How I Built This with Guy Raz Squarespace: Anthony Casalena
Mar 4, 2019
In this episode, Anthony Casalena, the founder of Squarespace, shares how he transformed a simple website-building tool from his college dorm into a billion-dollar company. He discusses the challenges of scaling the business and the emotional toll of leadership. Casalena opens up about the struggle of relinquishing control while hiring his first team. He also reflects on the pivotal moments that shaped Squarespace’s growth, including the successful leap into podcast advertising and the launch of Squarespace 6, which redefined user experience.
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Dorm-Room Launch
- Anthony built Squarespace in his University of Maryland dorm room in 2003 and launched it by late 2003.
- He bought domains, named it Squarespace, and ran servers to get the product online with $30K from his parents.
Blogging As Product Anchor
- Anthony saw blogging as an entry point for broader publishing tools and extended it into full website features.
- He focused on integrated publishing (blogs, pages, galleries) rather than competing with heavy desktop tools.
Avoid Freemium Resource Drain
- Avoid unlimited free plans that never convert and consume resources.
- Charge a modest fee to focus product and server resources on paying users.