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Squarespace: A Dorm-Room Project Worth Billions


You need to do three things to launch a promising career - dream big, find your passion, and devote to it!

What's your next move?

Ensure the crowd is watching, because, at the end of the day, it is all about reputation, quality, and value.

In our case, we're looking into the value of a high-end website.

Laugh at the plainness of the idea all you want, but building a professional website used to be a tough nut to crack.

Fair amounts of money were spent to even jumpstart one, and then, coding got involved, and that was a huge - ah-ah-ah!

When Anthony Casalena came across this gap, finding a way out of the mess became his primary focus.

He'd bring something of value, something to change people's lives- starting with his.

That little something grew into something marvellous, and he called it Squarespace.

Here's an insight into a young man's journey through the dark times and the bright- all in the name of creating thriving industries

Read more about Squarespace below:

Using Technology to Cultivate Joy

Anthony Casalena - sounds familiar, doesn't it?

Countless young entrepreneurs can relate to the success story of a boy who falls in love with technology and grows a company from zero to an empire.

The best thing about it? It all started right out of his dorm room.

Born in 1982, in a small town outside of Baltimore, Anthony flirted with technology from a young age. His flair, mastery and brainpower were first noticed by his father, who would soon open the gates of prosperity for him.

Working for Cisco, a then-worldwide leader in IT, cybersecurity and networking, Anthony's father would always hide his computers around the house, which the boy found amusing and intriguing. Breaking down his father's hidden computers turned Antony into a self-taught programmer by the time he turned thirteen.

During those times, his father was heard-off as one of the best brain-workers for the company, and job offers constantly arrived at his doorstep. However, a multi-tasker by nature, he had zero time for new projects, choring his son with the tasks instead.

Next thing you know, the fifteen-year-old scored a programming job at a Baltimore company.

His duties expanded the skills of a fifteen-year-old. He did everything and then some- from programming scripts to interacting with clients.

Fun while it lasted, bigger responsibilities rose across the horizon.

In 2000, Anthony enrolled at the University of Maryland to study what he was good at- computer science.

Unbeknownst to him, a glorious future was presenting itself, and all he had to do - was look.

Solving a Drawback

One of Anthony's favourite discoveries at the time had to be Joel Spolsky's blog on software development.

In fact, it was thanks to this blog that Anthony had his first business breakthrough.

The lessons not only encouraged him to start something of his own but also gave him an idea of what that could be.


By the time he wrote his first blog, Anthony realized that he couldn't build his own website unless he paid an experienced team to do the job. He could also walk the path less taken, and put together a bunch of software programs himself.

When blogging finally happened for him, Anthony's friends began paying him to create their websites. But, as he piled up with work to the neck, he needed to find a way to help people publish their own work by themselves, so he could have more time to accommodate more clients.

Then another thought dawned on him. Why not create a multi-user service to enable the creation of individual businesses - to whoever cares to run one?

The idea needed two things to be turned into a real concept - previous experience and a server.

Faking his previous experience would help Anthony grow the company. However, he couldn't just plain-invent a server- he had to buy one.

After a long period of persuasion, Anthony's father skeptically invested $30,000 in his son's future.

Armed with knowledge and gear, Antony went on a shopping spree - purchasing one domain after another.

Luckily, the name Squarespace, which he really loved, had not yet been purchased - so he made sure to snatch it up, fast!

A Glance at Success

In 2004, Squarespace was launched.

During the first year, Anthony gave free services to potential clients-to-be whilst buying Google ads. The idea was for his business to grow; however, people took advantage, and it was clear to Antony that some of them would never learn.

So, he shifted the focus onto the people who really wanted to pay - and put every favour a cost.

However, the platform saw its downfall since its first day after such transformation, and Antony needed to rethink strategies. To clear his head, he embarked on a road trip with a friend, where he suddenly had his first customer phone call.

To him, this was the first taste of responsibility, and right there, in the middle of nowhere, Anthony took the call and closed his first deal.

He next needed to buy himself time from his parents who were pushing him for another well-paying job, which is why he graduated a year later than expected.

Just before his graduation, Squarespace earned its first $50,000- not much, but far from bad, either.

Turning a new page, Anthony had now a strong argument against his parents, and could talk them into letting him leave Maryland for the city where dreams came true- the Big Apple.

Even though there was not a single person he knew in New York, Anthony boldly headed towards the metropole and rented his first apartment.

The second year into the company's launch showed slow but steady progress- increasing from $50,000 to $200,000.

As fate would have it, another challenge was laying ahead of Anthony when he left New York to see his family. Back at his apartment, the entire system he built had collapsed and there was no one to help him reboot it.

It was the scariest thought- that you might lose everything you worked hard for.

The moment Anthony entered the apartment, and slid all drives into the computers he sighed, realizing nothing had been lost.

Facing Challenges

By 2006, Anthony was still his own boss and coworker when the company reached its first million in revenue.

Regardless of the generous surge, Anthony reinvested all money back in the company. Sadly, though, this move failed to deliver the progress Anthony hoped for.

But, as there was not a way to turn back, he kept pushing forward.

Eventually, Dane Atkinson, a co-founder of a few other companies, offered Anthony to buy Squarespace. Bright as he was, Anthony never thought of relinquishing the reins from such a mighty player.

On the other hand, Dane wouldn't let such an opportunity slip through his fingers so easily, so he became the first company employee aside from Anthony.

The duo began hiring, and by the end of 2010, Squarespace had its first 30 employees while receiving its first funding round, worth $38.5 million, by Index Ventures and Accel Partners. The money was used to hire greater staff, double the marketing budget, and invest some of it to further develop the software.

Consequently, Squarespace's annual revenue grew to an average of 266% - all within the next two years.

Yet, the times were changing and Anthony realized that his software had become outdated. Seven years had passed since the company's launch and still, nothing was changed, except technology outside its doors.

The only thing that could save him from lagging behind was rewriting an entire software, and empowering websites in whole- not a walk in the park, but it had to be done.

Just like that, Squarespace 6 - an updated version of its predecessor - was launched.

Squarespace welcomed its second funding from another $40 million in 2014, which increased the number of employees to over 500. Its last funding came in 2017 from General Atlantic, worth a dazzling $200 million.

Squarespace: Company Profile

To this day, Anthony remains the CEO of Squarespace, but he is not the only employee anymore. Annually, Squarespace makes an annual revenue of $300 million, which valued the company at more than $1 billion.

Nowadays, Squarespace's 150,000-square-foot headquarters are located in Manhattan and its total workforce count exceeds 1,000 staffers. They aim at solving the user's issues, bearing a very successful record to date.

It all boils down to:

Got a website issue? Squarespace knows a better way.

Need a finely-done website? Squarespace will accommodate you.

Can you trust Squarespace to deliver, every single time? Absolutely.

And that's why it's a successful business model.