ISSUE – Apr. 12 | Why Squarespace’s Founder Finally Raised $39 Million After Holding Out for 6 Years

In 2016, Anthony Casalena’s company generated more than $200 million in revenue, but the founder of website-building platform Squarespace doesn’t want to spend a penny he doesn’t have to.

How did you know your idea could be a viable business?

I started programming Squarespace in 2003. Originally, I wasn’t intending to start a company. I was creating it because I wanted to make a website for myself, and I was really frustrated that it required so many kinds of software. I didn’t understand why all those things weren’t in one place. I quickly realized that the thing I was making for myself was something other people could use.

You asked your dad for $30,000 to buy servers for the business. How did that conversation go?

My dad recalls some version of his saying to me, “We’ve always supported you. We’re always ready to back your ideas.” I remember it more like a huge fight. He didn’t understand why I needed two servers instead of one. I have to credit my mom a little bit for helping me talk him into it. [ Inc. ]