Squarespace CEO Anthony Casalena on podcasts and combating fake news

11 Apr 2017

Squarespace CEO Anthony Casalena. Image: Squarespace

We recently caught up with Squarespace CEO Anthony Casalena to talk about the company’s 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 such as Google and Facebook, 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, Squarespace – which 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 profit 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 business has yet to IPO – although rumblings continue to suggest it might – Squarespace 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 – named one of the top 10 major cloud computing players last year – go from here?

Siliconrepublic.com recently got a tour of Squarespace’s Dublin office, which revealed a workspace with a colour palette that is slightly darker than the one preferred by its peers.

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

Aided by a $30,000 investment from his father, Casalena started Squarespace back in 2003 –launching 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?

Anthony Casalena

Anthony Casalena in Squarespace’s Dublin office. Image: Connor McKenna

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 that, much like the GeoCities sites of old, there is 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 [at]. 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 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 podcasts are well educated, sophisticated, entrepreneurial and a really good audience for us.”

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

Hosting in a time of fake news

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

While Facebook strives to distance itself from being named as a publisher, website providers such as Squarespace are also finding 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 his company, with the founder making it clear that 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 sentiment of free speech was acted upon by Casalena when he became one of the many tech CEOs to sign an open letter to US president Donald Trump, following his hasty ban on immigration from seven Muslim-dominated countries.

Looking to the company’s future in Ireland, I couldn’t help but 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 – when it makes sense – to put other roles here besides customer operations roles.”

Colm Gorey was a senior journalist with Silicon Republic