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8:00AM

Lessons from Squarespace

How did the founder of a comparatively tiny company turn around to make millions and a lasting product? Finding the right people, adapting, and building internally.

Anthony Casalena built the first version of Squarespace because he wanted a better personal website for himself. It’s a common enough story. Drew Houston famously wrote Dropbox’s first line of code on a bus when he realized he left his thumb drive at home. But very few founders have taken Casalena’s path.

While he's run the company for a decade, he didn’t start focusing on explosive growth until six years in. When he did, the company quickly became the first choice for hundreds of thousands of layman web developers, and it snagged a rare brass ring—this year’s buzzy Super Bowl ad that kicked off a new chapter in the company’s history and attracted hordes of new users. Recently, it announced a new fundraise of $40 million to scale even more, bringing its total amount raised to $78.5 million.

So how did Casalena do it? How did he take a company once dwarfed by competitors like Wordpress and Drupal and make it the growing, aspirational brand to watch while continuing to lead development? In this exclusive First Round Review interview, Casalena explains how he achieved every technical founder’s dream.

Get Lost in a Niche

In 2004, there were very few legitimate options for people who wanted to build their own websites without coding. And those that did exist deeply bothered Casalena with their negligence to detail, GeoCities and Blogger among them.

"None of the products out there took style or design into account—which doesn’t work when you’re trying to build your personal identity online," he says. "Your website is where your ideas live. It reflects who you are. And all there was out there were these geeky, bargain-bin sort of services charging $2.99 a month for clunky experiences. So when I started Squarespace, I just wanted to make a site for myself. I never thought it would be a business."

When he started sharing the platform with family and friends, he soon realized he wasn’t the only one stymied by the lack of options in the space. More and more people asked if they could use the tools he had built to create their own sites, giving him the momentum he needed to run a cashflow positive service for three years on his own. Eventually, he was bringing in around $1.5 million a year.

What made the difference for Casalena was his drive to be detailed. When you’re engrossed enough in any area or topic, you develop taste that sets you apart from the crowd, he says. As someone who had taught himself to program from age 15, he knew there had to be a better way to do things, and he pursued that idea at the expense of "getting a real job" without the certainty of a payday.

Six years into the company, this same attention to detail—the kind that you have inherently when you’re building a product for yourself—is what drove Casalena to make the changes he needed to revitalize the company, rise to the top of a new field of competitors, and truly realize his vision to provide a simple, stylish web publishing platform. Hiring was his first stop.

...Read the full article here.

[Image: Flickr user inUse Consulting]

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