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Substack Live Podcast

Sarah Fay

Your weekly behind-the-scenes look at what’s happening and working on Substack—with the platform’s leading Growth Strategist, Sarah Fay. The only podcast that helps you stay ahead of the curve as Substack changes and changes again and again, so you can use it to fuel your creative, professional, and financial life. Plus, conversations with the best writers and creators who came to Substack early and made the platform great to show you how to create and, yes, monetize, not by gaming a platform but by bringing your amazing work to the world and making the world a better place in doing so.

www.substackwritersatwork.com
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  • 20 episodes
  • Avg 29 min
  • English
  • Tuesday · 6 min

    Why Substack Is So Difficult (and Strange)

    “There are many Substacks about Substack. This one is the OG.” —Gregg Easterbrook Today we talk about the reality of Substack, a reframed I want you to make, and a revelation I want you to consider. This is about figuring out why your Substack might be stalled, maybe a little jammed, maybe not getting started. It's not you. It's Substack. And if you're not a paid subscriber or free subscriber to Substack Writers at Work, please come join us: https://www.substackwritersatwork.com/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • September 29 · 15 min

    How One of My Premier Members 5x’d Her Subscribers in One Year

    From the Diary of the Leading Substack Strategist… This week, I share how important your Substack DNA is and a way to start finding it. It's not easy, and it takes some work. It's why I've taught it for 5 years and why I know that it works: my clients, my Premier members, and even my subscribers, the moment they find it, they grow. It's fantastic. Enjoy, and become a paid subscriber to Substack Writers at Work. I'd love to have you. https://www.substackwritersatwork.com/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • September 25 · 30 sec

    How Five of My Favorite Substack Built Massive Followings without Losing Their Souls

    This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.com Here I discuss how five of my favorite Substacks (though I go into more than five) created amazing platforms without losing their souls. That means a range of subscribers from 2,000 to 50,000. For all Substack Live Podcasts, join Substack Writers at Work: https://www.substackwritersatwork.com/

  • September 11 · 2 min

    Live with Elizabeth Gilbert: When a Substack Becomes a Spiritual Practice

    This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.com Normally, I would do a written summary, but this is one you need to watch or listen to on your favorite podcast platform: * Remind yourself why you’re on Substack in the first place. (Spoiler: it begins with an f.) * Find out how this might actually be the golden age of writing. * Discover the magic of putting your right hand in your left armpit. You can get Substack “information” anywhere. Paid subscribers get guidance from founding Substack writers who’ve mastered the platform and made it their own in Lives like this one with Liz Gilbert. Become a paid subscriber today! You can get Substack “information” anywhere. As a paid subscriber you get access to founding Substack writers who’ve mastered the platform and made it their own in Lives like this one with Liz Gilbert. This is exclusively for you. My Substack Live series features writers, creators, teachers, and visionaries who’ve created something entirely new and/or transformed their Substack into community gathering spaces, educational institutions, cultural touchstones, and/or works of art. Previous guests include Elizabeth Gilbert, Susan Cain, Austin Kleon, Mason Curry, Jessica DeFino, and Emily Kirkpatrick.

  • July 31 · 40 min

    How Susan Cain Built 'The Quiet Life' to 275,000 Subscribers

    Nearly 400 people joined us live to talk about Susan Cain’s amazing Substack The Quiet Life. If you don’t know Susan Cain, she’s the author of the mega bestsellers “Quiet: The Power of Introverts in a World That Can’t Stop Talking” and “Bitter Sweet: How Sorrow and Longing Make Us Whole.” She was a lawyer before becoming one of the most compelling writers of our time. We talk about envy and jealousy, how to write your posts/articles as kindred letters, how loving what you do makes a successful Substack and a more enjoyable life, the magic of her candlelight chats (the community feature she offers as an introvert and for introverts), and why "vibe" might just be the word for 2026. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • July 14 · 21 min

    Newsletter Dating, the New Restack, and more

    “There are many Substacks about Substack. This one is the OG.” —Gregg Easterbrook This week: Substacks making news, newsletter dating, Substack in Japan, why you don’t have to go viral on Notes anymore, it’s okay to ask for what you want, the new way to restack your posts, and who’s here. SW@W homepage | Premier homepage | Substack Starter Pack | 24/7 Community Chat | Manage your subscription | Book a 3-Month Substack Growth Package 1:1 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • July 10 · 50 min

    How Letter Writing Will Make You a Better Writer with Lindsay Hurty

    Today’s live was phenomenal! Please listen to the podcast version while you’re cooking this weekend or walking or running or whatever. In my live with the amazing Austin Kleon reminded me that on Substack, we’re writing news-letters. I wanted an expert in letter writing to share how exactly the principles of letter writing could help us be better writers on Substack and write more engaging Substack articles. Lindsay Hurty offered a wealth of advice on how we can use letters and the act of letter writing in many different ways to nurture our subscribers and write better Substack articles. (You can subscribe to her Substack here.) Be sure to listen, too, because the story she tells in the beginning will (if I have anything to do with it) someday be a viral TED Talk. SW@W homepage | Premier homepage | Substack Starter Pack | 24/7 Community Chat | Manage your subscription | Book a 3-Month Substack Growth Package 1:1 with me This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • June 19 · 5 min

    Masterclass: How To Get a Brand Deal on Substack

    This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.com Brand sponsorships on Substack aren't just about some sort of weird brand placement that's awkward. I t's about rethinking Substack and how you make money on here, and how we support each other in making money. In this episode, I give you everything you need to know about Substack's new brand sponsorships program — how it works, what brands actually want, and how to fill out your Creator Kit strategically, not generically.

  • June 3 · 8 min

    Dispatch from Substack's 2026 New York City Summit

    The highest earners on Substack aren't debating whether to use AI. They're asking a better question: how to stay valuable in a world that's full of it. I spent a day in New York in a room with some of the biggest names on the platform, and the words that kept surfacing weren't the ones the growth-advice economy sells. No one said hacks. No one said viral. What they talked about was fun, taste, and the person behind the words. This episode covers: *Why the era of giving your best work away for free may be over. *Which skills are about to gain value on Substack, and which are about to lose it. *Why slow, steady growth is the only kind with substance. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • May 5 · 20 min

    The Minimalist's Guide to Substack: The Magic of the Golden Nugget Post

    Welcome to our new series for paid subscribers: “The Minimalist’s Guide to Substack.” Declutter your Substack brain and life, so you can actually grow in what is an increasingly crowded Substack landscape. The biggest mistake I see on Substack is people making it way too complicated. Principle #1: Post when you have something worth sending. Each post should pass two tests: Is this something people need right now? Is this something they could get from ChatGPT? Enter the Golden Nugget post. It's an easy, short post you can create when you don't have time for a full, high-quality post. A gift—a book, a song—something that doesn't ask readers to do anything. A full post, not a Note, that comes from a genuine desire to share one thing that means something to you right now. No call to action, no questions for comments. Don't make readers do any work. But a Nugget post isn't about you. It's a gift to your readers—something they can absorb without much effort. The Nugget gives you and your readers breathing room while maintaining connection. Join SW@W Book a Substack Strategy 1:1 with me This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • April 4 · 5 min

    The Million Dollar Question: Do Substack Followers Really Become Subscribers?

    This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.com Nearly 250 paid subscribers came to the monthly paid-subscriber live with Seth Werkheiser of SOCIAL MEDIA ESCAPE CLUB. » I love when we all get to be together. Seth walked us through a 4-step approach to Notes that converts, pulls you out of your comfort zone by showing you how to engage with others, and stops you from feeling like you’re just posting into the void. Listen for more and if you aren't a paid subscriber to Substack Writers at Work, become one: www.substackwritersatwork.com

  • March 2 · 41 min

    Write Openings That People Open

    How your Substack posts land in your reader's inbox matters more than you think. In this live, I walk through what your subscribers actually see when your post arrives, how to find out where you're being read (email, app, or web), and why creating a familiar, consistent post structure is more important now than ever. I also cover what's working with images, why stock photos can devalue your writing, and how to think about your opening lines so readers actually want to stay. https://www.substackwritersatwork.com/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • January 27 · 14 min

    3 Home Remedies for Substack Writer’s Block

    Part of the Substack Writer at Work Series. In 2026, I’ll be giving paid subscribers and Premier members a taste of the writing guidance I use with my students at Northwestern and my Craft of Writing on Substack course. Today, we dive into Substack writer's block, a unique but common ailment. Substack writer’s block looks like not posting—or posting lifelessly. Or giving up entirely. There are a lot of dead Substacks: Many as a result of “writer’s block.” SW@W homepage » Thank you for being part of the best community on Substack! Please share Substack Writers at Work and invite others to join us for real, long-term Substack growth. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • January 14 · 1 min

    Live Substack Notes Writing Workshop

    This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.com Navigating SW@W: SW@W homepage | Premier Membership homepage | 2026 Notes Boost Challenge | Paid/Premier Chat | 2026 Substack Pathway | Upcoming courses & Intensives | Substack Essentials Workshop library | Archive | Index | Guidance on Notes, Growth, Revenue, Writing on Substack, Serialization

  • Dec 9, 2025 · 1 hr 3 min

    Self-promotion for people who hate self-promotion

    Maya C. Popa and I talk about self-promotion for the self-promotion averse. Find out why self-promotion is all about bravely falling backward into a ball pit and why we can blame our dislike of it on the Modernists, Roland Barthes, and the Iowa Writers Workshop. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • Nov 25, 2025 · 1 hr 4 min

    Be Contrarian with Substack Icons Jessica DeFino and Emily Kirkpatrick

    Welcome to the Substack Live Podcast! Conversations with the best Substack early adopters who created amazing newsletters and continue to bring their good work to the world and make the world a better place in doing so. Plus, get updates and expert guidance on the platform as it changes and changes again and again, so you can use it to fuel your creative, professional, and financial life. Brought to you by Substack Writers at Work Founder and Director and former Paris Review interviewer, Sarah Fay. Over 300 people showed up to this live recording of the Substack Live Podcast to hear Emily Farra and Jessica DeFino talk about how they built newsletters that became something bigger than the platform itself, including: * Why having tens and hundreds of thousands of subscribers doesn’t mean the Substack writer has it easy—far from it * How to create your own platform and not to be platform-dependent * Why it’s ill-advised to try to write a “genius essay” every week on demand and it’s better to create a framework you can apply consistently * Why consistency is everything—unless it’s not * And so much more… Jessica DeFino is an award-winning beauty reporter and critic (the New York Times, the Sunday Times, Vice). She’s also written for Vogue, Allure, and more. She now writes the Guardian’s beauty advice column, Ask Ugly, a position that arose out of her Substack. Adweek named her one of their Creative 100 for 2023. She’s smart and sharp and funny and wry. FLESH WORLD by Jessica DeFino is “the newsletter the beauty industry fears.” She’s a Substack icon who showed what’s possible beyond the platform. And her CTAs are the best, e.g., “Subscribe now. (Because retinol won’t work in the face of your mortality.)” Emily Kirkpatrick is the Roland Barthes of fashion writing—with a little bit of Stephen Wright and Tig Notaro mixed in. She’s written for People, i-D, The New York Times, and Vanity Fair, among many others. Her newsletter I <3 Mess is essential reading, whether you care about fashion or not. Thank you, Helen Roy, Amy Gabrielle, Lynn Jericho, Brad Wetzler, Morgan Strehlow, and many others for tuning into my live video with Emily Kirkpatrick and Jessica DeFino! This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • Nov 6, 2025 · 57 min

    The (Substack) Writer’s Growth Mindset with Maya Popa

    It was so fun to talk about the importance of mindset when you're a writer and a Substack writer. It’s everything. Substack Writers at Work is the only expert guide to Substack. * We’re one of the Top 10 Substacks, globally—a bestselling Substack featured by Substack and trusted by writers and creators since 2022. In case you don’t know me, I’m the leading Substack Strategist. I’ve been on this platform for over five years and over a thousand writers and creators 1:1 and tens of thousands on Substack Writers at Work. Everything you get on Substack Writers at Work is based on real results: clients who’ve doubled, tripled, and 10x’d their subscribers; grown their revenue; produced their best work; and built deep engagement. Join us. www.substackwritersatwork.com This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

  • Oct 7, 2025 · 1 hr 5 min

    The Real Art of the Newsletter with Austin Kleon

    Welcome to the Substack Live Podcast! Conversations with the best Substack early adopters who created amazing newsletters and continue to bring their good work to the world and make the world a better place in doing so. Plus, get updates and expert guidance on the platform as it changes and changes again and again, so you can use it to fuel your creative, professional, and financial life. Brought to you by Substack Writers at Work Founder and Director and former Paris Review interviewer, Sarah Fay. You can also listen on your favorite podcast platform → Over 700 people showed up to this live recording of the Substack Live Podcast to hear Austin Kleon give some of the best advice on how to have a newsletter/Substack that means something to you and your readers, including: * making what you want to see in the world, * taking time to process in a world that wants us to just move on and scroll, * writing the newspaper column you’ve always wanted to write, * the So what? test, and so much more… The Atlantic called Austin Kleon “positively one of the most interesting people on the Internet,” which is why his Substack is so damn good. To have a Substack newsletter that people are interested in, it helps to be interesting, which typically comes when the writer of said Substack is interested in the world and specifically, the part of the world he writes about in a way no one else can. Austin was Substack before there was Substack, having started his newsletter in 2013, before Substack existed. He came to Substack in 2021 because, he said, he liked the simple interface. He’s the New York Times bestselling author of a trilogy of illustrated books about creativity in the digital age—Steal Like An Artist, Show Your Work!, and Keep Going—and of Newspaper Blackout, a collection of poems made by redacting the newspaper with a permanent marker. I love how he describes his trilogy, which is a masterclass in creativity and living a creative life: * Steal Like an Artist is the book you give to somebody who’s just starting out and needs a kickstart or a boost. * Show Your Work is for the person that has found their thing but they haven’t been found themselves yet — people who need to self promote or need to get their work out there. * Keep Going is really the book for people who are trying to make a career out of creative work — people who are trying to be in it for the long haul *** About the Substack Live Podcast Join me for conversations with Substack early adopters who created amazing newsletters and continue to bring their good work to the world and make the world a better place in doing so. I also bring you updates and expert guidance on the platform as it changes and changes again and again, so you can use it to fuel your creative, professional, and financial life. Subscribe to receive every episode» Thank you Tom Sykes, Beth Spencer, Jason Chatfield, Petya K. Grady, Emilie Friedlander, and many others for joining us. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

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