Insights
No, this study won’t tell you how to be a successful investor
Key takeaways The Bessembinder study is rigorous research, but the popular MarketWatch interpretation oversimplifies it into “stock picking is a lottery, so buy index funds.” Measuring lifetime buy-and-hold returns does not reflect how real investors
8 hidden risks of passive investing
Key takeaways Passive funds now hold over 55% of U.S. fund assets, but their popularity doesn’t eliminate structural risks. The top 10 S&P 500 holdings represent roughly 37% of the index, creating concentration risk that
Every sailing metaphor used in finance (that we could find)
If you’ve ever noticed that financial writing is stuffed with sailing metaphors, you’re not alone. Pundits talk about headwinds and tailwinds. Analysts warn of choppy waters. CEOs claim to be staying the course. The language
How to reduce portfolio concentration risk
Portfolio concentration risk develops quietly. A single stock performs exceptionally well, your employer grants you stock options year after year, or you inherit shares from
Five risks DIY FIRE planning can overlook
The FIRE math is straightforward: save aggressively, invest consistently, and build a portfolio large enough to sustain your lifestyle indefinitely. But between your first spreadsheet
No, this study won’t tell you how to be a successful investor
Key takeaways The Bessembinder study is rigorous research, but the popular MarketWatch interpretation oversimplifies it into “stock picking is a lottery, so buy index funds.”
RSUs vs Stock Options
Tax planning for equity compensation in 2025
How to invest when you have RSUs
3 hazards for employees with stock-based compensation
8 hidden risks of passive investing
How the SpaceX IPO makes index funds less diversified
Dangers of Index Funds
8 hidden risks of passive investing
Last minute tax tips for your 2025 return
How the SpaceX IPO makes index funds less diversified
How to tell if your financial advisor is using AI
Every sailing metaphor used in finance (that we could find)
Tax planning and tax preparation aren’t the same thing
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