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The Billion Dollar Mistake: Learning the Art of Investing Through the Missteps of Legendary Investors

Important investment lessons gleaned from the mistakes of accomplished professional investors and billionaire businessmen

The Billion Dollar Mistake is an up-close account of the career-defining mistakes that some of the world's most brilliant billionaire investors have made, and a revealing look at what we can learn from them. Drawing on author Stephen Weiss' twenty-two years experience at some of Wall Street's most prestigious firms, the core of this book is based upon original research and interviews with these legendary investors, who discuss the most significant trade or investment that went against them, the magnitude of the loss, its effect on their businesses-and on their personal lives. To some, these fascinating accounts will read like a novel; to others, it will be a treasured and unique investment guide.

This intriguing book skillfully examines the causal relationship between the quirks of each investor's personality and the mistakes they have committed. Along the way, Weiss provides a series of compelling narrative accounts of the individuals' road to success, the particular mistakes they made, the character flaws that led to them, and the lessons learned. While some investors made errors of judgment, others made errors of perception. The Billion Dollar Mistake


Uncovers important lessons learned from the failures of some of the most enduring and accomplished investors, including Kirk Kerkorian, Bill Ackman, Aubrey McClendon and Leon Cooperman Discusses how to incorporate these lessons into your investment discipline and avoid the same missteps Reveals common mistakes made by bigger investors that the average investor can relate-the only difference is in magnitude with more zeros attached to the loss Includes insights on improving your investment endeavors by refining your approach to today's markets Learning from the missteps of the best in the investment business can help you succeed. With The Billion Dollar Mistake, you'll discover how.

272 pages, Hardcover

First published October 29, 2009

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Stephen L. Weiss

5 books11 followers

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5 stars
16 (20%)
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24 (31%)
3 stars
25 (32%)
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Displaying 1 - 6 of 6 reviews
163 reviews10 followers
December 17, 2019
Reading this book for work, there were a few interesting stories that were probably a little useful, but overall I would not recommend this book. Weiss talks about 11 different incidents where an investor lost over a billion dollars. From each episode, he highlights some things that you should take away. This is a format that I generally like, and there are some good lessons, like the importance of diversification, how leverage is a sword that cuts both ways, how you need to understand the risk of your investments, and how style drift can be bad. I did not think the writing was very good. It was a little sensationalized for my taste, and didn’t go into the details of many of the investments as much as I would have preferred. In the discussion of Bernie Madoff, there is a lot of description of the sad state of the people who lost money, and less of an emphasis on what Madoff did to con people. I liked the review of a number of investors and stories I’d never heard before, but I just thought it could have been done much better. This type of book might be useful and interesting for a number of people, but I wouldn’t recommend this particular one.
Profile Image for Timothy Chklovski.
67 reviews25 followers
August 6, 2014
If you are trying to be a better investor, an immensely valuable book, although human biases can make it harder to embrace its key lessons.

As the catchy title suggests, the book examines failed investments of a handful of standout investors. The sympathetic reader who -- rather than dismiss the mistakes as other's folly -- looks to the underlying causes, and asks if perhaps they could fall prey to same issues will be rewarded with some common themes of how incredibly competent investors got a bad result.

The common themes are not hard to guess -- it's things like pattern-matching a situation that evolved to the old situation that worked out well, ego-driven decision making, as well as underestimating how irrational or mispriced the voting machine can get before the weighing machine prevails. I'll leave more -- and the subtlety of the themes listed -- as a pleasure for the reader to discover and analyse.

Each chapter also sketches out a background of a particular investor, and I enjoyed these details in their own right (for example, Pzena, Newberg and Greenblatt were all buddies and co-authors on their early net-net research in the MBA program, which is very "Superinvestors of Graham and Doddsville" since all three became successful value investors). With the stage set, it then describes an expensive and usually unforced error; then it looks at what the takeaways are.

The closing chapter on Madoff, Dreier, etc is about an even worse mistake: people with perfectly wonderful career opportunities wound up bringing jail sentences on themselves and infamy on their families. But the cautionary theme is similar -- let hubris get the better of you and there is no limit to how low you can wind up.

Summary: With perfect armchair wisdom, it was very tempting to think "well I'd never be drawn into doing something so silly". And indeed, simply not being on wall street can help with avoiding Madoff / Dreier trap of defining self by yachts or houses in the Hamptons. But, even final chapter aside, using what Michael J. Mauboussin calls "the outside view", I think one would do well to recognize these traps are harder to avoid than they seem in hindsight.

One would get the most out of this book if one approached it with "would I rather take serious this books lessons -- where smart, experienced people of making bad decisions and winding up with terrible results -- or risk losing big part of my net worth to a similar cognitive failure in the heat of the moment at some time in the future?"

Enjoy the book, and hope you learn for $10 what cost these folks an awful lot more.
83 reviews4 followers
November 4, 2014
The mix of investing mistakes across different individuals and different scenarios makes this book exceptional. The chapters are well organized beginning with the intro to the individual, their background, the mistake, and then lessons learned. I would say the majority of the mistakes are applicable to most investors but some are outlandish. Either way, I'd recommend as the lessons learned are helpful for any investor at any skill level.
6 reviews
December 22, 2010
Well researched book with limited first-hand account of business mistakes made by prominent investors. Weiss was great in providing the background information on the mistakes and his analysis on them. It would have been much better if he had gotten feedback from the people involved.
Profile Image for Greg.
313 reviews2 followers
February 17, 2011
More interesting for the larger-than-life personalities on display than the investment advice; terrifying to imagine what it would mean to lose billions. Depressing to realize the people who lose them bounce back and make another billion.
Profile Image for BeyondDL.
62 reviews
March 17, 2012
After getting past the attention (and money) grabbing title on the cover, the book is a good read in the way that it's entertaining to watch a plane overshoot a runway. Learning the art of investing from the crash landings of billion dollar economies, this book packs plenty of momentum and hurt.
Displaying 1 - 6 of 6 reviews