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I agree with all that. Dot-bomb was a nuclear winter like nothing tech has seen since--certainly including today. I was lucky enough to almost immediately land

by ghaff 2y ago

I agree with all that. Dot-bomb was a nuclear winter like nothing tech has seen since--certainly including today. I was lucky enough to almost immediately land something through someone I knew and, if it didn't pay a lot of money, it was a decent (and mostly enjoyable) living for a number of years. But a lot of people I knew basically dropped out of tech and some probably never again had solid jobs. And, yes, it also crashed any tech-heavy investments that took years to recover to their peak levels assuming they recovered at all. A stock I owned through options at one former employer were a source of tax write-offs for years. Probably led me to be a bit too conservative with such things. Eventually they got acquired through various complicated transactions and I did "OK" after something like 15 years.

kortilla 2y ago
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.
jackcosgrove 2y ago
> Probably led me to be a bit too conservative with such things Those who graduate into recessions have crimped lifetime earnings compared to those who graduate into expansions. I wonder to what extent it's lost income, and to what extent it's a more risk-averse attitude.
- ghaff 2y ago
  I don't know. For me, it was mostly don't double down on my own company stock or maybe even (at the time) more aggressive funds generally. It's not like I retreated into Treasuries. But I still did OK from the more aggressive investments because (maybe luckily?) they did pretty well. I didn't really graduate into a recession but I felt I learnt some lessons in dot-bomb (when I was probably almost 40) which was a decent way into my professional career. It was a period from the 80s when new grads in tech weren't earning anything like the incomes that at least some Silicon Valley copanies were paying if that was there thing.
- lnrd 2y ago
  > Those who graduate into recessions have crimped lifetime earnings compared to those who graduate into expansions. It's about not having access to opportunities. Something that comes to mind as an example: I would argue that the whole F.I.R.E. movement was possible only for a very specific subset of people that started working in tech in very few regions of the world between 2005/2010. That's a 5 years window to get in, maybe a bit more but that's it. Then the cost of living started booming, stock prices started booming, stock options and other kind of equity grants would never appreciate as before. People that attempt it now as a form of financial discipline have nothing to do with the people that invented it and retired as millionaires before reaching 30 by being a bit frugal and investing everything in the nasdaq. I recently stumbled upon the linkedin profile of someone that worked from Apple 2008/2014 and then was able to retire thanks to a mix of stock options and early investments in tech. He was surely savvy about it, but the conditions to be even able to do that seems astronomically low in the grand scheme of things. Just being born in another country or a couple of years later would make it impossible.
  - ghaff 2y ago

by ghaff 2y ago

kortilla 2y ago

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.

jackcosgrove 2y ago

> Probably led me to be a bit too conservative with such things Those who graduate into recessions have crimped lifetime earnings compared to those who graduate into expansions. I wonder to what extent it's lost income, and to what extent it's a more risk-averse attitude.

ghaff 2y ago
I don't know. For me, it was mostly don't double down on my own company stock or maybe even (at the time) more aggressive funds generally. It's not like I retreated into Treasuries. But I still did OK from the more aggressive investments because (maybe luckily?) they did pretty well. I didn't really graduate into a recession but I felt I learnt some lessons in dot-bomb (when I was probably almost 40) which was a decent way into my professional career. It was a period from the 80s when new grads in tech weren't earning anything like the incomes that at least some Silicon Valley copanies were paying if that was there thing.
lnrd 2y ago
> Those who graduate into recessions have crimped lifetime earnings compared to those who graduate into expansions. It's about not having access to opportunities. Something that comes to mind as an example: I would argue that the whole F.I.R.E. movement was possible only for a very specific subset of people that started working in tech in very few regions of the world between 2005/2010. That's a 5 years window to get in, maybe a bit more but that's it. Then the cost of living started booming, stock prices started booming, stock options and other kind of equity grants would never appreciate as before. People that attempt it now as a form of financial discipline have nothing to do with the people that invented it and retired as millionaires before reaching 30 by being a bit frugal and investing everything in the nasdaq. I recently stumbled upon the linkedin profile of someone that worked from Apple 2008/2014 and then was able to retire thanks to a mix of stock options and early investments in tech. He was surely savvy about it, but the conditions to be even able to do that seems astronomically low in the grand scheme of things. Just being born in another country or a couple of years later would make it impossible.
- ghaff 2y ago