Featured entries from our Journal

Details Are Part of Our Difference

David Booth on How to Choose an Advisor

20 Years. 20 Lessons. Still Taking the Long View.

Making the Short List: Citywire Highlights Our Research-Driven Approach

The Tax Law Changed. Our Approach Hasn’t.

Category: A piece we love

Investing for Upgrades: How the Long View Creates Better Experiences

The beauty and benefit of taking the long view is not just about building wealth. It’s about upgrading your experiences.


Transcript:

Hey everyone, Matt Hall here. You’re going to see more of me like this, not just in writing, but on video. We think it’s a warmer way to stay connected. You can see us, you can hear us, and not just read about us.

So last month I shared some reflections on Hill Investment Group’s 20 year journey. And if you missed it, you can catch it somewhere in the post or the link below. And I left something out that I really want to share with you. It’s likely one of the most important observations over the last 20 years of Hill. And then 25 years of doing evidence-based planning and investing.

When I was coming up in this business, as I wrote in Odds On, I was so struck by how powerful the research was and is patient diversified investing.

It works. The data is and was overwhelming. But here’s the thing, people don’t connect to research alone. Those of us in the industry, we love the logic, the data, and the evidence, but most clients aren’t asking for more charts. You want to know, how does this connect to my life? What will this do for me?

And there, that’s where the difference comes in. We spend our time measuring and managing, running the evidence, monitoring the portfolios, staying disciplined and helping you stay disciplined. And what that does for you, for clients is it frees you up to live.

And here is what I’ve noticed. The payoff rarely shows up in mansions or flash. It shows up in upgrades.

The upgraded hotel room where the view changes the trip, the better seat on the plane that makes travel easier. The bike trip where someone else is helping you with just the right amount of support or the family vacation where you, you don’t just go, you upgrade it by bringing kids and grandkids along. Those moments aren’t about showing off wealth. They’re about upgrading experiences, creating memories, and being more present with the people you love.

One client summed it up perfectly when he told me. Now, Matt, the only thing I think about is which pool toys to get out for the grandkids. I think that’s the beauty of taking the long view. It’s not just about building wealth, it’s about upgrading your experiences, turning patience and discipline into more time, more freedom, and more memories with the people who matter most to you.

We thank you for being with us on this journey. Here’s to the next 20 years and all the upgrades that come with them.

20th Anniversary Hill Logo

The Long View Library: Books Worth Reading & Sharing

Longview Library Book Illustration

Many of the people we work with tell us they value not just our diligence and professionalism, but also the personal touch and team chemistry that make working together feel special. In that spirit, we’re pulling back the curtain to share what’s been on our bookshelves lately and why these titles resonated with us. Think of it as an open invitation to browse, discover, and maybe even find your next great read or a thoughtful gift.

Let’s start with my suggestion:
Odds On: The Making of an Evidence-Based Investor by our own Matt Hall is a thoughtful overview of our evidence-based approach, how it reflects academic insights, and how it contrasts with more traditional investing methods.

You may have read it at some point over the past decade, but your friends and family—especially the next generation of investors who were too young when it debuted in 2016—may not have had the chance.

If you or someone you know would like to explore our investing philosophy, we’re happy to share a complimentary copy. There’s no cost or obligation. It’s simply a resource we’re proud to pass along. Just email me and we’ll send one your way. Short on time or attention? Email me for a two-page summary. Prefer audio or Kindle? Those versions are available too.

Now, onto more team favorites for you to explore:

I’ve been leaning hard into fiction lately and found some real gems. Pachinko is an epic family story set in Korea and Japan, surprising and moving in how it explores generational identity. Tom Lake is a beautifully written portrait of family and choices that shape a life. The Night Circus—magical realism, stunning imagery, and an immersive mystery—is pure escape. My latest nonfiction read was Good Morning, Monster: powerful real-life stories of resilience that stay with you.

In fiction, I recently reread A Tree Grows in Brooklyn, a timeless favorite. I also enjoyed The Magnificent Lives of Marjorie Post (a great example of someone who took the long view). The Favorites is a story about figure skaters I picked up for nostalgic reasons—think The Cutting Edge. Lady Tan’s Circle of Women scratched my historical fiction itch. On the nonfiction side, The Anxious Generation has been especially helpful as a mom looking to support calm and confidence in my kids.

Going Infinite (by Michael Lewis) offers a fascinating look at Sam Bankman-Fried and the broader crypto narrative. It’s a complex profile of someone who became a central figure in one of the biggest financial stories of the decade. For fiction, Project Hail Mary (by the author of The Martian) was a standout, and Tomorrow, and Tomorrow, and Tomorrow might be one of the best books I’ve read in a while. For a lighter beach read: Nora Goes Off Script.

Good Morning, Monster was a recommendation from Matt, and it’s now one of my top five books. It shares a therapist’s most difficult cases—dark, yes, but incredibly insightful. It helped me appreciate how much childhood experiences shape adult life.

A fiction book I recently loved is Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin. It follows two childhood friends who reconnect in college and begin designing video games together. What stood out most was the deep, complex relationship between the two main characters, intimate without being romantic. It was refreshing and emotionally rich.

My favorite nonfiction book is Endurance: Shackleton’s Incredible Voyage by Alfred Lansing. It tells the gripping true story of Ernest Shackleton’s 1914 Antarctic expedition, where his crew endured an unimaginable struggle for survival after their ship was crushed by ice. It’s an unforgettable story of leadership and perseverance.

We’d love to hear what you’re reading, too. If you have a book you’d recommend, please send it our way, along with a short note about why you loved it. With your permission, we may feature your suggestion in an upcoming issue of the Monthly Journal.

20 Years. 20 Lessons. Still Taking the Long View.

What 20 Years Have Taught Us

Twenty years ago, we launched Hill Investment Group with a simple idea and a bit of idealism. We called our firm the Island of Idealism: a place where evidence mattered more than ego, long-term thinking trumped short-term noise, and clients could breathe a little easier knowing they had a guide they could trust.

That idealism is still with us. But over two decades, it’s been sharpened by experience. We’ve helped clients weather storms, tune out the headlines, and stay committed to plans built for decades, not days.

In the spirit of reflection, I reached out to my co-founder, Rick Hill, to help compile this list. Rick is now retired, but his thinking (and our friendship) continues to shape our work and HIG culture.

Here are 20 lessons we’ve learned in 20 years. Some are personal. Some are practical. All of them are built to last.

20 Lessons in 20 Years

On Investing

1. Evidence beats emotion.
2. You don’t need to predict the future to build wealth. You need a process.
3. Costs, taxes, and behavior matter more than market forecasts.
4. Markets reward discipline, not cleverness.
5. Diversification is the only free lunch. Eat it every day.
6. A sound allocation only works if you stick with it. Education builds confidence, and confidence fuels discipline.

On Clients

7. Our most successful clients are curious and engaged. They’re fun to work with, understand the philosophy, and like to delegate.
8. Listening is more powerful than convincing.
9. Trust is earned through credibility, reliability, and intimacy, not promised through performance.
10. Simplicity makes people feel smart. Complexity makes them feel confused. We care deeply about simplicity.
11. People want progress, not perfection.

On Building a Firm

12. Culture matters and should be tended like a garden.
13. High standards are contagious. So is apathy.
14. You don’t need to be big to be mighty.
15. The right people are worth the wait.
16. Saying no creates space for what matters.

On Perspective

17. Don’t check your portfolio when the world feels upside down. Check your plan.
18. The Stockdale Paradox applies to investing: Confront the facts, believe in the outcome. Untether from the short term.
19. Market volatility is normal. History proves it. You get paid for tolerating the bumpy ride.
20. Take the long view. It’s the only one that works.

Whether you’ve been with us since the early days or just recently joined the journey, thank you for trusting us. We’re proud of what we’ve built, and we’re even more excited about what’s ahead.

Still client-focused. Still evolving. Still taking the long view.

For your further exploration

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Featured entries from our Journal

Details Are Part of Our Difference

David Booth on How to Choose an Advisor

20 Years. 20 Lessons. Still Taking the Long View.

Making the Short List: Citywire Highlights Our Research-Driven Approach

The Tax Law Changed. Our Approach Hasn’t.

Hill Investment Group