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Squarespace Brings Internet to Life in First Super Bowl Ad

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The words "Super Bowl ad" were usually uttered as more of a joke than a true marketing strategy among the team at Squarespace — at least until recently.

Anthony Casalena launched Squarespace in early 2004 with $30,000 in funding from his dad and a plan to provide better tools to help people build websites. He says he spent "a couple hundred bucks" on Google AdWords that first year to market the new service.

In the decade since then, the startup gradually expanded its marketing efforts to include five-figure AdWords buys, sponsored podcasts, marketing on Pandora and Spotify and, last year, TV spots. Even so, the idea of investing millions in a Super Bowl ad wasn't taken seriously until the second half of last year, thanks in part to the early success the company has seen with television campaigns.

"It's funny when that joke becomes a reality," Casalena says. "It was like, 'You know guys, we really could.' Well, let's think about that for a second: Do we really have something big enough to say? Do we have the budget for it? Do we have the creative talent for it? Is the product ready for it?"

After checking off the 'yes' column to each of those questions, Squarespace commited "well into the seven figures," according to Casalena, to produce a 30-second spot that will air during the big game this weekend. The quirky ad, which was posted online Monday, brings the worst parts of the Internet to life — everything from virus alerts and aggressive promotions to snarky memes — in a frightening mob scene, before suggesting Squarespace can make it better and less chaotic.

Casalena says Squarespace took note of previous Super Bowl marketing efforts from similar services like GoDaddy, and did go for something "a little more dramatic" than its usual ads, but an ad that doesn't deviate too much from its core values.

"I do believe that the ad communicates Squarespace's values in a really elegant, shareable, fun way," he says, "where we are drawing this contrast between this messy web that we've all come to understand as the norm and a cleaned up version."

Squarespace's business has grown to serve "hundreds of thousands" of customers, according to the company, but the goal now is to go after a mainstream audience with the Super Bowl ad and subsequent marketing campaigns. Casalena acknowledges that many of those chowing down on wings and beer during the game may not be particularly interested web design, but he believes the ad still has the potential to attract millions of viewers.

The startup plans to track the ad's impact by surveying future customers about how they learned of Squarespace, tracking the number of media mentions and looking at changes in the company's growth trajectory. "[We're] hoping to see a trends change in the overall business," Casalena says.

Given the millions of dollars it costs to produce and air the ad, he acknowledges theres certainly a risk about whether it will pay off.

"We absolutely consider what the balance could do otherwise. It could be spent on any number of things to further the growth of the company. That's under consideration," he says. "In the context of our budget right now, this was a risk that we were willing to take."

After all, as Casalena points out, you can't just limit yourself to spending on Google AdWords forever.

"You do see saturation effects in certain channels. You can't just spend $15 million in AdWords if it's not working," he says. "You do have to constantly find new green fields to go after."

Squarespace raised $38.5 million in 2010, its only round of funding to date other than the money Casalena received from his dad. The company is currently cash flow break-even.