Phoebe Robinson is here, and she has thoughts! She joins Ira for a conversation about pop culture, comedy, and saying exactly what you think. They get into Phoebe’s viral wig rants, the strange state of celebrity podcasts, and why she wants people to stop treating pop culture commentary like the news. They also discuss Phoebe's return to stand-up, and what it really means to be in your "Rich Auntie" era.

Buy tickets to Phoebe's Feral and Fired Up! Tour: https://www.phoeberobinson.com/

00:00 Ira Talks About Dolly Parton

02:48 Phoebe Robinson’s New Book, “Rich Auntie”

05:37 Friendship, Boundaries, and Getting Older

06:53 Writing Books and Finding Her Voice

13:27 The Evolution of Podcasting Since “2 Dope Queens”

18:01 Phoebe’s “Wig Rants” and Sharing Opinions Online

24:00 Why She Doesn’t Have an Opinion on Everything

28:06 Creating Her Own Opportunities

31:44 The Responsibility of Comedy

37:49 Creating Tiny Reparations Books

41:07 Advice for Becoming a Better Writer

46:36 Giving Artists More Time to Create

48:30 Pop Culture, “The Valley,” and What She’s Watching

52:26 Problematic Celebrity Crushes

54:00 The Worst Things She’s Spent Money On

55:45 Books, London, and Lady Gaga

57:28 Why Men Should Read More Fiction

01:01:13 Do People Actually Read the Books They Post Online?

01:04:14 Book Covers and “You Can’t Touch My Hair”

01:05:19 Phoebe’s Dream Podcast Guest

Hosted on Acast. See acast.com/privacy for more information.

This week, Ira is joined by bestselling author Angela Flournoy for a conversation about writing, reading, and trusting your audience. Together, they discuss Angela’s writing group back in LA, the joy (and frustration) of Goodreads, why some books teach you how to read them, and the delicate balance between guiding readers and letting them figure things out for themselves. Plus, Angela explains why she's actually pro-feedback — and why every writer should resist the urge to Google themselves.

00:00 Intro: Ira’s Reading Habits and Tips from Well-Read New Yorkers

02:35 Angela Flournoy and The Wilderness

08:15 Writing a Novel Over Ten Years

10:57 Life as a Writer

18:16 Writing for the Page, Not the Screen

23:27 Toni Morrison and Teaching Readers How to Read

31:02 Writing Routines and the Pomodoro Method

37:50 Books, Prizes, and the Writing Life

43:52 Knowing When It's Time for a New Book

49:13 The Novel, Short Stories, and The Wilderness

52:59 Ghosts, Grief, and Loss

54:40 Friendship and Making New Friends

59:42 What Fiction Reveals About the Writer

1:02:15 Classic Books and Reading in 2026

1:05:55 Teaching Writing and MFA Programs

1:10:00 Goodreads, Reviews, and Feedback

Hosted on Acast. See acast.com/privacy for more information.

This week, Ira sits down with writer, cultural critic, and TikTok commentator Josh Lora (@tellthebeees) to unpack the cultural forces shaping what we watch, read, and obsess over online. They get into Christopher Nolan’s The Odyssey, the internet’s growing fixation on masculinity, and why TikTok has turned beauty, loneliness, and dating into a warped competition. Along the way, they debate the state of BookTok, the death of counterculture, and whether reality TV needs a little more mess. Plus, Josh explains the Harry Jowsey lore and why you absolutely do not need to watch Let’s Marry Harry.

00:00 Ira Madison III Introduces the Episode

04:21 Josh Lora Joins Ira: Christopher Nolan & The Odyssey

07:40 The Odyssey, Identity & Representation

12:05 Christopher Nolan’s Fascination With Masculinity

20:45 Masculinity, Guilt & the “Great Man”

24:29 Interstellar, Spider-Man & Male Loneliness

32:29 TikTok, Beauty Standards & Online Culture

41:09 Daria, Punk & the Death of Counterculture

46:55 Celebrity Fandom & the Rise of Stan Culture

52:58 BookTok, Reading Culture & DNFing Books

56:06 Why Internet Culture Is Getting Darker

01:06:41 Reality TV, Netflix & the Death of the Reality Star

Hosted on Acast. See acast.com/privacy for more information.