The Hosting Guild
She was on the panel. I was looking up her website.
How the Guild started. A conference in Denver in May, an Italian dinner, and a calendar entry two people have kept every Thursday since.
In May of this year I went to the Retreat Industry Forum in Denver.
It was put on by three people who have each spent years in this business — Shannon Jamail, Alison Katschkowsky and Erin Haag. I'm saying that at the top rather than the bottom, because everything below happened because they put a room of us together.
On the first night there was a happy hour. I met Anna VanAgtmael there. It was pleasant, it was brief, and I would have forgotten it.
The second morning
She found me before a session and asked what I run.
I told her about the trips I run for book lovers and book clubs. She asked the kind of questions that come from someone who has actually done this, not read about it. Then she went off to sit on a panel.
So I listened to her talk. And while she talked, I looked up her website on my phone.
Her site said two things. Women's adventure retreats. And operations and coaching for retreat hosts. That was it. No throat-clearing, no paragraph about transformation — the two things she does, named plainly enough that I knew straight away whether they were for me.
They were. She was speaking my language with the words on the page.
Her website didn't need to be found by thousands of people. It needed to be right for one person who was already in the room.
That distinction is the part that has stayed useful to me. Most sites in this industry describe a feeling. Hers described the work. And because it did, a stranger went from mildly interested to certain in the time it took her to answer one question.
At lunch, I asked her to dinner.
The dinner
Italian food. Very good cocktails. We closed the place.
I'm not going to over-tell this one. Two people who do adjacent versions of the same hard job found each other and talked until the restaurant wanted its table back. If you've had one of those dinners you know. Nothing was decided and nothing was proposed.
And it could have ended there
This is the part I think about most.
Nearly all of them do end there. You have the good conversation. You mean to follow up. Then you go home to the inbox and the launch that's already behind, and the deposit you've spent, and the page that isn't converting — and some months later you can't quite remember her last name. That isn't a character flaw. It's what happens when the work is already more than one person can carry.
What we did instead wasn't clever. We made a point of finding each other several more times before the conference ended — properly, not oh, hello again in a queue. And before we flew home we put a call on the calendar for every week.
There was no business reason for it. There was nothing to discuss. We booked it anyway.
And she shows up. And I show up.
That's the whole mechanism. Not networking, not a system. Two people who kept an appointment neither of them had a reason to keep, for long enough that the reasons turned up on their own.
What the call turned into
In order:
- A weekly call.
- A three-day working weekend.
- A podcast.
- A five-day residency in January.
- This.
Somewhere in there we worked out that our skills don't overlap so much as interlock. Anna has run more than twenty-five retreats since 2018, across several countries — she knows what happens once people arrive. I've spent twenty years leading marketing for large organizations, and for dozens of private clients. Each of us had spent years quietly working around the half we didn't have.
That took three months.
I'll put the uncomfortable version first, because it's the honest one: we have known each other since May. If you want to hold that against the list above, hold it — three months is not a track record, and I'd think the same thing reading this.
But it's also the point. Nothing on that list was planned. Each one turned up because the previous one had happened and we were already talking on Thursday, so there was somewhere for it to go. That's the part that compounds. Not the idea — the standing hour that catches the idea.
And the call is still every Thursday.
I want that on its own line, because it's the only real evidence here that any of it worked. A business grew out of that hour, and the hour didn't get replaced by the business. Same slot, most weeks running shorter than it should.
One plus one, occasionally, is three
Neither of us builds this alone. Not for lack of ability — the thing needs both halves, and there was no version of it one person was going to think of on their own.
What we keep coming back to is that we can't be the only two. Someone is running a retreat or a group trip right now who is excellent at the week and stuck on the filling, or the reverse. She's working it out alone, late, because there's nowhere obvious to go and ask.
We wanted somewhere obvious. So we built one.
That's the Guild. A room of people doing the same difficult job, open year round, where whoever answers you on a Thursday has sold the exact thing you're trying to sell.
It started with a happy hour and a calendar invitation neither of us had a reason to accept.
That room exists now, and you can be in it
Everything above is how the Guild came to exist. This is the part where you can join it. It's a room of people doing the same difficult job — open year round, where whoever answers you on a Thursday has sold the exact thing you're trying to sell.
TWO WAYS IN
The Porch — $19 a month. The room. Other hosts, the conversation, somewhere to ask the question you’ve been embarrassed to ask — and the recording of every week’s office hours, so you hear what got answered.
The Practice — $99 a month. The room plus everything we know: the full Library open on day one, commission-free listings, the Practice Floor — and you’re in the office hours rather than listening to them afterwards. That’s the difference the $99 buys. On the Porch you hear somebody else’s question answered. On the Practice, the question is yours.
The whole Library is open the day you join. Nothing drips, nothing unlocks later, nothing is held back to keep you subscribed. And we keep adding to it — you are not going to reach the end of it and wonder what you’re still paying for.
We're still two people who found one conversation useful enough to keep having it. The only difference is that now there's a door.
Anna VanAgtmael runs Wandering Roots. Stacy Earl runs Route & Retreat. With Robert Earl, they run The Hosting Guild — and yes, they still talk every Thursday.