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Anthony Casalena

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Anthony Casalena, founder and CEO of Squarespace, grew up in Monkton, Maryland. His interest in computers developed young, and he repeatedly broke his father’s computer while playing around it as a young boy. Eventually this frustrated his father, who worked for Internet companies, enough that Casalena’s parents bought him a computer of his own. He learned to program around age fifteen, initially focusing on user interfaces.

While studying computer science at the University of Maryland, Casalena tried to make a personal website, but found all the existing services wanting. Finding that what he desired didn’t exist, and knowing he had the skills to create it, Casalena began building Squarespace, launching it from his dorm room in 2004. Backed by a $30,000 loan from his father, Casalena ran the company alone for three years. In 2005, he graduated from University of Maryland with a BS in Computer Science and moved to New York, taking the company with him.

Squarespace has grown extensively since its dorm room beginnings. The company, which consists of a website builder, blogging platform, and hosting service, raised a $38.5 million Series A investment round in July 2010, and another $40 million in Series B funding in 2014. By July 2014, the once one-man company employed 280 people.

Companies and Investments

Squarespace (Founder, CEO)

99designs (Investor), Milk (Investor), TinyCo (Investor)

Lessons Learned

“I think that when I'm honest with myself, again, I can think back then and think, ‘Okay. Well, I was always really good at being the engineer and being a programmer and building this thing, getting it running and doing all the jobs myself.’ And eventually, there was a point in the company's history where that skill to do all that wasn't a strength, it was a weakness, and what I really needed to be doing is not falling back on that engineering strength, but actually, going out there and trying to build a team and get redundancy in place from a personnel perspective. And that's a really hard thing to do. And I think getting pushed outside of your comfort zone and dragged forward and realizing that you can't do it all yourself is really an important time.” – Anthony Casalena, on recognizing you can’t do everything, on Inc.com

“The number of non-starts and setbacks leading up to that event were numerous—I was very young. You just have to keep going. I literally ran Squarespace alone for three years in the beginning, doing work spanning from customer support all the way to systems engineering. I understand all of those parts of the business well. I’m a very ground up thinker—my goal in year one was never to be a very large company or to land a huge investment. It was always about getting methodically to the next level.” – Casalena, on taking things one step at a time, in an interview in Stated Magazine


Inspiring Quotes

I didnt have time to write a short letter, so I wrote a long one instead.

Mark Twain

Anthony Casalena's Quotes

I think getting pushed outside of your comfort zone and dragged forward and realizing that you cant do it all yourself is really an important time.

Anthony Casalena

It’s okay to scale ambition.

Anthony Casalena

I’m inspired by anyone who really takes the time to craft a relatable experience. Apple does it with computers. Guys like Ian Schrager do it with hotels. It doesn’t matter. Anyone really willing to say “this isn’t good enough” and push through—push for something that surprises people. I like that.

Anthony Casalena

The number of non-starts and setbacks leading up to that event were numerous—I was very young. You just have to keep going.

Anthony Casalena

It’s easy to throw out bad ideas, but to throw out really good ones is hard.

Anthony Casalena

Influential Books

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