Guide for hosts
Masterminds and paid communities for retreat hosts
A retreat is one date with a hard deadline. Once it sells out, or once it happens, the relationship with that guest has nowhere to go until you announce the next one. A paid mastermind or community gives it somewhere to go, and gives you a second stream of income that doesn't depend on one week filling up. The two aren't the same thing, and knowing which one you're building changes how you price it and run it.
What's the difference between a mastermind and a paid community?
A mastermind is a small, closed group that meets on a set schedule to work through each member's specific goals. A paid community is a larger, more open room where people show up for connection, answers and each other, with less structure around any one person's problem. A mastermind of eight people might spend forty-five minutes on each person's week in turn. A community of eighty people is closer to an ongoing conversation you host, with office hours and a place to ask questions between them.
Retreat hosts tend to build communities more often than masterminds, because a community scales past the handful of people you can give real one-on-one time each week. A mastermind works when the members are similar enough that one person's problem is useful to the rest of the room. A general audience, with people at very different stages, usually does better in a community format.
Why would a retreat host build one?
Because it turns a one-time sale into a relationship you keep instead of one you rebuild from a cold list every launch. A member paying a smaller amount every month is worth less than one retreat seat on its own, but you keep that relationship month after month instead of starting over at zero before every trip.
It also solves a timing problem. Your retreat has a launch window and a sales window, and outside those windows there isn't much reason for a past guest or an interested stranger to keep paying attention to you. A community gives them a reason to stay in the room between retreats, which means your next launch goes to people who already know you, not to a cold list you have to warm up from scratch.
How is pricing a community different from pricing a retreat?
A retreat has one price per seat, paid once, for one trip. A community has a price per month, quarter or year that has to earn its keep every cycle, not just once. That changes what you're selling: a retreat sells an experience with a start and end date, while a community sells ongoing access, and the person paying for it is deciding, every renewal, whether this month was worth what last month cost.
The Hosting Guild's own community is one example, not a rule: $99 a month, $279 a quarter or $990 a year, with a founding rate of $49 a month locked in for anyone who joins before the end of 2026. That's our number, set for what we actually provide: weekly office hours with Anna, Stacy or me, and a growing library of resources. Your number depends on what you're giving people and how much of your own time it costs you per member, per month.
What does running one actually take, week to week?
Running a paid community breaks down to about four jobs, and none of them is optional for long. You need a live call on a cadence people can count on, so they know when to show up. You need a place for questions and conversation between calls, so the value doesn't only exist for an hour a week. You need something to seed the conversation when the room goes quiet, a prompt, a question, a piece of content, because an empty room is the fastest way to lose members. And you need to notice who's gone quiet and reach out, because a member who stops showing up is a member who's about to stop paying.
None of that is complicated, but all four take real time, week after week, the same way a retreat takes real planning before anyone arrives. A community that runs on good intentions instead of a schedule tends to fade within a few months.
What goes wrong when hosts try this?
The most common mistake is treating a paid community like a free Facebook group with a price tag on the door. A free group runs on whoever happens to show up that day. A paid one needs the same kind of structure a retreat needs: a schedule, a clear sense of what members get and when, and a host who shows up even on the weeks nobody feels like it. Members notice the difference between a room that's being run and a room that's just sitting there.
The second mistake is not setting a boundary on your own time before you launch. A community with no stated hours or response time quietly turns into a second full-time job, answering questions at all hours because someone asked. Decide ahead of time when you're in the room and when you're not, and say so plainly, the same way a retreat has a start time and an end time.
The third is pricing it like a retreat instead of pricing it like a subscription. A retreat guest decides once. A community member decides every renewal, so the price has to keep making sense month after month, not just on the day they signed up.
What keeps people paying month after month?
People renew when they can point to something specific they got that month, not when you've been generally encouraging. Showing up, answering an actual question with an actual answer, matters more than how warm the room feels. A community that tells members "that sounds great" every time helps nobody. A community that tells someone "your price is too low and here's why" gives them something to act on, and something worth paying for again.
Should a community replace your retreats, or run alongside them?
Usually alongside. A retreat and a community solve different problems: one gets you a concentrated week of income and a room full of people at once, the other gets you a steady, smaller amount of income and an ongoing relationship with people who may book your next retreat. Running one doesn't require giving up the other. A few hosts eventually shift most of their business toward the community and host fewer, larger retreats, but that usually comes after they've run several retreats and know their numbers well enough to make that call deliberately, not as a shortcut around the harder work of filling a room.
If you're weighing a community against turning what you teach into a structured course instead, those are different products built for different reasons; teaching into a course covers that choice directly. And running either one is still running a business, with its own pricing and its own break-even math, the same way starting a retreat business is.
Questions hosts ask
Do you need a course to build a paid community?
No. A course and a community are different products. You can build and run a paid community without ever selling a course. In the Guild, Anna's Profitable Retreat Method course lives inside the community as one part of what members get, not the reason the community exists.
How many members does a paid community need before it's worth running?
There's no fixed number that works for every host, because it depends on your price, your time and what you're actually providing each week. The right way to think about it is the same way you'd think about a retreat: what does it cost you in hours and money to run, and at what membership count does that cost clear? Work that math before you set a price, not after you've already launched.
Can you run a mastermind or community and still host retreats?
Yes, and plenty of hosts who build one do both. The community keeps past guests and interested strangers close between trips; the retreat gives them something concrete to book. Hosts who treat them as two parts of the same business, rather than a choice between them, tend to get more out of each one. If you're newer to hosting and still building the habits that make a retreat run well, becoming a better retreat host is worth reading alongside this one.