I created one of the systems that competed with Ringo / Firefly. It was a great experience, and a long story that I hope to write up fully some day. A short summary:

I had The Similarities Engine up on the very early web for a couple of years. I joined some guys and we created a startup with a good bit of angel financing. It failed, but at the last minute, Firefly bought out the tech and code that we had developed, so our investors got a little back of what they put in.

Now I met my wife when I travelled to Poland to work with the programmers that were developing our product, and she is the best thing that ever happened to me, so I don't have ALL regrets about how the startup failed, but let me tell you about the big regret that I do have.

The code that was written in Poland was never used for anything, as far as I know. The only thing of value that Firefly got out of acquiring us is the patent that I wrote on my recommending algorithm. (Yeah yeah go ahead and give me a bunch of grief here for applying for, and having issue, a software patent. It was 1997, a different world, for one thing.)

Anyway, long story short, it all comes down to this one 20 minute phone call with my CEO, where I had to decide whether to take my patent back and kill the deal where NetAngels would sell to Firefly, or give up my patent in the hopes that Firefly stock would be worth something. Firefly didn't succeed and soon after sold to Microsoft for not much. But if I had killed the deal, I really think my then-fiancée and I would not have gotten married, so I think I chose wisely. However...

That patent of mine. It didn't look like much at the time maybe. But what happened is, over time, the Internet came to it. Big time. The patent describes what is basically THE basic collaborative filtering algorithm, and it issued. Microsoft never did anything with it as far as I know, they just kept it in a drawer so nobody could ever use it against them.

So here's the thing. Recently I asked ChatGPT and Claude how much my patent would have been worth, if I had held on to it. If you have regrets in your life about business deals, if you had a few early shares of Google, or some early bitcoin or something but you sold early, let me tell you, I have you beat. I'll let you see the numbers yourself--type this query into your favorite AI (and maybe do me a favor and post a comment here about what numbers it tells you):

A single individual created patent US 5,749,081. He sold it when it had barely issued. How much money do you think he could have made from the patent, if he had held on to it and effectively monetized it, as the early Internet grew to have so many companies using collaborative filtering systems to sell products to users and make money?