When acquiring a stock, there are only two possible outcomes: profit or loss. However, as Lee Freeman-Shor highlights in his The Art of Execution: How the World’s Best Investors Get It Wrong and Still Make Millions book, it is not just the outcome but how one reacts to both gains and losses that define success. A well-managed losing stock can still be turned into a profitable one through the right approach.

Freeman-Shor based The Art of Execution on his analysis of the investments of 45 top fund managers over seven years, each managing between USD 25 million and USD 150 million. He discovered that successful investors share common habits around how they handle both losing and winning positions. The author categorizes investor behavior into five patterns, or “tribes,” which are further divided into how they respond to both losing and winning scenarios:

Losing scenario behavior

Rabbit

Assassin

Hunter

Winning scenario behavior

Connoisseur

Raider

The author refrains from classifying investor types as inherently good or bad, with one notable exception to be addressed later. Instead, he emphasizes that effective investors are those who can successfully manage their portfolios in any market condition. The key lies in understanding these behavioral patterns and properly executing them in one’s investing strategy, which we’ll examine in this article.

About the Author

Lee Freeman-Shor is a seasoned portfolio manager, having worked at Old Mutual Global Investors (now part of Jupiter Asset Management), a UK-based asset management company, with over 20 years of experience in fund management and investing strategies.

Since October 2005, Freeman-Shor has been managing and allocating capital for some of the world’s top investors. With a strong background in equity research, Freeman-Shor currently manages over USD 1 billion in high-alpha and multi-asset strategies.

Over 7 years of observing asset management, Freeman-Shor compiled his knowledge and insights into The Art of Execution book, offering valuable lessons on how investors handle mistakes and recover from losses, how to turn losing investments into winners, and more. His expertise lies in understanding investor behavior and translating those patterns into actionable investment strategies.

Key Insights

1. A Losing Bet Is Not Always a Loss, Unless You’re a “Rabbit”

In his research, which later formed the basis of the book, Freeman-Shor set a clear condition for participants: They were to start by investing in the ten ideas they believed had the most potential. As you can imagine, not every promising idea can become successful. However, the author does not focus on ideas but on investors. More precisely, on the types of behavior in case of losses: the Assassin, the Hunter, and the Rabbit.

The Assassin takes a disciplined, cold-blooded approach by eliminating underperforming stocks after a set period, while the Hunter seeks to capitalize on declining stocks, buying more at lower prices with the hope of a future rebound. Both strategies are effective and share a key trait: decisive action in the face of loss. This proactive behavior sets them apart from the final and loss-only role model, the Rabbit, which represents inaction in the face of adversity.

Successful stock market investing is not about being right per se – far from it. It comes down to how great ideas are executed.
— Lee Freeman-Shor, The Art of Execution

The Assassin and Hunter used their respective strategies to recover from losses, break even, or even turn a losing position into a profitable one. In contrast, the Rabbit took no action, holding all 10 shares and relying on hope for recovery. From Freeman-Shor’s observations, this passive approach typically resulted in mounting losses in the short term (1-3 years), especially when stocks continued to decline or market conditions became unfavorable over time.

As history shows, markets eventually recover and reach new highs after even the most significant downturns. Although Rabbit's stance may take more than 3 years to recover, markets usually do so, allowing their investments to benefit from natural market recoveries.

This explains how Rabbits also made profits, although the pace was significantly different from the Assassin and the Hunter. A short-term horizon may indeed demand more active strategies, but the most effective balance between risk and return has always been achieved by focusing on the long term.

2. Racing on Winning Stocks Does Not Build Wealth

Investor behavior in a winning scenario is even more intriguing than in a losing one. Here, the author identifies two distinct patterns of behavior. One group – Raiders – harvests their gains too early, settling for small victories. The other group, Connoisseurs, however, savor the experience, allowing the fruits of their patience to ripen.

Raiders sell their shares prematurely for many reasons, all driven by emotion. Some fear a potential market downturn and sell at the first sign of profit, others grow bored with their positions, and some simply can’t resist the urge to lock in gains. In most cases, these investors later regretted their haste.

The author suggests adopting the Connoisseur's approach, as successful investing is a long-term commitment. Much like a winemaker who lets grapes mature in the sun, the Connoisseur allows investments to flourish over time, maintaining a patient and strategic approach. A prime example of this mindset is Warren Buffett, the renowned advocate of the buy-and-hold long-term investment strategy. His approach can help investors avoid the pitfalls of short-term thinking and achieve lasting success, a model for many investors.

The Connoisseur demonstrates the necessary mindset for sustainable growth by holding onto winning stocks and allowing them to increase in value. While the short-term approach may lead to quick profits, as exemplified by Raiders, it often resembles betting, with less predictable outcomes. Value investing, in contrast, is focused on the long term, where patience and discipline tend to yield more consistent rewards — an approach that most prudent investors, like Seth Klarman and Warren Buffett, always favored.

3. Analytical Skills Are the Key to Success

There is nothing like an idea whose time has come. In investing, a lot of success can be attributed to being in the right place at the right time – otherwise known as luck.
— Lee Freeman-Shor, The Art of Execution

Having analyzed every investor's behavioral pattern, one might wonder if the Connoisseur and the Rabbit are the same. Both hold onto their shares and wait, so why do Rabbits always seem to come up short?

The similarities between the Connoisseur and Rabbit are only superficial; waiting for investments to mature is not the same as doing nothing. Just as wine fermentation requires careful monitoring and patience, successful investing involves strategic decision-making. While the Rabbit simply bides its time, Connoisseurs remain vigilant and are prepared to adjust their strategy as necessary.

For instance, ultra-high-net-worth individuals often shift from traditional 60/40 portfolios of stocks and bonds to a more diversified mix of public and private assets. This flexibility in strategy ensures that investments can adapt to changing market conditions and continue to grow effectively.

Final Thoughts: Incorporate Winning Behaviors in the Portfolio

Raiders are often Rabbits when they are losing – and the combination is fatal.
— Lee Freeman-Shor, The Art of Execution

Lee Freeman-Shor doesn’t categorize the five behavioral patterns as fixed temperament types. Given the market's inherent volatility, with every stock experiencing its share of highs and lows, investors often display a blend of behaviors — one for handling winning positions and another for dealing with losses.

A Connoisseur can adopt the disciplined approach of a Hunter, but combining the Assassin’s and Hunter’s strategies is challenging because they represent fundamentally different approaches. The author himself recommends imitating the combination of the Connoisseur and the Assassin: run wins and cut losses.

On the negative side, any investor can be a Rabbit. However, on the positive, being a Rabbit is only a losing strategy if an investor can’t self-reflect and take a proactive approach to break free from such a mindset. The book is therefore food for thought that allows investors to self-reflect on their behavioral tendencies and can help them adopt effective execution strategies to improve their returns.

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