When Two Serial Expats Meet: My Conversation with a Legend

As someone who's lived in China, Singapore, and now calls Dubai home, I've always believed that international experience gives entrepreneurs a unique edge. But when I sat down with Jim Rogers—the legendary investor and co-founder of Quantum Fund—I discovered just how transformative this mindset can be for building wealth.

Coming from a small farm town in Connecticut where I was the first in my family to even get a passport, Rogers' story resonated deeply with me. Here was someone from an even smaller town in Alabama (his phone number was literally just "5") who turned his curiosity about the world into one of the most successful investment careers in history.

Who is Jim Rogers? A Background for Fellow Entrepreneurs

Before our conversation, I knew Jim Rogers by reputation, but speaking with him revealed the depth of his achievements:

  • Co-founder of Quantum Fund: Partnered with George Soros to create one of history's most successful hedge funds

  • Investment Performance: Achieved over 4,000% returns during his tenure at Quantum Fund

  • The Original Digital Nomad: Traveled around the world twice on motorcycle, covering 150,000+ miles across six continents

  • Bestselling Author: Wrote "Investment Biker," "Hot Commodities," and "Adventure Capitalist"

  • Commodities Pioneer: Invested in commodities when Wall Street completely ignored this asset class

  • Fellow Expat: Lives in Singapore, having previously resided in numerous countries

What struck me most was how his investment philosophy grew directly from his travel experiences—something I've been discovering in my own entrepreneurial journey.

The Travel-Investment Connection: What I Learned

"Living Abroad Forces You to Think for Yourself"

During our interview, Rogers shared something that hit close to home: "If you're in a foreign land, you have to learn new things and you have to think for yourself a lot. Probably a lot more than if you never leave home."

As someone who moved to China in 2000 (when people told me "they don't have food there" and "something bad will happen to you"), I understand exactly what he means. Living abroad strips away your assumptions and forces you to see opportunities others miss.

My Biggest Takeaway: Look Where Others Aren't Looking

Rogers' most powerful insight—one that's completely changed how I approach business opportunities—is this: always look where other people aren't looking.

He told me that when he started on Wall Street:

  • There was no publicly traded oil market (imagine that!)

  • Almost nobody read the commodities page in the Wall Street Journal

  • European currencies were completely ignored by American investors

This blindness created massive opportunities for those willing to explore. As a fellow expat entrepreneur, I see this playing out today in regions like the Middle East and Africa—places I'm personally focusing on for this exact reason.

What This Means for Today's Entrepreneurs

The "Don't Invest What You Don't Know" Rule

One thing Rogers emphasized that every entrepreneur needs to hear: "Please don't invest in things you don't know about. And if you can't learn it, don't invest."

This applies whether you're looking at:

  • New asset classes like cryptocurrency and tokenization

  • International market expansion

  • Commodity investments

  • Emerging technology sectors

As someone navigating these waters myself, I appreciate his practical approach: either learn it thoroughly, or find something else.

Ground-Level Research vs. Flying High

When I asked about his motorcycle travels, Rogers explained: "I was interested in seeing the world from the ground up. If you see the world close to the ground, you learn a lot more about the world and about yourself."

This philosophy has shaped my approach to business development. Instead of making decisions from boardrooms, I'm out there experiencing markets firsthand—whether it's understanding fintech in Dubai or seeing manufacturing changes in China.

My Personal Revelations from Our Conversation

Embracing Calculated Risk

Rogers shared a story about being held hostage in the Congo for eight days. His takeaway? "No matter how bad things were, I learned something."

This resonated with me because, looking back at my own "risky" moves—like being the first in my family to get a passport, moving to China when everyone said I'd starve, relocating to Dubai during uncertain times—each experience taught me something invaluable about business and myself.

The Adventure-Profit Connection

What fascinated me most was Rogers' admission: "My goal in life was to have adventure." The profit followed naturally from this mindset.

As entrepreneurs, we're often told to chase money first. But Rogers proved that following your curiosity and sense of adventure can be the most profitable strategy of all. This has become a core principle in how I approach new business ventures.

Current Opportunities: What We Both See

Regions Worth Watching

During our conversation, Rogers highlighted transformations I'm witnessing firsthand:

Middle East: I'm living through Saudi Arabia's dramatic modernization. Projects like NEOM represent massive opportunities for entrepreneurs who understand the region.

UAE: Dubai's continued evolution (Rogers noted how much it's changed just in the past three years I've been here) creates daily business opportunities.

Africa: Both Rogers and I see vast untapped potential across the continent.

My Takeaway on New Asset Classes

While Rogers advocates caution with new technologies like crypto and tokenization, he acknowledges the opportunities exist. His advice mirrors my approach: understand it thoroughly before investing, but don't ignore it entirely.

Practical Lessons for Fellow Entrepreneurs

Breaking Out of Your Comfort Zone (Like We Both Did)

Rogers grew up where his phone number was "5." I grew up in small-town Connecticut. Both of us had that crucial realization: there's so much more out there.

For today's entrepreneurs, this means:

  • Actively seeking international business opportunities

  • Building networks across different cultures

  • Learning from diverse business models

  • Not being afraid to relocate for opportunities

The Power of Contrarian Thinking

Rogers built wealth by investing where others wouldn't. As entrepreneurs, we can apply this by:

  • Exploring underserved markets (like I'm doing in the Middle East and Africa)

  • Developing solutions for ignored demographics

  • Entering "boring" industries others overlook

  • Building businesses in emerging economies

What I'm Implementing from This Conversation

For My Investment Strategy:

  1. Studying overlooked markets: Currently researching sectors receiving little mainstream attention

  2. Traveling with purpose: Each business trip now includes potential investment research

  3. Reading beyond mainstream: Following local news sources in regions I'm exploring

  4. Building global networks: Connecting with entrepreneurs and investors worldwide

For My Business Development:

  1. Identifying underserved markets: Looking for opportunities in overlooked demographics

  2. Leveraging international experience: Using my China/Singapore/Dubai experience as competitive advantage

  3. Studying successful international models: Adapting proven concepts to new markets

  4. Embracing location independence: Building businesses that benefit from global perspective

A Personal Note on Risk and Adventure

One moment that really struck me was when Rogers said, "If you want to go, send me an email. We'll go off and get killed together. Although I don't want to get killed."

This perfectly captures the entrepreneurial spirit—acknowledging risk while pursuing adventure anyway. It's exactly how I felt moving to each new country, starting each new venture.

Listen to Our Full Conversation

I could only scratch the surface of our fascinating discussion here. To hear Rogers' complete insights on travel, investing, and entrepreneurship:

You'll discover:

  • Rogers' most memorable (and dangerous) travel experiences

  • Specific investment opportunities he's identified through travel

  • His encouraging words for women entrepreneurs seeking adventure

  • Stories from his motorcycle journeys that shaped history

  • Current market insights from someone who's seen it all

My Key Takeaways as a Fellow Entrepreneur

After this conversation, I'm more convinced than ever that international experience isn't just nice to have—it's essential for modern entrepreneurs. Rogers proved that:

  1. Global perspective creates unbeatable competitive advantage

  2. Direct experience always trumps theoretical knowledge

  3. The biggest opportunities hide in overlooked places

  4. Cultural understanding directly impacts business success

  5. Adventure and profit are natural partners

As someone building businesses across multiple continents, I can attest to every one of these principles.

Whether you're planning your first international expansion or considering a major pivot, Rogers' philosophy of combining curiosity, courage, and careful research provides a proven roadmap for success.

The world is full of opportunities for those brave enough to look beyond their hometown borders. Take it from two people who've made that leap—the view from out here is worth it.

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