Earlier this week, I had dinner with one of my Diligence Club members, Alfred. He flew down to Singapore for business.
And I was stoked to finally have met him in person. You see, we saw each other through my Diligence Monthly Webinars.
I enjoyed our dinner chat. We both love to cycle. And we spoke many things from investing and life. But one part of our chat really stuck with me – and we both agreed: Successful leaders (and investors) are successful because they notice things that others don’t.
They will say: “I notice this…”.
They spot something small… Something others miss.
And it becomes their edge.
He turned $50k to $900 million investing
Over the last 14 years investing, I read what made investors accumulate life-changing wealth. And I couldn’t help but recall a man who turned a mere $50,000 into $900 million.
His name is Shelby Davis.
He started investing later than most high-profile investors – in his late 30s with just $50,000. From The Davis Dynasty: “David left his state job for the stock market in 1947. Kathryn recalls her family’s reaction to Davis’s sudden exit from secure government work: ‘They thought it was a little crazy.’”
Yet, when he died at 85 years old, he amassed over $900 million ($1.8 billion in today’s terms by the time he died.
“Over the next four and a half decades, Davis skillfully chauffeured his portfolio into one of the great Wall Street fortunes. Basically, he stuck with insurance stocks through booms, busts, bebop, beatniks, and the Beatles. When U.S. insurers got too pricey, he bought Japanese insurance stocks. In the 1960s, his Japanese holdings took off like pigeons near a firecracker. By the time he died, in 1994, he’d multiplied his original stake 18,000 times.”
It was a fascinating story.
He had an intuition no one else had
Now back in the 1940s, Wall Street didn’t care about insurance stocks. Most investors then thought insurers were boring.
Davis saw something no one else did:
Shelby Davis focused on one thing alone – he poured himself into the entire industry to dig up unpolished gems. He saw something different. He acted on it.
The thing is, you can never make money simply by following the “crowded trade” – whether it’s cryptocurrencies, high growth stocks, large cap tech stocks and so on.
If you want to accumulate money that could change your lifestyle, achieve your financial goals, you’ve to think different.
It doesn’t make sense to make money from where everyone is pouring their money in.
Think about this:
- Banks during the global financial crisis
- High growth stocks in 2021
- China property boom in the mid 2010s
From my experience, true wealth is never created from crowded trade.
For me, it’s always looking at big, contrarian ideas that’s unloved.
That’s how you build passive income
That’s how you grow your portfolio for the long term
And that’s how you reach your true financial goals.
Here’s the thing. All of us already have that intuition whispering in us – that calm, inner voice.
You don’t need to be a genius to act. You just need the courage to act.
Sometimes, investing can be simple.
Willie Keng, CFA
Founder, Dividend Titan


