Featured entries from our Journal

Signal vs. Noise: Stock Market Concentration Concerns

The Player or the House?

We’re in the Hospitality Business

Client-Exclusive Webinar with David Booth, Co-Founder and Chairman of Dimensional

A Good Estate Plan Should Make Life Easier

Category: A piece we love

10 Years of Odds On

In 1999, a book changed the direction of my life.

At the time, I had recently dropped out of law school and was trying to figure out what was next. I was in that phase of life where you have plenty of energy and curiosity, very little skill, and a strong desire to do something meaningful that helps other people.

Around that time, I met Larry Swedroe.

Larry had written a book called The Only Guide to a Winning Investment Strategy You’ll Ever Need. I still remember sitting down with it and realizing that the first 100- pages quietly reshaped how I thought, not just about money and investing, but about what I wanted to do in my professional life. The approach felt more like a calling than a job.

Looking back, I didn’t just discover a better way to invest. I discovered a set of ideas worth dedicating a career to.

Until then, I thought investing was about forecasts, predictions, and confident opinions about the future. Larry’s work introduced me to something very different. It was grounded in data and evidence. It showed that humility, discipline, and a long-term perspective were far more powerful than trying to outguess markets and pick winners.

It felt logical, rational, and deceptively simple to me. It smelled like the truth. And I loved it.

That realization set me on a course that eventually led to the creation of Hill Investment Group.

Years later, when we started the firm, I ran into an unexpected problem. We would give clients books like Larry’s because the ideas were so important, and we wanted them to understand our approach at a deeper level. Unfortunately, many people simply wouldn’t read them. Not because the books weren’t good. They were excellent. However, they were technical and written primarily for professionals rather than investors.

This dilemma got me thinking…and searching. I wanted something that could open the door a little wider for readers. Something relatable, understandable, memorable, and useful.

So I tried an experiment.

Instead of writing a technical guide, I “buried the vegetables” inside a story.

The result was Odds On: The Making of an Evidence-Based Investor. It follows my own coming of age in the investment world, where readers encounter the mentors, lessons, and ideas that shaped the philosophy behind our firm.

A few years after the book came out, I attended a book party on Park Avenue in New York surrounded by other authors. I struck up a conversation with a writer who had created a popular series of illustrated books. After listening to the story of why I had written Odds On, he paused and said something that stuck with me.

“That makes sense,” he said. “You’re a second-ring storyteller.”

I had never heard the phrase before, so he explained.

The first ring develops the idea. The second ring takes that idea and translates it so a broader audience can understand it.

That description felt exactly right.

Larry was part of the first ring. His work changed how I saw investing. Odds On was my attempt to carry those ideas outward in a way that more people could absorb. More real investors, not just practitioners.

When the manuscript first circulated, a few agents told me the book would fail. It wasn’t prescriptive enough. I was warned that most non-fiction business books go nowhere and help no one, especially if the author does not already have a significant following.

Twelve years after writing it and ten years after publication, the story has been far more powerful and interesting than I ever imagined.

The book has traveled widely. It has been read by students, investors, and advisors across the country. It eventually made its way to the Netherlands, where it was translated into Dutch. Along the way, it sparked conversations, friendships, podcast interviews, speaking invitations, and thoughtful notes from readers around the world.

In many cases, the book became the first handshake between us.

Some readers eventually became clients. Some became collaborators and friends. Some changed the investing philosophy of their entire firm. A few even joined our team.

And in a way, the book changed my life too. Not because of copies sold or opportunities created, but because of the relationships that have grown out of it. Over the years, we’ve received more trust, gratitude, and kindness from long-time clients than I ever imagined possible. Compliance rules prevent us from sharing testimonials, but I can say this: the real riches have come from the people.

What began as an attempt to explain a philosophy ended up creating something much more meaningful: a community of people who believe in taking the long view.

Ideas move through rings. Someone discovers them. Someone translates them. Eventually, someone passes them forward.

That ripple effect is what we’re celebrating in this month’s journal.

Ten years after publication, we’re looking back at the journey of Odds On — the ideas behind it, the unexpected places it traveled, and the people it connected us with along the way.

And if the ideas resonate with you, perhaps the next ring starts with something simple: share the book with someone who might benefit from it.

Take the long view,

Matt Signature

 

 

Matt Hall

 

The Slow Things Still Win

Slow horses

The power of slowing down when everything around us says hurry.

I just finished Lonesome Dove (widely considered one of the greatest Westerns of all time). At 850 pages, it doesn’t move quickly, and that’s the point. You can’t rush it. You get pulled into the dust, the dialogue, the ache of it all.

Right after closing the book, I was on Mackinac Island. No cars, no horns. Just horse-drawn carriages, bikes, and time measured by the clop of hooves. Real horsepower! It’s one of the few places that forces a slowdown, and in that stillness, you actually start to notice things again – texture, tone, the weather moving through.

In investing, there’s no reliably fast way to get rich. We all know the parable of the tortoise and the hare, but modern life makes it so tempting to rush. The social media feed refreshes, the markets move, and it feels like we need to move too. It takes real discipline to slow down; to stick with something through the long, quiet stretches.

Fall feels like the right season to remember that. It’s a time of gratitude and reflection, of harvesting what we’ve grown, and of preparing the soil for what’s next.

Investing well isn’t about reacting to every market twitch. It’s about owning global capitalism, rebalancing patiently, and letting time compound the quiet and yet powerful work happening underneath the surface.

We’ve been at this long enough to see it firsthand. Our clients’ returns over the last 20 years, and more than 25 years if you go back to when we first started using this evidence-based approach, tell the story clearly. The discipline of staying invested, diversified, patient, and calm through every kind of market storm pays off.

In a world obsessed with speed, the slow things still win.

Take the long view.
Matt Signature

 

 

 

 

The Long View on Estate Planning

Grace Kreifels, Hill Investment Group

After I earned my Certified Financial Planning (CFP(R)) designation, my grandparents were both proud and curious. They asked me to take a look at their finances and see if there was anything they should be doing differently. My grandpa had always managed things on his own and had done well, but one glaring gap stood out: they hadn’t done any estate planning.

They didn’t know what a trust was or where to start. But they did know what mattered most: how they wanted their assets to pass, which of their children they trusted to handle things, and that they wanted to make the process as easy and stress-free as possible for their family one day.

For someone used to doing everything himself, my grandpa recognized that this was one aspect of his life that he needed to delegate. He also saw the value in doing some work now to make life easier for his kids later, a small act of love that will one day make a big difference.

That mindset captures how we typically approach estate planning with our clients at Hill. It can feel complicated and overwhelming, but when you focus on the big picture and surround yourself with the right team, it becomes a powerful way to protect your family and preserve your legacy.

No two estate plans look the same. Some are wonderfully simple, others more complex. There’s no “right” way to do it—only what’s right for you. That’s why we take time to understand each client’s values, family dynamics, and long-term vision before collaborating with their attorneys and CPAs to design a plan that fits.

Here are a few guiding questions we use when helping clients update or establish their plan:

  • Is it easy to understand? You should be able to explain the big picture in plain English.
  • Does your team collaborate on your behalf? Your attorney, CPA, and Hill advisor should be aligned so your investments, taxes, and estate all work together.
  • Are you avoiding probate? The right structure may help your family avoid a lengthy and expensive court process.
  • Are your heirs protected? Your plan should clearly state how and by whom assets will be managed.
  • Is everything included? It’s easy for accounts or property to be left out due to incorrect titling.
  • Who will carry out your plan? Executors, trustees, powers of attorney, and guardians can all play important roles. It’s important to make sure they understand and accept them.

When my grandparents’ plan was complete, my mom (named as executor) told me multiple times how relieved she felt knowing everything was organized and clear. That sense of clarity is exactly what we hope to provide for every Hill family.

Estate planning isn’t one-and-done; it’s an ongoing act of care, and it’s part of Taking the Long View®. We generally recommend our clients to review their plan every five years, or sooner if life or laws change. Families grow, goals evolve, and your plan should, too.

If you’re wondering whether your plan still fits, or if you’ve been meaning to get started, we’d love to help you or a loved one take that next step.

Email us at askanadvisor@hillinvestmentgroup.com to connect with your Hill advisor and start the conversation.


Disclosure:
The information provided herein is for educational purposes only and should not be construed as investment, tax, or legal advice. Clients should consult with qualified professionals regarding their individual circumstances. Past performance is not indicative of future results. Hill Investment Group, LLC (“HIG”) is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. For additional information about Hill Investment Group, please refer to our Form ADV, available at adviserinfo.sec.gov.
Featured entries from our Journal

Signal vs. Noise: Stock Market Concentration Concerns

The Player or the House?

We’re in the Hospitality Business

Client-Exclusive Webinar with David Booth, Co-Founder and Chairman of Dimensional

A Good Estate Plan Should Make Life Easier

Hill Investment Group