Carl Richards, a longtime friend of the firm and someone many of you know through our events, books, and conversations over the years, generously sent this video in honor of the 10th anniversary of Odds On. Carl’s endorsement was featured on the front cover of the book, and his encouragement has meant a great deal to us from the very beginning.

For newer readers, Carl is the creator of the Sketch Guy column and is widely known for his work helping people think more clearly about money, behavior, and what really matters. He is the author of several books, including The Behavior Gap and his newest release, Your Money, and he also hosts podcasts including Behavior Gap Radio and 50 Fires. We hope this video brings you the same joy it brought us, especially if Odds On has shaped your thinking in some meaningful way too. Carl has a new book released not long ago called Your Money, reach out to us if you’d like a copy. 

Carl Richards Always Delivers

While your mail may be delayed, Carl Richards always brings it home.

As Matt shared above, Carl has a rare gift for connecting money and emotion through beautifully simple sketches and memorable stories. At our recent event, he walked us through several concepts that sparked intense, productive conversations. In Carl’s words, the sketches often serve as “conversation grenades”… in a good way. Translation: they jump-start meaningful dialogue and help people have clearer, more honest conversations about money and life.

On November 12, Matt Hall led a live conversation with Carl at the Racquet Club in St. Louis, exploring themes from Carl’s latest book, Your Money: Reimagining Wealth in 101 Simple Sketches.

If you were unable to attend the event in St. Louis, please email us here to request a complimentary, signed copy of Carl’s book, which each attendee received.

If you’re interested in a webinar or in-person event with Carl, email me at buddy@hillinvestmentgroup.com. We’ll do our best to arrange it.

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,