Somewhere I have heard that it is very important to ask the right questions (probably my wife Ellen, the retired lawyer). One question that we forgot to ask Fred during our interview yesterday was about his worst investment. How it felt? What went wrong? When did he know it was a “goner”as “Arthur” would say, and what he would have the company do differently if he could do it again? Would he even make the investment?

Everyone has a big one.

I have had many. My most stupid and I have written it before was Cars Direct.com. No plan, no margins, silly valuation, pure greed on my behalf.

The one that did the most damage to my life was another which needs to be written about. It is long and full of drama and I have bits and pieces in saved posts over the last year. In hindsight, I never asked the right questions, before or during the investment. Unfortunately, during the clean-up from a bad investment, the answers to the questions you should have asked are vomited all over you. The smell sticks and that is why you likely learn more from the mistakes.

The good news is that I ask them more often these days. Not always obviously. Nobody does or can.

Fred will be bugged for a follow-up!