I’ve never been with a winner. Well, except that streak when the North Carolina Tar Heels won the NCAA Basketball tournament and the St. Louis Cardinals won the World Series and Peyton Manning and the Colts won the Super Bowl.
That was an outlier.
The problem is, I don’t tend to pick my “teams” based on winner criteria. For example, at the onset of my legal career when I was choosing law firms, I didn’t make my decision based on where I could make the most money or whether the firm was considered “the best” in the state. I looked at a firm’s history: during Mississippi’s Civil Rights wars, which side was the firm on? As a result, the firm I joined was not the one at the top, the “winner” in the eyes of a state that really wanted to forget its Civil Rights history. It was simply the most principled law firm in town.