Nobody taught you the other half.
Everybody teaches strategy. Nobody sits down and does it with you. Here are the specific steps to host a retreat or group trip, in the order you need to do them.
The Other Half
Free: every step, in order, in eight stages.
From Anna, Robert and Stacy at The Hosting Guild.
They have the idea. Then they get stuck.
Meet Maya and Dan, our example hosts. You’ll follow them through the whole checklist, so you can learn from their mistakes instead of making your own.
Maya and Dan met at summer camp when they were fifteen. Thirty years later, somebody at every dinner party says the same thing: I'd pay anything to go back for one week. So one night in February they decide to build it. A summer camp for grown-ups, with cabins on a lake, canoes at dawn and s'mores at the fire.
They buy the web address that night. By the weekend they have a logo and a landing page with a beautiful photo of the lake at the top. Then they try to write the next line on the page, and they can't.
If that sounds like you, you’re in very good company. Maybe you came home from a conference buzzing with ideas, and a month later you have a notebook full of strategy and still don’t know what to do first, or how any of it turns into a profit. They don't need more ideas. What nobody ever handed them is the order: what has to happen first, so that everything after it can. The checklist picks up where they get stuck.
From Anna
“I always tell everybody to just dream big in the beginning. Write down your dream itinerary and any specific details, and then work backwards.”
Most retreat and group-trip courses help you answer the big questions.
- Who is it for?
- What will they go home with?
- Where should it be?
- What should the days feel like?
- What should it cost?
- How will people find out about it?
- And then what?
Those matter. But answering them is only half the job. The other half is the doing: which step comes first, what it depends on, and what goes wrong if you skip it.
From Stacy
“Too often what we saw was a lot of high-level strategy, which got you super excited and ready to come home. And then as you got home, you’re like, ‘And now what do I do?’”
Do you want to see the other half they miss?
Hi. We’re Anna, Robert and Stacy.
Two marketers who fill seats, and a host who has run the room more than twenty-five times. We run The Hosting Guild together.
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The one who runs the room
Anna VanAgtmael
Started Wandering Roots in 2018 and has hosted retreats from Banff to Scotland to the Smokies. She teaches the budget, and it always turns into a conversation about money mindset.
Fun fact: Wandering Roots came out of fourteen weeks in a neck brace, and a long hard look at her life choices.
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The one who gets you found
Robert Earl
For twenty years he worked in real estate, which he describes as waking up unemployed every day. That’s why filling seats is the part he loves. Today he hosts race trips through Racing Passport and makes sure Google, and now AI, can find what you publish.
Fun fact: he’s an Air Force veteran who hasn’t missed an Indianapolis 500 since 2001.
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The one who fills the seats
Stacy Earl
Twenty years in marketing. She hosts literary escapes for small groups of women, and her biggest retreat was 500 people in Savannah. She will read your sales page and tell you the true thing about it.
Fun fact: she lived in England for three years, has traveled on four continents, and these days works roughly a gazillion hours a day.
You bring the dream. We’ve got the order.
The three of us, Anna, Robert and Stacy, sat down with everything we’ve learned running retreats and group trips and helping other people run theirs, and wrote down every step, in order, in eight stages. Each one tells you what has to be done before you can start it. Want to see them?
From Anna
“I really believe asking for help and not doing it alone is the gateway to doing it well.”
Would you rather work through the list with us at the table? That is what the Residency is for: five days at Lakemore, January 14 to 18, 2027.
See the Residency week · Book a free half hour with Anna, Robert or Stacy