I Was Selling Hosting For $5 A Month

OK, this issue is a little different.

You may have gotten an email from me last week saying that Concierge prices are changing this Thursday. And I said that today I’d explain why.

So, that’s what this is. The main article is the story of how I figured out I’d been underpricing my own service for years… and how you can run the same check on whatever it is you sell. I think it’s worth your time even if you have zero interest in Concierge.

Then, down at the bottom, I lay out exactly what’s changing (and what isn’t).

Not every issue is going to be about my own stuff. 🤣 But this one is. Let’s get into it…

I Was Selling Hosting For $5 A Month

A few weeks back, I mentioned in the Inside Scoop that Concierge prices are going up on October 15th. I said I’d done “some real analysis” and pretty much left it at that.

So, here’s the analysis. Because the more I dug into it, the more I realized this isn’t really a story about Concierge. It’s a story about how easy it is to underprice your own stuff… and not even notice.

Core has been $99 for the longest time. Why $99? Honestly… because it ends in a 9 and it’s under a hundred bucks. That’s it. That was the whole strategy. 🤣 Color me brilliant. 😜

It’s that classic pricing psychology thing everybody does. It just felt better. I never had a shred of data behind it, and I hung onto that number way longer than I should have, purely because of how it felt.

And there’s a second thing going on here that I think a lot of you will recognize. I want to overdeliver. I want the offer to be so good it’s a no-brainer. So I kept adding to the plans… more plugins, better hosting, email delivery, analytics. The plans kept getting bigger. The price just sat there.

It’s a real easy trap to fall into. You want to make a great offer so badly that you end up underpricing yourself. Then you get busy taking care of clients and never look at the pricing again. That’s exactly what I did. I turned a blind eye to it, and those prices stayed put for far too long while the market moved around them.

So last month, I sat down with Claude and did what I should have done a long time ago. I looked at the market.

I had it pull the live pricing pages for 14 other companies that sell WordPress care plans or “personal” managed hosting. Agencies, creator-focused hosts, solo operators like me. What each tier costs. Whether hosting is included. How much hands-on time you get. What guarantees they offer. All of it lined up in one big comparison chart.

Two things jumped out…

First… my main plan was the cheapest one in the entire set for what it includes. Core is $99. That gets you hosting, a big library of premium plugins, and an actual person who knows your site. The closest comparable plans ran $159 to $179. And those didn’t even include hosting. Gosh what an eye opener that was! 🤯

Second (and this one stung a little)… my top plan was underwater. Platinum includes 3 hours of my hands-on time every month. At the rate Platinum clients pay for that time, those 3 hours are worth $294. Platinum costs $299.

Which means the hosting, the plugins, the email, the priority support… all of that was going for five bucks. 🤣

And once I could see where I actually stood, my attachment to $99 just… went away. It’s a lot easier to let go of a number when you can see it was never based on anything in the first place. Claude literally made me a scatterplot of the market, the price points… and the things that were included. And it was clear that I was an outlier… in the cheap way.

Now, a quick note on the AI part. Claude didn’t set my prices. What it did was the legwork I never would have made time for. It read all 14 pricing pages, lined them up, and wrote me a memo with a recommendation and the reasoning behind every number. I pushed back on a few things and made the final calls myself. But I was arguing with real data on the table instead of my gut.

Here’s what I took from it. And I think it applies to pretty much anything you sell…

• You can’t see your own pricing from the inside. You know what it costs you. You know how long it took to build. None of that is the market. Go look at what comparable offers actually charge. Use AI to get an outside perspective so you’re not stuck in your own tunnel vision.
• “Too cheap” is its own objection. I always figured a low price made the decision easier. But when a $99 plan includes that much, some people start wondering what the catch is. Cheap doesn’t always read as a deal. Sometimes it reads as “something’s missing.” In other words, pricing has a lot to do with positioning.
• If your time is in the offer, price the time. That’s the Platinum lesson. The moment you bundle hours into a package, do the math on what those hours are worth. Otherwise you might be giving away everything else.
• Price probably isn’t why people aren’t buying. This is a common mistake to make… to think lowering your prices will drive more sales. It is easy to think price is the main thing people pause on. But, it isn’t. The same people who complain about the price likely have multiple TV streaming services and use DoorDash every once in a while. 😇 The issue is usually your offer. It isn’t connecting, you’re not communicating it right, and they’re not resonating with your value proposition.
• Don’t punish the people who already said yes. Every existing client keeps their current rate, for as long as they stay. I thought about that one for about four seconds. A few extra bucks a month isn’t worth making a loyal client feel like they got billed for their loyalty. New prices are for new clients.

Here’s how you can do the same thing. You don’t need anything fancy.

1. Start with a list. A spreadsheet, a doc, whatever. Write down who sells something comparable to what you sell. 5 names is plenty. Just the names and their URLs.
2. Hand the list to AI and let it do the research. Tell it to go read each one’s sales page and pricing page, then report back in a table. What they charge. What’s included at each level. What guarantees they offer. That’s the part that used to take days… which is exactly why most of us never do it. I also had Claude run live searches and find others I may not have thought of.
3. Look past the price. This is where it got really useful for me. Have it look at what they bundle in. The hooks they lead with. How they describe the thing and who they say it’s for. Then ask what any of that means for your own offer. That’s how I noticed almost everybody in my space puts a named guarantee on the page. I didn’t. Now I do.
4. Ask it where you stand. This might be the most valuable part. You’re too close to your own offer. I certainly was. AI doesn’t care how long I’ve been charging $99 or how I feel about it. It looked at the chart and told me I was the outlier. Sometimes you need an outside set of eyes to point at the thing you’ve been quietly ignoring.
5. Then make it recurring. Most of the AI tools can run scheduled tasks now. So have it re-check your list every month and tell you what changed. New prices, new plans, a new angle on somebody’s sales page. You can even have it go searching for players you’ve never heard of and suggest adding them to the list. Now you’ve got a little market research department that runs on its own.

Oh, and one other thing. Use a GOOD model to do this. I did this right when Claude had released Fable 5.1. The model is expensive and it burns through your quota pretty quickly. But, this was during launch week so I figured I’d give it a go for something useful. For a lot of things, simpler cheaper AI models are the better go-to. But, for AI jobs where you’re actually going over pricing strategy? Use the top-shelf stuff.

Will this make me rich? Nope. I ran those numbers too, and it’s a modest bump. This is cleanup, not some grand strategy. But it’s cleanup I’d been walking past for a long time.

So if you sell a service, a membership, a course… anything with a price you set a while back… when’s the last time you actually checked it against the market?

Might be worth an afternoon.

WordPress News & Updates

WordPress 7.1.3 fixes seven security holes. It came out last Tuesday and most sites will have updated on their own by now. Worth a quick look at your dashboard to make sure yours did. It isn’t a drop-everything release, since most of the bugs need a logged-in user to pull off. The part I found interesting is who found them. Three of the seven were reported by Anthropic, and another by a security firm working with OpenAI. AI is now finding the bugs. The release notes.

WordPress wants the big companies to help pay for security. Automattic has paid every WordPress bug bounty since 2017. Now Mary Hubbard, the executive director of WordPress, has emailed the CEOs of more than 30 of the biggest companies in the space (GoDaddy, Elementor, Cloudflare and so on) asking them to chip in. The reason is right there in the item above. $90,000 went out to security researchers in the last three months, and nearly half of everything the program has ever paid out happened in a single quarter. When AI can hunt for bugs around the clock, the bill goes up. Most of the companies said they’re open to it but want specifics first. The Repository has the story.

A small win for Automattic in the WP Engine lawsuit. Last week I told you the case had gotten bigger. Now one piece of it has gone the other way. WP Engine wants Automattic and Matt Mullenweg sanctioned over messages it says were destroyed. The judge called Matt’s old post about using Signal with disappearing messages “admittedly problematic”… but said he isn’t seeing enough to call it destroying evidence, and that he’s leaning toward saying no. No official ruling yet. The hearing.

The founder of Rocket.net has left the company. Ben Gabler started Rocket.net and ran it for six years. A year ago it became part of hosting.com, and now he’s out. He’s still a big shareholder, says he isn’t riding off into the sunset, and plans to work on AI next. This one’s personal for me. A lot of my Concierge clients were hosted on Rocket.net for years before I moved everybody over to my own setup. It was a really good host under Ben. I’ll be curious to see what it looks like without him. His announcement.

Paste in a Wix or Squarespace address, get a WordPress site back. That’s liberate.sh, a new free tool from Automattic. Give it the address of a site on Wix, Squarespace, Shopify, Webflow or GoDaddy’s builder and it hands you a zip file with your pages, your images and a theme that carries the original look. They’re upfront that the copies aren’t perfect (complex layouts come back with gaps), and there’s a daily limit on how many sites it will do. But as a starting point for getting off a closed platform, it beats rebuilding from scratch. liberate.sh.

WordPress now has an official plugin for connecting AI to your site. It’s called the MCP Adapter, and it passed 40,000 installs in its first week on WordPress.org. MCP is the standard that lets tools like Claude and ChatGPT work with outside software. Just know what it is before you install it. It’s the plumbing. It doesn’t do anything on its own… it only lets your AI use whatever your other plugins have chosen to make available. You’ll need WordPress 6.9 or later. The plugin.

WordPress can now hand AI a clean copy of your content. The official AI plugin (version 1.4.0) has a new experiment called Markdown Feeds. Turn it on and your site gets a plain-text feed at /feed/markdown/, and any post or page can be pulled up the same way. The idea is that AI agents get your content without all the design code wrapped around it. Now, last week I shared a test showing agents mostly ignore this kind of thing and just read the regular page. So I wouldn’t rush out to set it up. But it tells you where WordPress itself thinks this is going. What’s new in 1.4.0.

Novamira adds a “Ghost Mode.” Novamira is the plugin that lets an AI agent work directly on a WordPress site, and it’s one I use. The new Ghost Mode is aimed at agencies. It hides Novamira from every administrator except the ones you pick… no menu item, no notices, no listing on the Plugins screen. So you can run it on a client’s site without it cluttering up their dashboard. They’re clear that this is NOT a security feature. Anybody who goes looking can still find it. It’s in the Pro version only. How it works.

SEOPress 10.3 lets you ask your AI to fix your SEO. SEOPress is the SEO plugin I use on my own site. The new version has a built-in connection for Claude, ChatGPT and Cursor, so you can say things like “list the pages with no meta description and write one for each.” It’s off by default, and there’s a read-only mode if you want the AI to look but not touch. The more practical fix for most people is the cookie banner. It used to misbehave with caching plugins, where one visitor’s consent choice could get saved and shown to everybody. That’s fixed. What’s in 10.3.

MemberPress gets a real shopping cart. The new Cart lets people buy several memberships or digital products in one go, and it’s included on every plan. There’s also a new Funnels add-on for order bumps, upsells and downsells after payment… but that one is only on their top Scale plan. Both are in beta, so I’d test on a staging site before turning it on for real customers. The announcement.

FluentCart 1.7.1 follows up fast on reviews. Right after shipping product reviews, they’ve made them work inside Divi and Bricks, with a bunch of layouts to choose from. They also added Airwallex as a payment option (a Pro add-on, and a popular request from store owners outside the US), and you can now set the name customers see at PayPal checkout so it shows your store instead of your legal business name. Release notes.

What’s Actually Changing With Concierge

So the first article above explains the “why.” Here’s the “what.”

When I first mentioned this a few weeks ago, I said the details were still being worked out. They’re worked out now. And it’s more than a price change, because I didn’t want to raise prices without also making the plans better.

The new prices:

• Essentials: $49 → $59
• Core: $99 → $119
• Pro: $199 → $229
• Platinum: $299 → $399

What’s been added to the plans:

• Private video hosting on Core and up, through Bunny.net, with your choice of Fluent Player or Presto Player. If you’re paying for Vimeo to host course or member videos, this replaces it. Keep in mind, this is mainly for people with a small set of videos where getting additional video hosting is a hassle. If you’ve got a large collection of members-only videos, I’d probably still recommend your own account so you control all of it.
• Bigger email allowances. 250 emails a month on Essentials, 2,000 on Core, 25,000 on Pro, and 100,000 on Platinum.
• Legal policies from Termageddon are now included on Pro, not just Platinum.
• Testimonial collection with Senja on Pro and Platinum. It’s the same tool I use on my own site, and it’s fantastic.
• A personal recommendation every month on Pro and Platinum. Not a status report… something I actually noticed on your site and think is worth doing next. This doesn’t exist yet, but will be built into a new reporting system I’m going to put together.
• A 30-day fit guarantee on every plan. If it isn’t working out in the first month, I refund it and move your site back wherever you want it.

What’s not changing:

• If you’re already a client, your rate. Not by a dollar, for as long as you stay on your plan. And you get everything above.
• The price of Anytime Credits.
• No contracts. Still month to month.

And the timing…

There’s no countdown clock on this. On Thursday morning, I’ll get into the office and change the prices. Anybody signed up before I do that keeps today’s rate for as long as they’re on the plan.

If you already know you want in, the plans are here.

If you’d rather talk it through first, book a Roadmap Call. As long as it’s on my calendar before Thursday, I’ll honor today’s rate… even if we don’t actually talk until a week or two later.

Fair warning… I’ll send two short emails about this on Tuesday and Wednesday. After that, I’m done talking about it and we’re back to our regular programming.