Two of the three of us are marketers, and that’s on purpose.
Empty seats are what close these businesses. Not bad experiences. So the people teaching you are the ones who fill things, plus the one who has run the room ninety times and knows what breaks at hour forty.
A women’s reset in Costa Rica, a writing week in Michigan, twelve people going to the Indy 500 — underneath, it’s one job.
Run the room → fill the seats → get found.
Anna VanAgtmael
Anna runs Wandering Roots, which she started in 2018 after a car accident put her in a neck brace for fourteen weeks and handed her, in her words, a crystal-clear perspective on every basic, boring life choice she had ever made. She dismantled a comfortable decade and rebuilt it around taking people somewhere.
Since then she has hosted retreats from Banff to Scotland to the Smokies, been written up in Woman’s World, and spent the years between mentoring other women on how to host retreats that are transformational and profitable — a distinction she is unusually blunt about. She teaches the budget session at the Residency, and she will tell you upfront that it always turns into a conversation about money mindset, because it always does.
Her own summary of the job: she spends most of her time convincing clients to get out of their own way, because it takes real courage to step past the excuses we all build to avoid the edge of our comfort zone.
In the Residency, Anna answers one question: when sixteen people are in your room and something goes wrong on day two, what do you do?
Stacy Earl
Stacy has spent twenty years in marketing and business development — direct-to-consumer work and the strategy behind it — getting real people to notice, trust and choose. She has led marketing for a consumer rewards app that landed at #11 on the 2024 Inc. 500, a heart-health platform and a national healthcare brand, as the senior marketing leader at two of the three. In some of that work she was emailing millions of people and carrying both acquisition and retention: the two numbers a business actually lives on.
She has been building websites since 1999, back in the pure-HTML days, and she is a licensed travel advisor who runs a small travel company of her own — which means she knows this world from the inside. The enquiry that doesn’t convert. The site that undersells what you actually do. The marketing that only happens when there’s a spare hour, which there never is.
She also holds an executive MBA from Johns Hopkins, which comes up far less often than the fact that she will read your sales page and tell you the true thing about it.
In the Residency, Stacy answers one question: what do you publish, where, and in what order, so the seats are gone before the date arrives?
Robert Earl
Robert is an Air Force veteran and a lifelong motorsports fan who has been to every Indianapolis 500 since 2001. For sixteen years he has built affiliate-marketing sites that earn their traffic, and his edge is structure: he organises content the way search engines — and now AI — want to read it, so it gets found and gets cited.
That discipline runs through Racing Passport, his travel companion for race fans who plan their year around the grandstands, and through the licensing guides that have helped more than ten thousand people start real estate careers.
At his core he is a teacher. He builds everything the same way — with precision, patience, and the belief that helping someone understand a thing they care about is work worth doing.
In the Residency, Robert answers one question: when someone types their problem into Google or asks an AI, why does what you’re hosting come back?
The gap we kept watching people fall into.
Anna kept meeting hosts who could run a beautiful week and could not sell one. Stacy and Robert kept meeting businesses whose product was genuinely good and whose marketing was a Squarespace page and a hope.
Retreat education mostly teaches the week itself. Marketing education mostly ignores that a group experience is a date on a calendar with a deposit against it and a hard deadline that does not move. The Hosting Guild is the two halves put in one room.
Empty seats are what close these businesses. Not bad experiences.