Learning from the Losses
Many years ago, there was a short period where I made my two worst startup investments. I don’t define “worst” based on the outcomes (which were poor) but on the basis of “I should have known better” with the information & resources available to me at the time.
Not coincidentally, this period came right after a few of my earlier investments had emerged as solid winners. With the benefit of hindsight, I can see that success made me overconfident. I promptly let my filter loosen and invested in a few duds. Lesson learned!
Some losses are easier to digest than others. For me, it’s much easier to forgive myself for making a money-losing investment when the founders fight to the very end. It’s the ones where they didn’t - those are the ones that are hardest to let go. That also makes the lessons they provide more impactful. A very expensive consolation prize, I suppose.