Squarespace: A Platform Built on Patience, Persistence, and Profits

The story of Squarespace highlights the journey of a solo founder, Anthony Casalena, who turned a dorm-room project into a billion-dollar web design empire. Without initial outside investment, Casalena grew Squarespace with a focus on profitability, an uncommon approach in tech startups. Here’s a look at how he took Squarespace from a personal need to a publicly traded company empowering millions to build their online presence.

From a Dorm Room to New York City

In 2003, while studying at the University of Maryland, Casalena sought to simplify the web-building process. Frustrated with juggling various tools for hosting, page building, and blogging, he built Squarespace to combine these functions into a single platform. Starting as a one-man operation with a $30,000 loan from his parents, he launched the company from his dorm room and quickly saw traction. By 2004, Casalena moved Squarespace to New York City to expand the brand professionally, gradually building a small team to support the platform’s growth.

Growth Through Revenue – Not Venture Capital

Squarespace’s early growth was fueled solely by its revenue—a choice that set it apart from other startups that relied on heavy funding rounds to scale quickly. Casalena’s choice to prioritize sustainability over rapid expansion enabled Squarespace to stay profitable from the start. In 2014, with Squarespace’s success firmly established, Casalena took on $78 million in funding to further scale operations, marking a turning point for the platform. By remaining disciplined in its growth, Squarespace had established itself as a reliable player in the web-building market, appealing to personal users and businesses alike.

Building Beyond Websites: E-commerce and Branding

Squarespace’s mission expanded as it began supporting e-commerce features, allowing small businesses to manage and sell products online seamlessly. This capability quickly gained traction with entrepreneurs looking for all-in-one website solutions. By 2018, Squarespace reached a valuation of $1.7 billion and employed over 800 people, making it a major player in New York City’s tech scene. Casalena also capitalized on marketing opportunities, like sponsoring the New York Knicks—a move that placed the Squarespace logo on the team’s jerseys and bolstered its public profile.

A New Chapter: Going Public

In 2021, Squarespace went public on the NYSE with a valuation exceeding $6 billion, marking a significant milestone. The IPO represented years of patient growth and steady profitability, rewarding Casalena’s unique approach of focusing on long-term sustainability over hyper-growth. Today, Squarespace remains a popular choice for individuals and small businesses seeking an easy-to-use web-building platform, with millions of users worldwide.

Overview in Numbers

• Founding Year: 2003

• Founder: Anthony Casalena

• Headquarters: New York City, NY, USA

• Employees: Over 800 as of 2018

• Peak Valuation: Above $6 billion post-IPO in 2021

• Business Model: Subscription-based, offering plans for personal use, e-commerce, and business features

• Notable Partnership: New York Knicks jersey sponsorship