On Heartbreak
If you’re going through hell, keep going.
Two choices, same message, both true.
“If you’re going through hell, keep going.”
“It will all work out in the end. If it hasn’t worked out, it’s not the end.”
On One-on-Ones
Every one-on-one is a personal development opportunity.
It is a manager's responsibility to be regularly available for (and not to miss) a one-on-one and a team member's responsibility to show up and own the agenda. The meeting is owned by the employee because it is her professional development we are focused on. We're not here for a status update – email can handle that fine – but rather to open the pathways that lead to repeat success, removing blockers, and providing a safe environment to nurture not-fully-baked ideas.
My expected agenda is straightforward. First, focus on success. Discuss your wins since we last met. How have you moved the business forward? Be sure to have shared any necessary KPIs or project updates one day prior to meeting face-to-face. Second, air your blockers and frustrations. The most valuable data I can capture is how the org and, more importantly, I am preventing you from being successful. Third, and this is the fun part, what do you want to spitball? Use me as a sounding board to think through ideas, no matter how zany, before you are ready to present them to the team. Lastly, discuss the needs of the team and how you can contribute to addressing them.
Every one-on-one is a personal development opportunity.
It is a manager's responsibility to be regularly available for (and not to miss) a one-on-one and a team member's responsibility to show up and own the agenda. The meeting is owned by the employee because it is her professional development we are focused on. We're not here for a status update – email can handle that fine – but rather to open the pathways that lead to repeat success, removing blockers, and providing a safe environment to nurture not-fully-baked ideas.
My expected agenda is straightforward. First, focus on success. Discuss your wins since we last met. How have you moved the business forward? Be sure to have shared any necessary KPIs or project updates one day prior to meeting face-to-face. Second, air your blockers and frustrations. The most valuable data I can capture is how the org and, more importantly, I am preventing you from being successful. Third, and this is the fun part, what do you want to spitball? Use me as a sounding board to think through ideas, no matter how zany, before you are ready to present them to the team. Lastly, discuss the needs of the team and how you can contribute to addressing them.
Frequency should not be dictated by a recurring event on the calendar, though bi-weekly is a good pace and you should never go four weeks without a one-on-one. Sometimes you need to meet weekly, other times monthly. If I reserve the proper amount of office hours each week, my team members can pull the one-on-one as needed. I recommend booking an hour. It's better to use ten minutes and leave time over than to only book 30 and find yourself not getting all the face time you deserve.
I like to keep a shared Google Doc for each team member. It's easy to add a new agenda to the top of the doc, and to take notes during the meeting for reference. Obviously, it's also convenient for noting items that need to be covered at the next meeting. Notes and follow-through are critical in all meetings, big and small.
I'll discuss my role in providing you feedback at these meetings in a later post. You should never have to ask for it.
Goodbye, Squarespace
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.
“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.”
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.
Our Favorite Books
Courtesy of my wife, the favorite books in our house, by age.
Courtesy of my wife, the favorite books in our house, by year:
Birth
The Carrot Seed by Ruth Krauss
Here Are My Hands, by Bill Martin Jr and John Archambault
Open the Barn Door, by Christopher Santoro
1 Year Old
The Snowy Day, by Ezra Jack Keats
Who’s Hiding?, by Santoru Onishi
The Mitten, by Jan Brett
2 Years Old
Richard Scarry’s Cars and Trucks and Things That Go, by Richard Scarry
Bunny Cakes, by Rosemary Wells
A Good Day, by Kevin Henkes
3 Years Old
My Friend Bear, by Jez Alborough
The Giant Jam Sandwich, by John Vernon Lord
Cupcake, by Cherise Mericle Harper
4 Years Old
Piggy Bunny, by Rachel Vail
The Frog and Toad Collection Box Set, by Arnold Lobel
The Hello, Goodbye Window, by Norton Juster and Chris Raschka
5 Years Old
The Miraculous Journey of Edward Tulane, by Kate DiCamillo
Library Mouse, by Daniel Kirk
Brave Irene, by William Steig
6 Years Old
My Book About Me, by Dr. Seuss
Ramona Quimby, Age 8, by Beverly Cleary
Duck for President, by Doreen Cronin
7 Years Old
The Gardener, by Sarah Stewart
Stone Soup, by Marcia Brown
James and the Giant Peach, by Roald Dahl
8 Years Old
Justin Case: School, Drool and Other Daily Disasters, by Rachel Vail
A Wrinkle in Time, by Madeleine L’Engle
Matilda, by Roald Dahl
Street Art in Rio
Driving around Rio is a feast for the senses, from the trees to the graffiti.
I never seemed to have my phone out at the right time. Driving around Rio is a feast for the senses, from the trees to the graffiti. Here are a few of the shots I managed to grab.
