Home/Business/Big Mistakes
Loading...
Big Mistakes cover

Big Mistakes

The Best Investors and Their Worst Investments

3.7 (1,128 ratings)
29 minutes read | Text | 9 key ideas
In the high-stakes arena of investment, even titans stumble. "Big Mistakes: The Best Investors and Their Worst Investments" unveils the fascinating tapestry of errors from the financial world's luminaries, including Warren Buffet and Bill Ackman. With each misstep, these legends illuminate the path to resilience, turning costly blunders into invaluable wisdom. This book isn't just a litany of failures—it's a strategic manual for navigating the turbulent markets with foresight and savvy. As you delve into these riveting tales, you'll uncover the hidden art of learning from others' misadventures, arming yourself with insights that textbooks simply can't offer. Here lies a treasure trove of strategies that transform pitfalls into stepping stones, crafted for every investor eager to refine their craft and soar.

Categories

Business, Nonfiction, Self Help, Finance, Economics, Audiobook, Money, Personal Finance

Content Type

Book

Binding

ebook

Year

2018

Publisher

Bloomberg Press

Language

English

ISBN13

9781119366430

File Download

PDF | EPUB

Big Mistakes Plot Summary

Introduction

Throughout history, the most celebrated investors have achieved remarkable success not by avoiding mistakes, but by learning from them. These financial titans—whose decisions have moved markets and whose strategies have created vast fortunes—have one surprising trait in common: they've all failed spectacularly at some point. Their greatness stems not from perfect decision-making, but from their resilience and ability to extract wisdom from their most painful losses. The investing legends profiled in these pages reveal that intelligence alone never guarantees success in the markets. Whether it was Benjamin Graham watching his strategies falter during the Great Depression, Warren Buffett overpaying for Dexter Shoes, or John Paulson struggling to replicate his famous housing market short, each icon has stumbled on their path to greatness. Through their stories, we gain invaluable insights about human psychology, risk management, and the dangers of overconfidence—lessons that can help ordinary investors navigate their own financial journeys with greater wisdom and perspective.

Chapter 1: The Formative Years: Early Background and Education

Benjamin Graham, known as the "Dean of Wall Street," was born in London in 1894 and moved to New York as a child. His father died when he was young, and his family struggled financially—an experience that would later influence his cautious, value-oriented approach to investing. Despite these challenges, Graham's brilliant mind earned him a scholarship to Columbia University, where he graduated as salutatorian in 1914. His academic excellence attracted job offers from multiple departments, including English, mathematics, and philosophy—a testament to his remarkable intellect. Jesse Livermore, born in 1877, followed a dramatically different path. Raised on a farm in Massachusetts, he left home at just 14 to seek his fortune in Boston. Without formal education in finance, he found work as a "board boy" at a brokerage firm, posting stock and commodity prices on a blackboard. His phenomenal mathematical ability and memory allowed him to spot patterns in price movements. Soon he was trading at "bucket shops," gambling establishments that took bets on stock prices without actually executing trades. By age 15, he had earned his first $1,000—equivalent to several years' wages for average workers at the time. Warren Buffett showed financial aptitude from a remarkably early age. Growing up in Omaha, Nebraska, he was an entrepreneurial child who sold chewing gum, Coca-Cola bottles, and magazines door-to-door. At age 11, he purchased his first stock—three shares of Cities Service Preferred. Though the investment initially lost value, causing him anxiety, he held on until he could sell at a small profit—an early lesson in patience that would serve him well. His childhood bedroom was filled with books about business and investing, reflecting an intellectual curiosity about money that set him apart from his peers. Charlie Munger, Buffett's future partner, demonstrated extraordinary intellect in his youth but followed a more conventional educational path. Born in Omaha in 1924, he excelled academically and eventually attended the University of Michigan to study mathematics. His education was interrupted by World War II, during which he served as a meteorologist in the Army Air Corps. After the war, he was accepted to Harvard Law School despite not having an undergraduate degree—a rare exception that highlighted his exceptional abilities. This formal legal training would later complement Buffett's financial genius at Berkshire Hathaway. Each of these investing legends showed early signs of the qualities that would later distinguish them: Graham's intellectual brilliance, Livermore's intuitive understanding of market psychology, Buffett's fascination with business fundamentals, and Munger's analytical mind. Yet their paths to success were far from straight lines. Each would face significant challenges that would test their resolve and reshape their investment philosophies, proving that even natural talent requires tempering through experience and, often, failure.

Chapter 2: Breaking Into Wall Street: First Successes and Failures

Benjamin Graham's entry into Wall Street in 1914 coincided with the outbreak of World War I. Starting at the bottom as a clerk delivering securities and checks, his extraordinary intelligence quickly propelled him upward. Within just six weeks, he was writing the firm's daily market letter. By 1920, he had established his own investment partnership, the Graham Corporation, applying arbitrage techniques—simultaneously purchasing undervalued securities while selling overvalued ones. His early success was impressive, and by 1926, his Benjamin Graham Joint Account was earning substantial returns, outperforming the broader market significantly. Jesse Livermore's early career illustrated both the promise and peril of pure speculation. After mastering the bucket shops of Boston, where he consistently won by reading tape and understanding market psychology, he moved to New York to trade on the actual stock exchange at age 23. His initial foray into professional trading was disastrous—he quickly lost his entire $2,500 stake on short positions that moved against him. This humbling experience taught him that the real market behaved differently than bucket shops: "The tape always spoke ancient history to me, as far as my system of trading went, and I didn't realize it." This painful lesson forced him to recalibrate his approach before returning to the market. Warren Buffett's professional journey began after studying under Benjamin Graham at Columbia Business School in the early 1950s. Eager to work for his mentor, he offered to work for Graham for free, but was initially turned down. Undeterred, Buffett returned to Omaha and began building his own investment portfolio while working as a stockbroker. When Graham finally hired him in 1954, Buffett absorbed his value investing principles but also began developing his own variations. By 1956, at just 26 years old, he had saved enough to start Buffett Partnership Ltd. with $105,100—$100 from himself and the rest from family and friends. His first big success came when he identified an undervalued company called Sanborn Maps, delivering a 50% return for his investors. John Paulson's Wall Street career began more conventionally but would lead to one of the greatest trades in history. After earning his MBA from Harvard Business School, he worked at Boston Consulting Group before moving to Bear Stearns and then Odyssey Partners. In 1994, he founded Paulson & Co. with just $2 million of his own money. Initially focusing on merger arbitrage—a relatively conservative strategy that involved betting on the outcome of announced corporate mergers—he built a solid if unspectacular record. Few would have predicted that this cautious arbitrageur would later make billions by betting against the housing market. These early careers reveal a crucial pattern: even the greatest investors rarely find immediate, sustained success. Each faced periods of difficulty that forced them to refine their approaches. Graham's early success was interrupted by the crash of 1929, which nearly wiped him out. Livermore repeatedly built and lost fortunes as he struggled to maintain discipline. Buffett had to develop beyond Graham's strict value formulas to find his own approach that incorporated high-quality businesses. Paulson spent years in relative obscurity before his famous housing short. Their resilience during these formative professional years—the ability to learn from setbacks rather than being defined by them—would prove essential to their eventual legendary status.

Chapter 3: The Investment Philosophy: Core Principles and Methods

Benjamin Graham's investment philosophy centered on the concept of "margin of safety"—purchasing securities significantly below their intrinsic value to create a buffer against error or misfortune. Unlike speculators who tried to anticipate market movements, Graham focused on objective analysis of financial statements, seeking companies trading below their liquidation value. "Investment is most intelligent when it is most businesslike," he wrote, emphasizing that stocks represent ownership in actual businesses, not just ticker symbols. This disciplined, analytical approach became the foundation of value investing. Graham was notably humble about market forecasting, writing that "the future of security prices is never predictable." Warren Buffett began as a strict Graham disciple but evolved significantly over time. Under the influence of Charlie Munger and the businessman Philip Fisher, Buffett gradually shifted from buying "cigar butts"—deeply undervalued but mediocre businesses with one "puff" left—to acquiring "wonderful companies at fair prices." He developed a preference for businesses with "economic moats"—sustainable competitive advantages that protected them from competition. Buffett focused intensely on management quality, capital allocation, and long-term earnings power rather than quarterly results. His famous rule—"Be fearful when others are greedy, and greedy when others are fearful"—encapsulated his contrarian instinct and emotional discipline. John Maynard Keynes, better known as an economist, was also a sophisticated investor who managed Cambridge University's endowment fund. His investment philosophy underwent a profound transformation during his career. Early on, he attempted to time market cycles based on macroeconomic analysis, but after suffering losses in the 1929 crash, he abandoned this approach. "I began to believe that the only way to make money was to examine companies, one by one, and to buy into them when they were cheap," he wrote. This conversion to a fundamentals-based, concentrated portfolio approach predated Graham's published works and yielded excellent returns for Cambridge over many years. Jack Bogle developed a radically different investment philosophy based on his study of mutual fund performance. After analyzing decades of data, he concluded that most active managers failed to outperform the market after accounting for fees. This insight led him to create the first index fund accessible to retail investors in 1976. "Don't look for the needle in the haystack; just buy the haystack," became his mantra, arguing that owning the entire market at minimal cost was the most reliable path to investment success. Bogle's philosophy emphasized cost minimization, diversification, and long-term holding—principles that seemed revolutionary at the time but have since been validated by decades of performance data. Stanley Druckenmiller, representing the global macro tradition, developed a philosophy focused on identifying major economic trends and aggressively capitalizing on them. Unlike Bogle's passive approach, Druckenmiller sought concentrated bets with asymmetric risk-reward profiles. "It's not whether you're right or wrong that's important, but how much money you make when you're right and how much you lose when you're wrong," he explained. His approach relied heavily on flexibility—being willing to quickly reverse positions when evidence changed—and on understanding the psychology driving markets. While appearing speculative compared to Graham or Bogle, Druckenmiller's philosophy actually incorporated strict risk management principles that allowed him to make bold bets without risking catastrophic losses. These diverse investment philosophies highlight that there is no single "correct" approach to the markets. Each legend developed methods aligned with their psychological makeup, analytical strengths, and views about market efficiency. What unites them is intellectual honesty—a willingness to test their ideas against reality and adapt when necessary—and emotional discipline that allowed them to maintain their principles during market extremes when others abandoned theirs.

Chapter 4: Major Investment Mistakes: Analysis and Context

Warren Buffett's acquisition of Dexter Shoe Company in 1993 stands as perhaps his most publicly acknowledged investment mistake. Buffett paid $433 million in Berkshire Hathaway stock for the Maine-based shoe manufacturer, describing it as having "a long, profitable history, enduring franchise and superb management." What he failed to anticipate was how global competition would devastate American shoe manufacturing. By 2001, Dexter had essentially become worthless, and Buffett was forced to write off the entire investment. Making matters worse, the Berkshire shares he used as currency had appreciated enormously, meaning the true cost of this mistake exceeded $6 billion. Buffett later candidly admitted: "As a financial disaster, this one deserves a spot in the Guinness Book of World Records." Long-Term Capital Management's collapse in 1998 demonstrated how even Nobel Prize-winning brilliance could lead to catastrophe. Founded by John Meriwether and staffed with star traders and academics including Myron Scholes and Robert Merton, LTCM initially generated extraordinary returns using complex mathematical models to identify market inefficiencies. Their sophisticated risk management systems, however, failed to account for the possibility of extreme, correlated market movements. When Russia defaulted on its debt in August 1998, markets behaved in ways their models deemed virtually impossible. Within weeks, LTCM lost over $4.6 billion, threatening the entire financial system and requiring a Federal Reserve-orchestrated bailout. Their fundamental error was confusing model sophistication with accuracy, ignoring the limitations of quantitative approaches in markets driven by human behavior. Jesse Livermore's career was marked by multiple cycles of spectacular success followed by devastating losses. Perhaps his most instructive mistake occurred in 1908 when he allowed friendship to override his trading discipline. Teaming up with cotton operator Teddy Price, Livermore abandoned his own analysis and accumulated an enormous speculative position in cotton. When the market turned against him, he doubled down rather than cutting losses—violating his own trading rules. "It seems incredible that knowing the game as well as I did, and with an experience of twelve or fourteen years of speculating in stocks and commodities, I did precisely the wrong thing," he later wrote. This mistake cost him millions and highlighted how even seasoned traders can be undone by emotional influences and social pressure. Stanley Druckenmiller's foray into technology stocks during the dot-com bubble represents a classic case of FOMO (fear of missing out) affecting even sophisticated investors. Despite building his reputation on macroeconomic analysis, Druckenmiller found himself seduced by the spectacular gains tech stocks were generating in 1999-2000. After initially shorting these overvalued companies, he reversed course and began heavily buying the same stocks he had previously dismissed as absurd. When the bubble burst in March 2000, Quantum Fund suffered losses exceeding $3 billion. He later admitted: "I bought $6 billion worth of tech stocks, and in six weeks I had lost $3 billion in that one play. You asked me what I learned. I didn't learn anything. I already knew that I wasn't supposed to do that." Bill Ackman's crusade against Herbalife demonstrates how conviction can transform into costly obsession. In December 2012, Ackman publicly announced a $1 billion short position against Herbalife, calling it a pyramid scheme destined for collapse. This public declaration attracted opposing bets from rival hedge fund managers Carl Icahn and Dan Loeb, who drove the stock higher. Rather than reassessing when evidence contradicted his thesis, Ackman intensified his campaign, producing voluminous research and even funding a documentary. After years of losses and reputational damage, Ackman finally exited most of his position in 2018. His mistake wasn't necessarily his initial analysis, but his unwillingness to accept that markets can remain "irrational" longer than even well-capitalized investors can remain solvent. These investment mistakes reveal recurring patterns: overconfidence in one's analysis, allowing emotions to override established disciplines, failing to adapt when evidence contradicts one's thesis, and underestimating the complexity of markets driven by both fundamentals and psychology. Even investing legends fall prey to these pitfalls, highlighting that successful investing requires not just intelligence but emotional regulation, intellectual flexibility, and the humility to recognize when you're wrong.

Chapter 5: Learning from Failure: The Turning Points

Benjamin Graham's investment approach underwent a profound transformation after the 1929 crash devastated his portfolio. Having lost over 70% of his capital, Graham emerged from this crucible with a deeper appreciation for risk management and psychological discipline. This painful experience led him to develop his margin of safety concept, which became central to his investment philosophy. "The investor's chief problem—and even his worst enemy—is likely to be himself," Graham later wrote, acknowledging that emotional reactions often lead to poor decisions. His post-crash research established the quantitative foundation for value investing, demonstrating that stocks trading below their net current asset value substantially outperformed the market. This methodology, born from his greatest failure, would guide generations of investors. John Maynard Keynes abandoned market timing after disastrous losses in the early 1930s. Previously, he had attempted to anticipate economic cycles and position Cambridge University's endowment accordingly. After watching this approach fail, Keynes embraced a fundamentals-based, concentrated portfolio strategy. "As time goes on, I get more and more convinced that the right method in investment is to put fairly large sums into enterprises which one thinks one knows something about," he wrote in 1934. This pivot proved remarkably successful—Cambridge's portfolio outperformed the broader market by approximately 8% annually from 1932 to 1946, even through the challenges of World War II. Keynes's willingness to completely reconstruct his investment approach after failure exemplifies intellectual flexibility at its finest. Jack Bogle's path to creating the index fund began with his own professional setback. As president of Wellington Management Company in the 1960s, Bogle approved a merger with a more aggressive investment firm to keep pace with the go-go market of that era. When markets crashed in the early 1970s, Wellington's funds performed disastrously, and Bogle was fired as president. This humbling experience forced him to reconsider conventional industry wisdom. Studying mutual fund performance data, he recognized that most active managers failed to beat the market after fees. This insight led to his creation of the first index fund in 1976—initially derided as "Bogle's Folly" but ultimately revolutionizing the investment landscape. Bogle transformed his greatest professional failure into an innovation that would benefit millions of investors. George Soros developed his theory of reflexivity—which emphasizes the two-way feedback between market prices and fundamentals—after painful trading losses early in his career. Traditional economic theory suggested markets tend toward equilibrium, but Soros's experiences showed him that investor perceptions could drive prices far from fundamental values in self-reinforcing cycles. After being repeatedly caught on the wrong side of such moves, Soros incorporated this insight into his trading approach. Rather than fighting market momentum, he learned to identify and ride these self-reinforcing trends, often accelerating his commitment as positions moved in his favor. This ability to adapt his theoretical framework based on real-world trading experiences became a cornerstone of his spectacular success managing the Quantum Fund. Peter Lynch, who generated 29% annual returns during his tenure managing Fidelity's Magellan Fund, credits early investment failures with shaping his successful approach. As a young analyst, Lynch made numerous mistakes—becoming enamored with story stocks, relying too heavily on macroeconomic forecasts, and failing to adequately research companies. These experiences taught him to focus intensely on business fundamentals rather than market noise. "In this business, if you're good, you're right six times out of ten," Lynch later observed, emphasizing that accepting and learning from inevitable mistakes was essential. His eventual "invest in what you know" philosophy emerged directly from recognizing how his best ideas came from personal observations rather than complex financial theories. These turning points reveal common patterns in how legendary investors respond to failure. Rather than becoming discouraged or defensive, they engaged in honest self-assessment and fundamental reconsideration of their approaches. They extracted precise lessons from their mistakes and systematically incorporated these insights into revised investment methodologies. Most importantly, they demonstrated psychological resilience—the ability to maintain confidence in their revised approaches despite previous disappointments. This capacity to transform failure into growth separates the merely talented from those who achieve lasting greatness in the investment world.

Chapter 6: Legacy and Impact: Lasting Influence on Investing

Benjamin Graham's influence on modern investing can hardly be overstated. His books, "Security Analysis" and "The Intelligent Investor," established the analytical foundation of value investing that has guided generations of investors. Warren Buffett, his most famous student, called "The Intelligent Investor" "by far the best book about investing ever written." Graham's emphasis on fundamental analysis, margin of safety, and viewing stocks as ownership interests in businesses rather than trading vehicles revolutionized investment practice. His Columbia Business School courses trained numerous successful investors including Walter Schloss and Irving Kahn. Perhaps most significantly, Graham transformed investing from speculation based on hunches and tips into a disciplined, intellectually rigorous profession with established principles and methodologies. Jack Bogle's creation of the index fund democratized investing for millions of ordinary people. Before Bogle, small investors faced high fees, opaque practices, and poor performance from actively managed mutual funds. The Vanguard 500 Index Fund, launched in 1976, offered a low-cost alternative that simply tracked the market rather than attempting to beat it. Initially ridiculed, index funds now hold trillions of dollars globally and have forced the entire investment industry to reduce fees and increase transparency. Bogle's insistence that investment companies should be organized to benefit shareholders rather than managers led to Vanguard's unique mutual ownership structure. His client-first philosophy created a new ethical standard against which all investment firms are now measured. Warren Buffett and Charlie Munger transformed Graham's strict value criteria into a more flexible approach focused on high-quality businesses with sustainable competitive advantages. This evolution made value investing applicable to modern economic conditions dominated by intellectual property and brand value rather than tangible assets. Through their annual Berkshire Hathaway shareholder letters and meetings, they have educated millions about rational investing principles, corporate governance, and business ethics. Buffett's emphasis on long-term thinking—being "fearful when others are greedy and greedy when others are fearful"—provides a crucial counterbalance to market short-termism. His pledge to donate over 99% of his wealth has also established a new standard for billionaire philanthropy. John Paulson's successful bet against subprime mortgages in 2007-2008 permanently altered how markets think about systemic risk and financial complexity. His fund's ability to identify the housing bubble and find effective instruments to profit from its collapse—generating $15 billion in profits—demonstrated that determined analysis could uncover major market mispricing even in seemingly efficient markets. This trade inspired a generation of investors to look more skeptically at conventional wisdom and complex financial instruments. It also highlighted how derivative instruments could be used not just for speculation but for expressing fundamental views about economic vulnerabilities that were difficult to capture through traditional investments. John Bogle's articulation of the efficient market hypothesis provided the intellectual foundation for passive investing. While markets are not perfectly efficient, Fama demonstrated that they are efficient enough to make consistent outperformance extremely difficult, especially after accounting for costs. His research showing that most active managers underperform their benchmarks fundamentally challenged the investment industry's value proposition. The resulting shift toward index-based strategies has redirected trillions of dollars of investment capital and forced active managers to more clearly articulate their sources of potential advantage. Fama's work also established more rigorous standards for evaluating investment performance, emphasizing risk-adjusted returns rather than raw results. These legacies continue to shape investment practice today, often in ways their originators could not have anticipated. Graham's fundamental analysis techniques are now applied to cryptocurrencies and digital assets that didn't exist during his lifetime. Bogle's emphasis on cost minimization has expanded beyond index funds to transform how active strategies are delivered. Buffett and Munger's focus on competitive advantages influences how venture capitalists evaluate technology startups. Collectively, these investors haven't just generated exceptional returns; they've created intellectual frameworks that continue to evolve and guide capital allocation decisions throughout the global economy.

Chapter 7: Personal Reflections: Beyond the Trading Floor

Warren Buffett's life beyond investing reveals a man of surprising simplicity and consistent values. Despite amassing one of the world's largest fortunes, he continues to live in the same modest Omaha house he purchased in 1958 for $31,500. His daily routine has remained largely unchanged for decades: reading extensively (he estimates spending 80% of his working day reading), drinking several Cherry Cokes, and playing bridge with friends. Buffett has maintained lifelong friendships and prioritized personal relationships, saying "Basically, when you get to my age, you'll measure your success in life by how many of the people you want to have love you actually do love you." His decision to pledge 99% of his wealth to philanthropy, primarily through the Gates Foundation, demonstrates that accumulating money was never his ultimate goal but rather a scorecard for his investing acumen. Charlie Munger's intellectual curiosity extends far beyond financial markets. An avid reader across disciplines including psychology, biology, physics, and history, Munger developed what he calls a "latticework of mental models" drawn from multiple fields. This multidisciplinary approach informed not just his investing but his entire worldview. Unlike many successful people who become more rigid with age, Munger continued learning and revising his opinions well into his nineties. His life demonstrates remarkable consistency—married to his first wife for 54 years until her death, living in the same house for decades, and maintaining the same circle of friends. Munger's wit and wisdom, delivered through memorable aphorisms like "Show me the incentives and I'll show you the outcome," have made him a beloved figure beyond investment circles. John Maynard Keynes balanced his investment activities with extraordinary achievements in multiple domains. While managing Cambridge University's endowment and his own portfolio, he simultaneously revolutionized economic theory, advised the British Treasury during both World Wars, and helped design the post-WWII international monetary system. Somehow he also found time to collect art (assembling an important collection of Impressionist and Post-Impressionist paintings), write extensively on topics beyond economics, and serve as director of the British Eugenics Society. A member of the Bloomsbury Group, he maintained close friendships with literary and artistic figures including Virginia Woolf and E.M. Forster. Keynes' ability to excel across such diverse fields demonstrates how intellectual breadth can enhance rather than dilute specialized expertise. Benjamin Graham's life outside investing revealed a Renaissance man with wide-ranging talents and interests. He taught at Columbia Business School for 28 years, influencing generations of students beyond just Warren Buffett. A gifted mathematician, Graham also wrote a play that was produced on Broadway, translated works from Spanish, German, and Latin, and was working on a book about Shakespeare when he died. His personal life was complicated—married three times with numerous affairs—suggesting that the emotional discipline he advocated in investing didn't always extend to his relationships. Graham's journey from childhood poverty after his father's death to financial security and intellectual prominence embodied the American dream and perhaps fueled his interest in finding undervalued opportunities, both in markets and in life. Jesse Livermore's tumultuous personal life contrasted sharply with his analytical approach to markets. Despite amassing several fortunes, he declared bankruptcy multiple times and ultimately took his own life in 1940, leaving a note that read "My life has been a failure." His three marriages were marked by conflict, including a bizarre incident where his second wife shot his son (who survived). Livermore lived extravagantly during his successful periods—owning a 300-foot yacht, a private railway car, and lavish homes—but struggled with depression when trading went against him. His tragic story illustrates how even extraordinary talent in one domain doesn't guarantee happiness or balance, and how the psychological pressures of trading can exact a devastating toll when success becomes tied to personal identity. These personal dimensions reveal that great investors are far more complex than their market performance suggests. Many balanced intense focus on their craft with rich lives beyond finance—cultivating relationships, pursuing intellectual interests, and contributing to society. Others struggled to find such balance, allowing market volatility to create emotional turbulence in their personal lives. What unites them is that each found investment approaches aligned with their unique personalities and values. Their stories remind us that successful investing isn't about adopting someone else's system, but developing principles that work with your own psychology, circumstances, and goals—a deeply personal journey that extends far beyond the trading floor.

Summary

The greatest investors in history share one fundamental trait: they all made significant mistakes, but transformed those failures into wisdom that informed their future decisions. From Benjamin Graham's near-wipeout in the 1929 crash that led to his margin of safety principle, to Warren Buffett's $6 billion Dexter Shoes blunder, to Stanley Druckenmiller's ill-fated tech stock plunge during the dot-com bubble—these legends demonstrate that investing excellence comes not from avoiding errors but from responding to them with intellectual honesty and emotional resilience. Their stories reveal that success in the markets requires more than intelligence; it demands psychological discipline, adaptability, and the humility to recognize when you're wrong. For the ordinary investor, perhaps the most valuable takeaway is that you don't need to be perfect to succeed. Rather than chasing impossible perfection, focus on developing an approach aligned with your own psychological makeup and long-term goals. Establish rules that limit your ability to make emotionally-driven decisions during market extremes. Create a realistic plan that you can actually stick with through market cycles. Remember that even Warren Buffett once said, "The most important quality for an investor is temperament, not intellect." The investing legends profiled here succeeded not because they avoided mistakes, but because they learned to recognize, analyze, and adapt to them—turning their biggest blunders into the foundation of lasting wisdom that anyone can apply.

Best Quote

“When the game is no longer being played your way, it is only human to say the new approach is all wrong, bound to lead to trouble, etc. I have been scornful of such behavior by others in the past. I have also seen the penalties incurred by those who evaluate conditions as they were – not as they are. Essentially I am out of step with present conditions. On one point, however, I am clear. I will not abandon a previous approach whose logic I understand even though it may mean foregoing large, and apparently easy, profits to embrace an approach which I don't fully understand, have not practiced successfully and which, possibly, could lead to a substantial permanent loss of capital.6” ― Michael Batnick, Big Mistakes: The Best Investors and Their Worst Investments

Review Summary

Strengths: The book's engaging storytelling and insightful analysis stand out, drawing readers into the investment world through captivating narratives. Its accessible writing style effectively humanizes legendary investors, making their vulnerabilities relatable. Anecdotes about figures like Warren Buffett and Benjamin Graham are particularly appreciated for their entertainment value and educational insights.\nWeaknesses: A relatively short length leaves some readers wanting more depth or additional case studies. Occasionally, the book assumes a baseline understanding of financial concepts, which might challenge those without prior investment knowledge.\nOverall Sentiment: Reception is generally positive, with readers valuing the book's practical wisdom and its ability to demystify investing. It is seen as both a cautionary tale and an inspirational guide for investors.\nKey Takeaway: Mistakes are an inevitable part of the investment journey, and learning from them is crucial. The book illustrates that even the most successful investors have faced and grown from their errors, offering valuable lessons for all levels of investors.

About Author

Loading...
Michael Batnick Avatar

Michael Batnick

As Director of Research at Ritholtz Wealth Management, Michael Batnick, CFA reads research publications and stays on top the latest trends in the industry. Michael is a member of the investment committee and heads up the company’s internal research efforts. He spends most of his time developing and implementing risk management and portfolio strategies for the firm’s clients.Michael is the author of Big Mistakes: The Best Investors and Their Worst Investments . He is also co-host of the Animal Spirits podcast.

Read more

Download PDF & EPUB

To save this Black List summary for later, download the free PDF and EPUB. You can print it out, or read offline at your convenience.

Book Cover

Big Mistakes

By Michael Batnick

0:00/0:00

Build Your Library

Select titles that spark your interest. We'll find bite-sized summaries you'll love.