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.

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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. 

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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.

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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

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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 

A lot of Gen Xers are facing an existential crisis, feeling stuck, burned out, unemployed, and just unsure about the future. This was supposed to be the time when we start to wind down so why does it feel like we're on a highway to hell? This doesn't mean we're doomed; it just means we need a reset on how we think about retirement. In my first-ever Substack Live over on my newsletter Small Talk, I had a live conversation with Brian Clark—entrepreneur, writer, and founder of Further—about what this next chapter actually looks like for Gen X. And how we can stop chasing old myths and start building something more sustainable and sane.

For more content like this, follow me over @ jonsmalltalk.subtack.com

Get a discount on AG1 @ drinkag1/writeaboutnow.com

Gretchen Rubin joins the show to talk about her new book, Secrets of Adulthood, in which she boils down a lifetime of wisdom into powerful aphorisms that resonate. Gretchen is a bestselling author, podcast host, and one of today’s most trusted voices on happiness, habits, and human nature. In this conversation, we talk about the lessons we learn too late, the advice she wants to pass on to her daughters, and why small, well-phrased truths often carry the biggest impact.

Other topics: – Why she made the leap from clerking at the Supreme Court to writing about happiness – The Four Tendencies framework and why so many of us are "Obligers" – Her process for crafting sticky, memorable aphorisms – Why motivation doesn't work as a motivation tool

Subscribe to my Substack @ https://jonsmalltalk.substack.com/

This show is sponsored by AG1. Sign up for a $76 discount @ DrinkAG1.com/writeaboutnow

When the New York Times declared it was “the end of work as we knew it” for Gen X, it did not feel fine. The story called the generation obsolete, irrelevant, and even likened them to candlestick makers in the age of electricity. Seriously? The article sparked a firestorm, prompting host Jonathan Small to write a viral Substack response that only raised the temperature. Now, Dana DuBois—fellow Gen X-er, writer, alt-rock aficionado—joins the show to talk about why the article sparked so much rage, what it got dead wrong, and how Gen X is not just surviving but reinventing midlife on their own terms. 

Read Jon's response on Substack here. 

Read the original NYT story here.

All things Dana DuBois can be found here. 

Has anyone ever told you, "Your life is so interesting—you should write a memoir!" It's flattering, no doubt. But then comes the doubts and the fears and the paralysis. How do you transform decades of memories and anecdotes into a narrative people would actually want to read? You can start by reading guest Wendy Dale's new book, The Memoir Engineering System. In it, she gives you the structure for constructing your memoir from the ground up. On this episode, we talk about useless writing advice such as just write a first draft, why the journey is more important than the memories themselves, and the things to prep yourself for capturing your life on the page in the best way possible.

Write About Now is sponsored by AG1, order using my code and get some freebies.DrinkAG1.com/writeaboutnow 

Subscribe to the Small Talk substack @ https://jonsmalltalk.substack.com/

Back in Hollywood's Golden Age, two men with vastly different backgrounds came together to shape the future of film. Louis B. Mayer, a shrewd businessman and Irving Thalberg, a visionary producer, formed a partnership that defined MGM and set the standard for the modern studio system. In this episode, famed film critic Kenneth Turan explores their unlikely partnership, their imperial rise, and their eventual fall.