Squarespace: Anthony Casalena

Somewhere Along the way. I get like a call on my cell phone from like a cost Guys like hey uh Is Scorespace 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 crash. Wow.

And I was like, I gotta go to New York right now. And I just drive to New York and I'm like having a panic attack the whole way up because I'm like it's screwed I lost all the data. Saga. That little experiment's over. From NPR, it's how I built this, a show about innovators, entrepreneurs, idealists.

Stories behind the movements. They go. Guy Ross and on today's show How Anthony Casalena's dorm room coding project grew up. Turned into square space. And now Anthony grew up

With it. So in business schools, they teach a bunch of ideas about entrepreneurship, but the simplest one, the one that is the clearest path to creating something unique? is this? Find a problem that lots of people have? And solve it.

So for example How can I get from this exact point I'm standing on? to another specific point two miles away. in a relatively fast and cheap way. Well, in most cities in America

Uber and Lyft have solved that problem. Or how can I get a cheap pair of cool prescription glasses? That's the question the guys behind Warby Parker wanted to answer. Or what about How do I build my own website? Okay, I think you know where this is going, because today That is not a problem.

But not that long ago. Tip. Build a website? You either needed to know how to code. or know someone else who knew how to code and charged you money to make that site. And this, of course, was the problem that Anthony Casolena wanted to solve.

Now before I go on I'm gonna acknowledge the elephant in the room here because yes, in the past, Squarespace has sponsored this podcast. And so have other companies that do similar things. And I promise you. That fact will never influence which companies we profile on the show.

We look for great stories and the story of Squarespace, as you will hear. is pretty great. Anthony Casalena literally created his product in a dorm room. at the University of Maryland in two thousand three. He was 21, a self-taught coder.

and looking for a way to combine a blog and a website, go figure! And out of that small problem he wanted to solve? Came Square Space. It's a company that's now valued at around$1.7 billion. Anthony grew up outside Baltimore in the early 90s.

just as the internet was becoming a mainstream thing. His dad worked in sales for companies like HP and Cisco, so Anthony was exposed to a lot of computer hardware. From a young age. My my dad always had computers around, so um I would break those and incur uh the wrath of my parents and um

Eventually I got to a point where They were sick of me breaking their computers and ended up buying me uh or getting one that I could break myself. Um, which I you know learned how to load games onto and learned a little bit of basic and stuff like that. And

Um and this is like the area of like, you know, two eighty sixes, three eighty sixes. DOS Windows three point one, Windows ninety five, that kinda era. But I was always really, really into that. So you so you started to to learn how to program basically as a kid, like how how old are you? probably thirteen, fourteen, because when I was fifteen I worked for an internet company in in Maryland, in Baltimore, actually. They were trying to actually recruit my dad and uh

You know, my dad was like, I'm busy, you know, I've been employed, et cetera. But you know, my son's a good programmer. You should you should talk to him. Just to put this in in the right Time frame you're talking about the mid to late nineties. I think you're talking about the mid nineties. I mean the web was really new. I mean it wasn't like a common thing And um I kinda gravitated towards this thing called um

Internet relay chat. So it's like this like global chat room you can kinda go into and It was like the wild west of the internet. Like you were connected to this to this network and You know, I remember Some of the earliest programming I did. was programming uh scripts that go into the the the the IRC client that would control it and give it new functionality and things like that. And I I also

was around people who uh knew programming. And I was obsessed with user interfaces and I learned a lot of Windows programming um because I I just wanted to know how it all how it all worked. I mean It's really cool. I don't know why I was so fascinated by all that. Um, but I was definitely into it. So you um I guess You decide when when it's time to go to college. You you went to the University of Maryland. Yeah.

and you are studying computer science and um At that time, like like people are are starting to blog and build websites and I guess you wanted to do one For yourself. Yeah, this was like

Two thousand and three. And um in two thousand three I wanted to make a website for myself and I'll say two things about doing that. One, at the time, You had all these different software programs that you would have to put together to make what you would normally think of as a a website right now, right? So you have blogging software, but that's separate than page building software, right? Like that was like at the time Dreamweaver and front page and all that. Yeah. And then you had separate software that would like tell you who's visiting the website. There'd be like stat counter or something, like there's one of these really old things. And then you have to like go and upload that somewhere and host that somewhere and there was like these old hosting

services that that you would use. I just didn't I didn't want I didn't want this mishmash of things. And the other thing that I was really into is you know, I I was just always into the way it looked, the way the interface worked and I I knew that people were gonna find this was gonna be like my how they see me online. So I wanted I wanted that to be good. So you so you wanted to create a blog and a website. You could have done that, right? Like there there was Live Journal and I've GeoCities, I didn't remember, but there were Yeah, that kinda there was th there was Typad movie. It was pretty easy to create a blog, even in two thousand three, right? Not really. No. I I I think that.

There was live journal, but that that wasn't a very I mean my site was like half professional, right? And so you didn't put your professional site on LiveJound. And it was that was blogger. at the time. Um, which again they would very personal in nature. Um, but I wanted more than just a blog. I wanted I wanted, you know, more of a more of a website and as soon as you start to do that You know, those blogging services didn't let you do that. And so you thought, All right, well, I know how to m make this stuff. Let me try to figure this out. Yeah, and and and so I started making it for myself, and I I would show people it, right? I mean they would be like, Check this thing on I made it's uh blogging software and I can make a w website with it too, isn't that cool? And I remember one of my friends being like

I'll give you two hundred bucks for that. And I'm like, okay. Maybe other people could use this. And so I started turning it into like a multi-user service where people could go and they could sign up and you know it was self-service and they could go and create their own site and things like that. And and you know it pretty quickly into

This could be a business. was the idea from the beginning to make it easy to build a website. Was that was that what you were thinking when you were creating the software? So It was always about publishing.

I wasn't gonna be able to compete. With Front page Microsoft, Dreamweaver, Macromedia and later Adobe. But when blogging happened I see it as the kind of beginning of this DIY w do it yourself wave.

Where people who would have otherwise been a little intimidated Um You know, it was this kind of like, oh, I can do this too, but then giving them something more powerful, saying, E look, you can publish a blog post, you can publish a page, you can publish a photo gal, you can do all of these things. The blog was the anchor, but it was always about doing more with it. So like take me into your I don't know, is it your dorm room? Like are you sitting in front of a computer, just fingers at the keys, just like let's get in there. I'm I've got that you, you're like twenty. So let's see. So I'm in my dorm room in the University of Maryland. The dorm was called South Campus Commons.

And I uh was in a Let me see, how many bedrooms was it? One, two, three, four. Four bedrooms. You know, it's it's tiny. It's like a single bed and uh there's my little desk in front of it and I have yeah. I'm too into computers, so I have two monitors, which was like a huge deal at the time. I mean these are like CRT monitors, right? They're these like giant, like heavy like you remember what televisions used to be like, these like ridiculous things. So yeah. So you were in your dorm room.

Just And how long did it take you to actually build this architecture? So The original version of it I started programming in 2003, April 2003, a little bit before that.

And it took me until November, December I was kinda like done and ready to launch it. So Let's say eight months. And and did you did you have uh any cash, any money, any small amount of capital to actually

try and launch this into a business? So Back then I didn't. And I did everything I could have possibly done with the

With whatever skills I had or whatever I thought I could fake, right? And so, you know. I know how to program a thing, I can write the homepage and do the write the marketing copy. I can make the interface and all that. No, there's a couple things I couldn't do, right? I couldn't invent servers to run it out of nowhere. So I needed to buy some servers. Yeah. And I needed money for the service. So I I went to my I went to my parents. Uh who, you know I don't know how I calculate, but I needed thirty grand.

And You need thirty thousand dollars to get this to get this off the ground. Yeah, I needed I needed these servers. I needed two of them, right? Because uh one crashes, then I need a redundant one, right? I worked at this Yeah, tech composed in high school. I I know that these things crash. Um and so I I remember asking my uh dad for it And it it was a fight. I I remember parking I was at the University of Maryland. I was in the the stupid parking lot outside of the door.

And I remember being on my phone. And and you know, it was like why do you need two? Why can't you have one? Why doesn't You know, that would be half. Like I mean it was a it was a it was a fight. And You know, they eventually uh

I eventually w won that fight and and they were the first investor in Squarespace. Did you call it? Squarespace already? Like w did you already pick that name? Yeah, I I can't remember exactly when I picked it, but I needed to get the the dot com, the dot net, the dot org domains. They had to be open, right? So I needed to be able to just buy them. I couldn't you know negotiate for them. Because again, I didn't have any money. So

Uh I remember Googling it at the time and there were zero Google results for Squarespace. And so I was like, Okay, we're starting from zero here. And um for some reason just thought like Okay.

Square space like monitors were more square the at the time. They weren't as rectangular. Like it's kinda your space online. I guess that works. And you know, I can probably draw the logo for this. Probably gonna pick like a square or something like that. But um yeah, I mean that's kinda that's kinda where it started. Mm. So if I ran into you junior year of college at University of Maryland, I was like, Hey Anthony, what's going on? And you're like, Oh, I'm just working on this this business and I would say, Well what what's the business? What would you say? How would you describe it? I call it a publishing system. I said, you know, as a way to make websites and blogs. And I probably would lean more into to blogging back then because it was more topical and people were like, What's that? Interesting. You know, and it again it meant that DIY thing was possible. Um

Yeah, they said it's a way for people to make websites. And so when you launched it in two thousand four, like You just I don't know. hit a button and then it and then it just like here it is. Here's Squarespace. So I won the fight with my parents on the thirty grand and Well, I got the servers, right? And so They were on the floor of my dorm room for a while.

And you know, most people have never been to the data center. These are not like normal computers. They're like really flat, really long, and really, really loud. And so they're so loud that I'd have to keep'em off. Cause otherwise it's just like intolerable. It's like terrible. And so Back at the time, I read A lot about software development. One of the blogs I read. Was this guy, um, Joel Spolsky. And um his blog was hosted in New York by a company called Pier One.

And so I was like, Oh, okay, well when I do a data center, Pier One sounds good. They like Joel. And so I um I visited New York as a kid and Th there's just something about it that I I just knew I just knew I wanted to be there. Eventually.

And so I I drove him up. In my car. Plugged everything in. and turned them on. checked that I could remotely connect to them and you know went and like had dinner in New York and then drove back to Maryland.

So so when you when you launched Squarespace um like from the perspective of a customer, it was just a a website that People would Would find Right. So

Well, I turned it on and I was like, Well, how am I gonna get people to shop? Like, I guess you can do advertising And so I bought a bunch of Google AdWords. Well, not a bunch, I bought like two hundred bucks of Google AdWords. under like build a website, make a blog, like all these different things. And A couple people came to scores. It it might have been like three. Like, I mean we're talking like

Not a lot of sign ups. Or like it can. Um By the way, what did it cost to sign up for Squarespace in those first few months, do you remember? So The little known fact is Actually for the first year.

We did have a free plan. You could actually use it for free. We always had a free trial and we still have a free trial. But back then I actually had a a free plan and the idea Yeah, there were plenty of examples of people giving away software for free and those things growing a lot. Like Blogger was free. Millions of accounts. Whatever. Like it like people would be like you give it away for free and then people are gonna upgrade. And so in the first year.

I realize that There were a lot of people who were gonna use this thing for free that were never, ever, ever going to upgrade. And Again, I'm running this like I don't have a like Other money.

So I need to like keep this thing running. So I don't want The people who are free. Who are never gonna upgrade. Using up all the server space. So and and it was really not the point of the thing. It wasn't I was not out there trying to make the next live journal or blogger. I I wanted the let me focus on the people that want to pay for this. And I forget what it costs time. Between five and fifteen bucks a month.

You know, really inexpensive. So did you um I mean in that in two thousand four, that first year I mean you were still a student. And running this thing. And what did that mean? Like how w what did your life look like at that point?

You know, it was interesting how it evolved because you know, it was a year of like at the end of the year, I mean we're probably making fifty grand a year. My parents were like, Where are you gonna get a job after college? That's a nice little side project, but where where's where's your job? And I I really start to see at the end of that year, what if I doubled or tripled that? Like I mean people are they stay around, right? Like they make a website, they're not leaving quickly. I'm gonna try and grow this. And so I actually stayed on uh instead of graduating in four years, I waited and then graduated in five and kinda took some like Mm. Let's just say pretty light workload classes on that fifth year. I was buying myself time, right? I I was buying myself out of like my parents.

really getting on my case about getting a job because I gotta pass. I'm in school. Yeah. I mean, I think that there were the inklings of how it would later impact my life, but I don't think it really had hit me. Right. I didn't see that stuff coming. Like I I I there's a lot of these events along the way. One of the early ones was I was with my friend and we were taking a road trip to Miami. So driving to Miami just like a seventeen hour drive. Somewhere along the way. I get like a call on my cell phone from like a customer. And

Uh guys like, hey uh is Squarespace okay? And I'm like I don't know. They're driving the Miami. And I just told my friend like I'm like take me to an internet cafe or something, right? Because this is ridiculous. I mean, this is two thousand four. This is a different world of internet. And I like log on and like remotely log into the servers and like reboot something and it comes back and I'm like

And it was like my first taste of this, like responsibility and uh Yeah, a little foreshadowing of of what would then happen to me later. You you graduated from college in two thousand five, right? Yeah. And by the time you graduated college

I've heard that you you guys had like about ten thousand accounts and You know, it it's starting to look pretty good. Mm-hmm. But w w you were the only person, right? You were the engineer and designer and support rep and and CEO. Yeah, it was I was kinda everything. I I mean so in the first year

I think we were like a run rate of like fifty grand. And in the second year I think we were at a run rate of like Two hundred grand. You know, it wasn't like a million bucks overnight. But it um

In year two I was able to convince my parents that, you know, I'm gonna do this and I started looking for apartments. In New York. I knew I wanted to be in New York. I put the servers there. Um

It was like the scene of these like really happy moments in my life, but also these like incredibly traumatic moments in my life where There was another thing that happened maybe A year in? Where

I didn't have a lot of space in the data center, so I couldn't actually fit all the servers in the data center. And so I had my redundant one, but it was it was in my dorm room. And so at some point this happened again. Things blacked out.

Somebody say, Hey, it's down. Okay, I try and log into it. Can't log into it. Okay. So I call the data center. I'm like, hey, can you reboot? This server. And it doesn't come back. Completely crashed. Wow. And it wasn't coming back. And I was in Maryland.

I was with m yeah, my girlfriend at the time. And I was like, I gotta go to New York right now. And so within fifteen minutes, we just got the car, put the server in the back seat. And I just drive to New York and I'm like having a panic attack the whole way up'cause I'm like it's screwed I lost all the data. Saga.

That little experiment's over. Like I I should've had the other thing there, replicated all the stuff and I I had levels of redundancy, but just not that many. And so I remember going up there and Being like, I hope this works and taking both of the comput and taking all the drives out of one and slotting them into the other. And turning the thing back on. And uh it turned on and everything was fine.

Mm. So uh after college you you decide to m to move to New York, uh obviously closer to the servers to the to the data center. Uh, and it it sounds like you just want to live there too. Yeah. So how'd you find a place?

So I went to Craigslist. Yeah, I didn't know anyone in the city and so I didn't w wanna live alone and there was no reason to incur that expense. And like I moved in with four other complete strangers off of Craigslist. and it was a five bedroom apartment on a fourth floor walk up. And I remember uh I had this uh old BMW at the Tennis Black three series. I packed everything I could into this car.

I remember driving Up to New York alone. And The first thing I did is made like an illegal turn. over twenty third street and got a ticket.

And then the second thing that happened to me was I park kind of in front of my place. I'm like, okay, I guess I have to be double park, like there's nothing else to do, but I'm gonna be running in and out of my car, it'll be fine. And Carrying all my stuff up the stairs. Literally alone. At the end of the last trip, I was just sitting there on my on my floor. And it was getting a little bit dark and I was like this take a minute.

'Cause this is just exhausting. And um I go down, my car's towed. So it's like I'm just piled with tickets and no car. And um I remember like going back up to my room And realizing like I don't even have a light in this room. Like there's no lamp. Um there's like you know, New York crap. So I go to like the tow yard or whatever on the west side. get my car and call up one of my best friends who lived in Philadelphia. And so I I went back to Philadelphia, returned to New York the next day, bought myself a lamp, bought myself a bed, and uh went on from there.

Yeah, this is two thousand six and I think Squarespace was still just you, right? Yeah, so I had at some point along the way a part time Towards the end of this somebody who was doing part time customer support and then I had contracted out um somebody to do some of the helping me with the template designs, but there were no no full time employees, no. And and was your office your room in your apartment? It was. And were your roommates at the time, like were they just thinking, Oh, that's Anthony, he's like doing this internet thing. Yeah, they had no clue of what they were like. I mean'cause it it's like it's New York, right? And it's New York

ten years ago, this is not like Silicon Valley. They're like What do you do? You make websites, whatever. Anyway, they could kill us. They're like startup, they're like, Oh, you're unemployed. Interesting. That's cool. Ha So let's say in two thousand six you're doing about

two two fifty in revenue a year. Something like that. Which which sounds like a lot of money for a guy in his m early or mid twenties. Were you making a lot of money? Was there a lot of profit or was it just I I would put it one hundred percent back in as much as I could. If I

made twenty bucks on AdWords, I put twenty bucks back in AdWords. If I made a thousand bucks on AdWords, I'd spend a thousand more bucks on AdWords. If I spent you know I keep a little bit of a balance in case I needed it for something, but I would just put Almost all of it back in. And Yeah, I mean I didn't have a problem paying my rent. Yeah. I was going out with other people my age, so it wasn't like Yeah, you weren't going to Michelin three star restaurants. No, no. I couldn't even find someone to go with me if I wanted to. And um

At some point. I forget exactly when, but I ended up being like okay, I should I should have an office. Just to split up Work day. And not work day. And so I remember being like, Okay, well, let's see. And so of course go back to Craigslist where apparently

Everything is. And um I rented a desk from this architect. Down in um West Broadway and Beach, so it's like try back. But you were still doing most everything. Like you were the you were the CTO, the CEO, you were designing stuff, you were for a while. Uh and and how did you cope with that? Was that was it exciting, was it amazing, or were you stressed out or what? I think it took me years to fully appreciate

What the stress was really doing to me. You know at some Point in this, two things happened. One. I stop making progress.

I would set these minor goals for myself, like simple things, like okay, I want this feature out in a month. And then you know the end of the month. It's like nah, I just I ran AdWords, I paid my taxes, and like, you know, I answer customers like wow, I didn't actually get anywhere. And so I started to be like, Okay, this isn't gonna work. Two. Start to sort of like

Have Yeah, it was like panic attacks. You know, and I didn't know what that was or where that's from, or I had never experienced that in my life before. Like like heart palpitations and just just Yeah. Yeah. Hearts racing. Your throat's closing up, you can't breathe. It basically feels like you're having a heart attack. Or what you think in your mind to be a heart attack.

Do you remember what would trigger those? You know, here's the funny thing, and it's why I said that I didn't really appreciate what it was doing to me. It was almost nothing would trigger it. You just be kinda there and you start to get in your head and start to focus on it and start to get stressed and you know, yes, it was stressful in the moments where the server would crash or something and my heart would be racing, but but that's not a panic attack. Panic attacks like you're just sitting there at like two PM in your room. Hanging out. Mm. And your heart's racing.

You don't know why. But but what was stressing you out? What do you remember what Yeah. Trying to do it alone for a while. The infrastructure side of stuff, I can't really like explain to you how stressful this was because eventually after this thing crashed a bunch.

You set up monitoring, and the monitoring Checks it. And if it crashes, or there's a performance problem, or whatever. It would send a message to my phone. And so it would happen in the middle of the night.

It would happen. if I'm out to dinner and you never know what's wrong with it. So it's always like the psychological Here you go. Figure it out. Figure out why it's broke. Like and there's no one else who can save you. Cause no one else knows,'cause you wrote the whole thing, so

Go for it. It was like in a way I was really free because I was in New York and I had control over my schedule and and all those and I didn't have any employees and I could they cut it was a self service thing. In the other hand I'm completely and totally trapped. And we come back in just a moment. How Anthony started to bring other people on board to help out.

and then realize that letting go of control? was a lot harder than he thought. Stay with us, I'm Guy Raz, and you're listening to How I Built This. From NPR. Hey, welcome back to how I built this from NPR. So it's around 2006, and things are going pretty well for Anthony Casalina.

At least on the business side. But Personally? It's not so great. He's running Squarespace almost entirely by himself. And he's really stressed out.

Squarespace is totally consuming his life. He even refuses to travel by plane because he's afraid the servers might crash while he's in the air. And so one day Someone suggests that Anthony seek out some business advice. Yeah, I converse with a lot of customers over um chat and people writing the support and stuff like that.

And there was a point where um I was having a lot a lot of chats with this one customer and Yeah, he's like Hey, I'll introduce you to somebody who um is business guy and will help you uh You should talk to him for advice. And so I ended up talking to this guy for a while, his name is Dane.

His name is Dane Atkinson, I think, right? That's right. And it was like, hey, you know, you're really good, Anthony, at Engineering design, all these things that you Have done up to this point, you know, and and and or somewhat successful at, right? I mean this is not Squarespace is a good story up to this point, not you know, not a bad one. Sure. But you haven't been great at hiring. You know, you haven't hired anybody or any of that. You're not good at business.

Yeah, well I mean some parts of business I would say.'Cause I mean this is a Yeah, it's funny, I look back at Squarespace at the time and it's like this was a really successful project. This was not a really successful company, even though it really looked like a company, right? And he said, Okay, you know, let's join up and I'll be the CEO. And you be the founder, everything else, it'll be great. And you know, I'm gonna bring over one of my friends who's an engineer and let's start hiring people and start doing this. Well just Baster was like who who was

Dane, like what was his background? Wha how did he Convince you to do this. Well, I mean he was somebody who had He had started a couple companies in New York. I I'm kinda I'm blanking on some of them, but he was a guy who old older than you two?

Yeah, um Maybe like twelve, fifteen years older than me, something like that. Right. So so more experienced in the in sort of the running businesses. Yeah. Yeah. How how were you gonna pay him? Was there enough revenue coming in where you were like okay, yeah, I could I could pay you a salary? Yeah, totally. You know, Squarespace always had enough money to um

Yeah, we always had enough money to pay people's salaries. That kinda wasn't an issue. So he came aboard as your CEO and and and I Presumably the goal is to to grow Squarespace. Yeah, and I you know, uh for me at the time I didn't know what it meant to

have a certain title or not have a certain title. I was just like, look, this is fluid, easy. Okay, cool. I'm still running this show here. Like I, you know, I'll just take this risk. And over the next Couple of years we moved into an office on Center Street in Soho. And you know, we started adding people to the company. And frankly, some A lot actually joined very organically. We had um

Some people join in creative roles who were customers actually. Some moved to New York. You know, we had a guy join and help m you know. Two people help with the infrastructure. And did that instantly free you up? Did that take some of the pressure off? Honestly.

There's more people there. So I I am at least not like alone and in my head. And that released some stress, but I I think it probably created more stress for me. Then I realized because I didn't fulciate

What I was doing, what I I think you gotta imagine. I'm twenty what? Four, five, six, I've never hired a single person in my entire life. And I'd say that, you know, through this process I

I learned a lot about myself and I learned a lot about A lot about dealing with people in a company. And I learned a lot of lessons really the hard way. Yeah. By literally making I think pretty much every possible mistake. Um one can make. So here's what I'm curious about.

You start this thing in your dorm room. It's you. You're the engineer, you're the CEO, you're the marketing guy, you're the you're you're the everything. Yeah. All of a sudden you team up with somebody who has some business experience. who has a plan and says look

We need to start hiring people, we need to expand, which is exciting. Yeah. But you would have to give up some control over the day to day running of this thing, which I can imagine was probably not easy. Yeah, and it didn't work for me. Was there friction between you and Dane? Oh yeah, of course.

Which is very normal. I mean this happens All the time. in startups. Right. This is a a story we've heard on the show before. Sure. Um He was there for five years and then he he he left and to start his own company. But during that five year period was it Really difficult for you to

A line what your visions were? Did you just kind of Plow through that five year period or or was it actually okay? It wasn't really okay. I think um

You know, look, I was young, right? And I think that people had A good intent back then. And I didn't know what I was getting into. I didn't even know what a good manager looked like. I didn't know how much stress I was supposed to have or not have. I didn't know what kind of dialogue were good or bad, like what dysfunction looked like. What you know, I didn't know that stuff. And so I was in this mode of like keep it all together. Just keep it together. Don't let it fall apart. Don't go back to zero people. Like don't Just keep it together.

And try and find a way through this. And that was a lot of what I was uh what I was thinking about. Mm. So okay, let's just get back to the actual. website publishing side of things for a sec. Um

'Cause I mean, Dane's there, Squarespace is growing. This is like w the the late two thousands. Yeah. Yeah. Like so so what's happening on the on the product side? So The product of Squarespace is always

been one of the primary growth drivers. And um A lot of good things happened at the time. I mean, we expanded our advertising channels. Adding more people meant that I wasn't in this mode anymore where I was sort of um

just constantly like not hitting any goals. And so You know, around um I'm recalling this now. Here's how this happened. So

We launched Squarespace five. Which was a huge, huge update to the platform. I mean the years like I say oh seven, oh eight, something like that. Animations and things on a website and web apps. Yes. Like we're entering into a different era. And launching Squarespace Five was, you know, one of the things that helped propel us forward. And I I would say this. It was a total disaster. We flipped it on for everyone at once. It had these really hard to track down bugs.

We're literally working twenty four seven overnight. Every single person was doing customer support,'cause it was just crashing and crashing and we couldn't roll it back. And um You know, I think that we finally got through it and we kept growing up.

And at the time You know, we had a couple of people in marketing, we had more people in product, we had more people in engineering, we had eighty five thousand customers or so. Ten million dollar run rate. And at some point We were approached.

To to sell the company. And Yeah, so we got approached by Getty Images. And um you know, Getty sells You know, stock photo. Stock photo, stock video, stock audio, et cetera. And one of their ideas was well, a lot of these images end up going onto websites. Why don't we sell stock websites too? You know, there's this little company in New York that seems to be doing a pretty job, so they ended up coming and talking With me.

And You know, I don't come from like massive amount of money or anything like that and like You know? And I I had never started Squarespace to sell it, like that wasn't the point.

I I was having a good time growing it. We were making an impact on the web, and somebody shows up with an not insignificant um offer to buy the company. Sure. And that would have been a really big thing. I I I really uh I struggled with it. So

So what'd you do? Um Around the same time. I was also approached, I don't even know how they like caught wind of this, but like with some investors saying, Hey, you don't have to do that. You don't have to sell it all.

If you want some liquidity, why don't you accept an investment from us? We'll put some money into the company, you can sell some of your shares to us, uh, you can keep running it, we'll put a board in place, we'll help you recruit executives and all that. And I um I like that. And if if the the acquisition off did anything, it it caused me to go down that track. And realize I wanna keep doing this. I wanna keep running it.

I want to sell some of my shares in the company. I want a real board in place. I want different kinds of accountability and I want a different kind of team. Um So we closed An investment from Index Excel. in July of twenty ten. This is these are uh two investment firms, Index Ventures and NXL partners and and

They invest right. I read What, like thirty eight million dollars? Yep, thirty eight point five. Wow. And I think that

That was the one of the catalysts for me kind of kicking off that era of Squarespace. Right. After this investment. We started looking at the product and I remember this moment with um Being there with one of my main product people and we were looking at the sites that are being created on the platform. And all the business metrics were kind of fine.

But Not growing as well as, you know, n you know, we we had and we were starting to tap out on a couple different Ad channels where you reach kind of exhaustion, right? You can't just keep spending and not hit a point of diminishing returns. But Um

I mean the web was changing. There were the the iPhone had come out, and and so people were more used to saying, okay, the web experience on my phone, while different, needs to be very high fidelity. And this thing this thing that we had, Squarespace five. Yeah, it wasn't gonna It wasn't gonna do it. I mean it's it these look like blogs, they've got sidebars, this don't even work on phones. What is this?

And so Me and a a couple of people started to rewrite all of Squarespace. Like the whole thing. Wow. This is in this is in two thousand eleven. twenty ten.

And so we start to work on squarespace six. And scorespace six. And look, if anyone knows what it sounds like when I'm like, Oh, we'll just rewrite the thing, like that's probably the worst thing you can do. You never want to be in a situation where you're rewriting the core of your platform. It always takes three times longer than you would expect. you know, the people who originally wrote it are sometimes no longer there. And it's usually a disaster.

But Yeah, I wanted to take another shot at this. That was the point of the investment. The point of the investment was we're not done. We know we can make something better. And so over two years Um a small group of people.

made Squarespace six. Which Really the vision was, you know, we want to be able to create any kind of website. Um I'm trying to imagine this, like You resumed the role of CEO after Dane left, I think in around two thousand eleven, is that right? End of twenty ten. Twenty ten. Um you are leading the re Architecting. Like complete re architecture of this thing. Yeah, I'm I'm coding. How are you coding and also trying to like 'Cause you're a good coder, obviously, were you able to also be a good CEO?

I think I was in a mode where I knew I didn't have the right kind of support around me. And I think during this time, I started realizing what a horrible manager I was. You know, after this investment, it was maybe a maybe a year after.

And I ended up meeting our um our first VP of engineering guy named John Colton. Great. And I was trying to code and run the engineering team and I had all these like you know weird relationships and like he just like immediately Took

such a massive amount of stress away from me with respect to How to be a manager, how to do one on one, how to remove roblocks from people. Yeah. Like he just like I just learned so much. I mean because again, I I've never worked anywhere else, really. It it sounds, Anthony, like you I mean'cause you are growing up. with this company. I mean you were a kid, you know we mature like you you know, we're we're all different versions of ourselves as we get older. Like me at thirty and me at twenty are very different from who I am today.

Um And it sounds like you You started to kind of Realize this. Were you okay with criticism and feedback or did you would you get defensive?

Um One of the things that happened a long time ago in Squarespace when doing a lot of customer support and doing it all alone is like Whether you'd like the feedback or not, you're about to get a lot of it. Right. I mean people cursing me out, saying I'm an idiot. I asked and put my manager on the line, even though I'm the only person in the company. Um you know, like uh

And and literally leaving and being like, I'm done with you, this product sucks. Uh and so over over the years, I think I I developed some amount of realization that I need to create an environment where I hear feedback and I don't always have to agree with it. But to create an environment where you don't hear it is really the scariest thing for me. Because I think that

If you remain closed off to it, you become Vulnerable to these big like seismic shifts where you just you just ignored something to the point where something's really gonna break. So I I'm more about trying to listen to what's there and figure out what I can figure out from it because

Look. At the end of the day, I've made so many mistakes. It would be so silly. For me to sit there and and think that I'm not making any now. I Have to be. Um, hopefully I'm just more attuned to it and I'm faster at resolving things.

What what I mean, it sounds like the turning point was when this new team started to come, you started to rewrite the software, but the visibility of square space also changed. Like you guys You guys had a pretty um interesting strategy which was to advertise on podcasts. You've advertised on ours, w full disclosure.

And and people weren't really doing that in two thousand ten. Yeah, so we did it even before twenty ten. I mean podcast was yeah, I remember Um, you know, we were gonna we're gonna maybe try a podcast ad. The first podcast we did was this week in tech. And uh I mean it costs like something like thirty grand. I'm like, that's our whole AdWords budget. For like the whole month.

In how many podcast reads and what's the audience and are you sure? Like I don't know. But you know what, at the end of the day Let's try. And it immediately worked for us. You saw traction right away? Right away. Right away. Wow. You could do there's this really authentic thing around like you are supporting a show host. That show host

has a connection with their audience. You are supporting the creation of that content and you would never hide the fact that it's sponsored. But you know, people generally were like, okay, I'm in boy with this. I love podcasts. I love this show. Thank you, Squarespace, for doing this. And I think that It was a it was a really great thing for us. There was a point where it seemed like every podcast was sponsored by Squarespace. We tried. We really tried. Um later on there was it was a joke when we first did our our Super Bowl ad Somebody was tweeting, they were like, I didn't know the Super Bowl was a podcast. Um so yeah, I mean we we went in this space and it you know, it was great because I mean it's something like related to what we do, right? Squarespace supports lots and lots and lots of independent creators and I think a lot of podcasters

were independent creators and they had, you know, voices and And show concepts that otherwise wouldn't have, you know, existed if it wasn't for that medium. So it's really Amazing to be able to support it. Um the way we did. Um as you sort of began to turn a corner.

Did the growth just come from, you know, a combination of more outside capital and the ability to market your brand more? Is that was that the game changer for you? The outside capital Is not it. Main driver for it was Squarespace six.

Launching. And that changed for us. So this is in like twenty twelve, July. Version six of Squarespace. Version six of Squarespace is the one that you know Small team couple of years after this investment. This is the one that you can use today, right?

Is yeah, this is the one that's online today. It's technically seven, but it's not a big The version difference is not as big. And it changed all of our metrics. You know, you you had all these crazy beautiful sites you could do. The portfolio sites with full screen images, you could use those for businesses.

The sites were It was some of the first sites that work perfectly on mobile phones without any adjustments, right? And so that was a big deal. Um Without that product, Squarespace wouldn't be here. I I'm curious, how did you I mean, you started this in two thousand

three, right in your dorm room. And there was really nothing. Like it out there. Today there's a lot of competition, right? I mean, this is much more complex world than it was when you when you first had Squarespace out in the world. Yeah. Yeah. Well i in a way what's funny is it's it's almost uh

Less fragmented. And you know, I don't know if you could grow a business on AdWords the same way I did fifteen years ago. Cause I I think people look for they look for the brand now. It's definitely a different landscape. And also when you've got companies like us that have had such an investment over such a long period of time in this space, it it's really as we've grown the ambition of the company is scaled. You know, it started with can Anthony make a website for himself to You know, can we make blogs and these other kinds of websites too, you know, the kinds of sites you can create on Squarespace Six and then, you know, we launched a commerce platform later, so can you sell on Squarespace? And there's a lot of people selling on Squarespace. And you know, we're just really centered around entrepreneurial success right now. Can you put the site online you want? Can

We help you be successful in marketing yourself and starting a business, and that's really the core of what Squarespace is about. Mm. You now have this huge platform, right? Yeah. And it means that with that comes like responsibilities that you probably never even imagine, power that you probably never even imagined or wanted.

Sure. controversy I think last year where some like white supremacists were using Square space and Іно, іргана фіз аллитай. Yep. How do you do you weigh each each each situation? Like how do you

You know, like what do you do? Yeah, well y you try and have rules around it, and so One thing that's great about Squarespace, frankly, versus other um You know, situations other providers are in.

Is that It's a paid service. So we actually avoid the worst of this, right? Very rarely is somebody like, I'm gonna post a bunch of bad stuff online, so here's my credit card and here's my address and I'm gonna post it. You know what I mean? Like We're very lucky in that regard. So You know, our stance, like everyone else's stance, has to evolve on this as as as time goes on, because

Yeah, we are a business. We're not the government and we're not, you know trying to protect every possible viewpoint on the planet. And so, uh Yeah, we need to make sure that You know, we're doing business with the right

You know, the kinds of people we need to do business with. Um, I think at the end of twenty seventeen Squarespace raised two hundred million dollars in funding. Valuing the company at one point seven billion might be valued higher now. Um, that's a lot of money. I mean you you were

you know, your tech success and you do these conferences and you're on these shows and You know, you you're worth a lot of money. But You are also Does it also make it challenging?

to you know to make f new friends and to meet new people because you never know if people just want to be around you for that reason. You know, I'm really lucky in life that I've always been the kind of person that I've made good friends that have Kinda gone. through a lot with me and I I know kinda what that

What that looks like when it's, you know, non superficial. And Yeah, I I still have a lot of friends from like from that that original apartment in New York. I think that's been a really positive part of my life actually have we stay in touch and um Yeah, look, you get older and context changes. So it it it it is harder it becomes harder to meet new people. Sure. I mean when you're when you're twenty three, twenty four and you got your random roommates and you have a bunch of time and you have your school friends or whatever, like yeah, people are more up and now more people are

Uh in kind of family modes and everything else, but Do you ever think that you wanna you wanna do that? I mean have family? It's a great question. I um I've really put off thinking about that. Um yeah, I mean just so much has changed in my life so rapidly. I I've just really been focused on all of that. I mean I'm not ruling it out. I just uh it's not front and center right now.

But you know. The things that are front and center of my mind at twenty five and thirty five and fifteen are different. Yeah. So And I hope I don't sound like your mom. Like well, when are you gonna have grandchildren? They do that. They do that. Don't don't don't don't worry, that voice is there. Anthony, obviously you're you know, you were like

super talented coder, programmer. from a young age and have a lot of talent. But how much how much of your success do you think is because of that talent and your skill and your intelligence, and how much of it do you think is because you just got lucky too? Oh man, I have been lucky so many times in my life.

I'm lucky my my parents had a computer around me when I was a kid, right? Um you know, I'm lucky the data didn't get deleted the wrong you know all these scenarios. I mean, you know, we're we're just even scratching the surface of the uh the crazy things that have happened. I mean Um I'd say that There

qualities I probably have that have helped me stay here around, you know, perseverance and pain tolerance and Um and uh the I guess some level of adaptability. Um my best moments some kind of self awareness. But No, I think that anyone who possibly claims that They didn't get lucky's crazy.

It's Anthony Casalina. Food of Squarespace. Last year there was speculation Anthony would take the company public, but for now. Squarespace has decided to stay private.

Meanwhile, Anthony still keeps a vast collection of Magic the Gathering card that he bought when he was a kid. He says he's got hundreds of them sitting in binders in a storage space, including the rare Black Lotus card. said to be worth more than$20,000. Hey, thanks so much for sticking around, because it's time now for how you built that. And today's story starts in 2016, right outside of Boston, with Kate Westerveld Waddling around Target. Waddling around Target because she'd just been released from the hospital where she'd given to a nine and a half pound baby boy. So Kate was sore and she had stitches and She wasn't really up for a target run. Now the thing you should know about Kate is that she's kind of a planner, so she'd already fulstocked her nursery with everything she thought the baby would need.

diapers and wipes and clothing, but she didn't really give much thought to the things that she might need after her baby was born. The nurses walked in with things like mesh underwear and these ginormous pads. Plus ice packs and a squeeze bottle to help keep her stitches clean. all stuff she needed for her recovery. But stuff Kate didn't have at home. So on the way home from the hospital, while her husband and new baby waited in the car, She went shopping and she felt Kind of clueless.

I got A bunch of different breastfeeding aids, you know, organic pads, synthetic pads, whatever I could get my hands on, because I was just desperate and in dire need of any help and all help and I knew I wouldn't be able to get to the store again in the next couple days. Kate left the store totally overwhelmed, but she also left. with an idea. We live in a convenience economy. We get razors delivered, groceries delivered, everything is delivered. How are we not providing this convenience for new moms who need it the most? And as soon as she got back in the car.

Kate thought, I'm gonna go build this thing. And by this thing She meant a box filled with products a new mom would need. A box delivered right to her door. She kept thinking about this idea during her leave. So after she went back to her 9 to 5 job, Kate decided to start working on it at night.

After her baby went to sleep. I would order various products and then I would test them all. Kate tried more than 400 products over the course of a year. And eventually, she settled on a set of 10 items to go into her first boxes. She sent them to friends and family, and she asked them for feedback. And the one product her test moms really liked?

an ice pack. At the hospital they give you just bags of ice and they sort of stick them in your underwear and say good luck. So Kate found the perfect ice pack sized and shaped so new moms could walk around. But there were some women who told her, you know, this ice pack is great. Fuck! I ended up with a C-section and what I really needed was a heating pad to place on my belly or some sort of oil for my scar and my incision line. So Kate decided, hey, maybe I should curate a C-section recovery box. She went on to put up a website and build a social media following on Facebook and Instagram. We know moms are really viral. 60% of mom's mom source across the internet, and so moms started to talk about this box. And in January of 2018, nearly two years after her frustrating target run,

Kate sold her first box. It was designed to look just like a present. It's pink and glossy and we sort of thought, you know, let's put a handle on this box because it makes it feel like a special arrival, like a special trunk filled with self-care items. Kate decided to jump fully into this venture, so she quit her job. launched a company and in her first year she sold almost 500 boxes, all assembled and packed in a room above her garage. Kate Westerveld's business is called Mombox, and if you want to find out more about it or hear previous episodes, head to our podcast page, howibuilthis.npr.org. And of course, if you want to tell us your story, please visit build.npr.org.

And thanks so much for listening to the show this week. You can subscribe wherever you get your podcasts, and while you're there, please do give us a review. You can also write to us at hibtnpr.org and if you want to send a tweet. It's at how I built this. Our show was produced this week by Casey Herman, with music composed by Ramteen Arablui. Thanks to Julia Carney, JC Howard, Nor Kutsi, Neva Grant, Melissa Gray, Sanaz Meshkinpur, and Jeff Rogers. Our intern is Candice Lim.

I'm Guy Raz and you've been listening to How I Built This From NPR.

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