The most-read blogs published on Enterprising Investor between April 1 and June 30 captured a profession in motion, grappling with disruption, uncertainty, and legacy. While the topics varied, several themes emerged:
- AI and the analyst’s edge: Investment professionals are thinking seriously about how to work with, rather than be replaced by, AI. Q2’s top reads explored bias, prompting, model performance, and what it means to stay competitive in an AI-driven world.
- Rethinking portfolio construction: From stretched market concentration to small-cap rotation and Bayesian frameworks, readers dug into smarter ways to diversify and position portfolios amid regime shifts.
- Learning from the long view: History, macro forces, and global politics loomed large in Q2 content. Readers looked to the past, not for nostalgia, but for data-driven insight into future risks and returns.
1. Vices, Virtues, and a Little Humor: 30 Quotes from Financial History
Mark J. Higgins, CFA, CFP, and Rachel Kloepfer deliver a sharp, unsentimental reminder that financial folly is nothing new. These quotes from centuries past expose the recurring misjudgments, overconfidence, and occasional brilliance that continue to shape markets today.
2. Market Concentration and Lost Decades
With the top 10 US stocks now representing more than a third of market cap, Bill Pauley, CFA, Kevin Bales, CFA, and Adam Schreiber, CFA, CAIA, explore what history tells us about such extremes. Elevated concentration and stretched valuations have often preceded long periods of underperformance, underscoring the need for a more intentional approach to diversification.
3. Small Caps vs. Large Caps: The Cycle That’s About to Turn
Daniel Fang, CFA, CAIA, draws on market cycle history, rate-driven migration dynamics, and relative valuations to make the case for a small-cap comeback after more than a decade of underperformance.
4. How Tariffs and Geopolitics Are Shaping the 2025 Global Economic Outlook
Kanan Mammadov examines how inflation, economic divergence, and a surge in protectionist policy are reshaping global markets in 2025. With trade tensions escalating and market volatility rising, he argues that investors must adjust forecasts and strategies to account for cross-border risks and policy shocks.
5. Two Enduring Legacies, One Oracle’s Exit, and “Buffett’s Alpha”
This post reflects on Warren Buffett’s retirement and how the award-winning Financial Analysts Journal article “Buffett’s Alpha” helps explain his long-term success. I weave together the legacy of a legendary investor with the 80-year history of the Journal, reminding readers that outperformance may be rare, but it’s not necessarily mysterious.
6. AI Bias by Design: What the Claude Prompt Leak Reveals for Investment Professionals
This forensic look at a leaked Claude system prompt reveals how embedded instructions can distort financial analysis by reinforcing bias, overstating fluency, and simulating reasoning. Dan Philps, PhD, CFA, and Ram Gopal argue that without explicit safeguards, investment professionals risk mistaking AI-generated coherence for insight and inheriting flawed assumptions at scale.
7. Tariffs and Returns: Lessons from 150 Years of Market History
Drawing on one of the most comprehensive long-term datasets available, Guido Baltussen, PhD, Joshua Dekker, Michael Hunstad, PhD, Bart van Vliet, CFA, and Milan Vidojevic, PhD, explore how tariffs have historically influenced growth, volatility, and asset class performance. Their analysis reveals that while protectionism often raises macro risks, equity style factors, especially low volatility, have consistently provided resilience across high-tariff regimes.
8. Outperformed by AI: Time to Replace Your Analyst?
In a head-to-head test, top AI models outperformed human analysts in generating detailed SWOT analyses — especially when guided by advanced prompting. Michael Schopf, CFA, argues that the future of investment research belongs to those who can combine model selection, prompt engineering, and human judgment into a competitive edge.
9. AI in Investment Management: 5 Lessons From the Front Lines
Markus Schuller, Michelle Sisto, PhD, Wojtek Wojaczek, PhD, Franz Mohr, Patrick J. Wierckx, CFA, and Jurgen Janssens outline five key lessons on how AI is reshaping investment workflows. From boosting early-career productivity to raising ethical and regulatory concerns, this post emphasizes the need for critical thinking, explainability, and intentional integration to unlock AI’s value responsibly.
10. Bayesian Edge Investing: A Framework for Smarter Portfolio Allocation
Sandeep Srinivas, CFA, introduces a dynamic, evidence-updating framework that helps investors calibrate conviction, detect mispricing, and allocate capital more intentionally.
Rooted in Bayesian reasoning, the approach reframes rationality as adaptive judgment — where clarity, not certainty, gives investors a lasting edge.
Looking Ahead
These were the most-read blogs published on Enterprising Investor between April 1 and June 30, a quarter that reflected a profession balancing innovation with insight. Whether wrestling with the implications of AI or revisiting the lessons of financial history, our readers show deep curiosity and a continued hunger for rigor.
