I think a CEO, or at least the founders, should have leverage as soon they can afford it.
In both my start-ups, an “assistant” (office+paperwork+EA) was literally the first non-founder+engineering team I hired. Deal with office issues, help with basic functional QA, greet partners, help with travel drama, fix a marketing website, whatever it is.
It gave us a ton of leverage.
Since then, I’ve mostly done without.
I think that has been a mistake.