How this lone founder was able to grow their business from nothing to $200 million in revenue

How Anthony Casalena Built Squarespace from Scratch into a $200 Million Business

In 2003, Anthony Casalena was a regular student at the University of Maryland, with no knowledge of web design or programming and very little money. By 2016, he had built Squarespace into a $200 million revenue-generating platform that powered over a million websites. Here’s how he did it:


1. Solving His Own Problem (April 2003)

  • The Problem:
    Anthony wanted to create a personal space on the internet but found existing solutions too complicated or unattractive.
  • The Solution:
    With no formal training in design or programming, he taught himself the skills he needed to develop a platform that addressed his needs.
  • The Mindset:
    Anthony didn’t start with the intention of building a business; he was simply solving his own problem.

2. Launching Squarespace (December 2003)

  • The First Version:
    After months of development, Anthony released the initial version of Squarespace.
  • Initial Funding:
    To host the Squarespace code, he borrowed $30,000 from his father to purchase computer servers.

3. Building a One-Man Business (2004–2007)

  • Solo Hustle:
    For the first three years, Anthony ran Squarespace entirely by himself. He:

    • Wrote the code.
    • Handled customer support and marketing.
    • Managed the business operations.
  • Differentiating Squarespace:
    • Unlike competitors like Drupal, WordPress, and Joomla, Anthony targeted users who valued beautiful, simple design, rather than focusing solely on developers.

4. Early Success and Growth

  • Profitable by Graduation:
    By the time Anthony graduated college, Squarespace was already earning over $1 million in revenue.
  • Expanding the Team:
    • Anthony moved to New York City and grew his team to around 30 employees.

5. Scaling Up (2008–2010)

  • Improving the Platform:
    With the help of two team members, Anthony revamped the codebase to make it scalable and better suited for broader use.
  • Securing Funding:
    • In July 2010, Squarespace raised $38.5 million from Accel Partners and Index Ventures, marking a turning point in the company’s growth.

6. Accelerating Growth (2014–2015)

  • Additional Funding:
    • In April 2014, General Atlantic invested $40 million in Squarespace.
  • Strategic Acquisition:
    • In October 2014, Squarespace acquired Brace.io, a company specializing in cloud-based website creation tools, to further enhance its capabilities.
  • Reaching New Heights:
    • By 2015, Squarespace’s revenue had reached $100 million, and the company employed 550 people.

7. Achieving $200 Million in Revenue (2016)

  • A Milestone Year:
    By 2016, Squarespace had more than doubled its revenue to $200 million, cementing its position as a leader in the website-building industry.

Key Takeaways from Anthony Casalena’s Journey

  1. Start by Solving Your Own Problem:
    • Squarespace began as a personal project to address Anthony’s need for an easy-to-use, beautifully designed website platform.
  2. Do the Work Yourself:
    • Running the business solo for the first three years allowed Anthony to stay deeply connected to his customers and product.
  3. Differentiate Your Product:
    • Squarespace targeted users who prioritized design and simplicity, standing out from developer-centric competitors.
  4. Invest in Scalability:
    • Early efforts to make the platform scalable enabled Squarespace to grow without being constrained by its technology.
  5. Leverage Funding Strategically:
    • Raising capital from respected venture firms like Accel Partners and General Atlantic allowed Squarespace to accelerate growth and expand its capabilities.

The Legacy of Squarespace

From a college dorm room to a globally recognized platform, Anthony Casalena’s story is a testament to the power of persistence, innovation, and self-reliance. His journey proves that even with no prior knowledge, starting small and focusing on solving real problems can lead to extraordinary success.

Source: Entrepreneur.com

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