Cale Hawkins is a songwriter and music producer based in New York City.

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(00:00) From western New York to New York City

(01:10) Discovering music, country, and the Beatles

(03:55) Taking music seriously as a kid

(05:05) Finding mentors at the Infinity Program

(07:15) Talent, improvisation, and learning from better musicians

(10:18) Why the Beatles remain the gold standard

(14:30) High school and choosing music professionally

(19:17) Knowing music was the only path

(20:29) Professionalism, listening, work ethic, and rejection

(24:35) The music industry’s unwritten rules

(26:40) Berklee, Derek Sivers, and moving faster

(31:25) Leaving Boston and starting over in New York

(35:08) Touring dreams and surviving through poker

(36:16) The Quincy Jones audition that changed everything

(38:40) Learning from the legendary Quincy Jones

(42:54) Marriage, touring, and putting down roots

(47:02) Making a long-distance marriage work

(48:09) Knowing when touring was no longer worthwhile

(50:32) Falling in love with producing music

(54:09) Making creativity financially sustainable

(59:26) Simplicity, songwriting, and unexpected passive income

(63:38) Redefining success as freedom and fulfillment

Bonnie McFarlane is a standup comedian based in New York City.

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(00:00) From Canadian poverty to creative ambition

(04:45) Choosing a cow and building a business

(07:19) Family, hard work, and money

(10:30) Discovering writing, acting, and advertising

(13:07) Finding safety in the comedy world

(17:18) Winning a contest and reaching New York

(22:01) Bombing at Caroline’s

(24:11) Surviving New York without a day job

(25:54) Falling in love with stand-up

(29:52) New York’s legendary comedy scene

(32:19) Letterman and career breakthroughs

(35:47) Meeting Anthony Bourdain through a roast

(40:00) Writing jokes for Anthony Bourdain

(42:09) Remembering Bourdain’s character and authenticity

(44:45) Why fame suddenly started mattering

(48:32) The psychological block around social media

(51:46) Why fame makes stand-up easier

(53:22) Stand-up as a spiritual journey

(55:49) How young comedians work differently

(56:56) Challenging beliefs through comedy

(60:52) Redefining success, fame, and artistic freedom

(64:14) Finding new paths to an audience

Claire Wellin is a singer-songwriter and musician based in New York City.

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(00:00) Moving to New York for Broadway

(04:50) Growing up in a musical family

(06:43) Childhood in Bismarck, North Dakota

(10:01) Violin training and musical burnout

(13:00) Discovering songwriting and Andrew Bird

(18:35) How Once changed her life

(22:55) Surviving as a working musician

(27:52) Finding time to make her own music

(29:54) The unstable state of music

(31:13) Why she never considered quitting

(34:01) Songwriting, family history, and grief

(39:12) Family stories of perseverance and forgiveness

(47:17) Redefining success as an artist

(49:49) Why music has become pay-to-play

(51:56) The rise of covert music marketing

(55:26) Music industry in a new era

(56:16) Artists making great music today

(59:19) Upcoming release show

Anthony DeVito is a comedian based in New York City.

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(00:00) From North Jersey to New York comedy

(03:18) Architecture by accidental family promise

(06:37) The old-people rental building presentation

(09:42) Discovering architecture’s beauty and limitations

(12:31) Failing forward at an Italian architecture firm

(15:08) Learning his father was a made man

(18:54) Inventing a mythical father figure

(22:06) Discovering the truth about his father’s death

(25:48) Reconciling crime, family history, and empathy

(29:36) Carlin, Chris Rock, and comedy’s honesty

(32:15) Early stunts, sketches, and stage fright

(35:42) Surviving New York while building a career

(39:12) Early success and changing ambitions

(42:18) Finding deeper truths through stand-up

(45:03) Creative routines, friendship, and staying playful

(48:11) Masculinity, the manosphere, and lost young men

(52:23) Comedians who combine truth and empathy

(54:31) Success means freedom, friendship, and love

Asher Kurtz is a guitarist and music producer based in New York City.

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(00:00) Moving to New York for music

(02:51) Discovering guitar and early musical influences

(05:48) Arts high school and falling in love with jazz

(08:56) Family support and pursuing music seriously

(11:41) Talent, competition, and finding confidence

(14:38) Choosing Berklee and college experiences

(17:57) Teachers, genres, and building a musical network

(21:16) Why music school didn't prepare him for work

(24:08) Moving to New York and surviving odd jobs

(27:41) Smorgasburg, dog walking, and early hustle

(30:49) Making the leap to full-time musician

(33:37) Australia tour and career-changing experiences

(36:31) Pandemic reset and rediscovering creativity

(40:12) Producing, engineering, and building a new career

(43:26) Teaching music and working with children

(46:18) Clint Strong's life-changing mentorship

(50:07) Encouragement versus strictness as a teacher

(53:06) Future goals and nearly leaving New York

(56:18) Loss, grief, and creative renewal

(59:08) Favorite musicians and lifelong inspirations

(62:07) Favorite New York music venues

(64:35) Defining success and closing thoughts

Myq Kaplan is a standup comedian based in New York City.

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(00:00) Moving to New York for comedy

(03:14) College, grad school, and career ambitions

(06:41) Music before stand-up comedy

(09:58) Philosophy, psychology, and linguistics

(13:21) Discovering ethics through Peter Singer

(16:47) Choosing creativity over conventional careers

(20:06) Comedy as a practical life path

(23:39) Philosophy that changes daily life

(27:18) Stoicism, Buddhism, and gratitude

(31:02) Identity, Theseus' Ship, and consciousness

(34:36) Practical wisdom for living well

(38:08) Comedy after ayahuasca

(41:19) Creating "All Killing Aside"

(44:51) Finding a new creative process

(48:07) Lessons from Rory Scovel and improvisation

(51:12) Why ayahuasca kept calling him back

(55:02) Death, fear, and the wave analogy

(59:18) Psychedelics and creative purpose

(63:01) Meaningful comedy versus silly comedy

(66:07) Eminem, rap, and artistic expression

(69:18) Making comedy funny and meaningful

(72:28) Defining success as a comedian

(75:08) Money versus fulfillment

(77:41) Gratitude and the jacuzzi analogy

(79:34) Helping others through joy

(81:02) Final reflections on success

Olga Sunden is the curator of “Through Her Eyes” and an activist based in New York City.

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(00:00) Leaving Ukraine for New York

(01:46) First impressions of New York at 28

(03:41) Government pressure and fleeing Ukraine

(06:08) Learning English and embracing America

(08:29) Ukrainian and American cultural differences

(11:02) Growing up in the Soviet Union

(14:14) Family reacts to Russia's full invasion

(16:59) Ukraine's unity and civilian resistance

(20:08) Father's medical emergency during invasion

(22:03) Creating a photo exhibition through women's eyes

(25:06) Why Putin invaded Ukraine

(28:12) Women's photographs reveal hope amid war

(30:13) Why Americans should support Ukraine

(32:11) How citizens can influence Congress

(33:38) Hope for Ukraine's future

(34:55) Raising children despite uncertainty

(35:43) Future exhibitions in Kyiv and Washington

(36:34) Promoting the book beyond the galleries

Ophira Eisenberg is a comedian and writer based in New York City.

Instagram and all episodes

(00:00) Moving from Toronto to New York

(02:44) Arriving before 9/11

(05:58) Performing after the attacks

(09:09) Building a life from nothing

(11:50) Toronto success and New York gamble

(14:18) Learning IT to survive

(16:18) Early New York comedy scene

(20:17) Discovering The Moth

(24:07) Networking through comedy

(27:46) Book deal and NPR breakthrough

(31:06) Storytelling versus stand-up

(35:07) Why New York still matters

(38:55) Returning fully to comedy

(42:00) Scars, cancer, and identity

(47:07) Childhood car accident and loss

(51:22) Resilience and rejecting platitudes

(53:52) Wellness industry and conspiracy theories

(55:58) Parenting, comedy, and vulnerability

(57:22) Staying relevant as a comic

(58:21) Defining success through respected peers

James Hamilton is a writer and comedian based in New York City.

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(00:00) Teaching fourth grade and discovering improv

(03:32) Childhood creativity and finding comedy's language

(06:41) Family expectations and meaningful work

(09:39) CJ Hunt and a lifelong creative partnership

(12:43) Creativity as communication and personal awakening

(16:09) Improv, writing, and choosing New York

(19:38) Leaving New Orleans without a real plan

(22:54) Early survival jobs and TV writing packets

(26:37) Learning to write in other people's voices

(30:14) Landing the dream job at Vice News

(33:42) Favorite stories from Vice reporting

(37:08) Vice's collapse and media's changing landscape

(40:36) Freelancing, documentaries, and Olympic writing

(44:06) Money, creative freedom, and the Posters podcast

(47:31) Dikembe Mutombo's remarkable basketball legacy

(51:01) Building a writing career through persistence

(55:08) Collecting rejections instead of fearing them

(58:14) Favorite New York storytelling venues

(60:19) Defining success through deeply personal work

(62:07) Creating uniquely human art in the AI era

Dan Davies is a standup comedian based in New York City.

Instagram and all episodes

(00:00) Childhood trips spark New York dream

(02:08) Discovering UCB and falling for improv

(04:37) First improv class and early confidence

(06:53) Long-form improv and the Herald

(08:52) Balancing hospital work and comedy

(11:08) Quitting a stable career for comedy

(13:36) Day jobs while chasing stand-up

(15:39) Building Question Party into a business

(17:42) Early success through audience laughs

(19:44) First stand-up set and catching the bug

(22:02) Avoiding open mics and finding stage time

(24:24) Learning by performing with better comics

(26:42) Getting passed at the Comedy Cellar

(31:02) Auditioning for the Comedy Cellar

(33:32) Writing jokes and comedy influences

(35:42) Why New York is comedy's capital

(37:30) Defining success as a working comic

(39:02) Why chasing comedy was worth the risk