Enterprising Investor
Practical analysis for investment professionals

Portfolio Management


Backtests, Causality, and Model Risk in Quantitative Investing

Beyond backtests, a layered view of association, causality, and reflexivity can reduce model risk in quant investing.

Geopolitical Risk and Portfolio Oversight

A framework for identifying material geopolitical shocks, translating them into portfolio impacts, and documenting risk for oversight and governance.

Aligning Allocation to the Global Business Cycle

Static portfolios lag macro shifts. Predefined cycle triggers help practitioners adjust risk before markets reprice.

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.