I recently collaborated with WSJ's Gunjan Banerji on a project where she provided ChatGPT with the profile of an investor, and prompted it to suggest an appropriate portfolio. The result is this article, published earlier this week: During the process, I kept thinking about Kasparov vs. Deep Blue. I was a competitive chess player as a kid, and the original match took place in 1996 (when I was 12). At the time, there was serious debate about whether computers would ever consistently outplay...

Most investment problems are overreach problems. We want something to happen and then overestimate the probability that it will. Or a marketing campaign for some investment product seems almost too good to be true, and it ends up, after you buy it — you'll kick yourself — but being too good to be true. You end up paying high fees for an underperforming "solution" that had a marketing budget to go find problems. Investors desperately want panaceas, silver bullets, and ways to outperform....

(the one we don't make) My annual rite — to bastardize the legacy Wall Street ritual of forecasting how markets will perform the next year. Through January and into February, my firm sits down with each client family to map out the year ahead together, including an overview of their investments. We provide both short-term and long-term expectations for their portfolio. This is what we will tell clients to expect in 2026 (i.e. the short-term): Of course there are people who will think this is...