In the late 1990s and early 2000s, building a website was a tedious task best suited for engineers with a strong knowledge of HTML, Java, and other site building tools, preventing the participation of everyday individuals and businesspeople. Then, in 2003, University of Maryland undergraduate student Anthony Casalena started building Squarespace—a user-friendly, drag-and-drop website builder—from his dorm room.
His motivation was the same frustration others felt trying to participate in the World Wide Web, and he hoped to make the new practice known as “weblogging” easier. Now, the 39-year-old programmer turned entrepreneur is preparing his company for its Wall Street debut and his stake has him poised to join the dorm room billionaires club. This places Casalena in the same conversation as Napster bad boy Sean Parker, computing billionaire Michael Dell, and social media demigod Mark Zuckerberg, all of whom launched their empires from a university residence hall. But just because his venture is ready to go public, doesn’t mean that Casalena is set to lean back and count zeros.
Casalena is still the CEO of Squarespace almost two decades after its dorm room launch, and as such he is the company’s guiding light. He recently led the company’s acquisition of Tock, a Chicago-based restaurant reservation startup that has successfully pivoted to the takeout business during the coronavirus pandemic. The company has found success by catering to small businesses, fueling innovations in eCommerce, and constantly improving user experiences, all while helping to create over a million websites. The turn from site building to eCommerce is a natural pivot, and about a quarter of its customers are web stores of some kind. Not only did COVID-19 create a market for new online shoppers, it forced many businesses to make the big leap into digital transformation—and Squarespace is just one significant beneficiary of the changes.
On the cusp of Squarespace’s direct listing on the stock market, Casalena stands to make a fortune. With a 33% stake in his company, Forbes estimates his net worth at around $3 billion on a $10 billion valuation. On top of personal monetary success, Casalena’s company has won accolades for being a top workplace for women, parents, and anyone looking to launch a career in customer management software development, among more. He’s made it onto Fortune’s 40 Under 40 List with a year to spare, so it’s safe to say that Casalena’s future will be one of his own design.
