Red Sox owner John Henry, who runs a hedge fund, recently talked about baseball trades. He think the best trades are the ones the fans don’t like. In other words, they are contrarian moves.

All this made me think about entrepreneurship. When do you hold vs. fold? Are you being unreasonable and, in fact, crazy if you give up? Or, are you simply being “gritty” by staying course?

Honestly, I personally believe the “hold vs. fold” thought process is the key decision that an entrepreneur and his/her Board has to make. And, you have to make it more than once in a company’s life. IMO, it’s the “management alpha” that generates superior risk-adjusted investment returns.

Much of that alpha is in making contrarian decisions. For example, there’s an incredibly insightful post on that from Tren Griffin, called “A Dozen Things I’ve Learned from Jim Breyer.”

I really liked the comments about being a contrarian, how you do really well as a founder or a VC when you’re not pursuing what others are. It takes a lot of internal strength to be OK when other people don’t like your idea.

In fact, I remember at one point there was a particular VC firm going through some tough times. Some friends worked there, and they were pretty stressed out. They tried to restructure some of their funds, and their LPs voted against it. There was fall-out, and some prestigious LPs spoke very loudly that they were dropping the VC firm.

But, the VC firm mentioned above persevered. And, it invested in Facebook, which has been the most successful VC investment of all time.

The VC? Jim Breyer.