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

Mike Perry is a painter and graphic designer, based in Brooklyn, NY and Athens, NY.

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(00:00) Following love to New York

(02:43) Early hustle and instant momentum

(05:34) Dental floss letters and studio realization

(07:58) Pre-social era: reputation and “Hand Job”

(10:41) Independence, Missouri and a creative family

(13:28) Drawing obsession and being “terrible” in school

(15:52) Dyslexia: letters as shapes, school misunderstandings

(18:41) Neurodivergence as strength and problem-solving

(21:07) Art as purpose: reaching your tiny percentage

(23:46) Minneapolis art school and pivot to design

(26:18) Graphic design philosophy: problems, solutions, process

(28:57) Urban Outfitters: mentors, mecca, behind-the-curtain lessons

(31:37) Handmade aesthetic and early website experimentation

(34:09) Design blogs, relationships, and building a contact list

(37:02) Creative control, big collaborations, and trusting teams

(40:12) Advice now: uncertainty, AI, and human connection

(43:06) Pushing into hard projects and long-haul persistence

(46:12) Success = control of time, boredom, and freedom

Shaun Murphy is a stand-up comedian, based in New York City.

Instagram and all episodes

(00:00) Early NYC attempts and returning for good

(02:11) Not a class clown, surprising comedy origins

(04:05) Discovering stand-up through Comedy Central era

(06:18) First stand-up class and graduation show experience

(09:07) Early Buffalo comedy scene and first performances

(11:52) Mitch Hedberg’s influence and comedy inspirations

(14:36) Bombing, laugh tracks, and audience unpredictability

(17:41) Why crowds vary night to night

(20:12) Finding identity and accepting audience reactions

(22:47) Realizing comedy could become a lifelong pursuit

(25:31) Leaving NYC, regrouping in Buffalo, building skills

(28:09) Saving money and preparing for NYC return

(30:46) Stability, roommates, and moving to Astoria

(33:18) Grinding early NYC years and side jobs

(36:22) Getting passed at the Comedy Cellar

(39:41) Learning from legends like Chris Rock and Attell

(43:28) Career stability, income streams, and comedy business

(46:12) Defining success and favorite stand-up venues