Mistake-driven learning and the investment process

If done correctly, investing is an iterative process. One that is experienced. Obviously, if one puts everything he owns into a high-flying cloud technology stock and blows himself out, that process is stunted. Part of being an investor is playing defensively enough to continue building on past wins.

I recently had the chance to sit down with Stephen Weiss, author of Billion Dollar Mistake: Learning the Art of Investing Through the Missteps of Legendary Investors and a very experienced executive on Wall Street.  Here’s what he shared about learning from mistakes:

What do you learn more from looking at mistakes than maybe looking at successful trades?

Weiss: Well, what I found through my career and observing others is that the best investors I ever got to know, the one’s I covered through my career, and I think I have covered a hall of fame of investment professionals, was that they spent more time dissecting their mistakes so they wouldn’t repeat them, than dissecting the victories, the winning investments. They seem to resonate more, and they are much more aggravating. When you make money on stock, or on an investment theme, you pat yourself on the back and say, “OK, let’s move on.”

You do have your discipline, and you follow that discipline, but when you make a mistake it really resonates because it has cost you money. And whether it’s blow to your ego, or a blow to your wallet, generally it’s both, you want to make sure you don’t do it again. It’s, “How can I be so stupid? How did I do that?” If you can keep that mental list, or in some cases, like I do a written checklist, and say, “You know what? I’m not going to do that again, I found it’s made me money by not costing me money.”

I think that’s so interesting, so insightful. As I was reading through the book, and I was thinking about the approach, a lot of times, successful trades, it’s unclear whether they are based on skill or on luck, you know? But at least with a losing trade, you now have an opportunity to say, “Hey, what went wrong? How could I have been more skillful in that trade?”

Weiss: Yeah. Absolutely right, and mistakes, if you can take the mistakes out of your process, you do well. It’s no different than we just saw in the Super Bowl. So, guess what? The team that won made fewer mistakes. Steelers turned it over, interceptions, fumbles. Green Bay was mistake free, essentially, so they came out on top. I don’t think it’s any different in investing.

Read the whole transcript/listen to the interview.

Learning from hedge funds’ billion dollar mistakes (podcast)

In this week’s episode of Tradestreaming Radio, we interview Stephen Weiss, author of the newish book, Billion Dollar Mistake: Learning the Art of Investing Through the Missteps of Legendary Investors. You can also find a full transcript of the show here.

Weiss had a long-spanning career on Wall Street (Oppenheimer, Salomon, Lehman) where he covered many of the top hedge funds and even spent part of his career helping run Stevie Cohen’s SAC Capital.  He took some great insights and made them even more interesting: by focusing on the mistakes top investors have made.

We discuss:

  • Why mistakes are better learning experiences for investors than winners
  • Why passion is not an investment strategy and why Kirk Kerkorian loved American cars too much
  • How Omega Advisor’s Leon Cooperman plays and manages risk in emerging markets
  • Why Bill Ackman made loot on Barnes and Noble ($BKS) but lost a ton on Borders ($BGP)
  • How these takeaways are applicable to individual investors

I really enjoyed this discussion with Weiss not only because it was an interesting view into the investing patterns of the world’s best investors but he’s distilled his experiences into a real discipline.

One really compelling insight I think we can all take away from The Billion Dollar Mistake is that it’s hard to discern whether successful trades were skillful or just lucky.  Trading losses provide an opportunity for investors to reckon their processes.

More Resources

Learn more about the book and Stephen Weiss