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

As big believers in the power of data and evidence—whether it’s in investing, medicine, or sports—we’re thrilled to share this exceptional podcast episode featuring Jeff Luhnow, a valued client of Hill Investment Group. Jeff is a former St. Louis Cardinals leader, GM of the World Champion Houston Astros, and now a European Football (or soccer, for most Americans) Champion.

In this conversation, Jeff dives into the keys to success across business and sports, illustrating how interconnected these areas truly are. Remarkably, Jeff has applied his expertise in engineering, consulting, entrepreneurship, and team building to a sport he knew little about just a few years ago, achieving incredible success on the pitch (the field).

One of our favorite moments from the podcast is when Jeff shares: “The principles that drive success—whether in baseball, soccer, or business—are rooted in understanding the numbers, building the right team, and having the patience to see the vision through.”

Jeff’s career journey exemplifies a data-driven mindset and the power of taking the long view—principles that resonate deeply with us and guide our own work. We’re proud to support leaders like Jeff who embody these values. We think you’ll find his insights as inspiring as we do.

During the summer months, we often recommend books we are reading in the offices of Hill Investment Group. This year, we decided to steer you to a podcast we enjoy; some episodes are almost as long as an audiobook. If you’re reading this, you, like us, believe in the power of a long-term perspective, continuous learning, and evidence-based decision-making. These core principles guide our investment strategies and resonate with the themes explored in the extraordinary podcast “Acquired.”

What is “Acquired”?

“Acquired” is a highly regarded podcast that dives into the stories behind some of history’s most significant companies and acquisitions. Hosts Ben Gilbert and David Rosenthal provide in-depth analyses of how these companies were built, the strategic decisions they made, and the challenges they overcame. Each episode offers valuable insights into the entrepreneurial and business world, making it a must-listen for anyone interested in understanding the dynamics of successful companies.

Themes from “Acquired” that Resonate with Hill Investment Group

• Long-Term Perspective:

Episode Highlight: In the episode covering Amazon, “Acquired” explores Jeff Bezos’ long-term vision and his relentless focus on customer experience, illustrating how patience and strategic planning can lead to enduring success.

Hill’s Approach: Similarly, we at Hill Investment Group emphasize the importance of taking the long view. We believe patient, disciplined investing, guided by enduring principles rather than short-term market trends, is key to building sustainable wealth.

• Evidence-Based Decisions:

Episode Highlight: The episode on Whole Foods’ acquisition by Amazon underscores the significance of data-driven decisions. Bezos’ use of extensive market research and analytics to guide Amazon’s strategies reflects the power of evidence-based decision-making.

Hill’s Approach: Our investment strategies are grounded in Nobel Prize-winning academic research, ensuring our clients benefit from the most reliable financial principles.

• Resilience and Adaptability:

Episode Highlight: The story of Apple’s turnaround under Steve Jobs, as discussed on “Acquired,” showcases the company’s ability to innovate and adapt in the face of adversity.

Hill’s Approach: We prepare our clients to navigate market volatility through diversified portfolios and robust financial planning, helping them stay resilient and focused on their long-term goals.

• Continuous Learning:

Episode Highlight: Each “Acquired” episode is a business history and strategy masterclass that provides listeners with knowledge and insights.

Hill’s Approach: We believe in lifelong learning and continuous improvement. Our team regularly engages with the latest industry developments to ensure we provide our clients with the best possible advice and service.

We encourage you to explore the “Acquired” podcast to gain deeper insights into the principles that drive successful businesses. Let’s continue to embrace the long view, grounded in evidence-based principles and enriched by continuous learning.

Take the long view,

The Hill Investment Group Team

Our favorite episodes include Starbucks, Hermes, Porsche, Costco, and Nike.

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Feel free to listen to “Acquired” and join us in exploring the fascinating stories behind the world’s most successful companies.