Dr Karrian Hepburn Malcolm, Head — Wealth Management, National Commercial Bank Jamaica LimitedStudioCraft
There are many ways to build a thriving business, but all successful entrepreneurs share a few common habits. Think about your favourite entrepreneurs, what do they all have in common? They took calculated risks, made sacrifices, embraced uncertainty, and poured everything into their dream. That’s not just true of entrepreneurship, that’s also the mindset of successful investors. Successful entrepreneurs teach us that smart investing is more than just picking stocks or chasing returns. It’s about being intentional with your resources, staying disciplined, and thinking for the long-term instead of aiming for short-term gains. So, what exactly can investors learn from successful entrepreneurs? Their journeys show us how to navigate uncertainty, build resilience into our portfolios, invest in long-term growth industries, and make financial decisions that can stand the test of time. Let’s explore three global trailblazers’ successful investment decisions, and what their actions can teach you about building lasting wealth.
Oprah Winfrey: Many people when they think about Oprah Winfrey, remember her hosting a talk show. However, Oprah did more than that. She built an empire grounded in trust, authenticity, and human connection. From her humble beginnings as a local news anchor, she rose to become one of the most influential media moguls in the world, owning the Oprah Winfrey Show. But her greatest moves happened behind the scenes — where she turned her influence into equity and long-term ownership. Through Harpo Productions, the OWN network, and strategic investments in companies like Weight Watchers and Apple, Oprah demonstrated that lasting wealth isn’t built on salary alone — it’s built on ownership. She endorsed brands and believed in them; she took calculated risks and became an investor with real skin in the game. Her US$43-million investment in Weight Watchers, which ballooned into hundreds of millions, was more than a savvy financial play — it was a lesson in conviction.
You may not have millions to invest in a company, but you can still apply Oprah’s principles to your investment portfolio. She invested in businesses she believed in, took a long-term approach, and stayed committed even during volatility. That’s exactly the mindset investors need when selecting financial instruments — whether it’s stocks, bonds, or mutual funds. Look for companies and sectors that align with your values and show strong long-term growth potential. When you believe in what you own, you’re more likely to stay invested, and that’s where real wealth is built. Ownership is powerful and when you invest portions of money into the stock market, you become part owners of these companies. You may not own a network, but you can own a piece of companies that are shaping the future. That’s how you move from earning money to building generational wealth for you and your loved ones.
Elon Musk: He may be one of the most polarising figures in business today, but if Oprah is the embodiment of thoughtful, value-aligned investing, Elon Musk represents the bold, high-conviction investor. After selling PayPal, Musk poured almost all his money-over $180 million-into SpaceX, Tesla, and SolarCity. For years, he lived on borrowed money, refusing to take the safe route. Why? Because he saw where the world was going and bet on it, unapologetically. Tesla, in particular, was ridiculed for years. Yet Musk stayed the course, believing in the electric vehicle revolution long before it was mainstream. Today, both Tesla and SpaceX are among the most valuable companies in their sectors. Of course, most investors don’t have that kind of capital, or appetite for risk, but the takeaway here isn’t about duplicating Musk’s scale-it’s about his mindset.
Musk’s investing style teaches us the value of investing for the long haul, staying disciplined, and anticipating and understanding market trends and associated risks. His entrepreneurial journey shows that successful investing is about understanding it and being prepared to face short-term losses in pursuit of long-term growth. If you believe in the big picture, don’t let market noise or temporary setbacks deter you from investing — volatility is part of the course to meaningful returns. His approach also shows that investors shouldn’t chase trends. For the average investor, this doesn’t mean trying to invent the next Tesla — but it does mean thinking ahead. When you take the time to understand market trends early and invest with intention, you position yourself ahead of the crowd. Do the research, invest early in quality assets, and stay committed. Finally, Musk concentrated his capital into a few bold ideas rather than spreading it too thin. While diversification is key to investment, over-diversifying can sometimes dilute your gains. The key is to invest intentionally. That means doing your research and working with a trusted wealth advisor to help you build a portfolio that reflects both your goals and your risk tolerance.
Jay-Z: Shawn “Jay-Z” Carter went from street-smart rapper to savvy billionaire entrepreneur by doing more than just collecting cheques — he collected equity. From launching Roc-A-Fella Records to building Roc Nation, Armand de Brignac Champagne, and investing early in Uber, Jay-Z has consistently chosen deals that let him participate in long-term wealth creation. Rather than taking endorsement fees, he often opts for ownership stakes, positioning himself to share in the upside of the businesses he believes in. His 2014 purchase of Armand de Brignac and later sale of a 50 per cent stake to LVMH was a textbook move—acquire, scale, then exit strategically while maintaining brand influence.
Jay-Z’s portfolio is also strategic. His ventures in music, fashion, liquor, and tech may seem broad, but they’re all connected by his understanding of culture and the business of entertainment. From Roc-A-Fella Records to Armand de Brignac Champagne, each investment aligned with industries he knew well and could influence. He wasn’t just spreading risk; he was building an ecosystem around his brand. Therefore, take the step to invest in industries you understand and build a portfolio that reflects your knowledge, values, and long-term vision. Strategic diversification creates synergy across the things you know best.
The common thread between the Oprah, Elon, and Jay-Z’s approach to building wealth is their ownership mindset-rooted in vision, patience, and resilience. This is the same mindset that is needed to invest successfully. Whether you’re building a business or investing your first $10,000, the same principles apply – think long-term, and like Jay-Z, invest in companies you understand, or those that align with your values, like Oprah did. Similar to Musk, do your research and stay atop of emerging industry trends and find a few high-quality businesses to invest in that can ride out market fluctuations. By approaching your investments with the same intentionality as these successful entrepreneurs, you too can turn small, consistent moves today into generational wealth tomorrow.
To talk about how you can get started and hone your owner’s mindset, email us at ncbcapinfo@jncb.com or call 876-960-7108 to speak with a wealth advisor.