Enterprising Investor
Practical analysis for investment professionals

Risk Management


Navigating the Future of Risk Functions: Key Risk Indicators

Key risk indicators help investment teams spot trouble early and stay aligned with strategy, making risk a tool for performance

It’s Not Just What You Own, It’s How Much: Machine Learning and the Portfolio Construction Imperative

AI is reshaping portfolio construction. A real-world case study shows how machine learning enhances allocation, risk control, and performance.

Bear Market Playbook: Decoding Recession Risk, Valuation Impact, and Style Leadership

Explore historical bear markets to decode recession risk, valuation impact, and which investment styles perform best in downturns and recoveries.

Rethinking Research: Private GPTs for Investment Analysis

This chatbot-style tool allows investment analysts to query complex research materials in plain language without ever exposing sensitive data.

Mind the Inflation Gap: Hedging with Real Assets

Timely insights on portfolio risk, inflation hedging, and market cycles—grounded in financial history and written for investment decision-makers.

Buyers Beware: 7 Red Flags That Signal a Private Market Reckoning

Explore red flags in private markets as speculative excess, retail marketing, and valuation risks mount. Lessons from financial history.

Hospitals in Trouble: A Financial Playbook for Leaders and Investors

This post explores the growing wave of financial distress among US healthcare providers and reveals how financial governance failures can quickly erode investor value.

Private Equity Returns Without the Lockups

Explore a new approach to replicating private equity returns with daily liquidity, combining futures, dynamic asset allocation, and risk management overlays.

Clarity by Design: The New Infrastructure for Investment Firms

Investment professionals can’t opt out of complexity, but they can opt into clarity.

Outperformed by AI: Time to Replace Your Analyst?

Discover how advanced AI prompting and model selection are reshaping investment analysis—and why mastering these tools is essential for staying competitive.