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

As many of you know, each year at Hill Investment Group we present the Rick Hill Award.

It has quickly become one of the most meaningful traditions inside our firm. Importantly, it is not an award for the loudest voice, the biggest title, or the most visible contributor.

This year, during our team’s 20 year celebration, we had the special privilege of announcing the award with Rick himself in the room. That made the moment even more meaningful for all of us. Rick has always believed the true strength of our firm lives somewhere quieter. In the people who take ownership without being asked. Who care deeply about others. Who show up the same way whether anyone is watching or not.

We are grateful to the clients and teammates who submitted such thoughtful and generous nominations. The letters reflected something we feel every day. Hill is filled with people who take their responsibility to clients seriously. We do not take that lightly.

As we read through the nominations, a clear pattern began to emerge. Different writers. Different perspectives. Yet the same name kept appearing, along with the same themes.

One nominator described this person as “an old soul in a young man’s body.”

Another wrote about someone who stays calm under pressure, steps in to help outside his lane, and does it all without seeking recognition.

We also heard about the way Jack naturally takes interns and new hires under his wing, helping them understand not just what to do, but why it matters. That resonated deeply with us because Jack himself began his Hill journey as an intern.

The story that stayed with us most involved a client phone call.

The client was facing something far bigger than money. Instead of quickly handing the call off, Jack stayed present. He listened carefully. He connected. He shared honestly from his own life and reassured the client that Hill would be fully there in that moment.

As the nominator wrote, it would have been easy to say, “I’m so sorry to hear that… here’s Nell.” But that is not how Jack operates.

That kind of behavior is not found in a job description. It is a choice. And it reflects exactly the spirit Rick modeled when he helped build this firm.

By the time we finished reading the nominations, the choice was unmistakable.

We are proud to share that the 2025 Rick Hill Award recipient is Jack Gardner.

Jack, thank you for how you show up for clients, for teammates, and for Hill. You make the firm better in ways both visible and invisible.

And to our clients, thank you for the trust you place in our team every day. Moments like this remind us that Hill has never been stronger, and people like Jack are a big reason why.

Take the long view,

Matt

Tammira Philippe is the embodiment of the American dream. The first in her family to go to college and now the President and CEO of Bridgeway Capital Management, Tammira has paved a purposeful path for herself and her organization. Hear her conversation with Matt. Listen on Apple or click below.

Read the full transcript here.