Quoted from DBLM:
Storytime: I worked for a unicorn that IPO'd. I was given X amount of shares, and a week before the IPO, they did a reverse split to get the share price to where they wanted to be for the IPO. During the lockup period, the share price doubled, but nobody could sell anything. After lockup, we had drifted back down to somewhere just north of IPO price.
I had a similar situation in a much smaller company. We went through a merger, which required me to purchase my options and pay capital gains tax. They reverse split the stocks to bump up the price, valued it at a fictitiously high $15, put it on the penny stock market with a lockout period shorter for the executives+investors than employees.
Long story short one investor protested the merger, and got a settlement for $10/share, which in hindsight was a brilliant move. When the lockout period ended for executives+investors they were cashing out at about $7-8, and by the time employee lockout happened it was well under $1. I had so many shares, the transaction fees at the time would have eaten up most of the return, so I just held for novelty's sake. Long story short, it may not even matter how early you were (I started day 1 with 7 others), the amount of options, the strike price, or the dilution of your equity, there are still plenty of ways an investor can get shafted.