Enterprising Investor
Practical analysis for investment professionals

Investment Topics


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.

How to Value Digital Tokens: A 5-Step Fair Value Framework

How financial analysts can approach digital asset valuation through a structured, five-step fair value framework.

Private Credit Secondaries: From Niche Strategy to Core Portfolio Tool

Private credit’s resale market is booming. Secondaries offer liquidity but reveal growing strain in traditional exits.

Private Markets: Why Retail Investors Should Stay Away

Retail access to private markets is growing, but opacity, illiquidity, and weak governance raise serious concerns for investors.

Book Review: On Progress and Prosperity

A collection of witty insightful essays by Larry Siegel explore progress, investing, and the ideas shaping modern economics.

Design Beats Luck: How AI Taxonomy Can Help Investment Firms Evolve

Without an AI taxonomy, investment firms risk overrelying on agentic AI and underutilizing it for optimal capital allocation.

A Strategic Buyer’s Guide to PE Exits

The line between financial engineering and sustainable value creation in PE exits is thin, and strategic buyers must be prepared to tell the difference.

The Factor Mirage: How Quant Models Go Wrong

Why factor investing often fails in practice — and how causal reasoning helps quant models perform in the real world.

Private Equity’s New Exit Playbook

The rise of continuation funds reflects private equity's longer hold periods for assets amid higher rates and narrowing exit strategies.

Tokenized Money Market Funds: Cybersecurity Lessons from the Digital Cash Frontier

Tokenized MMFs merge blockchain with institutional finance and offer speed and composability but demand airtight cybersecurity and key controls.