Squarespace founder on hosting John Malkovich and a million other customers worldwide

Anthony Casalena swears he's not a goth or a Depeche Mode superfan.

Nevertheless, no other expanding tech company surrounds itself with so many blacks, whites and greys as Squarespace.

"I'm not a goth," says Casalena, sitting in a grey shirt and black jeans. "But I am a monotone guy."

Online, monotone design helps his company. Squarespace is growing at breakneck speed thanks to an expanding number of small businesses and individuals that need an online professional presence beyond a Facebook page. The blacks, whites and greys of the company's front end help to make customers' own website choices stand out.

Casalena is used to looking for little ways to create a head start.

For anyone listening to a popular podcasts over the last five years, there was always one sponsor you couldn't avoid.


"This podcast is brought to you by … Squarespace."

Having repeatedly seared the name into a million podcasts listeners' heads, the company had to start delivering on its promise to walk people through the creation of their own website or online shop.

Today, it's so popular - it has over one million paying subscribers - that the ads have moved up from podcasts to the Super Bowl.

There's a bit of a difference.

"On the spot alone, it's between $4m and $4.5m," says Squarespace founder and CEO Anthony Casalena. "And then you have a matching spend which the network requires of another $4m or so of inventory on their network."

For Squarespace, which now has revenue of over $200m (€188m) and is in a profitable position, this can now be afforded.


But Casalena remembers the first time he made the leap into the world's most expensive sports ad event.

"I had such a panic attack," he says, sitting in the company's expanding Dublin office.

"We had a floating position, so we didn't know when it was going to come on. I remember going to this bar in New York. You can always tell which ads are working and which aren't because people either shut up or they don't.

"And it becomes increasingly hard as the night rolls on because people get drunk."

"I remember when it came on, the whole bar stopped and watched it. That was just 80 people. But I remember thinking: '100m people just did that'. It's inconceivable that that's the size of the audience.

"I looked at my phone and there was a traffic spike and all this crazy stuff started happening."

Since then, a lot has happened. Buoyed by the 'gig economy' and a steady demand for small businesses to have an online presence beyond Facebook and Twitter, Squarespace has grown to the point where it has opened expanding offices in Dublin and Portland, Oregon. The Dublin office now holds 115 people but the company has taken enough space for it to grow to 300.

"As we look to the future here, I hope we can have even more teams centralised out of Ireland. There's a budding engineering culture here. Some of our server reliability engineering teams could be run out of here, so we're looking at that. We're 115 people here but we have room for 300 in the building."

Read more: First look inside Squarespace's new Dublin hub - behind the scenes with the people behind your favourite podcast

Casalena says that he was aware of Dublin as a tech city because of the companies already here.

"We were aware of Google, Dropbox, MongoDB, companies like that," he says. "It's mostly asking around peer companies."

Squarespace is a private company which isn't looking to IPO soon, says Casalena.

"We don't have plans for that," he says. "Our mission here is to build a great company, not build towards a financial event. If there's a time where it makes sense for us to be public, I'd want to be ready. But it's not some end game we have in mind."

However, the company is in decent financial shape, he says.

"We operate to cash-flow break even so we reinvest everything we make. We showed a slight profit last year, but we're not trying to.

"We're trying to reinvest. We have over a million paid customers and last year revenue was over $200m, so that gives you a sense of the scale."

Despite thousands of micro-businesses using Facebook as an online holding space, Casalena doesn't see the social media giant as a direct competitor.

"We see Facebook as a distribution platform rather than competition," he says.

"We tell customers that Squarespace is their home base, it's where people will land if they try to Google you. No-one else controls it, we don't put advertising on it, it's theirs.

"But they obviously have to get it out there. So if that means tweeting or using Instagram or Facebook or whatever they decide, they should be on all those networks. So that's why see Facebook as being complementary."

Why creates websites, though? Small businesses and solo operators in the new 'gig economy', that's who.

One of Squarespace's most famous customers is actor John Malkovich, who hosts his clothes design website with the service.

But the new startup culture, where every second person has some portfolio or professional service on the side, is creating a steady stream of customers for Casalena's company. His customers are people who can want to trade but can't code.

"A lot are small businesses," he says. "But you'll also see creatives and agencies and online sellers, authors, wedding websites, restaurants and professional services. It's set up to appeal to a wide range of solutions. There's absolutely a movement where people are empowered by services like Squarespace.

"People realise that they can start a business themselves and start selling online. That has increased massively and will again over the next 10 years."