The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Squarespace Founder, Anthony Casalena on Scaling Squarespace from Dorm Room To Public Company with over $700M in ARR, The Decision to Direct List over Traditional IPO or SPAC & What Changes When You Go Public?
Oct 8, 2021
Anthony Casalena, the innovative Founder and CEO of Squarespace, shares his journey from dorm room beginnings to leading a public company with over $700M in ARR. He discusses why he chose to bootstrap for years, emphasizing the impact it had on his mindset. Casalena reveals the strategic decision behind opting for a direct listing over traditional IPOs or SPACs, and shares insights on the complexities of being a public company CEO. He also reflects on the transformative effects of e-commerce growth in the wake of COVID-19, highlighting new opportunities for the future.
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Squarespace's Dorm Room Beginnings
- Anthony Casalena, frustrated with existing website builders, created Squarespace in his dorm room.
- He wanted an all-in-one platform with a design-centric approach, prioritizing aesthetics.
Not Always a Grand Vision
- Grand visions for startups are not always present at the start.
- Early reactions to Squarespace indicated its potential, despite the challenge of selling the importance of design.
Bootstrapping to $10M ARR
- Anthony bootstrapped Squarespace with $30,000 for seven years, focusing on organic growth and reinvestment.
- The company reached a $10 million run rate with 30 employees before taking institutional funding.
