How I Built This with Guy Raz - Squarespace: Anthony Casalena

Episode Date: March 4, 2019

Like many classic technology stories, Squarespace started in a college dorm room. In 2003, 21-year-old Anthony Casalena created a website-building tool for himself. But after hearing some positive feedback from friends, he decided to put the tool online and start a business. For years, Anthony ran Squarespace almost entirely on his own but the stress took a toll and he reached the limits of what he could accomplish by himself. The journey to hiring a staff and scaling the company had its own set of growing pains for Anthony, including difficulty letting go of control, and learning how to manage other people. Today, Squarespace has grown to more than 800 employees, and valued at $1.7 billion. PLUS in our postscript "How You Built That," how Kate Westervelt took an overwhelming experience and turned it into a gift box for new moms – filled with essential items women need to recover from childbirth. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This podcast is brought to you by Squarespace. I talk to entrepreneurs all the time who are looking for a way to upgrade their digital footprint. Well, whether you're just starting out or you're scaling your business, Squarespace is the easiest way to build a great website that stands out. It's an all-in-one website platform that gives you everything you need to claim your domain, showcase your products, and get paid. Anyone can use Squarespace's cutting-edge design tools to build an online presence that truly reflects what makes your business special.

There are templates, intuitive drag-and-drop editing, and even an AI-enhanced website builder. Then, Squarespace's built-in analytics tools help you make smarter business decisions. Review website traffic, learn where to focus engagement, and track revenue all in one place. Looking to grow your business, Squarespace even offers fast, easy business financing

through Squarespace capital. Go to Squarespace.com slash built for a free trial. And when you're ready to launch, use offer code built to save 10% off your first purchase of a website or domain. Loans issued by Celtic Bank and serviced by Stripe, all loans subject to credit approval. This show is in partnership with Airbnb. This past summer, I took my family to Vienna, and it was incredible. We spent our days wandering the old streets, stopping for coffee and pastries, visiting museums, and just soaking up the history of one of the most beautiful cities in the world. And one of the things that made the trip so special was the home we booked on Airbnb. It had tall windows, beautiful old details, and plenty of space for all of us. And being in that home on Airbnb, right in the middle of Vienna,

walking distance from so much of the city, made it feel less like a visit and more like we were actually living there. Plus, taking a trip is the perfect time to host your space on Airbnb. your place with all of its personal touches and its amazing location could make someone else's vacation even better. Your home might be worth more than you think. Find out how much at Airbnb.ca.com slash host. Somewhere along the way, I get like a call on my cell phone from like a customer. Guys like, hey, is Squarespace okay? So I call the data center. I'm like, hey, can you reboot this server? And it doesn't come back. And it wasn't coming back.

Completely crashed. Wow. And I was like, I got to go to New York right now. And I just drive to New York. And I'm like having a panic attack the whole way up because I'm like, it's screwed. I lost all the data. It's all gone. That little experiment's over.

From NPR, it's how I built this. A show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz. And on today's show, how Anthony Casalena's dorm room coding project grew up and turned into Squarespace. and how 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, to 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 Costellena wanted to solve. Now, before I go on, I'm going to 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 be able to be able to solve. you will hear is pretty great. Anthony Cussolena literally created his product in a dorm room at the University of Maryland in 2003. 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 Squarespace. 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 dad always had computers around, so I would break those and incur the wrath of my parents. And eventually I got to a point where they were sick of me breaking their computers and ended up buying me or getting one that I could break myself, which I, you know, learned how to load games on to and learned a little bit of basic and stuff like that. And this was like the area of like,

you know, 286s, 386s, DOS, Windows 3.1, Windows 95, that kind of era. But I was always really, really into that. So you started to learn how to program basically as a kid. Like, how old were you? Probably 13, 14. Because when I was 15, I worked for an 80. internet company in Maryland, in Baltimore, actually. They were trying to actually recruit my dad. And, you know, my dad was like, I'm busy. I'm employed, et cetera. But, you know, my son's a good programmer. You should talk to him. Just to put this in the right timeframe, we're talking about the mid-90s. I think you're talking about the mid-90s. I mean, the web was really new. I mean, it wasn't like a common thing. And I kind of gravitated towards this thing called Internet relay chat.

So it's like this global chat room you can kind of go into. And it was like the wild west of the internet. Like you were connected to this network. And, you know, I remember somebody earliest programming I did was programming scripts that go into the IRC client that would control it and give it new functionality and things like that. And I also was around people who knew Windows programming. And I was obsessed with user interfaces. And I learned a lot of Windows programming because I just wanted to know. how it all worked. I mean, it's really cool. I don't know why I was so fascinated by all that,

but I was definitely into it. So you, I guess you decide when it's time to go to college, you went to the University of Maryland. Yeah. And you are studying computer science. And at that time, like people are starting to blog and build websites. And I guess you wanted to do one for yourself. Yeah, this was like 2003. And in 2003, 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 you would have to put together to make what you would normally think of as a website right now, right? So you have blogging software, but that's separate than page building software, right? That was, like, at the time, Dreamweaver and front page and all that.

And then you had separate software that would, like, tell you who's visiting the website. It would be, like, stat counter or something, like, one of these really old things. And then you have to go and upload that somewhere and host that somewhere. And there was like these old hosting services that you would use. And I just didn't, I didn't want this mishmash of things. And the other thing that I was really into is, you know, I was just always into the way it looked, the way the interface worked. And I knew that people were going to find this was going to be like my, how they see me online. And so I wanted that to be good.

So you wanted to create a blog and a website. You could have done that, right? Like there was live journal and on Geo City. I didn't even remember. But there were. Yeah, yeah, yeah, that kind of, there was type pad, movable type. Yeah, it was pretty easy to create a blog, even in 2003, right? Well, not really.

No. I think that there was live journal, but that wasn't a very, I mean, my site was like half professional, right? And so you didn't put your professional site on live journal. And it was a blogger at the time, which again, they were very personal in nature. But I wanted more than just a blog. I wanted, you know, 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 make this stuff.

Let me try to figure this out. Yeah. And so I started making it for myself. And I would show people it, right? I mean, they would be like, check this thing automated. It's a blogging software. And I can make a website with it too. Isn't that cool?

And I remember one of my friends being like, I'll give you 200 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, you know, it pretty quickly evolved into this could be a business. Was the idea from the beginning to make it easy to build a website? Was that what you were thinking when you were creating the software? So it was always about publishing. I wasn't going to 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, do-it-yourself wave, where people who would have otherwise been a little intimidated, you know, it was this kind of like, oh, I can do this too, but then giving them something more powerful, saying, look, you can publish a blog post, you can publish a page, you can publish a photo gallery, 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, was 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've got that. I'm looking at you. You're like 20. 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 was in a, let me say, how many bedrooms was it? One, two, three, four, four bedrooms. You know, it's tiny. It's like a single bed. And there's my little desk in front of it. And I have, you know, I'm two 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. Yeah. And how long did it take you to actually build this architecture? So the original version of it, I started programming it in 2003, April, 2003, a little bit before that. And it took me until November, December, I was kind of like done and ready to launch it.

So let's say eight months. And did you have 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 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. 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 servers. So I went to my, I went to my parents who, you know, I don't know how I calculate it. I needed $30,000.

And you need $30,000 to get this. $30,000 to get this off the ground. I needed these servers. I needed two of them, right? Because, well, if one crashes, I needed a redundant one, right? I worked at this, you know, tech company was in high school, and I know that these things crash. And so I remember asking my dad for it. And it was a fight.

I remember parking, I was at the University of Maryland, I was in the stupid parking lot outside of the dorm. And I remember being on my phone. And, you know, it was like, why do you need two? Why can't you have one? Why isn't, you know, that would be half. Like, I mean, it was a, it was a fight. And, you know, they eventually, I eventually won that fight.

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

So 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 for some reason just thought, like, okay, square space, like monitors were more square at the time. They weren't as rectangular. Like, it's kind of your space online. I guess that works. And, you know, I can probably draw the logo for this. I'm probably going to pick like a square or something like that.

But, yeah, I mean, that's kind of where it started. So if I ran into junior year of college at University of Maryland, I was like, hey, Anthony, what's going on? You're like, oh, I'm just working on this business. And I would say, well, what's the business? What would you say? How would you describe it? I called it a publishing system. I said, you know, it was a way to make websites and blogs.

And I probably would lean more into blogging back then because it was more topical. And people were like, what's that interesting? You know, and again, it meant that DIY thing was possible. Yeah, and I said it's a way for people to make websites. And so when you launched it in 2004, like, you just, I don't know, hit a button and then it just like, here it is, here's Squarespace. So I won the fight with my parents on the 30 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 in the data center. These are not, like, normal computers. They're, like, really flat, really long and really, really loud. And so they were so loud that I'd have to keep them off because otherwise just is 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, Joel Spolsky. And 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, peer one sounds good. They like Joel. And so I visited New York as a kid. And there's just something about it that I just knew I just knew I wanted to be there eventually. And so I drove them up in my car, plugged everything in, and turned them on, checked that I could remotely connect to them. And, you know, went and had dinner in New York and then drove back to Maryland. So when you launched Squarespace, like from the perspective of a customer, it was just a website that people would find? Right. So when I turned it on and I was like, well, how am I going to get people to show up?

Like, I guess you can do advertising. And so I bought a bunch of Google AdWords. Well, not a bunch. I bought like 200 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 might have been like three. Like, I mean, we're talking like not a lot of signups or like 10. By the way, what did it cost to sign up for Squarespace in those first few months? Do you remember? So, little in 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. We still have a free trial. But back then, I actually had a free plan. And the idea, you know, 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. Or MySpace, whatever. Like, people would be like, you give it away for free and then people are going to upgrade. And so in the first year, I realized. that there were a lot of people who were going to use this thing for free

that were never, ever, ever going to upgrade. And again, I'm running this, like, I don't have, 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 going to upgrade using up all the server space. And it was really not the point of the thing.

It was not out there trying to make the next live journal or blogger. I wanted the, let me focus on the people that want to pay for this. And I forget what it costs the time. Between five and $15 a month. you know, really inexpensive. So did you, I mean, in that, in 2004, that first year, I mean, you were still a student and running this thing.

And what did that mean? Like, how, 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 $50 grand a year. My parents were like, where are you going to get a job after college? That's a nice little side project. But where's your job? And 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 going to try and grow this. And so I actually stayed on, instead of graduating in four years, I waited and graduated in five and kind of took some, like, let's just say pretty light workload classes on that fifth year. I was buying myself time, right?

I was buying myself out of, like, my parents really getting on my case about getting a job because of that I got a pass. I mean, I think that they 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, 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 we drive to Miami, which is like a 17-dollar drive.

Somewhere along the way. I get like a call on my cell phone from a customer. And a guy's like, hey, is Squarespace okay? And I'm like, I don't know. I'm like driving to Miami. And I just told my friend, I'm like, take me to an internet cafe or something, right? Because this is ridiculous. I mean, this is 2004.

This is a different world of internet. And I like log on and like remotely log in 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 yeah, it was a little foreshadowing of what would then happen to me later. In your, you graduated from college in 2000. And by the time you graduated college, I've read that you guys had like about 10,000 accounts and, you know, it's starting to look pretty good. But you were the only person, right? You were the engineer and designer and support rep and CEO.

Yeah, I was kind of everything. I mean, so in the first year, I think we were like a run rate of like 50 grand. And in the second year, I think we were at a run rate of like 200 grand. You know, it wasn't like a million bucks overnight. But in year two, I was able to convince my parents that, you know, I'm going to 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.

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 a 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 in my dorm room. And so at some point, this happened again. Things blacked out. Somebody's like, 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, you know, my girlfriend at the time. And I was like, I got to go to New York right now. And so within 15 minutes, we just got the car, put the server in the backseat. 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 it's all gone that little experiment's over like I should have had the other thing there replicated all the stuff and 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 computers and taking all the drives out of one I'm slotting them into the other and turning the thing back on

and it turned on and everything was fine so after college you decide to to move to New York, obviously closer to the servers to the data center. And it sounds like you just wanted to live there, too. Yeah. So how did you find a place?

So I went to Craigslist. Yeah, I didn't know anyone in the city. And so I didn't want to 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 I had this old. BMW at the time this Black 3 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 23rd Street and got a ticket. And then the second thing that happened to me was I parked kind of in front of my place and like, okay, I guess I have to be double parked like there's nothing else to do. But I'm going to 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 floor, and it was getting a little bit dark, and I was like, take a minute, because this is just exhausting. And I go down, my car's towed. So it's like, I'm just piled with tickets in no car, and I remember being like, going back up to my room and realizing, like, I don't even have a

light in this room. Like, just no lamp. This is 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 went back to Philadelphia and returned to New York the next day, bought myself a lamp, bought myself a bed. And I went on from there. Yeah, this is 2006 and I think Squarespace was still just you, right? Yeah. So I had at some point along the way a part-time, this was the end of this, somebody who was doing part-time.

customer support, and then I had contracted out somebody to do some of the helping me with the template designs, but there were no full-time employees, no. 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 did like, I mean, because it's like, it's New York, right? And it's New York 10 years ago. This is not like Silicon Valley. They're like, what do you do? You make websites? It's whatever. Anyway, they couldn't kill us. They're like startup. They're like, oh, you're unemployed. Interesting. That's cool. So let's say in 2006 you're doing about $2.250 in revenue a year.

Something like that. Which sounds like a lot of money for a guy in his early or mid-20s. Were you making a lot of money? Was there a lot of profit? Or was it just were your expenses? I would put it 100% back in as much as I could. If I made 20 bucks on AdWords, I put 20 bucks back in AdWords. If I made $1,000 bucks on Edwards, I'd send $1,000 more bucks on Edwards. If I spent, you know, I'd 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 at some point, I forget exactly when. But I ended up being like, okay, I should have an office. Just to split up workday 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 I rented a desk from this architect down in West Broadway and Beach. So it's like Tribeca. But you were still doing most everything. Like you were the CTO, the CEO, you were designing stuff. Yep, for a while. And how did you cope with 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 stopped 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, at the end of the month, it's like, no, I just, I ran AdWords. I paid my taxes and, like, you know, I answer customers to what, and they think, wow, I didn't actually get anywhere. And so I started to be like, okay, this isn't going to work. And two, I started to sort of like have, you know, 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 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'd just be kind of 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 that's not a panic attack. Panic attack is like you're just sitting there at like 2 p.m. in your room hanging out and your heart's racing.

You don't know why. But what was stressing you out? What do you remember the things that would stress you out? Yeah, I think that trying to do it a little. loan for a while, the infrastructure side of itself, 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. And there's no one else who can save you because no one else knows because 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 all those. I didn't have any employees. And it was a self-service thing. In the other hand, I'm completely and totally trapped.

When 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 Casalena, 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. You know, I conversed a lot of customers over chat and people writing the support and stuff like that.

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

all these things that you have done up to this point, you know, and are somewhat successful at, right? I mean, this is not, Squarespace. It's 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. They're not good at business, he was saying. Yeah, well, I mean, some parts of business, I would say.

Because, I mean, this is, you know, 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 going to bring over one of my friends who's an engineer and let's start hiring people and start doing this. Well, just positive, like, who was, Dane? Like, what was his background?

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'm kind of, I'm blanking on some of them, but he was a guy who... Older than you, too? Yeah. Maybe like 12, 15 years older than me, something like that. Right. So more experienced in sort of the running businesses.

Yeah. Yeah. How were you going to pay him? Was there enough revenue coming in where you were like, okay, I could pay you a salary? Yeah, totally. You know, Squarespace always had enough. money to, yeah, we always had enough money to pay people's salaries. That kind of wasn't an issue. So he came aboard as your CEO and presumably the goal is to grow Squarespace.

Yeah. And, you know, 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 we started adding people of the company. And frankly, a lot actually joined very organically. We had some people join in creative roles who were customers, actually. Some moved to New York. You know, we had a guy join and help, 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 am at least not alone and in my head. And that released some stress. But I think it probably created more stress for me than I realized because I didn't fully appreciate what I was doing. You got to imagine, I'm 20, 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, I, I, you know, 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 by literally making, I think, pretty much every possible mistake one can make. 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 everything.

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. 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. This is a story we've heard on the show before. Sure. He was there for five years, and then he left to start his own company. But during that five-year period, was it really difficult for you to align what your visions were? Did you just kind of plow through that five-year period? Or was it actually okay?

It wasn't really okay. I think, 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 dialogues were good or bad, like what this function looked like.

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 thinking about. So, okay, let's just get back to the actual website,

publishing side of things for sec. Because, I mean, Dane's there, Squarespace is growing. This is like the late 2000s? Yeah, yeah. So what's happening on the product side? So the product of Squarespace has always been one of the primary growth drivers. And 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 just constantly. constantly, like, not hitting any goals. And so, you know, around, I'm recalling this now, here's how this happened. So we launched Squarespace 5, which was a huge, huge update to the platform. I mean, the year is like, I'd say, 07, 08, something like that. Animations and things on a website and web apps. Yes.

Like, we're entering into a different era. And launching Squarespace 5 was, you know, one of the things that helped propel us forward. And 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 24-7 overnight. Every single person was doing customer support because it was just crashing and crashing.

And we couldn't roll it back. And, 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 people in marketing. We had more people in product. We had more people in engineering. We had 85,000 customers. or so, $10 million run rate. And at some point, we were approached to sell the company.

And, yeah, so we got approached by Getty images. And, you know, Getty sells, you know. Photos, images, yeah. Stock photos, stock photos, stock video, stock audio, et cetera. And one of their ideas was, well, a lot of these images end up going on to 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 had never started Squarespace to sell it. Like, that wasn't the point. I was having a good time growing up. We were making an impact on the web. And somebody shows up with a not insignificant offer to buy the company. Sure. And that would have been a really big thing for me.

And I really, I struggled with it. So what'd you do? Around the same time, I was also approached, I don't even know how they caught wind of this, but 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.

You can keep running it. We'll put a board in place. We'll help you recruit executives and all that. And I like that. And if the acquisition of not have did anything, it caused me to go down that track and realize, I want to keep doing this. I want to keep running it. I want to sell some of my shows in the company. I want a real board in place.

I want different kinds of accountability and I want a different kind of team. So we closed an investment from Index and Excel in July of 2010. These are two investment firms, Index Ventures and Excel partners, and they invested. I think I read, what, like $38 million? Yep, $38.5. Wow. And I think that that was one of the catalyst 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 being there with one of my main product people, and we were looking at the sites that were being created on the platform. And all the business metrics were kind of fine. But not growing as well as, you know, 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 dimension returns. But, I mean, the web was changing.

There were, the iPhone had come out. 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 5, you know, it wasn't going to do it. I mean, these look like blogs. They've got sidebars. It doesn't even work on phones. What is this? And so me and a couple people started to rewrite all of Squarespace, like the whole thing.

Wow. This is in 2011? 2010. And so we start to work on Squarespace 6. And Squarespace 6, you know, 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, you know, 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, a small group of people made Squarespace 6, which really the vision was, you know, we want to be able to create any kind of website. I'm trying to imagine this.

Like, you resumed the role of CEO after Dane left, I think, in around 2011. Is that right? 10 to 2010. 2010. Yeah. And you are leading the re-architecting. Like complete re-architecture of this thing. Yeah, I'm coding.

How are you coding and also trying to like be a CEO? Were you, because 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 year after, and I ended up meeting our first VP of engineering guy named John Colton, who's 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 roadblocks from people. You know, like, he just, you just, Like, I just learned so much. I mean, because, again, I've never worked anywhere else, really. It sounds, Anthony, like you, I mean, because you were growing up with this company. I mean, you were a kid, you know, we mature. Like, you know, we're all different versions of ourselves as we get older. Yeah. Like me at 30 and me at 20 are very different from who I am today.

And it sounds like you started to kind of realize this. Were you okay with criticism? and feedback or would you get defensive? 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, asking put my manager on the line, even though I'm the only person in the company, you know, like, and literally leaving

and being like, I'm done with you, this product sucks. And so over the years, I think 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 ignored something at the point where something's really going to break. So I'm more about trying to listen to what's there and figure out what I can feel. 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 think that I'm not making any now I have to be 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 Squarespace also changed like you guys you guys had a pretty interesting strategy which was to advertise on podcasts you've advertised on ours full disclosure and and people weren't really doing that in 2010 yeah so we did it even before 2010 i mean podcast was yeah i remember um you know we were gonna we were gonna maybe try a podcast ad the first podcast we did was this week in tech and uh i remember it cost like something like 30 grand i'm like that's our whole ad words budget for like the whole month in how many podcast 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 it. 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 bored with this. I love podcasts. I love this show.

Thank you, Squarespace, for doing this. and I think that 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. Later on, it was a joke when we first did our Super Bowl ad. Somebody was tweeting they were like, I didn't know the Super Bowl was a podcast. So yeah, I mean, we went in this space and 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 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 the way we did. 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? Was that the game changer for you? The outside capital is not it. The main driver for it. was Squarespace 6 launching, and that changed everything for us. So this is in like 2012 July.

This is version 6 of Squarespace. Version 6 of Squarespace. It's the one that, you know, small team, a couple of years after this investment, came together. This is the re-write. This is the one that's online, right? Yeah, this is the one that's online today. It's technically seven, but it's not a big version difference. It's not as big.

And it changed all of our metrics. You know, you had all these crazy, beautiful, sites you could do. They're portfolio sites with full screen images. You could use those for businesses. The sites were, it was some of the first sites that worked perfectly on mobile phones without any adjustments, right? And so that was a big deal. Without that product, Squarespace wouldn't be here. I'm curious, how did you, I mean, you started this in 2003, 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 first had.

Squarespace out in the world. Yeah. Yeah. Well, in a way, what's funny is it's almost less fragmented. And, you know, I don't know if you could grow a business on AdWords the same way I did 15 years ago, because I think people look, 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's really, as we've grown, the ambition of the company has 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 to the kinds of sites you can create on Squarespace 6? 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. You now have this huge platform, right? Yeah.

And it means that with that comes like responsibilities that you prioritize that you probably probably never even imagined power that you probably never even imagined or wanted. Sure. There was some controversy, I think, last year where some, like, white supremacists were using Squarespace. And, you know, you're going to face these things all the time. Yep. How do you, do you weigh each situation?

Like, how do you, you know, like, what do you do? Yeah, you try and have rules around it. And so one thing that's great about Squarespace, frankly, versus other, 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 going to post a bunch of bad stuff online. So here's my credit card and here's my address and I'm going to post it up. 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 time goes on because, you know, 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, you know, 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. I think at the end of 2017, Squarespace raised $200 million in funding. Valuing the company at $1.7 billion might be valued higher now.

That's a lot of money. I mean, you were, you know, your tech success and you do these conferences and you're on these shows and, you know, you're worth a lot of money. But you are also, does it also make it challenging to, you know, to make 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 kind of gone through a lot with me. And I know kind of what that looks like when it's, you know, non-superficial. And yeah, I still have a lot of friends from, like, from that original apartment in New York. I think that's been a really positive part of my life. I actually have we stay in touch.

And, you know, look, you get older and context changes. So it is harder. It becomes harder to meet people. Sure. I mean, when you're 23, 24 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 open. Now more people are in kind of family modes and everything else. Do you ever think that you want to do that?

I mean, have family? It's a great question. I've really put off thinking about that. Yeah, I mean, just so much has changed in my life so rapidly. I've just really been focused on all of that. I mean, I'm not ruling it out. I just, it's not front and center right now. But, you know, the things are front and center on my mind at 25 and 35 and 15 are different.

Yeah. And I hope it don't sound like your mom. Like, well, when are you going to have your 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 of your success do you think is because of that talent and your skill and your intelligence? 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 parents had a computer around me when I was a kid, right? I'm lucky the data didn't get deleted the wrong you know all these scenarios I mean you know we're just even scratching the surface of the crazy things that have happened I mean um I'd say that there are qualities I probably have that have helped me stay here around you know perseverance and pain tolerance and um and I guess some level of adaptability um my best moment some kind of self-awareness But no, I think that anyone who possibly claims that they didn't get lucky is crazy. That's Anthony Casalena, founder 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 cards 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 Westervelt. Waddling around Target because she'd just been released from the hospital where she'd given birth to a nine-and-a-half-pound baby boy.

So Kate was sore, and she had stoutly. ditches 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 fully stocked 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 sticks.

which is 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 of things. 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 going to 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, then I would test them all. Maternity pads, creams, protein bars, herbal supplements. 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, but... I ended up with a C-section, and what I really needed was a heating pad to place on my belt. 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 for 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 Westervelt's business is called Mom Box, And if you want to find out more about it or hear previous episodes, head to our podcast page, How I Built This.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 hibt at npr.org. And if you want to send a tweet, it's at How I Built This. Our show is produced this week by Casey Herman with music composed by Ramtin Arablui. Thanks also to Julia Carney, J.C. Howard, Nur Kudsi, Neva Grant, Melissa Gray, Sanaz Mechkampur, and Jeff Rogers. Our intern is Candice Lim. I'm Guy Raz, and you've been listening to How I Built This from NPR.