The Substack Success Podcast
The Substack Success Podcast

The Substack Success Podcast

Sarah Fay

Overview
Episodes

Details

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. Plus 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 Sarah Fay, Substack Writers at Work Founder and Director and former Paris Review interviewer. www.substackwritersatwork.com

Recent Episodes

Be Contrarian with Substack Icons Jessica DeFino and Emily Kirkpatrick
NOV 25, 2025
Be Contrarian with Substack Icons Jessica DeFino and Emily Kirkpatrick
<p><em>Welcome to the Substack Live Podcast!</em></p><p><strong><em>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.</em></strong><em> 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.</em></p><p><em>Brought to you by Substack Writers at Work Founder and Director and former Paris Review interviewer, Sarah Fay.</em></p><p>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:</p><p>* Why having tens and hundreds of thousands of subscribers doesn’t mean the Substack writer has it easy—far from it</p><p>* How to create your own platform and not to be platform-dependent</p><p>* 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</p><p>* Why consistency is everything—unless it’s not</p><p>* And so much more…</p><p><a target="_blank" href="https://substack.com/profile/7200709-jessica-defino">Jessica DeFino</a> is an award-winning beauty reporter and critic (the <em>New York Times</em>, the <em>Sunday Times, Vice</em>). She’s also written for <em>Vogue, Allure,</em> and more. She now writes the <em>Guardian’s</em> 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. <a target="_blank" href="https://open.substack.com/pub/jessicadefino">FLESH WORLD by Jessica DeFino</a> 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.)”</p><p>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 <em>People, i-D</em>, <em>The New York Times</em>, and <em>Vanity Fair,</em> among many others. Her newsletter <a target="_blank" href="https://open.substack.com/pub/emilykirkpatrick">I <3 Mess</a> is essential reading, whether you care about fashion or not.</p><p>Thank you, <a target="_blank" href="https://substack.com/profile/154488424-helen-roy">Helen Roy</a>, <a target="_blank" href="https://substack.com/profile/5498662-amy-gabrielle">Amy Gabrielle</a>, <a target="_blank" href="https://substack.com/profile/2626937-lynn-jericho">Lynn Jericho</a>, <a target="_blank" href="https://substack.com/profile/8493019-brad-wetzler">Brad Wetzler</a>, <a target="_blank" href="https://substack.com/profile/2364677-morgan-strehlow">Morgan Strehlow</a>, and many others for tuning into my live video with <a target="_blank" href="https://substack.com/profile/3047723-emily-kirkpatrick">Emily Kirkpatrick</a> and <a target="_blank" href="https://substack.com/profile/7200709-jessica-defino">Jessica DeFino</a>!</p><p></p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.substackwritersatwork.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">www.substackwritersatwork.com/subscribe</a>
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64 MIN
The Real Art of the Newsletter with Austin Kleon
OCT 7, 2025
The Real Art of the Newsletter with Austin Kleon
<p><em>Welcome to the Substack Live Podcast! </em></p><p><strong><em>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.</em></strong><em> 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. </em></p><p><em>Brought to you by Substack Writers at Work Founder and Director and former Paris Review interviewer, Sarah Fay.</em></p><p>You can also listen on your favorite podcast platform →</p><p>Over 700 people showed up to this live recording of the <em>Substack Live Podcast</em> 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: </p><p>* making what you want to see in the world,</p><p>* taking time to process in a world that wants us to just move on and scroll, </p><p>* writing the newspaper column you’ve always wanted to write, </p><p>* the <em>So what? </em>test,</p><p>and so much more…</p><p><em>The Atlantic</em> called Austin Kleon “positively one of the most interesting people on the Internet,” which is why his Substack is so damn good. </p><p>To have a Substack newsletter that people are interested in, it helps to be <em>interesting</em>, 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. </p><p>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. </p><p>He’s the <em>New York Times</em> bestselling author of a trilogy of illustrated books about creativity in the digital age—<a target="_blank" href="http://austinkleon.com/steal/"><em>Steal Like An Artist</em></a>, <a target="_blank" href="http://austinkleon.com/show-your-work"><em>Show Your Work!</em></a>, and <a target="_blank" href="http://austinkleon.com/keepgoing"><em>Keep Going</em></a>—and of <a target="_blank" href="http://austinkleon.com/newspaperblackout"><em>Newspaper Blackout</em></a>, a collection of poems made by redacting the newspaper with a permanent marker. </p><p>I love how he describes his trilogy, which is a masterclass in creativity and living a creative life:</p><p>* <a target="_blank" href="https://amzn.to/4nQIZXC"><strong><em>Steal Like an Artist</em></strong></a> is the book you give to somebody who’s just starting out and needs a kickstart or a boost.</p><p>* <a target="_blank" href="https://amzn.to/4q4MGLc"><strong><em>Show Your Work</em></strong></a> 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.</p><p>* <a target="_blank" href="https://amzn.to/46EgIh4"><strong><em>Keep Going</em></strong></a> 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 </p><p>***</p><p>About the Substack Live Podcast</p><p>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.</p><p>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.</p><p>Subscribe to receive every episode»</p><p>Thank you <a target="_blank" href="https://substack.com/profile/358060199-tom-sykes">Tom Sykes</a>, <a target="_blank" href="https://substack.com/profile/58646732-beth-spencer">Beth Spencer</a>, <a target="_blank" href="https://substack.com/profile/1814777-jason-chatfield">Jason Chatfield</a>, <a target="_blank" href="https://substack.com/profile/3251207-petya-k-grady">Petya K. Grady</a>, <a target="_blank" href="https://substack.com/profile/1076779-emilie-friedlander">Emilie Friedlander</a>, and many others for joining us.</p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.substackwritersatwork.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">www.substackwritersatwork.com/subscribe</a>
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65 MIN
Why Dopamine Hits Won't Get You the Creative Life You Want with Maya Popa
SEP 30, 2025
Why Dopamine Hits Won't Get You the Creative Life You Want with Maya Popa
<p><strong>Nearly 400 people showed up to listen to </strong><a target="_blank" href="https://open.substack.com/users/63627356-maya-c-popa?utm_source=mentions"><strong>Maya C. Popa</strong></a><strong> and I talk about:</strong></p><p>- The realities of pitching, publishing, and rejection</p><p>- Mindset, motivation, and the myth of “having it all together”</p><p>- Substack strategies, authenticity, and audience growth</p><p>- The dopamine loop, validation, and the writing process</p><p>and more…</p><p>Maya is a poet, prose writer, exceptional human, and someone I’m so lucky to call a dear friend. She’s the author of three books of poetry: <a target="_blank" href="https://www.amazon.com/Wound-Origin-Wonder-Maya-Popa/dp/1324021365/ref=sr_1_1?crid=3EBU330QBNTUK&#38;keywords=maya%20popa&#38;qid=1672756042&#38;sprefix=maya%20%2Caps%2C559&#38;sr=8-1"><strong><em>Wound is the Origin of Wonder</em></strong></a> (W.W. Norton 2022; Picador 2023), named one of <em>the Guardian’s</em> Best Books of Poetry; <a target="_blank" href="https://www.amazon.com/American-Faith-Maya-C-Popa/dp/194644846X"><strong><em>American Faith</em></strong></a><em> </em>(Sarabande 2019); and her third collection coming in 2026, which we’re all going to make sure it gets on the bestseller list. She’s also the Poetry Reviews Editor at <em>Publishers Weekly</em>. She’s been teaching for thirteen years at NYU and is just such an exceptional human. Her poems have been published in <em>The New Yorker, The Paris Review, Poetry, Granta, the Nation,</em> and elsewhere. </p><p>What I love most is Maya’s <a target="_blank" href="https://www.consciouswriterscollective.com/"><strong>Conscious Writers Collective</strong></a><strong> (CWC)</strong>, her online school and writing community that offers a rigorous, MFA-level education for writers without forcing them to take on the debt an MFA program would. Having taught at NYU and elsewhere at the graduate and post-grad level, she’s created a not-to-be-missed-out-on mentorship and training for writers at all levels, those who already have an MFA, those who might go on to receive one with the training they need to make the most of it, and those who may get enough to produce a body of work ready for publication without it. </p> <br/><br/>This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.substackwritersatwork.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_2">www.substackwritersatwork.com/subscribe</a>
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88 MIN