EP 262 Culture Building: How to Create a Retreat Experience That People Come Back To with Nathan Jamail
Release Date: 03/19/2026
EP 265 The Communication Shift That Can Transform Your Retreats with Joel Weldon
The Retreat Leaders Podcast
Retreat leaders spend months planning the location, the schedule, the experiences, and the transformations they want their guests to have. But there is one skill that quietly determines whether your retreat truly lands with your audience. Your ability to communicate. In this episode of The Retreat Leaders Podcast, Shannon sits down with Hall of Fame speaker Joel Weldon to talk about the powerful role communication plays in the success of retreats - from filling the room to creating deeper breakthroughs for attendees. Joel has been paid to speak at more than 3,000 events and has coached over...
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The Future of the Retreat Industry: Why We Need Standards, Community & Leadership with Holly Porter
The Retreat Leaders Podcast
The retreat industry is growing so fast. Especially in the last 6 years. But here’s the problem: There has never been a central place for retreat leaders, venues, and professionals to connect, collaborate, and operate at a higher standard. Until now. In this episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Alison, Erin, and Holly Porter, founder of the International Retreat Association, to talk about the future of the retreat industry - and why the timing for this shift couldn’t be more important. Holly shares her powerful personal story - from building 12...
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EP 264 Building Momentum: Staying the Course When Results Feel Slow
The Retreat Leaders Podcast
One of the hardest moments in the retreat business is the quiet period after you launch something. You announce your retreat. You post about it. You send emails. And then… crickets. In this solo episode, Shannon Jamail talks about why slow results are not a sign that something is wrong. In fact, momentum in the retreat industry is rarely sudden — it’s usually the result of consistent, focused action over time. Shannon breaks down the common traps retreat leaders fall into when results don’t appear quickly, including shiny object syndrome, comparison traps, and abandoning strategies too...
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EP 263 Trust Leaks in Retreat Businesses: The 5 Places Retreat Leaders Lose Credibility with Debbie Simmons
The Retreat Leaders Podcast
Trust is the currency of the retreat industry. Guests invest their time, money, and emotional energy into retreat experiences expecting transformation, connection, and professionalism. But often, trust doesn’t break in big dramatic moments - it slowly leaks through small gaps in leadership, communication, and delivery. In this episode, Shannon sits down with Debbie Simmons to discuss the five most common “trust leaks” in retreat businesses and how retreat leaders can repair them before they damage reviews, referrals, and long-term loyalty. They break down where trust most often breaks...
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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 —...
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.