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Re:Ask HN: Anyone have stock option horror stories? by sideproject on Thursday March 17, 2022 @05:39AM (#30709276)
Joined as employee #2 of a startup. Over the years, accumulated about 1.9% of the company shares. At one stage, the company was valued at ~$300M. Several buyers approached over the years, the chairman only wanted to sell at a ridiculous near $1B. So it never got sold. Several in-fightings, layoffs and a few years later, we exited with $18M acquisition.
Re:Ask HN: Anyone have stock option horror stories? by cfontes on Thursday March 17, 2022 @06:21AM (#30709508)
Oh man, that hurts. As much as when I rejected an early position and at least 1% of a company that is now worth $1 B, because they demanded me to shut down a website I had at the time that was remotely related to their business and doing well ( I was super proud of it, we where getting some news coverage locally and even offers to sell) I would probably have joined if it was not for that demand, I think.

The most expensive thought of my life was "those fuckers will not tell me what to do".

I don't regret it, since it led me to the best part of my life after that site was eventually shut down 3 years later, but man... Sometimes late at night, alone over a drink, it comes back and bites.

Re:Ask HN: Anyone have stock option horror stories? by bluefirebrand on Thursday March 17, 2022 @10:40AM (#30711684)
I think the software industry might be a lot better to work in if we collectively thought "These fuckers will not tell me what to do" more often.
Re:Ask HN: Anyone have stock option horror stories? by moharoune on Thursday March 17, 2022 @06:47AM (#30709644)
How much money you ended up with in cash ? Is it as straightforward as $18m×0.019 = $342k ?
Re:Ask HN: Anyone have stock option horror stories? by lmm on Thursday March 17, 2022 @06:57AM (#30709699)
Not necessarily, later investors may have liquidation preferences that would reduce it, potentially even to zero.