I feel a twinge of shame, guilt, and annoyance every time I see an Upgrade to Paid button on Substack. In a way, I already am “paying” for the content by subscribing and agreeing to receive it in my already-overstuffed inbox.

This dynamic feels fundamentally broken. Readers suffer through upsell after upsell. Creators not only wrestle with the vulnerability of sharing their work, but also with the discomfort of asking people to pay for it. And all the while, are unknowingly giving free subscribers a crappy experience.

“Upgrading” to paid

After a few of my posts on Twitter/X went unexpectedly viral, a friend nudged me to try Substack. I didn’t expect much, but it quickly became my favorite place to write. Over the last two years, my subscriber base has grown steadily, but slowly. Everywhere I looked, I kept seeing advice that enabling paid subscriptions was key to accelerating growth, so I turned it on.

Somewhat embarrassingly, I quickly ended up with a handful of paid subscribers who (with the exception of one devoted friend) I didn’t know. I hate asking people for money, so I felt an immediate obligation to make their paid subscriptions worthwhile.

I liked the idea of creating a small, inner circle where we could have an ongoing conversation — where I could learn what interested them and share raw, half-baked ideas.

But here’s where Substack fell short:

1. There weren’t great tools to help me build a paid subscriber community,

2. Enabling paid subscribers made the free subscriber experience worse.

Building a community

My first paid subscriber was a stranger, and I was dumfounded. Who was this person? What were they hoping for? I wanted to thank them and let them know I cared about make this a worthwhile experience.

As a few more people joined, I wanted to bring them together, express my gratitude, and learn more about them — the digital equivalent of taking them out for a beer.

But on Substack, my only options were:

• Create a post → Lives permanently on profile with a teaser visible to everyone

• Write a note → Visible to everyone on Substack in feed

• Start a chat → Can restrict to paid subscribers, but teaser is visible to everyone and it unexpectedly sends an email to all free subscribers.

None of these fit the bill. And when I started a chat with paid subscribers, Substack spammed the inboxes of my 2000+ free subscribers. 😬

That left me afraid to make a wrong move. So I just sent an email directly from Gmail. I have seen other creators go offsite with WhatsApp groups or Slack channels.

There is a big miss here for Substack to build tools that help creators engage segments of their audience and build community.

“Free” = Now with 80% more upsells

I am grateful every time someone willingly signs up to receive emails from me. A foundational law of any creator economy is that the majority of consumers will freeload — only a small percentage will ever pay.

So I was surprised that when I enabled paid subscriptions, it degraded the “free subscriber” experience. Suddenly, the free experience was littered with upsells and teasers at every turn.

As a creator, I did not intend to give free subscribers a crappy experience or make them feel guilty for not paying. Sure, these upsells may net more paid subscriptions, but they feel like ads or spam to 99% of readers.

I am confident there are better ways to build a loyal audience than through brute growth hacks.

Beyond brute growth hacks

Today, Substack feels like it prioritizes platform and subscriber growth over the user experience. But it’s possible to build a successful product without overt growth hacks. Here are some ideas for how to make Substack better for everyone:

Make Substack a destination.

Today, email and social media drive views. But Substack itself is totally under-leveraged as a distribution platform.

• Create a real feed. Show me new posts from publications I’ve subscribed to. Side note: I still can’t figure out what the homepage/feed of “notes” is supposed to be, but it’s not posts and not creators I’ve subscribed to.

• Guide me. At the end of a post, lead me to more posts from the same publication and/or related posts from other publications. Think YouTube’s “related videos” section.

• Boost discovery. Help viewers find new publications. What are the meaningful threads between posts or creators? Would a newspaper format work for the home page? Or a feed I can skim through?

Give creators more control.

• Make it clear what actions trigger what consequences. Sure there are preview tools for creators, but they don’t have the experience their viewers do. I’ve received too many messages from friends saying they were asked to upgrade, or couldn’t access content I assumed they could see.

• Respect the inbox. Never send email on a creator’s behalf without their explicit consent. Maybe even go as far as requiring a box to be checked before sending any email. And definitely do not send an email to all subscribers when a creator starts a chat with paid subscribers…

• Provide tools to customize content for different tiers of viewers. e.g., Button visibility could be conditional on viewer type:

  • Non-subscribers — I’m OK peppering you with subscribe buttons.

  • Free subscriber — I’m OK upselling you at the end, but please hide the interrupting “upgrade to paid” buttons throughout the post.

  • Paid subscribers — Hide all buttons and just say “thank you for your support” at the end.

• Support sharing drafts with anyone. If I am sending someone a draft for them to read before I post, they should be able to see it. Currently, having paid subscribers enabled unexpectedly restricts who can see drafts.

• Scan for low-quality experiences and warn me. Substack already provides warnings about missing buttons. Think beyond conversion to other unexpected poor experiences. e.g., “Are you sure you want to send this paid-only article to all subscribers? 99% of your viewers won’t be able to read it.”

Support community building.

• Make tools that help creators connect with subscribers. Do some user research — talk with creators and subscribers to understand what would make for a meaningful connection. Look at what the best community builders do on and off Substack. Turn those learnings into features.

• Build a place for private conversation. Think WhatsApp chats, Slack threads, Facebook groups. This is could be an evolution of the chat feature without the teasers.

• Give creators a place to share content with a small audience. Make it lightweight, impermanent, and unremarkable. Think a sketchbook or drafts folder.

There are so many more potential ideas. But they key is to think beyond short-term growth and instead thoughtfully shape the product around the needs, desires, and opportunities for creators and consumers.

Thank you!

I am grateful that Substack feels like a nice, quiet corner of the internet. But I’ve designed enough digital products to know it could be so much clearer, intuitive, and better for everyone.

I appreciate the 2000+ of you who subscribe to my content. It is not my intention to upsell you, and I am sorry that the interface makes it feel that way.

And to my handful of paid subscribers, I greatly appreciate your support. I am trying to make this a worthwhile, meaningful experience for you. Bear with me until I figure out how to invite you out for a digital beer!