Episode 89: Jeremy Pinsly - From Grind to Greenpoint Comedy Club

Jeremy Pinsly is a stand-up comedian and the owner of the new Greenpoint Comedy Club in Brooklyn, NY.

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(00:00) Nashville to Dallas, corporate path, “this isn’t it” moment

(03:08) Choosing stand-up, moving to NYC, lining up a bar job

(05:55) Brother Jimmy’s bait-and-switch, becoming a bouncer instead

(08:20) First New York Comedy Club bringer show, early “crush”

(11:10) Six months of bringers, writing new sets every two weeks

(13:55) Audition night rug-pull, anger, deciding to break the cycle

(16:40) Finding the real comedy community, meeting comics and producers

(19:05) Starting an Upper West Side show, learning booking and hosting

(24:45) Brother Jimmy’s downstairs era, building momentum and credibility

(28:05) Bringing the show to the “new” NY Comedy Club on 24th

(31:20) Dropping the show, betting on himself, booking a headlining tour

(34:55) Getting a manager, launching “The Young and the Weary”

(38:10) Dev’s impact, therapy, COVID pivots, synagogue special, pilots

(41:15) Meeting Kayla, apartment shows grow monthly into a phenomenon

(44:05) Brownstone run, then Nashville experiments, Eastville deal lessons

(46:55) Greenpoint space discovery, terrifying negotiation, “jumping” anyway

(49:10) Building the club: green room, recording, bar program, hospitality

(51:40) Redefining success, survival metrics, respect, and opening timeline