2025 Year In Review
Friends,
And just like that… 2025 is over.
As I scrolled through my iPhone camera roll, Google Calendar, and Strava log, I couldn’t help but wonder…
will this Year in Review be remembered as a bop, a flop, or get recycled into AI slop?
Because I am a sucker for a good list, this newsletter is organized numerically and chronologically. So… pour yourself a fresh cup of coffee, egg nog, Guinness Zero (IYKYK), or something more potent, and let me tell you about my 2025.
As always, thanks for reading.
7 Best Days of the Year
These are the seven days of 2025 that stood out when reflecting on the year.
Bandit Field Trip March 26
My run club, Bandit Racing Team, had a record number of Boston Marathoners this year, and we decided to do something special for one of the final long runs of the training cycle. We chartered a 50-passenger bus, got dropped off at the Argo Livery, and had no choice but to run the scenic route back to Erratic Ale in Dexter, totalling 15 - 20 miles, depending on the runner’s ambitions.
What made this day so special was the collaboration with Huron Waterloo Pathways Initiative. As part of a matching fundraising effort, our run club donated over $2,000 that day to help complete the Border2Border Trail. Beginning in 2024, I pledged to donate $250 to HWPI for every home I sell. In 2025, that translated to $7,500 in direct donations to HWPI.
Jersey City Marathon April 13
My 19th marathon proved to be one of my slowest (3hr 32min) and most humbling… but this trip was incredible, all because of my fellow travelers : Adam Hughes, Jack Miller, and Mikel Haggadone.
Our first day featured a Central Park run, Broadway production of Glengarry Glenross, late night NYC pizza slices, and a $130 Uber ride back to our Airbnb in Jersey. Day two was a classic Jersey experience: a shockingly delicious greasy spoon diner, angry drivers, depressing strip malls, and an ineffable charm that we couldn’t quite put our finger on.
At the halfway mark of the marathon, I noticed that my comrades (Adam and Mikel) were suspiciously quiet and mellow. After some unprovoked giggles, it became clear that these idiots were using 5mg gummies as aid station fuel – they still managed to outkick me in the final mile.
Post-race, we traded war stories at a bar recommended by Colleen Stone, and capped off the trip with a three hour game of Scrabble. We like to tell ourselves that our boys' trips get super wild, but in reality they are actually pretty nerdy and wholesome.
Portraits & Peonies May 31
A few years ago, I met an amazing photographer at one of my listing photo shoots. Lewis and I had been looking for a way to collaborate, and a colleague (Michael Barbour) suggested hosting a portrait session in The Arb when the peonies were in full bloom.
The results were some A+ level Tinder profile pics, engagement photos, head shots, and family portraits. We also learned that fresh coffee from Hyperion and the majestic peony garden at dawn is an unbeatable combination.
If you ever need a professional photographer, I know a guy.
Huron 100 Pregame Show June 7
It was my childhood dream to become a sports broadcaster. But my voice never really deepened, and this fantasy took a backseat for a more practical vocation. To this day, I care just as much about the nuances of the announcer booth as the games on the field.
So when Race Director Dan Hughes asked me to anchor the pregame show for Huron 100 (no one asked me, I negotiated this as a condition of my race sponsorship), broadcasting on their live stream was a true bucket list item unlocked.
Despite repeatedly asking Jesse Sweeney where he was on January 6 (no one can say for sure), I’ve been invited back for 2026.
One Year Anniversary with Chelsea Oct 4
We ate pumpkin pancakes, read our vows, dried our eyes, and marveled at just how good we have it.
It’s hard to describe how special this day was, and the entire year has been, but I hope that people reading this get to experience the same joy that we do. Chelsea, I love you, and am so grateful to be with you.
Jasper & Kinley Reunion Oct 21
One of Jasper’s oldest friends, Kinley, was in town from Denver, and they picked up right where they left off in 2019. Complete with a round of zoomies reminiscent of their Western Mass days, these senior dogs rekindled their puppy energy for a truly magical hour in Jasper’s backyard.
Jasper has slowed down quite a bit in 2025, but is aging gracefully. His biggest champion and best friend, Chelsea has made it her mission to keep our buddy healthy, comfortable, and always feeling loved.
Zing Train : The Zingerman’s Experience Oct 15-16
I came out of this workshop inspired by the Zingerman’s approach to service, business, leadership, and relationships.
My three main takeaways were :
Great organizations have a clear vision and purpose for existing. Being different from your competitors is not only good, it’s the whole point of having your own business.
Businesses have to give their customers a compelling reason to support their organization. Leaders need to stay a step ahead and wake up every day thinking about how they can enhance their clients' experience.
There are no shortcuts or magic bullets to building something great. It takes hard work, discipline, and a commitment to your overarching vision.
No one will ever convince me to go to a “real estate Mastermind” conference in Scottsdale or Fort Lauderdale. However, I would love to take another Zingerman’s class next year, and would be delighted to collaborate with someone who is reading this newsletter.
If you are curious, hit me up.
5 New Rituals in 2025
In each of these cases, the joy came from experiencing something new with people I care about.
Lunches with Nephew Jack
Jack is a junior at UM, and the best lunch companion in town. He is punctual, the most insightful 21 year old I have ever met, and he appreciates good food. To date, we’ve dined at Kosmo’s, NYPD, Miss Kim, Palio, and Spiedo.
NPR Sunday Puzzle
For the past few months, Chelsea and I have gotten really into listening to, and solving the Sunday Puzzle, hosted by Will Shortz. She is much more skilled than me, but it’s a real thrill when I manage to find the answer first.
Trying New Coffee
We just have a basic drip coffee maker, but have loved trying out new roasts this year. I think it started last Christmas when we scored over a half dozen bags to grind through. After that, we just kept buying different beans to try. To date, I think we’ve tried over 30 different roasts this year. My favorites have been Stumptown Hundred Mile, Hidden Grounds : India, Intelligentsia El Gallo Blend, and a Danish coffee that I received in a bag swap with Michael Berry (if you are reading this, please text me the name of the roaster).
Book Club
Unsurprisingly, this has led to reading books that would have otherwise been off my radar. My three favorite reads have been James by Percival Everett, Starter Villain by John Scalzi, and The Wide Wide Sea by Hampton Sides.
Urquhart’s Tree Farm U-Cut
Some friends took Chelsea and I to Urquhart’s last year, and we loved this experience. We did it again in 2025, and now it’s been codified as a family tradition. For the uninitiated, you take a wooden sled and saw out into the tree farm, find the perfect tree, cut it down, strap it to the roof of your Subaru with twine, and white knuckle it home. If you want to meet us there next year, we’ll be there on the Saturday after Thanksgiving.
