[TOMT][Video][2010s] A short documentary about a wannabe rapper and how his failures relate to toxic positivity and hustle culture.

I've recently gotten back into longer form, youtube minidocumentaries. My favorites are from seemingly random people that combine seemingly unrelated ideas. The video in question i'm looking for is about a guy who embodies everything about modern "hustle culture".

Imagine a person who is an unremarkable, normal person, but takes every self help guru seriously so he believes he's destined for greatness and goes millions of dollars in debt trying to "break out".

I found this video sometime in the 2010s. The guy was white from what I remember, and his name was a very simple one syllable name preceded by "uncle", something like "uncle steve" or "uncle ben". He started off trying to copy his heros and make a living selling self help books, when that didn't work he started trying to do "clean rap" about things like working hard and being motivated. throughout the video the creator keeps track of uncle jons random, arbitrary goals like "get rich", and comparing them to his budgeting videos where he gets increasingly deeper in debt with each failed venture.