Insider trading by investment bankers: a conundrum given poor risk/reward

In the financial news today was an article about three investment bankers getting charged for running an insider trading scheme. The bankers worked at Goldman, Moelis and Centerview, and the scheme ran from 2012 to 2018 targeting M&A deals mainly in the pharma space. Along the years there’s been many other similar cases, ranging from a Lazard managing director who passed on tips to fund his affair with a mistress, to SAC Capital’s gigantic insider trading operation.

In a general sense I can understand the urge to engage in insider trading. It’s simple. Greed is a basic instinct. But it’s difficult to understand why certain people can’t suppress that urge given that the risk/reward seems unfavorable. I use the word “seems” here because there is a chance that my assumptions are wrong; perhaps only a fraction of people get caught and that the smartest ones end up making a crazy amount of money consequence free.

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Rookie mistake #1 in investing: selling near cyclical troughs

Rookie investors will often say something like this: “PMIs are tanking, GDP growth is decelerating, labor market is loosening, sentiment is awful, stocks are down…so we should sell stocks of companies with high cyclicality, high operating leverage, and high financial leverage!”

That is Rookie Investor Mistake #1. Because more often than not, that is the precise moment when you should be thinking about holding onto existing positions and initiating new positions. That is often the moment when you want to be getting into the crappiest, most financially and operationally levered businesses. The difficulty arises because the rookie (and many veterans too) fears there’s no bottom to the decline, that this downturn is going to get much worse, that stocks could go down another 50%. Even when historical perspective would suggest that things would start getting better over the next while (let’s say 1-2 years) instead of devolving into the next Great Depression.

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