Squarespace CEO Anthony Casalena on podcasts and combating fake news

We recently caught up with Squarespace CEO Anthony Casalena on his arrival at the company’s Dublin office to talk its future in Ireland and why podcasts are a marketer’s dream.

It is coming close to four years now since Squarespace announced that it was following in the footsteps of American tech companies like Google and Facebook in opening an office in Dublin with the creation of 100 jobs.

Since then – and a few moves later – the company now finds itself not in Silicon Docks, but within the heart of the city on Great Ship Street in what was once Medieval Dublin.

In the past two years, the company – whose business allows anyone to create and host a drag-and-drop website – has done quite well in Ireland.

Figures released earlier this year showed that for 2015, the company’s profits in Ireland was pushing €200,000.

This is led by its staff of 115 largely responsible for its customer support in the rest of the world outside of its native US.

While the company has yet to IPO – but rumblings continue to suggest it might – the company has declared revenues of $200m in 2016 with more than 1m paying customers, 30pc of whom are based outside the US.

So where does the company, considered one of 10 major cloud computing players last year, go from here? recently got a tour of Squarespace’s Dublin office that revealed a workspace whose colour palette is anything but similar with some other major tech players.

I also managed to catch up with the company’s CEO and founder Anthony Casalena who was in town to check in with his international staff.

With help from a $30,000 investment from his father, Casalena started Squarespace back in 2003 – and launched in 2004 – at a time when most websites were still using GeoCities web hosting.

So what inspired him to break into a market that was largely offered for free?

Remembering GeoCities

“It was originally conceived for two reasons: I was making it for myself and I wanted something all-in-one,” he said.

“I didn’t want to have separate hosting, separate page building, separate software, separate statistics software etc.

“It was this belief that design mattered and presentation matters and how you present your ideas online matters and I wanted a service for myself that was a better representation of my ideas.”

I suggest however that much like the GeoCities sites of old, is there a fear that offering the same set of tools to everyone might result in a boring, homogenous design of websites?

Not so, Casalena said, believing that most of its users are more concerned with building a functional website that will help their business.

“At the end of the day, people aren’t creative directors and might not even want to touch that aspect of the business; [in the same way that] I don’t want to design my own shirts,” he said.

“It’s important they’re provided with options that are good. That’s one of the things that Squarespace has really excelled. There are some really different looking sites on Squarespace and I’m hoping that we break out as much as possible from that templated universe.”

Why Squarespace loves podcasts

As an avid podcast listener, I felt compelled to ask the question of how much the company spends on podcast advertising.

From Serial to The Joe Rogan Experience and many others in between, you may have heard various hosts advertising the service.

“I think podcasting is a unique opportunity as in the best of cases, it can connect with the show hosts and if they believe in the product and they’re authentically endorsing it, it’s a really powerful thing for us,” Casalena said.

Because podcasters are usually looking to make their own website, I ask?

“It works really well,” he responds with a smile, “The audience of people who listen to podcast are well educated, sophisticated, entrepreneurial and a really good audience for us.”

This hasn’t stopped the company spending serious money on traditional advertising, seen in its recent Super Bowl TV commercial with actor John Malkovich.


Hosting in a time of fake news

While as a business Squarespace is still trying to grow its brand awareness, one area it might have to delve deeper into in the coming years is the issue of fake news.

While Facebook strives to distance itself from being named as a publisher, website providers like Squarespace also find themselves in a situation where user generated content can potentially incite hatred and violence.

It remains however an issue of free speech for Casalena and Squarespace with the founder making it clear a line has to be drawn at some point.

“There are all manner of opinions expressed on Squarespace online, a lot of them I don’t agree with,” he said. “This ranges from the religious spectrum and across to the political spectrum.

“I think we have a right to defend free speech online but… disclosing people’s personal information and calling explicitly for violence is where we draw the line and cooperate with law enforcement.”

Further expansion expected

This same sense of free speech was felt by Casalena when he was one of the many signatories by tech CEOs of an open letter sent to Donald Trump following his snap ban on immigration from seven Muslim-dominated countries.

Looking to the company’s future in Ireland, I couldn’t help notice that there were quite a few empty desks in one corner of the office, so perhaps further expansion is in the works?

With 115 staff currently employed in the Dublin branch and space for up to 300, Casalena agreed that there is room to expand.

“We have a lot of room to grow here and we’ll continue to invest here and I hope over time we can start to – when it make sense – to put other roles her besides customer operations roles.”