The Hosting Guild

For the people who have to fill the seats.

One of us gets you discovered. One of us gets you booked. One of us delivers the week.

A women’s reset in Costa Rica, a writing week in Michigan, twelve people going to the Indy 500, a lakehouse with dates to fill — underneath, it’s one job. A fixed number of seats, a fixed date, and a deadline that doesn’t move.

If somebody has to fill those seats, and that somebody is you, this is for you — whether the room is one you booked or one you own.

A retreat business and a group travel business are the same business underneath: you build the trip, you own the audience, and nobody else is going to fill it.

The Guild is where that craft gets taught, year round, by three people who fill retreats, trips, and workshops for a living.

Join the Guild — $9/mo See what’s inside

A group seated in a circle in a bright lakehouse living room, flip charts and sticky notes covering the wall behind a woman presenting. — The Residency at Lakemore — the Guild’s five days in person.

You were taught to run the week. Nobody taught you to run the company.

We teach you to run a business, not just a retreat. The bookkeeping that survives a tax year. A P&L that holds up at half capacity. What to get in writing before the venue falls through. Where your unpaid hours actually go, and how to price them in.

Because empty seats are what close these businesses — not bad experiences. Maybe you already know how to run a beautiful week. It’s everything before it that breaks you: being found, being believed, being booked, usually at the kitchen table at eleven at night with a deposit already spent.

That’s the part we teach. And in January, it’s the part we sit down and do with you.

A woman working on a laptop at an outdoor table beside a lake, wrapped up against the cold. — The part nobody photographs: the laptop, the deadline, and the seats that haven’t sold yet.

The word was deliberate

Why a guild, and not a course.

A guild was a group of people doing the same difficult craft in the same town. They set the standard, they trained whoever came up next, and they carried each other through the bad years. Nobody graduated from a guild. You belonged to one, and you got better inside it.

That is the shape this work actually has. Filling a room is not a thing you learn once and then know. Every experience you host is a new date, a new audience, a new deadline that will not move — and the fix for the thing that went wrong last time only shows up when you try again.

Courses end at the part where the work starts. Communities are pleasant and mostly do nothing. We wanted the third thing — a room with actual craft in it, where whoever answers you on Thursday has sold the exact thing you’re trying to sell, and has the scars to prove the first few didn’t go well either.

So: a guild. A hall you can walk into year round, a standard we hold ourselves to in public, and the weeks each year when everyone is in the same building.

A course is one pass through the loop. The Guild is the loop, running.

You don’t graduate. You belong.

What you join

Four things, from the day you walk in.

Nothing is drip-fed and nothing is locked behind a longer subscription. Two of these come with The Community at $19; all four come with The School at $99, and the whole library opens on day one.

Both tiers

The people

Other hosts who are mid-launch right now, in the Hall — not an archive of people who finished years ago. This is the part a course can’t give you.

The School · recordings in The Community

Weekly office hours

Every week, live, with Anna, Stacy or Robert. Bring the thing you’re stuck on. Someone who has sold the same thing tells you what’s wrong with it.

The School · first two shelves in The Community

The Library — 115+ resources

Eleven shelves of it, and more added constantly — plus the video courses, the first of them Anna’s full Profitable Retreat Method, a $899 course included in The School, and we’re adding new ones continuously. All of it opens the day you join. Nothing drips.

The School

The lowest listing commission there is

Publish what you’re hosting and keep 95% of every booking — or all of it, forever, if you join as a founding member. No tracking redirect, no exceptions, no cut on the seats you filled yourself.

$19 a month for the community. $99 for the community plus everything we teach.
Founding rate until 31 October 2026: $9 and $49, locked for as long as you stay.

Compare both tiers

One part of the Guild

Once a year, the Guild meets in person for five days.

The Residency at Lakemore — January 14–18, 2027, in Traverse City, Michigan. Thursday to Monday over the MLK weekend, so it costs most people two days of vacation. Eight seats, one lakehouse, laptops open. Meals and sessions happen next door, in the house the team stays in. You arrive with something you’ve been meaning to launch and go home with it built: your founder’s video, your brand video, your headshot, your budget, and the marketing plan that fills it.

Everyone who comes gets a year of The School, the Guild’s $99 tier, included.

The lakehouse — eight seats

One house, eight seats. We’d rather run one full house than two half-empty ones.

Private room, king bed · $7,000
Private room, queen bed · $6,500
Private room, twin bed · $6,000
Shared room, two beds · $5,000

A group of women sitting in armchairs around a lit fire, notebooks open on their laps. — Fire lit, notebooks open. Three full working days.

A long table of women eating dinner together, mid-conversation and laughing. — One table, every night. You are not cooking.

Five women standing arm in arm on the grass by a lake, laughing together, one still wearing an apron. — And the people who now know your name.

From Anna VanAgtmael’s Traverse City retreats, 2021–2023.

See the Residency Book your seat

Who runs it

Three people. Three jobs.

Robert Earl

Being discovered

Strangers arrive, and that is what fills the seats. Search, the answer engines, the podcast’s reach, and the ads that put you in front of people who have never heard of you. Twenty-five years building sites that search engines, and now AI, actually cite.

Stacy Earl

Getting booked

The stranger who arrived decides you’re the one. The founder video, the words in your guest’s own language, the page that converts, the offer, and the emails after the deposit that keep them warm until they land. Twenty years of it, including the marketing lead at #11 on the 2024 Inc. 500. A page is a conversion rate, not a mood board.

Anna VanAgtmael

Delivering the week

What it costs, what you charge, and everything after they’ve paid: getting them ready, getting them there, delivering the week. More than twenty-five retreats with Wandering Roots since 2018, and the scars from the first few.

Two of the three of us are marketers, and that’s on purpose.
— from the Guild’s welcome post

Meet all three properly

The part nobody else offers

List what you’re hosting. Keep nearly all of it.

Every marketplace that fills your trip takes a cut of it, including on the seats you filled yourself. Ours is the smallest cut in the category — 5% for School members, and nothing at all, permanently, for founding members. We’re not in the booking business, we’re in the teaching business; the commission is what people who aren’t members pay instead of a subscription.

See the listings page

Commission for founding members, permanently

$19

To get in the door