Yesterday I turned forty-four years old. I’m a huge fan of retrospectives, thus a quick a look back at the past year.


  • Coached four baseball teams (two in the spring, two in the fall) — playing 48 regular-season games plus playoffs.
  • Supported three kids playing hockey — two in a house league, another in a learn to skate program. Roughly 60 games, plus a President’s Day tournament in Wisconsin, and playoffs. I often run the scoreboard at home and help with the penalty box on the road.
  • Competed in the Chicago Triathlon along with my son Jack.
  • Rode 4K miles. Enjoyed riding the North Shore Century (Evanston, IL), Apple Cider Century (Three Oaks, MI), and Levi’s Granfondo (Santa Rosa, CA).
  • Read hundreds of stories with the kids. This time is truly a treat.
  • Celebrated 14 years with the one and only Erin Marie Judge.
  • Enjoyed Thanksgiving in Wisconsin, Christmas at home in Illinois, and New Years in Florida.
  • Celebrated Erin’s 39th, Jack’s 10th, Caelin’s 8th, Evie’s 6th, Eleanor’s 3rd, and Avery’s 1st birthdays. Our cakes baked per year (CBY) metric in the Judge household continues to move up and to the right.
  • On a community front, saw progress on two big initiatives: (1) completion of the Chicago lakefront trail split to help make biking, running and walking safer and easier along the lakefront, and (2) completion of the first phase of the Navy Pier flyover. We’ve been advocating for these projects at the Active Transportation Alliance (I’m a board member) for many years as part of our mission to make biking, walking, and public transit safe and easy options for the 10M folks that live in the Chicagoland area.
  • Continued mentoring startups as part of Techstars. To date, I’ve worked with 24 companies going through the Techstars Anywhere program. I’m currently a lead mentor for StoryTap, a great Canadian company bringing video to online reviews. I’ve recently started helping Parabol too.
  • I haven’t invested in any companies in the past year but excited to see momentum with Draftbit. Check them out if you’re building a new app…I’m happy to make an intro.
  • Work-wise, we launched in Canada, raised a round of financing, rebranded as Arrive, and continued hiring great people. After 18 months, I finally feel like we have the right people, processes, and plumbing in place to grow the way we want to. It’s an exciting time for the team.

A year in pictures

Here were some of my favorite moments:

Erin and Evie celebrating my 44th at Cafe Selmarie

Erin And Evie

Eleanor drawing me

Eleanor Drawing

A pair of brothers — love the support here

Hockey Brothers

Caelin’s class before a school play

Caelins Class Play

First dance with Eleanor

First Dance With Eleanor

Caelin’s first (Mite) hockey season

Caelin Hockey

A coworker grabbed this shot in Seattle — I was texting Erin about the amazing view

At Day One In Seattle

Onesie from the University of Michigan College of Engineering

Avery Umich Dot Edu

Taken at the Google office heading up to my first ORD Camp (woot!)

Ord Camp

Celebrating Avery’s first birthday

Avery Birthday

My nephew Joe and his girlfriend Claire helping us celebrate Caelin’s birthday

Josiah And Claire

Erin and Avery — early morning on the beach

Erin And Avery

Evie showing off her newly assembled Ukulele

Evie Ukulele

Dinner with our growing extended family — extraordinary folks to boot

Family In Florida

Touring the Everglades

Evie In Everglades

Walking with Avery

Avery In Naples

Rinsing off after a morning trip to the beach

Evie And Eleanor At Beach

Isabelle (cousin), Evie, and Eleanor baking one of the birthday cakes

Erin Cake

Evie took this photo and I love it— it’s a good representation of me

Portrait Taken By Evie

Taken at the Fullerton el stop before ‘The Fantastic Mr. Fox’ play

Evie Eleanor Jack Fantastic Mr Fox

Decorating the office— we’ve since swapped out all of the lights (a big upgrade)

Arrive Office

Watching the Bears play the Rams

Caelin Erin Jack Bears

Family day at the MCA

Jack Caelin Eleanor Mca

Celebrating my nephew Jerzey’s birthday

Jerzeys Birthday

Adorable moment. Gotta watch out for these young bucks and their savvy french fry tactics.

Eleanor With Boy

Thanksgiving at the office

Matt Perille Arrive Thanksgiving

Taken on a run with Caelin to Metropolis Coffee. 100% correct.

Vote Mf Er

Evie started playing hockey this year as a River Pup

Evie At River Pups

Avery during her nine-month check-in

Avery At Doctors Office

Midnight Circus in Chicago

Midnight Circus Lincoln Square

Grabbing a burger with Caelin after a baseball game — always laughing with this kid

Caelin Flexing

The Chicago lakefront path separation in progress

Chicago Lakefront Path In Progress

Riding with friends

Riding With Friends

Levi’s Gran Fondo — Santa Rosa, CA

Levis Gran Fondo

The first day of 4th grade, 2nd grade, kindergarten, and pre-kindergarten (those cheeks!)

First Day Of School

Jack at the finish line of the Chicago Triathlon — so proud!

Jack At Chicago Triathlon

Caelin learning how to sail in Newport, RI

Caelin Sailing

Evie, Sam, and Eleanor. Cousins!

Sam Evie Eleanor

The kids with their Uncle Joe, Aunt Liz, and cousin Emma

Joey Liz Emma Jack Caelin Evie Eleanor Avery

Grabbing hibachi with Jack and Caelin

Jack And Caelin

Hunting trolls with Evie

Evie With Camera

Celebrating Jack’s birthday

Jacks Birthday

Thank you to all my friends and family for your continued love and support!

Previous editions: 43, 41

This post was originally posted on Medium