At least according to a few internet sources, it was in initially invented as a critique with the irony intended.

Over time it became idiomatic speech for initiating something difficult

I believe it's the origin of "bootstrapping" as a verb, in which it immediately becomes unironic technical jargon.

i.e. as in getting a start-up off the ground or, when shortened further, "booting" a computer.

I think you're correct about the origins. That said, a typically ironic idiom can still give rise to non-ironic derivative words.

I don't think it's entirely non-ironic. I think the term acknowledges the inherent risk in the situation. You are attempting something statistically impossible. So many of these ventures do not pan out.

I think we are obviously quibbling, but that's okay. I think it's not about risk but the meaning is simply making something from nothing, or making much from very little.

I don't think booting my computer is inherently risky or statistically impossible

Sorry, I was referring to the term bootstrapping with regards to startup companies.

I agree that in reference to computer startup, it's just being cheeky.

You’ve never heard of a bootstrapped startup? On this site?

The term itself is not sarcastic but the concept acknowledges the inherent sarcasm of it, since the chain of programs must have an initial mover

It can and is used with both opposite meanings.

The same as how "literally" means both "literally" and "figuratively", depending on the context.

> The same as how "literally" means both "literally" and "figuratively", depending on the context.

I disagree with that analysis. It's true that "literally" is often used when the modified phrase is figurative, but that's not quite the same thing is it meaning "figuratively" - were we to remove the "literally" the utterance would not be more likely to be interpreted as literal. The role it's serving is as an intensifier, and I contend that it's a fairly ordinary example of hyperbole. In the same way, when someone says "you left me waiting for days" we don't say that sometimes days means a handful of minutes depending on context, but that sometimes people exaggerate.

(And I recognize that at least one sufficiently respected dictionary disagrees with me; I think they got it wrong.)