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Killing the Market: Legendary Investor Robert W Wilson

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Robert W. Wilson is the greatest investor of all time, on the only criterion that counts: percentage return on capital. What you make with what you have, what you started out with. Wilson would be the first to point out that there are investors richer than himself; but on a percentage-return basis, he is unmatched, and untouched. He received $15,000 from his mother in 1958, and he ran this stake to the fabulous sum of $230 million, by 1986. With assistance he himself sought out, he then nearly quadrupled his net worth to $800 million, by the year 2000. This return, after taxes no less, is more than 50,000 to one. More than 5,000,000 percent. Wilson did it in about forty years, without partners. How? How, possibly? This book, "Killing the Market," tries to find, or at least get close to, an answer. Robert Wilson quit the investing business in 1986, because he had "lost his touch," as he said. The most productive of men, the hardest working of men, he started to move into philanthropy. Eventually he became just about the most important philanthropist in the United States. Of the $800 million he accumulated, he had given away fully $700 million of it at the time of his death, in 2013 (by his own hand). Movingly, Robert Wilson's gifts were never to things that entertained him, or to pet projects; they were always to charities trying very hard to make the world a better place for everybody.

104 pages, Paperback

Published May 14, 2016

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Roemer McPhee

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Displaying 1 - 16 of 16 reviews
Profile Image for Dennis Littrell.
1,081 reviews57 followers
July 21, 2016
Will satisfy some curiosity about how Robert W. Wilson did it

This sketch (88 pages) of Wilson’s career focuses on the stock market trades that he made during the latter part of the twentieth century and on his work as a philanthropist. Author Roemer McPhee does not delve much into Wilson’s private life, leaving this reader with a desire to know more about what kind of man Wilson actually was. The fact that he ran a five figure inheritance into something like $800-million just by investing the in the stock market is of course extraordinary. And that he gave it all away before jumping out the window of his apartment across the street from Central Park in New York City at age 87 is also extraordinary. We can guess that he was a “limousine liberal” since he gave $40-million to the New York Public Library and was a member of the American Civil Liberties Union for something like 40 years. But in fact he was a true liberal who cared deeply about his fellow human beings and our planet as evidenced by the hundreds of millions of dollars that he gave to such stalwart charities as The Nature Conservancy, the Environmental Defense Fund, the World Monuments Fund, and the Wildlife Conservation Society. Additionally he gave $45-million to New York City’s Catholic schools.

I was particularly interested in his actual stock picks and pans. (His portfolio typically contained 20% in short positions.) It is impossible to discern how Wilson was so good at figuring out which stocks were going up and which were going down. It would seem that Wilson worked extraordinarily long and hard at what is termed fundamental analysis while keeping a close watch on the market’s herd mentality through technical analysis. What struck me about Wilson’s strategy was the leverage he used and the amount of hedging. While hedging mitigates against the possibility of catastrophe (called “gambler’s ruin” in some circles) it tends to temper overall returns. But while Wilson was protecting his downside by hedging he greatly increased his upside by borrowing large amounts from brokers and banks for his investments. According to McPhee, Wilson typically margined 80% of his investments. This is a strategy that by itself is worthless. The key is being able to buy winners and sell short losers. To do this you simply have to be a great investor, period, or gosh-darn lucky.

One of the more interesting stories in the book is Wilson’s great misadventure with Resorts International which he sold short beginning at about $16 a share. He rode the bull as it climbed and climbed and climbed before he bailed out when it hit something like $187, losing $25-million. That was in 1978. No big deal, especially when his portfolio went from $28-million at the end of the year to $81-million two years later. And then to $100-million and up, up and up to eventually the $800-million mentioned above.

Could he have just been lucky? As some people have pointed out if you have a sampling of hundreds of investors, by chance a few of the successful ones were just lucky. That is the law of averages. And that is the experience of your average hedge fund. We’ve seen hedge fund managers have a great year and no more thereafter, and we might guess they were just lucky that year. However Wilson’s success goes beyond anything having to do with luck. He was just a great investor as touted.

This book is interesting if you are a stock market investor. And if you lived and traded during the sixties, seventies, eighties and nineties, it might be especially fascinating. McPhee’s narrative gives us some gloss into how some of the prominent old line companies such as IBM, Compaq, Wendy’s, Lockheed, American Airlines and some startups built their businesses . It was an exciting time for an investor if you had the right vibe or a penetrating and informed insight into what was happening.

Ultimately though I think McPhee could have done a better job with this book. He needed to not only shine more light on Wilson the man but he could have hired a professional editor and done some serious legwork. There’s a lot of needless repetition in the text sometimes with nearly the same expression and information given a few paragraphs or a page later. On the other hand, McPhee’s prose is definitely readable.

--Dennis Littrell, author of “The World Is Not as We Think It Is”
Profile Image for Library of.
93 reviews10 followers
March 4, 2021
Enjoyed this book, my notes below. Similar book summaries can be found at www.libraryof.xyz

The book is about the American investor Robert W. Wilson who during the 1960s to 1980s competed with Buffett and Soros for the place as the world’s best investor. In 1969, he started the hedge fund Wilson & Associates, where he almost exclusively managed his own money. He started with $15k which he inherited from his mother and had $800m at the end of his life. During his career, he had an annual return of 28%. Before he took his own life in 2013, he donated much his entire fortune to charity.

LONG-TERM TRADER. Unlike Buffett and Soros, Wilson said he was not an “original thinker”. He lived with the phone in his ear with brokers who fed him ideas. He was not an industrial magnate but a player. He saw himself more as a long-term trader than as an investor. Wilson was not interested in shares with a limited downside because then he considered that the upside was usually also limited.

”I would be bored to death simply by living in either the Bahamas or Omaha. So the most important is to enjoy life.”

WILSON’S METH LAB. Wilson knew that the risk was very high in every single position he held. In addition, the portfolio was heavily geared. This meant that there was no room for major accidents – which is why he had to diversify greatly. He likened his process to someone running a meth lab (which is very risky – if something goes wrong, everything can blow up). But if you instead ran 200 separated labs, it did not matter much if some blew up – the others ticked on and gave a good return.

RISK IS THE LACK OF A HEDGE. According to Wilson, risk was an unhedged portfolio. How leveraged the portfolio was had nothing to do with risk. Wilson worked for 30 years with a leverage of around 400% and was always aggressively geared. Overall, he did not create much wealth going short, but the shorts allowed him to earn all the more on the long positions. The short positions gave him liquidity in market crashes. With his aggressive investment style, he also knew that he would not be able to manage other people’s money emotionally – it was enough to master his own feelings.

”There is a great old saying about debt: it requires you to get up in the morning, and go to work.”

A GAME OF PERCEPTION. Wilson believed that the big money was earned by being good at being positioned before the perception of a company changed – both long and short. That’s what he attributes to his excess return. He was classified as a growth investor and tried to get into companies before they became “growth darlings” on Wall Street. In the same way, he shortened “growth darlings” which he considered used aggressive accounting or which for some reason faced tougher times.

“I was always net long no matter how bearish I was since I never wanted to get up in the morning hoping things would be worse.”

AIM HIGH. Wilson set the goal early on to become a billionaire – a high goal if you start with $15k and do not manage other people’s money. He knew it would be difficult, but by setting such a high goal he would be successful even if he did not reach all the way. He has also said that to duplicate his career requires someone who loves money above all else. He has said that the best feeling in the world is to make money – nothing beats it. In the end, he never became a billionaire, his fortune peaking at around $800m.

“My goal is to make a billion dollars. I may not get there; the important thing is to try”

THE THIRD STRIKE. Wilson retired after underperforming the market for three years in a row. He was then in his 60s and no longer as hungry. He believed that if he could no longer beat the index, it was better to become a passive investor and spend his time on other things. After that, he was depressed for a few years knowing that the most exciting time of his life was over. He then applied the “three strikes and you’re out” principle to his life when, as an 87-year-old, he threw himself out of his home on the 16th floor of his building on Manhattan. He had during his last year had two strokes and knew that he did not have much time left. Wilson had no family and left $100m behind.
223 reviews11 followers
March 6, 2023
What a bizarre little book that left me with a horrible impression on Robert Wilson. I think this encapsulates Wilson: "Wilson was not impressed with his clients' behavior, or sense of market timing, and he determined to put no emphasis on work for clients in the future". What an abhorrent shit. Used 1:5 leverage to amass an $800M fortune and then gave it all away before jumping off his balcony at 87. The middle section with case studies is decent, but too high level to hold any truly deep insights. There are much better books out there and the only reason I finished is because it is so short.
Profile Image for Sai Krishna.
3 reviews7 followers
December 18, 2017
Very little literature is available on Robert Wilson and his investment philosophy. This book provides a peek into the investing and philanthropic life of Wilson. His investing approach is unlike any other investing legends as he aimed to become a self made billionaire from just managing his proprietary capital. Bob demolishes the common notion that leverage is bad, and if put to use effectively and with discipline, can compound returns and create wealth much quicker.
3 reviews
July 9, 2023
Good little book that can reinforce some big picture ideas.

Main ideas in bullet points
- Wild and crazy stock
- Diversification 70 stocks. “10 would scare me shitless”
- Experience (cycles)
- Hedging
- Innovation (focus)
- Surprises
- Sensitivity to the markets themes, its moods, changing moods, its dreams and its fears
- As flexible as a willow - would charge his mind in a minute
- The stock market was always his master.
- Leverage
- Popular to pariah
Profile Image for Chris.
4 reviews
February 13, 2025
This book is far too brief to be useful and lacks any depth. It feels more like a draft than a real book. One chapter was two pages long. And while he did very well investing long and short, he almost went broke twice. That highlights the difference between being self-employed and being an employee: When other funds have fallen massively; they may be wound up before they can recover. Consider this book as merely an introduction to keep searching for more information.
138 reviews1 follower
June 19, 2024
Very well written for this genre of books. Doesn't rate a 5 because the topic is not that edifying. Some needless vulgarity in direct quotes.

Wilson deserves our respect for quietly donating the greater portion of his wealth to charity and environmental causes--unlike his peers who insist on getting their name chiseled into New York buildings.
Profile Image for Norm Goldman.
198 reviews8 followers
May 18, 2016
If you could liken a superstar Wall Street investor to Beethoven or Mozart, Robert W. Wilson would be right up there as the ideal comparison. His Wall Street career spanned five decades beginning in 1958 when his mother gave him an inheritance of $15, 000 in cash. By the year 2000 his net worth was approximately $800 million when he turned to philanthropy giving most of his wealth away including more than $500 million to various institutions. Apparently, he had made more money faster in the stock market than anybody else thus earning him the reputation as an extraordinary stock market guru enabling him to stockpile earnings in a way that confounded many.

Who exactly was this investor-turned- philanthropist? Was he a lucky gambler with an enormous risk tolerance or an astute savvy investor who always expected to win relying on patience, persistence, minimizing mistakes, and understanding the difference between time and timing?

Roemer McPhee, who was educated in history at Princeton University and in finance at the Wharton Graduate School of Business strongly believes that there are few things more powerful than a good example and in the world of investing you certainly can make better investment decisions by studying the financial philosophies of the best in the business. In his most recent tome, Killing the Market: Legendary Investor Robert W. Wilson works from the outside in to better understand the modus operandi of Wilson through citing various investments taken from Wilson's portfolio.

Although Wilson left very few autobiographical traces behind, McPhee, who mentions that he had met him on the social scene after 1989, was able to draw on several business articles concerning his investing acumen particularly that he was often followed in detail by such publications as Barron's, Forbes, The Wall Street Journal and Business Week and others as well as various writings concerned with the world of philanthropy.

Consequently, through this extensive research McPhee pieces together and examines several of the two hundred stock positions that were owned by Wilson at one time or another. These comprised such household names as Datapoint, Bowmar Instrument, Lockeed Aircraft, Baldwin-United, Compaq Computer Corp, Burroughs, Pizza Time Theater, Tandy Corporation, Denny's Restaurants, American Airlines and Federal Express.

As an illustration of Wilson's astuteness and sixth sense for self-protection as well as self-preservation, McPhee points to his long position in Compaq Computer when in 1983 he smelled an innovator which in his case meant huge capital gains. Compaq was eventually purchased by Hewlett-Packard twenty years late for $25 billion.

One of Wilson's most recognized strengths was his expertise in short-selling and earned him a fortune as the founding partner of a hedge fund firm, Wilson & Associates. He believed that in short-selling he would never be wiped out in a downturn.

Short-selling consists of selling borrowed shares of stock, betting that will will go down in value before it has to be bought as its most recent closing price. An example of this strategy where Wilson profited handsomely was in 1984 with the famous old Automat food vendor Horn & Hardart where he waited and predicted the downfall of the company. As McPhee states” “This is the kind of short sale that many professional short-sellers take. They wait for certain business doom, with a stock price still alive in the public market, because at that point every share you sell, every dollar you raise by selling stock, is going straight into your bank account.” On the other hand, one of his short-selling ventures did not turn out as planned when in 1978 he bet against Resorts International which had just built the first casino in Atlantic City with a short-sell of 220,000 common shares when the price was around $15 and by the time the stock reached $190 he cut his losses and was out about $10 million.

Wilson was always thorough in his research and throughout his career read the business press voraciously. He also networked a great deal and would exchange ideas with other investors. When Datapoint came out with a small public offering he was immediately interested and loaded up with it and never looked back. In fact, he held it during its ride that lasted a dozen years from 1969 to 1982 which gave him a return of fourteen times his money or a 1,300% gain.

At the age of eighty-seven and after suffering two strokes Wilson sadly died after leaping from his 16th floor apartment residence on Manhattan's Central Park West. Ironically, he was just as pragmatic in death as he was in life as he left a suicide note where he wrote:

“I had a rewarding life. Thank you and goodbye to all my friends. Please make sure you cancel all my plans. Tell everyone what I did. I’m not ashamed of killing myself. Sell all my stuff,” the note read, according to law-enforcement sources.”

Killing the Market is by no means an exhaustive study but it does provide readers with a good idea as to what made Wilson tick and how he became an icon of the investment world.

Follow Here http://goo.gl/EC9kXC To Read Norm's Interview With Roemer McPhee


19 reviews1 follower
April 14, 2021
Very basic outline of his life
Profile Image for Eric Isaac.
3 reviews
October 30, 2021
great book

Great book on a very talented investor and one you most likely have never heard of. A gem of a story
234 reviews
December 30, 2025
Biggest learning is his diversification and hedging sizing. Recommended by Dave O
Profile Image for John J..
106 reviews7 followers
May 18, 2016
In the foreword of his extraordinary new book on the life of “legendary investor” Robert W. Wilson, “Killing The Market,” Roemer McPhee refers to Wilson as “the Michelangelo of our times” and then proceeds in the pages that follow to paint a masterful life-long series of illustrations that show how Wilson became a “remarkable innovator” and “mythically talented stock picker.”

The story of Robert W. Wilson spans more than half a century, beginning with his emergence from the Detroit, Michigan area in 1958 with little more than $15,000 in his pocket (a gift from his mother at age 31). Author Roemer McPhee shows how Wilson used his many innovative methods to take that small gift and transform it to a net worth of some $800 million by the year 2000. He did this “by himself – without partners” by protecting himself from big losses, aggressive investing and keeping his eyes on the prize.

A self-driven man, Wilson is shown to have been deeply affected by his family’s “lower upper-class” socio-economic status in Detroit during the years surrounding World War II. After “failing at everything else” including banking, he decided to pursue a life as an investor in New York City. New York was the center of all that interested him, and Wilson landed a job at investment house, A.G.Becker & Co. But after he was nearly wiped out by a stock market crash in 1956, Wilson vowed never to operate in the stock market without protection. He taught himself the art of selling short and long at the same time.

The author shows how this new approach served Wilson well, as an innovator in the hedge-fund industry. This allowed Wilson to be dramatically more aggressive, taking chances on the “wild and crazy” stocks. These stocks had the most potential for movement and bigger gains. Roemer McPhee compares Wilson’s investing career in the 1950’s and 60’s to operating a methamphetamine lab of stocks, highly volatile but explosive, with the most potential of making Wilson rich as fast as possible. He quickly profited as a “portfolio genius” with heavy diversification and full hedging. Wilson had to operate as many meth labs, so to speak, at one time as possible. Yes, there would be some disasters, but there were also many, many great successes.

Wilson survived another big crash in 1962, but since he was fully leveraged and protected, he came out the other end of the tunnel unscathed. In 1962 his net worth was a whopping $300 thousand. With this money, Wilson set about investing in companies with the most possibility for innovation. These so called “new wave” businesses can be compared with many of the Internet or high tech companies of the 1990’s.

Surfing his entire career on the biggest, most dangerous waves, Wilson was able to increase his net worth again and again. Innovative, courageous and self-protective, Robert W. Wilson is portrayed again and again, as a man always in a hurry and willing to take a chance on investments.

This book is a great guide for beginning investors who also are in a hurry to make big money. Author Roemer McPhee offers a multitude of additional examples of how Robert W. Wilson reached an eventual net worth of some $800 million and, late in life, became heavily involved in philanthropies. This is a rags-to-riches story almost too hard to believe, but of great practical usefulness to any beginning investors.
Profile Image for Pamela Gossiaux.
Author 15 books17 followers
May 20, 2016
Robert W. Wilson, Investor Extraordinaire!

Killing the Market is a short, fascinating read about the life and career of investor and philanthropist Robert W. Wilson.

Given $15,000 from his mother in 1958 as a wedding present (equivalent to about $150,000 today) Wilson invested the money. That began a 40-year career in the financial market – playing the stocks – which landed him with a net worth of over $800 million before his death in 2013.

Author Roemer McPhee, a Princeton-trained in history, asks the question “How did he do it?” and tries (successfully, I think) to answer it in his book. He dives into the life and work of Wilson in what is a detailed explanation of how Wilson was able to accomplish what no one before or after him has done. How he was able to work the market to his favor, and find, with an almost primal instinct, what markets had a future.

Because I have a limited knowledge of the stock market, some of the terms in this book were a bit over my head, but what I found fascinating was the detailed way McPhee describes each big company that Wilson invested in. For me, it was fun reading the details of how these companies got started – companies I’m familiar with from my childhood.

Wilson bought stock in companies such as Datapoint, Bowmar Instrument, Lockheed Aircraft Corporation, Atari, and Jordache Jeans before others knew what was going on. He also dabbled in oil when others were selling, and in the airlines industry when it wasn’t considered “profitable.”

“He always seemed able to spot an innovator early,” writes McPhee. “Wilson had almost a sixth sense for self-protection and self-preservation in the market, as an investor.”

One of the questions the books asks (and answers), is what do you do with all that money once you have it?

While there isn’t much detail about his personal life, we do find out that Wilson was a man very concerned with the welfare of the earth and its inhabitants. He continually “tithed” as he put it, giving to charities and organization throughout his career. When he retired, however, he became a full-time philanthropist, and gave hundreds of millions of dollars away, making him one of the biggest donors in New York City and in the United States. His chief concern was to continue taking care of the earth and the people and animals that lived on our planet. Like the details that Roemer puts in the book about the companies Wilson bought stock in, he also defines the organizations he gave money to, which I found interesting because I’ve heard of most of these organizations.

The book follows Wilson through to the end of his life: Wilson staying in character until the end.

When I visit New York, now, and I see his name on various buildings or donor plaques, I’ll know the story behind the name. I think that’s cool.

I believe this book is perfect for anyone interested in investing or playing the market, whether professional or amateur. For the rest of us, it makes an interesting read into the life of a man who changed the lives of many people and many companies in the US.
78 reviews21 followers
December 1, 2020
The book describes the investing career and style of Robert Wilson.

- Went bust early on in his career (late 20s) due to significant leverage. His investment ideas went on to do well. The lesson he took away from this was that he needed to be hedged and diversified.
He held many stock (hundreds) but more stocks on the long side than on the short side.
- Always looked for stocks with potential for large moves. Many of the longs were fast growers, producers or beneficiaries of new technology. He called these "new wave" stocks. The shorts were overvalued, overhyped and/or facing significant new competition where none was anticipated at first.
- A description of his noteable investments on the long side and short side is given in one of his chapters.
- He used significant leverage by getting credit from international bankers. The level of leverage was in excess of the spirit of stock exchange limits.
He was one of the most unemotional and dispassionate men in the industry.
- His biggest investing mistakes was worrying about business competition too early. Instead see how it develops. Competition can often open new markets.
- Over the course of managing money he returned 28% per year.
- He gave up on his goal of becoming a billionaire to start giving away his money to charity and philanthropic purposes. From my reading it didn't seem the money was not all that well spent on these causes.
- He eventually took his life by jumping out of his window and falling 150 feet. The motive given in the book was that he felt it was the right time and that he lived a satisfying life, but I can't buy into that. The death was too dramatic.

The story was interesting overall, and the biggest investing takeaway for me was his biggest mistake: "anticipating competition too early".

Personally I would not be interested in living his life. As I finished reading I realised that these types of books are only written about those with the highest returns, accumulating the largest wealth, often at the expense of a life that I consider worth living. Although this is obviously based on what little knowledge we have of his personal life and worth is in the eyes of the beholder. I would be interested in reading about an investor who had great returns, great relationships and a fulfilling life (at the expense of fantastic returns and a lot of money).
Profile Image for Susan Keefe.
Author 11 books58 followers
July 9, 2016
This book is about the life and 40 year career in the financial market of Robert W. Wilson.

Robert W. Wilson was an investor and philanthropist, a man driven to succeed. He made brave investments, followed his own council, and was filled with grit, and the determination. It is these qualities which have led him to be called the greatest investor of our time.

He starting out with $15,000 from his mother in 1958 and had the ethos that ‘[to be an investor], money has to be the most important thing in the world to you.’ Through clever investing and sheer hard work, using other people’s money, his fortune grew astronomically over the years, and just before his death in 2013 he had a net worth of $800 million.

This small book is packed with interesting information about the companies Robert W. Wilson was involved in, which include many of the giants such as Lockheed Aircraft Corporation, Atari, Compaq Computer Corp, Burroughs, Pizza Time Theater, American Airlines and Federal Express.

I also touches sensitively in his personal life and passions, such as the opera, and his interest in nature, wildlife and conservation, all of which he supported fervently.

He handled his affairs with control and dignity, and this included his suicide in 2013. He left a note saying “I had a rewarding life. Thank you and goodbye to all my friends. Please make sure you cancel all my plans. Tell everyone what I did. I’m not ashamed of killing myself. Sell all my stuff,” the note read, according to law-enforcement sources.”

The author of this short book has treated the reader to an in-depth look at the life of this amazing man, and what made him tick, it is interesting, inspirational and I highly recommend it.
Profile Image for Craig Howe.
25 reviews2 followers
September 6, 2016
In my mind, Robert W. Wilson was one of the great stock market performers of my time. His Wall Street career spanned five decades. Beginning in 1958 with $15, 000 inherited from his mother, he “retired” in the year 2000 with a net worth of approximately $800 million.

It was only natural when I was offered a review copy of Roemer McPhee’s biography that I would jump at the opportunity to delve into Wilson’s investment thinking. I read every word of Killing the Market. I was left disappointed.

Understand Wilson operated a one-man shop. His hedge fund carried 200 positions – long and short – at any one time. He was a long-term investor. What was it that he saw that contributed to his success? This book offers little insight beyond “Wikipedia-like” summaries of Wilson’s home runs and dismal failures.

As an addicted reader of Alan Abelson’s "Up and Down Wall Street" in Barron’s Magazine, I suspected Wilson served as the source of many of the column’s well-reasoned, provocative and insightful ideas.

High expectations are rarely met. Wilson’s methodologies eluded me while I worked on the street. It should come as no surprise; they elude me now. I am not sure any biographer could satisfy me with the insights I seek. Wilson is dead; Abelson is dead. There is not a lot of source material.

I will say this about Roemer’s biography: it is well- written. I finished it in one sitting – three stars.
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