How to become a Substack Bestseller your way with Caroline Donahue and Stephanie Bennett Vogt

Busy?

Listen on the Substack Writers at Work podcast →→→→

Thank you

illyanna Maisonet

,

Petya K. Grady

,

Molly McPherson

,

Alyssa Polizzi

,

Amy Gabrielle

,

Simon Haisell

, and many others for tuning into my live video with

Caroline Donahue

and

Stephanie Bennett Vogt

!

Main takeaway: We have to ask people to pay. Yup. No way around it.

Some of us just expect people to pay. And writers and creators/creatives tend to dislike asking, but there’s no way around it.

I’ll be talking about how to ask people to pay without feeling icky and salesay 6/10 and in our paid-subscriber workshop on 6/13.

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Substacks mentioned and to subscribe to:

• Stephanie Bennett Vogt
  :
  The Journey Home

• Caroline Donahue
  :
  Book (& Craft) Alchemy

• Simon Haisell
  :
  Footnotes and Tangents

• haley larsen, phd
  :
  Closely Reading

• Meghan Daum
  :
  The Unspeakeasy with Meghan Daum

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3 Components of a Substack Bestseller:

1. Know what your Substack is (your Substack DNA)

2. Know what you offer

3. Articulate that offer to people

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Other people tell you how Substack works; I show you how to make Substack work for you. Become a paid subscriber.

What People Pay For:

• Accountability

• Community

• Fandom

• Solving a problem (including curation)

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Paid Strategies:

• Don’t auto-paywall your archive; instead, create a collection or “best of 2025” for paid subscribers by tagging certain posts and linking to the collection in your welcome email.

• Paywall intentionally. Insert paywalls strategically, link to paid posts in every free post.

• Offer challenges/workshops. Start free, then convert to paid.

• Build a larger business model. Use Substack as one part of multiple income streams.

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Three paid models:

• Paywall model

• Service/teaching model (workshops, challenges)

• NPR model (asking for support)

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Really important:

• Quality matters. High-quality content is everything for sustained growth.

• Keep it simple. Avoid overwhelm; do less but do it better.

• Be consistent. Pick a schedule you can maintain even on bad days.

• Think long-term. Building a bestselling Substack takes time.

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Common Mistakes:

• Offering too much

• Creating overly complex calendars

• Discounting too much and too often

• Not asking your subscribers to pay!!!

• Trying to do everything at once

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Time stamps:

Please check out and subscribe to

Caroline Donahue

and

Stephanie Bennett Vogt

. Their Substacks are terrific.

• 00:00:30 - Caroline's Substack

• 00:07:07 - Stephanie's Substack

Core Concepts

• 00:03:05 - 3 components of bestseller

• 00:21:05 - What people pay for

Paid Strategies

• 00:14:15 - Business models

• 00:19:04 - Paywalling tips

• 00:35:42 - 3 paid models

• 00:43:16 - Calls to action

• 00:45:37 - Discounts and special offers

• 00:52:54 - Nurturing subscribers

Sustainability

• 00:54:02 - Avoiding overwhelm

• 00:55:30 - Consistency

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For the comments: What’s worked for you in converting paid subscribers?