Enterprising Investor
Practical analysis for investment professionals

Risk Management


Low Probability of Loss: Why It Doesn’t Equal Low Risk in Investing

In golf, a hole-in-one is a remarkable feat. The odds? Roughly one in 850,000 from a distance of 150 yards – practically a statistical anomaly. Yet, the 2023 LPGA tour recorded 20 such occurrences. How can this… READ MORE ›

Book Review: The M&A Failure Trap

Massive M&A deals make headlines but too rarely make money for stockholders.

Escaping the Benchmark Trap: A Guide for Smarter Investing

Is it time to eschew the benchmark trap in favor of Warren Buffett's rule, "Don't lose capital?"

From Tweets to Trades: The Risks of Social Media in Investing

Are you able to step outside the confines of social media echo chambers to make informed investment decisions?

AI’s Game-Changing Potential in Banking: Are You Ready for the Regulatory Risks?

As regulators continue to refine their understanding of AI and big data, financial institutions have an opportunity to shape the regulatory landscape by participating in discussions and implementing responsible practices.

Identifying Crises and the Economic Significance of Avoiding Them

By minimizing exposure to severe market downturns, investors can achieve higher risk-adjusted returns, preserve capital, and avoid the psychological toll of significant losses.

How to Think About Risk: Howard Marks’s Comprehensive Guide

Howard Marks’s approach to risk emphasizes the importance of understanding risk as the probability of loss, not volatility, and managing it through careful judgment and strategic thinking.

Navigating the Risks of AI in Finance: Data Governance and Management Are Critical

Big data-driven AI in financial services is a technology that augments human capabilities. We are living in countries governed by the rule of law, and only humans can adopt safeguards, make decisions, and take responsibility for the results.

Market and Model Risk: Sequentially Interweaved Risk Dimensions

Risk managers must look at market and model risk through a single lens to see the complete picture of their market-related investment and trading risks, as well as management costs, complexities, time, and regulatory requirements.

Mitigating Economic Risk in Multi-Factor Strategies

Here's a weighting scheme to mitigate economic risks while preserving the benefits of diversified multi-factor strategies.



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