Wednesday, January 7, 2026

The Investing Lessons History Never Forgets

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The Investing Lessons History Never Forgets

Kristin Orman, Research Director, The Oxford Club

Kristin Orman

I've said it before...

Some of the best lessons about money, risk, and long-term thinking don't come from spreadsheets.

They come from experiences. They come from history. They come from seeing how people adapt when conditions change.

Legendary investor, Jim Rogers, believes the same.

In the 1970s, Rogers co-founded the Quantum Fund and made "more money than I knew existed in the world."

So, at the ripe old age of 37 years old, Rogers retired.

Then, in 1980, he set off on a 22-month adventure. He traveled through 52 countries and more than 100,000 miles on a motorcycle and set a Guinness world record.

His successful investment philosophy blended travel with investment insights in order to better understand the markets. He's said that his extensive travel has given him a firsthand understanding of various economies and markets.

During that trip, and future adventures, Rogers studied the elements that push successful nations and economies up and other traits that caused nations and economies to collapse.

Sicily is one of the best places in the world to study that idea.

For more than 3,000 years, this island has lived through booms, crashes, foreign takeovers, natural disasters, and reinventions.

Empires have risen and fallen here. Yet, through it all, Sicily survived and, more-often-than-not, thrived.

Sicily sits in the middle of the Mediterranean. Because of that, it became a natural hub for trade, shipping, and culture. Greeks, Romans, Arabs, Normans, and Spanish rulers all wanted it - not because it was trendy, but because of its strategic location.

That's a powerful market lesson.

The best investments often reside at natural intersections: trade routes, supply chains, energy flows, or technological shifts. These forces last longer than any single trend.

Sometimes, it's not what you know; it's where you sit.

But it wasn't always a smooth ride.

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Sicily has faced earthquakes, invasions, famine, and political collapse. Yet, cities were rebuilt, trade resumed, and the people adapted. They endured.

Investors today face their own shocks: inflation spikes, market crashes, policy shifts, and technological disruption. None of this is new. What matters is not avoiding volatility but building systems that can navigate it.

The goal isn't to eliminate risk. It's to understand it, price it, and position around it. Smart investors don't avoid volatility; they plan for it.

True wealth isn't built to predict change. It's built to withstand and endure it.

Risk and risk-taking are not the enemies... ignorance is.

Here's another lesson from Sicily...

The people never relied on one thing.

They produced grain, wine, olives, citrus, and seafood. They traded with Africa, Europe, and the Middle East. That way, when one route slowed, another opened.

That's the very definition of diversification. And it makes it easier to understand why diversification is so important for the long-term success of your portfolio.

Time is almost always on your side.

Many of Sicily's greatest achievements were not built overnight. Churches took generations to finish. Cities grew and evolved over centuries, and the vineyards improved with age.

Today, it's easy to forget the importance of time to successful investing.

Modern markets push speed, faster trades, faster news, and faster reactions.

That's not always a good thing.

That's because wealth still compounds the same way it always has - slowly, quietly, and unevenly. Time rewards patience and punishes impulsiveness.

More often than not, it pays to slow down and let time to the heavy lifting.

If you're interested in slowing down and learning more about Sicily, the Oxford Club is hosting a once-in-lifetime trip this fall.

Wealth, Wine, and Wander: The Essence of Sicily will begin on September 28 and includes seven nights in deluxe five-star hotels, welcome cocktails and reception at a local hot spot in Palermo, an exclusive financial seminar hosted by Chief Income Strategist Marc Lichtenfeld, numerous expert guided tours, and more.

There's also an optional post tour program October 6-9: The Best of Malta.

Our European trips always sell out fast. If you would like to experience Sicily in the unique setting of a luxurious Oxford Club adventure, I encourage you to contact our travel partner, Maggie Stephens at AESU World Travel 800.638.7640 Ext. 125 or email maggie@aesu.com as soon as possible to secure your spot.

When you travel with intention, you're forced to observe. You notice incentives. You see how people respond to constraints. You understand tradeoffs.

Those are the same skills great investors use.

This Sicily journey brings together people who value curiosity, discipline, and long-term thinking. Conversations over meals often drift toward markets, cycles, and strategy - but grounded in lived experience, not headlines.

Good investing,

Kristin

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