Billionaire Profile
Anthony Casalena
Global Rank
#1855

Image: Public domain | via Wikimedia Commons

Anthony Casalena

CEO, Squarespace
US
Real-Time Net Worth
$2.1B
As of December 2025
Age
43
Source
Software
Industry
technology
Citizenship
US

Biography

Anthony Casalena is the founder and CEO of Squarespace, a leading website building and hosting company. With an estimated net worth of $2.1 billion, Casalena's wealth stems primarily from his stake in Squarespace, which he founded in 2003. His career began with a vision to simplify website creation, launching Squarespace from his dorm room. His achievements include leading Squarespace to become a publicly traded company and later taking it private. Casalena's focus on design and user experience has been pivotal in Squarespace's success. He resides in Monkton, Maryland and is known for his focus on product development and his deep involvement in the company's engineering and design teams.

Wealth Over Time

In-Depth Profile

Early Life

Anthony Casalena was born on April 24, 1982, in Baltimore, Maryland. He attended Hereford High School and later pursued a Bachelor of Science in Computer Science at the University of Maryland, College Park, graduating in 2005.

Rise to Success

Casalena founded Squarespace in April 2003 while he was a student at the University of Maryland. He began developing the platform in his dorm room, driven by his dissatisfaction with the existing website-building tools. He launched Squarespace to the public in January 2004. The initial funding for Squarespace came from a $30,000 seed fund from his father, and a small grant from the university. Casalena served as the sole employee and developer for the company in its early years. Squarespace received its first round of venture capital funding in 2010, with $38.5 million from Index Ventures and Accel Partners. Squarespace went public through a direct listing on the New York Stock Exchange in May 2021. In October 2024, Squarespace was taken private by Permira.

Key Business Strategies

Squarespace's success is rooted in a user-friendly, design-focused approach to website building. Casalena emphasized an all-in-one solution, integrating tools for blogging, statistics, and page-building with an aesthetically pleasing interface. From 2009 to 2012, Squarespace's revenue grew at an average of 266% yearly. By 2015, the company had 550 employees. The company's business model is subscription-based.

Philanthropy

Specific details about Anthony Casalena's philanthropic activities were not found in the search results.

Career Milestones

2003

Founded Squarespace

Started the website building platform from his dorm room at the University of Maryland.

2004

Launched Squarespace publicly

Made the platform available to the public after initial development.

2007

Revenue of $1 million

Squarespace reached $1 million in annual revenue.

2011

Recognized as a Top Entrepreneur

Named one of Crain's New York's Top Entrepreneurs.

2013

Named as a Most Promising CEO

Named one of America's Most Promising CEOs Under 35 by Forbes.

2014

Recognized as a Coolest Entrepreneur

Named one of Inc.'s 35 Under 35 Coolest Entrepreneurs.

2021

Squarespace went public

Squarespace went public on the New York Stock Exchange.

2024

Squarespace taken private

Squarespace was taken private by Permira.

Philanthropy & Social Impact

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REAL initiative: Not available

$XB: Not available

REAL description: Not available

Business Philosophy & Leadership

Notable Quotes

""There was no all-in-one solution, so building a functional one meant cobbling together a mix of software for blogging, statistics and page-building, and Web-hosting services,""

Leadership Principles

Design-centric Approach

Focus on creating visually appealing and user-friendly website designs to attract customers.

Emphasis on all-in-one solutions

Integrating various web-building functions into a single platform to simplify the process.

Prioritization of Sustainability

Focusing on long-term growth and profitability over rapid expansion in the early years.

Controversies & Challenges

YEAR: Not available

REAL controversy: Not available

REAL description: Not available