Squarespace is a New York based company that offers a hosted blogging platform of the same name. No longer a start-up, the company has been running for 7 years, has been totally self-funded, and is profitable.
Squarespace is the platform that I have been using for the past several months to publish my /Message tech blog, and other websites I maintain, like my Edgewards conference site and the non-profits Microsyntax.org and 301works.org. My familiarity with — and admiration for — the company’s technology led me to contact the founder, Anthony Casalena, and learn about his plans for the company, as well as the story behind Squarespace. I am covering my technical analysis of Squarespace in a companion to this post at /Message (see Squarespace, An Advanced Modular CMS), while here I want to just focus on the conversation I had with Anthony earlier this week. However, I will characterize the product, briefly, as a sophisticated blog-oriented content management system, offering a great variety of built-in modules — like blogs (called ‘journals’), forums, pages, and forms — as well as very rich access controls. It’s most direct, well-known competitors is Wordpress.
Anthony started working on the first version of Squarespace in college, at the University of Maryland, when he grew disenchanted with the various alternatives available for building and maintaining websites. He grew the business and managed it in Maryland for 3 years, by which time the company was already making $1M/year. The top line for Squarespace has been recently more than doubling annually, Anthony said, which will put growth in the past three years near the 700% mark.
The story of Anthony building something he personally needed, and the way that he did so without outside funding, reminded me of 37 signals. Anthony agreed with that characterization, although he hasn’t worked to keep the company artificially small, as Jason Fried and the 37 signals team did. “I think there are some things that you can do with more people in the company that just couldn’t be done — or done very slowly — if you don’t grow.”
Anthony moved the company to New York 4 years ago, so he is no longer a newcomer. In his viewpoint, he relocated to NYC at a time when ‘no one cared about tech’. He wasn’t trying to be some sort of contrarian, building a tech business in a city that could care less. He wanted to live in NYC because of what it offers outside of its support for tech: a huge mix of different communities — fashion and finance, art and media — and very diverse.
Anthony is very much the New Yorker now. “I am a 24×7 guy, always out at night. And although I like the Bay Area, I didn’t like the groupthink of Silicon Valley.” Anthony worries that people might be moving to NYC now for “the wrong reasons”, by which he means to just hang out with other tech folks rather than all the other things that NYC offers, and especially its diversity.
Three years ago he brought Dane Atkinson as CEO to lead the business, which has allowed Anthony to roam from one aspect of Squarespace business to another, focussing on what is most important at the time, whether that is programming, product planning, or developing channels.
The company has been approached by investors, but has not taken any funding. Anthony says that while he doesn’t see the necessity for raising capital for Squarespace at this point, he is actively considering the strategic partnerships that may help accelerate Squarespace’s growth
The community of users is approximately half individuals and half businesses. The nature of Squarespace means that it attracts individuals who are “do-it-yourselfers”, who want to have relatively sophisticated blogs or websites without having to be programmers or even have advanced design chops. Businesses often are steered to using Squarespace by web designers who gravitate to the technology because it can be turned over to clients once developed and running, and then the clients can update the content without having to use designers or website developers to add or modify the content.
Because Squarespace is a rich and largely self-contained system, it differs in philosophy from Wordpress, where much of the functionality is provided by various third party plugins. Anthony is unimpressed with this architecture, and believes it is outmoded and dangerous. “Who wants to update a company’s content management system by adding patches to the software? It’s a security mess.” He also wonders if the Wordpress approach to supporting both a hosted product and a standalone self-hosted version of the technology creates a strategic conflict for Wordpress. “Some of what they do, I would never do,” he stated.
Anthony is deeply involved in the development of the next generation of Squarespace, called Squarespace 6. This sounds like a dramatic step forward in flexibility and sophistication, based on his description. I have yet to see it, although I hope to do so in the next few weeks. Given the strides that Anthony and Squarespace have made to date, I expect that my mind will be blown.
Anthony is growing in new directions, and has started to think about becoming an angel investor, especially for other New York startups. He is a perfect fit for that role, considering the the continued growth at Squarespace, and his personal odyssey from dorm room startup to New York success story.
