Interview with Squarespace CEO Anthony Casalena

Next-generation web publishing platform Squarespace has tens of thousands of customers and serves billions of hits per month. Founder and chairman Anthony Casalena tells Oliver Lindberg the secrets of its success

This article originally appeared in issue 202 of .net magazine in 2010.

Anthony Casalena has been developing software since he was 15. While at the University of Maryland, he wanted to create a personal website but found that there wasn’t anything that let him build a blog, manage a photo gallery and edit a page all in one package with a unified interface and a coherent back-end. So he started to put together his own program, launched it in January 2004 and borrowed $25,000 from his parents for servers and Google AdWords. Today Squarespace has tens of thousands of customers and serves billions of hits per month.

High profile customers include ABC, Marc Ecko, McCann Erikson, L’Oréal, Kiels and Kevin Pollak, and last summer awareness of Squarespace rocketed when the company gave away iPhone vouchers. But in a world increasingly dominated by free, freemium and open source, the Squarespace publishing platform stands out for another reason. You have to pay for it.

There’s a free, 14-day trial but if you’re happy with the test drive, you need to buy an account. Price plans range between $8 per month for the basic package and $50 for the community package. “Because we didn’t have outside capital, I was very focused on making sure Squarespace was always profitable,” Anthony explains. “We played around with a free account for a couple of months but I really wanted to focus on the premium subscribers we had, so I turned it off. I know it will never have the market-share awareness of something that’s completely free but that’s just not what we wanted to focus on. Now it’s evolved to the point where $8 or $14 is a very small amount to pay. Because if it clicks and works for your site, you’re going to save hours, if not weeks of time.”

Unlike conventional CMSes like WordPress and Movable Type, Squarespace is a cloud-based environment that doesn’t require you to know anything about CSS and HTML but comes with a powerful WYSIWYG editor. If you are a coder, however, you can still go in, easily access and edit the code and write your own CSS. According to Anthony, it’s the only way forward for content management systems. “Unless you have very complex code, I really think do-it-yourself, self- install services like WordPress and Movable Type are on the way out. I don’t think anyone needs to run their own servers these days. That’s going to be for the tinker in the future. There’s always going to be a spot for it, and as a programmer I like to run code and servers. But I don’t think the casual end user should ever do things like that. That’s all going to move into cloud-based hosting. We’re uniquely positioned to offer a kind of hybrid. It’s a cloud-based system that’s very scalable and high in configurability. That’s what people are paying for.”

Squarespace exclusively relies on the Yahoo User Interface JavaScript library (YUI) for the front end. Everything else is custom written. Third-party plug-ins are not part of the Squarespace philosophy, which aims to give its customers as much control over their sites as possible, so they don’t end up with cookie-cutter sites. There’s a lot of flexibility built into the system. Themes and every single element of the site can be customised, changes previewed in real time, you can jump straight into the HTML and designers don’t have to worry about servers. Everything can be done right in the browser, which might explain why the customer base is now pretty much equally split between consumers and designers. Clients won’t be overwhelmed and lost in the product when designers hand off their sites. They can easily update and modify content themselves, without the fear of breaking everything.

Reliability, of course, is another crucial factor and although the service is under a huge load, Squarespace claims 99.98 per cent uptime. “We’re maniacal about uptime because we’re one of the few platform providers that use their own service for their front site. We eat our own dog food. Squarespace.com is using the same infrastructure that everyone else is. We’ve devoted an immense amount of resources making sure our site stays up and our customers’ sites stay up. As an individual using a shared host, you can never replicate anything close to that without spending millions of dollars. It’s an alignment of interests. It’s perfect. Nobody gets special treatment. Every single server serves every single site. By virtue of just signing up, the site you’re making scales forever.”

As much effort and energy as Squarespace puts into keeping the sites up, the team – now 26 people operating from the heart of Manhattan – puts into making sure modules really work. “The Journal module is pretty much feature-competitive with WordPress and Movable Type. Anything you’d expect from those products will be in that Journal module because our site was originally conceived as a blogging product. We always knew it would be able to manage bigger multi-page websites, whereas a lot of blogging products were just focused on managing a blog.” The same applies
 to widgets. “When we introduce a search widget, we don’t just stick in Google Search. It’s our own search product that’s written, so that whenever you update contents, it’s instantly updated in search, it pays attention to your public and private areas.”

Last summer, Squarespace introduced a blog importer feature to solve a problem the company was having with its customers. “All CMSes tell you that you can take your data with you,” Casalena explains. “They all have exports but they don’t really import anywhere. If you export something from your WordPress.com account to import it into Squarespace or any major CMS, two things happen. One, your URLs break because they change and then any rankings that you had in your search engines before don’t really transfer. And two, your images stay referenced in your old account, so you can’t actually cancel it. The blog importer solves both problems. It ensures that if you’re moving from any supported platform, your URLs stay exactly the same and all images are re-hosted in the cloud, so you can turn off the old account. I don’t know of any platform that does that right now.”

In November the company’s first iPhone app followed. Emulating the UI of the main services, it enables customers to control their website content right from the iPhone, previews changes live and gives them access to their statistics. Next up on the release schedule are social widgets. “We’ll make sure that we can bring in all of your social data from various sources like Flickr and Twitter into native Squarespace widgets, so you can present different streams on your site without having to include JavaScript. If you have a site with a Twitter or Digg stream, it is still going to load instantaneously with one request, instead of it loading and then stopping for five seconds because Twitter is down.”

Arguably the biggest project the team is working on is the highly anticipated version 6 of the platform. “It’s an incredibly sophisticated layout system, which is going to address a lot the issues that our current sites are having with layout,” Casalena enthuses. “Version 5 is great for making engines before don’t really transfer. And two, your images stay referenced in your old account, so you can’t actually cancel it. The blog importer solves both problems. It ensures that if you’re moving from any supported platform, your URLs stay exactly the same and all images are re-hosted in the cloud, so you can turn off the old account. I don’t know of any platform that does that right now.”

In November the company’s first iPhone app followed. Emulating the UI of the main services, it enables customers to control their website content right from the iPhone, previews changes live and gives them access to their statistics. Next up on the release schedule are social widgets. “We’ll make sure that we can bring in all of your social data from various sources like Flickr and Twitter into native Squarespace widgets, so you can present different streams on your site without having to include JavaScript. If you have a site with a Twitter or Digg stream, it is still going to load instantaneously with one request, instead of it loading and then stopping for five seconds because Twitter is down.”

Arguably the biggest project the team is working on is the highly anticipated version 6 of the platform. “It’s an incredibly sophisticated layout system, which is going to address a lot the issues that our current sites are having with layout,” Casalena enthuses. “Version 5 is great for making sites that have top and bottom navigation bars, a header and two or three columns. Version 6 is going to open up that layout system and pave the way not only for more complex layouts but sites that have more complex navigation.”

Squarespace’s revenues amounted to a reported $2.2million in 2008 and although Casalena isn’t willing to discuss figures, he does reveal that revenue is growing around 160 per cent year- over-year. Over the last three years it’s grown a mind-boggling 700 per cent. Until now, the company has accepted no venture funding but it’s now open to having a partner in a minority position, as long as the vision and decision making of the Squarespace team continues to control the company. If Casalena and his team have their way, Version 6 will cause more trouble for WordPress and convince more people of the benefits of a powerful, cloud-based CMS.

Casalena is still the CEO of Squarespace, which now employs more than 500 people across New York, Portland, and Dublin, Ireland.


This article originally appeared in issue 202 of .net magazine in 2010. Photography by Daniel Byrne