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

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.

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.

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.

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

• Hear the origin story: Matt & Rick on the “Island of Idealism”
• Read about it in Odds On: The Making of an Evidence-Based Investor
• ️Explore the Stockdale Paradox in this podcast episode

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.

At Hill Investment Group, we think long-term—whether we’re helping clients stay the course or cultivating the next generation of talent. One of the ways we live out that mindset is through our summer internship program, which continues to grow in depth and impact each year.

Every spring, we carefully select interns who reflect our values: curiosity, humility, hard work, and a hunger to learn. We look for students who aren’t just academically strong but also thoughtful communicators and team players; people we’d want to work alongside long after the summer ends.

We often share Odds On early in the process to give candidates insight into our philosophy, then host a series of team interviews to ensure mutual fit. We see the internship as a two-way opportunity: a meaningful growth experience for the intern and a chance for us to deepen our bench of future leaders. Once they join us, interns receive a fully immersive experience, learning from every department, working on real projects, and even participating in strategic conversations. And of course, we make time for fun.

Many of our intern alumni have gone on to successful careers in finance, consulting, and even full-time roles with Hill. Their contributions continue to shape who we are. We’re proud to carry that tradition forward this year with three exceptional individuals.

Michael Wanda – Principia College

Hi, my name is Michael Wanda, and I’m a rising senior at Principia College, majoring in Business and Economics. I was born and raised in the suburbs of Nairobi, Kenya. Though I had been accepted to the top law school in the country, I followed a different calling—finance—thanks to the influence of my older brother.

When the pandemic changed everything, a chance connection through soccer helped me apply to Principia and begin a new path in the U.S. Earlier this year, I discovered Odds On and was fascinated by Matt and Rick’s journey to build Hill Investment Group. After finishing the book, I knew where I wanted to intern.

Since joining, I’ve had incredible experiences—including a memorable lunch with Matt at his usual lunch spot, Rearn Thai. The people here are kind, smart, and committed to something that feels bigger than just numbers. I’m grateful to be part of it.

Cameron Martin – University of Miami

Hello, my name is Cameron Martin. I grew up in University City, Missouri, where sports like football and wrestling taught me how to embrace adversity and push through challenges. That mindset has carried over to my academic life—I’m a Singer Scholar at the University of Miami, double majoring in Finance and Business Law.

What excites me about Hill is the mission to make the complex simple for the sake of helping others. To me, a smart person doesn’t complicate things—they clarify them. That’s what I want to do in my career, and it’s why this internship is such a great fit.

So far, the people here have been incredibly generous with their time and insight, especially Jonesy and Jack. I’m looking forward to learning more and contributing wherever I can this summer.

Sofia Perez – Washington University in St. Louis

Hi, my name is Sofia Perez. Though I was born in St. Louis, I lived in Mexico for 10 years before returning for college. I’m a rising junior at Washington University in St. Louis, double majoring in Finance and Marketing with a minor in Human-Computer Interaction.

Helping my parents run their small businesses taught me how much heart and effort go into every dollar earned. That experience sparked my interest in business and a desire to help people grow stability and opportunity.

I was drawn to Hill because of the firm’s long-term, evidence-based approach and its focus on relationships. From my first interaction, I felt aligned with the team’s values and supported in my growth. I already know I’ll look back on this experience as a defining step in my career.

We’re proud of Sofia, Cameron, and Michael, and excited to learn from them just as much as they’re learning from us. Their early contributions are already helping us grow stronger as a firm.

Stay tuned for more from the interns in a future newsletter.