Enterprising Investor
Practical analysis for investment professionals

Risk 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.

Attention Bias in AI-Driven Investing

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

AI Is Reshaping Bank Risk

AI is exposing the limits of legacy bank controls, making governance quality critical to resilience and investor confidence.

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.

AI Strategy After the LLM Boom: Maintain Sovereignty, Avoid Capture

Yann LeCun’s testimony reframed for investment leaders: why AI sovereignty, platform control, and LLM economics shape organizational risk.

America’s Debt – A New Infrastructure?

US debt increasingly functions as market infrastructure, shaped by who holds it and how systems like stablecoins are reshaping Treasury demand.

Defined Contribution Top Trends for 2026: What Plan Sponsors Need to Get Right

Key trends shaping US defined contribution plans in 2026, from technology and education to investment strategy, regulation, and plan design decisions.

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.

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.