Goodbye, Squarespace

Even when change is elective, it will disorient you. You may go through anxiety. You will miss aspects of your former life. It doesn’t matter. The trick is to know in advance of making any big change that you’re going to be thrown off your feet by it. So you prepare for this inevitable disorientation and steady yourself to get through it. Then you take the challenge, make the change, and achieve your dream.
— Harvey Mackay

Twice in my career I've taken leave and found it difficult to return. The first time, when my son was born. The second, this past week. I was on Cape Cod for our annual holiday and felt really, truly present for my family in a way that I don't feel often enough. It also happened in Brazil when we went for the World Cup, so this has been a summer of reflection about what kind of dad I want to be and what kind of relationship I want my family to have with me.

When I joined Squarespace four years ago next week, Lila was four and Remy was weeks old (Kiki wasn't even an idea). All parents know that the one constant with your kids is that whether they are filling you with joy or driving you up a wall, it all goes very, very fast. Lila starts 3rd grade next year and is closer to a teenager than a toddler. A friend reminded me recently that work is a rubber ball and family a glass ball. The work ball can bounce. I am making the choice to go take care of my precious glass ball.

I am a builder, and Anthony and I have certainly had a productive four year relationship. From 24 employees to nearly 400. From modest revenue to double digit growth multiples. From a handful of engineers to marketing, HR, business intelligence, customer service, QA, dev evangelists, to a Super Bowl ad and beyond, all the pieces are now in place. I did my job: I built an organization and worked myself out of a job.

Of course, when you have an amazing product, it's much easier to be a successful businessman. I'm most proud of how we brought all our disciplines together – product, marketing, customer service – to deliver the unparalleled customer experience that drives our growth.

Next Adventure

Being a manager and being a founder's lieutenant have a lot in common. In my philosophy both are necessarily selfless and often unfortunately thankless. You elevate your people by putting their needs first, by devoting yourself to helping them meet their goals, by helping to define their ambition, and by providing them the support and coaching they require to be their best self. You derive your satisfaction from seeing others succeed, giving away the credit and the ideas, and sometimes taking the blame.

I love coaching people, and have a solid track record helping young companies frame their ideas and build their foundations. I've become a more active investor and advisor over the past 18 months and I plan on digging deep to help a few early stage companies cross the chasm. I've already got my first two projects lined up. If my nose for investment opportunity matches my ability to build and scale nascent businesses, then perhaps I have found my next calling.

Thank You Squarespace

Thanks first and foremost to Anthony, who has taught me so much, most importantly the power of focus and saying no. He turned this type-a multi-tasker into a rank-ordered list lover. To my team, who repeatedly showed me what passion and ingenuity were capable of and whose development and success fill me with pride. To my peers on our leadership team, who each challenged me to be my best self and taught me valuable lessons that will pay dividends in my future endeavours. And lastly to my friend John, who always returns my focus to the glass ball. Squarespace has been a wonderfully life-changing experience.

I'm long Squarespace. The team is remarkable, the product pipeline strong, and the leadership we brought in is what gives me the confidence to depart. I'm a proud shareholder that can't wait to see the company scale new heights.