Substack Live Podcast

“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/

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/

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/

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.

Your behind-the-scenes look at what’s really happening and really working on Substack right now—with the platform’s leading Growth Strategist Sarah Fay.

Part 2 of the 2026 Pathway to Earning an Income on Substack

Okay, so I did some digging to see if there really is a crisis in paid subscriptions on Substack (and newsletters generally). ICYMI, someone wrote a viral article that stoked a lot of fear about the future of paid subscriptions on Substack.

The feelings are real—the worry—but the reality…might surprise you:

* It has always been hard to get paid subscribers.

* The rhetoric that Substack’s subscription model will never work has been around for half a decade, possibly since the platform’s inception in 2017. It might not, but the talk is nothing new.

* The data doesn’t support the idea that something has suddenly happened foretelling a grim reality and terrible future with paid subscriptions on Substack.

The worry just fosters assumptions that aren’t supported by the data:

* The economy is terrible, and people won’t pay.

* Subscription fatigue is driving a downturn in paid subscriptions.

* There’s a “subscription pie” we have to compete for a slice of.

* Bundling newsletters is the solution.

* Making Substack into a platform of Dollar Stores is the answer.

Today, I show you the flaws in these five (deadly) assumptions and five things you can do right now to be the one well-loved Substack people pay for.

SW@W homepage | Premier homepage | Substack Starter Pack | 24/7 Community Chat | Manage your subscription | Book a 3-Month Substack Growth Package 1:1

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.

“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

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

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.