Squarespace Founder: Convincing Dad to Lend $30K for Seed Was a ‘Big Fight’

Coming out of college with a job offer from Google sounds like a win, but Anthony Casalena decided to go in a different direction. Convincing his dad that turning down Google and creating his own company was the more lucrative way to go, however, took a bit of persuasion.

The University of Maryland grad set out to solve a problem widely for himself, creating a platform that would allow him to easily fashion a website. From there- he borrowed $30,000 from his father to buy servers and venture out on his own—creating Squarespace.

“In 2004, the Web was a very different thing—there was no Google Chrome, it was predominately Internet Explorer. We wanted to first and foremost give ourselves a foundation to grow, and a build that we were excited by,” says Casalena.

And grow they did—the startup today is nine years old, and received a major $38.5 million investment from Accel Partners and Index Ventures in 2010. Nine months ago, the company launched a total redesign—Squarespace Six—and is currently doing so well that it is not seeking further investment, Casalena said.

The redesign also allows the platform to cater to vertical markets, including consumers, ecommerce sites and service businesses.

“We tried to cater to as many of them as possible,” Casalena says. “With that new investment, we were able to bring a board in place, and really take the company to a new level.”

Today, Casalena has 125 employees working for him, and said among some of his business regrets was hiring too quickly when starting out.

“I could have looked for [advisory] help a bit sooner, and did the initial hiring a bit slower,” he said. “I don’t think I would have been as stressed out. I think back then, launching, I didn’t know what I was getting into. I was intimidated, stressed out and overwhelmed by the responsibility of it all.”

But he is glad he forged onward as an inexperienced founder, and hopes other young entrepreneurs do the same.

“I think there are all kinds of reasons that people perceive entrepreneurship as out of reach for them,” he said. “But [entrepreneurship] gives people the opportunity to look at the world a certain way, and there are great resources to help people along.”

Getting into the entrepreneurial game shouldn’t be about money or fame, Casalena said—instead it needs to come from a deeper place.

“It’s like coding. You may want to make a project, or think making a company would be fun. But make sure you are doing it because you want to make the world a certain way, and you can’t stand if the world isn’t that way,” he said. “Because you  will have to deal with other unfortunate realities of what creating a business is like, so you have to have the strong position that the world needs what you are creating.”