Why This Founder Decided to Scrap Years of Work to Radically Reinvent His Product

As Anthony Casalena grew Squarespace, he was forced to recognize when he could no longer do everything himself--and when it was time to radically reinvent the product he had spent years developing.


Growing a company occasionally can require switching gears and letting go of nearly everything you've been doing--even if it's years of work. Anthony Casalena, founder of the website-building-software company Squarespace, knows this as well as anyone. The more successful the business becomes, he says, the quicker it will transform into something new and different from what you started as a solo entrepreneur.

When Squarespace started, it was just Casalena programming in his dorm room at the University of Maryland. For three years he built and managed the company himself, even after he had graduated and moved to a tiny New York City apartment in 2006. But eventually, he says in a new Inc. video, it becomes clear that you can only make so much progress on your own.

"I was very comfortable doing a lot of the aspects myself," he tells Inc. editor James Ledbetter. "It just started to get overwhelming. You spend three months working on something and you realize you just spent the month doing accounting, and customer support, and X, Y, and Z, and [you are] not moving this thing forward."

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