A Site for Sore Eyes

In just a decade, Anthony Casalena ’05 (above) has taken his company from
a one-man operation in his Maryland dorm room to one that can afford a $4 million Super Bowl ad.

Squarespace was born of frustration, when the computer science major wanted to create a website for himself in college during the pre-Facebook era.

“I wasn’t trying to create a business originally, but I wasn’t happy with what was out there,” he says. He had to get page-building software from one company, photo gallery software from another and statistics counters from yet another. A programmer and designer since he was 15, he set out to build his own platform, patenting it with the help of the Hinman CEOs living and learning program.

After a few months of creating website templates, he decided not to offer them
for free, distinguishing him from his competitors.

“We wanted to be the place you go when you want to take this seriously,” he says. “Your website is like your online clothing—it’s how people see your ideas out there. We’ll offer 20 carefully curated, fully customizable templates instead of 20,000.”

Squarespace grew slowly at first. He spent every moment outside of class handling helpdesk tickets and troubleshooting. Casalena convinced his dad to lend him $30,000, then he fed early profits back in to the company, not taking any external funding until 2010.

Now the New York City-based company has hundreds of thousands of paid users, including HBO, Sony and luxury fashion brand Bottega Veneta. Casalena has been named one of Forbes’ “Most Promising CEOs Under 35.” And in February, he aired Squarespace’s first Super Bowl commercial to 111 million TV viewers.

Casalena manages a team of more than 250, and the guy who’s always been more comfortable coding at the keyboard has had a steep learning curve in management. He gave up writing code just last year, though he still participates in “hack weeks” at the company, when the engineering and design teams can work on anything they want.

Sometimes that’s where the best ideas come from.

“Solve your own problems and be your own customer,” Casalena says. “I’m not much of a fan of people starting with wild business ideas just to make money. You should be wishing the world were a certain way.”