What Does It Take to Be a Luxury Retreat Leader?

A couple years ago I got an email that caught my attention because I review retreats and am always looking for new retreat centers. The subject line read: “Could Imiloa in Costa Rica help take care of all the details for your retreats?” So I clicked on it and read the note from Jake Sasseville at the Imiloa Institute:

Hey Stephen,

I wanted to reach out personally and say hi. My team of researchers at Imiloa is scouring videos, podcasts, and websites to discover some of the most interesting and impactful educators, transformational leaders, or retreat hosts around the planet … We’ve helped over 200+ retreat hosts be more profitable, joyful, and free, and we enjoy an 80% renewal with our treasured clients.

We handle every part of the experience, including an all-expense-paid site visit to Costa Rica and marketing support. We create content for you on-site, provide luxury ground transportation and private planes, offer gourmet cuisine, and support you with a 50-person team that feels so familiar, like family. All for a fraction of what you would likely pay elsewhere …

I didn’t respond to Sasseville’s email, but a couple days later it came again. Then, Sasseville sent another: “Are you a high achiever struggling with fulfillment?” And another: “Discover your calling: Meet Your Wisdom Trust Community.” And then, “Final Call: Apply to Join Wisdom Trust Today.” A week later, I got “Join me every Wednesday for ‘Ask Jake Anything:’”

Trouble filling your retreat? Let’s figure it out together.

Want to more powerfully enroll people without being pushy and selling them? I’ll teach you everything I know.

Want to convert EVERY objection into a commitment? I’ll show you my 10-step process and we’ll tailor it to your event.

Not sure Imiloa’s for you and want to be a fly on the wall and learn more about it? Be our guest.

The emails continued for eight months before I clicked on a video link and watched images of cheerful people getting into small planes and luxury cars and driving into a jungle paradise. I then emailed Sasseville and apologized because it took me so long to respond. This really looked like fun. My email led to a Zoom call.

Sasseville was ebullient. He told me he believed in total transparency. Before starting Imiloa, he said, he had never been on a retreat. He’d been a late-night talk show host in Los Angeles. Then he had an idea for a new model of retreat center that provided the opportunity and training for anyone to step into the arena of luxury retreats and make real money doing it. He would succeed because the retreat leaders first have to “buy out” his center for the duration of their retreats and then use the training to sell all the rooms to their own clients for a profit.

He opened Imiloa as Covid struck, and yet he managed to keep his staff employed and build trust with the local community by hosting in-country retreats. Imiloa was now selling out, he was opening a second center in Costa Rica, and he had plans to build centers on every continent. He told me that if I really wanted to understand the place, I could join a free three-night familiarization retreat for leaders. The next trip was full, but Sasseville offered me his own quarters. All I had to do was get myself to San José, Costa Rica, in time to catch the private plane.

The Big Wow!

The adventure began as I remembered from the video. About 20 of us—mostly women—met one morning at the small domestic air terminal at the San José airport and paraded out to two 15-passenger planes. Ours was a friendly, outgoing group who would soon be hosting retreats at Imiloa—including a Human Design Workshop, a Goddess Wisdom Council, and business leadership. After a scenic, 45-minute flight over the jungle, we landed at the rustic Quepos Airport, where luxury cars waited. We swapped stories for half an hour until we turned onto a narrow gravel drive into the jungle and stopped in front of a grand open-air pavilion, the “Heart” of Imiloa. We were handed mocktails (alcohol is not permitted), and I then met Sasseville, whom everyone already knew through videos and Zoom calls.

He proved to be the host of hosts: His “opening circle” was a model for each of these future retreat leaders to copy for their own retreats, as was the property tour. As it turned out, I had the best accommodations, a spectacular hilltop suite imported from Bali with an outdoor tub and shower. The retreat leader could choose to stay in this grand suite or sell it to a guest for a premium price. There were two other “Bali Sunset suites.” Otherwise, guests stayed in cabins and domes shared by two or three people, with a maximum of 32 guests. After the tour, we met back at Heart for lunch, which—like all the meals—was foodie-grade vegan. My impression was that everything at Imiloa had been done to enable new retreat leaders to step into Sasseville’s role as host.

The next morning, I enjoyed yoga in a grand, treetop-level pavilion called “Home,” had a fine breakfast at Heart, and then gathered with the group to hike down a steep path to a waterfall. There, I was ritually finger-painted with blue clay by a partner before I then painted her, and then we all jumped into the falls to wash off. Fun! The Blue Clay Ceremony was one of many rituals that could be added to a retreat package for an extra fee.

The Hard Reality

A sumptuous lunch was followed by “content creation,” which I now understood was the ultimate goal of the familiarization tour. One of the spectacular Bali suites had been turned into a video studio where each retreat leader was interviewed to create a promotional video they would use to sell their own retreats on social media.

It was late that afternoon—at the marketing workshop at Home with Sasseville—that I understood the stakes of the video content creation. Each of these aspiring retreat leaders had already signed a contract to “buy out” the center: all 32 beds for four nights at $400 per person per night—or $64,000. When Sasseville had told me that during our Zoom, it sounded empowering, a matter of “putting your stake in the ground.” But as we went around the circle and each leader reported how many tickets they had sold, several had not yet sold any. They still had months to sell before their retreats, and maybe each person would become a highly paid retreat leader, but first they had to pay off their $64,000 debt to Imiloa—and one businessman had booked two retreats, back-to-back.

The next day was mostly content creation and free time, in which the group shared marketing ideas and figured out how to stay connected after we got home. Most seemed “all in!” And the staff of Imiloa was clearly dedicated to helping each retreat leader learn the marketing skills necessary to succeed. Nevertheless, I found myself pulling away. Selling retreats is hard work even for marketing pros and bestselling authors. I didn’t want to shake anyone’s confidence by sharing my personal doubts, but I was glad not to have signed a contract to become a real member of this group.

An Easier Start

I left the others at the San José airport, where I had arranged to meet someone for a visit to another exotic retreat center called Rios Lodge on the Pacuare River. That journey begins with a two-hour drive and then whitewater rafting to reach the retreat. The site is both rustic and spectacular, and the all-inclusive cost per person is a fraction of Imiloa’s—a small fraction if you fill the retreat’s eight new eight-person bunkrooms. (Rios has a total of about 100 beds.) And you don’t have to buy the place out. If you bring a group of 10 people, for example, your own trip is free. It was a level of risk I could easily imagine taking.

Months later, I talked to Sasseville and checked in with a few of the new retreat leaders. The man who booked two retreats back-to-back had sleepless nights and lost “a ton of money.” One woman lost it all. I think the rest of the group did fine, and I’m sure they learned a lot. But it seemed like a lot of pressure for a spiritual retreat.

Look Before You Leap

Luxury retreats are a high-risk business. Before you sign a contract with any retreat center, close your eyes and ask yourself, What is my gift? How do I want to share it? Then open your eyes wide and ask, Do I know my target audience—their dreams and their challenges? Can I reach them with an offering that feels like a gift and earns me a living?

Then test it. The businessman who lost money signed his contract and then sent an email trying to sell his planned retreat to his list of 10,000 prospects—and got zero response. Better to send emails and videos to gauge the response before you sign.

This article appeared in the May/June 2026 issue of Spirituality & Health: A Unity Publication^®. Subscribe now.