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Interview: Squarespace Founder/CEO Anthony Casalena On Designing a Great Web Platform

Anthony Casalena | Web Entrepreneur | Stated Magazine Profile

Anthony Casalena on Stated

At age 20, founder Anthony Casalena began work on what would become successful blogging and web-building platform, Squarespace. Now 7 years on, the self-proclaimed “paper for the web”  allows users of varying skill levels to quickly and elegantly create a high-quality and powerful web presence. stated itself is built on the platform, which has attracted such high-profile users as tech gurus Leo Laporte and (Digg founder) Kevin Rose and celebrities Kevin Pollak, Marc Ecko and Dane Cook. We caught up with Anthony, now CEO, in the midst of work on the next iteration of Squarespace, Version 6.

stated: How would you describe what you do “in a nutshell?” What initially drew you to it?

ANTHONY CASALENA: I’ve always really loved computers. When I was really young, I would get on my dad’s i386 with DOS and play around with it until it broke, causing him years of grief. After a few rounds of this, they bought me my own computer and I’ve been at it ever since. I learned to program around the age of 15—initially writing scripts for chat networks and making new interfaces for things. I really loved the ability to control what a user was experiencing. You could really make people feel something depending on how you presented your program to them. You could build useful tools.

stated: Where did you grow up? Do you come from a creative/arts-oriented family? Are you a product of public school?

ANTHONY CASALENA: I grew up in Northern Maryland—pretty much in the middle of nowhere. I literally lived 250 feet from a cornfield and went to a public high school. My father was technical, but was involved in many internet companies in a sales capacity. My mom was very creative—I think a lot of my aesthetic comes from her. Our house at home is all white—it’s pretty ridiculous.

stated: I guess the apple doesn’t fall too far from the tree. You first began what would become Squarespace in 2004 in your dorm room at the University of Maryland (the Alma mater of two of our editors). Can you tell us how it started? What were you working on and what inspired your approach?

ANTHONY CASALENA: Initially, I wanted to create a pretty simple personal website for myself. I looked at a few blogging packages and photo websites out there—but was really unattracted to their design and the integration work you would have to go through to get the things running. I didn’t want a separate blogging package, photo package, FTP program, statistics platform, etc. I thought it would be more elegant to put these together into a single product. That product became Squarespace.

That platform is quite a bit different than what we run today—many parts of the code were re-factored over time to remain current. We rewrote a good part of it using Javascript when we launched V5 [version 5] a few years ago, and we’re amidst an even bigger rewrite now. We’ve become far better designers than we ever were. Our new stuff is looking better than ever.

stated: Finding success at such a relatively young age, you must get Mark Zuckerberg “Toddler CEO” comparisons. Clearly folks are taking notice now (ahem…$38.5 million investment), but was it ever an uphill climb to be taken seriously?

ANTHONY CASALENA: Absolutely. The number of non-starts and setbacks leading up to that event were numerous—I was very young. You just have to keep going. I literally ran Squarespace alone for three years in the beginning, doing work spanning from customer support all the way to systems engineering. I understand all of those parts of the business well. I’m a very ground up thinker—my goal in year one was never to be a very large company or to land a huge investment. It was always about getting methodically to the next level.

stated: No one else in this space is doing quite what you are—users of all skill levels can really dig in and do what they need to do—and quickly, with a slick user experience. It’s clearly attracted lots of artists and creative types. Was that always the case? How much of a role do you feel your brand aesthetic plays in your success with Squarespace?

ANTHONY CASALENA: I think Squarespace as a company represents a pretty unique split between design expertise and engineering expertise. They’re both critical to how we think about the world. As this is who we are, and it’s not surprising that we attract creative types with a very particular sort of aesthetic. It’s why we placed the company in New York—I was very attracted to the creativity and spirit of the city. Some of my favorite experiences in life are from meeting talented people who used the platform to do something creative that they didn’t think they could do.

stated: Have you found one particular industry has become your strongest niche?

ANTHONY CASALENA: It’s really the design crowd that we seem to connect with the most. We’re the sorts of people who spend way too long getting all the details on the software right, and I think they really appreciate that sort of thing. Our company is split pretty evenly between design and engineering. The major mission with V6 [version 6] is to begin to verticalize our experience and get deeper into the needs of more groups. You’ll see who is attracted to us evolve over time as the system becomes more robust.

stated: We met at the Squarespace holiday party at your offices, which certainly attracted a large and interesting mix—invited via public tweet from @Squarespace. I think it’s fair to say your approach is open and user-centric. Would you say user feedback has driven the evolution of Squarespace?

Anthony Casalena on Stated Magazine

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ANTHONY CASALENA: It absolutely has, but one of the main things we try and do is create some surprise with our products. If you’re always looking to implement granular user requests, you miss the opportunity to do the bigger things that really delight people and solve their problems in new ways. You need to look at them as an aggregate and come up with your personal best take on their problems. We’re really about that. You have to keep a balance between short term and long term goals.

stated: That makes sense. Would you mind sharing a few examples of how Squarespace tackled this approach? 

ANTHONY CASALENA: Sure. The entire V6 initiative is nothing that anyone has ever asked us to do specifically. We get requests that our selective display feature isn’t strong enough, or that users want to put widgets in their site footer, etc. We took all of those requests and came up with some completely new ideas for our templating system. Unless you have vision across the entire product and all the requests, you wouldn’t be able to ask for what we created. It’s up to us to get the right solution to a given customer’s problems.

stated: I understand you’ve recently rolled out an iPhone/iPad app?

ANTHONY CASALENA: The premise is pretty straightforward—the applications give you access to your site statistics and posting interface on the fly. We spent a long time making the applications really feel like the web version of Squarespace—we didn’t want to put in half effort and get something that didn’t seem like it was a part of the system. This was really important to us. We weren’t the first way to produce blog content on iOS, but we’re focused on being the best.

stated: Do you have an iPad? Do you find mobile computing is changing the way you work and design?

ANTHONY CASALENA: It’s amazing how the entire industry changed after the iPhone—you can suddenly do things in mobile that just weren’t possible before. No more WAP and degraded experiences—the full experience for many sites can simply be made mobile. I do have an iPad, but to be honest, it’s a machine I like to leave around the house so guests can jump on the web. It’s mostly a reading device for me. It’s not changing the way I work or design.

stated: What inspires you? Is there a project that makes you say “why didn’t I think of that?” 

ANTHONY CASALENA: I really respect simple services that have gotten really popular. I rely on Dropbox every day—I don’t know what I’d do without it. I know that even though it looks simple, it’s really tough to get that right. This sort of thinking is a huge thing in Squarespace V6—we want the consumer experience to be really clear, and a separate developer one to be really powerful. I’m inspired by anyone who really takes the time to craft a relatable experience. Apple does it with computers. Guys like Ian Schrager do it with hotels. It doesn’t matter. Anyone really willing to say “this isn’t good enough” and push through—push for something that surprises people. I like that.

stated: Who and what are some of your other inspirations? Who are you listening to? What are you reading? What do you do in your downtime—assuming you have any?

ANTHONY CASALENA: Hah. I’m not reading nearly enough. I think I have “The Upside of Irrationality” by Dan Ariely on my desk. Skimmed “The Little Kingdom” about Apple. Someone told me to read “Moneyball” and “Liar’s Poker” too. Listening to a lot of Black Keys and Hood Internet (yeah…) recently for whatever reason. I don’t have a lot of downtime.

stated: Well, I know you’re hard at work on V6 and just launched Squarespace Location features. And were named CEO. So just a bit on your plate. Anything else coming up you’d like to share?

ANTHONY CASALENA: Just that I feel like Squarespace V6 is the best thing we’ve ever produced.

It’s taking some time to get out, but we want it to serve us for years to come. Our guys who are working on it—I’m really proud of them. I know Squarespace is a tough place to work at times, because we try and ask for something more. But when we get this out there into everyone’s hands—it will all be worth it.


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