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Jon sits down with Andrew Postman (Glamour's "Jake: A Man's Opinion," 1990–94) and Ky Henderson ("The Guy Guru" at Cosmo 2006) to talk about life as male advice columnists for women's magazines in the '90s and 2000s. They swap origin stories — how each landed the gig almost by accident — and dig into the mechanics of the job: where the column ideas actually came from, the freedom, how they came up with topics and answers, and how their own dating lives bled into the columns in real time. They also reflect on the twilight years of print magazines and the lessons learned navigating freelance careers as the industry shrank.

Courtney Kocak grew up a small-town girl in Jackson, Minnesota, dreaming of becoming an actress. But her path to Hollywood led through some unexpected territory: seven weeks on the Girls Gone Wild tour, abusive relationships, an abortion, and eventually OnlyFans. During that time, she also became a celebrated writer, podcaster, and teacher. It's all laid bare in her new memoir, Girl Gone Wild, which chronicles how she transformed experiences she thought defined her shame into a writing career built on radical honesty. In our juicy conversation we talk about: Witnessing the exploitation tactics on the Girls Gone Wild bus  Raising over $32,000 for Black Lives Matter by offering topless photos to donors How you can be an exhibitionist but not an extrovert Writing dick reviews on OnlyFans as a creative writing exercise The difference between sexploitation and empowerment when it comes to monetizing your looks

Jeff Chang, author of Can't Stop Won't Stop, joins the pod to reminisce about when hip hop moved from park jams to mainstream America in the 1980s. From "Rapper's Delight" to Run-DMC's crossover moment to Rakim changing the flow entirely and Public Enemy making it political, Jeff breaks down the turning points. We revisit the so-called golden era debate, why the 80s deserve more respect, and our nomintations for the best rappers of this time.  For more content like this, subscribe to Small Talk  Wanna go to Gen X Con? Sign up

Joyce Maynard has been writing for 53 years. At 18, she landed on the cover of the New York Times Magazine, caught the eye of J.D. Salinger, and disappeared into a relationship that would define her for decades—until she finally told her story and was called a "predator" by Maureen Dowd. In this conversation, Joyce talks about being canceled before canceling was a thing, surviving as a Me Too survivor before Me Too became a movement, and why she returned to Yale at 65 only to discover she reads in the 17th percentile.  TIMELINE: 00:35 Being canceled before it was a thing 01:47 The New York Times Magazine cover story at 18 03:29 JD Salinger's letter and the beginning of their relationship 04:30 Moving in with Salinger and giving up Yale 05:39 Keeping the secret for 25 years 06:22 Writing "At Home in the World" and the backlash 08:26 When 18-year-olds dating 53-year-olds was "romantic" 09:41 The Charlie Rose interview (and what happened after) 10:27 Why the culture turned against her in 1998 11:23 Can you separate the artist from the art? 13:25 Teaching memoir to women in Guatemala 15:45 Writing family sagas and "How the Light Gets In" 16:31 Growing up in a problematic family 17:00 Mother's writing bootcamp from age 3 22:23 Including real-world events (Trump, January 6th) in fiction 24:09 Writing is not therapy or catharsis 29:43 Throwing away manuscripts that aren't good enough 30:08 Discovering ADHD at Yale at age 65 32:08 The D-minus French exam that changed everything 34:22 Reading in the 17th percentile 36:39 The gift of ADHD 40:39 "You cannot be a writer if you're not a reader" - and why that's wrong 41:48 Character-first vs. plot-first writing 43:33 Never knowing where the story will end (vs. John Irving) 44:18 No outlines - "outline is for a term paper" 46:22 Finding inspiration in news headlines 47:49 Why some stories are memoir and others are fiction 50:48 On sensitivity readers and the transgender character 51:44 When characters display "politically incorrect" attitudes 52:57 Fear of cancellation from the left 53:29 Trigger warnings at Yale and the softening of everything

Since its debut on Apple TV Plus, Pluribus has sparked an unusually intense response. Viewers not only watch it, they debate it and project onto it. Executive Producer Alison Tatlock talks about why the series has connected so deeply with audiences. We dig into the emotional problem at the center of the show, how skepticism shapes its characters, and why discomfort is doing more of the storytelling than plot twists or spectacle. We also talk about writing restraint, trusting viewers, and building a world that feels strange but uncomfortably familiar.  Subscribe to my newsletter @jonsmalltalk.substack.com

People in their 50s are confronting a financial reality nobody prepared us for. We grew up assuming steady careers, pensions, and a clear path to retirement. Instead, we're juggling layoffs, credit card debt, college tuition, aging parents, and rising healthcare costs, all while wondering what "retirement" even means anymore. Kerry Hannon and Janna, co-authors of Retirement Bites: A Gen X Guide to Securing Your Financial Future, break down how our generation ended up here and offer practical steps we can take now to build a future that feels possible, not panicked. Even if you're not Gen X, there is practical and useful advice for you here.  Subscribe to my Small Talk substack for more conversation like this

Former Hollywood TV writer Amy Suto walked away from Hollywood to build a seven-figure freelance writing business. She talks about the 3 pillars that got her there, the Substack tweaks that added $100,000 in value, and why self-publishing can earn more than traditional book deals. Amy's new book is Write for Money and Power: The Anti-Starving Artist's Guide to Becoming a Seven-Figure Writer. Follow us on Substack: Amy Suto Jonathan Small

Lili Zarghami spent decades working in women's magazines before realizing none of them were speaking to women like her anymore. After turning 40 and getting laid off, she decided to create Jenny Mag—a digital magazine for Gen X women who don't fit the cookie-cutter mold of traditional women's media. In this conversation, we discuss why dating stories outperform health content, the complicated relationships Gen X women have with their Boomer mothers, what it's like running a magazine on nights and weekends with zero budget, and why owning your platform matters when you've been disposable to corporate publishers one too many times. Lili also opens up about empty nesting with twins, being back in the dating world after 25 years of marriage, and creating content that makes readers say "I thought it was just me."  This episode originally aired on my new podcast Small Talk. Subscribe to Small Talk Podcast Small Talk Substack Jenny Mag

The legendary crime writer talks about how she builds characters, steals voices, mines real communities for detail, and turns dark human behavior into bestselling fiction. We also get into real police sources in London, writing about Nigerian communities and FGM in a way that doesn't get you canceled, and the piece of advice PD James gave her that changed her life forever. Follow me @ [email protected] Try AG1 and get a FREE bottle of Vitamin D3K2 AND 5 free AG1 Travel Packs with your first purchase @ drinkAG1.com/writeaboutnow

Smartphones and social media have changed childhood in ways few of us could have predicted. For starters, many children are now getting their first phone at just 10 or 11 — far younger than the technology was ever designed for. Once that phone is in their hand, it can interfere with sleep, friendships, independence, and even mental health. So what can parents do? Guest Jean Twenge, Ph.D,  is a professor of psychology at San Diego State University, the author 10 Rules for Raising Kids in a High-Tech World. In this books she gives parents some really useful suggestions roadmap for helping their children deal with this epidemic. Jean talks about how the culture around childhood has shifted since the rise of smartphones, and what concrete steps parents can take right now to raise healthier, happier, more independent kids. Order AG1 @ drinkag1.com/writeaboutnow Subscribe to my Substack@ jonsmalltalk.substack.com

My guest this week is Kaila Yu. Her new memoir, Fetishized: A Reckoning with Yellow Fever, Feminism, and Beauty takes on a provacative question: what happens when you've built a large part of your career in a culture that objectifies you? And how complicit are you in keeping that culture alive? Kaila looks back at her years as a model and musician, and then forward to the harder work of reclaiming her story and challenging the stereotypes that still harm Asian women today. Subscribe to my Substack: [email protected]

Captain William Kidd is one of the most famous names in pirate lore. But what if he wasn't actually a pirate at all? In this episode, bestselling author and scientist Samuel Marquis joins me to talk about his new book Captain Kidd: A Story of Treasure and Betrayal. Marquis has a personal stake in the story — he's Captain Kidd's ninth great grandson. We talk about Kidd's rise from colonial sea captain to pirate-hunter, the murky politics of the time, his dramatic trial in London, and the love story that's rarely told. Marquis argues Kidd was less Blackbeard and more fall guy — a man caught in a scandalous power struggle between the English crown, shady investors, and the East India Company.  Subscribe to Jon's Substack Small Talk  This episode is sponsored by AG1.

When I helped launch Twist magazine in the late '90s, we basically huddled around old issues of Sassy like sacred texts, trying to decode what made them so special. The answer? Jane Pratt. So it was with excitement and a little nervousness that I jumped on a Substack Live Interview with her. We chatted about: Her miserable boarding school experience and how it inspired Sassy Getting pulled off 70% of newsstands after a boycott by the religious right The secret behind Sassy's success and why it changed so many lives Her evolution from Sassy to Jane Working with Michael Stipe, who she dated for years and now calls her best friend and daughter's godfather Her decision to launch Another Jane Pratt Thing on Substack rather than a standalone website How she finds new writers and spots a good story What makes her such a good editor Gen X resilience Why she hates the word "influencer," even though she was one of the first Her optimism about the current state of the media Name dropping The shift to multi-hyphenate careers, and what she puts as her profession on doctor's forms. Subscribe to Small Talk to hear more Substack Live interviews with interesting folk.

Historian Hampton Sides joins the show to talk about The Wide Wide Sea, his riveting new book about Captain James Cook's final—and fatal—expedition in 1776. We get into: Why Cook lost his cool on his last voyage What really happened in Hawaii The crew's wild sexual escapades in the South Pacific What this story reveals about power, empire, and the price of discovery Subscribe to my Substack @ JonSmallTalk

Guest Kim Dower has spent the last 40 years helping authors get noticed — as one of the top literary publicists in the business. She's also a celebrated poet, with a brand-new collection out now called What She Wants. In this episode, Kim pulls back the curtain on what publicists actually do, who really needs one, and the biggest mistakes authors make when trying to promote their work. If you're publishing a book — or even thinking about it — this conversation will help you understand the industry, the stakes, and what it takes to break through. Subscribe to my Substack: JonSmallTalk.substack.com Order AG1: DrinkAG1.com/writeaboutnow