67 Items

Risk and Return

Do You Really Want to Be a Billionaire?

Would you risk going broke for a shot at becoming a billionaire? Maximizing extreme wealth can mean taking extreme risks.

September 1, 2026|5 min

Investing 101

Perpetual Futures: Mechanics, History and Purpose

The CFTC recently cleared the way for a new kind of contract - the perpetual future - to trade in the United States, opening the door for platforms like Kalshi and Coinbase...but the decision didn't sit well everywhere.

August 4, 2026

Investing 101

What If Past Returns Were Indicative of Future Returns?

One of the central themes of our research is the importance of investment sizing. We’ve always preferred a more forward-looking approach – and to see why that’s our preference, it’s helpful to be precise about what we mean by 'expected return.'

July 29, 2026|6 min

Featured Insights

Do AIs Make Good Traders, and Do They Make Good Traders Better?

If AI can write code, pass exams, and reason through complex problems… can it beat the market? We put today's leading AI models to the test - and the results may surprise you.

June 17, 2026

Featured Insights

When a $10 Million Tax Break Isn't Worth the Wait

What if selling your startup shares could mean paying little to no federal capital gains tax? QSBS is one of the most powerful and overlooked wealth-building opportunities available.

May 20, 2026

Investing 101

Vanguard's World Stock Market ETF: Is the Whole Better than the Sum of the Parts?

Vanguard's Total World Stock ETF is an elegantly simplistic product...but is simplicity costing you money?

May 4, 2026

Investing 101

Mega-IPOs and Index Fund Mechanics: Much Ado About Nothing?

Rather than worrying about IPO inclusion timing, investors would be better served focusing on the long-term expected returns of the markets they're invested in.

April 20, 2026|4 min

Investing 101

The New Yale Model

Regular readers know we've been evangelizing a unified approach to lifetime investing and spending for a long time, which is why we're so excited about the work Yale Professor James Choi is doing.

March 18, 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.

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.

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.

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?

November 20, 2025|9 min