Paywalls get a bad rap.

When the internet started, it was “free” and everything on it was “free.” Over time, those of us who make the internet (me as a former software designer and you as a journalist) realized that it’s actually a full time job to produce this stuff.

Full time jobs need to be paid, and if you don’t want to subsidize your internet income with defense contracts like Musk, Altman, Bezos and Zuckerberg, then you may turn to your readers to keep your work independent.

Wait, but Lex, won’t readers pay for my reporting just because it’s good?

Maybe. There are journalists who make a full time living without a paywall. Matt Kiser, Andy Dehnart and Judd Legum come to mind as examples of that. 

But you will absolutely make more money with a paywall. 

Lucky for you, you’re in great company with some of the best reporters on the internet who are paywalling to STAY independent.

I asked 5 popular publishers how they choose what to paywall. Find their answers in today’s issue!

P.S. This topic was suggested to me by Rose Thomas Bannister and by Ryan Teague Beckwith. Ryan is writing a piece on HOW to paywall, meaning where do you break your story and how do you entice readers to actually pay for it. Get on his “Your First Byline” mailing list and stay tuned for more intel on paywall practices!

What should you paywall

No journalist wants to paywall just like no landlord wants to charge you for the roof over the head that ensures your survival.

Ok, bad analogy.

My point is that, of course, it would be great if access to journalism was free. It’s not. When we pretended it was free by selling our souls to the defense contractor private equity ghoul brigade, that was worse. We see that pretty clearly now that one of them is running the government unelected, and most importantly, our readers do too.

It’s never been a better time to paywall.

But how do publishers choose WHAT to put behind the wall? I asked Matt Brown, Caitlin Dewey, Jason Koebler, Max Read and the founders of The Flytrap for their logic.

Paywall the niche reporting

Matt Brown from Extra Points

Beat: The business behind college sports 
Paid subscribers get: 2 extra paid subscriber only posts per week, access to Athletic Director Simulator 4000 (a custom game), and a free ebook.
Publishing frequency: 4x a week (2 free, 2 paid)
See the tiers: https://www.extrapointsmb.com/upgrade

What I noticed about Matt’s paywall strategy:
Matt publishing things like the “State of Extra Points” (behind the scenes) and mailbag posts (questions from readers) on the free side. Those types of posts tend to be more frequently paywalled elsewhere.

Extra Points is 4+ years old with 2k+ paying subscribers so Matt knows by now who his paying readers are and what they care about. His paying readers are more industry pros, like the athletic directors and vendors themselves, along with some megafans of insider sportsball. So he paywalls things like a deep dive into what IRS data says about college sports fundraising and a guest post from a cybercrimes guy on college sports betting.

What Matt said about his paywall strategy:
“It's more of an art than a science” - Matt Brown, Extra Points

• The “hard reporting” goes behind a paywall.

• The “more niche and specialized” a story is, the more likely it goes out just to the paid fanbase.

• The mainstream, bigger audience stuff is free.

Paywall the extra treats

Caitlin Dewey from Links I Would GChat You If We Were Friends

Beat: Internet culture
Paid subscribers get: Subscriber only book and TV recommendations, free gift links to linked articles in other publications, a sticker and note, early access to latebreaking Links stuff and a free “mysterious” link on their birthday.
Publishing frequency: 2x a week (with paid subscribers getting bonuses inside those)
See the tiers: https://linksiwouldgchatyou.substack.com/subscribe

What I noticed about Caitlin’s paywall strategy:
Caitlin positions her paywall more like close friends (to borrow that term from the Insta-verse) so paid readers get little extra treats like “a very chaotic photo of my dog” and “unsolicited commentary on years-old seasons of Great British Bake Off.” 

You can read most of what Caitlin writes for free, but if you really like her takes, you’re going to want to pay to access to her most “chaotic” and “unsolicited” stuff.

What Caitlin said about her paywall strategy:
“I try to paywall as little as humanly possible” - Caitlin Dewey, Links I Would GChat You If We Were Friends

• Only one post has ever been fully paywalled because it included vulnerable personal info

• Caitlin sees her free list growth as important for “the long-term health of my business.”

• Most of the paywalled stuff is aimed at the “most loyal and engaged readers.”

Paywall the behind the scenes

Jason Koebler from 404 Media

Beat: Tech reporting
Paid subscribers get: Unlimited articles, ad free reading, ad free podcast, commenting, RSS, access to “Behind the Blog,” access to the “404 FOIA Forum”—a community around public records.
Publishing frequency: Multiple times a day
See the tiers: https://www.404media.co/

What I noticed about 404 Media’s paywall strategy:
It’s the total opposite of the Extra Points strategy. 404 paywalls the behind the scenes content about their own business and stuff like the FOIA Forum where they teach you how to file public records requests. 

My bet is that a lot of 404 Media’s paid subscribers are other journalists, writers and tech nerds—more peers than consumers or maybe prosumers—so these perks offer them a different side to the reporting than would normally be shown on any news site. And it’s working for them, they reported over 6k+ paying subscribers last September (undoubtedly, much higher than that now).

What Jason said about their paywall strategy:
“We have had a lot of back-and-forth among ourselves about what to paywall, when, and why, and we have tried our best to keep as much of our reporting free and available to as many people as possible, while balancing the fact that in order for the business and ourselves to survive, we need people to subscribe. It's a constant balancing act and there's no perfect science to it.” - Jason Koebler, 404 Media

• Behind the Blog was an early decision that the team wanted to include for “extra value.”

• The “less formal” and “more direct” conversations that the 404 team has are part of Behind the Blog.

• While how to file public records is a paid perk, the public records themselves and related reporting that 404 Media unearths are public: “Anything we report with public records we've obtained, we try to post those records and keep the article unlocked for everyone as a service.”

The 404 Media team has also talked on their podcast about a delayed paywall where some stories are public when they’re first reported and a paywall is added later on once the news cycle has died down in a week or two.

Paywall your recommendations

Max Read from Read Max

Beat: Tech, politics, culture and media
Paid subscribers get: 2 newsletters/week, a weekly roundup of recommendations for links, movies and books, access to explainers on relevant topics, and merch (sometimes).
Publishing frequency: 2x/week
See the tiers: https://maxread.substack.com/about

What I noticed about Max’s paywall strategy:
Max is paywalling his taste which reminds me of Caitlin’s strategy. The weekly roundups are for paid subscribers only and each one is a different mix of surprise picks.

It’s possible that Max leaning into the “1000 true fans” of it all is working (though he’s at more than double that in terms of paying subscribers—2600+ as of a few months ago) but I would also venture to say that these round up posts ALSO serve as an effective reminder that you, his reader, are “freeloading” on the list and that Max needs your paid support.

Meaning that it’s possible that readers want access to the roundups OR it’s possible that the roundups remind readers how much they like Max and want to pay him.

What Max said about his paywall strategy:
Max pointed me to his “How to Substack” post from last fall when I asked about his strategy which includes the following insights:

• Max thinks it’s easier to convert readers from free to paid if they get “something specific” rather than just supporting the publication (Have to agree there!)

• The paywalled posts include “some kind of value-add (shopping guides, book recommendations, link roundups).”

Paywall because that’s how you stay independent

The Flytrap 

Beat: Culture, politics and current events from an intersectional feminist team
Paid subscribers get: Unlimited article access, comments (at higher tiers), early and enhanced access to events, “Your Name in the Garden of Infamy” (highest tier), free gift subscription for a friend (highest tier).
Publishing frequency: Multiple times a week
See the tiers: https://theflytrap.beehiiv.com/upgrade

What I noticed about The Flytrap’s paywall strategy:
The Flytrap just launched a few months ago, so it’s hard to spot a paywall pattern yet, and they laid out a pretty clear strategy in their note to me which was beautifully written. I’m sharing it in its entirety below. They are not paywalling most content right now, but in their note, they say that they plan to.

I strongly support this strategy, I love their point about a “tasty sample” and I share the thinking that how you paywall matters as much, if not more, than what you paywall.

What The Flytrap’s cofounders said about their paywall strategy:
“The Flytrap’s decision to paywall most of our content lies in our founders’ belief that the solution to the current fascist-enabling media landscape is worker-owned independent media outlets. The legacy media outlets we're competing with are still corporate juggernauts with huge reader bases (even if they're shedding some subscribers). Worker-owned independent media outlets are the David to that Goliath.

We have veterans in our ranks that have experience keeping independent media alive without paywalls. Because of that, we know how difficult it is to build a sustainable independent media business without a paywall. If we can't ultimately run a sustainable business, we can't keep doing our essential work, and we no longer believe that is possible without subscriber revenue. One of our co-founders, Evette Dionne, who previously worked as editor-in-chief of Bitch Media, wrote a great explainer of how challenging running a feminist publication is here. Readers are going to have to be willing to pay if they want this kind of content to exist, and we think many readers are waking up to that fact and putting their money where their mouths are. So far, our determination to paywall most of our content seems to bear this out—our subscriber numbers are going up, and we hear often from our readers that they are proud to support our work and other indie outlets like us.

We also recognize the value of a tasty sample. Once a month, we provide a free post—usually one touching upon a current topic of robust online discussion—to give potential subscribers a sample of what they get with a Flytrap membership. Posts with critically-needed resources are always free to stress that a paywall shouldn't block access to information. We’ve also had numerous Residents of the Bog subscribers (our premium tier) donate the gift subscription that’s included in their membership to a shared pool, from which we’re able to offer comped subscriptions for folks who wouldn’t otherwise be able to afford it.”

Well, there you have it. Do not be afraid to paywall because the alternative might just be that there’s nothing to paywall.

As for what to paywall, try on the strategies above and see how they suit your publication. Know that your readers are likely more flexible than you think they are and keep your decision logic straight forward if you’re just starting to paywall your content.