From a college dorm room at the University of Maryland to a $6 billion public company. That's what Anthony Casalena, the founder of Squarespace, was able to accomplish in 18 years. Back in 2003, Casalena wanted to make a website for himself but quickly realized that to put together different aspects of a website (domain name, hosting, blog), he needed to combine different services. That was way too clunky so he decided to create his own service. After borrowing $30k from his dad for a couple of data center servers, Squarespace was born. After college, he drove to Manhattan and got a fourth floor walk-up apartment that he found on Craigslist. (looks like he was a Murray Hill bro too)
On Wednesday, Squarespace went public valuing Casalena's stake at $2.4 billion. Although Squarespace had an underwhelming first day of trading, closing at $44/share, below its $50 IPO price, Casalena at 38 years old, became the latest tech entrepreneur to join the three-comma club, joining the founders of Affirm, Roblox, Coinbase, Bumble, UiPath and AppLovin, companies that IPO'd earlier this year. Squarespace also followed in the footsteps of Spotify and Coinbase, and went public via a direct listing avoiding the high af Investment Banker fees.
Short Squeez Takeaway: The reason Casalena still owns such a large stake in his Company is because he bootstrapped (no outside investment) his business till it reached $10 million in revenue before taking any outside capital. The was helped by the fact that Squarespace was a profitable company early on, unlike many early-stage tech companies. At that time Getty Images approached him to sell but he declined and took capital from Index Ventures & Accel, and remained in control. The lesson here is that if you really believe in what you are building, keep at it, it can make just a few billion dollars of difference in a few years.