Its one thing to say 'rate my startup', but to say 'look how much I'm making' is something totally different.
This way of speaking has now passed down to high school students and isn't associated with any specific sort of ideas (unless you count the empty set as a type of idea), but it was originally quite a nasty piece of conversational jiujitsu.
Imagine how a posh, and possibly a bit poncey Englishman might say "who", and you should be close to the sound of the U's in "jujutsu". The first U is elongated, and the rest are short.