If I could map out an ideal trajectory for a comedian’s career, I would say they should start in New York, where there are endless places to do stand-up, especially where there aren’t creepy industry folks lurking around.
They can hone their craft in obscurity, bombing without having to worry about who might see them. Once they’re ready, they can move to LA, complain about how bad the stand-up scene is compared to New York, but enter the casting world and be introduced to other club managers as a well-groomed, finely tuned comedian.
While starting in NYC has its pros and cons, I'd say the best path is to get stagetime in a smaller town (Boston, Chicago, or SF for example) first. Good luck getting 30 minute sets in NYC, ya know? Plus, you get to develop under the radar in other places. Here, people judge you and make up their minds. Once that call is made, it can take a long time to turn it around. Then again, this guy's name is Reg Tigerman which is a pretty great name so maybe just listen to him.