Enterprising Investor
Practical analysis for investment professionals

Investment Topics


Rethinking Household Asset Allocation Under Capital Constraints

Leveraged ETFs aren’t about more risk, they’re about using less capital to achieve a desired risk profile in household portfolios.

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.

Decoding CTA Allocations by Trend Horizon

Decompose CTA returns into fast, medium, and slow trend horizons to reveal true risk drivers, benchmark overlap, and behavior during market stress.

Keynesian Folly: Why AI Will Never Fully Automate Finance

AI automates tasks in finance and boosts efficiency, but reflexive markets ensure interpretation and oversight remain irreducibly human work.

Auditor Specialization: A Signal for Financial Analysts

For financial analysts covering government contractors across defense, healthcare, and IT, auditor specialization signals earnings quality, reporting credibility, and filing timeliness.

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.

Synthetic Risk Transfers Are the Talk of the Town. But Are They as Scary as They Look?

SRTs help banks free up capital, but growing use has raised concerns about rollover risk, investor concentration, and leverage.