Paywall Podcast - Subscription strategies for news and magazine publishers

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.

CHAPTERS

0:00 Raising a subscription price from $25 to $99

0:27 Meet Colin Devroe of Good Migrations and NerdPress

2:19 How Good Migrations started with Stripe migrations

6:14 What a messy Stripe account looks like

9:44 How to price a new paywall

11:59 Subscription price buckets: $4.99, $9.99, $19.99

13:42 Raise prices a little every year

17:25 Raise your lowest tier to move readers up

18:52 Monthly vs annual subscriptions

20:53 Why your pricing page should default to annual

24:02 Free trials vs charging from day one

25:20 Registration walls and annual-only plans

29:14 How much churn after a price increase

33:25 Registration wall first, then three pricing cards

35:14 AI bots, MCP servers and paywalls for agents

41:40 How food bloggers are handling AI

45:40 Will ad revenue survive AI?

48:02 DIY price increases in Stripe: what goes wrong

49:51 How to tell subscribers about a price increase

52:24 Crowdfunding an investigative story

53:49 Where to find Colin

Ready 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