Pegging the Meter

we have surpassed insanity at this point

Late in 2005, with some of the proceeds of my sale of Prophet.net to Investools, I used $350,000 to purchase a 5% stake in a very small software-as-a-service company. Shortly after doing so, a friend of mine assured me that it would probably be worthless in the end, which I found a little disheartening.

Within a few years, I had sold off a small portion of my stake for over twice the entire investment, providing me a handsome return and the psychological assurance that, even if the company became worthless, I had already more than doubled my money. That felt pretty good, particularly considering that, to this day, I still own most of the shares.

That was a long time ago, however, and I'm starting to wonder if those remaining shares will ever pay off. The company is still around, now twenty years after its creation, which is a fact by itself that makes it a success. Since I can't help but torture myself, however, I occasionally pop over to the Woulda Shoulda Coulda page just to see what the same $350,000 would have yielded.