Last month, I wrote that David Booth’s new book, Stay Calm, would launch on September 1, and with a lot of travel planned, I thought I’d dig into the book before our November 10, 2026, webinar (see “Upcoming Events” below), with David.

As a long-time fan of Dimensional, our primary strategic investment partner, and someone who’s followed the firm and its founders since 1997, I thought I knew a lot about David Booth, Co-Founder and Chairman of Dimensional. I was wrong.

In addition to learning many more details about the confluence of timing, luck, and people coming together at the University of Chicago in the late 60’s and early 70’s, which led to the founding of the first, truly data and evidence-based investment firm in America, I learned about the person behind the numbers and what excites him beyond the science of investing.

In particular, David’s passion for philanthropy has grown along with his net worth, and he feels strongly about giving back. You can read the book yourself to learn the details of the specific dollar amounts, which are significant. However, the “why” is what’s interesting to me. His gift to the University of Chicago was a gift to provide thanks to the place that allowed him to learn so much and meet the people who would lay the foundation for, and join him in his future success. And David wanted to ensure that the opportunity remains for future students as well.

David is also a major art collector. But as he stated himself, “I don’t buy art as an investment. I buy it because I like it.” He goes on to say, “I like happy art, which means that when I walk by it, I smile. And I really love when other people see a piece of art and smile too.” That’s not what I expected to hear from someone who believes so strongly in “data & evidence” and rational thinking. That said, David goes on to explain how he asks himself many of the same questions he would use to evaluate an investment strategy, including “Is it likely to endure over time?” That sounds a lot like taking the long view.

The bigger lesson. David is a sharer. Upon his death, David intends to donate his 50+ acre estate and dozens of outdoor sculptures to the public. When David paid more than $2.5 million for the original “Rules of Basketball” (yes, the real, 13 hand-written rules as penned by Dr. James Naismith), he donated them to the University of Kansas, his undergraduate alma mater. The list goes on.

To learn the entire story, request a complimentary copy of Stay Calm by emailing Annie Hall at annie@hillinvestmentgroup.com. Keep reading to learn about our upcoming webinar!

The best part of our work is the relationships we build with our clients. This series celebrates those relationships by highlighting the interesting people behind the portfolios. This spring, several members of our team had the opportunity to visit Larry West at his remarkable Route 66 Museum, Campbell’s Service, in Pacific, Missouri.

What began as Larry’s appreciation for America’s “Mother Road” has grown into an incredible collection of vintage service station memorabilia and Route 66 treasures, all thoughtfully displayed in a restored building along Historic Route 66. The museum is a labor of love, filled with carefully curated signs, gas pumps, and artifacts. Walking through the museum feels less like visiting a collection and more like stepping back into a piece of American history.

That same commitment is evident in their family business, West Contracting. Founded in 1956 by Larry’s parents, Norman and Mary West, the company has grown from a small family business into one of Missouri’s leading paving contractors. For nearly 70 years, the West family has helped build the roads that connect our communities, while earning a reputation for hard work, integrity, and putting relationships first.

This year, West Contracting reached another exciting milestone as the company celebrated its 70th anniversary. As part of the celebration, Larry sat down with his son, Chris, to reflect on the company’s history, the lessons learned over the decades, and what it means to prepare the next generation to carry the business forward. Their conversation wasn’t just about construction—it was about family, leadership, and leaving things better than you found them.

 View Part 1 here. 
 View Part 2 here.

At Hill Investment Group, our motto is Take the Long View. While we often think about that in terms of investing, it’s just as meaningful when we see clients who have spent decades building businesses, preserving history, and investing in future generations.

Larry and Kathleen have done all three.

We’re grateful they welcomed us into a place that’s so personal to them, and we’re even more grateful to know them as clients and friends.

When Congress creates a new savings account, there’s usually a lot of excitement, a lot of headlines, and eventually a lot of confusion. Trump Accounts are no different.

Our view is pretty simple: If your family qualifies for the free $1,000, take it.
After that, pause before directing additional savings there. In many cases, we still believe there are better tools available.

A Trump Account is a new tax-advantaged investment account for children under age 18. The investments are intentionally simple: low cost, broadly diversified U.S. stock index funds.

Children born between January 1, 2025, and December 31, 2028, who meet the eligibility requirements, may receive a one-time $1,000 contribution from the federal government. Family members can also make annual contributions, subject to contribution limits.

If you have:
• A child born between January 1, 2025 and December 31, 2028 (like me)
• A grandchild in that age range
• A niece or nephew whose parents may not have heard about the program

It’s worth making sure someone claims the government’s contribution.

This is where we think it’s helpful to separate the headline from the planning.
The headline is the free $1,000. The planning question is whether this should become your primary savings vehicle. For most families, our answer is no. If your goal is education, a 529 plan is often the better choice. If your goal is flexible gifting, a custodial or trust investment account may provide greater flexibility. If your goal is retirement, maximizing your own retirement accounts is frequently the highest impact decision you can make. Trump Accounts are another tool, not a replacement for the others.

One feature we do like is that these accounts eventually transition into something that functions much like a Traditional IRA.

That creates the possibility of converting the account to a Roth IRA during early adulthood, when many young adults have relatively little taxable income. Decades of tax-free growth after a low tax Roth conversion could make that initial $1,000 much more valuable over a lifetime. It is too early to know exactly how often this strategy will make sense, but it is an opportunity we will be watching closely.

At Hill, we don’t chase headlines.
We look for opportunities to make small, intelligent decisions that compound over decades.
For eligible families, claiming a free $1,000 is one of those decisions.

If you have a child or grandchild who may be eligible, here’s how to get started.

Step 1: Confirm eligibility.

Children born between January 1, 2025, and December 31, 2028, who are U.S. citizens with a valid Social Security number, may qualify for the government’s $1,000 contribution.

Step 2: Complete the enrollment process.

Parents or legal guardians will need to complete the required enrollment through the IRS and Treasury’s Trump Account program. If your child is eligible, this establishes their ability to receive the government’s contribution.

Step 3: Activate the account.
Once eligibility has been verified, you’ll activate the account through an approved provider. The Treasury will then deposit the $1,000 for eligible children, and family members can begin making additional contributions if they choose.
As with many new government programs, the rollout is still evolving. We expect additional financial institutions to begin offering Trump Accounts over time, making the process even more straightforward.

Helpful Resources
• IRS Trump Accounts page for eligibility requirements, FAQs, and enrollment information.
• TrumpAccounts.gov for program updates, participating providers, and account activation instructions.
• Recommended reading from the New York Times on this topic (free NYT gift link, available for a limited time)

If you have questions about whether a Trump Account fits into your family’s broader financial plan, we’re here for you.