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B
Pleasure to be here.
A
It's great to have you on. You were first on the show back in 2019. You told us, of course, about Squarespace's origin story and all the things that you, you learned growing Squarespace. You founded it in 2003 as a 21 year old kid. As a college student, I remember some of the stories about racing up and down I95 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 paid 200 bucks to use it. And that's kind of how it was born.
B
Yep, that's right.
A
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.
B
Yeah, we took it private. Yep.
A
Amazing. So private again. 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? Built this thing, you took it public, now it's private again. But I guess you kind of have bosses, right? I mean, I guess shareholders are your bosses, but now you've got bosses again. Does that make things more complicated? Does it really not change things a whole lot for you?
B
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, 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.
A
Tell me a little bit about how you think about expanding the business. Just full disclosure, it doesn't matter because it's a Great story. You may not even know this, but you guys advertise on how I built this and you offer. It's not just you 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.
B
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. It's a scheduling product. We acquired the assets from Google Domains. 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. We play in a lot of different lanes that help people get online. I think it's actually a funny thing and maybe there'll be some AI questions at some point, but what we do is more relevant 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 we continue to do very well and it's just kind of a pleasure to be servicing millions of entrepreneurs.
A
Yeah. 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?
B
Well, that's one way people find out about you. 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. They're crawling the web and 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 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, we're really happy to be positioned as we are in this era.
A
I know you've got AI tools already to help basically build out websites designs, and this is happening 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 that mean for your business and how it sort of fits into that, into this sort of brave new world of AI tools?
B
Yeah, I mean, it's been a phenomenal tailwind for us. I mean, we're not particularly worried about the. 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 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 Squarespace, 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, we've got AI enabled and probably 15, 20 plus touch points in the product right now.
A
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?
B
I sure am. Let's do it.
A
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.
C
Hi. Hi, Guy. Hi, Anthony. My name is Bob Zukowski. 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.
A
Wow. Well, okay, thanks for calling in. So these are custom mattresses. This is not off the shelf mattress that you just, like, add a pad or two what you like. It's like going to a tailor, you measure somebody and then you take all that data and you build a mattress with that in mind from the ground up.
C
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.
A
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?
C
So queens are, you know, in the 3800 range, Kings are in the 4500 range.
A
Got it. And are they. I mean, is the material any different from other mat? I mean, is it latex? Is it foam? What's in there?
C
Well, we use exclusively Talalay 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 and you get the body in the right position, then the sleeper has the greatest opportunity of achieving high quality REM and slow wave sleep.
A
How did you get into this? This is a very complicated business. We've done tempur pedica on the show, We've done some other mattress brands like Casper, and this is not easy. So how did. Were you in this business before?
C
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 Talalay into their products. And I came to believe that their number one priority was not how their customers slept, but that their masters wouldn't fail in the field. And then I started doing my own research, pressure mapping, my friends and 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.
A
All right, quick question, and I want to bring Anthony in. Can you make a mattress that works for two people? Because I share a bed with my wife. And if we have different measurements, can you do that in one mattress?
C
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.
A
Got it. Okay. And what's your question for us today?
C
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.
A
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. Anthony, I want to bring you in.
B
Okay, well, I'm on the website and I'm a website person, so I'm just going to go out and say the site 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, this is. I don't know, you got to kind of catch me with the branding or something. So.
A
Yeah, I agree. I think. I mean, listen. And by the way, we're talking about if it's Anthony buying a mattress here, Bob, we're talking about the Swedish. That one that's like, you know, $100,000 mattress. That's what he's buying. That's what he's doing. He's getting that, like, by the tiny little elves in, you know, some. Some Nordic town, making them by hand. Yeah.
B
But I'm gonna 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 horse hair 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 rich materials message. So I think there's a world fee for people there who don't want to necessarily be. 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.
A
But if you knew, like, we know. I know that Bob, who's been in this business for decades, knows how to do this. 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.
B
Maybe get. The AI agent said I was going to be blunt. I think we need a little web help here.
A
Some web help.
C
I Can appreciate that, thank you.
A
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 because I trust this guy. Because see, I can talk to you here and say that. But your website, not everyone's going to talk to you. Your website's what's talking to people and how you. And so 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 some interesting brats, I think that could be a cool idea, especially if you can somehow integrate some of the technology. Obviously there's eight sleep that measures your sleep. And could you put an eight sleep on top of this mattress? Could it be designed? Could you work with oura rings 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 Tempur, Pedic 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 it 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 is 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.
B
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 at and 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 from zero.
A
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 different densities. And you mentioned this latex. What was the latex that you use again? Talalay, 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 Talalay, what does that mean? You need to somehow convey that at Least starting with the website, because that's gonna explain the whole brand to people. Right. It's like personalized sleep system. Well, eight Sleep says that and Tempur Pedic 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.
B
Right.
C
And we can modify it over time so we build it to your existing body profile and then we can change it over time.
A
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.
B
I gain £100, I call you. I lose £100, I call you. We just keep adjusting.
C
That's right. That's how we do it.
A
That's awesome. All right. The company's called Custom Sleep Technology. Robert Zukowski, thanks so much for calling and good luck.
C
Thank you. Thank you both for your time.
B
Thank you. Good luck.
A
Yeah. So you're sleeping on horsehair now, Anthony? Zach.
B
No, no, no, no, no. I'm not susceptible to these horse hair.
A
To these.
B
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.
A
All right, we're going to take a quick break, but we'll be right back with another collar 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. You know, one of the most surprising things about how I built this is just how many pitches we get. Every year, tens of thousands of businesses reach out, hoping to tell their story. Now, while we do try to read most of those pitches, we can't possibly read all. But we choose most of our guests through our own deep research. And that means my team and I spend hundreds of hours digging into companies, what they make, who's behind them, and whether their journey can inspire you. And that's exactly where Claude has become such an incredible thinking partner. In my creative process, Claude is the AI for minds that don't stop at good enough. The thinking partner that works with you to explore the things that fascinate you. Whether you're researching late night curiosity spirals or working through complex creative challenges, Claude extends your thinking to tackle the problems together. For example, imagine I'm about to sit down with a founder of a snack company. I'll want to know what products they've released, how they've evolved, and which competitors they're up against. In the past, it could take hours to track down reliable details. We'd search articles, databases, reports. Now Claude can give me a clear answer in seconds, and then I can decide what to dig into further. It doesn't replace my process, but it sharpens it. And that means I can spend more time doing what I love most, focusing on the human stories, the lessons, the decisions and the struggles behind the businesses you hear on this show. Experience what collaborative thinking feels like at Claude AI Hibt and see why the world's best problem solvers choose Claude as their thinking partner. This show is brought to you by American Express. Running a business means making countless choices every day, some small and some that can change everything. The business owners who thrive are the ones who are ready for whatever comes next. And having the right support behind those decisions can make all the difference. That's why so many business owners I talk to choose the American Express Business Platinum card. It's built to help them move quickly and take their business further. And with five times membership rewards, points on flights and prepaid hotels booked through amextravel.com, you can turn any business trip into a chance to earn more and invest in your business's future. Plus, you get a flexible spending limit that changes as your business does, adapting to where you are and where you're headed next. Because when it comes to growing your business, there's truly nothing like Business Platinum. Not all purchases will be approved. Terms apply. Learn more at Go Amex Business B Platt if you've shopped online, chances are you've bought from a business powered by Shopify. You know that purple shop pay button you see at checkout? The one that makes buying so incredibly easy? That's Shopify. And there's a reason so many businesses sell with it. Because Shopify doesn't just make amazing buying experiences for customers, they're also the experts in helping small businesses grow big. Stop seeing carts going abandoned and turn those sales into Sign up for your $1 per month trial and start selling today at shopify.com bilt go to shopify.com bilt shopify.com built. 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 are 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.
D
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 company and we are reimagining mom's first aid kit with Better for your, Better for the Planet daily skin health essentials.
A
Awesome. Thanks for calling in. Welcome to the show. Thank you. So All Better company, you sell first aid kits. So like band aids and I don't know like acid tracin and stuff like that?
D
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 hydrocortisone. Right. So anti rich, anti inflammatory, the same way you'd use hydrocortisone. We don't want you to do that. We want to use our product instead.
A
Nice. And where are they being sold right now?
D
Mainly so we're D2C Amazon and we're in about 100 plus retail locations across the country including Erewhon, a few resorts and we're really kind of actually testing these channels and see where we live best.
A
Tell me how the idea came about.
D
Yeah, so I come from brand, I have brand background in 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.
A
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.
D
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 seeding, 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 at about 200,000 lifetime sales.
A
Amazing. And before I forget, tell us what your question is.
D
Sure, absolutely. So, as I said, we're a bootstrap female founded brand and we are bringing clean beauty standards to the first aid 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 Neosporin 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?
A
All right, awesome. I want to bring you in, Anthony. All better company. First aid kits reimagined. What do you think? Questions? First of all for Stacy or thoughts?
B
It sounds like you've got a good amount of early traction. You got 200k in lifetime sales. I guess the balance is between. Do you lean more into retail or are the online DTC channels the thing to lean into? Is that it or is there a third place that might be promising?
D
Yeah, our three main channels are dtc, which we imagine that we'll always maintain because I think that really having connection with our consumer is important. We're two moms. We are family driven and so that's really important. But we see our primary channels as E commerce, 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 we're definitely going down the natural path, grocer route. It's just really expensive to be into retail.
A
A quick question. Who are your. 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?
D
I think that's a really great question. And it's funny, when people ask us who our 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 Gen Z ers 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.
A
Got it.
B
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 the hotel partnerships. They had put them. They had put certain brands in the rooms 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 in case. And then that way you kind of are giving it out in a non cheesy free sample sort of way and it's related to travel. I don't know, is that, did that.
D
Ever come up or is that, I think like those big brands like especially the family brands like a Hilton or a Hyatt. We're currently in about six different Four Seasons properties, which is a little bit.
B
I think, oh, amazing.
D
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 as many places as we can. But it's that idea, right? You might not buy the hydrocortisone or something to relieve that itch until you need it, but. Or our band aids, bandages. Most people don't know that a huge percentage of current band aids 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.
A
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, you've got beautiful, 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 omnichannel strategy is really critical. The direct to consumer is harder. Anthony, you could talk about that. 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 omnichannel 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 bucks on whatever I can buy at that store. And I feel like here in San Francisco there's some great stores at the airports, 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. Plant based, chemical free, better for you, whatever you want to say that you can quickly trans, 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. That'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.
D
Yeah, that's great. Thank you.
B
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? When do people have this kind of purchase on their minds? Is it part of another cycle?
D
Yeah. I mean, that'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. I love the idea of airports. That would be huge for us. No doubt. I think that's really great observation. Thank you. And maybe that's it. Maybe it's just getting more people to find out about us when they need us. And then when they go home, they're reminded, hey, I need to replace those band aids with what I found from Albertco when I was traveling. And maybe that's the switch that needs to be flipped right there.
B
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.
D
Yeah, it's a perfect example because if you speak to any dermatologist, they're actually gonna 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.
A
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 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. They just said 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, sensitive to skin. 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 Sense. Better for sense of skin. Amazing. Okay. This is better than Neosporin. Obviously you don't want to get in a lawsuit with them, but you know, better 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 RXBar. Nailed it. It's like four eggs, six almonds. It was all the macros. You see that on pints of ice cream. This idea of just simple macros. Take what you see in food with 7 grams of protein, 10 grams of fiber or whatever and apply that to what you're doing.
B
And I'm gonna echo what you're saying. 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 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.
A
I don't know. This is a brand of bars here. Keto bar. It says 17 fat, 2 grams of car net carbs, 12 protein. This is a thing that food is doing really well. And I think simple messages like that could work. We gotta run. Thank you for calling in, Stacy. The brand is called All Better Company. Good luck. We're cheering you on.
D
Thank you for having us.
B
Good luck.
D
Thank you so much.
A
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. We all have moments when we could have done better. Like cutting your own hair. Yikes. Or forgetting sunscreen. So now you look like a tomato. Ouch. Coulda done better. Same goes for where you invest. Level up and invest smarter with Schwab. Get market insights, education and human help when you need it. Learn more@schwab.com startups move fast. And with AI, they're shipping even faster and attracting enterprise buyers sooner. But big deals bring even bigger security and compliance requirements. A SOC 2 isn't always enough. The right kind of security can make a deal or break it. But what founder or engineer can afford to take time away from building their company? Vanta's AI and automation make it easy to get big deal ready in days. And Vanta continuously monitors your compliance, so future deals are never blocked. Plus plus Vanta scales with you backed by support. That's there when you need it. Every step of the way my listeners can get $1,000 off at vanta.combilt that's V A N T A dot com bilt for $1,000 off. 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?
B
I sure am.
A
All right, let's bring in our next caller. Hello, you, welcome to the advice line. Tell us your name, where you're calling from, and just a little bit about your business, please.
E
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.
A
Awesome. Welcome to the show. Thanks for calling in. So this is an app that helps people in recovery from eating disorders. And tell me what, what it does and why. Yeah, tell me a little bit about it.
E
Yes. So my co founder and I actually built this when we were 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 2pm on a Wednesday.
A
Awesome. We met before, haven't we?
E
We did, yes, we did.
B
Yeah.
A
Through Adam Grant. Okay, I remember you now. Yeah. Okay, so this is cool. So you've got this thing and it helps people get through eating disorders. And tell me a little bit about where it is now. Cause you guys recently launched this, right? In the last year.
E
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 chugging along building the second version of the. 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 too 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.
A
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 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 have lots of questions and also some thoughts on how to do that.
B
So the challenge is obviously that there's millions of apps out there, and then there's also a fatigue related to apps. I don't have the stats off the top of my head, but I feel it personally myself. It's kind of a lot for me to install a new app. Obviously, something as targeted as yours, I think there'd be maybe less resistance to. But I guess I would say this. Imagine it wasn't even an app. Where do I find it and does it need to be an app? 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 find it?
E
This is a really interesting question because to your point, like many things, recovery is not linear and so motivation can wax and wane. 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 have 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 in your day to day. Maybe your 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.
A
Yeah. Meic, 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. So. And I think you had mentioned to me that many of your potential customers are women and women in a certain age demographic. Is that fair to say?
E
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, but not recovering is a big hindrance to achieving those goals.
A
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?
E
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% decrease, decreases in symptoms in that time span.
A
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 these are your Ambassadors. I have a friend who has sciatica. Okay. And I said, hey, he's going to do all kinds of expensive physical therapy. I said, great, do that. He's thinking 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% decrease or increase better outcomes, those are your ambassadors. Can you incentivize them? Sorry, Anthony, go ahead.
B
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 is the person talking through this. And I guess where that would go is 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 could you be that personality that people are going to look to know that story?
E
Yeah. So that is 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, 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.
A
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 gonna 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 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.
E
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 was really interesting to. 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 our 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.
B
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. If you can get 10, then you can get 20. Right? You didn't say, like, how do we get a thousand? 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.
A
The app is called Kahani Mahakmohan. Thanks so much. Good luck and churn you on. Let us know how it goes.
E
Thank you so much.
B
Thank you.
A
Thank you. Yeah, I think that it's like, I mean, again, you know this. 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 gonna. You know, I'm not gonna recommend something to somebody, especially if it's expensive or a commitment of cash upfront, unless I really think it's great.
B
And also, the ability to talk about how it actually authentically helped you is going to be better than any paid marketing you could ever do.
A
Yeah, it's interesting because admittedly, I don't know what the total addressable market is here, because I'm lucky. I don't have one. I don't have any, or I don't know anybody who does. Maybe I do I don't know, but it's an interesting idea and I, you know, and listen, she's smart. She's a smart entrepreneur 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. Started as a little, you know, little website software, now it's full blogging's, 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 important for you to know. What do you think you would be able to say now that you know all this stuff?
B
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, 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 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.
A
I love it. It's great advice. It's Anthony Casalena, founder and CEO of Squarespace. Anthony, thanks so much for coming back on the show.
B
Real pleasure. Thanks for having me. I'm honored.
A
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 is one of my favorite moments from that interview.
B
Somewhere along the way, I get like a call on my cell phone from like a customer. A guy's 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.
A
Wow.
B
And I was like, I gotta go to New York right now. And I just drive to New York and I'm having a panic attack the whole way up because I'm getting screwed. I lost all the data. It's all gone. That little experiment's over.
A
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@guyraz.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 to like 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@hibtid.wondery.com or call us at 1-800-433-1298 and leave a message there and we'll call. Put all this in the podcast description as well. This episode was produced by Sam Paulson with music composed by Ramtin Arablouei. 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, Neva Grant, Casey Herman, Chris Masini, Kathryn Cipher, Kerry Thompson, and Rommel Wood. I'm Guy Raz and you've been listening to the advice line on how I built this label. If you like how I built this, you can listen early and ad free right now by joining Wondery plus in the Wondery app or on Apple Podcasts. Prime members can listen ad free on Amazon Music. Before you go, tell us about yourself by filling out a short survey@wondery.com survey.
Release Date: November 20, 2025
Host: Guy Raz
Guest: Anthony Casalena, Founder & CEO, Squarespace
This episode of “How I Built This: Advice Line” features Anthony Casalena, the founder and longstanding CEO of Squarespace. Guy Raz and Anthony take calls from three entrepreneurs at various stages in their journeys, offering tactical, real-world advice about digital branding, omnichannel strategy, word-of-mouth growth, and leveraging early adopters. Guy and Anthony’s open, often blunt, dialogue makes for a master class on building trust, branding, and scaling a business in rapidly evolving markets.
Timestamps: 03:33–09:48
Caller: Bob Zukowski, Newtown, CT
Timestamps: 10:12–20:03
Caller: Stacey Bernstein, Los Angeles, CA
Timestamps: 24:49–38:12
Caller: Mahak Mohan, New York City
Timestamps: 40:22–51:37
Anthony on always having a “boss” as a founder:
“Even if you owned 100% [of the company] yourself, your customers would be your boss.” – Anthony, 05:10
Anthony’s advice on branding and digital presence:
“Your website’s what’s talking to people… You need to basically make it so people can say, yeah, I’ll do that.” – Anthony, 16:36
Brand-positioning insight:
“I am susceptible to what I would call more of a scientific message than a rich materials message.” – Anthony, 15:22
On moving faster as a founder:
“I would look back and go, what decisions do I always delay on? And I’m always looking back and going, I wish I had done that faster. …Why does it always err in one direction?” – Anthony, 53:11
On organic, snowball marketing for apps:
“You were like, we got five [users via TikTok]. That’s amazing. If you can get 10, then you can get 20. …I’m a big fan of that sort of snowball spreading and you encouraging the mechanisms of why it has spread.” – Anthony, 51:00
Guy connecting omnichannel to branding:
“Focus on getting [the product] into as many places as possible where people make convenience purchases.” – Guy, 34:22
| Segment | Timestamp | Highlights | |--------------------------|----------------------|--------------------------------------------------| | Squarespace’s Journey | 03:33–09:48 | IPO, going private, AI, company relevance | | Custom Sleep Tech Call | 10:12–20:03 | Digital trust, scientific messaging, partnerships| | All Better Co. Call | 24:49–38:12 | Omnichannel, on-pack comms, travel retail | | Kahani App Call | 40:22–51:37 | Word-of-mouth, user ambassador strategy | | Anthony’s Final Advice | 53:11–54:01 | Move faster, trust your gut |
This rich, transparent episode demonstrates how entrepreneurial strategy, digital branding, and customer-centricity can unlock growth for any stage of business — from the kitchen table to the App Store.