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22. I Want to Write Like a Pop Star with Tembe Denton-Hurst and Brendon Holder
01:09:48||Season 1, Ep. 22What does it take to make it as a writer today? This week, Ira is joined by writers Tembe Denton-Hurst and Brendon Holder to talk about the rise of Substack, finding your creative voice, and navigating the changing world of publishing. Plus, they get into the books that shaped them, the brilliance of Toni Morrison, and the complexities of criticizing Black art.00:00 — Intro: Is Substack the Future of Publishing?04:07 — Meet Tembe Denton-Hurst & Brendon Holder06:23 — How Brendon Holder Built a Community With The Loosey Newsletter08:00 — Can You Actually Make Money on Substack?10:46 — What It's Like Working at New York Magazine's The Strategist11:22 — Is Substack Changing the Publishing Industry?13:53 — Should Writers Skip Traditional Publishing and Go Straight to Substack?18:37 — Do You Really Need a Book Deal to Be a Successful Writer?20:26 — The Books That Changed Tembe & Brendon’s Lives22:30 — Why Toni Morrison's Sula Is So Special27:16 — Toni Morrison, Black Literature & the Books That Stay With Us30:24 — Marlon James and the Magic of Jamaican Storytelling39:40 — What Makes a Great Book Critic?45:47 — How Writers Know What's About to Become the Next Big Thing56:00 — The Best Independent Bookstores to Get Lost In1:03:38 — Where Tembe & Brendon Love to Eat in NYC
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21. Hollywood Only Wants One Black Show at a Time with Chris Murphy and Ian Olympio
01:24:34||Season 1, Ep. 21This week, Ira sits down with Vanity Fair staff writer Chris Murphy and TV writer Ian Olympio to ask why Hollywood suddenly feels like an opp against Black people. They unpack the post-peak-TV contraction, the endless pipeline of “new white geniuses,” the rise of micro-dramas, the swirl industrial complex, and why Black characters on white shows so rarely get an inner life of their own. Plus: Tyler Perry, the A24 Blacks, and the one thing a Black TV character would never do — put a suitcase on the bed.
20. Who Gets to Be Published? with Editor Jackson Howard
01:12:05||Season 1, Ep. 20This week, Ira is joined by Jackson Howard, Executive Editor at Farrar, Straus and Giroux, to dive into the wild world of publishing. They discuss everything from Jackson’s gay awakening—the animated Hercules—to who is writing the best sex, gay and otherwise. Tune in to learn what it takes to get published, and what editors like Jackson are looking for... and for all the gay literary gossip and Substack hot takes you’ve ever wanted.03:01 — Queer awakenings and gay tropes11:46 — How an editor chooses books15:59 — Reading, writing, and the publishing industry18:00 — The "gay lit boom"20:09 — BookTok and the purpose of reading22:24 — Toni Morrison and literary influence25:06 — Queer stories and identity in publishing27:31 — Solidarity in queer communities29:00 — The "gay moment" we're in35:45 — The history of the big, fat, wet kiss37:39 — Music, criticism, and creativity42:49 — Taste, book reviews, and literary culture56:43 — Discovering and editing great fiction01:00:50 — Sex writing and the next generation of writers
19. Writing Poems Before a Pregame, Rewriting Novels on the Dance Floor
56:36||Season 1, Ep. 19Debut authors Bobuq Sayed (No God But Us) and Kyle Carrero Lopez (Party Line) sit down with Ira to talk about the myth of "queer utopia," nightlife as never just escapism, and a shared disinterest in writing books about the obvious villain. Kyle and Bobuq also discuss refusing to leave their politics, their work, and everything else consuming their minds at the entrance of the club. Because for Bobuq and Kyle, the dance floor was never a break from reality… but where they go to feel it most intensely, among strangers and familiar faces. Turns out the club was never just for dancing.00:12 Alix Earle & the Literacy Crisis03:36 Structuring Poetry Collections 07:19 Gatekeeping in the Publishing World 12:58 Writer Burnout and Self-Care14:33 Writing Before the Pregame25:20 Unpacking the Queer Utopia 32:53 Literary Inspirations 37:38 Dream Parties41:19 Encounter with Assata Shakur 45:03 Book Launches & Nightlife Friendships 51:40 Advice for Debut Authors
18. I'm From Texas, Apparently with RHONY's Jessel Taank
51:56||Season 1, Ep. 18Jessel Taank is here, and she has some things to clear up! She joins Ira to discuss the fan reaction to her on the latest season of The Real Housewives of New York City. They get into her feud with Carole Radziwill, the Carolyn Bessette-Kennedy drama, her infamous Dorinda Medley fashion showdown, and her complicated relationship with Erin Lichy. Plus, Jessel reveals her plans to play matchmaker for Ira. 00:00 — Intro01:43 — Jessel Taank Joins06:18 — RHONY Fan Backlash07:40 — Erin & Setting Boundaries14:17 — Race & RHONY15:05 — Carole Radziwill & Carolyn Bessette-Kennedy19:47 — Dorinda & the Bubble Dress24:03 — RHONY Friendships & the New Cast33:36 — Fashion PR & Personal Style41:04 — Matchmaking44:27 — RHONY Zingers & Confessionals
17. Chris Black is the New Straggot Julia Fox
55:43||Season 1, Ep. 17Chris Black is everywhere and doing everything — co-hosting the podcast How Long Gone, building his American essentials clothing line Hanover, writing a memoir, and hanging in the DJ booth with Charli XCX's husband. He joins Ira to talk about his taste and how he developed it, from the 90s Atlanta hardcore scene that exposed him to life beyond a white, middle-class, suburban childhood, to the current "say yes" era he's living in — all while juggling sobriety, marriage, and still wanting to be in bed by ten.00:00 Taylor Swift Released New Music03:40 Chris Black joins Ira06:46 Writing Retreats & Isolation10:45 Books, Memoirs & Reading15:48 Manhattan vs. Brooklyn Living20:46 90s Hardcore Punk Roots24:48 The Value of Gatekeeping27:58 Managing a Band, TRL & MTV Nostalgia30:45 Video Podcasts vs. Audio34:37 His GQ Column & Bravo's Southern Charm36:42 Developing Taste via Magazines38:31 Launching Hanover Apparel40:16 Curation & Photography43:48 Ultimate Pop Diva Mount Rushmore53:29 Fantasy of Living Abroad
16. Marlon James: I Wasn’t Trying To Write a Gay Victim Book
01:12:48||Season 1, Ep. 16Marlon James joins Ira Madison III for a conversation about his new novel The Disappearers (which has been shortlisted for the 2026 Booker Prize), growing up in Jamaica, and the pop culture that shaped him. They get into Marlon’s complicated relationship with his own past, how Prince, Heathers, and ’90s grunge gave him a vocabulary, and why he wants readers to enter the world of his books on his own terms. If you haven't picked up a copy of The Disappearers yet... run, don't walk.00:00 Ira Madison III Ranks the Booker Prize 2026 Shortlist04:33 The Disappearers & Writing His Most Personal Novel07:56 Growing Up Queer in Jamaica12:12 Prince, Pop Culture & Queerness20:19 How He Writes & Gets Out of the Way32:17 How Pop Culture Shapes His Writing37:13 Jamaican Patois & Writing on His Own Terms45:15 Queer Sex, Shame & Writing50:14 Revenge, Trauma & Literary Perspective52:25 What Marlon Wants to Disappear From Literature56:58 Writing Multiple Perspectives01:06:22 How He Knows When a Book Is Finished