Sixty-40Play

Lessons

The ideas behind the wheel, in plain English. Every essay uses real positions from the game — the winners, and the ones that went to zero.

Buffett's million-dollar bet against hedge funds — and why the boring option keeps winning

How a cheap S&P 500 index fund beat a hand-picked team of hedge funds over a decade, and what fees, logic and human nature tell us about the result.

5 min read

Hindsight bias: why every crash looks obvious afterwards

Why the dot-com bust and 2008 crash feel obvious now, how hindsight and outcome bias distort our memory, and practical ways to guard against them.

5 min read

Ten famous busts and what they had in common

Enron, Lehman, Pets.com, Webvan, Pan Am, Blockbuster, Wirecard, Terra Luna, FTX and Beanie Babies: the patterns that keep repeating in famous collapses.

5 min read

Survivorship bias: the graveyard behind every winning stock chart

Why winning stock charts mislead: the bombers, the delisted stocks, the closed funds and the countries that quietly drop out of investing history.

5 min read

What it actually took to hold a ten-bagger

Amazon, Apple, Nvidia, Netflix and Bitcoin all multiplied tenfold, but holders had to sit through crashes of 50% to 90%. What that journey really involved.

5 min read

Rolexes, Birkins and Pokémon cards: do collectibles really beat the stock market?

Watches, handbags and trading cards make great headlines. Costs, liquidity, fakes, fashion and survivorship explain why they rarely beat stocks.

5 min read