I have a few friends who have cashed out through various acquisitions. In every case it made them a "thousandaire". But they were ICs/engineers, not founding management.
Any chance you could elaborate on this? What about stock grants were you unaware of (or misunderstood) until it was too late? What should people reading this watch out for?
I’m not the parent, but it’s really hard to pull a future-proof contract about stock grants. The most frequent shenanigan is probably to dillute the employee shares. Even if you are the CEO, investors can get you fired-in-bad-terms just to cancel out your shares.
Some contracts require 66% or 75% of votes to be able to change the repartition of shares or extend capital, or even any shareholder can veto. Some contracts don’t have conditions.
Philosophically, even if not written in the contract, someone could convince you to dilute at the last minute. The best interest of a buyer is to put the target in close bankruptcy before buying it. Anything is possible in peer-to-peer negotiations, and legal framework can only go so far.
That can't be evaluated without full knowledge of the contract and a lot of knowledge of the personalities involved. There is no 'safety' in dealing with other people, you need to know whom to trust.
they gave a fraction of a fraction of a percent, from a particular share class that likely was subordinate to other liquidity preferences.
like, even if you were personally more informed the outcome wouldn't be different? you would have rooted for an even bigger upside for the whole company.