How to Raise Subscription Prices With Colin Devroe

Your readers are asking AI for the news instead of coming to your site. Every week, 10% of people get their news from AI, according to Reuters. For younger people, it’s 17%.A new Tow-Knight Center report, The Three-Layer Cake, says owning the reader relationship is one of the prizes of the AI age. It also argues that blocking AI hurts the public. Pete thinks those two ideas pull in opposite directions.So how do you let AI in and still keep your readers?Pete answers the questions publishers are asking right now:How do Google AI Overviews keep readers from reaching your site?What content can publishers create that AI can't replace?Should publishers license their content to AI companies?Should publishers block AI bots, and how do you keep your Google traffic?How does a registration wall build your email list?How should magazines set up a registration wall differently from news sites?Will AI agents replace your website visitors?You'll also hear how Mexico News Daily grew its traffic with a registration wall, and how your newsletter turns a growing email list into return visits with the Publisher Flywheel(TM).CHAPTERS 0:00 Who owns your readers: you or AI? 1:26 How many people use AI for news 1:54 How Google AI Overviews keep readers on Google 2:36 The Three-Layer Cake: content, AI bots, readers 3:11 Should you license content to AI? 3:35 Should publishers block AI bots? 4:26 Build your email list with a registration wall 6:49 Mexico News Daily registration wall results 7:03 Registration wall setup for magazines and niche publishers 8:07 When AI agents become your readersReady to grow your subscription revenue? Talk to the Leaky Paywall team: https://leakypaywall.com/ Learn more about paywall strategies: Publisher Revenue (link: https://publisherrevenue.com/)SOURCESTow-Knight Center for Journalism Futures, "The Three-Layer Cake: Public-Interest Information in an AI-Intermediated Age": http://www.journalism.cuny.edu/wp-content/uploads/2026/10/three-layer-cake-tow-knight-2026-10-21-final.pdfThe Decoder, "More people get news from AI chatbots, but trust remains low" (Reuters Institute Digital News Report 2026 data): https://the-decoder.com/more-people-get-news-from-ai-chatbots-but-trust-remains-low/Leaky Paywall, "How Mexico News Daily Built a 100% Reader Revenue Model (Without Ads)": https://leakypaywall.com/how-mexico-news-daily-built-a-100-reader-revenue-model-without-ads/

A business journal in Youngstown, Ohio raised its subscription price from $25 to $99 a year. Nobody canceled.Should you raise yours? Colin Devroe, co-founder of Good Migrations and head of AI at NerdPress, has spent 10 years moving Stripe subscriptions and running price increases, and most of the publishers he sees charge too little.So how do you raise it without spooking your readers?Pete and Colin answer the questions publishers ask before a price increase:- Which price bucket are you in, and how far can you move inside it?- Should you raise prices once, or a little every year?- What happens if you stop offering your lowest tier?- Does a free trial tell readers your content isn't worth paying for?- What should the price increase email say, and what should it never say?- Which Stripe setting can tell your subscribers before you do?You'll also hear why billing 1,000 subscribers monthly means paying card fees 12,000 times a year, and the pricing page default that fixes it, plus the three-card layout Pete would use and why your higher tiers churn less than your cheapest one.And if AI is pulling content from your site, Colin covers paywalls for agents, MCP servers and whether bots will ever pay what readers do.CHAPTERS0:00 Raising a subscription price from $25 to $990:27 Meet Colin Devroe of Good Migrations and NerdPress2:19 How Good Migrations started with Stripe migrations6:14 What a messy Stripe account looks like9:44 How to price a new paywall11:59 Subscription price buckets: $4.99, $9.99, $19.9913:42 Raise prices a little every year17:25 Raise your lowest tier to move readers up18:52 Monthly vs annual subscriptions20:53 Why your pricing page should default to annual24:02 Free trials vs charging from day one25:20 Registration walls and annual-only plans29:14 How much churn after a price increase33:25 Registration wall first, then three pricing cards35:14 AI bots, MCP servers and paywalls for agents41:40 How food bloggers are handling AI45:40 Will ad revenue survive AI?48:02 DIY price increases in Stripe: what goes wrong49:51 How to tell subscribers about a price increase52:24 Crowdfunding an investigative story53:49 Where to find ColinReady to grow your subscription revenue? Talk to the Leaky Paywall team: https://leakypaywall.com/Learn more about paywall strategies: Publisher Revenue https://publisherrevenue.com/ SOURCES- Good Migrations, Colin Devroe's Stripe migration and price increase service https://good-migrations.com - Good Migrations, "Need to move quickly? Helpful tips to speed up your Stripe migration" https://good-migrations.com/2025-fast-migration/ - NerdPress, where Colin is head of AI: www.nerdpress.net 

Politico is putting its free content behind a registration wall, and readers will pay with an email address. Here's why your site should do the same.Pete starts with a Nieman Lab report from the Future of Media Technology conference about Politico’s plan to require free registration. He has helped hundreds of publishers set up registration walls, and he walks through the 5 benefits they see: email list growth, a stronger newsletter, engagement data, advertising growth and AI defense. He also covers two 23-year-olds who built Argentina’s top news app by scraping publisher headlines into an AI audio briefing, and what that means for your content.What You’ll LearnHow a registration wall works as a paywall that readers pay with an email addressWhy registration walls get 2x to 7x more email signups than newsletter pop-ups and opt-in formsWhy your newsletter should be one of your main products, the way the paper used to show up on the drivewayHow logged-in readers show you who is engaged and who is likely to upgradeHow to target your most engaged free readers with offers no one else seesWhy advertisers pay more for a large, targeted email listHow AI apps and local newsletter startups are repackaging publishers’ headlinesHow a registration wall can block AI bots from scraping your contentWhy AI licensing pays pennies to small and mid-sized publishers, and why your own audience matters more

The New York Times flagged a paying subscriber’s account for using too many devices.In this episode, Pete shares what happened when he clicked a link on LinkedIn, opened it in the app’s built-in browser, and got asked to verify his $30-a-month NYT account. He uses that moment to answer a question publishers ask often: should you limit password sharing? He explains when locking things down makes sense, why most sites should keep login limits generous, and how to turn shared logins into extra revenue with a family plan.What You’ll LearnWhy in-app browsers on LinkedIn, Facebook, and other social apps count as a new device and can set off login limitsWhat a typical shared household looks like: two people, about three logged-in sessionsHow WordPress concurrent login plugins track one account across browsers and devicesWhy a generous limit of four or five devices keeps honest subscribers happyWhat happens when limits get too strict: more support tickets and more login frictionWhy B2B publishers may need tighter controls so one login doesn’t spread across a whole companyWhen a hard paywall makes sense, such as for financial publishersHow a family plan turns password sharing into an upgrade opportunityWhy family plans convert: subscribers often add a partner for a little more money

Nobody wants to buy "unlimited access." In this episode, Pete reviews the Mexico News Daily subscription page and shows how to sell benefits instead, write that copy with AI, and set up a distraction-free page with pricing cards that convert.What You'll LearnWhy "unlimited access" doesn't sell subscriptions. Readers pay for what your reporting does for them: where to eat, how to vote, how to feel like a local.How Mexico News Daily grew from about half a million monthly readers to over 2 million in two years, with a registration wall feeding its newsletter.The 10-second test for your subscribe page: can a reader see how their life gets better if they pay?How The Atlantic sells a benefit in one headline: "Journalism that explains America and the World."Why your subscribe page should have no distractions. That means no menu, no ads and no outbound links. Just a benefit headline, a line of copy and your pricing cards.How to write benefit copy from your About or Mission page with Claude or ChatGPT, using the StoryBrand framework (your reader is the hero and your publication is the guide).A three-card layout that works: an individual plan with a monthly/annual toggle, a family plan, and gift subscriptions.The Mexico News Daily family plan: three seats for $15.99, compared with $8.99 for one, and it is converting.Why gifts matter. Print magazines often get about 20% of revenue from gift subscriptions, and 5-10% from digital gifts is realistic.Adding a fourth, full-width card for group access: schools, libraries, government offices and even coffee shops.Using FAQs and contact options at the bottom of the page to answer last-minute questions, as the Civil War Monitor does.How a single line of subscription copy on North Shore magazine's login page became one of its top sources of paid conversions.Putting benefit-driven upgrade promos at the top and bottom of every free newsletter.Resources MentionedMexico News Daily: the publication torn down in this episodeLeaky Paywall List Builder: registration wall for building your free email listLeaky Paywall Group Subscriptions: the extension behind Mexico News Daily's family planNorth Shore magazine: case study on subscription messaging on the login pageClaude / ChatGPT: AI tools used to turn an About page into benefit copyContact: [email protected]

Episode SummaryIn this episode, Pete and Tyler compare a decade of print publisher stories, starting with a recent closure that came down to debt from an old acquisition, not readers.They walk through three publishers who each handled the print decision differently: Brew Your Own and Winemaker, Track & Field News, and My Villager. Then they get into the fix that matters most once print goes away, the registration wall, and why your print archive belongs on the web as real HTML, not a flipbook.What You'll LearnOne or two local newspapers close in the US every week. The closure Pete and Tyler discuss this episode came down to debt from an old acquisition, not a lack of readers.Public notices (probate filings, court orders, anything states mandate be published) are why a lot of small papers still print. Qualifying takes twelve straight months of print publication, and the rules differ by state.The New York Times' circulation is about 4% print today. That 4% is loyal and pays well for it, which is a big part of why the print edition still makes sense.Print isn't winning new subscribers anywhere Pete and Tyler have seen. It retains an aging base while digital is where the growth happens.Design-driven, lean-back magazines (fishing, boating, hobbyist niches) can make print the actual product. Transactional, lean-in news content generally can't.Brew Your Own and Winemaker went cold turkey on print and rebuilt their readership within a year.Track & Field News dropped print for nine months, lost half its older readers who wouldn't log in, then relaunched print-on-demand at close to five times the original price.My Villager flipped its free weekly in Saint Paul to paid print and paid digital and grew from there.The registration wall converts 2x to 7x more email signups than a standard newsletter opt-in (3.2 to 6.7% versus 0.9%, across nine publishers on the same tool).Get your print archive onto the web as real HTML articles, not flipbooks. Modern Drummer doubled its site traffic in a year just by publishing one new issue and one archive issue online each month.Resources MentionedLeaky Paywall: publisher's AI survival guide, referenced for the registration wall and email growth numbersPublisher's AI Survival Guide: the free 65-page guide Pete mentions on the show, pops up on the Leaky Paywall homepageReissue: turns print PDF archives into web-ready WordPress postsReal 3D Flipbook: the WordPress plugin Pete and Tyler recommend for digital flipbook editions

A publisher with 10% monthly churn loses 70% of its subscribers in a year.In this episode, Pete sits down with Tyler from Newsletter Glue to break down subscriber churn, and where it actually starts. Tyler shares a real case: a publisher with a large subscriber base that grew for six years, then plateaued and started sliding. The cause wasn't pricing or content. They had never sent a single newsletter, not once, in six years.Newsletter engagement is one of the strongest predictors of retention. Subscribers who open newsletters regularly are about twice as likely to still be subscribed 12 months later. Pete lays out six concrete moves publishers can make to close the gap: drip campaigns for niche and news publishers, tracking quiet subscribers, fixing involuntary churn from failed payments, smarter cancel flows, cutting login friction, and pricing levers that reduce renewal pain points.What you'll learn:Why involuntary churn (failed payments) accounts for 20-40% of all churn, and how Stripe's payment intents plus services like ChurnBuster can cut it by 40% or moreHow The Moss Report's 18-email drip series onboards new readers like a course, and how the Wall Street Journal targets 100 days of engagementWhy niche publishers should package a drip series (not a single newsletter), while news publishers should build habit and routine around a fixed send timeHow personalization, like Mexico News Daily's opt-in regional editions, drives the highest engagement ratesWhy tracking "quiet" paid subscribers lets you intervene before they churn, and why archive content often outperforms fresh contentWhy the cancel flow matters: offering pauses, discounts, or downgrades before a subscriber leavesHow removing login friction with automatic login (Flowletter + Newsletter Glue) reduces support tickets and churnWhy monthly vs. annual pricing changes your churn exposure, and how tiered "good, better, best" plans give you a downgrade path instead of a cancellationResources mentioned:Leaky Paywall: leakypaywall.comNewsletter Glue: newsletterglue.comFlowletter: leakypaywall.com/flowletterList Builder: leakypaywall.com/list-builderLeaky Paywall Insights: insights.leakypaywall.comThe Publisher's AI Survival Guide (free): publisherrevenue.com/tool/the-publishers-ai-survival-guide/The Moss Report: themossreport.comMexico News Daily: mexiconewsdaily.comChurnBuster: churnbuster.io

Google traffic to publishers is down over 30%. AI Overviews are answering the questions your articles used to. Social referral is a shadow of what it was.The one thing nobody can scrape from you is a direct relationship with your audience. This episode walks through the Publisher Flywheel: a 4-step system Pete has built with hundreds of publishers to convert anonymous traffic into known, engaged readers, and turn that audience into revenue.You'll see it working live on The Spanish Eye, a regional English-language news publisher in Andalusia that grew active users 800% in 12 months. Pete breaks down exactly which levers they pulled, in what order, and how you can start with a loose registration wall and tighten over time as confidence builds.What you'll learn:Why the average site sees 1.7 pages per session, and what that means for where your registration wall has to sitHow registration walls convert anonymous traffic 2-7x faster than pop-upsThe two-newsletter setup (free list + paid list) and what each one is actually forWhy your newsletter is a product, not a promo channel, and the cadence that actually convertsHow to target logged-in free readers with the right upgrade message at the right momentThe insights that matter: paywall hits, quiet readers, failed payments, and how to automate follow-upWhen (and whether) to lock down completely against AI bots and searchResources mentioned:The Publisher's AI Survival Guide (free): publisherrevenue.comThe Spanish Eye: thespanisheye.comLeaky Paywall: leakypaywall.com/list-builder/List Builder: leakypaywall.comLeaky Paywall Insights: insights.leakypaywall.com

A local news publisher with no paid paywall is still pulling reader revenue, and it's working.In this episode, Pete and Tyler break down an incognito digital-only publisher (about 60k monthly visitors, per Similar Web) running a model that ignores the usual playbook. There's no hard wall on the content. Everything stays free to read after a generous registration step, and the paid upgrades come from community perks instead of locked articles.If you've been nervous that putting up any kind of wall will tank your traffic, this one's a useful counter-example. It shows how to capture emails, build confidence with a wall, and turn free registered readers into paying members.Key TakeawaysThe generous registration wall. Readers get 3 free articles off the street. On the 4th view, a free registration wall unlocks unlimited access. That setup is hitting a 5.7% conversion rate against wall views and brought in 2,200+ registered readers in about 3 months, which Tyler says is far beyond what their old sidebar email widget ever did. The plan is to tighten the wall to two or one free article over time, and Tyler thinks conversion could roughly double when they do.Move commenting off Facebook. Tyler's take: turn off comments on your Facebook page and pull the conversation back to your own site. Gating comments behind registration (or paid membership) keeps the discussion clean and easy to moderate, since people with their name and payment details attached tend to behave. You also keep the eyeballs on your site instead of handing them to social.Levers for paid upgrades beyond content. Since articles are free after registering, paid upgrades run on membership perks: on-site commenting, an ad-free experience, a physical welcome gift (a hat or bag), discounted tickets to events held a few times a year, and a subscriber-only newsletter. Paid subscribers can also email questions directly to the editorial staff.The pay-what-you-can option. Below the main pricing cards sits a small donation option for readers who want to support local journalism but won't commit to full-price membership. Tyler says a measurable number of people take it, spending $5 to $9 who'd otherwise have spent nothing.The text-only editorial newsletter. No images, no standard teasers. It reads like a personal note from the editor, with article links woven into the writing and a support CTA at the bottom. Pete also flags the reply-to-the-editor angle: when readers actually hit reply, Gmail reads that engagement as a quality signal and is less likely to bury your newsletter.Learn more about our paywall strategies: https://leakypaywall.com/ 

In this episode of The Paywall Podcast, Pete sits down with James Baldacchino, fractional CMO of Leaky Paywall and AI SEO specialist at Ellipsis, to break down what publishers need to do as AI reshapes search and reader revenue: how to optimize your content for LLMs like ChatGPT, Claude, and Gemini, why most publishers underprice their content and how to run a silent price test that lifts revenue without spooking subscribers, plus a live teardown of a high-traffic B2B publication that exposes the exact paywall friction points costing publishers paid conversions.🔑 What you'll learn in this episode:• The New AI Search Game: Shifting from legacy SEO to AEO and making your unique content extractable for AI bots.• The 6-Month Pricing Rule: Why static subscription prices signal low quality, and how to test higher rates without triggering churn.• The Database Monetization Strategy: How to turn your historical content archives into hyper-focused, premium data assets readers will gladly pay for.• Frictionless Conversion Funnels: Why hard paywalls fail, the power of a free registration wall, and how to spot conversion killers on your checkout page.🔥 Learn more about our paywall strategies: https://leakypaywall.com/Connect with James Baldacino & Ellipsis:📩 [email protected]🌐 https://getellipsis.com/