Simon Evan-Cook, Fund Manager at Downing, launched an investment-focused book club in April 2024, curating a selection of essential books that have significantly shaped his investment philosophy. Below, he shares ten of his favourite and key insights from each work and their relevance to the world of investing.

1. Black box thinking: marginal gains and the secrets of high performance – Matthew Syed

Evan-Cook highlights this book as a pivotal read in understanding the importance of learning from mistakes. Syed explores how the airline industry has achieved a strong safety record through transparency and a commitment to analysing errors. Similarly, successful investors can gain an edge by acknowledging their mistakes, learning from them, and refining their approach.

2. Scale: the universal laws of life and death in organisms, cities, and companies – Geoffrey West

West’s work underscores the impact of scale on various systems. According to Evan-Cook, recognising the benefits and limitations of size is crucial in investment management. He notes that maintaining an optimal fund size ensures flexibility and adaptability, preventing constraints that can hinder performance.

3. The power of habit: why we do what we do and how to change – Charles Duhigg

Duhigg examines the science of habit formation and how individuals can reprogram behaviours for better decision-making. Evan-Cook applies this principle to investing by advocating for consistent, systematic reviews of portfolio quality. Establishing simple, repeatable processes can improve efficiency while avoiding reliance on labor-intensive, reactive strategies.

4. The most important thing: uncommon sense for the thoughtful investor – Howard Marks

Marks offers what Evan-Cook describes as ‘timeless wisdom,’ drawn from extensive investment experience. A key takeaway from this book is the notion that economic predictions are often unreliable, reinforcing the importance of sound investment fundamentals over speculative forecasting.

5. Obliquity: why our goals are best achieved indirectly – John Kay

Kay argues that the most effective way to achieve a goal is by focusing on the underlying processes rather than the end result. For Evan-Cook, this translates into prioritising a rigorous investment strategy over fixating on market trends, ultimately leading to superior fund performance.

6. I may be wrong: and other wisdoms from life as a forest monk – Bjorn Natthiko Lindeblad

Lindeblad’s reflections on humility resonate deeply with Evan-Cook. The book encourages individuals to embrace uncertainty and acknowledge the possibility of being wrong—an essential mindset for investors aiming to make thoughtful, measured decisions rather than impulsive ones.

7. Anti-fragile: things that gain from disorder – Nassim Nicholas Taleb

Taleb introduces the concept of ‘anti-fragility,’ where certain systems not only withstand volatility but benefit from it. Evan-Cook applies this lesson by seeking investments that thrive in turbulent market conditions. He emphasises the value of active fund managers who pivot away from overvalued stocks in favour of resilient assets with long-term potential.

8. Team of teams: new rules of engagement for a complex world – General Stanley McChrystal

McChrystal details how he restructured military operations in Iraq to improve efficiency through decentralised decision-making. Inspired by this approach, Evan-Cook advocates for placing trust in local investment experts who have firsthand insights rather than relying on centralised market forecasts.

9. Safe haven: investing for financial storms – Mark Spitznagel

Spitznagel, a financial strategist and collaborator with Taleb (see Anti-fragile), outlines methods for constructing portfolios that withstand market shocks. This book has influenced Evan-Cook’s emphasis on incorporating defensive strategies to mitigate losses during periods of market instability.

10. Thinking in systems: a primer – Donella Meadows

Meadows provides a comprehensive introduction to systems thinking, illustrating how different components interact within complex structures. Evan-Cook underscores the importance of this perspective in portfolio management, emphasising that successful investors must understand both internal portfolio dynamics and external market forces.

By drawing insights from these influential works, Simon Evan-Cook provides a compelling framework for investors seeking to refine their strategies and achieve long-term success.

Conclusion

Simon Evan-Cook’s selection of books offers valuable lessons in investment strategy, risk management, behavioural finance, and adaptability. A recurring theme across these works is the importance of learning from mistakes, maintaining flexibility, and adopting a holistic approach to portfolio management.  

By integrating these insights into his investment philosophy, Evan-Cook aims to construct resilient and high-performing portfolios - principles embodied in his management of the MGTS Downing Fox Funds.

To read Simon’s original article, visit Ten Tips for Investing Success. I’ve read a lot of books — here are ten… | by Simon Evan-Cook | Medium

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