A practical framework for making better decisions, managing risk, and finding opportunity in unpredictable environments. We contrast these principles with the massive $2.9 trillion AI data center build-out by Big Tech, which is betting big on a single superintelligence future. Show Notes Inside the relentless race for AI capacity—The Financial Times Inside the AI race: can data centres ever truly be green?—The Financial Times The Kanye/Data Center Crossover by Paul … [Read more...]
520: Where Are We Heading?
In this episode, we explore what it means to invest in a non-ergodic world—where time, not averages, determines outcomes. We unpack concepts like volatility drag, ensemble vs. time averages, and the implications for portfolio strategy, while also reflecting on how AI and zero-click search are reshaping business and investor behavior. Topics covered include: Show Notes Wayback Machine: jdstein.com Probabilities and Payoffs: The Practicalities and Psychology of Expected Value … [Read more...]
496: Are You Taking Enough Aspirational Risk?
Why we need distinct risk buckets: balancing our natural loss aversion with the allure of opportunities that offer the potential for massive upside. Topics covered include: Show Notes Portfolio Selection by Harry Markowitz—The Journal of Finance, Vol. 7, No. 1. (Mar., 1952), pp. 77-91 Safety First and the Holding of Assets by A. D. Roy—Econometrica, Vol. 20, No. 3 (Jul., 1952), pp. 431-449 The Misbehavior of Markets: A Fractal View of Financial Turbulence by Benoit … [Read more...]
486: How Retail Traders Lose Big While Enriching Wall Street
Gambling in the stock market is increasing, with most traders losing money while generating billions of dollars per year for brokerages and wholesalers. Will all this trading lead to big market swoons? Topics covered include: Show Notes How Stocks Became the Game That Record Numbers of Americans Are Playing by Claire Ballentine—Bloomberg MURPHY, GOVERNOR OF NEW JERSEY, ET AL. v. NATIONAL COLLEGIATE ATHLETIC ASSN. ET AL. SYLLABUS—The Supreme Court of The United … [Read more...]
482: Unlocking the Power of Positive Skewness: Strategies for Investing, Business, and Creativity
How a few high-impact successes drive up overall average outcomes in investing, business, and creative projects. How to harness positive skewness using a barbell approach. Learn when to mitigate risks and when to embrace them. Topics covered include: Show Notes Long-Term Shareholder Returns: Evidence from 64,000 Global Stocks by Hendrik Bessembinder, Te-Feng Chen, Goeun Choi, K.C. John Wei—SSRN Long-Horizon Stock Returns Are Positively Skewed by Adam Farago and Erik … [Read more...]
460: Should You Be Invested 100% in Stocks Before and During Retirement? A Recent Study Says Yes.
The pros and cons of investing your retirement assets 100% in equity, including half in international stocks. Why the 4% spending rule is too aggressive. Topics covered include: Show Notes Beyond the Status Quo: A Critical Assessment of Lifecycle Investment Advice by Aizhan Anarkulova, Scott Cederburg, and Michael S. O'Doherty—SSRN The Safe Withdrawal Rate: Evidence from a Broad Sample of Developed Markets by Aizhan Anarkulova, Scott Cederburg, Michael S. O'Doherty, and … [Read more...]
451: How Much Should You Invest in Stocks? The Art of Position Sizing in a Volatile Market
Our allocation to risky assets should vary based on the expected return, volatility, risk aversion, and how much we can earn risk-free. That means we should be taking less risk right now. Listen to learn why. Topics covered include: Show Notes How to avoid a common investment mistake - Buttonwood - The Economist The Missing Billionaires: A Guide to Better Financial Decisions by Victor Haghani and James White Money For the Rest of Us List of Most Influential … [Read more...]
