Many years ago, just prior to the dot-com era, a friend convinced me to join his startup and run engineering. It was a 50% cut in pay, but it was promised the pay would go up with time, and I’d also be compensated with a significant amount of stock.
Well, the pay did briefly go up, beforfe dropping back down below the starting salary — I had to leave.
The worst part, though, was that I had over 50,000 shares vested. Within 30 days, the company was acquired, and my friend walked away with over $1,000,000. When I attempted to exercise the shares I was denied — and my friend was part of the inside group denying me the right to exercise (An admin who liked me sent me copies of the correspondence around that.) .
Suffice it to say, I ended up not making any money on the stock, and that friendship is no longer.