A CEO explains how his leadership style changed as he went from a 21-year-old on his own to leading a $200 million company

Squarespace CEO Anthony Casalena
At a certain point, you have to learn to delegate, says Squarespace CEO and founder Anthony Casalena. Squarespace

In the early days of Squarespace, CEO and founder Anthony Casalena wore many hats.

He would spend his days tackling a litany of random tasks, including writing code, penning marketing copy, and even answering customer service tickets.

“I had this disposition to go fix things myself,” Casalena tells Business Insider. “I was an engineer and I wanted to engineer my way out of everything, and, at some point, that can only get you so far.”

For a while, however, that hands-on attitude worked for Casalena, who founded the content management system in 2003 as a 21-year-old college student at the University of Maryland. By avoiding a too-rapid expansion, he says he was able to keep his business financially sound.

But, ultimately, his workload wasn’t sustainable. Casalena says he woke up one day and realised that he had missed the mark on a number of long-term goals he had been working on. He couldn’t continue to juggle so many tasks and run the company, which is today a $US200 million enterprise.

“It was like, ‘OK, I’m really just spinning my wheels here,'” he says. “I’ve got to change something. So I started hiring people.”

Although he caveats that his own experience isn’t necessarily universally applicable, Casalena says that being slow to hire and delegate did have one major upside.

“It gave me experience with all aspects of the business,” Casalena says. “To the extent that I could, when we were bringing people in after a couple of years, I had some idea of what it took to do certain jobs. I also think that hiring out of pain kept the business very lean for a long time. The business probably took longer to grow than other people would have had the stomach for, but I think that hands-on nature has been really positive.”

By delegating work and growing his team, Casalena says he learned how to better communicate his expectations and manage a group. He now leads a team of more than 650 employees, spread across offices in New York, Dublin, and Portland.

Today, Casalena has adopted a more minimalist, focused management style.

“Knowing how to just declutter things and move the unimportant things out of the way has been really important for success,” he says. “The things that made you successful in the past don’t necessarily make you successful in the future.”