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​Crain's New York

May 18, 2011 View Original Article

Top Entrepreneurs 2011

Founder: Anthony Casalena

Frustration sparked Anthony Casalena’s dorm-room startup. He launched Squarespace Inc. in 2004, while he was a senior at the University of Maryland, after having an unexpectedly difficult time designing his website. He’d found that integrating all the disparate components—software for displaying photos, blogging, analytics and the like—was a cumbersome process.

“It was just so annoying,” said Mr. Casalena, now 29.

So, as any self-respecting computer science whiz might do, he created his own way to pull in all the pieces of the puzzle. When friends started asking to use the program for their websites, Mr. Casalena realized he had stumbled on a business opportunity: a one-stop publishing platform. It enables clients to create high-quality websites and integrate other services—which now include Flickr and Twitter—easily and seamlessly.

After spending about eight months refining the software, Mr. Casalena borrowed $30,000 from his father, a former sales exec at Cisco and Hewlett-Packard, to buy servers. He housed them in New York, knowing that he’d set up shop here.

“The creative spirit of the city fits very well with Squarespace,” he explained. “We see design as something fundamental to our business, so New York is a very natural home for us.”

After taking an extra year to graduate and work on the business, he moved home to northern Maryland and spent six months saving money before finally settling in Manhattan five years ago.

Mr. Casalena experimented with offering a free service, like archrival WordPress, along with a paid option. But he decided early on to nix that model and go after a more serious user. 

The 50-employee company offers three levels of service, charging $12 to $36 a month, serving “tens of thousands of users,” Mr. Casalena said. Clients include both individual bloggers and companies such as fashion firm Marc Ecko Enterprises and cosmetics retailer Kiehl’s. Squarespace, which has been profitable since 2005, posted 2010 sales of $10.2 million—up 95% from the year before.

The ability to appeal to both ends of the spectrum is one of the team members’ major accomplishments, said Jeffrey Carr, executive director of NYU’s Berkley Center for Entrepreneurial Studies.

“They’ve found a way to combine ease of use and one-stop shopping for everyday users and still provide value to professional developers,” Mr. Carr said. “That’s rare.”

Squarespace got a big boost in July 2010, when it earned one of the year’s largest rounds of venture capital in New York: $38.5 million in funding, led by Accel Partners and Index Ventures. Mr. Casalena, the majority shareholder, formed a five-person board that includes Dominique Vidal, an Index Ventures partner; Andrew Braccia, an Accel partner; and Jonathan Klein, CEO of Getty Images.

Mr. Casalena is using the money to build his next version, which he promises will offer a “drastic improvement in the experience of using the software.” He expects to launch it this summer. Ultimately, he said, “we hope to grow the number of publishers using our site to millions.”

This isn’t Mr. Casalena’s first startup experience. As a high school senior, he worked on design and implementation for, an online provider of communication and collaboration software.

“It really helped get the business to the next level,” he said.

With that vision and moxie, it’s a wonder he waited until his senior year in college to launch a business.

Squarespace has reduced its carbon footprint by buying carbon offsets and purchasing energy that’s supplied entirely by wind turbines.

—Anne Field