind of a free sample but kind of selected.

And if I have an affinity towards the hotel chain, you know, thinking about like, hey, you know, let's try that out. Or even like, I mean, hopefully you're not hurt at the hotel, but like, I don't know, take it, right? And then that way you kind of are giving it out a non-jointed, cheesy free sample sort of way. And it's related to travel. I don't know.

Is that, would that ever come up? Yeah, absolutely. I think, like, those big brands, like, especially the family brands, like a Hilton or Hyatt, we're currently in about six different four seasons properties, which is a little bit, I think, which I think is actually a little bit more premium than we want our brand to be. We're in some auto camps, which is a really, really cool, like, mobile park resort type of place. Absolutely. I think you kind of nailed it, right? Like, we have products that people might not

pack, but then they need them in an urgent situation. And I guess the question is, how do we, we continue to seed product, put it as many places as we can, but it's that idea, right? You might not buy the hydrochortisone or something to relieve that itch until you need it, but, or are bandades, bandages, most people don't know that a huge percentage of current bandages. And or bandages on the market are full of forever chemicals, PFAs, they are sitting in our landfills. So it's like these types of things that people probably don't even like think about on a daily basis. And as a society, we think so much what we're putting into our bodies, but we're not thinking about what we're putting on our body, our skin, which is our body's

largest organ. I think that all of that is really compelling. And I think when people hear about those things, it does inform their choices. But I keep thinking back to so many brands we've done on the show. And what it comes down to is convenience and price and effectiveness, right, efficacy. And so you clearly have all three of those, right? You have a product that works, that people like. And I think really it's your, you've got a beautiful branding. It's a great name. But educating people about that's going to take a lot of time. To me, it seems like this on the channel strategy is really critical. The direct-to-consumer's harder, Anthony, you could talk about that, right? Even with Squarespace, even with all of the things, the tools that are available to people, there's just

more noise out there. And I feel like having an omni-channel strategy where you can get this in as many places as possible, especially airport shops where people are traveling quickly. If I go to the airport, I forgot shaving cream, I'm going to spend $10 on whatever I can buy at that store. You know, and I feel like here in San Francisco, there's some great stores at the airport gift shops. I feel like that's really, it's going to sell itself simply because it looks good. It's got a great name. And then maybe on the product over time, you can think about simple ways to explain that story. You know, plant-based, chemical-free, better for you, whatever you want to say, that you can quickly, you know, sort of transmit to consumers on the label.

because that's really where people are going to find out about it. Yes, they'll find out about it from influencers and from other moms. It's just going to take more time. So I feel like you really want to focus on getting it into as many places as possible where people make convenience purchases. Yeah, that's great. Thank you. I guess that was maybe my question, too.

It's like, where is that purchase? Is it a convenience purchase? Is it an impulse purchase? Is it when did people have this kind of purchase on their minds? Like, is it part of another site? Yeah. I mean, it's so interesting because the truth is, because of our branding in a really weird way, we can live so many places, right? We can live at the cash wrap as an impulse purchase. I love the idea of airports. That would be like huge for us, no doubt. I think that's really

great observation. Thank you. And maybe that's it. Maybe it's like just getting more people to find out about us when they meet us. And then when they go home, they're reminded, hey, I need to replace those band-aids with what I found from Albederco when I was traveling. And maybe that's the switch that needs to be flipped right there. Yeah, and I think your branding lends itself, I'm taking a look at the website now. I think it looks great. And it lends itself to not being like a, I don't know how to put this, like a sterile medical purchase. Like going and buying like neosporin or something, feels different than buying what you have because of how you're positioning it. And I'm sort of wondering what that enables you to do that, like, neosporin can't do.

You know what I mean? Because that's like... Yeah, it's a perfect example because if you speak to any dermatologist, they're actually going to tell you that neosporin is the one thing they don't want you to use. It actually causes more harm than good. And there are more people allergic to it than we think about. So that's a perfect example right there. I just think that's an uphill battle for now.

If you had $20 million to spread that message, that's one thing. You've got a great brand. You've got great branding. You got to focus on just as a good product. It's like method soap. They didn't say, hey, it's organic and plant-based. It was. It's a beautiful bottle, and it works well.

I really feel like that's what you want to lean into. If you want to send that message, I don't see it on your packaging. I see better bandage. I see a bamboo bandage. I see biodegradable latex-free. I don't see that message that you're, but then you go on the website and it says, you know, sensitive to skin. And so I feel like you can use the packaging a bit better to just add some of that stuff because better bandage isn't enough. It's tell me why. Yeah. Sense, better for sense of skin. Amazing. Okay. This is, this is better than NeoSport. Obviously, you don't want to get in a lawsuit with them. But, you know, better for you than the, you know, better for you than the leading. you know, anti-whatever bacterial brand or whatever it is, you know, something like that. We don't use chemicals or something like that.

But I do think that you want to just have a couple of, I think RX-Barr nailed it. It's like four eggs, you know, six almonds. It was all the macros. You see that on like pints of ice cream, this idea of just simple macros. Take what you see in food with seven grams of protein, 10 grams of fiber or whatever, and apply that to what you're doing. And I'm going to echo what you think. Like, I'm on the, I'm on the side looking at the products. I don't get the, I wouldn't have known a lot of what you're saying there about, like, you know, alternative products and what the negatives might be.

Like, I don't get the education part from a glance at this. And I might have appreciated that because I've actually never even heard anyone say that. So, you know, just look at food. I'm holding, I don't know, this brand is a brand of bars here, keto bar. It's a 17 fat, 2 grams of net carbs, 12. protein. This is a thing that food is doing really well. And I think simple messages like that could work. We got to run. Thank you for calling in Stacey. The brand is called All Better Co. Good luck. We're cheering you on. Thank you for having me. Thank you so much.

Congrats. All right. We're going to take another quick break, but we'll be right back with another caller. Stay with us. I'm Guy Raz and you're listening to the advice line right here on how I built this lab. Welcome back to the advice line on how I built this Lab. I'm Guy Raz, and I'm with Anthony Casalena. He is the founder of Squarespace, and we are taking your calls. And Anthony, are you ready for our next call? I sure am. All right, let's bring in our next caller. Hello, you welcome to the device line. Tell us your name where you're calling from, and just a little bit about your business, please. Hello, hi, Guy, and Anthony. My name is Mahak Mohan. I'm calling in from New York City. I am the co-founder and CEO of Kahani, which is a personalized recovery

companion for eating disorders. Awesome. Welcome to the show. Thanks for calling it. So this is an app that helps people in recovery from eating disorders. And tell me what it does. And tell me a little bit about it. Yes. So my co-founder and I actually built this when I was at Stanford Business School. And we kind of partnered with some of the leading clinical psychologists to think about how we could make recovery more accessible, meaning how do we apply evidence-based therapies, in a bite-sized format that's then able to be personalized to an individual's unique goals, patterns, triggers, and behaviors. And that way, you can have a 24-7 companion because recovery isn't just happening at 2 p.m. on a Wednesday. Awesome. Wait, wait, wait, we met before,

haven't we? We did. Yes. We did, yeah, through Adam Grant. Okay, I remember you now. Yeah. So, so, okay, so this is cool. So you've got this thing, and it's, it helps people get through eating disorders and tell me a little bit about where it is now. I mean, I, because you guys recently launched this, right, in the last year? Yeah. So I think right after we talked, we closed our pre-seed round, which happened at the end of June. And so now we're tugging along, building the second version of the app. And this is kind of a reimagined landscape where we're sort of sitting in between this happy medium of being gamified and engaging, as we know, lots of consumer apps must be. But also not to be. But also not to be.

clinical focused. And so we want to create this beautiful blend of skill-based progression so that you actually feel like you're recovering. And it's not too much on the gamification side. Like there are a lot of apps like that these days. So we're about to launch and that actually leads into my question around the App Store, which is our biggest milestone is we're about to come out of private beta in the next couple of months. We're about to launch on the App Store. And so I was really curious to learn more about most unique go-to-market strategies, to be able to create the most effective launch, specifically for our target demographic.

And just briefly, how will this, this will be a subscription model? You will pay monthly to use this? Correct. Got it. Okay. So now you are about to launch in the app store. You're looking to figure out how do you get people to be aware of it, right?

There's millions of apps out there, right? How do you get people to adopt this? Anthony, I want to bring you in here because we probably lots of questions and also some thoughts on how to do that. So the challenge is obviously that there's millions of apps out there. And then there's also a fatigue related to apps. I think that I don't have the stats off the top of my head, but I feel it personally myself. It's like it's kind of a lot for me to install a new app. obviously, you know, something

gets targeted as yours, I think there'd be maybe less resistance to, but I guess I would say this. If imagine it wasn't even an app, where do I find it? And does it need to be an app? Does it have, could it be a website that then

leads you to an app once you use it? So, imagining it wasn't an app because I'm actually not somebody who's ever been successful or really launched a lot of things in the app store that weren't related to another thing. How do people find it? How do they, how do they find it? So this is a really interesting question because, to your point, like many things,

recovery is not linear. And so motivation can wax in Wayne. So we started to think about less so of the demographics of the type of person who might use this and more so of the psychographics, of the type of individual who's motivated and in that place in recovery in which they're looking for extra support. This is likely someone who's been through lots of different treatment centers. They've been through higher levels of care, come back down, cycled through, and now they're really focused on recovery because they've probably a bigger goal, something of a life change that's occurring. So there are two kind of parts of this dynamic that we've thought about in terms of where people might find the app, one being when you might come off of a treatment center or a higher

acuity level of care, and two, maybe when you're in an outpatient setting. So you have a current therapist or a dietitian, but that's not good enough because you're spending a lot of time on TikTok in between sessions. You're spending a lot of time, you know, in your day-to-day, maybe you work is really stressful. And so there's a real opportunity to target. Our users have actually probably found us through lots of community engagement. So you're also in the place in recovery in which you are not in denial. So that's a big piece because maybe they're in a community group like Facebook or in a TikTok chat. Yeah. I'm curious, and I think I asked you this when we first met, not on the show.

I remember we talked and I said, you know, I don't know about this. I'm a 50-year-old man. And I think you would mention to me that many of your potential customers are women and women in a certain age demographic. Is that fair to say? Yeah, so this was actually one of the most interesting things we learned in our first pilot, which is what motivated us to keep building this out. is initially you think of a gamified sort of, you know, fun, cutesy, engaging app and you think maybe teen women would be the most likely to use something like this. And sure, we do have lots of teen women using this app. But what we learned is that based on the psychographics and

the type of engagement and retention data we were seeing, it was actually women in their 30s and 40s who ended up being the most engaged because they weren't in denial of an eating disorder. They were looking for recovery. They tried a lot of things before. And they were probably in a moment of life change. Maybe it's a wedding, a job change, finishing a graduate degree. And this is becoming now, not recovering is a big hindrance to achieving those goals. I know you've got, you just went through, you tested it out with people and you had a test group. Do you have more roughly 50, 60, 100 users total? Yes. We have about 100 users who've tested this out. We saw a 23% symptom decrease in four weeks with super users who used it for more than seven minutes a day.

Some people seeing 60 to 70 percent decreases in symptoms in that time span. They have to be your early ambassadors. That is where you're going to build this out. It's going to be slow but then fast, which is they, I mean, I wonder if you can build a closed community on Slack or Circle or one of these places because they, these are your ambassadors. I have a friend with sciatica, okay? and I said, hey, he's going to do all kinds of expensive physical therapy. I said, great, do that.

He's the thing about surgery. I said, try this out too. There's a guy who does all these amazing videos on stretching. I've been using it for three years. I tell people about this all the time because it has transformed my flexibility. And that's where you are going to really, if you're saying, hey, 23%, you know, decrease or better outcomes. Those are your ambassadors.

Can you incentivize them? Sorry, Anthony, go ahead. So my question is sort of building on the vein you're in. So without knowing the app, was the method or the things developed in the app based on a known protocol that a doctor's developed or something? Or is it something you guys have discovered and you are the authority that, you know, is the person, you know, talking through this? And I guess where that would go is, you know, if it's based on some. known branded method, okay, obviously that's your angle. If it's not a known branded method, that maybe makes you the storyteller for this method. And, you know, could you be that,

that personality that people are going to look to, you know, know, know that story? Yeah. So that is a really, a really interesting element of what we're doing is we are leveraging studies that have been done in hundreds of clinical trials where there's evidence. of CBT, so cognitive behavioral therapy, DBT, and, you know, so other forms of evidence-based therapies that have all worked in different veins for, for treatment, for eating disorders. And so we've basically curated all of these exercises and broken them down into deeply personal applications into someone's current lived experience. So what they've got in their current day-to-day routine, how can we apply these therapies so it's actually relevant like they would do,

homework-wise, in between therapy sessions. So we're not creating anything new, but we are creating a new implementation, let's say, of it. Really, I would imagine one of the ways to get this into people's brain space is to target, you know, targeted ads. I mean, there are people who are going to be searching for, you know, eating disorder, help. And so there are ways to target those people, but we know that customer acquisition costs have just skyrocketed over the last five years. And you don't have a $30-50 million ad war chest. But you do want to experiment with some of that. But I also wonder whether some of your users might be willing to go public and allow you to create some social media content with them telling their stories.

Yeah. We actually had one person from our pilot, our first pilot, post a really long TikTok video on how she was able to use Kahani and some of the, impact it had on her and that we were looking for more people to help us build out the second version. And because of the TikTok algorithm, we actually ended up getting maybe five or six organic inbounds. And I didn't even know this had been posted because I didn't have a TikTok at that time. And so it was really interesting getting emails saying, I found you on TikTok. I'm like, no way. I don't have a TikTok. So it's really interesting to see that. And so that is, I think, the hope. That is, I think, a bit of a demographic split on maybe our younger participants.

would be more willing to do that. I haven't seen excitement from our older participants to do that, and they are more highly engaged ones. So hopefully that might change, but that's certainly something we're trying to play around with a little bit more. I mean, some combination of those vulnerable stories that can relate to people authentically and maybe spread virally is, I think, great. And I like the numbers you used.

You were like, we got five. That's amazing. That you can get 10. Then you can get 20, right? You didn't say, like, how do we get a thousand? Like, you know, I'm a big fan of that sort of snowball spreading and you encouraging the mechanisms of why it has spread. But, again, the vulnerable stories are, I think, what everyone wants to kind of hear and search for. For sure.

The app is called Kahani, Mahak Mohan. Thanks so much. Good luck. And turn you on. Let's know how it goes. Thank you. Thank you. Thank you.

Yeah, I, you know, I think that it's like a trust. I mean, again, you know this. It's like the best form of marketing is word of mouth because if somebody you know is using it, you trust them. And they're like, this is really good. I'm not going to, you know, I'm not going to recommend something to somebody, especially if it's expensive or, you know, commitment of, you know, cash up front that, that unless I really think it's great. And also the ability to talk about how it actually authentically helped you. Yes. is going to be better than any, you know, paid marketing you could ever do.

Yeah, it's interesting because I, you know, admittedly, I don't know what the total addressable market is here because I don't, you know, I'm lucky. I don't have one, right? I don't have anything. Or I don't know. Right. Or I don't know. Right. Maybe I do. I don't know.

But it's a, it's an interesting idea. And I, you know, and listen, she's smart. She's smart entrepreneur. Yeah. And so clearly there's something to this. Anthony, before I let you go, I want to ask you one question, which is now that you have. You know, you've gone public. Now you're private again.

You've running a hugely successful business. Start out as a little, you know, a little website software. Now it's a full package, e-commerce, you know, business. If you could go back to you, you know, this programming nerd and, you know, 22-year-old kid and you're like, hey, Anthony, I'm coming back from the future and I'm telling you this was going to happen. But just so you know, I want to give you some advice now because this is, you know, you're going to. important for you to know. What do you think you would be able to say now that you know all this stuff? I think the thing everyone says, you know, follow your gut, right? And sometimes you do. And sometimes that takes a while. And I think that I would look back and go, you know, what decisions

do I always delay on? And I'm always looking back and going, I wish I had done that faster. And I wonder why I've never gone to those decisions and gone, wow, I went too fast. And I'm on that one, right? Like, why does it always error in one direction? And what does that mean? And I think I try and watch out for that stuff now and realize that sometimes I never move too quick on certain things and just kind of keep that in mind.

And it's like you could have just gone faster. You knew what to do. I love it. It's great advice. It's Anthony Casillana founder and CEO of Squarespace. Anthony, thanks so much for coming back on the show. Yeah, real pleasure. Thanks for having me.

I'm honored. So fun. And by the way, if you guys haven't heard Anthony's, original how I built this episode. You've got to go back, check it out. We'll put a link to it in the show notes, the podcast description. And here's one of my favorite moments from that interview. Somewhere along the way, I get like a call on my cell phone from like a customer. Guys like, hey, is Squarespace okay? So I call the data center. I'm like, hey, can you reboot this server? And it doesn't come back. And it wasn't coming back. Completely crashed. Wow. And I was like, I got to go to New York right now. And I just drive to New York. And I'm like having a panic head. the whole way up because I'm like, it's screwed. I lost all the data. It's all gone. That little experiment's over. Thanks so much for listening to the show this week. Please make sure to check out my newsletter.

You can sign up for it for free at gairoz.com. Each week, it's packed with tons of insights from entrepreneurs and my own observations and experiences interviewing some of the greatest entrepreneurs ever. And if you're working on a business and you'd like to be on this show, send us a one minute message that tells us about your business, the issues, or questions you'd like help with, and hopefully we can help you with them. And make sure to tell us how to reach you. You can send us a voice memo at hibt at id.wondry.com or call us at 1-800-4331298 and leave a message there. And we'll put all this in the podcast description as well. This episode was produced by Sam Paulson with music composed by Ramtin Arableu.

It was edited by Andrea Bruce, and our audio engineer was James Willits. Our production staff also includes Alex Chung, Elaine Coates, J.C. Howard, Neba Grant, Casey Herman, Chris Messini, Catherine Seifer, Carrie Thompson, and Ramel Wood. I'm Guy Raz, and you've been listening to The Advice Line on How I Built This Lab.