I was there in 2004, back then it was still a pretty special place.

I remember WebMD was one of the most chaotic places I worked at. It was 2000-2001 and there was a president Marv Rich and a CEO Marty Wygod. They were both building duplicate ERP systems that basically did the same thing. One day, my boss Al was in a meeting, and they told him that he needed us to move the data center to the East Coast. The most valuable part was a bunch of big EMC Symmetrix arrays with all their data. He was freaking out because he got into an argument about loading all of them into one airplane, and he didn’t want to do it. He was telling them that if the airplane goes down, all of WebMD would be gone, and it needed to be loaded onto two airplanes. I don’t know why, but for some reason, that story always reminded me of my time at WebMD.

Kai’s Power Tools in 1992 . The interface was so next level it felt out of place and the more you used it features would get unlocked and more advanced. https://winworldpc.com/product/kais-power-tools/20

I always felt that Evernote was a confusing mess line OneNote I would try to use it every couple years thinking it would different only to give up a little later and go back to Notepad++