I'll refrain from commenting about what a ceo may or may not know about insurance.  Suffice it to say almost no one has long-term care insurance -- practically no nursing home coverage -- and a chronic illness, or series of illnesses, can easily drain the coffers over a course of years.

As your ceo may even be aware, there are myriad types of insurance coverage with various co-pays, deductibles, exculsions, prescription pay scales, catastrophic caps, lifetime care caps, you name it -- there's a ton of ways to suck someone dry.  In fact, what used to be some of the better insurance plans were the ones with 80/20 coverage -- they'd pay 80% and you were 20% out of pocket -- nowadays 20% of even one hospitalization can be disasterous (although probably not to a millionaire, admittedly), nevermind a decade or so of care.

Maybe we can eventually make language a complete impediment to understanding. -Hobbes