I'm The Founder Of Squarespace, And This Is How I Work

Like so many heroes of the startup world, Anthony Casalena launched Squarespace from his university dorm room. Now, a decade later, the online publishing company employs a team of 100 and serves 1.4 million websites.

Praised for its elegant design, Squarespace empowers users (coders and non-coders alike) to easily build and customise professional-quality websites. The newest version, Squarespace 6, launched earlier this year and has been called "beautiful", "awesome" and "downright luxurious". We stole a moment out of Anthony's hectic schedule to talk about his workspace setup, go-to apps and favourite tunes.

Name: Anthony Casalena Occupation: Founder and CEO, Squarespace Location: New York, NY Current computer: MacBook Pro with three 27-inch cinema displays Current mobile device: iPhone 5

What apps/software/tools can't you live without?

For the most part, I use Squarespace Note connected to Gmail to record thoughts and tasks throughout the day. I also use Reeder, Pocket and Twitter for keeping up to date with news, and Taskpaper as a personal database. For project management at Squarespace, we use Google Docs and Trello to manage queues and roadmaps. For coding, I use Sublime Text 2 and Eclipse. I still take some notes in a Moleskine during meetings. Pictured at right: Anthony's iPhone homescreen.

What's your best time-saving shortcut / life hack?

My email is my to-do list, and I'm pretty religious about keeping my inbox as close to zero as possible.

So, your favourite to-do list manager?

I use Squarespace Note and my inbox to manage immediate tasks, and Taskpaper to keep a medium-term list. I like having fewer apps, so this works well for me.

What's your workspace like?

I'm constantly trying to eliminate clutter in my life, so you won't find much on my desk beyond my computer, phone, headphones, and a Moleskine notebook. We have an open-plan office, and I sit with team members from engineering and design so they can have easy access to me and vice versa.

What do you listen to while you work?

Unless I'm in meetings, I listen to music while I work. I like everything from hip-hop to the Beatles. I have a pretty extensive personal music collection, so I don't use streaming services. I'm currently listening to a lot of A Tribe Called Quest.

Pictured above: Anthony's desk.

Besides your phone and computer, what gadget can't you live without?

I'm really happy that I invested in a great pair of speakers at home. I have a set of Bowers & Wilkins 802 Diamonds that I use every day.

What's your sleep routine like?

I almost never set alarms -- maybe like once or twice a year. Even when I really know I have to be somewhere by a certain time, I'm able to wake up naturally. When I was younger, I could never get to sleep, and I'd stay up working all night until 5am to 6am and wake up anywhere between noon and 2pm. I keep much more normal hours now, and always try to get six to seven hours of sleep.

What everyday thing are you better at than anyone else?

I think it's important to eliminate the distractions in your life to zero in order to have more time to think about what matters. I try to eliminate clutter in all forms: belongings, apps, processes, etc.

What's the best advice you've ever received?

Take a moment to celebrate victories. I really enjoy what I do, and sometimes it can be hard to stop and appreciate what we've accomplished.

Is there anything else you want to share with readers?

I'm what you might call an anti-hoarder -- my home and office are both very minimalist and free of clutter. I think the Squarespace design philosophy reflects that as well. Our products always maintain a very clean, simple design, and we do our best eliminate the unnecessary.

Want to know more about Anthony? Connect with him on Twitter @acasalena.

We've asked a handful of heroes, experts and flat-out productive people to share their shortcuts, workspaces and routines. Every week we'll feature a new guest and the gadgets, apps, tips and tricks that keep them going. Want to suggest someone we should feature or questions we should ask? Let us know.


Be the first to comment on this story!

Trending Stories Right Now