I don't remember the details. I had bought a (modest) vehicle with exercised gains (and maybe employee stock purchase). Don't remember the residual tax impacts

I don't remember the details. I had bought a (modest) vehicle with exercised gains (and maybe employee stock purchase). Don't remember the residual tax impacts being a big factor in general--may have been timing of some sort. But a $100 stock went to about $4. Went back up a bit and then only became somewhat OK through various subsequent acquisitions and spin-offs. But, yeah, a lot of people got clobbered when they took profits and then held onto the stock--and other scenarios like you say. When I left not long before dot-bomb, I'm glad I didn't go for all the stock options they were offering me but I had already made the decision to leave. The company I went to cratered but, as I wrote, someone I knew picked me up. But, yeah, making it through dot-bomb was incredibly lucky. The situation in tech broadly may not be great today but it's not like 2001.