Enterprising Investor
Practical analysis for investment professionals

Behavioral Finance


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.

Reducing the Cost of Alpha: A CIO’s Framework for Human+AI Integration

How CIOs can slash costs, scale alpha, and modernize their investment engine with a high-impact Human+AI strategy.

Managing Client Fear: The Cognitive Skill Every Financial Advisor Should Master

A simple cognitive trick helps advisors reframe client fear, restore perspective, and guide decisions grounded in long-term goals.

From Sharpe to Pedersen: Why Active Management Isn’t Zero-Sum After All

Sharpe’s arithmetic explained markets at rest. Pedersen’s model shows markets in motion and how active management creates real economic value.

The Augmented LP: 6 Ways AI Can Enhance the Allocator’s Workflow

AI can help LPs structure data, enhance due diligence, and improve oversight, while keeping human judgment central.