It's kind of disingenuous to try to make this same comparison across different people.

What if you borrow money from family in order to start your business? Are you no longer "bootstrapping"?

What is Bezos decides he's bored, and wants to start something new. Really looking forward to seeing the "most successful bootstrapper of 2030" be Jeff Bezos with his self-funded $5B "startup".

Bootstrapping is not a statement about difficulty, bootstrapping is a statement about where the money comes from. That's it.

I mean I understand the concepts you’re talking about, but maybe you need other terminology? Bootstrapping doesn’t make as much etymological sense if it also covers ”got some outside funding, but not too much”.