Enterprising Investor
Practical analysis for investment professionals

Portfolio Management


Why Static Portfolios Fail When Risk Regimes Change

Why static portfolio frameworks fail when risk regimes shift, drawing lessons from the very different market breakdowns of 2020 and 2022.

What the Market Knows That WACC Doesn’t

Market-implied discount rates reveal how investors price risk, often diverging from WACC and reshaping capital decisions.

Attention Bias in AI-Driven Investing

AI tools may favor popular stocks over overlooked ones, embedding attention bias into investment decisions.

Where AI Ends and Investment Judgment Begins

AI’s growing capabilities challenge traditional investment skill, shifting competitive advantage toward governance, process, and judgment.

Three Risks of Relying on the S&P 500 in Retirement Planning

Why S&P 500 reliance can undermine retirement outcomes, and how diversification, valuation discipline, and withdrawals reshape long-term portfolio risk.

Why Tight Stop-Losses Often Hurt Investors — and What Robust Capital Growth Really Requires

Tight stop-losses feel disciplined but can erode long-term returns. Robust investing favors resilience over optimization.

Book Review: A Dollar for Fifty Cents

Closed-end funds have their place in a diversified portfolio, but investors shouldn't expect to make a quick buck.

Shifting Tides in Global Markets: The Reemergence of International Investing

With valuations stretched in the US, international markets are emerging as a compelling new source of growth.

How US State Capital Is Reshaping Strategic Supply Chains

US government equity is entering strategic supply chains. For investors, this is changing how risk, returns, and capital allocation are priced.

Incentives Are Dangerously Aligned in Private Markets

Private markets increasingly resemble a speculative supply chain, where rational actors and aligned incentives quietly compound systemic risk.