Index Insight

We give a voice to ideas

Squarespace CEO Anthony Casalena on "solving" publishing and why we will all need a place to live online.

When he first came up with the idea for his startup, Anthony Casalena, then 20, was attempting to build a personal website. Frustrated by the site-building services on offer at the time – most of which involved assembling multiple pieces of software, while all but ignoring design -- he decided to do the work himself.

“When I first started coding in 2003, I really was just making a site for myself,” he recalls. “I didn’t have a grand business plan in my head. But, very quickly, it became obvious that other people may want to use this and that what I was doing could solve far more than just the original thing I had in mind.”

The end result was Squarespace, an all-in-one platform, which set out to merge glitch-free functionality with the highest aesthetic values, by equipping users with an array of creative tools with which to design, build and maintain their websites.

Launched from his Maryland university dorm room in 2004 with $30,000 borrowed from his father, the service essentially remained a one-man band for its first three years, with an undoubtedly frazzled Casalena covering the engineer, designer and support representative beats simultaneously.

Fast forward to a decade later, and those early days seem like folklore. Manhattan-based Squarespace has since burgeoned into 189 staffers and hundreds of thousands of paid customers. More than 2.4m sites have been created on the platform to date.

Over the intervening years, explains Casalena, the company’s ambition has been utterly transformed. “Today Squarespace has become this big journey into creating a publishing platform that solves publishing for a wide range of people.

He continues: “We’re decades into the story of the web right now and there’s been no one single publishing platform that’s really solved content management in a fundamental way, for consumers or developers. That’s evidenced by the fact that, if you look at our industry, you’ve a completely fragmented market, where there are tons of competitors.

“So we think of publishing as an unsolved problem and our purpose is to keep pushing on that goal.”

Powering creativity

Asked what differentiates Squarespace from its competitors, Casalena singles out the emphasis the company places on fusing design and engineering very early on in the process.

“We prefer to have those two mind-sets sitting at the same table from day one,” he explains. “We like designers and engineers that are really running with the project themselves, that are self-motivated and define their own constraints -- and work as a small team.

“That way when we launch a feature, we make sure it is fused and integrated together with the platform. For instance, if we launch calendars or music players, these features are using all of the core components of our main system and are fused together very elegantly.

“All of our templates understand the core underlying parts of the content management system. By controlling more parts of the stack, and ensuring all these things are fused together from a project management perspective, you can then deliver this unified core, this unified experience.”

Based across two airy, light-filled floors of an upscale SoHo building, Squarespace’s workspace is every bit as stylish as its product. The city’s creative buzz seems to permeate it too.

“New York is an incredibly creative city,” agrees Casalena, a Maryland native. “There’s this amazing diversity of industries here.

“We’re lucky enough to have a thriving tech community now. Design has always been incredibly powerful here, too. So as a company that powers creativity, it really helps that you have more creative individuals in this city than any place that comes to mind.

“New York is also an incredibly international city,” he says. “We can really pull talent in from all kinds of places and [as a result] we have a lot of people in the company, who have come from abroad on visas. So, yes, that helps us a lot too.”

Be your own customer

Few startups are profitable from launch, but Squarespace is an exception – and having customers on board from the outset was the ideal way to measure genuine user-interest and iterate accordingly, says the founder.

“Paying attention to the market and trying to stay connected to reality and figure out what was really happening, and if people really like what we’re doing, was really valuable for us,” he says. “We made a conscious decision to charge for Squarespace from the beginning and having a paid product in the market helps us understand the true value our product has with consumers.”

Similarly, he’s always encouraged his team “to be [their] own customer” to ensure they maintain a user’s perspective on the service they offer. “When you’re using your own product, it means you’re not trying to understand the needs of others in an abstract way,” he says. “Instead, you’re really getting in there, figuring out a problem and rewiring your brain to understand it.”

Casalena also fosters a culture of “optimising towards ideals” at the company. “There’s a lot of emphasis today on being data-driven. We have sophisticated data platforms that we use to drive all sorts of decisions related to our marketing,” he says.

“But a lot of the times, using data and A/B testing only gets you to a very near-term solution [such as] ‘Was the button better in this shade of orange or that shade of orange? Or does this random line of copy work?’

“What it cannot do is help you make leaps. We’re attempting to take risks with Squarespace -- to create a product that would inspire and emotionally connect with people. So we tend to be driven by ideals and let numbers guide us, after we’ve put our ideal thing in place, as opposed to ‘Let’s A/B test every variant of this user-experience under the sun!’ That approach doesn’t create game-changing products or experiences.”

In the early stages of his business, Casalena had yet to develop a wide network of advisors and turned mostly to his initial investor – his father – for advice “on the business side of things”.

However, since Squarespace raised $38.5m in Series A funding from investors including Index in July 2010, he has increasingly picked up the phone to his VC partners too.  

Of Index, he says: “They have been incredibly helpful with a range of topics such as managing an executive team, trends in the industry overall, SaaS trends and things like that. Also with how to think about our numbers and whether they’re healthy or not.

“But, in the end, we’re the people who are on the ground every day running the company, looking at the market and coalescing the input,” he says. “We process fifteen thousand user-support tickets a week, so we have a good amount of real-time feedback. Ultimately it’s up to us, in this room, to figure out where to go.”

Online presence

Where to go, in terms of Casalena’s almost epic vision for the company, (namely to help solve publishing), is certainly well-defined.

So, too, is his prediction that having – and being able to control – a personal website will increasingly become the norm in most walks of life, over the next few years.  

“People will continue to have Facebook, Twitter and Tumblr pages, and a Foursquare profile and all of those different things,” he argues. “And those are all fine. But they exist on networks, and you don’t have full control of what’s happens on those networks.”

Moreover, in certain industries, being able to control your online presence will rapidly become more important, he says.

“For instance, in graphic design and photography, your website is your résumé. That’s everything. Will it be the same in academia? Maybe -- your papers are very important. Do they belong on Facebook or Twitter? That doesn’t really make any sense.”

That’s where Squaresapce fits in, he says. “We’re the place where your ideas can go and live online; we give a voice to ideas. Being able to have a place to express yourself that’s truly yours, a place where there will never be ads, is very powerful indeed.”