Anthony Casalena
Founder & CEO, Squarespace
Bootstrapped Squarespace from a dorm room to a website platform past $700M in annual recurring revenue; advocate of capital efficiency and opinionated design.
Key arguments & positions
- Champions bootstrapping and capital efficiency — grew Squarespace profitably for roughly six years before taking outside investment.
- Favored a direct listing over a traditional IPO when going public in 2021.
- Emphasizes curated, "opinionated" design over unlimited customization as a product philosophy.
Accomplishments
- Founded Squarespace in his dorm room in 2003.
- Grew it past $700M in annual recurring revenue.
- Took it public via direct listing (NYSE: SQSP) in 2021.
- Led its take-private sale to Permira (about $6.9B, closed October 2024) and stayed on as CEO — Squarespace is privately held again.
Papers & key writings
No books or essay collections — his public voice comes through interviews such as 20VC and First Round Review.
Links
In the library
Nothing of theirs is filed in the hub yet. Browse the full library.
Recommended next
Hand-picked from the hub based on what Anthony Casalena covers.
Ryan Holmes
Founder & Former CEO, Hootsuite. Writes on entrepreneurship, leadership, and building businesses from scratch; founder of the League of Innovators nonprofit.
Why this: Covers Entrepreneurship and Bootstrapping too
SBA Business Plan Tool
This free government guide helps you research, structure, and write a business plan from start to finish. You can use downloadable templates and federal market data to calculate startup costs and create a plan for lenders.
Why this: Covers Entrepreneurship and Small business too
2026 Annual Entrepreneurship Assistance Centers Conference
The annual conference of New York's Entrepreneurship Assistance Centers, held Wednesday, October 21, 2026, 9:30 AM to 5 PM at Civic Hall in New York City. The EAC network provides training, coaching and support to new and aspiring entrepreneurs across New York State. Registration is through Eventbrite.
Why this: Covers Entrepreneurship and Small business too
World's Biggest Business Competition
A free four-week online business competition starting 24 October 2026, with over $1 million in prizes, live expert support, tools and business playbooks for people starting or growing a business.
Why this: Covers Entrepreneurship and Small business too