It really sounds like this CEO just checked out. Sounds like the board should have stepped in and either replaced him for being an ineffective steward of the company. Which just goes to show that the CEO has fault, but there are others that were asleep at the wheel as well.
In my entire career the highest paid people in a private company (including multiple high growth B2B startups) has always been the top sales people. Not the sales manager, not the CEO, an individual contributor Sales person. As you hit more and more above quota, accelerators kick in where you commission percentage increases massively. And our CEO loves writing them those checks because good sales people way more than pay for themselves.
The boat may of been bought from the appreciation of the home.
I mean.. that's capitalism? Capital accumulation is the bedrock of the system.
a. having enough capital in the business to pay severance, or, b. firing people at the point before they stopped being able to avoid severance.
... are both better options than he should have taken.