Whirligig Bear | Andrew Courtney | Substack

Whirligig Bear

You've been putting it up your whole life, you just didn't know it.

By Andrew Courtney

· Over 1,000 subscribers

On Bet Sizing, part 1

Your bankroll is your utility function, not your account balance

May 14•Andrew Courtney

Legibility

When insider trading becomes a national security issue, not just a financial one

Apr 27•Andrew Courtney

Are traders on Kalshi being profiled?

And on Polymarket -- what did you think Copy-Trading was all about?

Mar 17•Andrew Courtney

Don't just put the chart on the screen

What's missing when journalists cite prediction markets

Jan 16•Andrew Courtney

Mostly Beta

What was the R^2 of my own effort on my career?

Jan 1•Andrew Courtney

Prediction Markets: Truth Engine or Casino? A Scoring Framework

Plus a rant about gambling and a few hot takes

Dec 9, 2025•Andrew Courtney

ChatGPT + $20k + Grammys

The opposite of adverse selection

Nov 17, 2025•Andrew Courtney