Enterprising Investor
Practical analysis for investment professionals

Behavioral Finance


The Question That Exposes Weak Quant Models

Errant variables can quietly undermine even the most statistically impressive quant models.

Three Levers That Drive VC Returns

VC performance hinges on ownership and failure reduction, not just rare breakout wins.

Building Commitment to Long-Term Investing

Why clients stall on long-term investing and how reframing commitment around flexibility unlocks forward momentum.

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.

Lincoln’s Blueprint for Ethical AI

How Lincoln’s approach to innovation, labor, and law offers a framework for ethical AI and long-term value creation.

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.

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.

What Successful Investors Read: Book Recommendations from Professionals

The best investors read widely about people, systems, bias, and failure because investing is more than numbers.

AI in Investment Management: From Exuberance to Realism

AI offers real promise for investors, but reliability gaps and oversight needs mean its impact will be more measured than early hype suggests.