Enterprising Investor
Practical analysis for investment professionals

Risk Management


Vices, Virtues, and a Little Humor: 30 Quotes from Financial History

This collection of quotes from US financial history offers timeless lessons in vice, virtue, and investing wisdom for every generation.

AI Bias by Design: What the Claude Prompt Leak Reveals for Investment Professionals

A leaked AI system prompt reveals hidden biases in Claude's outputs. What every investment professional should know about using LLMs effectively.

How Clients’ Investment Goals Reflect Risk Behavior and Hidden Biases

Successful investing isn't just about numbers. It's about aligning strategy with the stories people believe about their future.

Rethinking the Institutional Mandate: A Compilation from Enterprising Investor

Here's a curated look at where institutional investing is under strain—and where forward-looking strategies offer paths to improve performance, oversight, and alignment.

Resilience Is the New Alpha: Rethinking Risk in a Fragile World

The market has stopped applauding good intentions and started testing whether companies can withstand the world's mess.

Social Norms Shape Investment Behavior. What Can Advisors Do About It?

Note to financial advisors: It’s time to embrace the norm effect and rethink how we influence investment decisions.

How Tariffs and Geopolitics Are Shaping the 2025 Global Economic Outlook

The year is unfolding beneath the weight of mounting geopolitical risks and structural divergences, The challenge for investors isn’t just to react, but to interpret, prepare, and adapt.

Market Concentration and Lost Decades

Modern portfolio theory has taught professional investors the benefits of diversification. Maybe it is time to diversify in a more intentional way to reduce extreme market concentration.

Private Equity and Private Debt: Two Sides of the Same Coin

Explore how the growing convergence of private equity and private debt is transforming risk dynamics, return strategies, and regulatory concerns across the private capital landscape.

Quality of Earnings: A Critical Lens for Financial Analysts

Quality of Earnings: By approaching financials with this sharper lens, analysts can not only anticipate problems but also identify opportunities that align with long-term value creation.