Substack Live Podcast

As people scramble onto Substack, it’s easy to overlook why it’s the platform to be on right now: Certain early adopters spent years creating Substack newsletters so good people would actually read and paid to read them. Which is why I’ve created an entire podcast to share them with you.My conversation with Mason Currey contains some of the best advice on how to stop feeling like you have to chase the algorithm and can set about owning your platform and doing your best work. Nearly 300 people showed up for the live recording. If you don’t know Mason, he’s the author of the Daily Rituals books and writes the Substack newsletter Subtle Maneuvers about how creative people get work done. Cal Newport called him “the undisputed master of finding, in the messy lives of great artists and thinkers throughout time, deeply human lessons about cultivating meaning in our current age.” * This is some of the best advice on how to build a Substack that people will spend their time and money reading.* + How to stop chasing the algorithm and own your platform.6 Ways to Build a Substack People Will Actually Spend Their Time and Money Reading1. Don’t call it your SubstackMason doesn’t say “my Substack.” He says “my newsletter.” The distinction keeps him focused on the writing, not the platform dynamics.“When you think ‘my Substack,’ you start thinking about Notes, recommendations, leaderboards, what other Substacks are doing. When you think ‘my newsletter,’ you think about your readers and your work.”2. His writing processWhen writing, Mason doesn’t necessarily think about what will get subscribers. He’s thinking about what hits him and what will hit his readers.“I’m always really thrilled when I read something or hear something in a podcast. I have my feelers out for that thing that makes me kind of sit up in my chair. When my spidey sense kind of tingles, I think okay, that could be a good newsletter. That’s something that I feel like really hit me and maybe it’ll hit my readers too.”3. You don’t have to be confessional to connect with your readersMany people aren’t comfortable with or don’t want to divulge every aspect of their personal lives on their Substacks. Mason doesn’t overshare but it still feels he’s talking to you. You experience his mind through what interests him, what he struggles with, what he finds in other people’s stories.“You don’t know a ton about me but I think it somehow influences when I’m writing about somebody else’s process—you can believe that there’s a lot of me hidden in there.”4. When to go paidMason started his newsletter in February 2020 with 74 subscribers. For two years, he built something good before going paid.When Substack introduced recommendations, his growth spiked because (that’s right) his Substack was really good.When I asked what made him decide to turn on paid subscriptions, he said: “I guess I just saw all these people making like six and seven figure incomes. And I was like, maybe I’ll just turn it on. I said, you know, it’s the same thing. But if you feel like you want to chip in to support it, feel free. And people did. It was wonderful.”Over time, he’s added community features—a morning co-working Zoom at 6 AM (which is wild), a book club. But the newsletter itself stays free.Mason said: “I’ve thought a lot about different things I could do and this is one that I feel good about. I don’t feel like I’m out there trying to sell, sell, sell. It feels sustainable and true to the spirit of the newsletter. Even if it’s not maybe as profitable as it could be.”You don’t have to wait two years or even two months, but don’t rush to it until you have something worth paying for.5. Go analogMason’s research process is tactile. He reads physical books from a physical library, marks pages with acutal sticky notes, scans those pages, prints them, then goes back through with a pen and makes notes.He said: “That way I feel like I get to sort of run it through my brain at least twice.”I know someone who does this with Kindle, where they print all their highlights and review them. You’ll only remember 20 percent of what you read if you don’t review it, but if you do review, you’ll remember 80 percent.Mason’s process can’t be rushed. It produces original thinking because it’s been filtered through his brain twice, processed through his hands, connected to his interests and the way only he sees the world.6. His advice for anyone just starting or who feels stalledWhen I asked Mason what advice he’d give someone starting out or feeling very frustrated, he said: “I would just figure out what writing you want to do that you would do for yourself or for your friends. Or if someone whose writing you like were to read it, what would you be happy for them to read of yours? I would just leave out the subscriber numbers and the money thing and just try to produce something you’re proud of that you can build up a collection of over time.”Mason’s new book is Making Art and Making a Living, coming out in March 2026. My passion is to help Substack writers reach the bestseller lists by leveraging the Substack network, so please pre-order now. » Pre-ordering a book is quite possibly the most important way you can support a writer. My interview with Mason is part of 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 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.For paid subscribers: 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

For the only expert guide to Substack, join Substack Writers at Work with the leading Substack Strategist Sarah Fay: https://www.substackwritersatwork.com/Substack has fundamentally changed—and that's actually the best thing that could happen to us. While everyone's panicking about algorithm changes, trolls, and platform noise, we need to see why Substack 5.0 is our opportunity to build something bigger.In this episode, we break down why treating Substack like social media will hurt your growth.We keep growing, we keep earning, but we stop being "on" Substack like it's Instagram. We use it as a launchpad for books, speaking, media opportunities—not another hamster wheel.Every single one of my 42,000 subscribers has been hard-earned through deep work, not tricks. This isn't about growing less—it's about growing smarter while everyone else burns out chasing the algorithm. 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

** Use the Know Your Subscribers Implementation Guide PDF below to make this much easier.Too often, when we try to get subscribers or likes or conversions, we don’t even know who we’re trying to engage or upgrade to paid.The tricky part is that our person changes and we change and Substack is always changing, so we always have to be checking in.In marketing-speak, they call it your “avatar.” Sometimes it can be helpful to approach it in the usual ways. But the world has changed and people have changed and their buying habits have changed and their subscribing habits have changed. In a world where AI can spit out information, we need to connect as actual humans. That means knowing exactly whom we’re writing for.What we coverI walk you through my process for getting to know your actual readers—not some made-up avatar, but the real people reading your work. We dug into where they’re reading you, what they're Googling at 2am, what they’re sick of reading about, and more.* (00:00:50) - Forget the Substack drama. Focus energy on “you and your people” rather than getting caught up in speculation about Substack’s future changes.* (00:02:59) - Move beyond traditional “avatar” marketing speak to understand your actual readers and their real experiences.* (00:08:27) - For Writers: Ask three key questions about your readers.* (00:10:03) - For Creators/Coaches/Teachers: Use these three questions to get at the problems your audience faces* (00:18:56) - Using this guide to find ideas for your next posts.* (00:23:47) - Differentiate from AI by sharing your experiences rather than just information.* (00:29:41) - Better CTAs than “support my work.”* (00:38:29) - On Substack, you play five roles: You’re writer, editor, publisher, salesperson, and publicist. Fill this out during our live workshop. If you’re watching the replay, set a timer for each, so you keep this short.Save this document. Bring it to the paid-subscriber-only workshop on Friday, 8/1, where we’ll go through your entire subscriber flow to grow your Substack. Details to come.Thank you Rachel Botsman, Darien Gee, Petya K. Grady, Debbie Weil, Alexander Verbeek, and many others for tuning into my live video! Join me for my next live video in the app.Use the Know Your Subscribers Implementation Guide PDF below.Word version: * https://tinyurl.com/3fz88zypPDF: 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

I love getting to do this with all of you.This goal-setting session is the best 40 minutes you can spend. I’m not just saying that. I did it this morning, too.Participating in this session will transform the next three months for you.Let me guide you for 40 minutes.You’ll leave knowing what matters to you and who you want to become; where to focus; and where to spend your time, attention, energy, and (yes) money.The 4 steps to achieving your Substack goalHaving a goal is and isn’t about achieving the goal.It’s about four things: Having a ritual of appreciation, discovering what’s most important to you right now, knowing where to focus your efforts, and becoming the person you want to be.Step 1: Ritual of AppreciationHaving a goal is about having a ritual to appreciate what you’ve done during a certain period of time, regardless of the goal, and what and who helped you get there.Right now: Write down three successes in your Substack.Those could be:* Subscribers* Paid subscribers* Producing posts you’re really proud of* Making connections* Getting engagement in the comments* Getting likes* Having people restack your posts* Showing up in the Notes Boost Challenge* RevenueTake a moment. Celebrate these. Really feel them in your body.Now, who helped you achieve them?* Family* Colleagues and friends on Substack* Friends* Substack guides/teachers* Substack—the platform* Food in your fridge that nourished you* Animals (maybe your cats :)* Sunlight and fresh air on your walks* The yoga mat you stretched on* The water in your tap that hydrated you* The bed you slept onMaybe send them a thank you.Step 2: What matters most to you (right now)Choosing a goal helps us discover what’s most important to us right now.* Choose one Substack goal for Q3 (July, August, September).One goal.The beauty of goal setting is that it also helps you determine what matters most to you right now.Start by eliminating from this list what’s non-essential:* Subscribers* Paid subscribers* Producing posts you’re really proud of* Make more connections* Get engagement in the comments* Get more likes* Have people restack your posts* Show up in the Notes Boost Challenge* RevenueThat will lead you to the one goal that’s essential to you right now.Write it down.Step 3: Become who you want to beTrying to achieve a goal is about who you want to become.If I just want money or subscribers or likes or even connection, it will likely feel empty whether I achieve it or not.* Who do you need to become to achieve your goal?* Fill in the blank:* Someone who ______.Write as many as apply.Step 4: Focus your time, attention, energy, and moneyWhere will you focus your time, attention, energy, and money in Q3 to achieve your goal in a way that going for it brings you more calm and health?* Time* Attention* Energy* MoneyFrom these, write down two small teeny action steps you can take and take them!Thank you (!) Meghan Daum, Susie Bright, Debbie Weil, Amy Gabrielle, Francesco Turrisi, and many others for tuning in.Share your goal or any part of this process with us. And then find someone to meet and say hello. Also, if you’re new or haven’t been to our paid-subscriber chat (!), please go and introduce yourself and your Substack. Our community is one of the best parts of your subscription. Don’t miss it! 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

So many writers want to be featured by Substack.It can bring thousands of new subscribers. Being featured signals you're producing authentic work, not AI content. It puts you in excellent company with other quality creators.Today, we're talking about the one thing that actually matters for Substack success—and it's not posting more, growing faster, or any of the surface-level tactics everyone's obsessing over.I take you inside how Substack decides who to feature.Go to www.substackwritersatwork.com and get the workflow I created to help you raise the quality of your posts to featured-Substack level. 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

Subscribe to Substack Writers at Work: www.substackwritersatwork.comToday, we talk about subvocalization and how important it is to reading and voice and how important it is to writing. Voice is one of the hardest craft skills to teach and learn. If more Substack writers and authors had it, a lot more of them would be earning an income. The most profound subvocalization-causing effects—your authentic voice, i.e., you—are rendered during the messy middle of the writing process. Past brainstorming and drafting, we get into revision and editing, where you render your voice into silent words. 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

This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.comThank you Joy Sullivan, Jo Hutton, Dr Kondrot, Beth Spencer, Diana Spechler, and many others for tuning into my live video! Join me for my next live video in the app.

To listen to the full episode, join us at Substack Writers at Work!https://www.substackwritersatwork.com/In today's episode:Learn how to grow your Substack with live shows, discover author success secrets from Jason Chatfield & Mikala Jamison, plus March's top engagement strategies from Substack's leading expert.00:00 Introduction and Welcome01:15 Meet the Guests: Mikayla Jamison02:26 Meet the Guests: Jason Chatfield05:09 Mikayla's Substack Journey06:07 Jason's Substack Journey09:43 Book Deals and Publishing Insights23:44 The Role of Substack in Book Deals33:35 Marketing Strategies and Long Tail Sales36:41 Promoting the Book: Strategies and Tips37:10 Event Planning and Live Streaming37:25 Drawing Book Plates: A Quick Skill38:12 Marketing and Substack Growth39:09 Engaging Readers and Building Community40:34 Live Storytelling and Fringe Festival43:27 Pre-Order Campaigns and Bestseller Lists50:21 Advanced Review Copies and Social Proof55:54 Supporting Fellow Authors and Community01:01:11 Using Substack for Book Launches01:07:19 Final Thoughts and Pet Cameos 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

Live Substack Office Hours. Your Substack questions answered.Become a paid subscriber to Substack Writers at Work: www.writersatwork.net/subscribe.Yet another way SW@W is here to help you be your amazing self on Substack.Who?* Me, you, all of us.What?* Your Substack questions answered.When?* I’ll announce the day and time of each live Substack Office Hours every Tuesday in that week’s post.* We’ll also have popup Office Hours.Where?* You’ll be notified in email and the app when we’re live.* We’ll be live in the app.Why?* Imagine: Getting to ask me instead of the bot.* Imagine: No more confusion. No more frustration. No more feeling alone.* Office Hours are for paid subscribers.What are they like?* Watch the replay above to find out! (Great to listen to in the app or on Spotify or Apple. Timestamps are below.)* Basically, come on, be with each other, connect, put your questions in the chat, and I’ll try to get to each one.How?* Join us by upgrading to paid.Substack Office Hours, 11/8/24[00:04:17] Niches vs. being a generalist—my signature Substack DNA paradigm[00:07:35] Setting up subscriber challenges/workshops[00:09:33] Understanding the activity tab & metrics[00:14:18] Posting frequency - category differences & expectations[00:29:56] Balancing posts vs. notes - social media strategy[00:33:02] Monetization & subscription value[00:39:01] Headers, footers, and banners - design elements[00:42:02] Building audience—reality vs. perception[00:44:21] Custom domains and URLs[00:48:46] Selling/marketing without losing authenticity[00:51:31] Writing calls to action effectively[00:52:26] Community building among Substack Writers at Work subscribers 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

Hamish McKenzie, co-founder of Substack and author of "Insane Mode," reveals the platform's vision of prioritizing readers as customers rather than products. He discusses the journey from journalism to building a thriving community for creators, emphasizing the dangers of sensationalism in media. McKenzie highlights Substack's mission to cultivate trust-based relationships between writers and audiences, and explores integrating multimedia to enhance storytelling. His insights are invaluable for anyone looking to thrive as a writer or creative.