Coming back from maternity leave after welcoming our daughter this spring has reminded me of what our work at Hill is really about: helping clients use their money as a tool to build lives rich in meaning, not just numbers.

Whether you’re navigating new parenthood, approaching retirement, or somewhere in between, the core questions often remain the same: What matters most? And how can your money support that?

Here are a few reflections that have stayed with me through this milestone.

Time Is Our Most Limited Asset

This season has made it clear: time is precious. As the saying goes, the days are long, but the weeks are short. At Hill, we encourage clients to think of time like any other resource, i.e., something to be used intentionally.

Having a baby sharpened my awareness of how valuable time with all generations can be. We’ve prioritized visits and calls with our parents and grandparents, including Merrill. One visual we often share is Tim Urban’s “Your Life in Weeks,” which maps the average lifespan as a grid of boxes, each one a week. Sam Harris captures the feeling well: “It always is later than you think.”

Experiences That Leave a Lasting Impact

One book that’s prompted meaningful reflection is Die With Zero, which invites readers to think intentionally about how they use time, money, and attention. One key idea is the “memory dividend,” that experiences created now continue to bring joy over time.

During our first family trip with Merrill, we bought matching tracksuits for three generations (thankfully not pictured on the cover of this post!). The laughter that moment created has become part of our family story, which is something we’ll carry forward.

When you “eventize” small moments, making them playful, meaningful, or tradition-worthy, you create experiences that stay with you long after the money is spent.

Freedom Through Planning

Taking the Long View isn’t about deferring joy. It’s about aligning today’s choices with your long-term values. For our family, that included investing in a high-quality caregiver–not only to support our daughter’s development, but to give both Walter and me the capacity to continue doing meaningful work. This single decision had ripple effects across our financial plan and peace of mind.

In our experience, thoughtful planning doesn’t restrict you. Instead it creates more space for the things that matter.

The Time to Act Is Now

Watching our daughter grow has been a reminder that certain windows of opportunity are fleeting. Whether it’s a trip you’ve been considering, a gift you’ve meant to give, or simply time with someone you care about, the moment to act may be now.

At Hill, we aim to help you simplify, clarify, and align your financial life so it supports the life you want to live. With a new rhythm, a deeper commitment to this work, and a fresh perspective, I’m more convinced than ever: the best investments are the ones that help us be present, generous, and fully alive.

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

At Hill, we strive to make our backstage values visible on the front stage. In other words, how we work is just as important as what we achieve. We aim to live our values daily so clearly that even our newest team members can recognize them in action, and our clients can see them, too.

As our 2025 summer interns wrap up their time with us, we asked each of them to reflect on their experience and share how they observed Hill’s culture at work.

Last month’s summer party was a great example of how Hill blends business with fun. Remote team members flew in, and I finally got to meet people I’d only seen on Zoom. Connecting in a relaxed, in-person setting made the team feel even more welcoming and real.

The event also marked Hill’s 20-year anniversary—an experience I feel lucky to have shared. Hearing stories from long-time team members gave me perspective on the firm’s journey and the values that built it. What stood out most was how intentionally Hill celebrates people and milestones. It’s clear that fun and community are a meaningful part of how the team stays connected and motivated.

My time at Hill deepened my understanding of evidence-based investing in ways I didn’t expect. From the beginning, I was given meaningful work and encouraged to understand the “why” behind it. I was introduced early on to the Fama-French Five-Factor Model, which helped me connect ideas like profitability and market cap to Hill’s investment philosophy.

That first project sparked curiosity, and I kept exploring. Team members offered resources, asked great questions, and created space for learning. Their support made it clear that growth is a shared value here.

A standout moment for me was building a model for trades. It was more complex than I anticipated, and I went through several rounds of refinement. It would have been easy to rush, but I reminded myself that precision matters more than speed.

With help from the team, I asked questions, improved steadily, and ultimately built something I was proud of—not just for the outcome, but for how I got there. I saw firsthand how patience and discipline are part of Hill’s daily rhythm.