EP 262 Culture Building: How to Create a Retreat Experience That People Come Back To with Nathan Jamail
Release Date: 03/19/2026
EP 262 Culture Building: How to Create a Retreat Experience That People Come Back To with Nathan Jamail
The Retreat Leaders Podcast
Most retreat leaders focus on the itinerary. But what makes guests come back year after year isn’t the schedule - it’s the culture. In this episode, Shannon is joined by leadership expert and culture strategist Nathan Jamail (whom she is biased to say is amazing) to break down how retreat leaders can intentionally build culture instead of just planning programming. They discuss: How culture impacts everything How to create loyalty beyond a single event Alumni communities that actually stay engaged Setting customer experience standards Why some retreats create raving fans -...
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EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail
The Retreat Leaders Podcast
Confidence isn’t just mindset crap. It affects your pricing, your messaging, your sales conversations and your boundaries. And ultimately - whether your retreat fills or flops. In this episode, Shannon is joined by leadership expert, sales strategist, and bestselling author Nathan Jamail (she is biased, but he is pretty damn amazing) to unpack the real reason many retreat leaders struggle to sell out their events: lack of business confidence. They discuss: Imposter syndrome in the retreat industry Underpricing rooted in insecurity Overexplaining instead of leading What confident...
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A Special Edition: Announcing WeTravel as a Sponsor of the Retreat Industry Forum + Why Their Platform Is Built for Retreat Leaders
The Retreat Leaders Podcast
Running a retreat business requires more than just creating transformational experiences. Behind every successful retreat is a system that manages payments, bookings, logistics, guest communication, and operations. In this special episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Erin and Alison, co-hosts of the Retreat Industry Forum, along with Mariana from WeTravel, to officially announce WeTravel as a sponsor of the upcoming forum. During the conversation, Mariana from WeTravel shares how their platform was specifically designed to support retreat...
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EP 260 Not All Events Are Equal: How to Discern Real Value in a Noisy Event Space with Dora Rankin
The Retreat Leaders Podcast
In today’s entrepreneurial world, there is no shortage of conferences, summits, masterminds, and learning forums. But here’s the real question: How do you know which ones are actually worth your time, energy, and money? In this episode, Shannon sits down with Dora Rankin to talk about discernment in business spaces - especially in a post-COVID world where the coaching and event industry has exploded with noise, hype, and inflated promises. They dive into: Why entrepreneurs are more discerning than ever The rise of “smoke and mirrors” marketing How to vet event hosts and speakers...
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EP 259 Should You Have a Co-Host in Your Retreat Business?
The Retreat Leaders Podcast
Partnerships can be powerful… and they can also quietly wreck your retreat business. In this episode, Shannon Jamail breaks down one of the most common questions retreat leaders ask: Should you have a co-host? After being asked this question during a keynote in LA, Shannon’s immediate answer-“Don’t.”-got a laugh… and opened the door to a real conversation retreat leaders need to hear. Shannon shares the good, the bad, and the expensive lessons she learned from early partnerships, including a situation involving copied content and the painful reality...
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A Special Edition: A Fireside Chat about The Retreat Industry Forum with Alison, Erin & Shannon
The Retreat Leaders Podcast
In this special fireside chat, Shannon Jamail, Alison, and Erin pull back the curtain on the evolving energy of the Retreat Industry Forum — and why this year’s attendee profile looks different than ever before. What started as a vision to elevate the retreat industry is quickly becoming a high-level gathering of experienced retreat leaders, business owners, venue operators, and industry professionals ready to scale smarter and connect strategically. The trio discusses: The shift toward seasoned retreat professionals attending Why the Forum is not a beginner workshop —...
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EP 258 What I Wish I Had Done Differently When I First Built My Retreat Business
The Retreat Leaders Podcast
When I first started building my retreat business, I made mistakes. Not small ones - real ones that cost time, money, energy, and unnecessary stress. In this episode, I’m pulling back the curtain and sharing: What I personally wish I had done differently in the early days The most common mistakes I see retreat hosts still making today And how to avoid burning out, underpricing, or building a retreat that looks good on paper but feels exhausting in real life If you’re hosting retreats (or thinking about it), this episode will help you build something that’s clear,...
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EP 257 Belonging Is the New Luxury: Why Retreats Matter More Than Ever with Dan Berger
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Dan Berger to talk about something the retreat industry doesn’t discuss nearly enough: belonging. Dan shares his personal journey—from selling his event-planning software company for $100M, to grappling with his own sense of belonging, to ultimately creating Assemble Boise, a retreat and gathering space intentionally designed for human connection. Together, Shannon and Dan dive into: Why men are facing a serious belonging and mental health crisis How retreats can act as temporary communities that create lasting impact...
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EP 256 Building Pilates Retreats in Europe: Creativity, Logistics, and Expansion with Bessie Refalo
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Bessie Refalo, a yoga and Pilates retreat leader who is carving out a unique lane in the wellness retreat industry - reformer Pilates retreats in Europe. Bessie shares the behind-the-scenes reality of creating retreats that require specialized equipment, including the challenges of finding venues with reformer Pilates machines and the creative solutions she’s used to make her retreats possible. From transporting reformers by lorry in Portugal to discovering bespoke studios in Italy, this conversation is a masterclass in...
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EP 255 Building a Soul-Led Retreat Business While Working Full-Time with Amy Jaggers
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Amy Jaggers, a coach and retreat leader who is building a soul-led retreat business while still working full-time. Amy shares how she helps professionals step off autopilot and reconnect with balance, clarity, and purpose through meditation, mindfulness practices, retreats, and wellbeing circles. She opens up about what it really looks like to grow a retreat business alongside a demanding career — including boundaries, time management, and integrating her “soul work” into her corporate role. Together, Shannon and Amy...
info_outlineMost retreat leaders focus on the itinerary.
But what makes guests come back year after year isn’t the schedule - it’s the culture.
In this episode, Shannon is joined by leadership expert and culture strategist Nathan Jamail (whom she is biased to say is amazing) to break down how retreat leaders can intentionally build culture instead of just planning programming.
They discuss:
-
How culture impacts everything
-
How to create loyalty beyond a single event
-
Alumni communities that actually stay engaged
-
Setting customer experience standards
-
Why some retreats create raving fans - and others don’t
If you want recurring revenue, repeat guests, and long-term brand equity, this episode will shift how you think about your retreat business.
Recorded in our new studio space in Austin - and available on YouTube as well.
What You’ll Learn
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Why itinerary doesn’t equal experience
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The role leadership energy plays in culture
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How to design belonging - not just activities
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How to turn one-time guests into long-term community
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The operational standards behind unforgettable retreats
Key Takeaways
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Culture is what people feel, not what’s printed on the schedule.
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Loyalty is built intentionally, not accidentally.
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Clear standards create consistency and trust.
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Raving fans are the result of alignment and leadership - not luck.
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Retreat businesses that scale focus on community, not just events.
Watch on YouTube
This episode was recorded in our new Austin studio space.
You can now watch the full conversation on YouTube.
Subscribe:
Learn more about Nathan: https://nathanjamail.com/
Join Nathan and Shannon at the Forum: https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum
The Retreat Leaders Podcast Resources and Links:
Thanks for tuning into the Retreat Leaders Podcast. Remember to subscribe for more insightful episodes, and visit our website for additional resources. Let’s create a vibrant retreat community together!
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TIMESTAMPS
Defining Culture in Organizations (00:02:04) Nathan explains what culture means, using energy, attitudes, beliefs, and the thermostat analogy.
Mandating Culture & Event Laws (00:03:00) Discussion on the importance of setting clear cultural expectations and event “laws” for retreats.
Authenticity & Alignment in Retreats (00:04:43) Shannon and Nathan discuss the need for alignment between retreat leaders and attendees, especially for international retreats.
The Dangers of Misalignment (00:05:47) Exploring how misaligned guests can negatively impact the retreat atmosphere and culture.
Marketing to the Right People (00:07:13) Emphasizing the importance of targeted marketing and being clear about who the retreat is and isn’t for.
Gratitude and Team Culture (00:08:25) Lighthearted discussion about gratitude within their team, referencing team members Josh, Lily, and Sharon.
The Cost of Keeping Misaligned People (00:09:12) Nathan explains why keeping misaligned people (for fear of loss) damages culture in both business and retreats.
Quality Over Quantity: Pricing & Numbers (00:10:21) Debate on charging more for fewer, better-aligned attendees versus filling retreats with anyone.
Hiring & Team Alignment (00:15:04) Common mistakes in hiring misaligned team members and the impact on guest experience.
The Airport Test & Culture Fit (00:13:57) Nathan introduces the “airport test” as a way to assess cultural fit among team members and guests.
Sacrificing Culture in Tough Decisions (00:14:33) How leaders often sacrifice culture first when making difficult choices, and the consequences.
Setting the Tone: Messaging & Boundaries (00:18:09) Shannon shares practical ways to set cultural expectations from marketing to the retreat’s opening night.
The Ted Lasso Theory: Be Curious, Not Judgmental (00:20:03) Nathan references Ted Lasso to illustrate the value of curiosity and non-judgment in building culture.
Energy as a Differentiator (00:21:37) Discussion on how the energy and culture you create is more memorable than content or location.
Closing & Invitation to Future Events (00:22:18) Shannon and Nathan wrap up, reflect on past recordings, and invite listeners to join their upcoming event.
Outro & Call to Action (00:23:54) Podcast outro with reminders to subscribe, review, and access free resources.