What should an AI membership for small businesses include and cost?

Two paid tiers, roughly $400 and $1,000 a month, sitting on top of a free group. I sketched the tiers while advising someone building an AI service for home service businesses, and I've worked the same idea through for media operators and insurance agents. They're proposals, not prices I've sold at, so treat them as a starting point.

Who should the membership be for?

Small teams. Think four, eight or 12 employees: too small to hire an AI person at $150K, big enough to have real problems. Solo founders and husband-and-wife teams are much more price sensitive. I'd rather have the owner with at least six employees.

The same product can be $100 or $500 depending on who buys it. The $500 customers complain less. Less work, five times the money.

Pick a vertical niche, not a local one. A local group gives you a plumber, a roofer and an insurance guy who have nothing in common. A group of mortgage brokers or media operators all share the same needs, so one solution helps everybody.

Why does a membership beat one-on-one help?

Every business owner I talk to is confused about AI. Getting trained once doesn't solve it, because next month everything changed. What they want is a group they can lean on that's cheap enough and keeps them current.

It's a scale game. If you have 100 mortgage brokers, one expert can show all of them something that would be too hard for each of them to figure out alone. It's done with you, not done for you: you teach them, and you answer when they get stuck on a Meta ad or a creative.

"if this existed in insurance when I was in insurance, for $500 a month, you better damn believe I'd be in it."

What's in the free group?

Keep a free community free forever. It's the top of the funnel. Drop things there a little at a time, and use it to market the paid group: "we just did this in the paid group, want to jump over?" Your newsletter pitches the free group, and the free group sells the paid one.

What's in the $400 tier?

• Everything the team builds, shipped to every member: skills, plugins, workflows, ready-made ad creative and the Canva links
• A Slack or Discord where questions get answered
• Two group office-hours calls a month (I've also planned it as one guaranteed call a week, rotating between ad support, sales strategy and open office hours)
• Trainings and short async videos solving specific problems
• Discounts on custom builds
• Nothing one-to-one

Keep this tier strictly group.

What does the $1,000 tier add?

• A 90-minute call every month
• Extra office hours reserved for that tier
• A full audit every quarter

I'm working on the top end myself: an AI concierge at roughly $1,000 a month for ongoing access to me, aimed at owners with $1 million to $40 million in revenue. I think plenty of them would pay it. The problem is they don't know who I am, which is a distribution question. See how to find AI consulting clients.

Would a small business owner really pay $400 a month?

I would, absolutely, to have a go-to team for AI and support. Most people charge $400 an hour, and they won't be experts in your industry. Compare the membership to a consultant's hourly rate, not to software. That's one heavy AI user's willingness to pay, not a sales record, but it's the frame I'd use on the sales call.

The math doesn't need a huge crowd either. At $300 a month, a $30,000-a-month goal is 100 members.

Price per month	Members needed for $30K a month
$100	300
$300	100
$500	60

What if a peer already sells a cheaper community?

I hit this in media. A peer's community cost about $500 a year and, for the time being, was better than what I could offer on community alone. So I didn't compete on community. I bundled tools members would otherwise pay for, like Meta ad support plus a CRM and email setup that costs around $100 a month elsewhere, with no customization. That bundle alone felt worth $50 a month, which made $99 reasonable even at double the peer's price.

I didn't want to sell it for $30 either. If you're giving people real value, the goal is $100 to $200 a month per person over time.

What keeps members from churning?

Novelty won't. "Look at the cool new thing you can do this week" doesn't keep anyone for long. It has to be "look at the thing we just solved for you that saved you three hours" or saved you money. Cheap $10 memberships don't keep people in either.

Two more retention levers from my insurance plan:

• Owner group plus employee seats. Charge per employee, around $50 a month. The biggest risk of selling to owners is that they're too busy to deal with it. If their employees are in there, they're not going to bail.
• Partner with the niche's influencer. Offer 30% and free access for their whole team.

What does it look like inside one industry?

My "big bet" for independent insurance agencies, which I'm not pursuing myself because of focus: a higher-end group membership in the $500 to $1,000 range with office hours. You drop 10-minute videos, build them automations and drop them in, and jump on Thursday to walk through setup. The pitch writes itself:

"A fractional chief AI officer is $3,000 a month, hiring your own is $15,000, and you're at $700."

One warning: you have to know the problems to solve. Even with my insurance background, I don't know an independent agent's daily workflow. Whoever runs a vertical membership needs to come from inside that profession. More in AI for insurance agents.

Why a membership instead of done-for-you builds?

More on that choice in projects vs. memberships.