Know Where The Money is Going Before You Ask For It

Jon Spenceley

Squarespace founder Anthony Casalena didn’t necessarily know he wanted to start a business, but he did have a clear concept of what he wanted. “I was trying to make my personal website and I wasn’t satisfied with any of the existing services” said Casalena in interview, “I had a very clear concept of what I wanted to create and how I wanted to do it, so becoming an entrepreneur was the natural next step.”

Casalena founded Squarespace in 2003 because he was unsatisfied with the available web publishing options, and it has since expanded into a platform that powers both personal and business websites. Casalena designed Squarespace to provide a one-stop solution for web publishers at a time when multiple solutions from multiple providers was the norm. “At the time, you had to seek out and cobble together a mix of blogging software, statistics software, page builder software, and web hosting just to get a coherent-looking site published online,” he said, “Instead of patching something together from a number of different sources, I decided to create a product that looked great and offered all the necessary elements to build a professional website.“

Although Squarespace was founded in 2003, the same year as open-source blogging platform WordPress, Casalena considers the Version 5 update in 2008 to be the company’s biggest milestone. “It was a major overhaul of the existing interface, not to mention one of our first long-term projects. Our mission has always been to make innovative web design accessible to anyone regardless of technical ability. By making our product easier and more intuitive to use, we successfully reached a much broader consumer base.”

While building Squarespace, Casalena said that being self-sufficient was a very important factor. “It’s important for a company to be able to operate out of its own income. Squarespace has been profitable since its inception, and the resulting financial independence has afforded us the freedom to develop products within our own time frame.“ He also believes in taking an active, personal role in supporting customers, saying “I answered support for three years when I started Squarespace, and it was incredibly helpful to understand how that process works by actually doing it. To thoroughly understand the ins and outs of your business, you have to put in the time.”

Squarespace did raise funding in 2010, pulling in $38.5 million in Series A funding from Index Ventures and Accel Partners, but Casalena cautions entrepreneurs looking to raise money from investments. “Be really sure you know what you want to do with that money, because it’s not free,” he said, “One of Squarespace’s greatest strengths is that it existed for eight years without any major outside funding. Because of that, we were able to take the company in the direction we wanted — a product-minded company that values timeless design and long-term thinking — without any overwhelming outside influences.“ Casalena has been on both sides of the investment table, having invested in several projects, but he does not consider himself a serious angel investor. “I support projects from time to time, but I’m not actively seeking out deals.”

For the projects he has invested in, which includes 99designs, and Milk, Casalena looks for two critical components. “Technology companies should be run by technology-minded people, and the founders must be solving an issue or problem they are personally invested in, rather than chasing a profit-driven concept. Starting a company and making it successful requires an incredible investment in time and effort — most people will not make it through unless they’re driven to solve something for themselves.”

For entrepreneurs, Casalena’s biggest piece of advice is to be strategic about how time is spent. “You need long-term thinking in addition to the ability to manage your time on a smaller scale,” he said. “Some startup companies place a huge emphasis on being thrifty and doing things in the most cost-effective way possible. Though I understand the benefits of that approach, I believe you should spend the money on certain necessities that will ultimately save you time and resources. In the early years of Squarespace, I invested in a lot of infrastructure from commercial vendors that had great support systems, so I didn’t have to worry about learning how to operate and sustain free alternatives.”

Casalena is excited for the future of Squarespace, including the launch of Squarespace 6. “It offers the ability to create a unified web presence that can be managed via mobile apps, synced with all major social media channels, and look great on any device. We’re really proud of the work we’ve done, and are looking forward to sharing it with the public.”