To Be a Whale, You Must Invest Like One: Stephen Weiss

In the classic novel Moby-Dick, Captain Ahab's singular focus is to seek revenge against the whale that maimed him. While Ahab's quest leads to a disastrous outcome, his plight and pursuit are, nonetheless, filled with useful lessons.

In a similar but far more positive fashion, author and financier Stephen Weiss has published his second book, The Big Win, where the singular focus is the investing habits of so-called whales—or the super-rich. The last time he set pen to paper, in The Billion Dollar Mistake, Weiss probed the biggest blunders made by some of the best-known investors in the world and explored how we could learn from them.

This time around Weiss investigates the other side of the whale trade, as he profiles the traits and techniques that have come to define the careers of 10 super-successful investors.

"That's the most important thing," says Weiss, in the attached video. "You need a discipline and a strategy."

He describes all 10 of his subjects as coming from "pretty humble roots," which only makes their achievements that much more inspirational.

Lee Ainslie, of Maverick Capital, is among those profiled. Ainslie's tremendously in-depth analysis, Weiss says, revealed very early that a huge opportunity existed in what we would all later come to know as outsourcing.

Weiss also commits at least two chapters to investors he considers to be pioneers: Chuck Royce, in the area of small cap value investing, and Marty Whitman, as a pioneer of stress investing. Weiss explains, "What Chuck did that was kind of unique was to focus on value, when people typically think of small caps as growth stocks."

And even though Jim Chanos and Jim Rogers have found themselves on opposite sides of the China debate, Weiss believes that over time they can both be right.

Jim Rogers believes so strongly in the Chinese century, Weiss points out, that he moved his family to Singapore in 2007. Jim Chanos, on the other hand, is what Weiss calls "doggedly cynical," an anti-Rogers if you will, who is currently known for being one of the most outspoken skeptics of the Chinese real estate bubble. But prior to that, Weiss observes, Chanos "was the one that uncovered the Enron scandal and Worldcom."

In short, where Herman Melville's whale tale ends tragically, each of Weiss' chapters ends in "takeaways" that are designed to ease your journey on the road to riches.

Advertisement