Jessica Earnshaw is a documentary filmmaker and photographer, based in Brooklyn, NY.

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(00:00) Moving to NYC for ICP

(02:08) Growing up with a photographer mom

(04:01) Why photojournalism felt empowering

(06:18) Grant: documenting aging in prison

(08:07) Meeting Rosemary and Jacenta

(10:11) Realizing it needed to be film

(12:03) How they landed in prison together

(13:53) Addiction, trauma, and “chasing mom”

(16:02) Getting permission and prison access

(18:14) Filming 2016–2019 with no funding

(20:54) Living broke: motels, burritos, gas

(22:47) Leaving a tour when filming demanded it

(24:46) Men’s prison: long days, earned trust

(27:12) Trauma shaping violence and crime

(30:05) Research: reoffense, parole, and “snapping”

(33:06) Hospice program and Albert’s story

(34:52) Baby Doe: toilet births and denial

(38:16) Gail’s case: DNA genealogy, trial, empathy

Eviatar Slivnik is a jazz drummer and composer, based in Brooklyn, NY.

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(00:00) Moving to New York to test yourself

(04:21) Early heroes and jazz influences

(08:37) Falling in love with jazz’s mind and soul

(12:54) Jazz as high-level conversation, not noise

(16:49) Why expertise matters before improvising

(20:58) Childhood development: bands, drive, priorities

(25:26) Arts high school in Tel Aviv and practicing

(29:44) Rejection from workshop sparks daily discipline

(34:10) Two-hour routine: humiliation, habits, results

(38:33) Dreaming bigger at Berklee and in NYC

(42:57) Jazz history: hardship, resilience, origins

(47:22) Paradoxes: street music, complex art form

(51:41) NYC grind: clubs, jams, community, reputation

(56:06) Stops and restarts: Berlin, COVID, returning

(60:34) Philosophy: practice, depth, ego, “good hang”

(64:41) Breakthrough call: touring with Avishai Cohen

(67:08) Touring reality: stress, logistics, reward

(71:19) Money, saving, and success as staying in game

(74:36) Compound interest mindset: practice, character, longevity

Lindsey Ferrentino is a playwright, based in Brooklyn, NY.

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(00:00) Moving to NYU at 17

(02:18) Realizing acting isn’t the path

(04:35) Family of comedians, early writing habits

(07:20) Teaching herself screenwriting in Florida

(10:05) Copycatting influences before finding a voice

(13:12) Strasberg training reframed as writer training

(16:05) Grad school focus: Hunter MFA, then Yale

(18:55) Theater vs film/TV: money, control, reality

(22:10) Romantic New York “life in the arts” idea

(25:40) Teacher pushes Florida settings; authenticity clicks

(28:55) “Big break” mindset: relentless readings, submissions

(32:05) Off-Broadway launch: “Ugly Lies the Bone”

(35:10) Play premise: burn survivor, VR therapy, reintegration

(38:25) Lessons from productions: scale, staging, dialogue

(41:45) Post-break output: adaptations, multiple shows, pace

(44:12) Writing routine: sculpting in small blocks

(47:08) Current obsessions: Nick Yarris, justice system story

(50:36) Queen of Versailles musical: rights, satire, success definition

(52:18) Gratitude, “lucky life,” closing thanks

Gillian Morris is a technologist, Substacker, and author, based in New York City.

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(00:00) Born in NYC, Immigrant Roots and Family Story

(02:45) Paris Bell Tower Life, Dumpster Diving, and Soup Kitchens

(05:20) Letting Go of the Opera Dream and Becoming a Patron of the Arts

(08:10) Regression to the Mean: Choosing Government as the Path of Least Resistance

(10:40) Solo Travel at 18 and Wonderfully Chill Parents

(13:30) Curiosity About Other Cultures and Searching for True Passion

(16:05) Many Models of Success and the Idea of Inner Vitality

(19:00) Learning to Code and Discovering Travel Tech as Ikigai

(22:10) Building Hit List and Hacking Cheap Flights for Friends

(25:40) Watching Users Join and a Life Thesis About Travel and Human Connection

(29:15) Pandemic Collapse, 95% Revenue Drop, and Mother’s Cancer Diagnosis

(32:30) Caregiving, Clubhouse, and the First Communal Living Essay

(36:05) From Side Blog to Supernuclear and a Growing Communal Living Movement

(39:30) What Communal Living Really Is and Why Commercial Co-Living Misses the Point

(43:10) Vetting Housemates, Moving Lightly, and Not Being Owned by Your Stuff

(46:20) Communal Living, American Isolation, and the Male Loneliness Problem

(50:10) Tribes, Villages, and Having Many “Significant Others”

(53:40) First Steps: Brunches, Neighbor Experiments, and Rebellious Community-Building

Harold Rogers is a novelist, Substacker, and a comedian based in New York City.

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(00:00) Columbia MFA, standup dreams & moving to New York

(03:07) Growing up between Ohio, Brazil & Antigua as a lonely reader

(04:48) Discovering serious novels: Lolita, Crime and Punishment & the power of language

(07:36) Early stories, autobiographical fiction & realizing writing can hurt people

(11:58) Drunk, depressed college years & writing through the abyss

(13:49) Tropicalia: family in Rio, plot, and learning to write a first novel

(16:33) Humility, simplifying the work & 20-day draft marathons

(22:06) Flow, exhaustion & psychography—writing as a kind of mediumship

(25:06) Boxing vs standup: high-stakes performance and the “fight vs book” metaphor

(26:47) First novel flops, expectations, airports & diversity boosts

(32:53) Publishing economics: advances, royalties & the lottery-ticket model

(36:03) Substack as practice ground, Edinburgh trip & building an audience

(38:47) Writing in New York, literary readings, misanthropy & starting BLAST

(41:46) Entering the NYC standup scene, Eric’s role & comedy friendships

(46:54) Boxing gym life, clients, CTE worries & why people fight

(54:02) Steubenville’s ghosts, shuttered mills & the 2012 assault case behind Humpty Dumpty

(54:54) Humpty Dumpty as masculine failure, regicide joke & mythic Trojan horse

(57:49) Redefining success: getting better at books & standup, and protecting time

Caleb Spaulding is a drummer based in Brooklyn, NY.

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(00:00) Driving a 2004 Trailblazer to Williamsburg with the college band

(03:12) Prog-rock frat house: how the band formed and took over campus

(06:05) Older bandmates, Jersey staging ground & choosing New York as the dream

(09:02) Beginner’s mindset, Williamsburg boom & early social media band hype

(12:10) Singing before talking: family piano nights and a childhood built on music

(15:18) Political science major, miserable law firm internship & feeling trapped on the “normal” path

(19:08) Forklift summer: warehouse monotony, hourly work and craving real purpose

(22:45) Cardboard prison, secret lyric notebooks & discovering an allergy to monotony

(26:03) Sixth-grade band class, discovering drums & Colonial Williamsburg Fife and Drum Corps

(29:40) From rock stages to dance floors: first night hand-drumming with a DJ in Brooklyn

(32:55) World percussion deep dive & finding “Drumming at the Edge of Magic”

(36:22) The Ghana leap: Indiegogo, surrender experiment & flying in with no schedule

(40:05) Open-hearted Ghana: yes-and culture, communal groove & rhythm as everyday life

(43:18) Why Ghana: djembe roots, dense drumming traditions & choosing Accra as the gateway

(46:07) Kids, funerals, weddings & how Western culture shames adults out of musical play

(49:15) Everyone has rhythm: biology, entrainment & giving “no rhythm” adults permission

(52:08) Fela Kuti, Afrobeat, 90s hip-hop flows & the bands that keep him moving

(54:47) Rhythm of Happiness now: drum-powered breathwork, rhythm consulting & the next chapter

Mariel Bildsten is a trombonist based in Brooklyn, NY.

Instagram and all episodes

(00:00) Childhood Visits and Dreaming of New York

(04:18) Grandparents, Ridgewood Roots, and an East Berlin Escape

(08:27) California Childhood and Hating Piano Lessons

(12:45) Joining School Band and Accidentally Choosing Trombone

(16:32) First Trombone Hero and the “Blueprint” Moment

(20:58) Moving at 18 and Falling in Love with New York Jazz

(25:21) Jazz as Black Music and the Harlem Renaissance

(29:49) New Orleans Brass vs Contemporary New York Jazz

(34:05) Betting on New York and Welcoming the Ass-Kicking

(38:02) Inside the Physical Demands of Playing Trombone

(41:37) Injuries, Posture Fixes, and Damage Control

(45:03) Dizzy’s Jam Sessions, All-Night Hangs, and Music as Service

(49:11) Teaching in the Bronx and $10 Pasta Gigs

(52:44) Balls Before Ability and Working Through Imposter Syndrome

(55:36) Side Person vs Bandleader and Making a Living

(58:22) Why She Still Chooses New York

(61:09) Favorite NYC Food, Clubs, and Trombone Mount Rushmore

(63:18) Redefining Success, Education, and the Next Chapter

Jamie Pearl is a photographer based in Brooklyn, NY.

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(00:00) From Seattle To New York

(04:10) Instagram Dreams Of The NY Art Scene

(07:30) Knowing She Was An Artist First

(11:20) Finding Her Medium In The Darkroom

(15:40) From Hobbyist To Neighborhood Photographer

(20:30) Graduating Into COVID And Planning The Move

(25:10) Learning Photography Through Film Basics

(29:30) Auto Mode, iPhones And The 80/20 Of Craft

(33:20) Landing In New York With No Safety Net

(37:40) Babysitting, Job Rejections And The Juve Lifeline

(42:10) First Big By-Lines: Times, Journal And Hoka

(45:50) Saying Yes To Everything And Becoming “The Photographer”

(48:20) Fashion Week Frenzy And Celebrity Shoots

(51:30) Prestige Work That Finally Opens Big Doors

(53:50) Learning The Art Of Negotiating Day Rates

(56:10) Stepping Into The Role Of Lead Photographer

(58:10) Staying Hungry And Raising The Creative Bar

(59:45) Real Talk On Networking And Defining Success