Jen Toth is an illustrator and model based in Brooklyn, NY.

Instagram and all episodes

(00:00) Scouted at Ohio State, then straight to Europe

(01:47) Sheltered Ohio upbringing to unimaginable New York life

(03:36) Chaos of model housing and competing castings

(05:41) Italy as friendship, travel, and self-discovery

(07:52) Landing in New York with agency support

(09:18) Choosing steady income over chasing fame

(11:34) Long-term clients and building a durable career

(13:26) Saving early and treating modeling as temporary

(15:07) Working between New York and Asian markets

(17:02) Best-paying jobs, global usage, and campaign money

(18:41) FIT, startup internship, and return to modeling

(20:56) Modeling myths, Project Runway, and job realities

(23:11) Fashion week calendar, market, and the Met Gala

(25:46) Why New York became home for good

(28:04) COVID pivot to illustration and first brand collabs

(31:47) Studio practice, commissions, habits, and success now

Sean Patton is a stand-up comedian based in New York City.

Instagram and all episodes

(00:00) Growing up in New Orleans and starting stand-up

(03:18) Why comedians should skip stand-up classes

(06:47) His first open mic at Amberjack’s

(11:02) Stage fright, mic technique, and bad comedy books

(14:36) Discovering comedy through Sarah Silverman and Mr. Show

(18:41) Perspective over punchlines and embracing human flaws

(23:07) Deciding to leave New Orleans after Mardi Gras

(26:41) Katrina, moving to LA, and early comedy lessons

(31:02) Why New York pulled him away from LA

(34:28) Arriving in Bushwick with $1,088

(38:11) New York’s brutal first months and rougher scene

(41:06) The Fort Greene day that changed everything

(45:03) Why artists shouldn’t try pleasing every audience

(48:34) Let the work define you, not labels

(52:07) Fame culture, social media, and hollow ambition

(55:18) Advice for comedians: believe in yourself

(58:21) Why staying in comedy is the real achievement

(61:06) Dave Attell, artistic integrity, and closing thoughts

Shawn Bullen is an artist, muralist, and curator, based in Manhattan.

Instagram and all episodes

(00:00) Wild first road trip to New York

(03:12) 2016 birthday trip becomes a permanent move

(06:18) Why New York always felt inevitable

(09:41) Childhood art influences and becoming “the art kid”

(13:02) Drawing, photography, and early graffiti obsession

(16:47) High school art success and museum recognition

(20:14) Graffiti community, adrenaline, and rooftop risks

(24:03) Teaching literacy and discovering mural leadership

(28:11) Confidence, dedication, and sibling artistic rivalry

(31:36) Arrest, graffiti cleanup, and first paid truck mural

(35:28) Dropping out, IDC Art House, and Canada art school

(39:22) Learning oil painting and refining artistic vision

(43:31) Leaving Halifax with dreams of global murals

(47:18) DIY East Coast adventure to Art Basel

(51:44) Miami highs, Occupy lows, and chasing momentum

(57:18) Advice on money, work, and making art anyway

(60:41) New York struggles, studio solitude, and creative purpose

(63:21) Defining artistic success and keeping the flame alive

Tucker Eason is an oil painter, based in Brooklyn, NY.

Instagram and all episodes

(00:00) From Oakland slumlord setup to New York leap

(03:21) Empty apartment, artist assistant, and Red Hook grind

(06:14) New York’s kindness versus West Coast nice

(08:37) Childhood art obsession and graphite miles

(11:52) Work ethic, fear, and self-accountability in the studio

(14:28) Leaving realism and discovering abstract playfulness

(18:46) Starting over in New York with Art Lab

(22:07) Art fairs, booth strategy, and selling authentically

(26:11) Live drawing, spectacle, and removing sales pressure

(28:47) Feast or famine economics of an art career

(33:02) Why passion keeps artists going through dry spells

(35:36) Why New York still matters creatively

(39:04) The barn-studio fantasy and staying culturally plugged in

(42:11) Artist flakiness, ADHD, and hating admin work

(46:18) Studio magic, experimentation, and protecting creative time

(49:27) Talent versus hunger and brutal self-honesty

(53:06) Professors, early sales, and believing it was possible

(56:01) Success, cultural significance, and living off the work

Christina Sajous is an actor, director, and teacher, based in New York City.

Instagram and all episodes

(00:00) Born in New York City

(02:11) Grandmother’s move from North Carolina

(04:46) Little Shop of Horrors obsession

(08:18) Law, mock trial, and choosing NYU

(11:54) LaGuardia High School and Playwrights Horizons

(15:47) NYU’s cost, competition, and self-belief

(19:34) Graduating early and Rent tour

(23:02) Shakespeare dreams and musical theater path

(26:11) Broadway debut in American Idiot

(30:08) Agents, workshops, and Green Day

(33:51) Broadway belonging and identity

(37:18) Discipline, training, and artistic professionalism

(42:06) Stephen Curry, Michael Jordan, and mindset

(45:02) Range, directing, and varied roles

(48:31) Leaving for LA, then returning

(52:41) Surviving New York as a working artist

(56:27) Excellence, humility, and service to art

(59:24) Redefining success and feeding Romeo

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

Instagram and all episodes

(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.

Instagram and all episodes

(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.

Instagram and all episodes

(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