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You’re lucky to even have done OK. Not only did a lot of people get wiped to zero, but some people ended up in huge debt to the govt. I know multiple people w

You’re lucky to even have done OK. Not only did a lot of people get wiped to zero, but some people ended up in huge debt to the govt. I know multiple people who went through: - Exercise an option and “realize a gain”. Have to pay taxes for that year on the realized gains. - stock crashes to zero or near zero before they had a chance to sell (either because of blackout periods or not being public yet) - tax burden from year N-1 is still due for hundreds of thousands. Capital loss offset only helps for returns in the following years Sell to cover if you can

ghaff 2y ago
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.
trgn 2y ago
Also the story of midcap saas going public around 2020.
- ghaff 2y ago
  Application service providers. Was just not the right time.
thijson 2y ago
I worked with some folks like that. They emphasized always do same day sale, don't sit on the stock after exercising. They had massive tax bills, because they exercised when the stock was flying high, but didn't have enough cash to pay for it. The stock itself had cratered so they couldn't raise money that way.
BeFlatXIII 2y ago
Stories like that make me wonder why domestic terrorism isn't more popular.

ghaff 2y ago

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.

trgn 2y ago

Also the story of midcap saas going public around 2020.

ghaff 2y ago
Application service providers. Was just not the right time.

thijson 2y ago

I worked with some folks like that. They emphasized always do same day sale, don't sit on the stock after exercising. They had massive tax bills, because they exercised when the stock was flying high, but didn't have enough cash to pay for it. The stock itself had cratered so they couldn't raise money that way.

BeFlatXIII 2y ago

Stories like that make me wonder why domestic terrorism isn't more popular.