> The original owners could have put in a voluntary, irrevocable, liquidated damages clause that is sufficiently punitive that no subsequent owner of the company would think to violate it
If a court believed the liquidated damages were punitive, they would reject the value specified by the contract and substitute a more reasonable estimate of the actual damages.
I am aware such a result is possible, but as far as I am aware (I am not a lawyer) punitive liquidated damages being substituted occurs due to a general legal theory of unconscionability that such terms are imposed against a weaker party and are sufficiently unfair.
That is not the case here as this is the clearly strong party, being the entity drafting the contract of adhesion, uniformly adding it to contracts where they have complete control over the terms where it harms themselves for the benefit of the weaker party. I find it highly unlikely that a clause with such facts would be struck down in existing precedent or in the future, though I could be wrong. If I am wrong, then I need to come up with a new idea.
If a court believed the liquidated damages were punitive, they would reject the value specified by the contract and substitute a more reasonable estimate of the actual damages.