The paywall is the problem: why Milo will always have a free core

Tonight I am a guest on WP Product Talk with Matt Cromwell and Zack Katz, and the topic is a question I have been chewing on for two years: can you monetize a WordPress plugin without paywalling the core?

I think you can. I think you should. And I have bet a product on it. Let me explain where that conviction comes from, because it did not appear out of nowhere.

Two front-row seats

I have spent most of my career watching plugin businesses from the inside.

I was the first person working at Easy Digital Downloads, back when Pippin Williamson was writing his income reports and inventing what we now call building in public. I saw what radical honesty does for a product: people do not just buy honest software, they root for it.

Then I spent 11 years at Automattic working on WooCommerce. I joined when we were 24 people. I left when we were two thousand. When you watch a product grow like that from the inside, you learn one lesson over and over: ecosystems beat features. Every single time. WooCommerce did not win because it had the most checkboxes on a comparison table. It won because the core was free, everywhere, and an entire economy grew on top of it.

What the standard model gets wrong

The default playbook for WordPress plugins is the feature paywall. Free version with the good parts removed, pro version that holds them hostage. It works, plenty of businesses live on it, and I have helped build some of them.

But it has a cost nobody puts on the pricing page. Every feature behind a paywall is a customer you taught to look for alternatives. The free user hits the wall, opens a new tab, and searches for whoever gives them that feature without the toll. You spent money acquiring that user and then handed them a reason to leave.

There is a subtler problem, and to be fair, it is not about greedy pricing. Take the official WooCommerce Subscriptions: a flat license fee per site, per year, honest and predictable. But a license fee is disconnected from the merchant's outcome: the store pays the same whether it thrives or struggles. And Automattic clearly sees it, because WooPayments earns on transactions, which is exactly the right direction. With Milo I simply went all the way: no license on the engine at all, and a transparent one percent on payments as the whole business model. When the only way you get paid is a slice of your merchants' revenue, every roadmap decision ends up pointing at a single question: what helps merchants sell more?

The bet we are making with Milo

Milo Subscriptions is our answer to that. The entire subscription engine is free on WordPress.org. Not freemium. Free. Recurring billing, renewals, trials, customer portal, the works. No seat limits, no feature gates, no pro version waiting in the shadows.

So where does the money come from? Two places, and we picked both on purpose.

First, payments. Milo Payments connects Stripe, PayPal, Mollie or Square in one click, and we take one percent on transactions. I love this model for one reason: we only make money when our merchants make money. Same side of the table. SaaS pricing charges you for existing. We charge you for succeeding. When a merchant leaves, most plugins lose a license. We lose a partner. That changes how you build, what you fix first, and who you answer to.

Second, optional add-ons. There are more than forty of them now: retention flows, box building and fulfillment, affiliates, compliance, all the things a growing subscription business eventually wants. The rule is simple and we never move it: the core does the job, the add-ons grow the business. Not one add-on holds the core hostage.

Early days

Milo is early. I am fine saying that. WooCommerce was 24 people once, and EDD was one developer with a blog.

Building the product turned out to be the easy half. The hard half is the one nobody sees coming: the most expensive part of software is not building it, it is being found. That is my work for the next two years, and I intend to do it the way Pippin taught me by example fifteen years ago: in the open, with real stories and real lessons, right here on this blog.

If you are curious what that looks like, stick around. And if you sell subscriptions on WordPress, the engine is free. Try it, and keep your two hundred dollars.

You can listen to the full conversation on WP Product Talk. Come argue with me, I answer every comment.