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 idealistic. 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

The wait is almost over!

Our newly remodeled Nashville office is nearly ready and we couldn’t be more excited to share it with you.

We designed the space to reflect what matters most to us: clarity, transparency, and simplicity. It’s also welcoming, professional, and soon to be full of Nashville charm. We can’t wait for you to experience the refreshed space. It’s built to inspire collaboration and connection.

Hill Team members Nick Ashby and Sherrie Dickson are especially excited to settle back in. With more natural light, open layouts, and beautiful views of the hills, it’s a space that truly embodies our commitment to Taking the Long View, something we know you value, too.

We look forward to welcoming you soon!

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.