Every once in a while, an event reminds me just how much our work together matters. Our evening with Carl Richards was one of those moments…a room full of people opening up, reflecting, and reconnecting with what’s truly important.

A number of you joined us at the Racquet Club in St. Louis for a conversation that was part money, part meaning, and entirely human. Thank you for being there. And for those who couldn’t join in person, we felt your support from afar.

The energy in the room was palpable. People leaned in, shared openly, and allowed themselves to be moved. Since then, we’ve received thoughtful notes inspired by Carl’s sketches. It’s a reminder that a simple line, drawn with intention, can shift how we see our decisions and ourselves.

In my introduction that evening, I shared a story about meeting a couple on vacation whose wife was “famous to some.” That phrase describes Carl perfectly. He isn’t trying to be famous. He’s trying to be useful. Based on your reactions, he was.

The questions I asked Carl reflect the way we think at Hill Investment Group:

• What’s the story behind the sketches that make the complex simple without being simplistic?
• What feelings sit just below our financial decisions?
• How do we align the values we claim with the choices we make?

Carl reminded us that money is rarely the real topic. It’s a doorway into purpose and clarity.

My biggest takeaway from the evening is this:

At Hill Investment Group, our job is twofold. We help clients make the most of their capital, picking up every penny possible through evidence and disciplined implementation. And we help clients make the most of what matters in their lives through goal setting, accountability, and behavioral coaching.

We’ve been doing this work for 20 years, and we plan to keep doing it for 20 more, for a select group of long-view thinkers.

For those outside St. Louis, we want you to feel part of the experience too.

If you’d like a complimentary copy of Carl’s newest book, just email us and we’ll send one your way.

Here’s to a year ahead defined by gratitude, clearer choices, and deeper alignment between money and what matters most.

Take the Long View,

We’re delighted to share that Hill Investment Group will host a very special evening with Carl Richards—internationally recognized author, speaker, and podcaster—on Wednesday, November 12, 2025, at The Racquet Club in St. Louis, which will be one of Carl’s first stops on his national book launch tour for the release of his latest work Your Money: Reimagining Wealth in 101 Simple Sketches.

Many of you know Carl through his Behavior Gap sketches and writing. His simple drawings and powerful insights remind us that clarity often comes from seeing complex ideas made beautifully simple.
This gathering will include cocktails, heavy hors d’oeuvres, and a lively conversation with Carl about his newest work and what it means to “take the long view” in both money and life.

Event Details
The Racquet Club — 476 North Kingshighway, St. Louis, MO 63108
Gathering at 6:00 PM | Program Begins at 6:30 PM | Concludes at 7:45 PM
Attire: Jacket, No Tie. No Denim, Please.

A few seats remain. Please RSVP by November 7, or call us at (314) 448-4023.
Do you want something like this in webinar form or in your city? Email me.

This month marks 20 years since we opened Hill Investment Group on June 6, 2005. What began as a bold idea between two friends has grown into a boutique firm serving clients in 34 states, with over $1 billion in assets under management (as of June 2025), and a talented team that now stretches from San Diego to Brooklyn.

It’s a milestone we’re proud of, and yet, we feel like we’re just hitting our stride. Our ambition today remains the same as it was at the outset: to become the leading boutique evidence-based firm in the country. That means earning your trust every day, guiding you through market swings, and standing with you through the milestones that matter most.

We’ll be celebrating this anniversary throughout the year, with reflections, lessons learned, and maybe even a few fun (non-investment!) predictions about what’s to come. If you’d like to hear how it all started, listen to this 2019 podcast episode where Rick Hill and I revisit our early days.

And here’s a favorite image from our recent team and family gathering—a reminder that what we’re building isn’t just a firm, but a community grounded in shared values and complementary skills.

Thank you for the continued trust you place in us. It’s a responsibility we’re honored to uphold.