It's tough for me to answer the question of "what is your worst investment?" because I've made so many bad ones in the brief time since I've joined this game we call investing. That said, one stands out as a particularly poor outcome, but a particularly great learning event.
Matterport is an interesting company. It sells itself as a platform for the digitization of the built world. With the current direction of the world, I loved the story, but precisely at the wrong time -- and at a time when valuation was the least of my concerns (now it is the highest of my concerns).
I bought into the company at a multiple of over 20x sales! I held it for several months and slowly came to the realization of my error. But so did the market. The stock continued to drop from where I bought it, and my mental anguish at my mistake continued to rise until I made the decision to cut the fat and recognize a lesson learned. I never lost confidence in the 10-year story, but I lost confidence that my returns would make sense given the risk.
Looking back on this experience, a few things stand out:
- Valuation matters -- a lot -- for future return expectations.
- Overpaying for a business can create a mental drag that impacts your thinking.
- Sometimes it's better to just get out, reset your thinking, and move from there.
- Don't be afraid to take a loss.
These lessons aren't universal, but they are a few things I picked up from making what I believe to be an error early in my investing journey.