Technically Kim Jong-Un isn't the head of state in the DPRK, but you'd be kind of stretching it to say he didn't occupy the big seat of power. Obviously the President of the US isn't equivalent to Kim's position as the non-technically-head-of-state, but PotUS being the singular most powerful position an individual can occupy seems to be uncontroversial. In this vein wanting a President to have been homeless, worked a minimum wage job for 10 years, or drowned in student debt isn't that different than wanting them to have been a soldier or gotten a doctorate if you believe such experience is a bulwark to doing dumb or bad stuff.