SQUARESPACE

In 2003, Anthony Casalena was a student at the University of Maryland and he was annoyed. Building a website meant either learning to code or paying a developer a small fortune.

He wanted something in between. So he built it himself, a tool that let a normal person make a clean website without touching code.

His father lent him about $30,000 to get going. For years he basically ran the company solo.

He wrote the code, answered the support emails, and handled the servers. He did not take venture money until 2010, a full seven years in.

That long bootstrapped stretch is the real origin story. By the time investors showed up, the thing already worked.

Squarespace sells subscriptions. You pay a monthly or yearly fee to build, host, and run your website, and in return you never have to think about code, servers, or hosting.

Drag, drop, pick a nice template, done. They make money the boring, beautiful way, with recurring payments that come in every month.

On top of the basic site, they upsell. Domains, online stores that take a cut of sales, email marketing, appointment scheduling.

By the time it went public, Squarespace was pulling in over $700 million a year in recurring revenue. Sticky software that people forget they are even paying for.

The core product is the website builder and hosting platform, the thing that lets anyone publish a polished site without code. Squarespace Commerce turns those sites into online stores.

The domains business got a massive boost when Squarespace bought Google Domains in 2023, inheriting millions of customers. Acuity Scheduling, bought in 2019, handles appointment booking for service businesses.

There is also email marketing and Unfold for social media content. In 2024 the company sold its restaurant-reservation tool Tock to American Express for $400 million to sharpen its focus on the main platform.

Two things made Squarespace. Design and marketing.

First, the templates actually looked good, which won over photographers, restaurants, designers, and small brands who cared how their site looked. Word spread through exactly the people whose taste others copy.

Second, Squarespace spent huge money turning a boring utility into a famous brand. Super Bowl ads.

Celebrity spots with the likes of Keanu Reeves and John Malkovich. Podcast sponsorships in seemingly every show on Earth.

They also bought their way into new areas, grabbing Acuity Scheduling in 2019 and the assets of Google Domains in 2023, which added millions of domain customers overnight.

The competition is relentless. Building websites is a crowded, bloody market.

Wix, WordPress, Shopify, Webflow, GoDaddy, and a wave of new AI site builders all chase the same small businesses. Squarespace has to keep proving its subscription is worth paying for when free and cheaper options are one search away.

As the market matured, growth slowed, and a slower-growing public company gets punished every quarter. That pressure is part of why Permira could argue Squarespace was undervalued on the stock market and take it private in 2024.

Off the public market, it can chase growth without analysts grading its homework every three months.

Squarespace is a rare bootstrapped-then-backed story. Casalena took no outside money for seven years.

When he finally raised in 2010, Index Ventures and Accel led the way. General Atlantic came in during 2014 and stuck around for the long haul.

The big pre-IPO round in 2021 pulled in crossover heavyweights, including Dragoneer, Tiger Global, D1 Capital, Fidelity, and T. Rowe Price, at a $10 billion valuation.

Then in 2024 the private equity firm Permira bought the entire company for $7.2 billion and took it private. The constant through every one of those chapters was Casalena.

He never lost control of the company he started in his dorm.