The Exchanges

Q Did you call it Squarespace already? Like, did you already pick that name?

A Yeah, I, I can't remember exactly when I picked it, but I needed to get the, the .com, the .net, the .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 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, Squarespace, 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. Probably gonna pick like a square or something like that. But, um, yeah, I mean, that's kind of, that's kind of where it started.

AI assessment note: “Yeah, I, I can't remember exactly when I picked it, but”

Q and more people are using Chatbots to, to do search, right? That they might've gone on Google before, and now they're, they're going on chat or perplexity or whatever. Um, how does that change the, the, what it means to have a website, right? Like you're a business, your website is your storefront. Um, how do you stay relevant when that's how people find out about you more and more?

A Well, that's, that's one way people find out about you. And, and I think that the website ends up being more relevant than ever for a number of reasons. One being, It's where the answer engines are finding their information. You know, they're crawling the web and using either old data or modern data or more relevant data to give you the answers they give you, and when they don't have the answer to a real-time question, they go to the web, and so it's being used in both their index, and it's also being used, um, for real-time interactions, and then, you know, most of the interactions with a small business being contacting them, submitting a contact form, Booking an appointment, purchasing a product. That's still happening with some kind of direct interaction with that customer, and we, we facilitate that interaction, whether you started on a search engine, or an answer engine, or a social network, or anywhere else. And so, we're really happy to be positioned as we are in this, in this era.

AI assessment note: “I think that the website ends up being more relevant than ever for a number”

Q you know, basically build out, uh, websites, designs, and that's happening very, very fast, right? I mean, what, what, what may be available in a year from now, Like, you, you may not even be able to fully anticipate that, right? What, what does it mean for, for your business and how it sort of fits into that, into this sort of brave new world of, of, of AI tools?

A Yeah, I mean, it's been a phenomenal tailwind for us. I mean, we're not particularly worried about the, you know, the idea that people could code a website where they couldn't code a website before because people haven't had to code websites for two decades using Scorespace. Um, but, you know, we have AI and what used to be called machine learning, frankly, enabled into every aspect of our product, and in fact, our Blueprint AI product, which is the primary way you would get started with Scorespace if you just click Get Started, Was named, you know, one of time's hundred best, uh, inventions of the year, uh, just last week. So we've got it everywhere, and, um, from optimizing your site for SEO and AIO to helping you generate, uh, imagery that works for you, um, you know, we've got AI enabled and, you know, probably 15, 20 plus touch points in the product right now.

AI assessment note: “it's been a phenomenal tailwind for us. I mean, we're not particularly worried”

Q By the way, what did it cost to sign up for Squarespace in those first few months? Do you remember?

A So, 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. 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, um, MySpace, whatever. Like, people would be like, you give it away for free, and then people are gonna 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. So, and, and it was really not the point of the thing. It was, I was not out there trying to make the next live journal or blogger. I wanted to, let me focus on the people that want to pay for this. And I forget what it costs time between five and 15 bucks a month, you know, really inexpensive.

AI assessment note: “actually for the first year, we did have a free plan”

Q Uh, and, and how did you cope with that? Was that, Was it exciting? Was it amazing? Or were you stressed out? Or what?

A 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, the end of the month, it's like, nah, I just, I ran AdWords, I paid my taxes, and like, you know, I answered customer support, and I think, wow, I didn't actually get anywhere. And so I started to be like, okay, this isn't gonna work. And two, 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.

AI assessment note: “I think it took me years to fully appreciate what the stress was really doing”

Q 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?

A 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, a 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, like, I just learned so much. I mean, because, again, I, I've never worked anywhere else, really.

AI assessment note: “I started realizing what a horrible manager I was. You know, after this investment”

Q 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? How much of it do you think is because you just got lucky too?

A 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, 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, and my best moments, some kind of self-awareness, but no, I think that anyone who possibly claims that they didn't get lucky is crazy.

AI assessment note: “Oh man, I have been lucky so many times in my life.”

Q And, and did you, did you have any cash, any money, any small amount of capital to actually try and launch this into a business?

A 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. There was 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, and I needed money for the servers. So I, I went to my, I went to my parents, uh, who, you know, I don't know how to calculate, but I needed 30 grand. And, you know.

AI assessment note: “So, back then, I didn't.”

Q So did you, um, 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?

A You know, it was interesting how it evolved because, you know, it was a year of like 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, where's, where's your job? And I, I really started 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, hey, I gotta pass. I'm in school.

AI assessment note: “instead of graduating in four years, I waited and graduated in five”

Q But, but what was stressing you out? What, do you remember what, the things that would stress you out?

A Yeah, I, I, I think that 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, this psychological Here you go. Figure it out. Figure out why it's broke. Like, 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, and all those, I didn't have any employees, and yeah, it was a self-service thing. In the other hand, I'm completely and totally trapped.

AI assessment note: “trying to do it alone for a while, The infrastructure side of stuff”

Q with this company. I mean, you were a kid, you know, we matured like you, you know, we're all different versions of ourselves as we get older, like me at 30, and me at 20 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?

A 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, asking to 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, um, 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.

AI assessment note: “I developed some amount of realization that, um, I need to create an environment where I hear feedback”

Q Um, he was there for five years, and then he, he, 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, or was it actually ok?

A 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 dialogues 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, what I was thinking about.

AI assessment note: “It wasn't really okay.”

Q And by the time you graduated college, I've read that you, you guys had, like, about 10,000 accounts, and, um, 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, and CEO.

A Yeah, I was, 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 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 and 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'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.

AI assessment note: “Yeah, I was, I was kind of everything.”

Q I'm curious, how did you, I mean, you started this in 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 a much more complex world than it was when you, when you first had Squarespace out in the world.

A Yeah, yeah. Well, 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 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 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 to, 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.

AI assessment note: “Well, in a way, what's funny is it's, it's almost, uh, less fragmented.”

Q So now you are about to launch the app store. You're looking to figure out how do you get people to be aware of it, right? There's millions of apps out there, right? How do you, how do you get people to adopt this? Um, Anthony, I want to bring you in here because we got probably lots of questions, uh, and also some thoughts on how to do that.

A So the challenge is obviously that there's millions of apps out there, and then there's also a fatigue related to apps. I think that, yeah, I don't have the stats off the top of my head, but I, I feel it personally myself. It's like, it's kind of a lot for me to install a, a new app. Um, obviously, you know, something as targeted as yours, I think there'd be maybe, uh, less resistance to, but I, I guess I would, I would say this. If, if imagine it wasn't even an app, where do I find it? And does it need to be an app? Does it have, could it be a website that then leads you to an app once you use it? So imagining it wasn't an app, because I'm actually not somebody who's ever, um, uh, been successful or really launched a lot of, a lot of things in the app store that weren't related to another thing. How do people find it? How do they, how do they, um, how do they find it?

AI assessment note: “does it need to be an app? Does it have, could it be a website”