I sent my team a message today about AI and visibility. It felt important enough to post on LinkedIn, and important enough to expand on here.

The message was straightforward: the AI tools we’re integrating at Stranger Studios are giving Jason and me near-instant visibility into how work is getting done. Where processes are being followed. Where they’re breaking down. Who’s using AI tools and how.

I want to talk about what that means.

Because I don’t think most people outside of tech realize how quickly this is going to change every workplace.

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Most managed WordPress hosting is built for content sites. Pages, posts, media, maybe a contact form. The metrics they compete on reflect that: uptime percentages, monthly visit limits, concurrent users.

But if you’re running a membership site with recurring payments, gated content, member directories, and logged-in user sessions, those metrics don’t tell you much about how your host will actually perform when it matters.

In this post, I break down the most common managed hosting claims, explain why they fall short for membership sites, and give you a set of better questions to ask your current or future host.

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If you’re building a WordPress theme you plan to develop and maintain over time, whether it’s open source, freemium, or fully commercial, I don’t think a block theme is the right call.

Hybrid is the way to go.

Here’s why, and what nobody’s talking about when it comes to the real work of theming in the world of “The Block Editor” 2026.

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If you’re building a WordPress plugin… even a small one, especially a free one… these are things I wish someone had told me to set up from the very start.

None of them are hard. All of them compound.

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Which means all developers need to get a lot better at code review.

With tools like Claude, Copilot, and Cursor, we can generate massive amounts of code in very short periods of time. That’s both powerful and dangerous. More code means more opportunities for bugs, security holes, and tech debt.

So how do you get in front of this wave? Through the age old truth: the quality of the output is directly tied to the quality of the input.

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Paid Memberships Pro is not the “best” membership plugin.

And that’s fine. Because nothing is the best anything.

“Best” is a lazy word. It assumes your priorities are the same as everyone else’s. It assumes a listicle author getting paid $100 understands your business, your constraints, and your tradeoffs.

And honestly… do people even search like that anymore?

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The Lifecycle of Starting Something New™ (no matter how big or small it is)

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“The web looks different today.” That was a cancellation reason from an agency customer recently. At first I thought… what does that even mean? But the more I considered it, the more it’s been stuck in my head ever since. For years, our target buyer at PMPro was a developer helping someone without tech skills (more…)

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Up? Down? Flat? But compared to who? This is the first year at Paid Memberships Pro that we captured cross-team scorecard data in a real, consistent way. I plan to share our averages publicly in early 2026. A scorecard is great… at doing one thing: comparing this period’s metrics to historic metrics. Useful, but that (more…)

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With so many people saying AI site builders are going to eat WordPress’ lunch, I had to share my take. A lot of people are excited about using AI for website creation. If you’re in that camp, some part of you must buy into the idea that: That view assumes something I don’t think is (more…)

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