Recently, our Hill team gathered at Round Hill (a storied boutique resort) in Jamaica to mark an important milestone: 20 years of serving the families who have placed their trust in us.

It was a true celebration.

Yes, islands, especially Jamaica, have a way of slowing you down. But what made the time meaningful was the chance to pause together and reflect on what has been built over two decades and, more importantly, why it was built in the first place.

As I looked around the group, I kept coming back to something Rick Hill impressed upon me early on: great firms endure because of people who care deeply, take quiet ownership, and hold themselves to a high standard, whether anyone is watching or not.

That spirit was unmistakable throughout the trip.

There was plenty of laughter. Real connection. The kind of easy camaraderie that only develops over years of working alongside people you respect and trust. We also invited spouses to join us, and that added a dimension I did not fully appreciate until I saw it unfold. Our work at Hill asks a great deal of the people who choose this path. Having spouses there brought more context, more gratitude, and more heart to the experience. It reminded all of us that the strength of Hill is supported by families who quietly stand behind the scenes.

The pinnacle for me came on our final night together. One by one, team members stood up and shared their favorite memories from their time at Hill. Some were funny. Some were deeply moving. All of them pointed to the same thing: a group of people who genuinely care about one another and about doing work that matters.

In that moment, it felt like we had quietly crossed into a new level of shared commitment. Not a finish line. Something better. A deeper understanding of what we are building together and why it matters.

Each year, during our time together, we present the Rick Hill Award. It is one of the traditions we hold most dear because it honors the kind of steady, values-driven contribution that Rick modeled from the very beginning. I am excited to share more about this year’s recipient below.

20 years in, Hill has never been stronger. We remain focused, grateful, and energized about the road ahead.

If you have been with us for part of this journey, thank you. Your trust is the reason moments like this matter.

And the most meaningful part of the story is still ahead.

Take the long view,

Matt