Louis: Doug, a lot of our readers have asked for you to tell some war stories. What were some of your biggest wins and losses, and what were the lessons learned?
Doug: Well, it may not all fit neatly under the rubric of “lessons learned,” but I can tell you about some of the specific experiences that have shaped my career. There have certainly been some great deals and terrible deals that I’ve been in—and just as many of both that I’ve failed to get in.
L: It’s all part of what Victor Niederhoffer would call The Education of a Speculator.
D: Vic’s an old friend of mine, and his book by that title has some important insights. Although he’s mainly a short-term trader. I prefer to only buy things I can hold on to for a few months, if not a couple of years. It gives you enough time to be right. And doesn’t clutter your mind up with random noise and fluctuations.
L: Indeed; let the trend be your friend. Okay then, where do we start?
D: We’ve already told the story about my Ferrari business, in our conversation on cars, but that was my first business deal, so I do recommend reading it to those who haven’t yet.
L: So, when you got out of the hospital, did you dive right into another deal?
D: Actually, I decided to start really educating myself at that point. Among other things, I read Harry Browne’s seminal book, How You Can Profit from the Coming Devaluation, and that led directly to my first big score in the ...