Hilary Fitzgerald Campbell is a cartoonist and comedian based in New York City.

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(00:00) Panic attack move from LA to New York

(03:18) Burnout at Slamdance and leaving film festival life

(06:41) First impressions of New York and stranger kindness

(10:02) Childhood dreams of cartooning and art school detours

(13:41) Choosing drawing over animation and film collaboration

(16:32) Nannying, hosting, and early Brooklyn survival jobs

(19:22) Building Cartoons by Hillary on early Instagram

(22:36) Feminist Fight Club and first freelance momentum

(25:41) Weekly New Yorker submissions and intimidating first visits

(29:07) First cartoon sale and leap into freelancing

(32:24) Cheap rent, broke artist life, and creative freedom

(35:18) Plateauing income, AI anxiety, and managing multiple projects

(38:29) The Joy of Snacking and eating disorder recovery

(42:06) MyFitnessPal, bulimia, and the quiet reality of struggle

(45:52) Lifetime movie irony and realizing there was a way out

(49:11) Art, walking New York, and healing through purpose

(53:04) Burlesque discovery, stage confidence, and body liberation

(57:01) Why the artist life has still been worth it

Ella De Leon Detlefsen is an artist based in New York City.

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(00:00) Moving to New York for finance

(01:18) Childhood drawing obsession begins

(03:02) Surreal portraits and Tim Burton influence

(04:41) Middle school art obsession takes over

(06:18) Family artists and inherited creativity

(07:37) Choosing business over art school

(09:46) Studying analytics while suppressing art

(11:26) Secret first post goes viral

(13:23) Learning commissions through improvisation

(15:08) Turning songs into visual art

(17:18) Piano, violin, and visualizing sound

(19:16) Creative control and selective commissions

(20:42) Nightly work habits and flow state

(22:28) New York pushing her toward risk

(24:26) Meeting artists through everyday city life

(26:03) Fear, stability, and pursuing art seriously

(28:04) Finding art everywhere and resisting AI

(30:19) Success, social media, and self-belief

Caia Diepenbrock is an artist, designer, and freelance art director based in Brooklyn, NY.

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(00:00) Family roots and finding New York

(03:08) Rhode Island, Bard, and early city overwhelm

(06:11) Seven years in LA, then Brooklyn home

(08:54) Why New York felt more alive

(11:02) From psych to studio art at Bard

(13:41) Growing up with two working artist parents

(16:52) Drawing, painting, printmaking, and immersive worlds

(19:18) Discovering art therapy in high school

(22:41) Art therapy for adults and creative mindfulness

(26:07) Bard’s experimental art culture and RISD contrast

(29:14) Post-college paralysis and accidental film entry

(33:02) Restoration Hardware to HBO art department

(36:06) What installation art actually is

(38:37) New York freelance life after leaving LA

(42:12) Film industry highs, lows, and toxic thrill

(46:03) Networking, reliability, and making luck easier

(49:28) Art directing strengths and hidden-gem art spaces

(53:06) Freelancing, side hustles, and defining success

Chloé Simone is a writer, a spiritual coach, and a DJ based in New York City.

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(00:00) NYC move via Wall Street Journal job

(02:10) New York dreams and Great Migration lineage

(04:35) Loving literature; discovering writing talent

(06:40) Teen screenplays and filmmaker ambitions

(08:40) NOCCA arts high school film program

(11:10) “Witchy” New Orleans and strict Christian home

(14:40) Outsider identity, shellfish ban, protecting five girls

(17:35) Katrina evacuation, Alexandria year, return home

(21:45) College pivot: film to international studies

(24:15) Bret Stephens mentorship and WSJ application

(27:55) WSJ newsroom life and first published op-ed

(31:10) Realizing newsroom choreography isn’t for her

(33:10) Israel-Palestine thesis and three Enchantment principles

(36:20) Going solo: course creation, cold emails, podcasts

(39:05) First big client; 2020 BLM-driven boom

(41:55) Critiquing Kendi/DiAngelo; Baldwin and human depth

(44:35) 2025 downturn, social media exit, Substack shift

(46:50) Coming out, disowning, artist life, success vision

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

Nick Marsella is a Juilliard alum and a composer, based in New York City.

Instagram and all episodes

(00:00) Unorthodox plan to move to New York

(03:21) Cold texts, a stranger says “call John”

(06:04) John offers help—move “right now”

(08:58) Staten Island basement room: rough, cash, roommates

(12:07) Long commute: bus, ferry, train to Times Square

(15:14) Mice, sleeping on the floor, retail hustle

(18:02) Juilliard bookstore dream and immersion in repertoire

(20:41) Two goals revealed: Juilliard and homeless orchestra

(22:33) Early music roots: church, dad as worship leader

(25:47) Discovering orchestral music and “alien language” fascination

(29:18) Switching to composition, building curriculum from scratch

(32:36) Conviction, clarity, and going all-in on a calling

(36:08) Doubts up close, perseverance from decision to decision

(38:52) Friends doubting him; rooftop celebration and first drink

(41:35) First Juilliard rejection and the two-application rule

(44:17) Four years in the bookstore: night classes and mentors

(48:09) The acceptance letter—East Village tears and relief

(51:26) Pandemic shutdown and persistent imposter syndrome

(54:44) Goal two evolves: grant, videos, and “Us Us” piece

(59:37) Corporate detour, layoffs, and recommitting to the mission

(63:08) Carnegie Hall vision and first violin for Michaela

(66:34) Fundraiser “The First One,” Bowery Mission partnership

(69:41) Defining success: serving others, dignity through music