I want to tell you three stories about decision-making that illustrate how the “obvious” route often leads to a dead end. These are three instances in which being stupid saved my ass and my bottom line. Then, at the end, I’ll try to leave you with a recipe for how you, too, can win at business by being stupid.

Story #1

The setup:

Prior to the real estate meltdown of 2008, I owned almost 100 residential properties. Things were going well, and my holdings were appreciating so fast that I was gaining upwards of 15% per year. Despite this, based on some…