Unless you’ve ever been truly penniless. Being bitter beats the true terror of forcing your family to live in a shelter.

That can certainly happen and it is truly scary, not arguing about that.

I think what most people here on HN mean by 'penniless' is living with their parents and having no disposable income, or some other stressful arrangement. Something that their (perhaps former) friends and acquaintances would consider an embarrassing failure.