Fifty Guests a Year, One Button: How AI Changed the Way We Run Retreats

The first retreat Erin and I ever hosted, neither one of us had ever been on a retreat. Not once. (Looking back, that was either very brave or a little bit nuts. Probably both.)

That was 2017. We’ve been hosting ever since, and these days it works out to around 50 guests a year between our retreats in Nosara and our yoga teacher trainings.

Here’s the funny part. When I look back across almost nine years of retreats, the week itself has barely changed. We’ve polished it plenty, but the bones are the same as that very first one, because it worked so well.

What changed is everything behind it.

The week before used to be chaos

I’ll be honest about what the week before a retreat used to look like. Chaos. We had a basic template and we kept making it better, but we were terrible at taking notes, so every single time we ended up reinventing the wheel. Stacks of paper. Spreadsheets on top of spreadsheets.

The hard part was never the yoga, and it was never the guests. It was the data. Every guest arrives with their own story, and I had to get each one into a shape I could actually use. When does their flight land? What can’t they eat? Who are they rooming with? Then I’d take all of it and try to build the shuttle schedule by hand.

All of it manual. Enormous amounts of work, for every single retreat.

Now it’s one button

This fall, Claude and I built a retreat app, and the first thing it fixed was that job. Our bookings live in WeTravel, and now I push one button and every guest flows straight into the app. Their flights come across with their diets. Their contact details come across with how long they’ve been practicing. Everything I used to type in by hand is just there, waiting for me.

Then there were the questions. Always, always, always questions. How am I getting picked up? Who do I call if my flight is late? What happens if this goes wrong, or that? Are towels provided?

So we did something I wish we’d done years ago. We went back through every email guests had sent us and started answering those questions before anyone had to ask, and thus the app was born. Now every guest gets their own custom app with their flight and their room information and their ride on it, plus the answers to everything people used to write in about. The schedule and the shuttles. The activities. The journal prompts. The memories and the photos. It’s all there in one amazing app.

The shuttle puzzle

The shuttles were my favorite surprise. Getting a group from the airport to Nosara is a real puzzle. Flights land all day long. A van only holds so many people, and every extra run costs money.

I gave the app our rules. How many people fit in a van. What a shuttle costs, and what that works out to per person. It came back with the best schedule for the whole group, and I can still nudge it by hand when I want to.

Guido, who runs our shuttle schedules and retreat shuttles in Costa Rica, was blown away by how easy it was. I’ll take that.

Same week, different road to get there

When I first sat down to write about this and thought about how much time I’ve saved using AI, the word I used was immeasurable. And if you made me put a real number on it? Oh my lord. Easily 50 hours per retreat.

Here’s what I love about that. Our guests have consistent, beautiful weeks every single time. The same bones as that very first retreat (back when neither of us had a clue what a retreat was supposed to look like) have evolved and changed into an incredible experience for our students. It doesn’t take a mountain of paperwork to get there anymore.

This is the first of four pieces on how we actually use AI when we travel, picking up from The Month AI Stopped Helping and Started Doing. Next comes how AI finds our campsites, then what I actually say to it, and finally the notes every AI reads first. Because that’s what Five Parks Life is all about. It’s not just yoga, and it’s not just travel. It’s about how we live, and this is a big part of it now.