“I took the project I was working on at the time (which was a homepage builder I made for my own personal site) and ran with it.”

Interview by Kevin Ohashi of KevinOhashi.com

Anthony Casalena is the Founder of Squarespace. Anthony is a Computer Science graduate from The University of Maryland College Park. His first taste of the startup world was when he was an intern for a VC backed startup called HyperOffice. After only two weeks he became a regular programmer and played a major role at the company where he re-wrote the main product line. Anthony started Squarespace in his dorm room at UMD College Park in 2004 and continues to work on it today.

Squarespace is a New York City based company focused on creating beautiful and powerful websites. They have one of the most advanced (if not the most advanced) WYSIWYG website editor I have ever seen. It gives users full control over the look of the site to a granular level through CSS. They have loaded in many professional themes that people can build their websites on top of while also allowing people to create their own if they choose to do so. They have created modules to do many of the most popular features on websites such as blogging, galleries and more. Squarespace recently raised their first outside investment, a whopping 38.5 million dollar investment from Index Ventures and Accel Partners.

MO:
You’ve recently got a big investment from some major VC firms. You’ve been profitable since the first year of operation.  Why are you taking on venture capital now and what can we expect to see as a result of the investment?

Anthony:
Squarespace has essentially had three lives.  This is the third.  When we started — I ran the business mostly alone for 3 years before reaching the end on what I could really accomplish.  I joined up with Dane Atkinson and Davin Chew to really grow the business into its next stage — and we were very successful doing that.  Before potentially hitting another wall, I wanted to make sure the company was structured to go for the biggest goals possible, and had the right partners to do that.

1) Establish a sense of validation around the business.  The investment helps us attract major talent that we need to ensure Squarespace is a knock out.

2) Establish a board of directors to help guide the business.  In order to retain great talent, it is incredibly comforting to see an experienced board help direct Squarespace through its next phase of growth.

3) Provide operating cash.  While Squarespace is profitable, the investment allows us to invest far more aggressively in R&D and marketing to ensure our aggressive expansion.  The investment also opens the door for M&A activity that was previously off the table for us.

MO:
Squarespace has carved out a valuable niche in the blogging/cms community.  You don’t offer a free plan (only a free trial) and appear to cater to professionals and companies.  What series of decisions led Squarespace to this position?

Anthony:
The decision to do that was from our early experiences actually having a free plan.  Without venture money — you’re really forced early on to focus on your customer base and figure out what’s working and what isn’t.  At the time, our free users weren’t aligned with where we wanted to take the business, and didn’t provide as much of a funnel to paid users as we would have hoped.  So, a decision was made based on the data and we cut them — to ensure all of our fixes and attention was spent with the people who were really investing in our product.  It’s worked very well for us.  

Further, you really have a metric to figure out if the business is a viable one from day one. When your focus is the free user adoption — it can be too easy to look at eyeball growth at the expense of focusing on revenue growth. The paid strategy forces you to make a business.

MO:
You have an almost mythical story of a college kid creating something in his room and turning it into a big company.  You clearly had some startup experience at HyperOffice; was creating your own startup part of the plan or did it just happen?

Anthony:
I learned a lot working at HyperOffice.  There were many mistakes I was intent not to repeat at Squarespace — and I don’t think I would have been as successful without that experience.  I have been a programmer since I was around 15 and always loved the creative part of programming.  There are so many problems in technology still and so many ways to solve them.  It’s an exciting time.

I think the entrepreneurial part of Squarespace just came very naturally — I was involved in a few different experiences where the companies didn’t work out, and I wanted to see if I could do a better job.  I took the project I was working on at the time (which was a homepage builder I made for my own personal site) and ran with it.

MO:
Your title and self description seem to indicate that you’re still mainly a programmer.  Early on, your father was the COO.  How much of a business role do you play at Squarespace?  How did you find and bring in the talent you needed to succeed at Squarespace?

Anthony:
Actually, my father never held an operational role within the company — but his guidance was instrumental in helping me avoid many common mistakes. While my title has been somewhat undefined — I’m still here working an immense amount and helping the company execute.  I’m involved in a very hands-on way in nearly all programming, design, and strategic decisions.  I still write code and design interfaces, as well.

Squarespace today is very much about its team.  The credibility that was established in the early years — the revenue we were bringing in, the completed product, the growth rate — are all what attracted our initial employees.  They’re an absolutely incredible group and working with them is one of my favorite parts of the current company.  We all learn a lot from one another.  I would hope that our future success is what continues to attract others to this environment.

MO:
Squarespace meets the majority of needs for most business clients creating a web presence.  It also eliminates the need for web developers and designers to create those websites in many cases. Do you face any sort of backlash from the developer community because of this and if so, how do you deal with it?

Anthony:
No!  Not at all.  Squarespace has two core target markets:  consumers and developers, and they are related.  Developers are generally making sites for consumers, and Squarespace excels at allowing them to perform that with our interfering.  Without a platform like Squarespace — developers need to be burdened with client sites and running servers.  We remove all of that. Squarespace will never replace the creativity and direction that developers and designers give to their clients.  We think we make everyone’s lives easier.

Most of our upcoming product releases deal directly with developers.  We think if they’re offering the right tools, they’ll create great things for consumers. We want to share in their success doing that.

MO:
Everyone seems to be creating Facebook fan pages and Twitter accounts now.  How will websites remain relevant in an increasingly social world?

Anthony:
These sorts of things are great places to have a presence — and we would recommend everyone has them, but they don’t replace the need to have a home where you’re in complete control.  Squarespace hopes to provide that. You will see many more tie-ins from our core platform to these services in the future, as we facilitate pushing your content out over these various channels.