Jonny was worried that his friend was not going to be retained by his employer after her internship concluded. Given what he had told me and my brain’s oversized gambling module, I suspected there was a bet to be made.

“What’s the line?”, I casually asked. “2-to-1?”, one of us said. “I’ll take the side of her getting hired”, I offered. Etc… Booked!

This looks like a classically horrible bet on my part. Jonny had exponentially more information on the entire situation than I did. However, I suspected, that properly viewed, the little information I had was enough to overcome the information asymmetry.

Their team had released/fired a female the prior week. I thought that the optics of then passing on a female candidate for a new hire could potentially be enough of a factor to place a little money on the line.

Outcome: Jonny’s friend landed the job. Ted got $100 richer.

Note - I think my reasoning was way off. After I got more information about the company and how many people they were hiring I don’t think my “insight” was the least bit predictive.