absolutely stupid 100%. Also, to justify him a bit, I think that the best way to expose your fiat business to bitcoin is trought custodians. If you are a business you want to pay taxes, be compliant, and so on to continue to do your fiat business; so self custody is mostly a risk.
Also, even in that case, I would use bitcoin in self custody + complete privacy for doing what bitcoin is useful for: tax evasion and hiding wealth. 
But they are two "different profiles" for different use cases.

If I would be him probably I would "act" like him (while speeching very differently, and understanding others perspectives). We know how many bitcoin microstrategy has with custodians, by definition we dont know how many bitcoin Saylor is hiding in self custody (probably 0 as he seems so retarded, but still, we dont know by design).

For myfelf, as subject that dont have a fiat business to be compliant with I dont have any doubt, I'd go 100% with privacy + self custody + tax evasion. (or 98% hide / 2% tax-reported to make my profile credible, idk).