I have never heard that expression used unironically. I feel like the idea that there are people out there saying it in earnest is itself a meme that was never true.
i.e. as in getting a start-up off the ground or, when shortened further, "booting" a computer.
I don't think booting my computer is inherently risky or statistically impossible
I agree that in reference to computer startup, it's just being cheeky.
Over time it became idiomatic speech for initiating something difficult
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.)