A Day in the Life of Squarespace's Founder and CEO

In 2004, Anthony Casalena's project of building a personal webpage took off when others saw what he had created. Over a decade later, Casalena's project has grown to one of the most talked about startups in years. Squarespace's growth and innovation can only be chalked up to Casalena's ingenuity, focus on design, and perseverance. 

Squarespace's Headquarters in NYC

In 2003, a college student was sitting in his dorm room trying to build a site that included more than a simple WordPress template could give him. The design focused undergrad realized that in order to achieve what he saw in his mind’s eye, he’d have to start from scratch. This undergrad was Anthony Casalena, the founder and CEO of Squarespace. Today, the company has grown to over 580 employees who help design, assist, and manage the millions of websites that have been created on the Squarespace platform.

We got a chance to see what it’s like to work as Anthony at Squarespace’s new headquarters in New York City—a space where Anthony’s focus on design can literally be seen

Planning From a Blank Slate

Q: Where did the inspiration for Squarespace come from? Had you ever thought about the idea of starting a company before and what do you wish you had known beforehand?

A: I began working on Squarespace back in 2003 because I ran into two problems when building a website for myself. First, creating a site meant cobbling together a mix of disparate software (back then, everything was separate: blogging platforms, page building software, hosting, traffic analysis). I didn’t want to do that, so I started building something unified. Second, I realized that my website was going to be how people perceived my ideas if they found me online. As someone who has always cared about good design, I wanted my site to look good, but there were virtually no platforms that cared about design with respect to the web.

I didn’t initially intend for Squarespace to become a full-fledged company, but quickly realized that the problem I was solving for myself was something other people could use a lot of help with. Squarespace arose from trying to solve that need. In the early days of Squarespace, I ran all of the parts of the business by myself—everything from setting up the servers in our data center to creating AdWords campaigns. I did the coding, marketing, advertising, customer care, design, infrastructure setup, and more. While I do none of those things now, in a hands-on capacity, having done them has really helped me gain a deeper understanding and be empathetic to what is required for all of those different jobs. But sometimes I wish I had spent more time early on team building versus trying to do everything on my own. While the mindset of solving problems myself was really great for a period of time, you eventually need to give everything away. I could have started on that a bit earlier on.

Design All Around

Q: What interested you about coding and web design?

A: I’ve always been interested in computers, and I’ve been programming since I was around 15 years old. At that time, there was actually no web at all, but it was easy to see how big of a deal web technologies would become when they started to emerge and how they’d eventually change the way we communicate and deploy applications. Programming gives you this immense freedom—you can use your computer and a text editor to make almost anything. It’s an amazing creative outlet.

Enjoying Who You Work With

Q: As you hired people, how did you see your role change within the company? Did you experience any difficulties in letting go of certain tasks and delegating them to others?

A: I'm in a constant transitional state from being the person that creates, to supporting the many people that now create. I’ve had trouble letting go of certain things in the past, but that just usually means I haven’t found the right people or figured out how to articulate what I want from a role.

A Tree Grows in Squarespace

Q: How do you think technological advances will change the way Squarespace is used? What are some things Squarespace is looking to do in the future?

A: The biggest one that we’re amidst is obviously a large shift to mobile device usage. That’s already greatly affected how many of us consume content, and it is also altering how many approach authorship of content. To many, having a desktop computer is something they no longer need to rely on so heavily, and in some cases, may no longer need at all.

In the broader technological landscape, we’re constantly making use of the most modern technologies in order to build the best platform possible for our users. That approach manifests in many forms. Sometimes it’s us integrating with pioneering companies that take previously opaque/complex processes and make them easier (like what Stripe has done for payment processing); other times it may look like us leveraging a cutting edge visual technology in our templates that helps users stand out and stay ahead of the curve.

Anthony's "Office"

Q: What would you recommend for graduates to do in order to get into tech or creative companies like Squarespace?

A: While we have a very active recruiting network, I would definitely encourage anyone interested in us to apply directly. The more you can show us, the better. While we definitely want to understand your career from a resume perspective, we love seeing personal projects and anything else that can help us understand where your passions lie.

Afternoon Meeting

Q: When hiring, what are some key traits you look for in a candidate?

A: We really prefer intellectually curious, hands-on creators who are good communicators and have collaborative dispositions. We look for proactive individuals who don’t shy away from new projects and are capable of bringing new ideas to the table. One of the most important qualities we test for at Squarespace is empathy—in interviews, we will ask people to present arguments for two opposing sides. We want to make sure our employees are passionate about our product, believe in our mission statement, treat others with respect, and, most importantly, really love what they do.

View From the Top

Q: What advice would you give to college students inspired to start a business while still in school (rather than waiting to pursue ideas after graduation)?

A: Everyone’s situation is different, so I’m not sure I have generic advice. I used my years towards the end of college to space out my classes to the point where I had enough time to focus on starting Squarespace. No matter if you’re in school or if you have a job, it’s important that you’re always spending a major amount of your time on whatever inspires you.