151 Items
Tax Matters
Demystifying 351 ETF Exchanges
Investors have learned to love the ETF as an investment vehicle, and for good reason - but for investors holding assets with unrealized gains in taxable accounts, making the switch can seem unattractive.
Published March 6, 2026
Investing 101
Concentrating on Concentration
The US stock market is heavily concentrated in a handful of technology companies, and many investors and commentators find this alarming - arguing that such concentration makes the market riskier.
Published February 26, 2026
Investing 101
An Endowment Asked Us for Some Advice
Many of us sit on the advisory boards and investment committees of university endowments, charitable foundations, or family trusts, and several have recently asked us what big recommendations we'd make for their institution's investing process.
Published January 15, 2026|8 min
Investing 101
Our Readers' Expectations of a Stock Market Crash
Thank you to the hundreds of readers who submitted their estimates for the probability of a stock market crash over the coming year - though the data we received wasn't quite what we were expecting.
Published December 18, 2025|6 min
Featured Insights
How Likely is a Stock Market Crash?
Is a stock market crash just around the corner? It's a question on a lot of investors' minds these days - in this note, we'll explore a few different approaches to answering this question, including a detailed explanation of our favorite.
Published December 2, 2025|11 min
Investing 101
Leverage: Sense and Non-Sense
There's a lot of leverage in the US stock market right now, and it raises an interesting question: when does it make sense to borrow so you can own more stocks than the value of your wealth?
Published November 20, 2025|9 min
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Investing 101
Extrapolators Beware The Money Pump
A "money pump" is a process that extracts money from a person with strange preferences and transfers it to the pumper in a nearly sure way. No one would want to be subject to a money pump, yet the target would find himself making choices he'd be quite happy with.
Published November 5, 2025|8 min
Featured Insights
Essential Wisdom from Twenty Personal Investing Classics
Twenty of the most influential voices in personal finance converge on a unified message: successful financial decision-making requires discipline, humility, and knowing that complexity is the enemy.
Published October 29, 2025|16 min
Investing 101
The Permanent Portfolio's Temporary Appeal
A number of clients have asked us about a recent Buttonwood column describing the "Permanent Portfolio" strategy. Are appealing returns enough to override the basics of asset allocation?
Published October 23, 2025|3 min
Risk and Return
The Impact of U.S. Stock Buybacks: Theory vs Practice
U.S. stock buybacks are on track for a record in 2025 - but they also raise important questions.
Published October 6, 2025|7 min
In the News
Can Rational People Truly Disagree? Lessons from our interview with Robert Aumann
What happens when brilliant minds clash on the facts? Nobel Prize winner Robert Aumann reveals his groundbreaking mathematical proof that rational people with the same basic assumptions cannot agree to disagree - and what this means for markets, conflict, and human cooperation.
Published September 18, 2025|6 min
Featured Insights
Riding the Wheel of Fortune: A Practical Guide to Lifetime Investing and Spending
We steer our financial course through life choosing how much to spend and how to invest what's left, periodically updating our choices as circumstances evolve. It's a pretty simple problem to put into words, but finding an optimal solution has occupied some very bright minds since Harry Markowitz got the ball rolling 60 years ago.
Published September 11, 2025|8 min