Enterprising Investor
Practical analysis for investment professionals

Leadership, Management & Communication Skills


Women in Alts: Leading with Inspiration, Intuition, and Impact

Women investors are redefining alternatives with bold leadership, values-driven decisions, and long-term impact.

Vices, Virtues, and a Little Humor: 30 Quotes from Financial History

This collection of quotes from US financial history offers timeless lessons in vice, virtue, and investing wisdom for every generation.

AI Bias by Design: What the Claude Prompt Leak Reveals for Investment Professionals

A leaked AI system prompt reveals hidden biases in Claude's outputs. What every investment professional should know about using LLMs effectively.

How Clients’ Investment Goals Reflect Risk Behavior and Hidden Biases

Successful investing isn't just about numbers. It's about aligning strategy with the stories people believe about their future.

Geopolitical Change: Investors Should Focus on the Long Term

In our interconnected world, geopolitical events — ranging from trade disputes and regulatory shifts to conflicts and pandemics — capture headlines and influence market sentiments. As investment professionals, it’s crucial for us to understand these dynamics without… READ MORE ›

Book Review: Buffett’s Early Investments

This book digs into Buffett’s pre-Berkshire investments. The result is a fresh look into the origins of his investment approach.

The Smartest Thing I Ever Did: Women on Life-Changing Decisions

This post highlights inspiring stories from women who took calculated risks, reshaped their lives, and redefined success on their own terms.

Embracing Opportunities: Women in Wealth Management on International Women’s Day

The opportunities for women in wealth management are abundant, driven by the demand for diverse perspectives, the changing demographics of wealth, and the push for inclusive workplace cultures.

Luck vs. Skill: Great Investment Leaders Know the Difference

Our egos are hardwired to fall into the trap of confounding luck and skill. By recognizing the role of chance and reinforcing analytical discipline, investment leaders can build more resilient strategies and teams.

2025 Wealth Management Outlook: Spotlight on Investment Careers

As family offices continue to expand, those who understand their complexities will be well-positioned to lead the next era of wealth management.