rant · moment 7 of 15
The Rich Kid's Comedy Advice Request and Asking Him for Five Grand Instead
from Graveyard Shift At A Bread Warehouse · #87
Audio-only archive episode — no video to seek.
8 minTim reads through the full absurd message from a wealthy Blackstone-employed acquaintance asking how to break into comedy for his rich friend, and riffs on his plan to respond by asking to borrow $5,000, mocking how rich kids never invest in their own projects and misunderstand how show business actually works.
- 27:23Tim receives a message from a wealthy former classmate from Holy Trinity High School asking for comedy advice.
- 27:50The kid left finance to pursue comedy and is 'diving straight down' into the business.
- 28:25He wants to know how to transition from open mics to featured spots and write a pilot for a web series.
- 28:59Tim responds by asking to borrow five thousand dollars, claiming he's struggling despite appearances.
- 30:01Rich kids never invest in their own projects—they want the blueprint instead of building it themselves.
- 31:05Tim explains that traditional success models don't apply in comedy; it's a fun house where normal rules break.
- 31:42There's plenty of room for well-educated wealthy guys in comedy writing rooms, so why is he doing open mics?
- 32:08Most people who quit their jobs for creative pursuits shouldn't be doing it—only about one percent should.
- 33:13Tim respects the honesty more if someone admits their corporate job is meaningless rather than pretending art is the goal.
- 34:20This business is the Wild West; the thing that breaks you might come from something you do that feels completely insignificant.
BlackstoneSteve SchwartzmanChris GethardNorm AbramThis Old HouseThe Yankee WorkshopNetflixBob VilaBobby LopezHoly Trinity High SchoolHewlett Bay Park